Mike & I

I was your typical college student in most aspects; I was eighteen, away from home for the first time and looking for sex and parties. The one thing that made me a little different, was the fact that I was a cross-dresser, closeted but dressing whenever possible. I was at college on a swimming scholarship, it was a full ride deal, full tuition and living expenses, unfortunately this meant living in a dorm room with a roommate. This made it difficult for me to dress as often as I would have liked but I learned to live with it.

My roommate was Mike, a star full back on the college team, only in his second year; every NFL team had already scouted Mike. Mike was built like a brick shithouse, six foot six, two hundred eighty pounds of solid muscle. Mike was from a very rich family and had turned down several scholarships from the top schools in the country. Mike’s father had gone to school here before making his millions and wanted his pride and joy to follow in his footsteps. Mike received a large living allowance from his family but was told he must live on campus, it built character his father said.

Mike and I became best friends and somewhat of a joke in the dorm, "David and Goliath" they called us, Mike being as big as he was and me being five foot four and one hundred twenty six pounds made for quite a contrasting pair when walking down the halls. Mike kept the other guys from giving me a hard time and in return I helped Mike with all his classes, he was a great football player but a lousy student. Besides our size difference, other things stood out between us. Mike could have any girl he wanted and I had a hard time getting a girl to talk to me, they wanted a masculine looking man for a boyfriend, not a small wimp with a small face and long hair who was said to be as "pretty as most cheerleaders". While the crossdresser in me loved the compliment, it did make it hard to get a date. Despite the many offers, Mike seldomly dated, preferring to spend his time either at the gym or in the dorm with me. Mike never went to a movie or club without inviting me along, I was his constant companion, he spent more money on me than any thing else.

I would on occasion borrow money off Mike and get a hotel room for the weekend, telling him I needed time to study or prepare for a meet, Mike never asked any questions and refused my attempts to pay him back when I got my monthly living allowance. I would head straight to the storage locker I kept and get all my feminine trappings, makeup, curling irons, dresses and other items I needed to become a hot looking chick. I would check in, put out the do not disturb sign and spend the entire weekend indulging in my secret fantasies, reverting back to my male persona only long enough to go and eat. Once I went to a nearby city and even went shopping en-femme, this was the most nerve racking yet enjoyable weekend of "Tanya’s" life. I found I needed to get dressed more and more often to be happy and it was not long before Mike began to wonder about my weekend getaways, while he never asked, he did begin to hesitate when I asked for the loans. I knew I would have to cut down on my trips but found it harder to subdue the urges, I thought of purging but new it would take me months or longer to rebuild my collection if I did, this seemed like a good excuse so I stuck to it.

One long weekend, I again borrowed money from Mike, saying I had to get away to study for upcoming exams, wrong excuse to use, most of the dorm was empty as usual on long weekends. Mike gave me the money and away I went what I did not know was that Mike had decided to follow me to see what I was really doing. Unknowingly, I picked up my things and checked into the hotel and immediately started my transformation into Tanya. Mike went to the front desk of the hotel and told them I had forgotten my textbooks and asked for my room number and a spare key, saying he did not want to disturb my studies by knocking on the door. After getting the info and key, Mike came to my room and let himself in. I thought I would die when I walked out of the bathroom after curling my long blond hair to see Mike standing there. Mike did get a word out before I began to sputter out a weak explanation; I should have kept my mouth shut. After I spoke a look of recognition and shock came over Mike’s face, I thought you had a girlfriend in here, he said, I would never have guessed it was you. My lack of confidence in my looks had given me away. Mike asked all the usual questions, did I want to be a girl, how long, why and of course was I gay. I answered his questions, no; I did not want a sex change operation, since I was about six and because it felt good to me. It was my turn to be shocked when I told Mike I was not gay; his response was oh, that is really too bad. I was stunned by the response but did not let on, I merely asked why that disappointed him, and did he need a new lover. Again I was floored when he said I don’t have a lover right now, but would have loved to have one who looked like I did, someone he could take out in public without coming out of the closet about his sexuality.

We spent most of the night talking about our lives and sipping on drinks. I pulled out a joint and Mike agreed to smoke with me since it was the off season and would not have to take any drug tests. We smoked a few joints and drank a couple bottles of wine I had with me and before I knew it, Mike was sitting on the bed next to me, his hand resting on my small nylon clad knee. I don’t know if it was the dope and wine or what but I made no attempt to move his hand. Mike took this as a sign of consent and slowly moved his hand further up my leg until he reached the top of my stocking and felt my smooth skin. Next thing I knew, Mike had an arm around me and was gently pulling me closer to him until we were face to face. I did not resist when Mike leaned towards me and gave me a soft kiss on the lips, before long I had my arms around his neck and we were making out like a couple of high school kids. The feeling of having Mike’s big strong arms wrapped about me just felt right, I felt safe. Mikes tongue pressed between my lips, which I parted to give him easier access, he wrapped his tongue around mine and I melted, I was his. I realized what I was doing, kissing a man, but the feel of his strong lips pressing against my soft ruby red painted lips was to enticing and I did not want it to end. Being a gentleman, Mike pulled away before it went any further, much to my disappointment, and we spent the rest of the night trying to figure out where this was going to take us. I changed into a long slinky black silk nightgown and we fell asleep in each other’s arms.

