Jimmy was ordinary enough. Slight of build, maybe and bashful but he had no idea the passion that lay waiting within him. Completely absent from his thoughts, the young man’s obsession hid like a storm over the horizon until the night he crossed paths with the wrong girl at the wrong time.
Or was she the right girl, delivering the awakening he needed?
It all started with a kiss.
That unique taste came from his own body and Jimmy wasn’t the first to experience sex that way. But, for some, the experience is more than a spicy erotic moment. For a very few, it immediately becomes an obsession. Right or wrong, Jimmy was one of those few.
Soon, Jimmy finds that he can’t satisfy his obsession solo and with a little help from Miss Wrong (Miss Right?), he puts on a dress to get what he needs. Then everything changed…
Almost immediately, the young man loses control. With the loss of control, he loses his dignity, all in the name of satisfying his desires – desires that only men can quell. His desire seem insatiable but, worse, it has no regard for how it is destroying the person it’s affecting. As a young man becomes a young woman, she loses her humanity and seems willing to ruin her life as her sexual desires lead her like a dog on a leash.
So much depravity… the new girl starts to regret what she’s become but it seems too late. She’s allowed others to take control of her and knows she’s become a slave to desire. Can she possibly pull out of this nose dive?
Right or Wrong is, in the end, a romance. It takes a long time getting there and, along the way you’ll meet a different sort of villain and a different kind of star in the show.
On the one hand, the villains are certainly unsympathetic people with bad character. But you can’t blame them completely because our hero has created his own problems; rather, his desires have created his problems. The villains are just happy to take advantage. You may think, “Who could blame them?”
Jimmy will put himself into situations of extreme humiliation and depravity. I suspect you’ll feel sorry for him but, then again, he’s doing it to himself. Will he escape the hell he creates?
By coincidence, Jimmy happens to live in the same apartment building as another young man who will find a journey that ends as a woman. Maybe you’ll find it fun to compare the experiences as one became Desiree and the other becomes Olivia. Their endings, though, are quite different. It’s almost as if karma is real.
Right or Wrong is loaded with images. I’ve tried to find or take pictures that show a transition. Honestly, this wasn’t easy and it may take a bit of imagination to feel that’s what you’re seeing but I hope it can work for you. Also I’m trying a different way to provide the girlfriend’s story as it plays out like a narrator of sorts. We’ll see if you like it.
There’s plenty of sex, some of it kinky and Jimmy, of course, transitions beautifully.
This is a fairly long story of around 100 chapters. Enjoy the ride.
Warning: ADULT CONTENT
Some Boys Were Meant to be Girls
You’ve seen them – petite young men with feminine features. These treasures are always in their 20’s; they’re short and fine-boned with pretty faces just waiting for a little nudge to step into a pair of high heels. Maybe they’re in touch with their desire, maybe they’ll fight it, but there’s always a happy ending. When you start reading my pages, think about the prettiest cross-dresser you’ve seen or transgender runway models – that’s who I write about.
These are fun tales and there’s no fun in hearing about the realities of acceptance or sexually transmitted disease, so you won’t find those in my fictional stories. You also won’t find magic, but I do write with a touch of science fiction, like glue-on breasts that pass as the real thing. In some cases, you’ll be reading real science fiction employing advanced procedures that are certainly not available (yet!).
While I say my stories are generally fiction, I do like including some truthful episodes and characters now and again. It’s up to you to think about what’s real and what’s made up, though, because I’m not the kind of girl who will kiss and tell.
Once they start wearing heels, some of these beauties will make up for lost time with sex – in some cases a lot of sex. Others will find love and romance. Once transformed, most of my characters find they like the company of men, some still prefer women, and a few… well, you guessed it, enjoy both.
There are some heroes and villains, comical mistakes and misunderstandings that, depending on the story, are all part of introducing a young man to his new feminine world. Once there, he might decide to pay occasional future visits or he might check in for good – each tale is a little different.
Lastly, with a few exceptions, these are adult stories with detailed erotic sexual descriptions and are not for minors. If you find sex scenes offensive, seek out the few that are noted as “All Ages” in their titles. If you don’t see that, sit back and wait for some steamy encounters as the new girls explore their new sexuality.
“I’ll bet your apartment’s pretty cool,” I suggest to the boy I just met. It’s a stupid line and I feel slutty even saying it but I know it’ll work.Coming to this pool was Shelly’s idea. She’s my girlfriend and she dropped me off here about a half-hour before. “The guy’s name is Carl and he knows what you’re wearing,” she had told me, “Your neighbors say he acts like a real ladies’ man.”
In denim short-shorts and a pink bikini top that I have no intention of getting wet, I opened the gate and waved goodbye. Shelly’s seeing a friend for lunch so I’ve got about an hour or so before she picks me up. I don’t feel great about this – the drop-off, the casual sex, or the fact that I’m a slutty girl who’s coming on to a boy I don’t even know.
“You look hot, Jimmy,” she said before I got out of the car. She’s the only one who still calls me that. To the boy I just met and to everyone else, I’m Olivia. Olivia… Olivia who wants oral sex. That’s who I am.
After all I’ve done I know that I’ve become Olivia but, still, part of me knows I shouldn’t be here, that I should show some dignity, that I deserve something more… something better. That part’s been growing over the last week and it’s been nudging out the part that brought me here, the slut I’ve become… is this really right for me?
I politely brushed off the two guys who found me first; I had a target in mind, after all. The boy who came over to talk to me is understandably surprised by my forward demeanor but Shelly left me here hoping I’d hook up while she visited with her friend and I can hear the clock ticking. Carl, the boy I’m here to please, smiles and seems to change as if he’s becoming more sure of himself as I come on to him. To him, I’m just a girl named Olivia who noticed him by the pool a week ago and that I’ve got a crush. He’s sort of boasting that he can see the pool from his living room, like I’m supposed to swoon of a pool-view apartment. He’s got a certain cocksureness about him that’s part cute, part out of place as if it’s underserved, but I don’t mind.
Shelly tells me that, though I’ve tried hard to make myself attractive, I’m not very pretty. I began doubting her recently and can’t help but think Carl’s too ordinary looking for me. Too ordinary, that is, if I were looking for a real boyfriend but, ha! As if I could ever have a normal relationship…
I give him a look that I’ve fine-tuned. Shelly smiled when she told that my eyes can say, “I’m easy,” better than words ever will. I think it’s working with Carl but I also tug at the binkini top, drawing Carl’s eyes to the tits I’ve had for the last few years. They’re doing their job. This boy’s about to be mine.
He’s taking the hint and I take his arm. I’m off to his pool-view apartment where, I’m sure, I’ll soon have exactly what Shelly hoped I’d get – a warm moutful of salty-sweet cum. It’s just another casual encounter set up by my girlfriend/pimp. Like most of the others, this guy has no idea I used to be an ordinary guy named Jimmy. He’ll boast, instead, that he picked up some slut by the pool. He’ll have a great story to tell but nothing like my own.
My First
I was 21 when I met Shelly at, of all places, a happy hour for work. She was friends with a girl I worked with who invited her to join us because, according to Shelly, my co-worker said, “You guys are all lame so I wanted someone cool I could talk to.” I supposed she was right – we were lame, at least I was. I had absolutely no thoughts of meeting someone at a work function but there she was.
Back then, I was Jimmy, a meek guy whose sole interesting feature was my green eyes. I was one of those kids who couldn’t even score a mercy date for senior prom and was terrified to be out of my parents’ house and on my own.
Light to dark, bitter to sweet, hot to cold – there’s a scale for most things and if I was timid and meek, you’d find Shelly at the other end, probably with a hand on one hip and scoffing as she looked down at me, at us – at the weak.
So, when she came back around to me an hour after her friend introduced us, I just seized. I was sure she was mistaken like, “You sure you have the right guy?”
But, no, Shelly had sought me out and even waited until I was alone. It was like she was on the hunt and telegraphed her intent with words and her body language – she was warm and obviously interested in me. “Am I going to be the millionth person to tell you have great eyes?” She said just one minute into our conversation.
I remember I blushed. It wasn’t because nobody ever mentioned my eyes but because it was Shelly. I looked around and the guys at work were watching us. Their expressions seemed to ask, “What the hell is she doing, talking to you?” or “Jimmy! Go for it!” Either way, they knew the sexy blonde could do better and I did, too.
Shelly was cool in that way important people might be. I had no idea if she actually was important (she was some kind of sales account manager and, no, I’d later learn, not a big deal) but she had an air of importance. She didn’t have a lot to say and didn’t seem to need to really talk much. She just… was.
So, when Shelly asked, “Hey, wanna get out of here?” I stumbled but agreed. She then turned toward the door and started moving before I had time to react. I was half-way out as I looked around, realizing I’d be leaving without saying goodbye. I caught up with her once outside and before I could ask what she had in mind, she said, “C’mon, I’ll drive,” then she paused, “My place?”
I think my heart skipped a beat. That girl was on a mission and I, little me – I was her mission. The whole evening raced like a film on fast-forward in my brain. Too fast to see details but there I was, star of my fantasy movie, losing my virginity in that woman’s bed. I didn’t even answer her. I couldn’t speak but just got in her car when she pointed to it.
She opened up with a little small talk during the drive. “So, those your friends?” she asked. While she maintained her presence and control, it was clear that small talk made her uncomfortable, like she was programed for her mission and conversation was a distraction.
“Not really,” I told her, “Just people I work with but we’re not friends. I haven’t really had time to maky any yet. I just moved here a few months ago.”
Struggling to keep words flowing, she asked the obvious questions like where I was from and if I get home much. “Not yet,” I told her, “My folks are retiring this year and they’re going to travel so they’re selling the house. They came by a few weeks ago to make sure I was okay.” She glanced over with a smile and it seemed she wasn’t really listening, just filling the void of anticipation. Never, never in my life did I think my first sexual encounter would be with such a bombshell. She may have seemed disinterested in conversation but she was clearly interested in sex.
Her interest made my hyper-aware of my own shortcomings and I wished I’d prepared better. I hadn’t done anything to hide my slight form that night. Dad had suggested I wear extra t-shirts to look normal but I only did that around him.
Then again, I guessed it was good that Shelly didn’t care about my body so I guessed she wouldn’t be put off by my little dick either.
She talked and talked as if I might get second thoughts about whatever she had in mind. Sure, I didn’t think Shelly was very interesting but, as for me, I couldn’t even think about asking her anything. I was way too nervous so we rode in silence for the last few minutes until she announced, “This is me,” as she pulled into an apartment building’s parking lot.
I sat there with a dumb expression as she got out of her car. Probably knowing I was uncertain, Shelly opened the passenger door and reached inside. “C’mon up!” she said cheerfully with the sort of confidence that just came naturally to her. I took her hand and felt a little tingle; I hadn’t held a girl’s hand since a brief period of dating in my junior year of high school.
I walked up the outdoor stairs with a lump in my throat. I worried that Shelly could feel the moisture on my palm or that she might even hear my heart beating loudly. I just couldn’t believe it…
We stood at her doorway as she worked the lock. I realized we were about the same height and guessed she also weighed around one-twenty or so. She gave me a smile just before opening her door as if to assure me that she wouldn’t hurt me.
That actually helped.
It was a warm mid-summer night and her apartment suddenly felt chilly for a skinny guy in a button-down shirt or a sexy woman in a light dress. Shelly apologized and explained, “Sorry, I like it cold when I sleep. I’ll turn down the A/C.”
She came away from the thermostat and headed right for me, clearly with something on her mind. I just stood there like prey. “You poor thing!” she cooed as she touched my arms, “You seem freezing!”
It was cold but I was frozen for other reasons. Then, as if she was done with any pretending, Shelly hummed and said, “Let me warm you up.” I wondered, later, if the whole cold-apartment thing was part of her plan.
She embraced me and planted her lips on mine. If my heart wasn’t racing before, it began at that moment. My hands stuttered in their progress, sure they were supposed to do something, unsure of what. My lips moved, I guessed, in the sort of way a girl would expect. Heck, it had been years. I told myself I’d explain I was out of practice and tried to get my head in the moment.
Just when I thought I was letting myself enjoy the kissing, I felt Shelly’s hand as it slid down the front of my pants with the kind of practiced ease I have when I open the refrigerator. Before I could freak out and try to offer some kind of apology, my seductress hummed with approval. It seemed I wouldn’t have to apologize for my small size, Shelly didn’t mind.
If things had been moving fast, they went into hyperdrive once Shelly had found my cock. With a little playing, it shrugged off any nervous signals sent from my brain and began pulsing its way to an erection. Shelly knelt and had my pants off with suspicious speed. If I had cared (I didn’t), I might have paused and fretted over the fact that she’d obviously brought me home with single intent.
Pants off, I looked on as Shelly easily made my entire organ disappear. She hummed as she sucked and all I could see was her hair so I reached down and started to gather it away from her face, guessing that was the chivalrous thing to do.
A few bobs of her head and Shelly backed off to expose a bright pink, eager and fully hard cock. Big or not, my erection was stiff and ready.
Maybe too ready because I could see cum glistening as a little came forth as if about to boil over. “Eh-eh-eh,” my professional lover teased, “Not quite yet.”
She led me to her couch and had me lie down flat. “I don’t know if I can last…” I began to say, worried that I’d come the moment she got on me.
Her confidence was soothing while still erotic. “You’re going to be just perfect,” she told me. She spun her hair to one side and moved down to get her mouth back on me. I was about to object, to tell her I was more than ready but then I realized I was… mmm… I was…
I was getting my first blowjob.
Back then, I was Jimmy, a meek guy whose sole interesting feature was my green eyes. I was one of those kids who couldn’t even score a mercy date for senior prom and was terrified to be out of my parents’ house and on my own.
Light to dark, bitter to sweet, hot to cold – there’s a scale for most things and if I was timid and meek, you’d find Shelly at the other end, probably with a hand on one hip and scoffing as she looked down at me, at us – at the weak.
So, when she came back around to me an hour after her friend introduced us, I just seized. I was sure she was mistaken like, “You sure you have the right guy?”
But, no, Shelly had sought me out and even waited until I was alone. It was like she was on the hunt and telegraphed her intent with words and her body language – she was warm and obviously interested in me. “Am I going to be the millionth person to tell you have great eyes?” She said just one minute into our conversation.
I remember I blushed. It wasn’t because nobody ever mentioned my eyes but because it was Shelly. I looked around and the guys at work were watching us. Their expressions seemed to ask, “What the hell is she doing, talking to you?” or “Jimmy! Go for it!” Either way, they knew the sexy blonde could do better and I did, too.
Shelly was cool in that way important people might be. I had no idea if she actually was important (she was some kind of sales account manager and, no, I’d later learn, not a big deal) but she had an air of importance. She didn’t have a lot to say and didn’t seem to need to really talk much. She just… was.
So, when Shelly asked, “Hey, wanna get out of here?” I stumbled but agreed. She then turned toward the door and started moving before I had time to react. I was half-way out as I looked around, realizing I’d be leaving without saying goodbye. I caught up with her once outside and before I could ask what she had in mind, she said, “C’mon, I’ll drive,” then she paused, “My place?”
I think my heart skipped a beat. That girl was on a mission and I, little me – I was her mission. The whole evening raced like a film on fast-forward in my brain. Too fast to see details but there I was, star of my fantasy movie, losing my virginity in that woman’s bed. I didn’t even answer her. I couldn’t speak but just got in her car when she pointed to it.
She opened up with a little small talk during the drive. “So, those your friends?” she asked. While she maintained her presence and control, it was clear that small talk made her uncomfortable, like she was programed for her mission and conversation was a distraction.
“Not really,” I told her, “Just people I work with but we’re not friends. I haven’t really had time to maky any yet. I just moved here a few months ago.”
Struggling to keep words flowing, she asked the obvious questions like where I was from and if I get home much. “Not yet,” I told her, “My folks are retiring this year and they’re going to travel so they’re selling the house. They came by a few weeks ago to make sure I was okay.” She glanced over with a smile and it seemed she wasn’t really listening, just filling the void of anticipation. Never, never in my life did I think my first sexual encounter would be with such a bombshell. She may have seemed disinterested in conversation but she was clearly interested in sex.
Her interest made my hyper-aware of my own shortcomings and I wished I’d prepared better. I hadn’t done anything to hide my slight form that night. Dad had suggested I wear extra t-shirts to look normal but I only did that around him.
Then again, I guessed it was good that Shelly didn’t care about my body so I guessed she wouldn’t be put off by my little dick either.
She talked and talked as if I might get second thoughts about whatever she had in mind. Sure, I didn’t think Shelly was very interesting but, as for me, I couldn’t even think about asking her anything. I was way too nervous so we rode in silence for the last few minutes until she announced, “This is me,” as she pulled into an apartment building’s parking lot.
I sat there with a dumb expression as she got out of her car. Probably knowing I was uncertain, Shelly opened the passenger door and reached inside. “C’mon up!” she said cheerfully with the sort of confidence that just came naturally to her. I took her hand and felt a little tingle; I hadn’t held a girl’s hand since a brief period of dating in my junior year of high school.
I walked up the outdoor stairs with a lump in my throat. I worried that Shelly could feel the moisture on my palm or that she might even hear my heart beating loudly. I just couldn’t believe it…
We stood at her doorway as she worked the lock. I realized we were about the same height and guessed she also weighed around one-twenty or so. She gave me a smile just before opening her door as if to assure me that she wouldn’t hurt me.
That actually helped.
It was a warm mid-summer night and her apartment suddenly felt chilly for a skinny guy in a button-down shirt or a sexy woman in a light dress. Shelly apologized and explained, “Sorry, I like it cold when I sleep. I’ll turn down the A/C.”
She came away from the thermostat and headed right for me, clearly with something on her mind. I just stood there like prey. “You poor thing!” she cooed as she touched my arms, “You seem freezing!”
It was cold but I was frozen for other reasons. Then, as if she was done with any pretending, Shelly hummed and said, “Let me warm you up.” I wondered, later, if the whole cold-apartment thing was part of her plan.
She embraced me and planted her lips on mine. If my heart wasn’t racing before, it began at that moment. My hands stuttered in their progress, sure they were supposed to do something, unsure of what. My lips moved, I guessed, in the sort of way a girl would expect. Heck, it had been years. I told myself I’d explain I was out of practice and tried to get my head in the moment.
Just when I thought I was letting myself enjoy the kissing, I felt Shelly’s hand as it slid down the front of my pants with the kind of practiced ease I have when I open the refrigerator. Before I could freak out and try to offer some kind of apology, my seductress hummed with approval. It seemed I wouldn’t have to apologize for my small size, Shelly didn’t mind.
If things had been moving fast, they went into hyperdrive once Shelly had found my cock. With a little playing, it shrugged off any nervous signals sent from my brain and began pulsing its way to an erection. Shelly knelt and had my pants off with suspicious speed. If I had cared (I didn’t), I might have paused and fretted over the fact that she’d obviously brought me home with single intent.
Pants off, I looked on as Shelly easily made my entire organ disappear. She hummed as she sucked and all I could see was her hair so I reached down and started to gather it away from her face, guessing that was the chivalrous thing to do.
A few bobs of her head and Shelly backed off to expose a bright pink, eager and fully hard cock. Big or not, my erection was stiff and ready.
Maybe too ready because I could see cum glistening as a little came forth as if about to boil over. “Eh-eh-eh,” my professional lover teased, “Not quite yet.”
She led me to her couch and had me lie down flat. “I don’t know if I can last…” I began to say, worried that I’d come the moment she got on me.
Her confidence was soothing while still erotic. “You’re going to be just perfect,” she told me. She spun her hair to one side and moved down to get her mouth back on me. I was about to object, to tell her I was more than ready but then I realized I was… mmm… I was…
I was getting my first blowjob.
Different but Better
Shelly’s soft lips wrapped around me with a tender softness that, when coupled with her sucking, was just the right about of pressure to make it, not only my first blowjob but, I was sure at the time, the best anyone ever had. Yeah, she knew what she was doing, alright.
I knew that guys were supposed to last a long time when they were fucking but I was pretty sure that rule didn’t apply to blowjobs. Or maybe it did, I really didn’t know. Anyway, I just couldn’t.
Shelly’s head bobbed a few more times and I just let go. “Ahhhhhhhhhhh!” I wailed. My legs kicked and tingled. I couldn’t feel my hands and my lips quivered as my body pulsed fluid into Shelly’s expert mouth.
While I whined and flailed, Shelly just hummed smoothly and calmly like a cook tasting something in the kitchen that’s turning out exactly as planned. One long hum and then she smoothly pulled those sucking lips up my cock and off of it.
That was it. At 8:22 on August the third, my life changed forever. I remember the time because I glanced to my left worried that the orgasm had left me without an ability to focus my eyes. I glimpsed the clock just before Shelly came into view and kissed me.
That kiss…
It was no ordinary kiss, I knew that much. Shelly’s lip pressed onto mine with a suggestion to open. As I did, hers opened as well. She took one of my hands in hers and brought it back over my head as the event began.
Warmth. Salty-sweet warmth.
Cum began entering me from Shelly’s mouth. And not just a little, Shelly’s kiss was full and her cum-laden tongue joined the effort delivering ever-more sweetness with the kind of intent efficiency that you’d expect from someone who was determined to ensure I had the fullest experience.
The sensation was complex and powerful. Just as my emotions grasped the pleasure of the sticky sensation on my lips, the warm cum was arriving on my tongue, leaving me unprepared for the onslaught of erotic delight that could accompany its one-of-a-kind taste.
Shelly hummed approval for my delight. The hand that held mine squeezed and I squealed a little as that woman turned me onto a world I didn’t know existed. As my tongue began to bathe in the fluid, Shelly delivered still more, so much I felt the need to swallow but didn’t dare as if I knew my journey would come to an end.
I hummed again at the experience. It felt like cinnamon roll icing that had been out of the oven for a while but instead of it just being sweet, it was salty—yet not like any other salty snacks I’ve had before. No, it wasn’t like anything I’d had before.
It occurred to me that I wasn’t just enjoying the cum itself. No, it was the whole act, the very sexual act of taking cum into my mouth. With a bit of reluctance, I swallowed. Shelly was looking down at me, obviously pleased but not just happy, she seemed sexually satisfied. With her gaze on me, I felt her fingers on my softening cock. She turned to watch her hand as she held the shaft then looked back at me and asked with one word: “More?”
I feebly answered, “Uh-huh,” unable to form any actual words. Using her finger, Shelly coated my waiting mouth with the last of my cum then offered her finger which I took into my mouth. I closed my lips around it to suckle and relish the last of the moment. Shelly released my hand and stroked my hair. With my now-freed hand, I held hers as I sucked on the finger at its end.
“Mmm, Jimmy,” she cooed, “better than I could have hoped for.”
That would be the extend of my evening of sex with Shelly. In fact, that would be the limit of the kind of sex I would have with her, ever. Shelly didn’t mean to open a door to a new world for me. She had no intent to see me in a dress, no intent to turn me into Olivia and, that night, certainly no idea she would create a slut. She was just a kinky girl who wanted to snowball a guy. She wanted me to like cum, that’s all. She had no idea what she had started.
As for me, lying on her couch feeling more satisfied than any person had a right to feel, I was in complete bliss. I didn’t have any thought about getting another snowball blowjob from Shelly again – I didn’t have any thoughts at all.
Shelly left to get a glass of water for me, joking that she didn’t want me to pass out. It felt only partly like a joke, I worried a little when I tried to get up but couldn’t. She just chuckled and called me cute.
“I thought you might like that,” she said as she returned. My head had stopped spinning and I could see the glass on the coffee table. Shelly had taken a seat across from me and something told me we were done for the night. I suddenly felt awkward in my half-naked state so I eased myself up and reached for my pants.
“I never…” I managed to say in response to her guess about what she had just done to me.
“Really?” she asked, seeming actually surprised, “First snowball?”
I oriented my pants to put them on. Shelly didn’t seem to mind that they were on her floor but I felt weird with her fully dressed and acting so casual.
“Uh-huh,” I told her, “Do most guys do that?”
Immediately after asking, I thought I must have sounded like a naïve little boy. Shelly, though, just answered with a tone like this was a magazine interview or something, telling me, “Not really, especially the big macho ones. It’s like they think they’re too manly or some shit. They let their egos get in the way.” She seemed reflective and then really angry as she went on, “One guy actually dumped me for trying. Can you believe that?!!! What a complete asshole, right?”
Wow, Shelly had an angry side. I must have looked scared.
She calmed, “Oh, not you, though. You just let yourself enjoy it, right?”
She may have meant those words to be complimentary but they made me feel meek and small all over again. I must have let on that my ego was crumpled as I tried to get my pants but because Shelly spoke as if trying to rescue me. “Don’t get the wrong idea, Jimmy!” she said with the urgency of someone who needed to stop a suicide. I wasn’t feeling that bad but she went on, “You’re super-cute with your long hair and don’t get me started on those eyes…”
Not a bad choice of words to talk me off the ledge. I relaxed a bit and started on my fly but fell back onto the couch. “Sorry, give me a minute,” I told her. I needed my head to clear a bit more. She would never know how intense my reaction was that night.
Now Shelly started to seem a little bashful. But only a little as she explained, “It’s just that I really like doing that. Like I R-E-A-L-L-Y like it and have been in the mood for it for weeks. When my friend told me about the guys she worked with, she mentioned you and I thought…”
It made me smile to learn she’d sought me out. Shelly was special, that much was obvious, and I was flattered to think she wanted anything to do with me – or to do anything with me – or to me.
She asked for my number and put it into her phone then Shelly stood and reached for me. The gesture was the same one as when we arrived at her place but it felt completely different when I took her hand. “I gotta get up early. You can get a ride, right?” she said as we walked to her door, “You around this weekend?”
Did I know, when I stood outside as she locked her door that I’d be back two nights later, experiencing the bliss of swallowing my cum while back on her couch?
Maybe.
Did I know that Shelly had opened a door to sexual pleasure that would drive my needs?
Maybe, though I would have guessed it was a phase.
Did I have any idea how far this would go?
No. Definitely no.
I knew that guys were supposed to last a long time when they were fucking but I was pretty sure that rule didn’t apply to blowjobs. Or maybe it did, I really didn’t know. Anyway, I just couldn’t.
Shelly’s head bobbed a few more times and I just let go. “Ahhhhhhhhhhh!” I wailed. My legs kicked and tingled. I couldn’t feel my hands and my lips quivered as my body pulsed fluid into Shelly’s expert mouth.
While I whined and flailed, Shelly just hummed smoothly and calmly like a cook tasting something in the kitchen that’s turning out exactly as planned. One long hum and then she smoothly pulled those sucking lips up my cock and off of it.
That was it. At 8:22 on August the third, my life changed forever. I remember the time because I glanced to my left worried that the orgasm had left me without an ability to focus my eyes. I glimpsed the clock just before Shelly came into view and kissed me.
That kiss…
It was no ordinary kiss, I knew that much. Shelly’s lip pressed onto mine with a suggestion to open. As I did, hers opened as well. She took one of my hands in hers and brought it back over my head as the event began.
Warmth. Salty-sweet warmth.
Cum began entering me from Shelly’s mouth. And not just a little, Shelly’s kiss was full and her cum-laden tongue joined the effort delivering ever-more sweetness with the kind of intent efficiency that you’d expect from someone who was determined to ensure I had the fullest experience.
