Sherlyn: Straight male is my favourite. What intrigued you?Rocky: Why is it your favourite?
Sherlyn: Because when I think of myself as a woman I only think of being with a man who wants me as a woman, not in a male/male way.
Rocky: Not sure what intrigued me, probably the fact that I’m 19 and horny. Side question: What do GG and TG stand for?
Sherlyn: GG is genetic girl. Which means it is a woman who was born as a woman. Although, a more broad term is CIS, which is cisgender, it is a term to describe male or females who have always been comfortable with their birth gender. TG is transgender. Which is someone who identifies as the opposite gender as to what they were born as.
Rocky: I understand that completely.
Sherlyn: It’s nice to know someone does. Feel free to ask me anything.
Rocky: Are you willing and want to do all things a normal girl would do? Receive sex (anal), give head, things like that?
Sherlyn: Yes, I do all those things.
Rocky: So what are you looking for from the guys contacting you?
Sherlyn: I’m really open. What did you have in mind?
Rocky: I really have no idea.
Sherlyn: What are looking for as an endgame?
Rocky: What do you mean?
Sherlyn: Have you ever thought about being with a TG? If so, what sort of things have you thought about?
Rocky: I haven’t really thought about it before.
Sherlyn: Oh, well now is your chance.
Rocky: That is very true.
Sherlyn: So, go ahead explore. Ask me anything.
Rocky: What would I ask about sex?
Sherlyn: Hmm, what do you think it would be like to have sex with a TG?
Rocky: I assume it would be fairly close to having sex with a cis woman. Except you can’t have vaginal sex, only anal. Which would actually be a bonus.
Sherlyn: A bonus, why? Have you thought about having anal sex before?
Rocky: I’ve given it once and I honestly fell in love with it when I did.
Sherlyn: Really, do you like it better than vaginal?
Rocky: I really think that I do! With enough lube of course.
Sherlyn: Yeah, lube is important. Why do you like it more?
Rocky: Well, for one no chance of getting anyone pregnant so I don’t need a condom and I can fill their ass with my cum. Then it’s also tighter than a vagina so it feels a lot better
Sherlyn: Sure, no worries on the pregnant thing. Not a concern with a TG at all, even after the surgery. Is it the fact you can fill her with cum or the tightness you like better?
Rocky: I think it’s the fact I can fill her with cum honestly. Although, I do love the feeling of stretching her out.
Sherlyn: That is very appealing on my end too. Something so intimate about a man’s cum seeping into my body.
Rocky: Really? Probably makes you feel more like a woman.
Sherlyn: Yes, I agree. It is very feminine I think. To be filled like that … with a man’s seed. Have you ever thought about receiving anal?
Rocky: No I haven’t. But I wouldn’t want to.
Sherlyn: Good answer, I personally don’t want to give at ALL. That is for the man.
Rocky: That works out well though! Would you play with yourself while you’re getting fucked?
Sherlyn: Some, but I’d mostly focus on you though.
Rocky: How would you focus on me?
Sherlyn: Well, I mean giving you a nice wet blowjob is focusing on you right?
Rocky: That is very true. I thought you were talking about focusing on me while I was behind you pounding you.
Sherlyn: Oh, well not much I can do in that position other than take you. Is that your favourite position?
Rocky: That’s true, which is why I was curious. And YES it is! I love bending a girl over to fill her up.
Sherlyn: I’m sure you do. So, I take it you’ve only done doggy. Would you be willing to try anal in a more missionary position or girl riding you?
Rocky: I would be up for trying it definitely.
Sherlyn: That is good. I sort of like the idea of watching your face as you enter me. It is a bit more intimate and personal.
Rocky: I understand. It would be a lot more intimate and personal that way. If you could go back to your conception and somehow change your biological sex to female, would you change it or would you still want to be born a biological male and go through this process?
Sherlyn: That is a really interesting idea. On the one had growing up as a man and having to deal with all the negative emotions of being trans is not something I probably sign up to do. It is a constant battle of depression, anger, rejection and apprehension. So, you would think the simple answer is yes I would go back and be born woman. On the other hand, I do like the person I am, not physically, but mentally and emotionally. I like my personality and growing up the way I did played a large part in that. I believe I have an appreciation for what goes on in the mind of a man, but also the ability to see it from the outside as a woman. However, at the end of the day I do crave a working 100% female body. I do find myself envious of things such as pregnancy and just the general self of knowing you are in the right skin. Essentially, if I went back and changed my sex at birth, I would have to sacrifice my personality and thoughts for a new sex. It would be a tough decision.
Rocky: I completely understand that. You would have different circumstances while you grew up which might change things. But you would have the female body you feel is rightfully yours.
Sherlyn: I completely agree that would be the best. To have a natural and female body that was mine would be amazing. I would be afraid I wouldn’t appreciate it enough though.
Rocky: You mean you wouldn’t realize how good you have it to actually have a female body? Like you wouldn’t know what it’s like to be trapped in the wrong body?
Sherlyn: Sort of. Sometimes, I feel like CIS women take their femininity for granted. That may be a bit unfair of me, but that is the sense I get. So, yes if I had been so lucky, could I appreciate it?
Rocky: I feel like you would be happier, but you might not understand exactly how lucky you are to have it.
Sherlyn: Yeah, I see your point. I would certainly be happier. So, that is probably the most important thing.
Rocky: I agree that it is the most important thing
Sherlyn: Yes you are right. I tend to really over think things.
Rocky: Life is simple; people are what make it complicated.
Sherlyn: Damn, people.
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