I awoke the next morning to a knock on the door, Mike had ordered us breakfast, something I had never done before due to the cost, and Mike served me breakfast in bed, coffee, toast and a vegetarian omelet. We lounged in the room until around two when Mike looked at me and said get your best outfit on, we are going on a little trip this afternoon, I asked where we were going and all he said was you will see. I showered and dried and curled my hair, did my makeup and started to decide what to wear. I decided on a pair of black tanga panties, red garter belt, black seamed stockings and a black bra. I choose a black spandex skirt, which fell to just above the knees and a red blouse with sheer sleeves. A pair of large hoop earrings, a black choker, a gold bracelet, three-inch spike heels and a clutch purse completed the look. I touched up my nail polish and declared myself presentable. We took the elevator to the lobby and headed out the front door, I got several looks from the men in the lobby, and they were looks of desire, not recognition, as I had feared. We hopped in Mike’s "vette" and were soon on the highway. I again asked where we were going and Mike said to light a joint and he would fill me in. I lit a fat joint and Mike started, while you were sleeping this morning, I looked through your closet. You had a great selection of sexy clothes and outfits for going to the clubs, I noticed you had nothing that you could wear out for a dressy evening, or to a formal event. His next statement made me choke on the toke I had just taken, besides he said, you need to look a little more demure if you are going to meet my parents. I said stop right there, I never said anything about meeting your parents. All Mike said was we will talk about it over supper tonight, for now lets go shopping.

We pulled into a large mall in a nearby city, just across the state line, before we went in, Mike made me promise not to argue with anything he said or did, if I did not promise, we were getting back in the car and heading home. I promised and away we went, Mike said we had to start at the bottom and work from there, so we headed first into a lingerie store. Soon I walked out with several new bras, panties, corsets and other more intimate items that Mike choose for me. Mike started to head fore a shoe store, but I stopped him, stating that you chose the shoes to go with the outfits, not the other way around. We hit several shops and boutiques, that afternoon I modeled more clothes then I had ever imagined. Soon we walked back to the car to store the fifteen bags of clothes I now owned; I had skirts, dresses, and blouses, skirt suits and even evening gowns. Next stop was the shoe store, where I ended up getting twenty pairs of shoes and boots, pumps, heels ranging from one inch all the way to five inch and four pairs of top quality leather boots, including a pair of thigh highs with four inch spiked heels. Mike wanted to keep going but I begged off, my feet were killing me, I was not used to all this walking in heels. We went and put the rest of the items in the car and then headed for a drink before supper. 

In the lounge we stopped at, I could feel the eyes of every guy in the place checking me out, Mike played it up by giving me a long deep kiss before squeezing my ass as I sat. After the first drink, I excused myself to go to the ladies room, another new experience for me, I did my business and touched up my makeup while chatting with a very attractive young waitress who came in just after me. We talked about the weather and other small talk before she asked me if I was new to the area, I said we were just visiting, explaining the spur of the moment shopping trip. Lisa said she was jealous and then commented that I made a very beautiful looking girl, I stuttered and she said relax, I won’t tell anybody. I asked how she knew and she merely said that women could tell these things, besides she said, very few real women have Adams apples. She removed the inch wide choker from her own neck and then asked if I would like to trade, mine was a half inch wide and did not hide my Adams apple very well. I thanked her and returned to my table. We had one more drink and got ready to leave, Lisa brought us our bill and slipped me a note with her address and invited the two of us over to her place for drinks later that night. I smiled after reading the noted and made Mike leave her a very large tip, he asked why and I said I will explain in the car, just leave a very large tip. Mike just shrugged his shoulders and threw a hundred-dollar bill on the table to pay the twelve-dollar tab, after ensuring that Lisa got the tip, we left for supper.