The sensation was complex and powerful. Just as my emotions grasped the pleasure of the sticky sensation on my lips, the warm cum was arriving on my tongue, leaving me unprepared for the onslaught of erotic delight that could accompany its one-of-a-kind taste.
Shelly hummed approval for my delight. The hand that held mine squeezed and I squealed a little as that woman turned me onto a world I didn’t know existed. As my tongue began to bathe in the fluid, Shelly delivered still more, so much I felt the need to swallow but didn’t dare as if I knew my journey would come to an end.
I hummed again at the experience. It felt like cinnamon roll icing that had been out of the oven for a while but instead of it just being sweet, it was salty—yet not like any other salty snacks I’ve had before. No, it wasn’t like anything I’d had before.
It occurred to me that I wasn’t just enjoying the cum itself. No, it was the whole act, the very sexual act of taking cum into my mouth. With a bit of reluctance, I swallowed. Shelly was looking down at me, obviously pleased but not just happy, she seemed sexually satisfied. With her gaze on me, I felt her fingers on my softening cock. She turned to watch her hand as she held the shaft then looked back at me and asked with one word: “More?”
I feebly answered, “Uh-huh,” unable to form any actual words. Using her finger, Shelly coated my waiting mouth with the last of my cum then offered her finger which I took into my mouth. I closed my lips around it to suckle and relish the last of the moment. Shelly released my hand and stroked my hair. With my now-freed hand, I held hers as I sucked on the finger at its end.
“Mmm, Jimmy,” she cooed, “better than I could have hoped for.”
That would be the extend of my evening of sex with Shelly. In fact, that would be the limit of the kind of sex I would have with her, ever. Shelly didn’t mean to open a door to a new world for me. She had no intent to see me in a dress, no intent to turn me into Olivia and, that night, certainly no idea she would create a slut. She was just a kinky girl who wanted to snowball a guy. She wanted me to like cum, that’s all. She had no idea what she had started.
As for me, lying on her couch feeling more satisfied than any person had a right to feel, I was in complete bliss. I didn’t have any thought about getting another snowball blowjob from Shelly again – I didn’t have any thoughts at all.
Shelly left to get a glass of water for me, joking that she didn’t want me to pass out. It felt only partly like a joke, I worried a little when I tried to get up but couldn’t. She just chuckled and called me cute.
“I thought you might like that,” she said as she returned. My head had stopped spinning and I could see the glass on the coffee table. Shelly had taken a seat across from me and something told me we were done for the night. I suddenly felt awkward in my half-naked state so I eased myself up and reached for my pants.
“I never…” I managed to say in response to her guess about what she had just done to me.
“Really?” she asked, seeming actually surprised, “First snowball?”
I oriented my pants to put them on. Shelly didn’t seem to mind that they were on her floor but I felt weird with her fully dressed and acting so casual.
“Uh-huh,” I told her, “Do most guys do that?”
Immediately after asking, I thought I must have sounded like a naïve little boy. Shelly, though, just answered with a tone like this was a magazine interview or something, telling me, “Not really, especially the big macho ones. It’s like they think they’re too manly or some shit. They let their egos get in the way.” She seemed reflective and then really angry as she went on, “One guy actually dumped me for trying. Can you believe that?!!! What a complete asshole, right?”
Wow, Shelly had an angry side. I must have looked scared.
She calmed, “Oh, not you, though. You just let yourself enjoy it, right?”
She may have meant those words to be complimentary but they made me feel meek and small all over again. I must have let on that my ego was crumpled as I tried to get my pants but because Shelly spoke as if trying to rescue me. “Don’t get the wrong idea, Jimmy!” she said with the urgency of someone who needed to stop a suicide. I wasn’t feeling that bad but she went on, “You’re super-cute with your long hair and don’t get me started on those eyes…”
Not a bad choice of words to talk me off the ledge. I relaxed a bit and started on my fly but fell back onto the couch. “Sorry, give me a minute,” I told her. I needed my head to clear a bit more. She would never know how intense my reaction was that night.
Now Shelly started to seem a little bashful. But only a little as she explained, “It’s just that I really like doing that. Like I R-E-A-L-L-Y like it and have been in the mood for it for weeks. When my friend told me about the guys she worked with, she mentioned you and I thought…”
It made me smile to learn she’d sought me out. Shelly was special, that much was obvious, and I was flattered to think she wanted anything to do with me – or to do anything with me – or to me.
She asked for my number and put it into her phone then Shelly stood and reached for me. The gesture was the same one as when we arrived at her place but it felt completely different when I took her hand. “I gotta get up early. You can get a ride, right?” she said as we walked to her door, “You around this weekend?”
Did I know, when I stood outside as she locked her door that I’d be back two nights later, experiencing the bliss of swallowing my cum while back on her couch?
Maybe.
Did I know that Shelly had opened a door to sexual pleasure that would drive my needs?
Maybe, though I would have guessed it was a phase.
Did I have any idea how far this would go?
No. Definitely no.
More of the Same and then Something Different
Shelly didn’t wait long before inviting me to come over again. “We can go out, you know, see a movie or whatever,” I had said in response.
“I know exactly what I want, Jimmy,” was her reply, “See you around eight?”
Shelly, hands-down the most beautiful, sexy girl I’d even been around was asking for a second date. The guys from the office who, frankly, never talked to me, were absolutely incredulous on Friday, stopping by my desk and asking for details. The one who I did consider a friend, a new guy named Ted, heard the news and was equally curious. “I heard you got picked up at group happy hour!” he joked, “Now I’m sorry I was stuck here working late.”
I didn’t have much of a reply to any of them. I sure as hell wasn’t going to tell them what happened in Shelly’s apartment and I was sure we didn’t have a future. Shelly was just too much for me – too pretty, too successful, too everything. I was no fool. Instead of taking my chance for a little fame among my coworkers, I’d just let it die and quickly return to cubicle obscurity where I was most comfortable.
The funny thing was that when she called me for a second date, all I could think about was the erotic bliss of cum in my mouth. That texture, that one-of-a-kind texture haunted me. When I got home after being with her, my body temperature was still elevated and I fell asleep with my blanket tossed to the side. Shelly, the out-of-my-league girl who showed an interest in me, didn’t seem to matter.
The fact that I wasn’t thinking about the girl should have told me something.
Eight o’clock seemed like a late hour to start a date but I knew I’d sound like a loser to suggest we meet earlier. I just agreed and showed up expecting, well, I wasn’t sure, but I actually expected a regular date. “So, you wanna go out somewhere?” I asked once I was in her living room.
She chuckled as if I was being ridiculous. “C’mere,” she smoothly commanded with a finger reeling me in. Who was I to object?
About fifteen minutes after that, my world was simultaneously on fire and hazily numb as I lay on her couch with warm cum running past my lips. I couldn’t say if it was better or different or… no, not worse, definitely not worse, than the first time but… good god it was amazing. As I got close, Shelly had produced a shotglass. Her voice oozing with sex, she had told me, “Finish yourself into it.” From my body to the glass and back to my body. Taking my cum into my mouth was just as hot as the first time.
Then, just as before, Shelly sat across from me. This time sipping some kind of alcoholic drink and calmly telling me, “You know, I like that you’re small. It’s hot to take you all the way in and, Jimmy, I love that you get off so fast.”
We had progressed, if that’s the right word, from interview to report card but Shelly was calm and easy going as usual. I was too euphoric to be calm but I did manage to get my pants on without falling. Once it was clear I could stand without being wobbly, Shelly casually said, “I’m so glad you came by,” ending our date. The clock I had noticed before said 8:28. Twenty-eight minute date; I’d think about that on the drive home since I didn’t want to look uncool.
“Right… thanks for inviting me,” I said, stammering a bit.
“How’s Tuesday?” she asked as she opened her door, “I can come by your place if that works.”
Of course there was only one answer. “Sure,” I said, adding, “Dinner?”
“Mmm, I don’t think I can. How’s, like eight or so, like tonight?” she replied.
“Like tonight” was the obvious part of that. “Like tonight” as in, “We’re just getting together for sex.” For the best sex anyone has ever known, as far as I was concerned. So, I replied, “Sure, let’s make it eight,” and then added, “like tonight,” so she would know how cool I was.
The memory of our two nights together and anticipation for our next connection preoccupied my thoughts every day. Once alone and in bed at night, I started to reach my hand down beneath the sheets but stopped. No, there was something special going on and I didn’t want to bastardize the experience by going solo. Instead, I just let my mind try to recreate the magic, to feel some of the erotic bliss that the memory would provide.
She showed up with her shotglass Tuesday at my place and that was followed by Friday at hers, the following Saturday at mine, then Wednesday at hers and so on. By the time October came, we had had been together a dozen times, the only one that lasted over a half-hour being the time she lost her car keys at my place and we spent five minutes looking for them.
I, of course, was not complaining and not just because I wanted to be cool. No, I wasn’t complaining because there was nothing to complain about. This girl was taking me to an impossible world of sexual bliss night after night. And this was all her idea; I felt no guilt, no strings attached, no need for any sort of reciprocity. It was perfect, just perfect and, frankly couldn’t get any better.
Couldn’t get any better.
Couldn’t get any better.
Until it did.
It happened at her apartment. I don’t know the exact time and, no, it wasn’t at 8:22 but it was close to that time. Shelly had me on her couch but still clothed. That had me wondering since she had a working formula: kiss a little, feel me, kneel, undress, get me hard, lay me down, suck a little, watch me finish, then take me wonderland.
I was lying there with my clothes on when she excused herself and bolted to the kitchen. I heard some beeping that sounded like her microwave and she returned.
Her voice oozed sex, like hot, dirty, amazing sex. “I have something for you,” she told me.
We’d been kissing (her step one) and I was turned on, already whining with anticipation but perplexed with her change in the program. “What is it?” I asked.
Her fingers wrapped around the shotglass that she produced from behind her back. “Open up,” she said softly.
Though brief, we had shared a dozen deeply intimate encounters. We hadn’t talked much but… what we had shared… mmm. In addition to being deeply satisfying, our evenings also built trust so I didn’t ask.
Shelly dipped her finger into the glass and brought it to my lips. I didn’t know and didn’t ask. I trusted her. We had shared a deeply erotic sexual relationship and I was ready for whatever she wanted.
Shelly hummed and I lay there, my lips slightly open, ready.
She moved slowly and I just waited, still and ready.
With her soft hum setting the mood, her finger delicately made contact with my lower lip. Sticky and wet, it touched me.
It didn’t happen at once. Shelly had time to drag her laden finger across my lower lip as it happened. And when it did, I was not ready.
“Oh GOD!” I called out when I realized. “It’s cum!”
I must have moved too much, must have startled her. Shelly withdrew. “Jimmy,” she said in a near-panic, “You almost dumped it on my couch!”
Different Doesn't Mean Bad
Realizing I’d over-reacted, I tried to settle. “Sorry,” I answered, “I mean, I wasn’t expecting, I mean, I didn’t know… what is.. who…”
“It’s from my girlfriend’s guy,” she explained, “I didn’t tell her about you, I told her I was into it.”
As if I cared about her friend or how she got it. “Can I…” I began.
The expression on Shelly’s face was utter delight. Looking at me as if she’d just guessed the word in Final Jeopardy, she said, “Oh, yes. Yes you can,” and dipped her finger back into the glass.
The next delivery arrived without the uncertainty. When Shelly first put another guy’s cum on my lips I was expecting some kind of drink she had made as if I needed one to get into the mood. The second time, knowing what it was, I just offered my soft mouth and let her paint my lips like she’d done so many times before. Say one thing for Shelly, she never wasted a drop from that glass. That night would be no different.
Only it wasn’t like before because now it was someone else’s cum. Suddenly, it was as if my own cum was the generic and this was the real thing. As if mine was for amateurs and this was for pros. Whatever the comparison, tasting something that didn’t come from me took the whole experience to a new level.
I filled her apartment with a loud whine and when she asked I wanted more, I echoed, “More!” leaving no doubt.
“Better than your own?” she asked.
I gasped, “So much better…”
She painted my lower lip a again.
“More!” I cried.
Shelly brought over the shotglass and I remember the moment because I now know what it did to me. As she held the glass to my lips, Shelly looked into my eyes with a bit of uncertainty, as if asking the question. Of course, she couldn’t have known what laid ahead, but it was as if she was saying, “If you drink this, you will never be a man again. Are you sure?”
I gave a little nod and a whimper. I wanted it so badly.
We never would have the conversation, Shelly wasn’t much for talking. I’d have to think about that moment alone. Looking back at it, that act, the moment spoonfuls of warm cum from another man entered my mouth, was the turning point.
Shelly seemed as surprised as I was with my agreeable gesture. She sought to amplify it. “You want his cum?” she teased.
“So badly…” I could barely speak but my whiney tone was enough for her to understand.
More teasing followed. “Tell me, then. Tell me you want his cum.”
Begging had never been my thing and I wasn’t really in the mood to start but I was in the mood for more. “Yes, please,” I whined, “I want his cum. Feed it to me!”
Nope. I was wrong. Begging was my thing and it was getting me even more turned on. “P-l-e-a-s-e!” I pleaded.
I felt Shelly’s hand slide under my head. She grabbed a handful of my hair, pulling just enough for me to feel wanted before she poured the man’s cream into me. I whined as it entered. The texture was a little off and it had cooled too much but that man’s luxurious cum flowed into my mouth, into my soul and gave me a level of sexual pleasure that would drive my every decision from that moment on.
“More!” I gasped after I swallowed his essence. I felt a fulfillment with a person I hadn’t even met, a connection so deep it made me cry. I reeled in the sensation and would have traded my car for second glassful. Licking my lips as I waited, I felt my chest heaving with heavy breaths and enough heat to defeat the icy temperature of the room.
Shelly did her best, rolling her finger around the inside rim and letting me suck on it as she stroked my hair. “Oh, Jimmy…” she said softly, the sound of erotic satisfaction that told me she had enjoyed the experience as much as I had.
Before I settled down, though, Shelly asked, “Are you alright? I mean, you’re horny now, aren’t you?”
Still breathing erratically, I tried to tell her I was. Shelly understood and slid her hand down my pants either to make sure or to get started. Either way, she soon had my pants down to my knees and my erection refilling the glass.
I took the second load, my own, with pleasure not as marked as the first, but still wonderful.
With a clearer head, I thought about my time with Shelly the next day. Sure, my own cum was served up warm and with that unique mouthfeel but there was something about what she had in that shotglass – it wasn’t that it tasted better, per se (though it did), it was because it wasn’t me. This was real sex - real, hot intimacy with someone else. It wasn’t any sort of masturbation and that’s why I had reacted the way I did. I was finally having an intense sexual experience that wasn’t about me. All I could think about was that taste and the way cum in my mouth made me feel.
After two more nights of the same, Shelly presented me with a gift, “Your special cup,” she said as I opened the shotglass with “cum shot” written on it.
After using it the first time on a Saturday night, Shelly asked if I was free on Thursday of that week. “Do we need to wait that long?” was my reply. She smiled at me and I smiled back as if my growing addiction would never become a problem.
“It’s from my girlfriend’s guy,” she explained, “I didn’t tell her about you, I told her I was into it.”
As if I cared about her friend or how she got it. “Can I…” I began.
The expression on Shelly’s face was utter delight. Looking at me as if she’d just guessed the word in Final Jeopardy, she said, “Oh, yes. Yes you can,” and dipped her finger back into the glass.
The next delivery arrived without the uncertainty. When Shelly first put another guy’s cum on my lips I was expecting some kind of drink she had made as if I needed one to get into the mood. The second time, knowing what it was, I just offered my soft mouth and let her paint my lips like she’d done so many times before. Say one thing for Shelly, she never wasted a drop from that glass. That night would be no different.
Only it wasn’t like before because now it was someone else’s cum. Suddenly, it was as if my own cum was the generic and this was the real thing. As if mine was for amateurs and this was for pros. Whatever the comparison, tasting something that didn’t come from me took the whole experience to a new level.
I filled her apartment with a loud whine and when she asked I wanted more, I echoed, “More!” leaving no doubt.
“Better than your own?” she asked.
I gasped, “So much better…”
She painted my lower lip a again.
“More!” I cried.
Shelly brought over the shotglass and I remember the moment because I now know what it did to me. As she held the glass to my lips, Shelly looked into my eyes with a bit of uncertainty, as if asking the question. Of course, she couldn’t have known what laid ahead, but it was as if she was saying, “If you drink this, you will never be a man again. Are you sure?”
I gave a little nod and a whimper. I wanted it so badly.
We never would have the conversation, Shelly wasn’t much for talking. I’d have to think about that moment alone. Looking back at it, that act, the moment spoonfuls of warm cum from another man entered my mouth, was the turning point.
Shelly seemed as surprised as I was with my agreeable gesture. She sought to amplify it. “You want his cum?” she teased.
“So badly…” I could barely speak but my whiney tone was enough for her to understand.
More teasing followed. “Tell me, then. Tell me you want his cum.”
Begging had never been my thing and I wasn’t really in the mood to start but I was in the mood for more. “Yes, please,” I whined, “I want his cum. Feed it to me!”
Nope. I was wrong. Begging was my thing and it was getting me even more turned on. “P-l-e-a-s-e!” I pleaded.
I felt Shelly’s hand slide under my head. She grabbed a handful of my hair, pulling just enough for me to feel wanted before she poured the man’s cream into me. I whined as it entered. The texture was a little off and it had cooled too much but that man’s luxurious cum flowed into my mouth, into my soul and gave me a level of sexual pleasure that would drive my every decision from that moment on.
“More!” I gasped after I swallowed his essence. I felt a fulfillment with a person I hadn’t even met, a connection so deep it made me cry. I reeled in the sensation and would have traded my car for second glassful. Licking my lips as I waited, I felt my chest heaving with heavy breaths and enough heat to defeat the icy temperature of the room.
Shelly did her best, rolling her finger around the inside rim and letting me suck on it as she stroked my hair. “Oh, Jimmy…” she said softly, the sound of erotic satisfaction that told me she had enjoyed the experience as much as I had.
Before I settled down, though, Shelly asked, “Are you alright? I mean, you’re horny now, aren’t you?”
Still breathing erratically, I tried to tell her I was. Shelly understood and slid her hand down my pants either to make sure or to get started. Either way, she soon had my pants down to my knees and my erection refilling the glass.
I took the second load, my own, with pleasure not as marked as the first, but still wonderful.
With a clearer head, I thought about my time with Shelly the next day. Sure, my own cum was served up warm and with that unique mouthfeel but there was something about what she had in that shotglass – it wasn’t that it tasted better, per se (though it did), it was because it wasn’t me. This was real sex - real, hot intimacy with someone else. It wasn’t any sort of masturbation and that’s why I had reacted the way I did. I was finally having an intense sexual experience that wasn’t about me. All I could think about was that taste and the way cum in my mouth made me feel.
After two more nights of the same, Shelly presented me with a gift, “Your special cup,” she said as I opened the shotglass with “cum shot” written on it.
After using it the first time on a Saturday night, Shelly asked if I was free on Thursday of that week. “Do we need to wait that long?” was my reply. She smiled at me and I smiled back as if my growing addiction would never become a problem.
Supply Issues
After enjoying the cum shotglass on our next night, Shelly disappointed me when we got together a few nights later. “Sorry, Jimmy,” she told me as she came into my place, “I didn’t bring your glass.”
“I’ve got glasses,” I answered.
She smiled. “No, silly, I don’t have anything to put in it.”
“No cum?”
“Sorry. It’s not like I can just stop at the 7-11, you know.”
I thought I must have sounded petulant or ungrateful. “I’m sorry, Shel, I don’t want you to think…”
“It’s alright, Jimmy, I know what you mean. You okay if it’s just us tonight?”
It was an awkward moment because I paused before answering. Then, before I could say anything, I felt bad about pausing, like I was insulting her. There were times, usually in the mornings after our get-togethers, that I’d feel a pang of guilt. I was letting Shelly believe that we were in a relationship. My true love was served up on that little cup, not the girl who served it. Still, Shelly and I were intimate in our own way and she sure did seem to be satisfied… On the days I would have doubts, they dissipated by lunchtime and I’d be back to fantasizing about the next time I would be taken to bliss.
She nodded as if disappointed and I felt I’d let her down somehow. “It’s okay, Jimmy, I understand,” she told me.
I needed to rally, I needed to tell her that we had our thing and it was great and we didn’t need anyone else.
Only I didn’t. I guess I couldn’t.
“Lemme see what I can do,” was all she said before turning away, “I’ll get back to you.”
It was a reminder that I was in the hands of a cool, polished professional. It also felt comforting to know Shelly was on the case because I knew she would take care of it, that she would take care of me.
There are people in our lives who we come to respect and count on. Sometimes, those people let us down. Sometimes, our heroes remind us why they deserve our respect.
An hour after Shelly left my place, she messaged me. “I found a guy if you want to try something different,” she told me.
“Different,” she explained, would mean that we’d go to this guy’s house. He wasn’t going to jerk off into a container because he was worried Shelly was going to take it to a sperm donor lab or some crazy chick would impregnate herself and sue him.
“People can be awful,” I said in agreement.
Instead, he agreed to let Shelly take his load and that I could be right there. “It means you’ll be watching me with another guy,” she explained, “I don’t want that to bother you but maybe you like the idea?”
I skimmed right past the idea that she was asking permission to be with another guy. Later I would guess that Shelly had apparently come to see us as exclusive. It was then that I began thinking of her as my girlfriend. I ignored another important signal about what was happening to me. Not only didn’t I react to Shelly thinking we were getting serious but I didn’t give a second thought to the notion of her mouth on another guy. Shelly would be my girlfriend because it seemed I had become her boyfriend, not because I necessarily liked her. I didn’t doubt that she was satisfied with what we had and I sure wasn’t going to do anything to jeopardize it.
“Sounds kinky and hot,” I replied, “I mean, if you want to.” I just wanted another man’s cum so badly that part of me didn’t care if I had to watch her with another guy. Oh, who am I kidding, all of me would have gladly let her whore around if it meant some cum for me. I really needed it.
“Did he say when?” I asked, hoping not to sound too eager to get my girlfriend out to please another man.
“Well,” Shelly answered, “I was just talking to him and he’s ready to go right now. Should we get over there before he changes his mind?”
I didn’t hesitate. Shelly picked me up and we were at Don’s door within the hour. Looking over at her as we drove, I couldn’t help but noticed how she was dressed. Leather pants and a snug top and no sneakers. She was always in simple jeans and sweatshirt on our dates. “You look nice,” I commented, “Reminds me a little of the night we met.”
She clearly didn’t like dressing that way. She snarled a little. “Guys… it’s what they need, you know.”
Guys… like the one who was going to cum in Shelly’s mouth for me. I let myself feel the anticipation.
Once he answered, though, my mood changed completely. I felt like some kind of cuckold, delivering my girlfriend for a kinky evening. I felt like a third wheel, a needless appendage at this man’s doorstep. I felt like a leech, someone just there to take the product of their labors without giving anything in return.
Our host, Don, only had eyes for Shelly. He purposefully avoided eye contact with me and never acknowledged me. Thank god for that. Being invisible made entering his house much more barrable.
Shelly and Don exchanged a few words. For god’s sake, I thought, they’re talking about the weather? I looked around but stayed close to Shelly. It seemed like an eternity before they were kissing. I was sure that was just me; it was probably like Shelly and me when we first got together. Shelly got on her knees, leaving only me at eye level with Don. That was too weird so I kneeled near her. I moved a bit trying to find the right spot that gave the couple privacy but still suggested Shelly and I were together. It was weird, to be sure. I wondered if I should have done some research, like reading up on social norms for that kind of thing but I was pretty sure we had gone far from any mainstream sort of encounter.
I tried to distance myself mentally, if not physically, from the huge thing that Shelly was working with her hands. She used her index finger and thumb on me – with Don she used a whole hand, bracing with her other hand on the base of it. It might have been average but, kneeling not far from it, Don’s cock was intimidatingly massive.
Say one thing about my girl, though, that Shelly knows how to please. Don was older than us, maybe late-thirties. I would have guessed he’d had plenty of girls but he was soon oohing and aahing and telling Shelly she was the best. I have no reason to think he lied.
Don’s vocalizations were the first clue but Shelly knows when a guy’s about to come.
“Do you want his cum?” she asked and I gave her the same answer I always did. She reached for me and pulled me close as soon as she had my hand. I was still on the ground as Don wailed and let go. Shelly pumped him with one hand while pressing down on my shoulder with the other, forcing me to the ground. I hadn’t thought about it but she wasn’t going to let me up. That girl was undoubtedly in charge of the moment for all in the room.
Just as Don’s hands eased their grip on my girlfriend’s head, Shelly came off the thick cock. She easily spun and her head approached.
Now, of course, I knew what was in store.
I had agreed to do this. I wanted to. I had gotten in my girlfriend’s car because we were going to this guy’s house so that she would blow him and I would get his cum.
I had knelt by her and didn’t try to get up when I ended up on my back next to Shelly. I stayed there and watched a man I’d never met before cum in her mouth. I stayed there as she held me and came close.
Even though I’d caused all this to happen, in that moment, it felt wrong. What the hell was I doing in this guy’s house? What kind of boyfriend am I? What’s this guy going to think of me? What would…
Shelly’s thumb pressed down on my chin suggestively and I wasted no time opening like a bucket loader and letting it all happen.
The doubts didn’t just stop, they were erased like childish fears. In their place was the decadent feeling of love liquor that made my body tingle and relaxed every anxious muscle. Shelly heard the expected whine and let go of my hair, knowing I was certainly not going to put up a fight. She touched my face and pushed with her tongue until I had it all.
Then, instead of her typical lingering, my girlfriend left me to enjoy the moment before swallowing. I didn’t care that I was lying vulnerable in some anonymous older guy’s living room, I just looked at the out-of-focus ceiling and enjoyed the moment that connected me with another being by swallowing him.
Shelly, though, was about to prove she was the best girlfriend ever because she’d gone back to Don for the last drops. She leaned over me, her face a foot or so from mine. I opened up and Shelly let the last of Don’s cum slowly drizzle out. I tingled with anticipation and love as it fell and accepted it as the completion of an erotic act that managed to top everything else I had known since Shelly first showed me how wonderful sex could be.
When I was ready to rejoin the world, only Shelly was in it. “He said to let ourselves out,” Shelly told me, “Can you walk?”
I was wildly turned on and she must have seen that need in my eyes. Shelly took a knee next to me and softly said, “Baby, I don’t think Don wants us sticking around and letting you jerk off in his house wasn’t part of the deal. I’m sorry, but we should just go.”
I took a deep breath. I needed to get off but she was right. I gave her my hushed agreement.
She had that fun smile, the sincere one that always appeared after sex. She helped me up and reminded me, “I love how you get afterwards – so helpless and out of control.”
In her car, she asked, “Well?”
“Oh god, Shell…” I answered, “I mean… can we do that again?”
“You,” she replied with purpose, “are turning out to be more fun than I would have guessed.”
“I’ve got glasses,” I answered.
She smiled. “No, silly, I don’t have anything to put in it.”
“No cum?”
“Sorry. It’s not like I can just stop at the 7-11, you know.”
