Straight Male / 20
See Her In My Dreams
I met a transwoman at a small gathering held by a married college couple I know from school. We were swimming, cooking barbecue on the grill, having some drinks, in my case, lemonade and water, I don't drink alchohol. Dee was incredibly pretty, not just pretty she was beautiful. In her bikini she was showing a perfect body, great legs, perfect ass and I found myself staring. We talked quite a bit, were partners in card games. Inside the hostess asked me what I thought and even though Dee was 4 years older than me, I thought she was really great. We were easily talking and enjoying each others company, and physically, she was a knockout.
The hostess told me that she shouldn't say anything but she thought that Dee and I would get along famously and we were. However; she swore me to secrecy that I wouldn't say anything and let Dee tell me, but Dee was a transwoman. Born a man, was pretty much what we called a sissy growing up, crossdressing when she could, then eventually went about making the change. The hostess said that it wasn't something where she was trying to pull a joke on me, or anything she genuinely knew that we had the same interests, would get along, and from the past she knew what type of body, face and hair attracted me. Besides, what could it hurt to remain nice to her for the rest of the evening. It's not sex, it's four couples, all with their clothes on, enjoying each others company.
I took Dee home, she asked in the car if I knew about her, and I told her that I did. She assumed that I wouldn't be seeing her again, and told me how nice it was to spend an evening together and she understood why it couldn't happen again. I felt bad, and told her that it may not lead to a relationship, or sex, but we could go out and date; if she wanted. She did and we did.
No sex, though we have started kissing, and quite frankly in my apartment on a movie night I did pull out her breasts and was sucking and rubbing on them. After that she told me we didn't have to go further but if I wanted she would use her hand to relieve me. I haven't crossed that line yet, but despite what I do or think, I'm straight. I have always fucked women or girls, when I was younger. I've never even done the old "I'll show you mine and you show me yours" with another boy when little. I have no desire for sex with a man. But I'm dreaming about Dee, I've seen her tits, I've seen her body in a bikini, we've dated, and she seems all woman and I dream of having sex with her, missionary and me in her ass. I've always loved anal when I could find a girl who lets me do it. I'm having sex now off and on with two women, one 18 the other 21 but neither is as feminine and beautiful as Dee. I don't have sex dreams about them, just imagine fucking Dee.
The hostess told me that she shouldn't say anything but she thought that Dee and I would get along famously and we were. However; she swore me to secrecy that I wouldn't say anything and let Dee tell me, but Dee was a transwoman. Born a man, was pretty much what we called a sissy growing up, crossdressing when she could, then eventually went about making the change. The hostess said that it wasn't something where she was trying to pull a joke on me, or anything she genuinely knew that we had the same interests, would get along, and from the past she knew what type of body, face and hair attracted me. Besides, what could it hurt to remain nice to her for the rest of the evening. It's not sex, it's four couples, all with their clothes on, enjoying each others company.
I took Dee home, she asked in the car if I knew about her, and I told her that I did. She assumed that I wouldn't be seeing her again, and told me how nice it was to spend an evening together and she understood why it couldn't happen again. I felt bad, and told her that it may not lead to a relationship, or sex, but we could go out and date; if she wanted. She did and we did.
No sex, though we have started kissing, and quite frankly in my apartment on a movie night I did pull out her breasts and was sucking and rubbing on them. After that she told me we didn't have to go further but if I wanted she would use her hand to relieve me. I haven't crossed that line yet, but despite what I do or think, I'm straight. I have always fucked women or girls, when I was younger. I've never even done the old "I'll show you mine and you show me yours" with another boy when little. I have no desire for sex with a man. But I'm dreaming about Dee, I've seen her tits, I've seen her body in a bikini, we've dated, and she seems all woman and I dream of having sex with her, missionary and me in her ass. I've always loved anal when I could find a girl who lets me do it. I'm having sex now off and on with two women, one 18 the other 21 but neither is as feminine and beautiful as Dee. I don't have sex dreams about them, just imagine fucking Dee.
- That's Juicy! 16
- Remove It! 3