Mike informed me that while I was in the bathroom, he had called and made reservations at a very exclusive restaurant, the kind that require suit and tie for the men and gowns for the ladies. With this in mind, Mike rented us another hotel room and informed me I had about two hours to get ready, then he left to go get a suit for the evening. I ran a hot tub and shaved my legs; chest, pits and even trimmed my pubic hair. After getting out of the tub, I saw a box sitting on the bed that I knew we had not bought that day, I read the note on top and it said "I thought you could use a few things for tonight." I opened the package to find several smaller boxes inside; the first contained a pair of very realistic and expensive silicone breasts and a bottle of adhesive. I smiled and then understood why Mike had insisted I buy the strapless bras I had liked so much. I attached the breasts and was impressed with how well they matched my skin tones, I put on the red thirty-six "C" strapless bra I had gotten and marveled at the feel of the weight on my chest. I next put on a red and black corset, and red tanga panties. It was quite a task to tighten the corset, but I managed to shrink my twenty-six inch waist down to a twenty-four inch waist, I was very impressed by the sexy shape it gave me, garter belt and black stockings completed the look. I threw on wine colored robe and sat to do my makeup when I heard a knock on the door, a little nervous, I answered the door and found a pair of attractive young ladies standing there. I asked if I could help them and they informed me they were from the hotel salon and had been hired to come up and do my hair and makeup for me. They asked what I was going to wear for the evening, I showed them the black cocktail dress I had chosen and they complimented me on my choice. For the next hour, I was treated to the full efforts of these two young experts. A facial, manicure and cosmetics application made me look very elegant to say the least and the French roll they put my hair in, added a touch of sophistication. I went back to the box on the bed and looked again to discover a box from a jewelry store we had passed and in it I discovered a pair of clip-on diamond drop earrings and matching choker and bracelet. I put these on and the my dress and finally a pair of three inch spiked heels, I then sat and nervously waited for Mike to return.

When Mike did finally come back, he looked hot, the Brooks Brothers suit he wore was fabulous, it showed his muscular frame to its finest. Mike was speechless when he saw me, his jaw dropped, as he looked me over. The dress hugged all the curves of my shapely body; the heels accented my shapely silk clad legs. The crowning glory was the hairdo; the updo and curly bangs made my small-framed face stand out, in a word I was to die for. Mikes only comment was that he wondered if we should go out or just spend the night in the room. I said no way buddy, when I look this good, I want the world to see, considering that I had never really been seen in the public eye prior to this weekend, this was a very bold statement for me. We arrived at the restaurant and were led to a small private booth in a secluded corner. Waiting for us was a chilled bottle of champagne and a dozen long stem red roses, which Mike had picked up earlier. We ordered a salad to start and sipped our champagne as spoke. Mike explained that his parents were starting to pressure him to find a nice girl and settle down for at least the rest of his college years. If his parents were to discover he was gay, they would disown him, never mind the fact that his father would most likely kill him and his mother would have a nervous breakdown. This was the reason he wanted, no needed me to become his "girlfriend" and come home with him over the summer to meet his parents. While I felt for him, I was still hesitant to carry out this little masquerade of his. Mike upped the ante, he promised me a half million dollars when he took over the business from his father, which was going to happen right after he graduated, if he did not go on to play pro football. This along with a promise to get us an off campus apartment and his word that he would take me for many weekends like this one were all I needed. I would have given in for the apartment alone; the rest was just a bonus. I agreed and we changed the subject to more appealing matters, like shopping and such. We had a fantastic supper and headed back to the hotel where we changed before heading off to visit with Lisa, the waitress from the lounge. Mike did not really want me to change so to please him I stayed in the dress and allowed him to change into some jeans and a T-shirt, which I preferred to see him in anyway.

We arrived at Lisa’s place and were greeted with a drink and a smile, Lisa complemented me on my hot look, she went on to eye Mike like a unfed wolf, but politely commented on his handsome appearance. We sat in the living room, sipped our drinks and chatted for a while before I offered to spark a joint, Lisa said great, and offered to freshen our drinks. As I rolled the joint, Lisa slipped into the kitchen to pour us some drinks, unknown to us (until later that is) Lisa spiked Mike’s and my drinks with some kind of Spanish fly. We sipped on the drinks and smoked a couple of joints when I noticed a strange tingling in my groin, a quick look over at Mike’s crotch showed he was feeling something as well. Soon the tingling became a raging fire, and I began to squirm in my seat, all I could think of was getting some kind of relief, the only thought in my mind was Mike’s cock. This stunned me but I then noticed that Lisa had disappeared, she had been gone for quite a while it seemed. Mike did not even notice her absence, he had lust in his eyes and I was the object of his desire. Mike moved closer to me and slid one arm around me, by now I was lost in the passion. I leaned over and kissed Mike full on the lips, this was quite bold for me, as I had never initiated the kiss before, now it just seemed the thing to do. Soon we were locked in hard and heavy necking. Before long Mike’s hand was between my legs and sliding under my tanga’s and massaging the rim of my asshole, ever so slowly, the desire to feel him inside of me took over and my legs spread wider to allow him easier access. I felt something I had never before experienced once again, the desire to take his long hard cock in my mouth. Before I could voice my desire, Mike pulled my panties down and then reached for a jar of lubricant that had mysteriously appeared on the coffee table beside us, lost in the passion, neither of us thought to question it.