I thought I must have sounded petulant or ungrateful. “I’m sorry, Shel, I don’t want you to think…”
“It’s alright, Jimmy, I know what you mean. You okay if it’s just us tonight?”
It was an awkward moment because I paused before answering. Then, before I could say anything, I felt bad about pausing, like I was insulting her. There were times, usually in the mornings after our get-togethers, that I’d feel a pang of guilt. I was letting Shelly believe that we were in a relationship. My true love was served up on that little cup, not the girl who served it. Still, Shelly and I were intimate in our own way and she sure did seem to be satisfied… On the days I would have doubts, they dissipated by lunchtime and I’d be back to fantasizing about the next time I would be taken to bliss.
She nodded as if disappointed and I felt I’d let her down somehow. “It’s okay, Jimmy, I understand,” she told me.
I needed to rally, I needed to tell her that we had our thing and it was great and we didn’t need anyone else.
Only I didn’t. I guess I couldn’t.
“Lemme see what I can do,” was all she said before turning away, “I’ll get back to you.”
It was a reminder that I was in the hands of a cool, polished professional. It also felt comforting to know Shelly was on the case because I knew she would take care of it, that she would take care of me.
There are people in our lives who we come to respect and count on. Sometimes, those people let us down. Sometimes, our heroes remind us why they deserve our respect.
An hour after Shelly left my place, she messaged me. “I found a guy if you want to try something different,” she told me.
“Different,” she explained, would mean that we’d go to this guy’s house. He wasn’t going to jerk off into a container because he was worried Shelly was going to take it to a sperm donor lab or some crazy chick would impregnate herself and sue him.
“People can be awful,” I said in agreement.
Instead, he agreed to let Shelly take his load and that I could be right there. “It means you’ll be watching me with another guy,” she explained, “I don’t want that to bother you but maybe you like the idea?”
I skimmed right past the idea that she was asking permission to be with another guy. Later I would guess that Shelly had apparently come to see us as exclusive. It was then that I began thinking of her as my girlfriend. I ignored another important signal about what was happening to me. Not only didn’t I react to Shelly thinking we were getting serious but I didn’t give a second thought to the notion of her mouth on another guy. Shelly would be my girlfriend because it seemed I had become her boyfriend, not because I necessarily liked her. I didn’t doubt that she was satisfied with what we had and I sure wasn’t going to do anything to jeopardize it.
“Sounds kinky and hot,” I replied, “I mean, if you want to.” I just wanted another man’s cum so badly that part of me didn’t care if I had to watch her with another guy. Oh, who am I kidding, all of me would have gladly let her whore around if it meant some cum for me. I really needed it.
“Did he say when?” I asked, hoping not to sound too eager to get my girlfriend out to please another man.
“Well,” Shelly answered, “I was just talking to him and he’s ready to go right now. Should we get over there before he changes his mind?”
I didn’t hesitate. Shelly picked me up and we were at Don’s door within the hour. Looking over at her as we drove, I couldn’t help but noticed how she was dressed. Leather pants and a snug top and no sneakers. She was always in simple jeans and sweatshirt on our dates. “You look nice,” I commented, “Reminds me a little of the night we met.”
She clearly didn’t like dressing that way. She snarled a little. “Guys… it’s what they need, you know.”
Guys… like the one who was going to cum in Shelly’s mouth for me. I let myself feel the anticipation.
Once he answered, though, my mood changed completely. I felt like some kind of cuckold, delivering my girlfriend for a kinky evening. I felt like a third wheel, a needless appendage at this man’s doorstep. I felt like a leech, someone just there to take the product of their labors without giving anything in return.
Our host, Don, only had eyes for Shelly. He purposefully avoided eye contact with me and never acknowledged me. Thank god for that. Being invisible made entering his house much more barrable.
Shelly and Don exchanged a few words. For god’s sake, I thought, they’re talking about the weather? I looked around but stayed close to Shelly. It seemed like an eternity before they were kissing. I was sure that was just me; it was probably like Shelly and me when we first got together. Shelly got on her knees, leaving only me at eye level with Don. That was too weird so I kneeled near her. I moved a bit trying to find the right spot that gave the couple privacy but still suggested Shelly and I were together. It was weird, to be sure. I wondered if I should have done some research, like reading up on social norms for that kind of thing but I was pretty sure we had gone far from any mainstream sort of encounter.
I tried to distance myself mentally, if not physically, from the huge thing that Shelly was working with her hands. She used her index finger and thumb on me – with Don she used a whole hand, bracing with her other hand on the base of it. It might have been average but, kneeling not far from it, Don’s cock was intimidatingly massive.
Say one thing about my girl, though, that Shelly knows how to please. Don was older than us, maybe late-thirties. I would have guessed he’d had plenty of girls but he was soon oohing and aahing and telling Shelly she was the best. I have no reason to think he lied.
Don’s vocalizations were the first clue but Shelly knows when a guy’s about to come.
“Do you want his cum?” she asked and I gave her the same answer I always did. She reached for me and pulled me close as soon as she had my hand. I was still on the ground as Don wailed and let go. Shelly pumped him with one hand while pressing down on my shoulder with the other, forcing me to the ground. I hadn’t thought about it but she wasn’t going to let me up. That girl was undoubtedly in charge of the moment for all in the room.
Just as Don’s hands eased their grip on my girlfriend’s head, Shelly came off the thick cock. She easily spun and her head approached.
Now, of course, I knew what was in store.
I had agreed to do this. I wanted to. I had gotten in my girlfriend’s car because we were going to this guy’s house so that she would blow him and I would get his cum.
I had knelt by her and didn’t try to get up when I ended up on my back next to Shelly. I stayed there and watched a man I’d never met before cum in her mouth. I stayed there as she held me and came close.
Even though I’d caused all this to happen, in that moment, it felt wrong. What the hell was I doing in this guy’s house? What kind of boyfriend am I? What’s this guy going to think of me? What would…
Shelly’s thumb pressed down on my chin suggestively and I wasted no time opening like a bucket loader and letting it all happen.
The doubts didn’t just stop, they were erased like childish fears. In their place was the decadent feeling of love liquor that made my body tingle and relaxed every anxious muscle. Shelly heard the expected whine and let go of my hair, knowing I was certainly not going to put up a fight. She touched my face and pushed with her tongue until I had it all.
Then, instead of her typical lingering, my girlfriend left me to enjoy the moment before swallowing. I didn’t care that I was lying vulnerable in some anonymous older guy’s living room, I just looked at the out-of-focus ceiling and enjoyed the moment that connected me with another being by swallowing him.
Shelly, though, was about to prove she was the best girlfriend ever because she’d gone back to Don for the last drops. She leaned over me, her face a foot or so from mine. I opened up and Shelly let the last of Don’s cum slowly drizzle out. I tingled with anticipation and love as it fell and accepted it as the completion of an erotic act that managed to top everything else I had known since Shelly first showed me how wonderful sex could be.
When I was ready to rejoin the world, only Shelly was in it. “He said to let ourselves out,” Shelly told me, “Can you walk?”
I was wildly turned on and she must have seen that need in my eyes. Shelly took a knee next to me and softly said, “Baby, I don’t think Don wants us sticking around and letting you jerk off in his house wasn’t part of the deal. I’m sorry, but we should just go.”
I took a deep breath. I needed to get off but she was right. I gave her my hushed agreement.
She had that fun smile, the sincere one that always appeared after sex. She helped me up and reminded me, “I love how you get afterwards – so helpless and out of control.”
In her car, she asked, “Well?”
“Oh god, Shell…” I answered, “I mean… can we do that again?”
“You,” she replied with purpose, “are turning out to be more fun than I would have guessed.”
Lunch
I tried not to be a pest but I did ask her a few times over the following days if we could go back to Don’s, “Or some other guy, maybe?” I suggested; I wasn’t particular.
She didn’t reply to my ideas but her eventual answer was unnerving. Now, for most guys, it wouldn’t be a big deal if their girlfriend invited them to lunch but when Shelly suggested it, I freaked out.
We didn’t have a “go to lunch” relationship. I worried she was dumping me but somehow managed not to ask if she was. Instead, I just met her as agreed and tried not to act like I was worried my new world was coming to a premature ending.
She asked about my day and I guessed some kind of small talk was the right thing to do. Part of me wondered if, maybe, she didn’t have some grand announcement. Like, maybe we were going to have a normal relationship?
I felt the need to keep the conversation going.
I’m not good at that sort of thing so I just asked, “Is this snowballing something you’ve always been into?”
Of course, as soon as I asked, I realized that it wasn’t normal lunch talk for a couple. So, instead of learning about her work or friends, I had turned our conversation back to sex. Nice work, Jimmy.
“Nah,” she easily answered. Shelly moved from normal conversation to sex like shifting gears in her car, “I had an ex, nice enough guy but all he wanted was oral and, well it just wasn’t my thing.”
That struck me. “Not your thing?” I asked, skipping the rest of what I thought because it would have seemed rude to say, “Not your thing? Because you suck cock like you’re trying to break a speed record.”
She just shrugged. “Nope. I just didn’t want to. I suppose he tried to be nice about it but the fucker dumped me.”
“That sounds shitty,” I told her.
“Yeah. It was even on valentine’s day. Prick.” It might have been the first time I saw her hurt side. She didn’t show it for long. “It’s all good, though, I got back at him. I blew his brother so good that I know he found out what he’d be missing.”
I nodded. My inner voice told me, “Take note – girlfriend is the vengeful type.”
I had heard enough but Shelly felt the need to answer my question more fully. She explained, “The swallowing part is the worst so that’s why I wanted a guy who was into taking his own.” Then she paused as if to make sure I understood she was being sincere and went on, “It’s actually hot, you know. I didn’t think I’d get so into it but Jimmy, when guys, I mean, you, when you’re swallowing and damn… now that it’s other guys’ cum… oh, Jimmy…”
Her eyes went soft. Yeah, we were sharing something amazing. Still, she was a hard one to figure out. There were times I felt like our sex life was all about some ulterior motive of hers but then I’d see a sincere sexual reaction to what we were doing. I decided to forget about any mission she was on and let myself just focus on the fact that my girlfriend and I shared the same interest – we both loved me swallowing cum and that was good enough for me.
She smiled to help herself break the mood. “Hey, let’s not get all hot and bothered here. I need to talk to you.”
It wasn’t a break-up, I knew it then. It also wasn’t just a normal couple out to enjoy lunch, either. “What is it?” I asked.
“Look, you’ve been asking about Don and I’ve been asking him. I even asked another guy but nobody wants you there. They say it’s too weird. Don said I could do him, and keep spitting into a glass but seeing some guy on the floor next to me isn’t doing it for him.”
Having had cum fresh from Shelly’s mouth, I wasn’t about to go back to my shotglass unless I had to. Wait… did she say “keep spitting into a glass”? It occurred to me that it was Don’s cum I’d been enjoying all along. Shelly didn’t have a girlfriend who was collecting cum for our sessions – it was her, it was Shelly blowing Don and lying to me.
That should have bothered me, at least the lying part.
But, nope. Instead of getting upset and calling her out, I asked, “Maybe you know some other guys?”
“Jimmy, you gotta appreciate it. I mean it does mess up the mood.”
She was right, of course. Don was right. I nodded. She had taken the time to see me about her news. She could have just messaged me. It was the one, the only genuinely sweet thing that girl would do during our relationship.
We sat there, not saying anything as our water glasses were refilled but once the waitress left I asked, “Shell, what I looked like a girl?”
She didn’t reply to my ideas but her eventual answer was unnerving. Now, for most guys, it wouldn’t be a big deal if their girlfriend invited them to lunch but when Shelly suggested it, I freaked out.
We didn’t have a “go to lunch” relationship. I worried she was dumping me but somehow managed not to ask if she was. Instead, I just met her as agreed and tried not to act like I was worried my new world was coming to a premature ending.
She asked about my day and I guessed some kind of small talk was the right thing to do. Part of me wondered if, maybe, she didn’t have some grand announcement. Like, maybe we were going to have a normal relationship?
I felt the need to keep the conversation going.
I’m not good at that sort of thing so I just asked, “Is this snowballing something you’ve always been into?”
Of course, as soon as I asked, I realized that it wasn’t normal lunch talk for a couple. So, instead of learning about her work or friends, I had turned our conversation back to sex. Nice work, Jimmy.
“Nah,” she easily answered. Shelly moved from normal conversation to sex like shifting gears in her car, “I had an ex, nice enough guy but all he wanted was oral and, well it just wasn’t my thing.”
That struck me. “Not your thing?” I asked, skipping the rest of what I thought because it would have seemed rude to say, “Not your thing? Because you suck cock like you’re trying to break a speed record.”
She just shrugged. “Nope. I just didn’t want to. I suppose he tried to be nice about it but the fucker dumped me.”
“That sounds shitty,” I told her.
“Yeah. It was even on valentine’s day. Prick.” It might have been the first time I saw her hurt side. She didn’t show it for long. “It’s all good, though, I got back at him. I blew his brother so good that I know he found out what he’d be missing.”
I nodded. My inner voice told me, “Take note – girlfriend is the vengeful type.”
I had heard enough but Shelly felt the need to answer my question more fully. She explained, “The swallowing part is the worst so that’s why I wanted a guy who was into taking his own.” Then she paused as if to make sure I understood she was being sincere and went on, “It’s actually hot, you know. I didn’t think I’d get so into it but Jimmy, when guys, I mean, you, when you’re swallowing and damn… now that it’s other guys’ cum… oh, Jimmy…”
Her eyes went soft. Yeah, we were sharing something amazing. Still, she was a hard one to figure out. There were times I felt like our sex life was all about some ulterior motive of hers but then I’d see a sincere sexual reaction to what we were doing. I decided to forget about any mission she was on and let myself just focus on the fact that my girlfriend and I shared the same interest – we both loved me swallowing cum and that was good enough for me.
She smiled to help herself break the mood. “Hey, let’s not get all hot and bothered here. I need to talk to you.”
It wasn’t a break-up, I knew it then. It also wasn’t just a normal couple out to enjoy lunch, either. “What is it?” I asked.
“Look, you’ve been asking about Don and I’ve been asking him. I even asked another guy but nobody wants you there. They say it’s too weird. Don said I could do him, and keep spitting into a glass but seeing some guy on the floor next to me isn’t doing it for him.”
Having had cum fresh from Shelly’s mouth, I wasn’t about to go back to my shotglass unless I had to. Wait… did she say “keep spitting into a glass”? It occurred to me that it was Don’s cum I’d been enjoying all along. Shelly didn’t have a girlfriend who was collecting cum for our sessions – it was her, it was Shelly blowing Don and lying to me.
That should have bothered me, at least the lying part.
But, nope. Instead of getting upset and calling her out, I asked, “Maybe you know some other guys?”
“Jimmy, you gotta appreciate it. I mean it does mess up the mood.”
She was right, of course. Don was right. I nodded. She had taken the time to see me about her news. She could have just messaged me. It was the one, the only genuinely sweet thing that girl would do during our relationship.
We sat there, not saying anything as our water glasses were refilled but once the waitress left I asked, “Shell, what I looked like a girl?”
What If?
A second long silence followed my suggestion. I hadn’t thought it through at all; it was impulsive.
Taking Don’s warm cum right from Shelly’s mouth had given me all the luxurious mouthfeel of my own plus the erotic fascination of someone else’s fluid that I had from the shotglass. “I’m sorry,” I apologized, thinking my suggestion bothered her, “I just really liked that.”
“I’ve never seen anyone so happy,” Shelly commented. She took my hand across the table which shocked me. Shelly didn’t seem the PDA type, “Jimmy, you were so complete, so satisfied and the whole thing was insanely erotic and hot. I can’t get that moment out of my mind. I really want to see you like that again and that’s why I wanted to tell you in person.”
She paused and I could tell I was hearing her real feelings when she told me, “I just had no idea how much I’d be into this and I don’t want it to end.”
Oh, yes, we were made for one another.
“Let me see if I can do it,” I suggested, “I’m off early tomorrow. How about I give it a try and you can some see what you think after work?”
The moment she nodded my brain went into overdrive with ideas. First, I knew I needed to change my appearance. “I gotta look different,” I told her, “You know, in case someone sees me.”
As she started talking, I flashed to an image of my neighbors seeing me in drag and the unrelenting humiliation that would follow.
Shelly agreed and I suggested I start by getting a wig. Shelly objected, telling me, “Don’s a real hair grabber,” she noted, “more of a puller, actually and your hair’s long enough.”
“Can I color it for the night, like go blonde or something?”
In the short time I’d known her, I’d seen Shelly as a blonde, redhead and with pink streaks. She explained, “If your hair was light, sure, but yours is already dark brown. You can go darker but the only way to go lighter would be permanent.”
“Huh,” I replied, gesturing to her hair, “Must be nice to be a blonde.”
“I’ll come up with some other ideas,” I told her.
Shelly had little interest in my plans to look like a girl so I stopped trying to get her involved. She speedily ate her sandwich as if we had exceeded our time for our only outing that didn’t directly involve sex. She left money and said she needed to get back to work, leaving me to finish alone and think about how I could become unrecognizable.
Research, research, research. I spent that night learning about costumes and makeup. There was a world of information about boys who wanted to look like girls and about girls who wanted to look like someone else!
Though I was unsure if I’d ever take them, I ordered a female hormone kit online. It wasn’t too expensive and, while it was probably illegal, it did promise great results. I’d think about whether to take it or not.
I took my list and the ideas in my head out shopping with me the next afternoon. The first stop was Shelly’s idea – temporary hair color to darken my hair. But the cool one was mine – freckles. Yes, freckles. I got the inspiration on some actor’s blog and her pictures were amazing, she totally looked different. My hope was that the freckles, along with ordinary makeup, would totally change the way I looked.
I did the hair color myself but didn’t get started until pretty late in the afternoon. I had just rinsed it when Shelly messaged to say she could come by to see how I look. That left me rushed to put on the freckles and a little makeup. I followed the instructions for some eye shadow and pulled a line of eyeliner like I had seen in a makeup tutorial. Then I dotted the freckles and brushed on some blush. A little lipstick and then I went in to blow-dry my hair. I had an idea about styling using a big round brush I’d gotten.
But Shelly was at my door. “Crap!” I called out, “I’m not ready!”
“Don’t be a baby,” she said from the other side of the door, “I don’t care!” I could hear a little chuckle. It hadn’t occurred to me that this would be fun for us and I liked that idea.
“Don’t look!” I whined as I opened the door.
I scurried to the bathroom as she called out, “Get back here and let me see!”
I laughed as I dried my hair, Shelly pestering me from outside my bathroom. “Fine! So much for styling it!” I told her before opening the door.
“Alright,” I announced, “meet Olivia.”
I don’t know what I was expecting. I guess I wanted her to love it. Instead, though, Shelly looked at me with unemotional analysis.
“It’s certainly different,” were her first words.
It wasn’t what I wanted to hear.
“Look, Jimmy, you sound like a girl and you’re tiny, so this won’t be hard. I think you just need to put in a little more effort, okay?”
Still not what I wanted to hear.
I sighed.
Shelly was all business. “We only have one shot at this, with Don, anyway. It’s not like he’s going to say, ‘still looks like a dude, try again.’ We need to really wow him, okay?” She added, “I mean, if you want to…”
“I really want to, Shell.”
“I know you do, Jimmy, and I want it, too.”
We were made for each other. “Thank god I have you. I’ll work on it,” I told her.
Taking Don’s warm cum right from Shelly’s mouth had given me all the luxurious mouthfeel of my own plus the erotic fascination of someone else’s fluid that I had from the shotglass. “I’m sorry,” I apologized, thinking my suggestion bothered her, “I just really liked that.”
“I’ve never seen anyone so happy,” Shelly commented. She took my hand across the table which shocked me. Shelly didn’t seem the PDA type, “Jimmy, you were so complete, so satisfied and the whole thing was insanely erotic and hot. I can’t get that moment out of my mind. I really want to see you like that again and that’s why I wanted to tell you in person.”
She paused and I could tell I was hearing her real feelings when she told me, “I just had no idea how much I’d be into this and I don’t want it to end.”
Oh, yes, we were made for one another.
“Let me see if I can do it,” I suggested, “I’m off early tomorrow. How about I give it a try and you can some see what you think after work?”
The moment she nodded my brain went into overdrive with ideas. First, I knew I needed to change my appearance. “I gotta look different,” I told her, “You know, in case someone sees me.”
As she started talking, I flashed to an image of my neighbors seeing me in drag and the unrelenting humiliation that would follow.
Shelly agreed and I suggested I start by getting a wig. Shelly objected, telling me, “Don’s a real hair grabber,” she noted, “more of a puller, actually and your hair’s long enough.”
“Can I color it for the night, like go blonde or something?”
In the short time I’d known her, I’d seen Shelly as a blonde, redhead and with pink streaks. She explained, “If your hair was light, sure, but yours is already dark brown. You can go darker but the only way to go lighter would be permanent.”
“Huh,” I replied, gesturing to her hair, “Must be nice to be a blonde.”
“I’ll come up with some other ideas,” I told her.
Shelly had little interest in my plans to look like a girl so I stopped trying to get her involved. She speedily ate her sandwich as if we had exceeded our time for our only outing that didn’t directly involve sex. She left money and said she needed to get back to work, leaving me to finish alone and think about how I could become unrecognizable.
Research, research, research. I spent that night learning about costumes and makeup. There was a world of information about boys who wanted to look like girls and about girls who wanted to look like someone else!
Though I was unsure if I’d ever take them, I ordered a female hormone kit online. It wasn’t too expensive and, while it was probably illegal, it did promise great results. I’d think about whether to take it or not.
I took my list and the ideas in my head out shopping with me the next afternoon. The first stop was Shelly’s idea – temporary hair color to darken my hair. But the cool one was mine – freckles. Yes, freckles. I got the inspiration on some actor’s blog and her pictures were amazing, she totally looked different. My hope was that the freckles, along with ordinary makeup, would totally change the way I looked.
I did the hair color myself but didn’t get started until pretty late in the afternoon. I had just rinsed it when Shelly messaged to say she could come by to see how I look. That left me rushed to put on the freckles and a little makeup. I followed the instructions for some eye shadow and pulled a line of eyeliner like I had seen in a makeup tutorial. Then I dotted the freckles and brushed on some blush. A little lipstick and then I went in to blow-dry my hair. I had an idea about styling using a big round brush I’d gotten.
But Shelly was at my door. “Crap!” I called out, “I’m not ready!”
“Don’t be a baby,” she said from the other side of the door, “I don’t care!” I could hear a little chuckle. It hadn’t occurred to me that this would be fun for us and I liked that idea.
“Don’t look!” I whined as I opened the door.
I scurried to the bathroom as she called out, “Get back here and let me see!”
I laughed as I dried my hair, Shelly pestering me from outside my bathroom. “Fine! So much for styling it!” I told her before opening the door.
“Alright,” I announced, “meet Olivia.”
I don’t know what I was expecting. I guess I wanted her to love it. Instead, though, Shelly looked at me with unemotional analysis.
“It’s certainly different,” were her first words.
It wasn’t what I wanted to hear.
“Look, Jimmy, you sound like a girl and you’re tiny, so this won’t be hard. I think you just need to put in a little more effort, okay?”
Still not what I wanted to hear.
I sighed.
Shelly was all business. “We only have one shot at this, with Don, anyway. It’s not like he’s going to say, ‘still looks like a dude, try again.’ We need to really wow him, okay?” She added, “I mean, if you want to…”
“I really want to, Shell.”
“I know you do, Jimmy, and I want it, too.”
We were made for each other. “Thank god I have you. I’ll work on it,” I told her.
If At First
I just needed more practice, I told myself, and I needed to complete the package. On Saturday morning I headed out in search of some kind of breast forms. I found hollow ones that women used to give themselves a cup-sized boost. “Can I borrow clothes for this?” I asked Shelly while I was out. I didn’t want to buy an outfit that I’d only use for our date with Don.
Yeah, at that time, I really didn’t think about how many times I might see Don and I sure didn’t think about dressing up for other guys Shelly might find for us. I just didn’t think about my future as Olivia. Instead, I only wanted to make everything work out so that we might be on Don’s living room floor that night.
“I would,” she replied, “but I don’t think you’re my size.”
“You sure?”
“Jimmy, you know you’re tiny, right? I mean, you’re perfect but my clothes would fall off of you.”
I guessed she just didn’t want me wearing her clothes. Sizing her up later, I was sure I could have.
The saleswoman helping me made up for Shelly’s indifference. “You might want a pair of these,” she said, taking me over to another rack.
The padded underwear had a high waist band with lacing in the back that would cinch tight. “You know, bigger hips and a smaller waist,” she told me. She seemed to be avoiding any gaze downward as though it would be impolite to notice my body.
I was still bothered by Shelly’s message and told the eager retail worker, “Sure, my jeans are, like 26 or 27 inches at the waist, can you pick out the right size?”
Then, still in a bit of a huff over my girlfriend telling me I was tiny, I went into a department store and grabbed some women’s jeans and a sweater and took them to a dressing room. I had to repeat the exercise a few times and added bras that, fortunately, nobody noticed, eventually getting something that would fit. “Just so you know, I’m a size four with a 32” chest. Isn’t that the same?” I wrote to Shelly at the end of the day. I expected her to apologize.
When she didn’t reply, I sent pictures of clothes that I found: a burgundy skirt made of stretchy leather-like material and a soft white sweater along with a pair of high heels and stockings. “Or would a black sweater be better?” I wrote.
I tried to visualize everything and asked, “Do I need women’s underwear?”
Still no reply, so I went ahead and bought what I had picked out which now included a white bra and panty set. I asked if I needed a lipstick in deeper red, like to match the skirt but she still didn’t get back to me. Resigned, I did my best to pick out makeup. While I was headed to check out at the drug store, I walked past hair products and picked up a curling iron. It was then that it occurred to me: why can’t I wear a wig? It’s not like this guy’s going to touch me. He just needs to look down and not see a guy in his house.
I asked Shelly but she was still busy so, what the heck, I went to a wig store where I bought one wig that was bit longer than my hair and a second one, an impulse buy, that was a lot longer.
“I got everything I need. Can tonight work? Maybe I can come by and get ready at your place?” I wrote to Shelly.
Back at home, I unpacked and got the outfit ready. I messaged Shelly a few more times and started to worry that our plans to go out that night wouldn’t come together.
I paced a bit and tried on the clothes which was smart because I had to figure out how to stuff the bra beneath the foam things. Shelly finally got back to me around seven. “Been tied up,” she wrote, “I got your messages. Can you be ready in an hour?”
“Yes! What about my questions?”
“Been busy, just do what we talked about, k?”
No, she hadn’t read my messages and it was clear that my girlfriend had little interest in helping with my female impersonation. I wouldn’t let that bother me. Shelly and I were sharing incredible sex and getting ready for it shouldn’t be her problem. Heck, she was doing all the hard work. It occurred to me that I was risking everything by being too needy.
I felt I did a much better job with makeup on my second attempt and my hair came out pretty close to the picture of the style I tried to copy. Looking in my bathroom mirror I thought, yes, Shelly would be much happier.
I pulled the panties on, my penis creating the smallest lump in the front, then the padded thing and laced it up tight before tying it, then the bra which I stuffed as I’d practiced. As I sat on my bed and pulled on the pantyhose, I began to think of what was in store for me. Mmm… that warm cum… Even the thought of it was enough to transport me to an erotic plain of delight.
The tan heels had an ankle strap and a long heel like the kind I’d seen women wear when they go out. I nearly crashed when I stood in them so I used the time waiting for my girlfriend to walk around my apartment. The snug skirt introduced another problem in walking and I realized I had a lot to learn if I wasn’t going to fall down in front of Don.
At that time, I still hadn’t thought of putting the outfit on again – all I could think about was being on the floor and receiving cum from Shelly’s mouth that night.
Shelly tapped on my door and I had to call out that I was coming as I slowly and awkwardly made my way to let her in. As she reacted to my appearance, I stuck my head out into the hall and instinctively looked left and right to make sure my neighbors weren’t in the hallway.
“Not bad,” she was saying for the second time once she was inside, “You ready to go?”
I stammered with questions. “Well, I…”
“We gotta roll, Jimmy. You look fine. C’mon.”
After opening the door, I checked the hallway again, whispering, “I’m not sure darker hair is enough to fool the neighbors.” Shelly seemed patient… sort of. The guys down the hall, Enrique and Paul, had terrorized me since I moved in. I was sure that if they saw me with makeup it would be the worst moment of my life.
I took her arm and held on as we walked at her brisk pace. Normally, I didn’t like that she moved quickly but paranoid I’d be seen in makeup, I wanted to race down the hall and into the relative safety of her car.
She talked to me on the way but I didn’t hear words. I wanted to shush her, worried one of my neighbors might hear a voice and open their door to take a look. I also needed to focus on not falling down. It wasn’t until I sat down on the passenger seat that I heard her.
“Those are really tall high heels, Jimmy, one helluva choice. Glad you didn’t break an ankle!”
“This is what women wear, right? I mean, for stuff like this.”
She shrugged. I never really noticed her shoes and I thought she had high heels on the night we met but, no, not since. She told me, “Maybe, but it’s not like it’s a requirement. It’s cool, though, they do show off your legs. As long as you don’t fall down, they’re great.” She shrugged, “I guess dressing trampy is the right way to go. Just don’t do anything to embarrass me.”
After giving her a “no hard feelings” expression, my butterflies and I rode in silence. At a stoplight, Shelly smiled with a quizzical expression and told me, “It really doesn’t look like you,” then, after a squinting look, added, “Your skin looks whiter and pinkish or something. Even your lips… like they’re a different shape.”
I simply told her I was trying to look different but she still didn’t seem to appreciate the risk I was taking, going out dressed like a girl.
“You’re pretty cute like that, you know.”
I was going for passable and had little interest in her compliments. Boy, that would change.
Yeah, at that time, I really didn’t think about how many times I might see Don and I sure didn’t think about dressing up for other guys Shelly might find for us. I just didn’t think about my future as Olivia. Instead, I only wanted to make everything work out so that we might be on Don’s living room floor that night.
“I would,” she replied, “but I don’t think you’re my size.”
“You sure?”
“Jimmy, you know you’re tiny, right? I mean, you’re perfect but my clothes would fall off of you.”
I guessed she just didn’t want me wearing her clothes. Sizing her up later, I was sure I could have.
The saleswoman helping me made up for Shelly’s indifference. “You might want a pair of these,” she said, taking me over to another rack.
The padded underwear had a high waist band with lacing in the back that would cinch tight. “You know, bigger hips and a smaller waist,” she told me. She seemed to be avoiding any gaze downward as though it would be impolite to notice my body.
I was still bothered by Shelly’s message and told the eager retail worker, “Sure, my jeans are, like 26 or 27 inches at the waist, can you pick out the right size?”
Then, still in a bit of a huff over my girlfriend telling me I was tiny, I went into a department store and grabbed some women’s jeans and a sweater and took them to a dressing room. I had to repeat the exercise a few times and added bras that, fortunately, nobody noticed, eventually getting something that would fit. “Just so you know, I’m a size four with a 32” chest. Isn’t that the same?” I wrote to Shelly at the end of the day. I expected her to apologize.
When she didn’t reply, I sent pictures of clothes that I found: a burgundy skirt made of stretchy leather-like material and a soft white sweater along with a pair of high heels and stockings. “Or would a black sweater be better?” I wrote.
I tried to visualize everything and asked, “Do I need women’s underwear?”
Still no reply, so I went ahead and bought what I had picked out which now included a white bra and panty set. I asked if I needed a lipstick in deeper red, like to match the skirt but she still didn’t get back to me. Resigned, I did my best to pick out makeup. While I was headed to check out at the drug store, I walked past hair products and picked up a curling iron. It was then that it occurred to me: why can’t I wear a wig? It’s not like this guy’s going to touch me. He just needs to look down and not see a guy in his house.
I asked Shelly but she was still busy so, what the heck, I went to a wig store where I bought one wig that was bit longer than my hair and a second one, an impulse buy, that was a lot longer.
“I got everything I need. Can tonight work? Maybe I can come by and get ready at your place?” I wrote to Shelly.
Back at home, I unpacked and got the outfit ready. I messaged Shelly a few more times and started to worry that our plans to go out that night wouldn’t come together.
I paced a bit and tried on the clothes which was smart because I had to figure out how to stuff the bra beneath the foam things. Shelly finally got back to me around seven. “Been tied up,” she wrote, “I got your messages. Can you be ready in an hour?”
“Yes! What about my questions?”
“Been busy, just do what we talked about, k?”
No, she hadn’t read my messages and it was clear that my girlfriend had little interest in helping with my female impersonation. I wouldn’t let that bother me. Shelly and I were sharing incredible sex and getting ready for it shouldn’t be her problem. Heck, she was doing all the hard work. It occurred to me that I was risking everything by being too needy.
I felt I did a much better job with makeup on my second attempt and my hair came out pretty close to the picture of the style I tried to copy. Looking in my bathroom mirror I thought, yes, Shelly would be much happier.I pulled the panties on, my penis creating the smallest lump in the front, then the padded thing and laced it up tight before tying it, then the bra which I stuffed as I’d practiced. As I sat on my bed and pulled on the pantyhose, I began to think of what was in store for me. Mmm… that warm cum… Even the thought of it was enough to transport me to an erotic plain of delight.
The tan heels had an ankle strap and a long heel like the kind I’d seen women wear when they go out. I nearly crashed when I stood in them so I used the time waiting for my girlfriend to walk around my apartment. The snug skirt introduced another problem in walking and I realized I had a lot to learn if I wasn’t going to fall down in front of Don.
At that time, I still hadn’t thought of putting the outfit on again – all I could think about was being on the floor and receiving cum from Shelly’s mouth that night.
Shelly tapped on my door and I had to call out that I was coming as I slowly and awkwardly made my way to let her in. As she reacted to my appearance, I stuck my head out into the hall and instinctively looked left and right to make sure my neighbors weren’t in the hallway.
“Not bad,” she was saying for the second time once she was inside, “You ready to go?”
I stammered with questions. “Well, I…”
“We gotta roll, Jimmy. You look fine. C’mon.”
After opening the door, I checked the hallway again, whispering, “I’m not sure darker hair is enough to fool the neighbors.” Shelly seemed patient… sort of. The guys down the hall, Enrique and Paul, had terrorized me since I moved in. I was sure that if they saw me with makeup it would be the worst moment of my life.
I took her arm and held on as we walked at her brisk pace. Normally, I didn’t like that she moved quickly but paranoid I’d be seen in makeup, I wanted to race down the hall and into the relative safety of her car.
She talked to me on the way but I didn’t hear words. I wanted to shush her, worried one of my neighbors might hear a voice and open their door to take a look. I also needed to focus on not falling down. It wasn’t until I sat down on the passenger seat that I heard her.
“Those are really tall high heels, Jimmy, one helluva choice. Glad you didn’t break an ankle!”
“This is what women wear, right? I mean, for stuff like this.”
She shrugged. I never really noticed her shoes and I thought she had high heels on the night we met but, no, not since. She told me, “Maybe, but it’s not like it’s a requirement. It’s cool, though, they do show off your legs. As long as you don’t fall down, they’re great.” She shrugged, “I guess dressing trampy is the right way to go. Just don’t do anything to embarrass me.”
After giving her a “no hard feelings” expression, my butterflies and I rode in silence. At a stoplight, Shelly smiled with a quizzical expression and told me, “It really doesn’t look like you,” then, after a squinting look, added, “Your skin looks whiter and pinkish or something. Even your lips… like they’re a different shape.”
I simply told her I was trying to look different but she still didn’t seem to appreciate the risk I was taking, going out dressed like a girl.
“You’re pretty cute like that, you know.”
I was going for passable and had little interest in her compliments. Boy, that would change.
Fine Tuning
I guess I would have thought that some kind of “Ready?” was in order when we reached our destination. Instead, Shelly just got out of the car and started for Don’s front door. She had already rung the doorbell when I caught up to her.
Don looked at me as he said, “Hey, Shelly. Looks like you brought a friend.”
With a nod in my direction, “Olivia,” she simply answered.
Don moved aside and Shelly walked in. I did my best to keep up. The house was eerily dark but I wouldn’t be deterred; I just kept moving.
I tried to read our host. Was he pleased? Did I pass?
“You ready to party?” Shelly asked him as she found her mark.
Don found his and said he was ready. Back in the same places as a few nights before, my girlfriend seduced the elixir producer as I looked around the room and tried to act invisible. Soon, Shelly hummed in a tell-tale way and I could see her right hand had disappeared below Don’s belt. She had found what she had helped prepare and began kneeling to reveal it.
I joined her on the floor, just a few feet away. It was just like my first time, though much more difficult to move in the snug skirt. So self-conscious… did the my boobs look real? Did I walk like I was used to high heels? Was I sitting as if I’d worn a skirt before?
Once there, I ignored our host and found it was easier for me to watch my girlfriend, since I wanted to avoid any unintended eye contact with another guy. Shelly was different with Don than she was with me. She couldn’t easily get him in her mouth so she used her hands a lot more. Caressing, pumping… her right hand and mouth worked like a well-rehearsed team and Don’s moans were evidence of the team’s precision.
Her hand slowly pumped as she turned to me. “Want his cum, Olivia?”
Keeping my eyes on my girlfriend, I told her, “So badly. Please, let me have it!”
I noticed a quiver, like a ripple, running through Don’s body from his hips to his chest. It was just like the last time before he came.
Cum…
The foreign constriction of the skirt left me, the clumsy heels disappeared, the oversized appendages beneath the soft sweater were no longer noticeable. I wasn’t a guy dressed up in women’s clothing – I wasn’t anyone at all. All that remained was the cream that was about to be delivered. I let out a soft gasp and then it happened.
Shelly’s vocalizations indicated her focus and struggle to accept the load. Don called out. The right hand pumped the beautiful fluid and I opened my mouth in anticipation.
My girlfriend turned, pressed her lips onto mine and instantly transported me to that haven of erotic wonder that had become my obsession. Sticky cum fell with gravity’s help into my mouth since Shelly had turned me and lain me down on my back. I whined with delight and let it all happen.
Flat on my back in another man’s living room, I waited there until Shelly returned for what I assumed would be the customary second round. I swallowed as she approached. Shelly put a hand beneath my chin as I opened up and, from a distance, she let the last of the cum fall into me.
“Ooh, Baby,” were the next words I could make out. Shelly was kneeling by me as I rejoined the world. “God but I love the way you get,” she told me.
Usually speedy, Shelly stood slowly with appreciation of my delicate state. She offered a hand to help me up. “He’s gone,” she told me, “we should get going, too.”
I nodded but didn’t move.
“You poor thing,” she said to me, “You must be super-horny now, aren’t you?”
A second nod.
She had an empathetic look and might have been able to see I was erect. “So sorry, Babe. We just can’t, not here.”
“I know.”
I took a breath and extended my hand.
In her car, Shelly told me, “Damn, Jimmy, that was so hot.”
I knew I was lucky to have found her. “The shopping, the hair styling, these damn shoes…” I began, “It felt impulsive and was actually a lot of work but, Shell, oh my god… so worth it.” Going out in a skirt and heels was also sort of fun but I didn’t tell her about that part.
I was still on my post-sex high after Shelly helped me sneak back into my apartment when it was interrupted with a critique. Shelly messaged me to say Don noticed a bulge while I was laying on his floor.
I simply replied, “Well, of course. What did he expect?”
Shelly, all-business Shelly told me, “Said he could see it even though he had the lights off. You’re gonna have to find a way to hide that thing.”
A man had found me presentable enough to invite me with my girlfriend. This, I told myself, was just fine-tuning.
Don looked at me as he said, “Hey, Shelly. Looks like you brought a friend.”
With a nod in my direction, “Olivia,” she simply answered.
Don moved aside and Shelly walked in. I did my best to keep up. The house was eerily dark but I wouldn’t be deterred; I just kept moving.
I tried to read our host. Was he pleased? Did I pass?
“You ready to party?” Shelly asked him as she found her mark.
Don found his and said he was ready. Back in the same places as a few nights before, my girlfriend seduced the elixir producer as I looked around the room and tried to act invisible. Soon, Shelly hummed in a tell-tale way and I could see her right hand had disappeared below Don’s belt. She had found what she had helped prepare and began kneeling to reveal it.
I joined her on the floor, just a few feet away. It was just like my first time, though much more difficult to move in the snug skirt. So self-conscious… did the my boobs look real? Did I walk like I was used to high heels? Was I sitting as if I’d worn a skirt before?
Once there, I ignored our host and found it was easier for me to watch my girlfriend, since I wanted to avoid any unintended eye contact with another guy. Shelly was different with Don than she was with me. She couldn’t easily get him in her mouth so she used her hands a lot more. Caressing, pumping… her right hand and mouth worked like a well-rehearsed team and Don’s moans were evidence of the team’s precision.
Her hand slowly pumped as she turned to me. “Want his cum, Olivia?”
Keeping my eyes on my girlfriend, I told her, “So badly. Please, let me have it!”
I noticed a quiver, like a ripple, running through Don’s body from his hips to his chest. It was just like the last time before he came.
Cum…
The foreign constriction of the skirt left me, the clumsy heels disappeared, the oversized appendages beneath the soft sweater were no longer noticeable. I wasn’t a guy dressed up in women’s clothing – I wasn’t anyone at all. All that remained was the cream that was about to be delivered. I let out a soft gasp and then it happened.
Shelly’s vocalizations indicated her focus and struggle to accept the load. Don called out. The right hand pumped the beautiful fluid and I opened my mouth in anticipation.
My girlfriend turned, pressed her lips onto mine and instantly transported me to that haven of erotic wonder that had become my obsession. Sticky cum fell with gravity’s help into my mouth since Shelly had turned me and lain me down on my back. I whined with delight and let it all happen.
Flat on my back in another man’s living room, I waited there until Shelly returned for what I assumed would be the customary second round. I swallowed as she approached. Shelly put a hand beneath my chin as I opened up and, from a distance, she let the last of the cum fall into me.
“Ooh, Baby,” were the next words I could make out. Shelly was kneeling by me as I rejoined the world. “God but I love the way you get,” she told me.
Usually speedy, Shelly stood slowly with appreciation of my delicate state. She offered a hand to help me up. “He’s gone,” she told me, “we should get going, too.”
I nodded but didn’t move.
“You poor thing,” she said to me, “You must be super-horny now, aren’t you?”
A second nod.
She had an empathetic look and might have been able to see I was erect. “So sorry, Babe. We just can’t, not here.”
“I know.”
I took a breath and extended my hand.
In her car, Shelly told me, “Damn, Jimmy, that was so hot.”
I knew I was lucky to have found her. “The shopping, the hair styling, these damn shoes…” I began, “It felt impulsive and was actually a lot of work but, Shell, oh my god… so worth it.” Going out in a skirt and heels was also sort of fun but I didn’t tell her about that part.
I was still on my post-sex high after Shelly helped me sneak back into my apartment when it was interrupted with a critique. Shelly messaged me to say Don noticed a bulge while I was laying on his floor.
I simply replied, “Well, of course. What did he expect?”
Shelly, all-business Shelly told me, “Said he could see it even though he had the lights off. You’re gonna have to find a way to hide that thing.”
A man had found me presentable enough to invite me with my girlfriend. This, I told myself, was just fine-tuning.
Technique
Our adventures required a lot of work and I understood Shelly’s participation would be limited. She found the guy and she drove but, other than that, didn’t do much. She was like one of those hands-off bosses who told me what I needed to do then let me figure it out.
So, when my girlfriend said that she wanted to “try something out” that might fix both the appearance problem and my desire to get off, I was more surprised than intrigued.
“Really?” was my reply. This was Shelly, after all, all-business, you-deal-with-your-stuff Shelly.
Yes, really. Shelly really wanted to help and had an idea that launched our relationship into a phase I now think of as educational. Like jumping into a difficult class, it was frustrating at first but my-oh-my was it all worth it.
She came over a few nights later. I had spent the intervening evenings jerking off as I relived the glory of the mouthful I’d enjoyed in a stranger’s living room. I tried, twice actually, taking my own cum in my mouth but, sadly, the joy had abandoned me. There was something about the recent memory of another man’s cum that had spoiled me from enjoying any self-pleasure in that way.
“It’s two things,” Shelly began when I anxiously asked her what she wanted to me to try.
The first was hiding my bump. “I’m surprised he even noticed,” I complained, “I thought it was hard to see.”
She just shrugged in a “the customer is always right” sort of way. I had to agree. If I wanted to keep getting my fix, I wasn’t going to argue my way out of this problem. “Get some tape,” she instructed. After I learned what I’d be doing with it, I easily realized there’s a better choice than masking tape and it would have been nice if my girlfriend had picked up a roll before coming over. Shelly introduced me to the tuck-and-tape routine that would forever conceal my little secret.
“Just tuck your balls up,” she said, “I think you’re supposed to stand while you do that part.”
Without a good reason, I hesitated to undress in front of her. Shelly just scoffed and I gave her a nervous smile and an apology, then took off my pants and underwear.
She looked on with curiosity as I worked. Overly cautious at first, I soon found it was easy to make my balls disappear. I announced success and Shelly said, “Cool. Now just push your cock down and tape it in place.
“Down there?” I objected.
Shelly’s second fault was not telling me to shave beforehand. There was a short exchange that she won and I used the shortest piece of masking tape that would do the job. Looking down, all I could see was pubic hair and a smooth pelvis. “Hmm,” I summarized, “pretty good, right?”
I was inspected and felt like a pupil or maybe someone on trial. When Shelly agreed, I actually felt pride.
“Now,” she said, taking my hand, “let’s try the other thing.
Oh… that other thing.
This one was going to be harder.
She lacked her usual confidence when she told me, “I want to see if you can come like that.”
I looked down. “like this?”
“Some guys do. I read about it.”
I scratched my head, “What’s the point?”
Shelly had thought this through and explained, “If you can come like that, I can get you off when we’re at Don’s, like, right after or during.”
I immediately saw the benefit. My shoulders relaxed and I sighed. “That would be so hot,” I told her.
But I doubted her. “You mean getting off while I’m taped down like this?”
She nodded. “Without getting hard.”
“Is that really possible?”
There was that uncertainty again but she repeated that she’d read about it.
I was willing to try and Shelly had me lie down. I noticed she always kissed before giving head. Shelly liked kissing until Don or I was hard; she would never put her mouth on a soft dick.
So we went along with our usual until it started to produce the usual result. I pushed her away. “It’s killing me, Shell, I can’t do this!”
Sure enough, my dick was stiffening and pulling away at the tape which, in turn, was pulling away on the hair down there.
Although it was Shelly’s idea, I was infatuated with it as soon as she mentioned it to me. I was the one who insisted we try again and when the second attempt failed, it was me who suggested we try yet again the next night.
My first fix was obvious – that hair needed to go. In my shower, I squatted and began shaving where the tape would go. Not sure where to stop, I carefully shaved my ball sack and up the sides a little. When that looked weird, I went ahead and removed all of my pubic hair because I never wanted to experience the pain of having it pulled again.
Secondly, I bought better tape - a simple tan athletic tape that would fold and flex naturally.
With the two easy fixes ready, I drove to Shelly’s house pre-taped and bump-free, ready to train myself for an erection-free orgasm.
I left my jeans on as Shelly and I began kissing. The anticipation of having a climax while experiencing a mouthful of cum motivated me to ignore the pain of a growing erection.
But only for so long. “Ahh!” I complained as I pushed her away, “It’s killing me!”
Shelly sat up and looked at me with the sad eyes of coach who was witnessing failure.
“Where did you read about this, anyway?” I asked, suddenly wondering if my girlfriend was just making things up.
That night, Shelly told me and turned me on to what would eventually be our solution.
No, she hadn’t made it up. Guys could climax without an erection but the ones who wrote about it all had one thing in common. These guys were really enjoying sex and having great orgasms but they had to master a mind-trick.
They had to think of themselves as women.
So, when my girlfriend said that she wanted to “try something out” that might fix both the appearance problem and my desire to get off, I was more surprised than intrigued.
“Really?” was my reply. This was Shelly, after all, all-business, you-deal-with-your-stuff Shelly.
Yes, really. Shelly really wanted to help and had an idea that launched our relationship into a phase I now think of as educational. Like jumping into a difficult class, it was frustrating at first but my-oh-my was it all worth it.
She came over a few nights later. I had spent the intervening evenings jerking off as I relived the glory of the mouthful I’d enjoyed in a stranger’s living room. I tried, twice actually, taking my own cum in my mouth but, sadly, the joy had abandoned me. There was something about the recent memory of another man’s cum that had spoiled me from enjoying any self-pleasure in that way.
“It’s two things,” Shelly began when I anxiously asked her what she wanted to me to try.
The first was hiding my bump. “I’m surprised he even noticed,” I complained, “I thought it was hard to see.”
She just shrugged in a “the customer is always right” sort of way. I had to agree. If I wanted to keep getting my fix, I wasn’t going to argue my way out of this problem. “Get some tape,” she instructed. After I learned what I’d be doing with it, I easily realized there’s a better choice than masking tape and it would have been nice if my girlfriend had picked up a roll before coming over. Shelly introduced me to the tuck-and-tape routine that would forever conceal my little secret.
“Just tuck your balls up,” she said, “I think you’re supposed to stand while you do that part.”
Without a good reason, I hesitated to undress in front of her. Shelly just scoffed and I gave her a nervous smile and an apology, then took off my pants and underwear.
She looked on with curiosity as I worked. Overly cautious at first, I soon found it was easy to make my balls disappear. I announced success and Shelly said, “Cool. Now just push your cock down and tape it in place.
“Down there?” I objected.
Shelly’s second fault was not telling me to shave beforehand. There was a short exchange that she won and I used the shortest piece of masking tape that would do the job. Looking down, all I could see was pubic hair and a smooth pelvis. “Hmm,” I summarized, “pretty good, right?”
I was inspected and felt like a pupil or maybe someone on trial. When Shelly agreed, I actually felt pride.
“Now,” she said, taking my hand, “let’s try the other thing.
Oh… that other thing.
This one was going to be harder.
She lacked her usual confidence when she told me, “I want to see if you can come like that.”
I looked down. “like this?”
“Some guys do. I read about it.”
I scratched my head, “What’s the point?”
Shelly had thought this through and explained, “If you can come like that, I can get you off when we’re at Don’s, like, right after or during.”
I immediately saw the benefit. My shoulders relaxed and I sighed. “That would be so hot,” I told her.
But I doubted her. “You mean getting off while I’m taped down like this?”
She nodded. “Without getting hard.”
“Is that really possible?”
There was that uncertainty again but she repeated that she’d read about it.
I was willing to try and Shelly had me lie down. I noticed she always kissed before giving head. Shelly liked kissing until Don or I was hard; she would never put her mouth on a soft dick.
So we went along with our usual until it started to produce the usual result. I pushed her away. “It’s killing me, Shell, I can’t do this!”
Sure enough, my dick was stiffening and pulling away at the tape which, in turn, was pulling away on the hair down there.
Although it was Shelly’s idea, I was infatuated with it as soon as she mentioned it to me. I was the one who insisted we try again and when the second attempt failed, it was me who suggested we try yet again the next night.
My first fix was obvious – that hair needed to go. In my shower, I squatted and began shaving where the tape would go. Not sure where to stop, I carefully shaved my ball sack and up the sides a little. When that looked weird, I went ahead and removed all of my pubic hair because I never wanted to experience the pain of having it pulled again.
Secondly, I bought better tape - a simple tan athletic tape that would fold and flex naturally.
With the two easy fixes ready, I drove to Shelly’s house pre-taped and bump-free, ready to train myself for an erection-free orgasm.
I left my jeans on as Shelly and I began kissing. The anticipation of having a climax while experiencing a mouthful of cum motivated me to ignore the pain of a growing erection.
But only for so long. “Ahh!” I complained as I pushed her away, “It’s killing me!”
Shelly sat up and looked at me with the sad eyes of coach who was witnessing failure.
“Where did you read about this, anyway?” I asked, suddenly wondering if my girlfriend was just making things up.
That night, Shelly told me and turned me on to what would eventually be our solution.
No, she hadn’t made it up. Guys could climax without an erection but the ones who wrote about it all had one thing in common. These guys were really enjoying sex and having great orgasms but they had to master a mind-trick.
They had to think of themselves as women.
Technique Trails
I had been reading since I got home and made my discovery when it was late. Knowing she wouldn’t reply, I still sent her a message; I was too excited to keep it to myself. As I typed, I grew more excited and told her how it all made sense to me and how I thought it just might work. I used dozens of exclamation points; I was so eager to try!
It wasn’t until the middle of the next day that Shelly would reply to my lengthy message. “Makes sense,” was all she said.
I tried not to be disappointed with the lack of shared enthusiasm. “Can we get together tonight so we can try it?” I asked her.
Her schedule meant I had to wait so I spent some time just sitting quietly and letting my mind think of myself as a girl. I couldn’t tell if it was working but I did seem to forget about my penis. I kept it tucked and taped for the whole day at work hoping that might help me perform with Shelly.
“You doing okay, Jimmy?” my work friend asked. I just shrugged and said I was fine, then asked why.
“You seem, I don’t know, different,” Ted told me. We actually talked for a few minutes before I realized what was going on and it was more than just making my dick disappear. In my mind, I was a girl at work that day and my only friend was bound to notice. He ended it by saying, “Alright, but if you ever need to talk, you know where to find me,” then he smiled and moved on.
I was knocking on Shelly’s door exactly at eight after thinking about sex all day. She greeted me with her usual, “Hey,” as she let me in. That girl was always so cool. There I was, bubbling over with excitement and she was just as casual as ever.
“You’re gonna think like you’re, what was that name… O-something?” she asked.
That’s right! “Olivia!” I answered, “I hadn’t thought of that but, yeah, the name will help.”
I hadn’t given it a lot of thought when I needed to name to give to Don. I really had no idea that I was making a commitment when I picked it.
“C’mon, Olivia,” Shelly said in her seductress voice, “Let’s sit down.”
Her first kiss made me a little nervous. Would this work?
Shelly was doing her best and kept calling me Olivia as we made out. I’d say I was about half-way into it. I couldn’t really enjoy our kissing and kept thinking, “I’m a girl, I’m a girl.”
When Shelly reached down my pants, she found nothing but a smooth hump. Normally, she was looking for an erection but hummed like she always did, this time because there was no erection.