I felt a warm slippery finger at the edge of my asshole, I squirmed to let it get closer and before I realized it, it was buried deep within my ass. Mike began to slowly slide it in and out of my ass sending me crazy. I was lost in the moment and barely registered it when Mike slid another finger in to join the first one. I let out a gasp as my ass stretched to accommodate the new invader and very shortly, I was grinding his hand in an effort to drive him deeper into me. Soon I was in a rhythm of deep breathing and moans. This was a totally new world for me, here I was, a young heterosexual male who enjoyed dressing in women’s clothes, moaning in passion as a man finger fucked me. I barely noticed when Mike slid in another finger and he took this as a sign that I was ready for something bigger and better. Mike stood and franticly pulled his pants off followed by his boxers, letting lose his beautiful huge love muscle. I gasped and at the same time heard a quiet gasp from somewhere in the room, Mike’s cock was huge, a full ten inches long and it must have been two inches thick, and it wasn’t even fully hard. I gently took it in my hand, it looked massive in my small hands, my long red nails looked great wrapped around his sausage, I leaned forward and kissed the tip, leaving a perfect red lip print on his massive head. I looked up and smiled at Mike before opening my mouth and taking his head between my lips, Mike took over from there and gently slid deeper into my mouth. Going ever so slowly so as not to gag me, Mike explained that he in no hurry, that I should take my time and savor every second and inch. Mike began to rub my throat in a downward motion all the while keeping up a conversation, telling me how beautiful I was and how hot I made him. This went on for several minutes before I realized I could feel his balls pressing against my chin, I had taken his entire length, I had deep throated him. I could not believe I had done it, and from the look on Mike’s face, he was surprised as well. The knowledge of what I had done made me even hotter; I started bobbing up and down on his still growing and thickening cock. This went on for several moments until much to my dismay, mike pulled out of my stretched mouth, saying I had to let him calm down before he exploded in my mouth, he had another place in mind to shoot his load.

Mike stood me up and embraced me and kissed me, he then sat me down and then lightly pushed me to my back. Being new to this I was unsure what he was doing, knowing he was going to penetrate me, I believed he would take me doggie style, it was quite a revelation when he positioned himself between my legs and lifted my legs so my ankles rested on his shoulders. I reached down between my spread legs and grasped Mike’s cock and with a trembling hand guided his love missile to my waiting ass. I felt the head of his marvelous cock touch my quivering asshole and then released my grip and let him take over. Very slowly, Mike slid his cock into me until he forced my hole open, then with a swift thrust, he pushed it past my lips, it was only the head but it felt as if I was being ripped in half. I let out a little scream and Mike stopped and waited for my body to adjust to this foreign object trying to invade me, to my delight, my ass quickly spread to accommodate the size. The pain I had felt quickly lessened to an almost unnoticeable level and Mike drove into me with a fast and powerful thrust and he was buried to his balls in me. It was ecstasy; the feel of his powerful thrusts driving into me was unlike anything I could have imagined. I saw fireworks as he continued to pound me. I was sweating and groaning in pleasure as he rammed in and out of my now loose asshole, all to soon I felt him stiffen and then with a scream he shot his hot thick cum into my waiting ass. That was all it took for me to shot my load as well, with out being touched, my cock erupted, spewing out my own load of gooey cum all over my chest and belly. It was the most powerful orgasm I had ever experienced and I passed out for a moment. Mike collapsed on top of me, smearing my cum between us, with his still hard cock buried within me, we laid there trying to recover our strength.

A short time later, after we recovered enough to clean up and get dressed, we were sitting on the couch cuddling, when Lisa came in with a bottle of wine and glasses. She smiled at us and handed us videotape, saying relax, there are no copies and I wanted you to have a memento of what was obviously your first time together. Lisa commented on how I was glowing as we sipped our wine and as we prepared to leave, she hugged us both and wished us well and invited us to visit any time we were in town. When we returned to the hotel, Mike reached into his pocket to get the key and discovered a note from Lisa. Once inside we read the note in which she explained that she could tell we were in love and was pretty sure we had not yet had sex, she wanted to witness our first union so she spiked our drinks and cleared out to let us get wild. We looked at each other and soon we realized she was right, we were in love, that night we made mad passionate love twice more before falling asleep in each others arms.