So far, so good.
She pulled down my pants and commented, “Ooh, you shaved,” once I was half-naked and lying back.
“For the tape,” I told her.
Keeping in the mood, Shelly hummed as she went down on me.
Her tongue touched me just above the spot where my shaft began.
I flinched and Shelly giggled and teased, “Sensitive, Olivia?”
“That’s nice,” I replied.
Shelly began pulsing her tongue and I moaned a bit but then the discomfort began. My moans turned to yelps as my dick came to life. Sensing it, Shelly tried to calm me, “Shhh, Olivia,” she said softly, “I’m just eating your pussy.”
She was doing everything right but I just… I couldn’t. “Stop! It hurts too much!” I called out as I violently pulled away from her and sat up.
Shelly seemed bothered. I didn’t know what to say. I curled my body into a ball and began to cry.
“Hey, it’s getting late,” Shelly said as she picked up my pants, “You’ll be okay.”
Sobbing while I got dressed, I lamented, “I was really trying.”
“I know you were.”
“I’m so sorry.”
“It’s okay, Jimmy, I’ll bet I can get Don to cum into your cup and I can bring that over to your place.”
Standing up, I pouted, “It’s just not the same.”
There probably wasn’t a good answer to that so Shelly just said, “I gotta wash my hair. Can you let yourself out?”
I felt like a complete failure. I had let myself think it would be easy to get in the right mindset and had barely come close.
It wasn’t until I was home and putting things away that I saw the high heels I’d bought.
“Shoes!” I said to them. Rushing over to the drawer where I kept them, I pulled out the sweater, “And the sweater!” then the skirt, “and the skirt!”
My heart thumped and I took the few steps into my bathroom, opened the lower cabinet and pulled out the bag that contained cosmetics, saying, “Makeup!”
Yes! I had discovered the solution!
If I was going to think of myself as a girl, I needed to look like one!
It wasn’t until the middle of the next day that Shelly would reply to my lengthy message. “Makes sense,” was all she said.
I tried not to be disappointed with the lack of shared enthusiasm. “Can we get together tonight so we can try it?” I asked her.
Her schedule meant I had to wait so I spent some time just sitting quietly and letting my mind think of myself as a girl. I couldn’t tell if it was working but I did seem to forget about my penis. I kept it tucked and taped for the whole day at work hoping that might help me perform with Shelly.
“You doing okay, Jimmy?” my work friend asked. I just shrugged and said I was fine, then asked why.
“You seem, I don’t know, different,” Ted told me. We actually talked for a few minutes before I realized what was going on and it was more than just making my dick disappear. In my mind, I was a girl at work that day and my only friend was bound to notice. He ended it by saying, “Alright, but if you ever need to talk, you know where to find me,” then he smiled and moved on.
I was knocking on Shelly’s door exactly at eight after thinking about sex all day. She greeted me with her usual, “Hey,” as she let me in. That girl was always so cool. There I was, bubbling over with excitement and she was just as casual as ever.
“You’re gonna think like you’re, what was that name… O-something?” she asked.
That’s right! “Olivia!” I answered, “I hadn’t thought of that but, yeah, the name will help.”
I hadn’t given it a lot of thought when I needed to name to give to Don. I really had no idea that I was making a commitment when I picked it.
“C’mon, Olivia,” Shelly said in her seductress voice, “Let’s sit down.”
Her first kiss made me a little nervous. Would this work?
Shelly was doing her best and kept calling me Olivia as we made out. I’d say I was about half-way into it. I couldn’t really enjoy our kissing and kept thinking, “I’m a girl, I’m a girl.”
When Shelly reached down my pants, she found nothing but a smooth hump. Normally, she was looking for an erection but hummed like she always did, this time because there was no erection.
So far, so good.
She pulled down my pants and commented, “Ooh, you shaved,” once I was half-naked and lying back.
“For the tape,” I told her.
Keeping in the mood, Shelly hummed as she went down on me.
Her tongue touched me just above the spot where my shaft began.
I flinched and Shelly giggled and teased, “Sensitive, Olivia?”
“That’s nice,” I replied.
Shelly began pulsing her tongue and I moaned a bit but then the discomfort began. My moans turned to yelps as my dick came to life. Sensing it, Shelly tried to calm me, “Shhh, Olivia,” she said softly, “I’m just eating your pussy.”
She was doing everything right but I just… I couldn’t. “Stop! It hurts too much!” I called out as I violently pulled away from her and sat up.
Shelly seemed bothered. I didn’t know what to say. I curled my body into a ball and began to cry.
“Hey, it’s getting late,” Shelly said as she picked up my pants, “You’ll be okay.”
Sobbing while I got dressed, I lamented, “I was really trying.”
“I know you were.”
“I’m so sorry.”
“It’s okay, Jimmy, I’ll bet I can get Don to cum into your cup and I can bring that over to your place.”
Standing up, I pouted, “It’s just not the same.”
There probably wasn’t a good answer to that so Shelly just said, “I gotta wash my hair. Can you let yourself out?”
I felt like a complete failure. I had let myself think it would be easy to get in the right mindset and had barely come close.
It wasn’t until I was home and putting things away that I saw the high heels I’d bought.
“Shoes!” I said to them. Rushing over to the drawer where I kept them, I pulled out the sweater, “And the sweater!” then the skirt, “and the skirt!”
My heart thumped and I took the few steps into my bathroom, opened the lower cabinet and pulled out the bag that contained cosmetics, saying, “Makeup!”
Yes! I had discovered the solution!
If I was going to think of myself as a girl, I needed to look like one!
“Sorry about tonight,” I wrote to Shelly, “but I think I figured it out!”
My excited message went on the explain my idea and also about my feelings and why I thought it would work. “I didn’t tell you that night but I liked going out dressed like that,” I explained. “I don’t think I realized it then but it was exciting, like I was into it. If I just let those feelings go, I think it’ll really help me have sex like a girl with you!”
I apologized again and thanked her for being patient. She was never one for late-night messaging so I wasn’t surprised when she didn’t write back.
Finally, the next morning, “Sounds ok,” her message read, “but I don’t want to keep trying new ideas forever.”
I couldn’t blame her. “I’m sure this is it!” I wrote, “Can you come over tonight?”
“Why not here?”
“I’m going to dress up and I don’t want to leave my place if I don’t have to.”
“Ok,” she wrote, “I can come over Sunday at 8.”
That left three days – three days I didn’t want to wait but I knew better than to argue. “See you then,” was all I said.
Three days is an eternity for a sex addict and it’s way worse when you know that you’re just waiting to pass a test so that you can then arrange to get your fix. I did my best to keep my mind on work and other stuff but it was just impossible.
It was while showering that I noticed my legs. My hairy legs. Shelly will have to take off the pantyhose; How are we both supposed to think of me as a girl if I have hairy legs? Shorts season had passed so there was no harm in shaving them, which turned out to be pretty easy to do.
I must have dressed and undressed in that outfit a half-dozen times before Shelly would see me. I even put on all the makeup twice because I wanted everything to be perfect. I bought kiss-proof lipstick so that I wouldn’t get it all over Shelly when we made out. Shelly wasn’t going to give me another chance and I really needed a way to get back into that man’s house so my girlfriend could feed my burning desire for his cum.
I paced as I waited for her. In the mirror, I was a little disappointed seeing a body that wasn’t quite right. I didn’t want Shelly to have to deal with the padded panty so it was folded in a drawer in my room. I shifted my weight hoping to create the illusion of bigger hips but it wasn’t the same. That’s the night I started on the female hormones. It was impulsive and driven by my disappointment but I would continue taking them every day thereafter. I shook it off the bad feelings and tried to make use of the time and distracted myself by practicing in high heels. Shelly arrived nearly a half-hour late but I just smiled and thanked her for coming. “Sorry, I just don’t want to go out like this if I can avoid it.” She seemed to appreciate that.
As if she had remembered the game, she said, “Hello, Olivia, thanks for inviting me,” with an emphasis on the name.
I smiled, a little bashfully, as if she was being overly nice to me.
Her casual gaze turned into an analytical stare that went on uncomfortably long. “What?” I asked.
“It’s just that,” she began, “you look great, like sexy and really pretty.” Shelly seemed to be trying to figure something out and told me, “I guess I never really noticed before.”
“I wanted to make sure I got everything right.”
“It’s more than that,” she explained. Then my girlfriend adopted a let’s-be-honest tone and went on, “You know I’m not really into looks. When I met you, you were just a cute guy who was petite and, you know, into what I’m into. And when you first went out as a girl, well, I don’t know what the hell you did with all that makeup but you didn’t look like you and you really made yourself look bad. Now, though, damn… you’re really something.” She sighed, “I just never noticed before.”
“I needed the disguise when we went out but nobody’s going to see me tonight,” I explained, adding, “Nobody but you, of course.”
She looked at me once more and I felt it – the appreciation. I didn’t believe her completely but the idea that someone thought of me as sexy satisfied a need I didn’t know I had.
More than that, I was Olivia, sexy Olivia and fell into an erotic mood as a girl about to have sex.
We kissed on my couch and Shelly soon followed her standard playbook, reaching down, this time down a skirt, to find what she sought, this time a non-erection.
She hummed.
I felt wonderful. Turned-on and present. I was the girl whose name Shelly kept repeating.
The skirt was stretchy and Shelly struggled pulling it over my hips. “I can stand,” I offered, “It’ll come off easy enough since it’s just me under here.”
She helped me up and watched as I wiggled it off. “How did I not notice your hips before?” she pondered aloud.
I just answered, “I don’t really show off my body.” I didn’t want to break the mood and guessed she was talking about the pads and how different I looked with them on. “I’ll look better when we go out,” I simply said.
“Can you get the hose off, too?” she asked, “I don’t want to run them.”
As I started, Shelly huffed, “Not like that! Roll them down your legs.” She had a “don’t you know anything?” expression that I chose not to respond to.
As I got back on the couch, Shelly’s eyes went right to my legs. “You shaved?”
“I figured I should.”
“Yeah, that’s better, I think,” she agreed. I was trying to read her, worried, of course that she might just say the whole thing was too weird and bolt out of my apartment. From our first night, Shelly had shown genuine satisfaction as I ate cum. This though – me looking like a girl – was new and it was my idea. Shelly seemed to be warming up to it.
I started on the panties but her hand went to mine. “Let me,” she said in one of the rare confessions of desire that woman ever uttered. I must have looked surprised because Shelly seemed guilty or something, “What? It’s hot,” she explained. She was probably having her own doubts about her turn-ons but we would never have that conversation.
She wanted me, like not just for some rote sexual act but with real impulsive desire. Her feelings fueled mine and when she said, “I love undressing you, Olivia,” I had become something I’d never been before. I was an object of desire.
And it was intoxicating.
Shelly caressed my legs in a way she had never done before. She kissed my thigh and smiled at me. “You know you’re sort of purring,” she said softly.
I had no idea. In case I would misunderstand, she added, “I like it. It’s sexy, just like you, Olivia.”
Oh, what the hell. Whatever I was doing, I wouldn’t try to control it.
Shelly went back to the spot where she started the week before. Maybe she was worried we would end in failure again but the thought never crossed my mind. I was Olivia, a sexy girl who was wanted.
My excited message went on the explain my idea and also about my feelings and why I thought it would work. “I didn’t tell you that night but I liked going out dressed like that,” I explained. “I don’t think I realized it then but it was exciting, like I was into it. If I just let those feelings go, I think it’ll really help me have sex like a girl with you!”
I apologized again and thanked her for being patient. She was never one for late-night messaging so I wasn’t surprised when she didn’t write back.
Finally, the next morning, “Sounds ok,” her message read, “but I don’t want to keep trying new ideas forever.”
I couldn’t blame her. “I’m sure this is it!” I wrote, “Can you come over tonight?”
“Why not here?”
“I’m going to dress up and I don’t want to leave my place if I don’t have to.”
“Ok,” she wrote, “I can come over Sunday at 8.”
That left three days – three days I didn’t want to wait but I knew better than to argue. “See you then,” was all I said.
Three days is an eternity for a sex addict and it’s way worse when you know that you’re just waiting to pass a test so that you can then arrange to get your fix. I did my best to keep my mind on work and other stuff but it was just impossible.
It was while showering that I noticed my legs. My hairy legs. Shelly will have to take off the pantyhose; How are we both supposed to think of me as a girl if I have hairy legs? Shorts season had passed so there was no harm in shaving them, which turned out to be pretty easy to do.
I must have dressed and undressed in that outfit a half-dozen times before Shelly would see me. I even put on all the makeup twice because I wanted everything to be perfect. I bought kiss-proof lipstick so that I wouldn’t get it all over Shelly when we made out. Shelly wasn’t going to give me another chance and I really needed a way to get back into that man’s house so my girlfriend could feed my burning desire for his cum.
I paced as I waited for her. In the mirror, I was a little disappointed seeing a body that wasn’t quite right. I didn’t want Shelly to have to deal with the padded panty so it was folded in a drawer in my room. I shifted my weight hoping to create the illusion of bigger hips but it wasn’t the same. That’s the night I started on the female hormones. It was impulsive and driven by my disappointment but I would continue taking them every day thereafter. I shook it off the bad feelings and tried to make use of the time and distracted myself by practicing in high heels. Shelly arrived nearly a half-hour late but I just smiled and thanked her for coming. “Sorry, I just don’t want to go out like this if I can avoid it.” She seemed to appreciate that.
As if she had remembered the game, she said, “Hello, Olivia, thanks for inviting me,” with an emphasis on the name.
I smiled, a little bashfully, as if she was being overly nice to me.
Her casual gaze turned into an analytical stare that went on uncomfortably long. “What?” I asked.
“It’s just that,” she began, “you look great, like sexy and really pretty.” Shelly seemed to be trying to figure something out and told me, “I guess I never really noticed before.”
“I wanted to make sure I got everything right.”
“It’s more than that,” she explained. Then my girlfriend adopted a let’s-be-honest tone and went on, “You know I’m not really into looks. When I met you, you were just a cute guy who was petite and, you know, into what I’m into. And when you first went out as a girl, well, I don’t know what the hell you did with all that makeup but you didn’t look like you and you really made yourself look bad. Now, though, damn… you’re really something.” She sighed, “I just never noticed before.”
“I needed the disguise when we went out but nobody’s going to see me tonight,” I explained, adding, “Nobody but you, of course.”
She looked at me once more and I felt it – the appreciation. I didn’t believe her completely but the idea that someone thought of me as sexy satisfied a need I didn’t know I had.
More than that, I was Olivia, sexy Olivia and fell into an erotic mood as a girl about to have sex.
We kissed on my couch and Shelly soon followed her standard playbook, reaching down, this time down a skirt, to find what she sought, this time a non-erection.
She hummed.
I felt wonderful. Turned-on and present. I was the girl whose name Shelly kept repeating.
The skirt was stretchy and Shelly struggled pulling it over my hips. “I can stand,” I offered, “It’ll come off easy enough since it’s just me under here.”
She helped me up and watched as I wiggled it off. “How did I not notice your hips before?” she pondered aloud.
I just answered, “I don’t really show off my body.” I didn’t want to break the mood and guessed she was talking about the pads and how different I looked with them on. “I’ll look better when we go out,” I simply said.
“Can you get the hose off, too?” she asked, “I don’t want to run them.”
As I started, Shelly huffed, “Not like that! Roll them down your legs.” She had a “don’t you know anything?” expression that I chose not to respond to.
As I got back on the couch, Shelly’s eyes went right to my legs. “You shaved?”
“I figured I should.”
“Yeah, that’s better, I think,” she agreed. I was trying to read her, worried, of course that she might just say the whole thing was too weird and bolt out of my apartment. From our first night, Shelly had shown genuine satisfaction as I ate cum. This though – me looking like a girl – was new and it was my idea. Shelly seemed to be warming up to it.
I started on the panties but her hand went to mine. “Let me,” she said in one of the rare confessions of desire that woman ever uttered. I must have looked surprised because Shelly seemed guilty or something, “What? It’s hot,” she explained. She was probably having her own doubts about her turn-ons but we would never have that conversation.
She wanted me, like not just for some rote sexual act but with real impulsive desire. Her feelings fueled mine and when she said, “I love undressing you, Olivia,” I had become something I’d never been before. I was an object of desire.
And it was intoxicating.
Shelly caressed my legs in a way she had never done before. She kissed my thigh and smiled at me. “You know you’re sort of purring,” she said softly.
I had no idea. In case I would misunderstand, she added, “I like it. It’s sexy, just like you, Olivia.”
Oh, what the hell. Whatever I was doing, I wouldn’t try to control it.
Shelly went back to the spot where she started the week before. Maybe she was worried we would end in failure again but the thought never crossed my mind. I was Olivia, a sexy girl who was wanted.
Shelly’s tongue pressed and pulsed and I purred as my arms caressed the couch cushions as if the room’s furnishings were joined in our love-making.
She called out, “Ooh, Olivia,” a few more times as I feel deeper and deeper into the fantasy.
“Hold on my little kitten,” she said as she broke contact with me. She left me highly turned-on and I’m sure she knew it. There was a confident tease in her voice when she said, “Be right back.”
I could hear my microwave running but I just laid there admiring the bosom beneath the white cashmere sweater.
“I have a treat for you,” Shelly said as she returned, “Now, close your eyes, Olivia.”
I did as she asked and soon felt it – the warm touch of a coated finger as Shelly ran cum over my red lips. “Who are you?” she teased.
“I’m a girl. My name’s Olivia.”
“What do you love, Olivia?”
“I love cum. I need it. I l-o-o-o-ve cum.”
“Mmm, that’s right. This is Don’s cum, remember Don?”
“Yes, I ate his cum before. Mmm, I love it.”
“You want more of his cum?”
“Yes, please. Don, I want your cum!”
I didn’t think it was possible but the experience was even more erotic than what I’d had before that night.
Shelly poured from the cum shotglass and went back down on me as I took a moment before swallowing. When her mouth went back to work, I whined with love for the cum as my girlfriend went back to pulsing her tongue onto me.
Shelly reached up with one hand and fondled a foam breast from atop the soft sweater. I purred and purred through the experience until purrs changed to whines, then louder whines as my climax began.
“Ahh – ahh – ahh!” I yelped. My hips bucked and Shelly held on tight to keep her strong tongue working me. I pulled at her hair and felt my body release in a starburst of ecstasy. It was almost more than I could stand.
Shelly pulled back, her face looking a bit tortured from the effort but obviously satisfied.
“Olivia!” she exclaimed, “You came!”
Not only did I come but and not only was it the single most deeply satisfying orgasm ever but my mind stayed deep inside the fantasy I had created. I was Olivia, a sexy, desired girl who was getting off. “That was amazing… so good, best ever,” was all I could say.
Pleased as any winning coach would be, Shelly summed up, “If you can come, I know you won’t get an embarrassing hard-on.” To say she was pleased was understating her expression; my girlfriend was elated.
“You wanna stay for a bit?” I asked, ready to just lay there and hold her… or possibly see if she wanted to go down on me again, but Shelly announced it was late and, as usual, would be leaving.
I started to get up but she said, “No, just relax, my little kitten. I want to look at you one last time like that.” After a pause, she noted, “You’re kind of… I don’t know… kind of slutty looking.” Another pause as I recovered from an event I would never forget and she told me, “I think I like it.”
Damn… being desired was great.
I think I had gotten some water and even gone to the bathroom before I noticed the stain on my couch. I told myself I’d need a towel next time. But then I thought about it and there wasn’t a plan for a “next time” like that. I had passed the test.
I messaged Shelly thanking her and asking, “So, are we read to go to Don’s now?”
She surprised me with a reply and answered, “We need to make sure. I can’t have you getting hard at his place. He’s been really cool so I don’t want to screw this up.”
“Ok. BTW, how did you get the shotglass full?”
“I had plans to see Don on Saturday,” she answered, “The plan was to take you but you weren’t ready so I had to go solo. He was cool about coming in it. That was great, right?”
“So great.” I didn’t pause there to ask her anything. I didn’t note that she had cheated on me. I didn’t object that my girlfriend was blowing another guy or realize that she had only blown me once. Shelly, my girlfriend, had sucked my dick exactly one time and, for that matter, had me swallow my own cum. Meanwhile, she was making plans and sucking off another guy, maybe a bunch of other guys, I didn’t know.
And I didn’t ask. It never occurred to me.
When she didn’t write back I asked, “Tomorrow?”
“Can’t. Come over Thursday and can you wax or something? You’re stubbly and it hurt my tongue.”
“You can’t come here?”
“And maybe do something about those tits? I don’t know what you’re using but I almost laughed when I grabbed it. Come on over at 8.”
And that was that.
I had successfully learned to climax as a woman. I had experienced the erotic ego shot of being the object of desire. And I would be presenting myself with convincing breasts and a silky smooth pelvis to my girlfriend later that week.
She called out, “Ooh, Olivia,” a few more times as I feel deeper and deeper into the fantasy.
“Hold on my little kitten,” she said as she broke contact with me. She left me highly turned-on and I’m sure she knew it. There was a confident tease in her voice when she said, “Be right back.”
I could hear my microwave running but I just laid there admiring the bosom beneath the white cashmere sweater.
“I have a treat for you,” Shelly said as she returned, “Now, close your eyes, Olivia.”
I did as she asked and soon felt it – the warm touch of a coated finger as Shelly ran cum over my red lips. “Who are you?” she teased.
“I’m a girl. My name’s Olivia.”
“What do you love, Olivia?”
“I love cum. I need it. I l-o-o-o-ve cum.”
“Mmm, that’s right. This is Don’s cum, remember Don?”
“Yes, I ate his cum before. Mmm, I love it.”
“You want more of his cum?”
“Yes, please. Don, I want your cum!”
I didn’t think it was possible but the experience was even more erotic than what I’d had before that night.
Shelly poured from the cum shotglass and went back down on me as I took a moment before swallowing. When her mouth went back to work, I whined with love for the cum as my girlfriend went back to pulsing her tongue onto me.
Shelly reached up with one hand and fondled a foam breast from atop the soft sweater. I purred and purred through the experience until purrs changed to whines, then louder whines as my climax began.
“Ahh – ahh – ahh!” I yelped. My hips bucked and Shelly held on tight to keep her strong tongue working me. I pulled at her hair and felt my body release in a starburst of ecstasy. It was almost more than I could stand.
Shelly pulled back, her face looking a bit tortured from the effort but obviously satisfied.
“Olivia!” she exclaimed, “You came!”
Not only did I come but and not only was it the single most deeply satisfying orgasm ever but my mind stayed deep inside the fantasy I had created. I was Olivia, a sexy, desired girl who was getting off. “That was amazing… so good, best ever,” was all I could say.
Pleased as any winning coach would be, Shelly summed up, “If you can come, I know you won’t get an embarrassing hard-on.” To say she was pleased was understating her expression; my girlfriend was elated.
“You wanna stay for a bit?” I asked, ready to just lay there and hold her… or possibly see if she wanted to go down on me again, but Shelly announced it was late and, as usual, would be leaving.
I started to get up but she said, “No, just relax, my little kitten. I want to look at you one last time like that.” After a pause, she noted, “You’re kind of… I don’t know… kind of slutty looking.” Another pause as I recovered from an event I would never forget and she told me, “I think I like it.”
Damn… being desired was great.
I think I had gotten some water and even gone to the bathroom before I noticed the stain on my couch. I told myself I’d need a towel next time. But then I thought about it and there wasn’t a plan for a “next time” like that. I had passed the test.
I messaged Shelly thanking her and asking, “So, are we read to go to Don’s now?”
She surprised me with a reply and answered, “We need to make sure. I can’t have you getting hard at his place. He’s been really cool so I don’t want to screw this up.”
“Ok. BTW, how did you get the shotglass full?”
“I had plans to see Don on Saturday,” she answered, “The plan was to take you but you weren’t ready so I had to go solo. He was cool about coming in it. That was great, right?”
“So great.” I didn’t pause there to ask her anything. I didn’t note that she had cheated on me. I didn’t object that my girlfriend was blowing another guy or realize that she had only blown me once. Shelly, my girlfriend, had sucked my dick exactly one time and, for that matter, had me swallow my own cum. Meanwhile, she was making plans and sucking off another guy, maybe a bunch of other guys, I didn’t know.
And I didn’t ask. It never occurred to me.
When she didn’t write back I asked, “Tomorrow?”
“Can’t. Come over Thursday and can you wax or something? You’re stubbly and it hurt my tongue.”
“You can’t come here?”
“And maybe do something about those tits? I don’t know what you’re using but I almost laughed when I grabbed it. Come on over at 8.”
And that was that.
I had successfully learned to climax as a woman. I had experienced the erotic ego shot of being the object of desire. And I would be presenting myself with convincing breasts and a silky smooth pelvis to my girlfriend later that week.
Appearances
As if the universe was telling me something, I kept up with the hormone pills that I had ordered on a whim. Without little thought, I continued taking them with the hope they might boost my appearance enough to keep Shelly’s desire flowing.
The breast forms were easy to find and after paying for express shipping would arrive the day before I was to see Shelly again.
I looked into waxing but read a little about it and decided it sounded way too painful. Instead, I made an appointment at a laser hair removal clinic. “Waxing can last a few weeks and, yes, it’s very painful,” the woman told me. I didn’t appreciate that selling was her job and not only signed up but added legs, armpits and face when she offered a package price. If my girlfriend was turned on to see me with bare legs, she would surely want me more once she saw that I’d gotten all my hair removed.
Tick-tock, tick-tock… time had no concern for my desire to be back on girlfriend’s couch where I was surely going to receive mind-blowing oral sex for the second time. At work, I found myself looking up makeup ideas and fall outfits in my free time (at one point, barely changing my screen in time when Ted visited). When the workday was over I was in my car driving to a shopping mall to stroll through displays of women’s clothing and shoes before I gave it any thought.
Shelly let me know that Don had agreed to another visit where I would, no doubt, experience the sexual moment of a lifetime. I would do anything to make sure it happened so when I got the impulse to get more clothes, I simply went out and bought them. Any rational person would have asked, “Do I need a second outfit?” or “Did Shelly have any complaints about my women’s clothes?”
I, however, was not a rational person; I suppose addicts aren’t supposed to be. I, was, however, starting to enjoy being Olivia and not just for the sex. I was shocked, in a good way, with Shelly’s interest in me. I felt special for the first time. And though I didn’t want to admit it, I enjoyed the thrill of going out that time in high heels, evading the neighbors and going to a stranger’s house where I presented myself as a girl.
So many emotions, so many reasons and all of them landing me in the women’s department, picking through sweaters I didn’t need, jeans I shouldn’t buy, and shoes when one pair of high heels was plenty for what I had in mind.
Still whirling as I cut off tags at home, I chuckled that at least I’d found distraction for several hours. I put the clothes away just as I began to realize I didn’t need any of them.
Maybe it was because I had too much time before our next date but it occurred to me that I really needed to pierce my ears.
As I waited at the shop the following day after work, I picked out some inexpensive jewelry thinking a bracelet or two and a few rings would complete the look. “If you don’t mind me asking, Jimmy” the girl piercing my ears began, “are you just doing this like any guy would or… or are you doing this to look like a girl.”
I wasn’t bothered. “Why do you ask?”
She aligned the tool and answered, “Well, I would have guessed you were a girl until you told me your name and, well, the long hair and everything, so, you know…”
I chuckled, “No, you’re right. It’s just something my girlfriend’s into. I’m seeing her again on tomorrow night and I want to surprise her.”
“Cool girlfriend.”
“She really is.” I chuckled again, “I even lasered all my hair off. It might be too much but it’s hard to just wait and do nothing until I can see her again.”
She laughed and answered, “Well, I’m glad it’s tomorrow. God knows how far you might change your appearance if you had more time!”
Blind to the irony, I laughed along with her. How far might I go?
The breast forms were easy to find and after paying for express shipping would arrive the day before I was to see Shelly again.
I looked into waxing but read a little about it and decided it sounded way too painful. Instead, I made an appointment at a laser hair removal clinic. “Waxing can last a few weeks and, yes, it’s very painful,” the woman told me. I didn’t appreciate that selling was her job and not only signed up but added legs, armpits and face when she offered a package price. If my girlfriend was turned on to see me with bare legs, she would surely want me more once she saw that I’d gotten all my hair removed.
Tick-tock, tick-tock… time had no concern for my desire to be back on girlfriend’s couch where I was surely going to receive mind-blowing oral sex for the second time. At work, I found myself looking up makeup ideas and fall outfits in my free time (at one point, barely changing my screen in time when Ted visited). When the workday was over I was in my car driving to a shopping mall to stroll through displays of women’s clothing and shoes before I gave it any thought.
Shelly let me know that Don had agreed to another visit where I would, no doubt, experience the sexual moment of a lifetime. I would do anything to make sure it happened so when I got the impulse to get more clothes, I simply went out and bought them. Any rational person would have asked, “Do I need a second outfit?” or “Did Shelly have any complaints about my women’s clothes?”
I, however, was not a rational person; I suppose addicts aren’t supposed to be. I, was, however, starting to enjoy being Olivia and not just for the sex. I was shocked, in a good way, with Shelly’s interest in me. I felt special for the first time. And though I didn’t want to admit it, I enjoyed the thrill of going out that time in high heels, evading the neighbors and going to a stranger’s house where I presented myself as a girl.
So many emotions, so many reasons and all of them landing me in the women’s department, picking through sweaters I didn’t need, jeans I shouldn’t buy, and shoes when one pair of high heels was plenty for what I had in mind.
Still whirling as I cut off tags at home, I chuckled that at least I’d found distraction for several hours. I put the clothes away just as I began to realize I didn’t need any of them.
Maybe it was because I had too much time before our next date but it occurred to me that I really needed to pierce my ears.
As I waited at the shop the following day after work, I picked out some inexpensive jewelry thinking a bracelet or two and a few rings would complete the look. “If you don’t mind me asking, Jimmy” the girl piercing my ears began, “are you just doing this like any guy would or… or are you doing this to look like a girl.”
I wasn’t bothered. “Why do you ask?”
She aligned the tool and answered, “Well, I would have guessed you were a girl until you told me your name and, well, the long hair and everything, so, you know…”
I chuckled, “No, you’re right. It’s just something my girlfriend’s into. I’m seeing her again on tomorrow night and I want to surprise her.”
“Cool girlfriend.”
“She really is.” I chuckled again, “I even lasered all my hair off. It might be too much but it’s hard to just wait and do nothing until I can see her again.”
She laughed and answered, “Well, I’m glad it’s tomorrow. God knows how far you might change your appearance if you had more time!”
Blind to the irony, I laughed along with her. How far might I go?
Shared Interest
When I picked out the hormone treatment that was in my kitchen, I bought it because it promised fast results, like the kind you couldn’t get legally. Taking the pills was reckless but I would have stopped if anything bad started to happen. I was on my third day when I’d finally go to Shelly’s dressed as a woman. My chest felt sensitive and tender but certainly not enough to worry about.Those pills came in an unmarked box which saved me from explaining anything to the nosy woman who received packages for us at our building. I was back there again to receive another important and, thankfully, unmarked, box the day I’d leave my unit all alone in heels for the first time.
The manager looked up from her magazine only long enough to recognize me and pointed to a stack where I’d find the parcel. As I looked, one of my other neighbors, a sleight guy with blond hair named David walked in.
I knew of this guy because he was the only person to try to befriend me and he also complained about Paul and Enrique. There was some recent drama about a robbery or something and the rumor mill connected his name to it. He said hello to me but I just politely smiled, that guy seemed like a jerk. As much as I needed friends, I wasn’t that desperate.
I heard him asking about someone named Foxx or something and then he joined me at the package stack. In my package were the breast forms and I was thankful nobody could know what I was collecting that day. David, as it turns out, was also collecting something secret but that’s another story.
Once back in at my place, I opened my mail-order arrival and held them, impressed me with their appearance. Naturally shaped and weighty, the big forms filled out the bra I put on and gave to the pressure of my hand as I touched them. With my sweater on, Shelly might just have a hard time telling them from real ones, I guessed.
My sweater… yes the original white sweater. I decided that the original outfit was the best since a skirt was more feminine and if I added the wig, I’d surely look like a woman if anyone saw me. I just needed to avoid any eye contact with the neighbors.
So, no, I didn’t need the new clothes that were now in my bedroom, tags removed and unable to be returned. I got dressed, rolling the pantyhose up my legs like Shelly taught me. I was starting to feel comfortable with eye liner and lipstick. Applying eye shadow and blush still seemed like an art I hadn’t mastered but I felt Shelly would be pleased.
Sneaking out to my car was easy and I laughed at myself for worrying once I was in it because it was rare to see any of my neighbors and only a few knew me. I even drove extra carefully, worried about the ramifications of an accident or moving violation. Still, the care of rolling up the pantyhose, the detail work of the makeup and fretting over making my escape completely occupied my thoughts.
It wasn’t until I was at Shelly’s door that I let myself relax and feel the joy.
Olivia… I was Olivia, out in my skirt and high heels. I was Olivia, at my girlfriend’s door. I was Olivia, about to be ravished and admired. Goosebumps.
“Hey,” Shelly said before I could get inside, “Your hair!”
“Like it?”
She closed the door behind me and that girl just looked infatuated. “I didn’t know you got a wig!”
“I thought I mentioned it.”
“It looks fantastic. You have got to grow your hair.”
I actually thought, “Not like I can do that in a few days,” but I just nodded instead.
As if correcting course from the distraction, Shelly said, “Nice to see you Olivia. Want to sit down?”
Indeed, I did. I wanted to sit down. I wanted her to seduce me. I wanted to get a mouthful of Don’s cum. I wanted her to bring me to a second outrageously awesome climax. “Sure,” was all I said.
Shelly’s hand moved across my tummy to my waist and seemed to express a desire to slide up but paused with knowing disappointment if it did. Shelly’s mood was quiet and highly aroused. That girl was clearly turned on and I felt light pressure from her hand next to the breast form.
In my bedroom voice, I whispered, “You can touch me.”
As her hand began to move, Shelly told me that she loved my soft sweater. I tingled as I waited for her reaction to the new forms which would surely be pleasing.
Sometimes it seemed that Shelly didn’t really like kissing, like it was just a means to an end. We never kissed hello or goodbye and it never felt like a show of affection. But she would never get her mouth on a soft penis so we’d kiss until I was ready. When I watched her with Don, she seemed the same, like she was making out just because she had to. Shelly’s lips met mine as I fell back in her couch. Her hand accepted my invitation, grazing over the full breast and then lightly cupping it. The softness of the breast form was augmented by the cashmere and Shelly broke our kiss to moan the name I’d adopted.
Back to kissing, my lover seemed more alive and we kissed with enthusiasm that seemed genuine for the first time. Or maybe it was all me because Shelly’s touch lit a fuse that sparked its way to an image of me with real breasts, topless and being seduced by a lover with lust for my new body.
Shelly’s lips moved to my ear and she whispered, “I love them,” as her hand explored atop the soft sweater.
I purred with delight.
As we kissed on my girlfriend’s couch that night, I had no idea that I would eventually have the breasts in my vision. I had no idea that Shelly would never see me in men’s clothing again. I simply had no appreciation for what my love of cum was doing to me.
Shelly was horny and my mind had moved on. I was no longer thinking about the breasts that would look and feel so right on me. Instead, “Do you have my shotglass?” I asked.
Our sexual journey had refined my desires but we hadn’t explicitly stated what that meant and where I was headed. We still wouldn’t know that night but we were just one encounter away.
Surprize Move
“I’m so sorry, Olivia,” Shelly pouted, “but I don’t have any for you.”
I suppose she was expecting me to just nod and understand but the skirt, the heels, and her touch on my sweater had gotten me in a mood that was shattered by her news.
“It’s okay, Honey,” she tried, “I can give you yours, you know, like we used to.”
I winced. “Not tonight,” I answered, unwilling to confess to her that my desires had graduated.
As girlfriends go, Shelly got the highest marks for sex, sexual adventure, and even though she failed me that night, for doing all the work with other men to give me what I wanted.
When it came to any standard girlfriend stuff, Shelly only managed not to disappoint because I expected nothing. She was awful at returning calls, showed up late, and never wanted to talk.
That night, though, she showed some creativity as a compromise to the problem that was obvious given my let-down. “Hey, I know, how about dessert?” was how she started it.
There I was, breathing heavily and wanting that special silky liquid and she… dessert? “Just wait there,” she said coyly after reading my reaction.
She was quick in her kitchen and I heard her microwave going. Was she just toying with me to see how much I wanted more of Don?
Sadly, no, she wasn’t returning with my shotglass. Instead, she carried a bowl of, what was that, milk?
“I think you’ll like this dessert, Olivia,” she said, adding “Olivia” as if that earned her extra credit. In her other hand, she carried a few strawberries.
I laid back as she told me. “Now, open up those pretty lips, Honey,” she said as I saw her dip the berry.
That girl had a solid grasp on kinky, that much was sure. She hummed as warm cream dripped into my mouth and onto my lips. “That’s so nice, Olivia.”
She set the bowl on the floor and held the dripping berry near my open mouth as her other hand slid beneath the pantyhose producing another hum. “I love this,” she oozed, touching my panty, no erection to be found.
Shelly flipped down the back of the ankle strap and eased my shoes off as I let the warm cream slide inside of me and imagined my girlfriend had delivered it directly from an ejaculating cock.
As if knowing exactly what I needed next, Shelly put down the strawberry and moved to take off my skirt. “You wish that was his cum, don’t you Olivia?”
“I want it so bad!”
I lifted my ass and off went the tight skirt. “You love cum, don’t you Olivia?”
“I love cum, I love it!”
The cream had helped and our words, especially mine, were making me so horny I’d treat us both to something special that night.
Shelly would take her time with my pantyhose but kept me talking. “I’ll bet you can’t wait to show Don your new hair, can you Olivia?”
“I hope he likes it. I think he likes me, do you?”
“He told me you’re sexy and loved seeing you with lipstick on. He doesn’t care you’re a boy, you know.”
I whined at the thought that another man was into me.
“Hmm,” she hummed, this time quizzically, “this is going to take some work.”
“I wanted to look good for you,” was my answer to her complaint about the padded panty with its laced-up waist cincher. I knew it wasn’t an attractive garment.
She seemed to understand. “And you do,” she told me as she found the tie.
Naked but for a cashmere sweater, I felt a finger, just one finger, as it trailed up my bare leg. Still humming, Shelly told me that I’d “like it better with these on” as she put the high heels back on my feet.
Then, “Here,” was all she said as she pulled a towel from beneath the couch and moved it to my ass. I lifted up and let her slide it beneath me. The cream might have been inspired but the waiting towel was standard Shelly – always prepared and planned out.
It seemed like we were ready, god knows I was ready. I spread my legs, waiting for my girlfriend to get down and tongue me to a much-needed climax.
Instead, though, Shelly knelt on the floor near my shoulder. She brought back another dripping berry with her left hand and, with her right, felt my bare pelvis. Humming, more humming as she watched me take the running warm cream into my mouth. Her fingers began pressing and rolling and it took me a while to realize…
She was going to get me off by fingering my spot.
Her firm digits rolled and pulsed and my lips quivered as I thought of cum from another man dripping into me. Shelly’s words completed the moment. “You’re so beautiful, Olivia. Guys will love coming for you.”
Though I’d lost track of the time, I know it wasn’t long. “Ooh!” I moaned as the sensation took over then, “Ahh!” as I felt cum rushing onto the towel. But then everything got frantic. Shelly’s hand had been pulsing fast and she started to slow as the flood began but my mind was on sexual overdrive. “Don’t stop!” I called out with the sort of desperation that suggested a life might be at stake. “Don’t stop!”
Her fingers kept it up. Every exhale was a feminine whine as my hands slid down to my smooth hips, not knowing what to do. “So gooooooood!” I called out. My hands found a home atop my white sweater and squeezed the breasts I imagined I had beneath it. “Ahh!” I called out a second time as my body reacted with a second climax.
Shelly could only say my name, rather, the name I’d adopted.
I recovered alone on her couch. Her next words were, “Jimmy, that was hot,” and “After you wipe yourself off, just roll up the towel dry-side-out and leave it on the floor.”
She took the bowl and was cleaning up in the kitchen as I got dressed.
“Shelly, I just…” I started to tell her, “I mean…”
Swirling around, but unable to form words, were thoughts of delight, of surprise, and of selfish desire to plan our next time.
“The waxing was great, by the way, you should absolutely keep that up,” she called from the kitchen, “I’m free Saturday.”
“Saturday would be great.”
“Can you come here again?”
I was over my fear of getting caught and had just started to enjoy the thrill of being out in makeup. “Sure.”
As I turned, Shelly snickered a little. She noted, “I didn’t notice that before. Cute hose.”
I smiled, knowing she just saw that the pantyhose I’d bought had the word “LOVE” running down the right calf. “Yeah, I didn’t know when I bought them, I guess I was in a rush. I’m new at this, you know.”
“Cute,” she said again and I smiled. Shelly and I would never use “love” to describe our feelings for each other. We never would fall in love, I knew that and I guessed Shelly did, too. Even though we wouldn’t know love, our relationship had led me to buying, and then wearing, pantyhose that broadcast the term. The irony is that I would later wonder if wearing those hose might put me on a path to find the love of my life.
“It’s great that you don’t mind dressing the way you do,” Shelly noted, “It’s perfect for our game.”
I shrugged. I thought the skirt and sweater outfit was fine, like the sort of thing Olivia might wear to work (as if I thought that would ever happen!). “I dunno, this seems nice, I think.”
“Jimmy, the only girls who dress like that are sluts who no guy’s ever going to take seriously. I had a guy who wanted me to go out looking like that and he turned out to be a total creep – you know, the kind of psychopath who’s unable to have a normal relationship?”
I just shrugged again. “It’s just a sweater and a skirt.”
She shook her head. “All too tight and that skirt looks like leather…” then she added, “and the heels and…” she snickered. “It’s fine. It’s perfect, Jimmy. Not like any guy’s going to take you seriously anyway.”
“See you at eight?” I asked.
“See ya then, Jimmy.”
I suppose she was expecting me to just nod and understand but the skirt, the heels, and her touch on my sweater had gotten me in a mood that was shattered by her news.
“It’s okay, Honey,” she tried, “I can give you yours, you know, like we used to.”
I winced. “Not tonight,” I answered, unwilling to confess to her that my desires had graduated.
As girlfriends go, Shelly got the highest marks for sex, sexual adventure, and even though she failed me that night, for doing all the work with other men to give me what I wanted.
When it came to any standard girlfriend stuff, Shelly only managed not to disappoint because I expected nothing. She was awful at returning calls, showed up late, and never wanted to talk.
That night, though, she showed some creativity as a compromise to the problem that was obvious given my let-down. “Hey, I know, how about dessert?” was how she started it.
There I was, breathing heavily and wanting that special silky liquid and she… dessert? “Just wait there,” she said coyly after reading my reaction.
She was quick in her kitchen and I heard her microwave going. Was she just toying with me to see how much I wanted more of Don?
Sadly, no, she wasn’t returning with my shotglass. Instead, she carried a bowl of, what was that, milk?
“I think you’ll like this dessert, Olivia,” she said, adding “Olivia” as if that earned her extra credit. In her other hand, she carried a few strawberries.
I laid back as she told me. “Now, open up those pretty lips, Honey,” she said as I saw her dip the berry.
That girl had a solid grasp on kinky, that much was sure. She hummed as warm cream dripped into my mouth and onto my lips. “That’s so nice, Olivia.”
She set the bowl on the floor and held the dripping berry near my open mouth as her other hand slid beneath the pantyhose producing another hum. “I love this,” she oozed, touching my panty, no erection to be found.
Shelly flipped down the back of the ankle strap and eased my shoes off as I let the warm cream slide inside of me and imagined my girlfriend had delivered it directly from an ejaculating cock.
As if knowing exactly what I needed next, Shelly put down the strawberry and moved to take off my skirt. “You wish that was his cum, don’t you Olivia?”
“I want it so bad!”
I lifted my ass and off went the tight skirt. “You love cum, don’t you Olivia?”
“I love cum, I love it!”
The cream had helped and our words, especially mine, were making me so horny I’d treat us both to something special that night.
Shelly would take her time with my pantyhose but kept me talking. “I’ll bet you can’t wait to show Don your new hair, can you Olivia?”
“I hope he likes it. I think he likes me, do you?”
“He told me you’re sexy and loved seeing you with lipstick on. He doesn’t care you’re a boy, you know.”
I whined at the thought that another man was into me.
“Hmm,” she hummed, this time quizzically, “this is going to take some work.”
“I wanted to look good for you,” was my answer to her complaint about the padded panty with its laced-up waist cincher. I knew it wasn’t an attractive garment.
She seemed to understand. “And you do,” she told me as she found the tie.
Naked but for a cashmere sweater, I felt a finger, just one finger, as it trailed up my bare leg. Still humming, Shelly told me that I’d “like it better with these on” as she put the high heels back on my feet.
Then, “Here,” was all she said as she pulled a towel from beneath the couch and moved it to my ass. I lifted up and let her slide it beneath me. The cream might have been inspired but the waiting towel was standard Shelly – always prepared and planned out.
It seemed like we were ready, god knows I was ready. I spread my legs, waiting for my girlfriend to get down and tongue me to a much-needed climax.
Instead, though, Shelly knelt on the floor near my shoulder. She brought back another dripping berry with her left hand and, with her right, felt my bare pelvis. Humming, more humming as she watched me take the running warm cream into my mouth. Her fingers began pressing and rolling and it took me a while to realize…
She was going to get me off by fingering my spot.
Her firm digits rolled and pulsed and my lips quivered as I thought of cum from another man dripping into me. Shelly’s words completed the moment. “You’re so beautiful, Olivia. Guys will love coming for you.”
Though I’d lost track of the time, I know it wasn’t long. “Ooh!” I moaned as the sensation took over then, “Ahh!” as I felt cum rushing onto the towel. But then everything got frantic. Shelly’s hand had been pulsing fast and she started to slow as the flood began but my mind was on sexual overdrive. “Don’t stop!” I called out with the sort of desperation that suggested a life might be at stake. “Don’t stop!”
Her fingers kept it up. Every exhale was a feminine whine as my hands slid down to my smooth hips, not knowing what to do. “So gooooooood!” I called out. My hands found a home atop my white sweater and squeezed the breasts I imagined I had beneath it. “Ahh!” I called out a second time as my body reacted with a second climax.
Shelly could only say my name, rather, the name I’d adopted.
I recovered alone on her couch. Her next words were, “Jimmy, that was hot,” and “After you wipe yourself off, just roll up the towel dry-side-out and leave it on the floor.”
She took the bowl and was cleaning up in the kitchen as I got dressed.
“Shelly, I just…” I started to tell her, “I mean…”
Swirling around, but unable to form words, were thoughts of delight, of surprise, and of selfish desire to plan our next time.
“The waxing was great, by the way, you should absolutely keep that up,” she called from the kitchen, “I’m free Saturday.”
“Saturday would be great.”
“Can you come here again?”
I was over my fear of getting caught and had just started to enjoy the thrill of being out in makeup. “Sure.”
As I turned, Shelly snickered a little. She noted, “I didn’t notice that before. Cute hose.”
I smiled, knowing she just saw that the pantyhose I’d bought had the word “LOVE” running down the right calf. “Yeah, I didn’t know when I bought them, I guess I was in a rush. I’m new at this, you know.”
“Cute,” she said again and I smiled. Shelly and I would never use “love” to describe our feelings for each other. We never would fall in love, I knew that and I guessed Shelly did, too. Even though we wouldn’t know love, our relationship had led me to buying, and then wearing, pantyhose that broadcast the term. The irony is that I would later wonder if wearing those hose might put me on a path to find the love of my life.
“It’s great that you don’t mind dressing the way you do,” Shelly noted, “It’s perfect for our game.”
I shrugged. I thought the skirt and sweater outfit was fine, like the sort of thing Olivia might wear to work (as if I thought that would ever happen!). “I dunno, this seems nice, I think.”
“Jimmy, the only girls who dress like that are sluts who no guy’s ever going to take seriously. I had a guy who wanted me to go out looking like that and he turned out to be a total creep – you know, the kind of psychopath who’s unable to have a normal relationship?”
I just shrugged again. “It’s just a sweater and a skirt.”
She shook her head. “All too tight and that skirt looks like leather…” then she added, “and the heels and…” she snickered. “It’s fine. It’s perfect, Jimmy. Not like any guy’s going to take you seriously anyway.”
“See you at eight?” I asked.
“See ya then, Jimmy.”
Ready, So ready
Shelly had a plan, a plan to get me ready for a return to another man’s house (presumably Don’s). It wasn’t for me to question her and after learning she could finger me to orgasm, I easily let her continue with complete control.After work, I spent Friday evening practicing with makeup and pondered more changes. Should I do more eyebrow plucking? Do I need another piercing? Should I grow out my fingernails? What would guys like to see? What would turn them on?
I tried on all my clothes and moved in front of the mirror, treating it to playful teases and suggestive poses. When it came time for bed, I reluctantly took off the bra but pulled back the covers with my panties still on.
There, I did exactly what any guy would do after discovering he can get off in a new way. After hours of being Olivia, I slid my hand down my body and found the place Shelly had rubbed with such expert gyrations.
The purring began and my fingers found the magic. In my mind, I flashed back to the reflection in the mirror as Olivia pouted and played, getting the boys turned on and ready for her. I used Shelly’s technique and spoke aloud, “I want cum, I want it so bad!”
When I started to cum, it shocked me so much that I couldn’t really enjoy the ride. Instead, my heartbeat spiked at the realization and, since I’d been talking aloud, I called out, “I’m coming!”
Though I missed my chance to really enjoy my first auto-erotica as a girl, that wouldn’t be the case for the second… or the third. Each subsequent orgasm was less messy but even more satisfying. Shelly had opened the door to yet another wonderful world. I didn’t so much walk through that door as packed up all of my belongings and sense of self, crossed the threshold, and set up camp.
I woke on Saturday and gave thought to letting my hand go south yet again but laughed it off and said, “You’ve got things to do!” forcing myself to start my day.
After taking the hormone pills that had become part of my routine, I’d exercise, then set off to the mall.
Clearly, I needed more panties and should have a spare to put on after my time with Shelly in case she wanted them on while fingering me. I didn’t like sleeping in just the simple panties I had on the night before. I knew that, with a little help, my feminine fantasy could be better. And there was no way I had enough makeup; I was sure of that.
After getting a new outfit, I spent far too much time buying the bras, panties, and teddies I would wear to bed. In my defense, I found not one, but two of those buy-one-get-one-free sales when I went lingerie shopping. I told myself I was just a victim of effective marketing as my new purchases covered my entire bed that afternoon.
It had been my last time out shopping while dressed as a boy and I’d bought more lingerie on one trip than I ever would again. Irony, so much irony.
I told Shelly that I had other outfits, “If you’d like to see me in something else tonight,” but she didn’t reply. It was good enough, I guessed, that I had offered. She did like me in my white sweater…
I probably shouldn’t have but sent another message asking, “Maybe I should show you the other sweater I got in case you think Don would like it better?” and when she didn’t reply, I felt a little silly for even asking. Shelly had a life outside of me and, unlike me, wasn’t obsessed about my need for sex.
My need for sex… by that autumn, I had found a way to drone through the workday with just enough productivity to keep my job. I wouldn’t let myself search for women’s clothing or makeup tutorials or anything that would get me in trouble. Nonetheless, feminine sensibilities had completely taken over. I found myself walking with a sway all the time. My hand gestures had come to include a softly bent wrist. Always prone to light giggles, I stopped fighting them and gave up trying to sound masculine when I laughed.
People at work and others were noticing but most were invisible to me; they just faded as if they were no longer part of my world. “I’m just in a good mood,” I explained to Ted when he asked.
But the moment I was home, I fell into Olivia’s world and that’s how my future really began to change. What had started as a necessary costume had become a new desire that rode along like a sidecar on the cum-fueled motorcycle that drove me down the streets of passion, desire, lust, and reward.
One of my additions, a new panty, padded my hips and ass and pulled in my waist but with a more subtle lace-up front. I hoped Shelly wouldn’t be as bothered seeing it as she was by the clunky one I had worn to her place. “I got a new padded corset,” I wrote to her, “but I don’t have to wear one if that’s better.”
It was a trade-off. I’d either look better or avoid an awkward moment just when our sex was near its hottest.
Shelly didn’t write back but I looked at my body with the new panty on and convinced myself she’d be okay with it. I really liked the way it added the curves that that fit Olivia’s ideal.
Growing up, I had no interest in my body in any way. I didn’t exercise, didn’t try, and had no physical self-image or even awareness.
Oh, sure, I was picked on for being little. “Scrawny” was often used to describe me but the insults barely registered. High schoolers like to pick on others but thankfully, anyone older is usually over that so I left home and entered a world where the worst thing people might do was ignore me. The immature guys down the hall seemed to embrace a frat-boy mentality and they were the exception. They actually brought back “scrawny” to describe me with their insults but I would just lower my head and scoot away.
I was going through life without a care or thought about how I looked.
Shelly, however, was changing that. She liked the way I looked and I could tell she meant it when she told me so. And then there was Don. Did he really think I looked sexy? Me? Sexy? What guy wouldn’t want more of that?!!!
I had started a new exercise routine, was dutifully taking an excess of female hormones and had a drawer of lingerie that would keep my mind on my Oliva persona every possible moment. In a new dress and heels, my hips and ass rounded by my latest purchase, I snuck out of my apartment and headed over for another trip to hedonism.
Shelly was right to hesitate before taking me back to Don’s. She was getting me ready so it would be perfect and I was ready, so ready, to get more training.
Ready!
Even though I wore a sweaterdress, the October air told me I’d soon be investing in a woman’s coat if I was going to keep up this game. I took note as I walked briskly to my car, my head turning left and right, scanning for neighbors.Maybe Shelly would lend me a coat, I wondered as I walked up her steps, but dismissed the question. The last thing I needed was to have her see me as a burden. She didn’t seem to want me wearing her stuff. I paused at the door and exhaled.
So ready…
I knocked but no answer, then knocked again. I messaged her and waited, wearing a dress, in her hallway. It soon became unnerving.
“About five minutes,” was her reply. No reason, no apology.
“You know I’m wearing a dress, right?”
No reply. No reason. No apology. I offered a polite nod and a smile that I said, “Please don’t talk to me,” when one of her neighbors came home before she did.
“Jimmy?” I heard as she walked up the steps. She unlocked the door and went in before me.
In I went, ready for more.
Shelly was wearing jeans and a t-shirt, her usual at-home outfit but there was something different. Lipstick. Her lips were a carefully painted purple, something I’d not seen at her place since the night I met her. Except for dressing up to go see Don, she was like one of those feminists who made a point of downplaying the fact they were women. I was sure she had on lipstick the night we met – and heels. It was flattering to think she dressed up that night to ensnare me and I had no regrets even if it wasn’t the real Shelly.
After setting a bag on the kitchen counter, she turned to me as if I was the next item on a to-do list. Shelly’s role in my journey was often predictable, like the dirty talk that freed me from any guilt I might have developed for my love of cum, her actions were no surprise, just perfectly timed nudges to make me horny. The fact that hearing my own words proclaim a desire for another man’s fluid would help convince me that the way I was headed was right and reasonable was just an added benefit.
Likewise, the way she got me to hide my dick and then taught me to get off without an erection were all just obvious steps. At least looking back, they were.
But that night, as she greeted me with model-ready lips, Shelly would surprise me.
“Olivia!” She exclaimed when she saw me, “Is that a new dress?”
“You like it?”
“Uh… well, hell yeah… it’s just… I thought you’d only have the one outfit.”
Sometimes I wondered if that girl even read my messages. “Normal hose, too,” I said as I turned around for her. “Not too tight, is it?”
“It’s sexy, Olivia. Pretty gutsy for a guy like you to go out in it!”
I wanted to tell her she didn’t need to keep using my name so much. It was obvious what she was trying to do.
“Come here, my little kitten,” she said as she sat down.
I had thought about telling Ted from work, about Shelly. I would tell him that our dates always start later in the evening, always at her place or mine and that Shelly wastes no time in getting us kissing on the couch. I would tell him that we’re deep into sex by a quarter past eight every night and I’m home by nine with one more memory of one more incredible encounter. But Ted might ask for details and, so, no, I hadn’t mentioned Shelly to him. He asked what happened with the girl I met at company happy hour and I had just answered, “Nothing much. It didn’t work out.” That was just days after I’d swallowed cum for the first time and I was too afraid of anyone finding out. I also had no idea that I was starting a relationship so my one friend would never know what had become of that encounter.
“So pretty,” she told me as she played with my hair.
The kissing and petting began predictably. “I love your tits,” she whispered as she explored them with a bit more vigor than the last time. I hummed with the satisfaction of one of the better purchasing decisions of my life as my girlfriend caressed and squeezed.
Without thinking about it, “I love the way you touch me,” I answered.
She paused and gave my breast one more light caress before looking at me and softly asking, “Kiss me. Kiss me Olivia.”
I leaned forward and softly planted my lips on hers. I felt Shelly’s breath, then her hand over my stockings on my thigh. I kissed her more fully and Shelly responded with the same but pulled back after a moment.
She had a look that was hard to describe. Was it surprise? Excitement? Whatever it was, she seemed to have made a discovery.
“You know what I think?” she asked in a way that suggested she liked the answer and liked teasing me with the question.
“What?”
“I think you don’t like kissing girls much anymore.”
“What are you talking about?” I asked. Suddenly it seemed there was a speedbump in my path. I had arrived at her door hoping she had refilled my shotglass. But… what was this about my kissing?
She nodded. “I can tell… Olivia,” she said the same with emphasis, “Ever since you’ve been dressing up. You’ve changed, like you’re just not into it.”
“Of course I am.”
There was that expression again, only a stronger version of whatever I was supposed to read from it. She shook her head. Oddly, she wasn’t bothered. “I thought maybe you needed me in lipstick but nope.”
She put on lipstick for me? “Shell, I’m totally into it.”
“Nope.”
“You’re crazy.”
“You know what?” she teased.
“What?”
“I think you’d rather be kissing a guy.”
And… there it was. That was my girlfriend’s first hard turn just when I thought I saw our path ahead.
Guys?
Break!
“Shelly!”
With her typical carefree smile, she told me, “Hey, I don’t care. It’s hot.”
Then she got up. Like, just stood up as we were moving on. My girlfriend announced that she felt I would rather kiss another man then got up as if we were a normal couple who had just decided on Italian for dinner.
She turned from the kitchen and said, “I’ve got dessert for you…” adding, “Olivia.”
“How about something different tonight?” she asked as she moved around in the kitchen, “Can you get out of that dress and your girdle thing?”
It seemed we were not going to talk about what gender I liked to kiss. Lipstick? I shook my head, realizing she had worn the lipstick as if to make it more clear I was kissing a girl. I had to let it go. We had plans and Shelly was moving onto the next step regardless of whatever had just happened after kissing with lipstick on for only the second time.
I reached back and unzipped the dress. “I got a new one, you know, I’ll show you.”
“That’s great,” Shelly answered in a way that let me know she wasn’t listening to me.
I got out of the dress and rolled down my hose. Shelly was joining me just as I finished. “I thought it was white?,” she asked, then seemed to be thinking. She said, “I wonder… why don’t you leave it on. Want to put your heels back on?”
“I know it’s silly because I’m just lying down but I do like the way they feel,” I said as I buckled the ankle strap of the shoes. The green suede was tacked with little brass nails to an all-wood lower that had a one-inch platform and a six-inch heel. I liked the way they added some subtle style to the snug but simple maroon dress and had found greenish hose to tie the outfit together.
“You’ve probably just seen too many pictures of sexy girls wearing high heels in bed,” she reasoned. She was probably right. My image of what sex appeal was had been created by the very best in mainstream erotica. I finished with the little brass buckles and laid back.
“There’s a towel under the couch,” she announced. I reached down and placed it under me.
“Do you have…” I began to ask.
“Sorry, Olivia. I went over there but he had to cancel. Next time, I promise,” was her disappointing reply.
“How about a little more fruit?” she teased, producing a banana.
I wasn’t going to get grouchy. She had surprised me with the cream last time and I liked it. “Let’s try chocolate this time for my sexy little kitten.”
She dipped the peeled banana and I opened up to take the hot chocolate sauce. While it tasted better than the cream, it also didn’t taste anything like what I wanted.
Shelly tried to make up for it with her words.
“Have you been thinking about cum?” she asked softly.
I moved my head in a small nod as the sauce dropped into my open mouth.
She seemed to understand and was pleased to know my answer. “I want to give it to you,” Shelly told me, “I want to feed you cum.”
Explicit and sexual. That girl knew how to get me going. “Here, take this,” she asked, bringing my hand to the banana.
As her hand untied the panty, Shelly noted, “You know, I do like these. They’re different, right?”
“I hoped you’d like them better.”
“And…” she began, then paused and her hand slid down the front of the untied garment, “I can get down here without taking them off…”
“Mmm,” I hummed.
Her fingers slowly probed for the exact spot. “Mmm, that’s it,” I told her.
“You just enjoy your dessert, Olivia,” she said in reply. Her fingers easily found home and went to work.
As her fingers started to rub, she asked me to, “Take it in your mouth,” in a way that suggested she was inspired in the moment and finding a new kink, “Yeah, let me see you suck it.”
Her hand was magic and I parted my lips to softly let the banana past.
She said my name, my girl name, a few more times. I slowly raised and lowered my head to let my lips ride up the banana as I held it steady. Mmm… mmm…
Either her fingers were particularly hot that night or something else was stoking the flames because I only lasted a few minutes before the quivering began.
Then it started to come over me. Trembling, I broke the banana in half as my orgasm took control of all motor functions. Shelly’s hand didn’t let up and I whined non-stop. “Come again!” she called out almost like it was a demand or an impatient request.
I let go of the fruit and grabbed hold of my bra and the heavy forms within it. I could hear Shelly’s breath as she rubbed me furiously. “Ahhh!” I called out as the second wave hit. Shelly slowed until I was done, then pulled out her hand.
“I love watching you get off, Olivia,” she told me, “Damn, it’s sexy.”
Her next words were, “Hey, you dripped chocolate sauce on my carpet, you know.”
“Sorry.”
She seemed overly upset. It’s not like it was my idea. Talking to herself, “I think I need to blot it first,” she said as she took the bowl and banana pieces to her kitchen.
That was my cue to get dressed and the first thought I had was that my panties were soaked and though I had thought about bringing a spare, I didn’t have a good way to carry them so didn’t.
“Sorry again about your carpet.”
“I think I can get it out.”
I was adjusting the pantyhose when she told me, “I’m headed out for a little break, then home for the holidays.”
She had told me that, like me, she could work from home sometime so I asked, “Thanksgiving? You’re going early?”
She worked on the stain which, really, looked like two or three little drops.
“Yeah, staying through Christmas and New Years. My folks need some help around the house.”
I pulled up the dress and found the sleeves. “That long?” I asked.
“Yeah, my dad fell and my brother’s a piece of shit.”
Dad fell… brother… I didn’t even know she had a brother. I looked at her in shock as if I didn’t know she had a dad either. “Wow, Shelly, that’s rough. Sorry.”
“There,” she announced, standing, “wasn’t so bad.” She was looking down, pleased to see we’d not left any permanent marks from our latest kinky encounter.
“Can you zip me?” I asked, turning away.
“It’s been wild few weeks, Jimmy. Let’s pick up where we left off, k?”
There was only one reply to that. “I can’t wait.”
She opened her door and her last words were, “And don’t cut that hair!”
And just like that, we were on a break.
With her typical carefree smile, she told me, “Hey, I don’t care. It’s hot.”
Then she got up. Like, just stood up as we were moving on. My girlfriend announced that she felt I would rather kiss another man then got up as if we were a normal couple who had just decided on Italian for dinner.
She turned from the kitchen and said, “I’ve got dessert for you…” adding, “Olivia.”
“How about something different tonight?” she asked as she moved around in the kitchen, “Can you get out of that dress and your girdle thing?”
It seemed we were not going to talk about what gender I liked to kiss. Lipstick? I shook my head, realizing she had worn the lipstick as if to make it more clear I was kissing a girl. I had to let it go. We had plans and Shelly was moving onto the next step regardless of whatever had just happened after kissing with lipstick on for only the second time.
I reached back and unzipped the dress. “I got a new one, you know, I’ll show you.”
“That’s great,” Shelly answered in a way that let me know she wasn’t listening to me.
I got out of the dress and rolled down my hose. Shelly was joining me just as I finished. “I thought it was white?,” she asked, then seemed to be thinking. She said, “I wonder… why don’t you leave it on. Want to put your heels back on?”
“I know it’s silly because I’m just lying down but I do like the way they feel,” I said as I buckled the ankle strap of the shoes. The green suede was tacked with little brass nails to an all-wood lower that had a one-inch platform and a six-inch heel. I liked the way they added some subtle style to the snug but simple maroon dress and had found greenish hose to tie the outfit together.
“You’ve probably just seen too many pictures of sexy girls wearing high heels in bed,” she reasoned. She was probably right. My image of what sex appeal was had been created by the very best in mainstream erotica. I finished with the little brass buckles and laid back.
“There’s a towel under the couch,” she announced. I reached down and placed it under me.
“Do you have…” I began to ask.
“Sorry, Olivia. I went over there but he had to cancel. Next time, I promise,” was her disappointing reply.
“How about a little more fruit?” she teased, producing a banana.
I wasn’t going to get grouchy. She had surprised me with the cream last time and I liked it. “Let’s try chocolate this time for my sexy little kitten.”
She dipped the peeled banana and I opened up to take the hot chocolate sauce. While it tasted better than the cream, it also didn’t taste anything like what I wanted.
Shelly tried to make up for it with her words.
“Have you been thinking about cum?” she asked softly.
I moved my head in a small nod as the sauce dropped into my open mouth.
She seemed to understand and was pleased to know my answer. “I want to give it to you,” Shelly told me, “I want to feed you cum.”
Explicit and sexual. That girl knew how to get me going. “Here, take this,” she asked, bringing my hand to the banana.
As her hand untied the panty, Shelly noted, “You know, I do like these. They’re different, right?”
“I hoped you’d like them better.”
“And…” she began, then paused and her hand slid down the front of the untied garment, “I can get down here without taking them off…”
“Mmm,” I hummed.
Her fingers slowly probed for the exact spot. “Mmm, that’s it,” I told her.
“You just enjoy your dessert, Olivia,” she said in reply. Her fingers easily found home and went to work.
As her fingers started to rub, she asked me to, “Take it in your mouth,” in a way that suggested she was inspired in the moment and finding a new kink, “Yeah, let me see you suck it.”
Her hand was magic and I parted my lips to softly let the banana past.
She said my name, my girl name, a few more times. I slowly raised and lowered my head to let my lips ride up the banana as I held it steady. Mmm… mmm…
Either her fingers were particularly hot that night or something else was stoking the flames because I only lasted a few minutes before the quivering began.
Then it started to come over me. Trembling, I broke the banana in half as my orgasm took control of all motor functions. Shelly’s hand didn’t let up and I whined non-stop. “Come again!” she called out almost like it was a demand or an impatient request.
I let go of the fruit and grabbed hold of my bra and the heavy forms within it. I could hear Shelly’s breath as she rubbed me furiously. “Ahhh!” I called out as the second wave hit. Shelly slowed until I was done, then pulled out her hand.
“I love watching you get off, Olivia,” she told me, “Damn, it’s sexy.”
Her next words were, “Hey, you dripped chocolate sauce on my carpet, you know.”
“Sorry.”
She seemed overly upset. It’s not like it was my idea. Talking to herself, “I think I need to blot it first,” she said as she took the bowl and banana pieces to her kitchen.
That was my cue to get dressed and the first thought I had was that my panties were soaked and though I had thought about bringing a spare, I didn’t have a good way to carry them so didn’t.
“Sorry again about your carpet.”
“I think I can get it out.”
I was adjusting the pantyhose when she told me, “I’m headed out for a little break, then home for the holidays.”
She had told me that, like me, she could work from home sometime so I asked, “Thanksgiving? You’re going early?”
She worked on the stain which, really, looked like two or three little drops.
“Yeah, staying through Christmas and New Years. My folks need some help around the house.”
I pulled up the dress and found the sleeves. “That long?” I asked.
“Yeah, my dad fell and my brother’s a piece of shit.”
Dad fell… brother… I didn’t even know she had a brother. I looked at her in shock as if I didn’t know she had a dad either. “Wow, Shelly, that’s rough. Sorry.”
“There,” she announced, standing, “wasn’t so bad.” She was looking down, pleased to see we’d not left any permanent marks from our latest kinky encounter.
“Can you zip me?” I asked, turning away.
“It’s been wild few weeks, Jimmy. Let’s pick up where we left off, k?”
There was only one reply to that. “I can’t wait.”
She opened her door and her last words were, “And don’t cut that hair!”
And just like that, we were on a break.
Inspection Appointment
I sent a bunch of messages to Shelly, thanking her for having me over and apologizing about the stain she had to clean up. She didn’t answer any of them. It just wasn’t her style.
Faced with three months without sex, I let in some prudish self-doubt and questioned what I was doing. Dressing up like a girl to get off with someone who thinks I want to kiss guys was clearly beyond just the love of cum that I’d accepted. I let myself think I was doing something wrong and actually bagged up all the clothes and makeup.
But I didn’t do anything with the bags. The clothes, even the panties, were all carefully folded as if I knew I wasn’t going to follow through. My inner voice had made an empty threat that my body acted on with great theater that led to bags of women’s clothes that never even left my bedroom, let alone my apartment.
There might have been some doubt, some guilt, but I knew I couldn’t act on it and actually get rid of Olivia.
I found myself taking the hormones the next morning and said aloud, “Who are you kidding?”
So, instead of getting rid of my makeup, I added to it, carefully selecting shades and ordering them online. I got everything organized and dedicated one of my dresser drawers to the makeup I would put on every night once I was home and alone for weeks that followed.
Inspired and with too much free time, I painted my living room a pretty purple. Then I painted my bathroom pink and got pink bedding. The changes in my home décor fit my mood as I sauntered in a pretty teddy before bedtime.
As it turned out, I wouldn’t feel completely alone for the rest of that fall. At work one day, Ted came by while I was having lunch at my desk. “Jimmy, you mind if I ask you something?” he began.
To think of Ted as my friend was more evidence of the dearth of contact I had with human beings than the presence of a relationship with a co-worker. I pretty much talked to nobody else and barely talked to him. Ted and I went through orientation together. He was one of those good-looking popular guys so I was a little surprised when he decided not to ignore me like everyone else. Being nice to me surely made him look good but I didn’t mind. Sure, I thought, this guy can use me to advance his career.
I was routinely ridiculed and bullied by the cool guys in my apartment building and Ted being nice to me, even if it was just for show, was certainly preferable.
“I’ve been noticing,” he began, “you… your changes.”
He let his introductory words just float slowly around my cube before adding, with his hands up, “Now, if you don’t wanna talk about it, that’s fine you know.”
Partly because he had a disarming way about him and partly because I really didn’t care what anyone thought of me, I just asked, “The girl thing?”
He nodded and echoed with a little chuckle, “Yeah, the girl thing.”
“That obvious?” I asked.
“It was the… the…” he was gesturing at my chest.
Shocked, I covered my chest with one hand. “You can see them?!!!” I shrieked in a muffled panic.
He nodded guiltily but added, “Not a lot… or not much… but, you know.”
They were just little things. I didn’t think anyone could notice but me.
“You don’t have to tell me if…”
“Ted,” I said with a blushed face, “are you serious? You can see them?”
“Maybe I just noticed because I noticed the other stuff. You know, the pierced ears, your eyebrows, facial hair and, you know, just the way you’ve been acting. Are you, um…”
That relaxed me a little but “Do you think anyone else saw them?” I asked.
“You kinda just slip in and out of here, Jimmy. I don’t think anyone else even knows who you are.”
Feeling a little more at ease, I sighed and told him, “I guess I need to cover up better.”
“So, it’s not just me, then. There really is something going on?”
Ted would be the only guy I’d tell. “Yeah, it’s this girl I’ve been seeing,” I began.
In a hushed voice, I told Ted my semi-rehearsed story, omitting Shelly’s name in case he ever ran into her and adding, “She likes it when I dress up like a girl.” He didn’t need to know anything about my love for cum and certainly not that Shelly had trained me to climax like I had a pussy.
Ted was predictably cool about the whole thing. After all, this is the guy who went out of his way to talk to me when everyone else at orientation seemed to think I was a scrawny wimp.
“So, is she into… you know, your body changes?”
“Actually, she hasn’t seen them. I’ve only been topless around her once and it was weeks ago. They just sprouted recently and she won’t be back until after New Years.”
“Well, at this rate, she’ll be in for a surprise!” he joked.
Were my tits really growing that fast? I’d have to take some measurements or something.
As I thought about that, Ted asked, “So, if she’s gone, you’re just, what, waiting?”
It seemed my story about my sex life might have tipped off Ted that I wasn’t okay with the break that had been imposed on me. I sighed. “I don’t know. I mean, obviously I’m not going to see anyone else so I’ve been …” I hushed my voice even lower and confessed, “playing with makeup and dressing up like she liked.”
“Is that something you like, too?” he asked. His question didn’t seem to carry any judgment. Was this real interest or was he just putting on a show so he would be seen as the open-minded nice guy in the office?
I didn’t mind answering, anyway. “It’s at least passing the time!” I told him. “Actually,” I said, about to be more honest than I needed, “I want to leave the house again, like maybe buy some more clothes but I want to go out with makeup on.” I quickly added, “I’m sorry if that sounds too weird.”
He was nonchalant. “Whatever. I’ll bet you can’t wait until she gets back.”
“I really can’t.”
“So go do what makes you happy, Jimmy. It’s your life, right?”
I told him I worried that I didn’t look good enough. “My girlfriend said I was pretty but she also says I still look like a boy. I’d just be devastated to be out shopping and have everyone laugh at me!”
“Got any pictures?”
“Never thought of taking any and, I don’t know, maybe that’s a bad idea.”
With a nod, Ted then paused as if thinking while he looked at me. “I’m remembering,” he began, “when I was a kid, there were older girls in my neighborhood and I remember them coming home from college for the summers.” He seemed a bit wistful and went on, “I was a teenager, you know, all full of hormones and obsessed with pretty girls so I was sure to notice whenever they were outside. They had changed, see, during that time.” Appearing a little uncomfortable, he explained, “There’s something about women when they go through those last teen years and turn 20 or 21. Their faces get less round and, well, sexier. A few lost some weight and their hips and breasts fill out, you know, that hourglass shape.” Looking at me, he said, “But it’s the face changes that can be the most dramatic and, well, Jimmy, I really see that in you.”
“What?” I asked, “You say I’m changing like the girls you’re describing?”
He shrugged. “Well, you do look different than when I met you.”
Maybe the thought that I was becoming prettier (I sort of hoped that’s what Ted meant) made me more curious but that’s when I had my crazy idea. “Hey, I don’t live far from here. Do you think you might come by one night after work and see… I mean, look at me and tell me if I look alright?”
Faced with three months without sex, I let in some prudish self-doubt and questioned what I was doing. Dressing up like a girl to get off with someone who thinks I want to kiss guys was clearly beyond just the love of cum that I’d accepted. I let myself think I was doing something wrong and actually bagged up all the clothes and makeup.
But I didn’t do anything with the bags. The clothes, even the panties, were all carefully folded as if I knew I wasn’t going to follow through. My inner voice had made an empty threat that my body acted on with great theater that led to bags of women’s clothes that never even left my bedroom, let alone my apartment.
There might have been some doubt, some guilt, but I knew I couldn’t act on it and actually get rid of Olivia.
I found myself taking the hormones the next morning and said aloud, “Who are you kidding?”
So, instead of getting rid of my makeup, I added to it, carefully selecting shades and ordering them online. I got everything organized and dedicated one of my dresser drawers to the makeup I would put on every night once I was home and alone for weeks that followed.
Inspired and with too much free time, I painted my living room a pretty purple. Then I painted my bathroom pink and got pink bedding. The changes in my home décor fit my mood as I sauntered in a pretty teddy before bedtime.
As it turned out, I wouldn’t feel completely alone for the rest of that fall. At work one day, Ted came by while I was having lunch at my desk. “Jimmy, you mind if I ask you something?” he began.
To think of Ted as my friend was more evidence of the dearth of contact I had with human beings than the presence of a relationship with a co-worker. I pretty much talked to nobody else and barely talked to him. Ted and I went through orientation together. He was one of those good-looking popular guys so I was a little surprised when he decided not to ignore me like everyone else. Being nice to me surely made him look good but I didn’t mind. Sure, I thought, this guy can use me to advance his career.
I was routinely ridiculed and bullied by the cool guys in my apartment building and Ted being nice to me, even if it was just for show, was certainly preferable.
“I’ve been noticing,” he began, “you… your changes.”
He let his introductory words just float slowly around my cube before adding, with his hands up, “Now, if you don’t wanna talk about it, that’s fine you know.”
Partly because he had a disarming way about him and partly because I really didn’t care what anyone thought of me, I just asked, “The girl thing?”
He nodded and echoed with a little chuckle, “Yeah, the girl thing.”
“That obvious?” I asked.
“It was the… the…” he was gesturing at my chest.
Shocked, I covered my chest with one hand. “You can see them?!!!” I shrieked in a muffled panic.
He nodded guiltily but added, “Not a lot… or not much… but, you know.”
They were just little things. I didn’t think anyone could notice but me.
“You don’t have to tell me if…”
“Ted,” I said with a blushed face, “are you serious? You can see them?”
“Maybe I just noticed because I noticed the other stuff. You know, the pierced ears, your eyebrows, facial hair and, you know, just the way you’ve been acting. Are you, um…”
That relaxed me a little but “Do you think anyone else saw them?” I asked.
“You kinda just slip in and out of here, Jimmy. I don’t think anyone else even knows who you are.”
Feeling a little more at ease, I sighed and told him, “I guess I need to cover up better.”
“So, it’s not just me, then. There really is something going on?”
Ted would be the only guy I’d tell. “Yeah, it’s this girl I’ve been seeing,” I began.
In a hushed voice, I told Ted my semi-rehearsed story, omitting Shelly’s name in case he ever ran into her and adding, “She likes it when I dress up like a girl.” He didn’t need to know anything about my love for cum and certainly not that Shelly had trained me to climax like I had a pussy.
Ted was predictably cool about the whole thing. After all, this is the guy who went out of his way to talk to me when everyone else at orientation seemed to think I was a scrawny wimp.
“So, is she into… you know, your body changes?”
“Actually, she hasn’t seen them. I’ve only been topless around her once and it was weeks ago. They just sprouted recently and she won’t be back until after New Years.”
“Well, at this rate, she’ll be in for a surprise!” he joked.
Were my tits really growing that fast? I’d have to take some measurements or something.
As I thought about that, Ted asked, “So, if she’s gone, you’re just, what, waiting?”
It seemed my story about my sex life might have tipped off Ted that I wasn’t okay with the break that had been imposed on me. I sighed. “I don’t know. I mean, obviously I’m not going to see anyone else so I’ve been …” I hushed my voice even lower and confessed, “playing with makeup and dressing up like she liked.”
“Is that something you like, too?” he asked. His question didn’t seem to carry any judgment. Was this real interest or was he just putting on a show so he would be seen as the open-minded nice guy in the office?
I didn’t mind answering, anyway. “It’s at least passing the time!” I told him. “Actually,” I said, about to be more honest than I needed, “I want to leave the house again, like maybe buy some more clothes but I want to go out with makeup on.” I quickly added, “I’m sorry if that sounds too weird.”
He was nonchalant. “Whatever. I’ll bet you can’t wait until she gets back.”
“I really can’t.”
“So go do what makes you happy, Jimmy. It’s your life, right?”
I told him I worried that I didn’t look good enough. “My girlfriend said I was pretty but she also says I still look like a boy. I’d just be devastated to be out shopping and have everyone laugh at me!”
“Got any pictures?”
“Never thought of taking any and, I don’t know, maybe that’s a bad idea.”
With a nod, Ted then paused as if thinking while he looked at me. “I’m remembering,” he began, “when I was a kid, there were older girls in my neighborhood and I remember them coming home from college for the summers.” He seemed a bit wistful and went on, “I was a teenager, you know, all full of hormones and obsessed with pretty girls so I was sure to notice whenever they were outside. They had changed, see, during that time.” Appearing a little uncomfortable, he explained, “There’s something about women when they go through those last teen years and turn 20 or 21. Their faces get less round and, well, sexier. A few lost some weight and their hips and breasts fill out, you know, that hourglass shape.” Looking at me, he said, “But it’s the face changes that can be the most dramatic and, well, Jimmy, I really see that in you.”
“What?” I asked, “You say I’m changing like the girls you’re describing?”
He shrugged. “Well, you do look different than when I met you.”
Maybe the thought that I was becoming prettier (I sort of hoped that’s what Ted meant) made me more curious but that’s when I had my crazy idea. “Hey, I don’t live far from here. Do you think you might come by one night after work and see… I mean, look at me and tell me if I look alright?”
Tone!
As soon as I asked, I wanted to take it back and I tried. “Ted, I’m sorry, I’m not thinking.”
“No, no, no, it’s okay. I can do that. One night this week? Just say when.”
This was the same guy who helped Kristen move when her boyfriend dumped her, the same guy to go to Carlos’s citizenship ceremony. Some people suggested Ted was just being nice to climb the corporate ladder but others thought he was genuinely nice. I wasn’t sure but, either way, I guessed he could be trusted.
“Really?” I asked, the idea of shopping in high heels was lifting me up more than six inches.
“It’s not a big deal. Just say when,” he repeated.
“Um… tomorrow? Anytime after six?”
With a chuckle, Ted agreed and I suddenly couldn’t wait until the third person in my life would see me in heels!
What to wear, what to wear…
The wig, for sure. It would be my best disguise – no way I’d ever leave my place with my own hair. And a skirt, a snug one. Shelly liked that – or I think she did. Oh! She loved my soft sweater. I had another in dark pink that I had come to like even better. It would be a chance to wear the adorable brown booties. I was thrilled!
“I’m catching up with some friends after work,” Ted told me, “How’s around eight or so?”
He wondered why that made me laugh, as if there was a set time to come over and see me dressed as a woman. I wouldn’t tell Shelly but she wouldn’t think it was funny anyway.
I was more nervous than I should have been and ready an hour early. I did my customary look down the hallway when I opened the door. “Come in, come in!” I said, for some reason more nervous than when my girlfriend had visited me.
“Well, you’ve grown!” Ted quipped.
My hands went to my breasts then I chuckled, “No, they’re silicone,” then I added, “Oh, you know that. Sorry, I’m a little nervous.”
I shook my hands and apologized. “You’re the only other person to see me.” He didn’t need to know about Don.
“I’d be nervous, too. It’s alright.”
I took a deep breath and let it out. “Well, tell me. Be honest. Can I go to the mall like this?”
As Ted walked around me, the butterflies passed. I put my hands on my hips, awaiting the compliment. Would he simply say “sexy”? I also hoped to hear “pretty”.
“Well, what do you think?” I asked.
“I don’t know, Jimmy,” was the start of his reply.
I was crestfallen.
“Sexy, sure,” he began, “but, really, it’s all a little too much.”
“Too much?” I never heard that. Shelly never said anything like that.
“Yeah, a little. The huge boobs and, I’m sorry, but even I can tell that’s a wig.”
“That’s just because you know me.”
I crossed the line and was defensive. “I’m sorry. Really? You can tell?”
“Sorry, Jimmy.”
I needed to let it sink in but I needed to learn more. Like, were the shoes okay? Too much jewelry?
“I’m such a bad host. Can I get you a drink?”
“Had two but some water would be nice.”
I turned toward my kitchen. “Sorry to get defensive. It’s just that my girlfriend always said I looked nice.”
“I’m sure you’re perfect for her. I just don’t want you to draw a lot of attention out shopping,” he said, then added, “I mean, I guess that you don’t.”
“That’s exactly what I don’t want, either,” I told him.
He smiled at me as I returned with his water. “That must be some girlfriend you have.”
“She’s into me and I really like that.”
He smiled and I asked, “What about you, you got a girlfriend?”
“Nah, not since summer. Had a real bad ending so I’m taking some time off.”
He had been so nice to come over. I felt I needed to talk a little before interrogating him about my looks. “Bad?” I asked as I showed off my ability to sit down in a tight skirt.
He ran his hand through his hair. “Pretty crazy, yeah. She just kinda blew up on me and decided I was the worst person in the world. She got real angry and tried to have sex with, oh, let’s see… my boss, my brother, some friends... chick really got nutty.”
“Wow, that’s crazy. Good for them, though, right, for shutting her down.”
“I guess I wouldn’t have really cared,” he told me, “I might feel bad for them and want to warn them but, really I was soooooo over that chick. She did end up hooking up with my ex-boss and, if you can believe it, my ex-girlfriend’s prior boyfriend. As if that was supposed to bother me or something.”
“People can get crazy,” I summed up, ready to get back to my questions, “So, are the shoes okay?”
“No, no, no, it’s okay. I can do that. One night this week? Just say when.”
This was the same guy who helped Kristen move when her boyfriend dumped her, the same guy to go to Carlos’s citizenship ceremony. Some people suggested Ted was just being nice to climb the corporate ladder but others thought he was genuinely nice. I wasn’t sure but, either way, I guessed he could be trusted.
“Really?” I asked, the idea of shopping in high heels was lifting me up more than six inches.
“It’s not a big deal. Just say when,” he repeated.
“Um… tomorrow? Anytime after six?”
With a chuckle, Ted agreed and I suddenly couldn’t wait until the third person in my life would see me in heels!
What to wear, what to wear…
The wig, for sure. It would be my best disguise – no way I’d ever leave my place with my own hair. And a skirt, a snug one. Shelly liked that – or I think she did. Oh! She loved my soft sweater. I had another in dark pink that I had come to like even better. It would be a chance to wear the adorable brown booties. I was thrilled!
“I’m catching up with some friends after work,” Ted told me, “How’s around eight or so?”
He wondered why that made me laugh, as if there was a set time to come over and see me dressed as a woman. I wouldn’t tell Shelly but she wouldn’t think it was funny anyway.
I was more nervous than I should have been and ready an hour early. I did my customary look down the hallway when I opened the door. “Come in, come in!” I said, for some reason more nervous than when my girlfriend had visited me.
“Well, you’ve grown!” Ted quipped.
My hands went to my breasts then I chuckled, “No, they’re silicone,” then I added, “Oh, you know that. Sorry, I’m a little nervous.”
I shook my hands and apologized. “You’re the only other person to see me.” He didn’t need to know about Don.
“I’d be nervous, too. It’s alright.”
I took a deep breath and let it out. “Well, tell me. Be honest. Can I go to the mall like this?”
As Ted walked around me, the butterflies passed. I put my hands on my hips, awaiting the compliment. Would he simply say “sexy”? I also hoped to hear “pretty”.
“Well, what do you think?” I asked.
“I don’t know, Jimmy,” was the start of his reply.
I was crestfallen.
“Sexy, sure,” he began, “but, really, it’s all a little too much.”
“Too much?” I never heard that. Shelly never said anything like that.
“Yeah, a little. The huge boobs and, I’m sorry, but even I can tell that’s a wig.”
“That’s just because you know me.”
I crossed the line and was defensive. “I’m sorry. Really? You can tell?”
“Sorry, Jimmy.”
I needed to let it sink in but I needed to learn more. Like, were the shoes okay? Too much jewelry?
“I’m such a bad host. Can I get you a drink?”
“Had two but some water would be nice.”
I turned toward my kitchen. “Sorry to get defensive. It’s just that my girlfriend always said I looked nice.”
“I’m sure you’re perfect for her. I just don’t want you to draw a lot of attention out shopping,” he said, then added, “I mean, I guess that you don’t.”
“That’s exactly what I don’t want, either,” I told him.
He smiled at me as I returned with his water. “That must be some girlfriend you have.”
“She’s into me and I really like that.”
He smiled and I asked, “What about you, you got a girlfriend?”
“Nah, not since summer. Had a real bad ending so I’m taking some time off.”
He had been so nice to come over. I felt I needed to talk a little before interrogating him about my looks. “Bad?” I asked as I showed off my ability to sit down in a tight skirt.
He ran his hand through his hair. “Pretty crazy, yeah. She just kinda blew up on me and decided I was the worst person in the world. She got real angry and tried to have sex with, oh, let’s see… my boss, my brother, some friends... chick really got nutty.”
“Wow, that’s crazy. Good for them, though, right, for shutting her down.”
“I guess I wouldn’t have really cared,” he told me, “I might feel bad for them and want to warn them but, really I was soooooo over that chick. She did end up hooking up with my ex-boss and, if you can believe it, my ex-girlfriend’s prior boyfriend. As if that was supposed to bother me or something.”
“People can get crazy,” I summed up, ready to get back to my questions, “So, are the shoes okay?”
Toned!
Ted offered more opinions I didn’t want to hear and left me more crestfallen than I would admit. He actually apologized for his opinions before saying goodnight.That left me back to feeling idle. I hadn’t realized it but the idea of going out shopping as a woman had taken my mind off of sex for days. With hopes dashed, I put on makeup the following night and just looked into the mirror with anxiety. How would I get through two more months?
I turned to my bed at first. After that first night, I hadn’t enjoyed my body in bed because I didn’t want to spoil the effect that Shelly’s magical hand had on me. Sure, masturbating that night felt great – all three times – but that’s not what a really wanted, it’s not who I wanted to be. What I wanted to be was Olivia, the sexy girl who swallowed cum.
But, since I couldn’t be her, I put on my animal print teddy that night and let my fingers run wild, climaxing quickly. I changed the towel and then went again before drifting off to sleep. For the next week, I was getting myself off every night. I’d think about my times with Shelly and the taste of Don’s cum as I rubbed away.
It was about a week later when I learned I was just a little more special than Shelly knew.
I was wearing my pink teddy, the one with snaps on the bottom, along with my first pair of heels as I moved around the house before washing off my makeup.
Inside the bustier were the breast forms and I wore the wig, too. People might think it looked fake but I loved the feel of the long hair as it teased my bare back and shoulders. I walked past my mirror and back again over and over, getting myself in the mood for another evening of bedtime distraction.
“Mmm,” I hummed aloud as paused by front door. I let my hands glide down the pink lace and around my hips. Then I brought my right hand up and tucked it beneath the teddy to the spot I’d gotten re-lasered days before. “Mmm.”
I let my fingers go to work, easily finding the right place and their productive tempo. “So good,” I quietly sighed.
The rolling of my fingers went on. If I had a plan, it was just to get myself aroused before bed but my fingers had something else in mind.
My whining began and then… then… “Ahh!” came the familiar sound of joy that joined the erotic bliss of sexual climax.
I was coming. Standing in my living room, wearing high heels, I soaked my carpet just between them.
It was nearly Thanksgiving before I came up for air. In the weeks that had followed that first time, I’d gotten off standing in every teddy I owned. I had rubbed myself to climax wearing every pair of panties I’d bought and, eventually, I came while wearing every outfit as I slid a hand down the front of skirts and pants and up the hemline of dresses.
I didn’t want to bother her but I had to share my discovery with Shelly. “Happy Thanksgiving!” I wrote, “Write back! I want to tell you something!”
Shelly was going to love my news, I just knew it.
When her reply came, it was predictable. “Same to you. Real busy here. See you soon.”
That was it. Shelly had a boyfriend who could rub his imaginary pussy to climax while wearing women’s lingerie and standing in high heels but she was too busy to find out.
It was her lack of interest that put me on the path to tone down my look so I could go out. I just couldn’t imagine staying in and rubbing myself all the time. I was sure the magic would leave me.
I had a pair of black pants that were fitting fairly well by then without the pads and with a padded bra that I ordered online, I guessed my little tits would be presentable and certainly not “too much”.
Still worried about being noticed, I went back to dying my hair black on the Friday night before I’d leave the house in heels.
Out shopping in a simple black camisole and a pretty purple cardigan was supposed to be just a way to make an errand more fun. I wanted more clothes and felt there were gaps in my makeup collection and the cute outfit was just a needed feature so that I could try things on and linger around the cosmetics section without drawing curious looks.
Sure, I’d made a few dashes to and from my car but my destination was always a safe place with just one or two people who knew Oliva wasn’t my real name. That day, though, was entirely different as I walked toward the mall’s entrance. Feeling my hair as if I needed to be sure it didn’t get left in the car, I strode in without hesitation, confident my toned-down look was just perfect for a boy named Jimmy to shop for women’s clothes.
In addition to the shoes, the sweaters, and the eye shadow, I ended that day with a carful of confidence and a discovery that being Olivia could be about more than sex. No, modelling tight jeans in a women’s dressing room would never be as thrilling or as wonderful as satisfying my need for cum but being Olivia could make ordinary errands something to look forward to.
Olivia would make a few more outings and took over my existence when I was at home. Calling out my love for cum as I rubbed my make-believe pussy had freed me from any second thoughts or buried shame about my desire. When it came to sex, I only wanted to be Olivia and she only wanted one thing.
Shelly would return just after the holidays as a brunette. My changes would be much more shocking when my girlfriend would see me for the first time after months of my best efforts at feminizing my body.
Back To Heaven
“Wear that slutty outfit you had on when you came to my place – the leather skirt and tight sweater,” Shelly told me, “And the wig’s fine. Don’s cool with it.”
She had been home for weeks but couldn’t find time to meet up. “Just crazy at work after being away,” she explained. I still hadn’t had a chance to tell her about my new skill and was giddy with the idea of surprising her but I just couldn’t get on her schedule!
So, when she surprised me with a message, “Wanna go see Don tomorrow?” I leapt at the chance.
Shelly would pick me up Saturday. Back then, it still caught me off-guard when she’d start our dates at odd times like that one at three in the afternoon. I hadn’t yet understood that blowjob visits weren’t like normal dates that would often be in the late afternoon or early evening.
Dressed and ready when she tapped, I grabbed my jacket and quickly opened the door, eager to sneak out and begin our adventure. “Hey,” Shelly began slowly. She had presented herself in what I began to see was he pick-up clothes. There we were, on our way to go to another man’s house and there she was, in platform heels tight pants. I wondered if Don knew he wasn’t getting the real Shelly. I doubt he would have cared.
She didn’t seem to want to come in but didn’t seem to be leaving, either. “Let’s get going!” I urged quietly. My neighbors hadn’t yet seen me and I wanted to keep it that way. I closed the door and took her arm.
“New coat?” she asked.
“I’d look out of place without something,” I answered, still whispering, “got it second-hand.”
Shelly looked at the red fox and seemed to approve. “Nice.” Her approval warmed me but I was still scanning left and right as we headed toward her car.
As she opened her door, she asked, “Why so worried, anyway? I mean, they’re just people. Who the fuck cares what they think?”
“It’s just these guys Enrique and Paul,” I told her as I smoothed my skirt, “They’re, like, the cool guys in the complex – always having a beer on their balcony. People stop by and hang out or, used to before it got cold. Now they have parties or play video games or something. I can always hear them from the hall.”
“Friends of yours?”
“Me?” I answered, feeling shock, “No, they’re kinda jerks, actually. They made fun of me when I couldn’t carry in my grocery bags last summer and got some of the girls laughing at the way I had to make so many trips just because I’m not some huge beefcake kind of idiot. They pick on anybody who’s not a big weightlifter or something.”
I guessed Shelly didn’t want to make me relive the embarrassment or maybe she wanted to get me in right mood so she moved on.
“So, you ready for this?”
“God, you have no idea! Shelly, it seems like it’s been so long!”
That devilish smile reminded me how much I missed our sex life together. Shelly was looking at me, examining me.
“I look alright, don’t I? This is what you told me to wear.”
“You look fine, Jimmy,” she said as she watched the road. Another look in my direction and she asked, “You get bigger tits?”
I blushed. “Actually, they’re the same things but… I’ve been taking some pills and I sorta grew some?”
“Grew some? Like you got tits of your own?”
I was quick to correct her, “They’re not much, just little things but I guess they’re noticeable enough when they’re under the silicon forms.”
We were out of her car and walking to Don’s as she assured me again, “No, don’t worry at all. Don’s into big tits and he’ll love the way you look.” She added, “You’ve become quite the little hottie, you know.” After a few steps, she added, “I mean, for a guy trying to look like a girl, that is.”
“Look,” she began as she stopped walking for a moment, “I know you’re into the stuff we do and I think it’s great that you’re cool with getting this guy involved. Afterwards, I promise, we’ll go back to just you and I like you like it.”
I was on a carnival ride and had no control. “Sure,” I said, not really knowing what she meant or what I wanted.
“You think he’ll like the way I look?” I asked as we approached Don’s house.
“He’s going to love you.”
It felt more like an appraisal than flattery and it warmed me. “I hope so!” I said with a little shriek since I couldn’t hide my excitement.
Shelly pressed the doorbell in a nonchalant way as if this wasn’t a vitally important moment for me after months of waiting. I had masturbated, I don’t know, dozens of times to the memory of this man’s cum in my mouth and I was about to finally get it again.
Shelly just turned and smiled. She quipped, “Really big tits, let’s see if he notices.”
“Shelly!”
Don answered the door to find us giggling which he seemed to like. His eyes went to mine as he spoke to my girlfriend, “I see you brought your friend again, O… Olympia?”
“Olivia,” I said, softly correcting him as we entered.
“You look great today,” Don said, “Can I take your coats,” adding with emphasis, “girls?”
Shelly was ready for Act I as Don stared at my bosom. Yeah, he noticed the extra cup size. I smiled nervously. He and Shelly kissed but Don stopped to look at me again and said, “Olivia, I don’t think I appreciated those beautiful lips of yours before. Come here.”
The compliment was nice but… come here? Go there?
Shelly simply said, “Don’s our host, Olivia, come on.”
I stood there. What was Don up to?
Shelly snarled. Her words said, “Come on,” but her expression said, “Don’t fuck this up!”
I stepped over and Don immediately put his hand on the small of my back. “You’re lovely in that sweater,” he told me.
Going along, Shelly added, “She loves soft things.”
It wasn’t untrue, though I hadn’t told her that.
Don was looking at my mouth, making me self-conscious that I’d misapplied my lipstick.
“Such lovely lips,” he said, stretching out each syllable. Sex seemed to ooze out along with his words. “Do you two kiss?”
“Uh-huh,” I answered. It was a quick response as if I was suddenly under his spell. All I could think about was Shelly giving me a mouthful of that man’s cum.
“Kiss,” he said or, rather suggested. If it was a command, it didn’t sound like one.
I turned to Shelly who seemed just a little put off. All this was obviously a surprise to her, too. Still, she didn’t hesitate and we kissed with my wrists weightlessly hanging over her shoulders as she held my waist.
“Nice,” declared our host. He took hold of me again and asked, “You’re here for something special, aren’t you?” This was not how our afternoon was supposed to go.
“I am.” Yes, I was under his spell or the spell of my addiction, it didn’t matter which.
Our host teased me, asking what I wanted.
“Your cum,” I answered. When I did, I didn’t really look at him. I was looking in his direction but didn’t make eye contact. I didn’t see Don, per se. Don, the person, wasn’t a person at all to me. I knew nothing about him and didn’t care about him and though I badly wanted a man’s cum, I didn’t want the man.
It was a confusing time but that’s how I felt. When asked again, I repeated my answer in the same way and found myself getting a little light-headed with arousal.
“Are these the lips,” Don teased while tracing my lower lip with a finger, “that will have my cum on them?”
“Please?” I whined.
“Well then,” he began as if having just finished some kind of calculation in his head, “I think I’ll need to kiss them first.”
Hazy with desire but still aware enough to understand that a man wanted to kiss me, I turned to Shelly for relief.
That girl would never let a good thing get interrupted. “Kiss him, Olivia,” was all she said.
And that’s how I came to kiss my first man. Don was an older guy who I’d never get to know. The little I would learn was that he was the right guy at the right time and took advantage of Shelly’s overtures and her kinky needs. But aside from whatever made Don unremarkable, in that moment I’d discover one thing that mattered: Don was a man.
Our kiss lingered on for precious moments. Touching Don’s lips, I expected to simply satisfy the host’s request, to check off a box on my way to getting what I needed.
Instead, I discovered that a man’s kiss is nothing like a woman’s and, more importantly much, much more importantly, I was finally finding out how wonderful kissing could be.
“Alright you two,” I heard Shelly say as her hand pulled my arm from Don’s shoulder. She would later say she was saving me but I guessed she was jealous. I licked my lips and let myself register the first time I kissed a man.
Shelly stepped in and Don asked, “Let me see those tits of yours,” in a way that suggested this wasn’t going to be the first time. Shelly obliged him and seemed more at ease now that she was the center of attention once more.
I looked on as Don groped her body and they made out for a few moments before Shelly’s hand found our host was ready for Act II.
She had been home for weeks but couldn’t find time to meet up. “Just crazy at work after being away,” she explained. I still hadn’t had a chance to tell her about my new skill and was giddy with the idea of surprising her but I just couldn’t get on her schedule!
So, when she surprised me with a message, “Wanna go see Don tomorrow?” I leapt at the chance.
Shelly would pick me up Saturday. Back then, it still caught me off-guard when she’d start our dates at odd times like that one at three in the afternoon. I hadn’t yet understood that blowjob visits weren’t like normal dates that would often be in the late afternoon or early evening.
Dressed and ready when she tapped, I grabbed my jacket and quickly opened the door, eager to sneak out and begin our adventure. “Hey,” Shelly began slowly. She had presented herself in what I began to see was he pick-up clothes. There we were, on our way to go to another man’s house and there she was, in platform heels tight pants. I wondered if Don knew he wasn’t getting the real Shelly. I doubt he would have cared.
She didn’t seem to want to come in but didn’t seem to be leaving, either. “Let’s get going!” I urged quietly. My neighbors hadn’t yet seen me and I wanted to keep it that way. I closed the door and took her arm.
“New coat?” she asked.
“I’d look out of place without something,” I answered, still whispering, “got it second-hand.”
Shelly looked at the red fox and seemed to approve. “Nice.” Her approval warmed me but I was still scanning left and right as we headed toward her car.
As she opened her door, she asked, “Why so worried, anyway? I mean, they’re just people. Who the fuck cares what they think?”
“It’s just these guys Enrique and Paul,” I told her as I smoothed my skirt, “They’re, like, the cool guys in the complex – always having a beer on their balcony. People stop by and hang out or, used to before it got cold. Now they have parties or play video games or something. I can always hear them from the hall.”
“Friends of yours?”
“Me?” I answered, feeling shock, “No, they’re kinda jerks, actually. They made fun of me when I couldn’t carry in my grocery bags last summer and got some of the girls laughing at the way I had to make so many trips just because I’m not some huge beefcake kind of idiot. They pick on anybody who’s not a big weightlifter or something.”
I guessed Shelly didn’t want to make me relive the embarrassment or maybe she wanted to get me in right mood so she moved on.
“So, you ready for this?”
“God, you have no idea! Shelly, it seems like it’s been so long!”
That devilish smile reminded me how much I missed our sex life together. Shelly was looking at me, examining me.
“I look alright, don’t I? This is what you told me to wear.”
“You look fine, Jimmy,” she said as she watched the road. Another look in my direction and she asked, “You get bigger tits?”
I blushed. “Actually, they’re the same things but… I’ve been taking some pills and I sorta grew some?”
“Grew some? Like you got tits of your own?”
I was quick to correct her, “They’re not much, just little things but I guess they’re noticeable enough when they’re under the silicon forms.”
We were out of her car and walking to Don’s as she assured me again, “No, don’t worry at all. Don’s into big tits and he’ll love the way you look.” She added, “You’ve become quite the little hottie, you know.” After a few steps, she added, “I mean, for a guy trying to look like a girl, that is.”
“Look,” she began as she stopped walking for a moment, “I know you’re into the stuff we do and I think it’s great that you’re cool with getting this guy involved. Afterwards, I promise, we’ll go back to just you and I like you like it.”
I was on a carnival ride and had no control. “Sure,” I said, not really knowing what she meant or what I wanted.
“You think he’ll like the way I look?” I asked as we approached Don’s house.
“He’s going to love you.”
It felt more like an appraisal than flattery and it warmed me. “I hope so!” I said with a little shriek since I couldn’t hide my excitement.
Shelly pressed the doorbell in a nonchalant way as if this wasn’t a vitally important moment for me after months of waiting. I had masturbated, I don’t know, dozens of times to the memory of this man’s cum in my mouth and I was about to finally get it again.
Shelly just turned and smiled. She quipped, “Really big tits, let’s see if he notices.”
“Shelly!”
Don answered the door to find us giggling which he seemed to like. His eyes went to mine as he spoke to my girlfriend, “I see you brought your friend again, O… Olympia?”
“Olivia,” I said, softly correcting him as we entered.
“You look great today,” Don said, “Can I take your coats,” adding with emphasis, “girls?”
Shelly was ready for Act I as Don stared at my bosom. Yeah, he noticed the extra cup size. I smiled nervously. He and Shelly kissed but Don stopped to look at me again and said, “Olivia, I don’t think I appreciated those beautiful lips of yours before. Come here.”
The compliment was nice but… come here? Go there?
Shelly simply said, “Don’s our host, Olivia, come on.”
I stood there. What was Don up to?
Shelly snarled. Her words said, “Come on,” but her expression said, “Don’t fuck this up!”
I stepped over and Don immediately put his hand on the small of my back. “You’re lovely in that sweater,” he told me.
Going along, Shelly added, “She loves soft things.”
It wasn’t untrue, though I hadn’t told her that.
Don was looking at my mouth, making me self-conscious that I’d misapplied my lipstick.
“Such lovely lips,” he said, stretching out each syllable. Sex seemed to ooze out along with his words. “Do you two kiss?”
“Uh-huh,” I answered. It was a quick response as if I was suddenly under his spell. All I could think about was Shelly giving me a mouthful of that man’s cum.
“Kiss,” he said or, rather suggested. If it was a command, it didn’t sound like one.
I turned to Shelly who seemed just a little put off. All this was obviously a surprise to her, too. Still, she didn’t hesitate and we kissed with my wrists weightlessly hanging over her shoulders as she held my waist.
“Nice,” declared our host. He took hold of me again and asked, “You’re here for something special, aren’t you?” This was not how our afternoon was supposed to go.
“I am.” Yes, I was under his spell or the spell of my addiction, it didn’t matter which.
Our host teased me, asking what I wanted.
“Your cum,” I answered. When I did, I didn’t really look at him. I was looking in his direction but didn’t make eye contact. I didn’t see Don, per se. Don, the person, wasn’t a person at all to me. I knew nothing about him and didn’t care about him and though I badly wanted a man’s cum, I didn’t want the man.
It was a confusing time but that’s how I felt. When asked again, I repeated my answer in the same way and found myself getting a little light-headed with arousal.
“Are these the lips,” Don teased while tracing my lower lip with a finger, “that will have my cum on them?”
“Please?” I whined.
“Well then,” he began as if having just finished some kind of calculation in his head, “I think I’ll need to kiss them first.”
Hazy with desire but still aware enough to understand that a man wanted to kiss me, I turned to Shelly for relief.
That girl would never let a good thing get interrupted. “Kiss him, Olivia,” was all she said.
And that’s how I came to kiss my first man. Don was an older guy who I’d never get to know. The little I would learn was that he was the right guy at the right time and took advantage of Shelly’s overtures and her kinky needs. But aside from whatever made Don unremarkable, in that moment I’d discover one thing that mattered: Don was a man.
Our kiss lingered on for precious moments. Touching Don’s lips, I expected to simply satisfy the host’s request, to check off a box on my way to getting what I needed.
Instead, I discovered that a man’s kiss is nothing like a woman’s and, more importantly much, much more importantly, I was finally finding out how wonderful kissing could be.
“Alright you two,” I heard Shelly say as her hand pulled my arm from Don’s shoulder. She would later say she was saving me but I guessed she was jealous. I licked my lips and let myself register the first time I kissed a man.
Shelly stepped in and Don asked, “Let me see those tits of yours,” in a way that suggested this wasn’t going to be the first time. Shelly obliged him and seemed more at ease now that she was the center of attention once more.
I looked on as Don groped her body and they made out for a few moments before Shelly’s hand found our host was ready for Act II.
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