1. Rick's First Time


    Date: 7/3/2016, Categories: Fiction, Anal, Bisexual, First Time, Older, Trans, Trans, Author: FantasyFreak, Source: sexstories.com

    Ever since I was young I had a constant urge to grab my penis and stroke it. I was constantly masturbating (even in school). At 13 I was so curious about sex and when I was 14 I discovered that I was bi-sexual. My name is Rick and I am now 18. I am not the most handsome of men but I wouldn’t think of myself as ugly or unattractive either. I’m still a virgin, but not because I am a complete loser. It is because I have not decided if the first time should be with a man or a woman. I want to lose my virginity but since I am bi, I can’t really decide between guy or girl. The thing I like about men is their cocks. I would like to suck and get fucked by a cock but I am not attracted to abs or handsome faces. That is why I like women. I can get off to the face of a woman pretty easily but they don’t have beautiful cocks. So I have decided that the person that will take my virginity will have a penis and a woman’s body. She-males, trannies, traps, whatever you want to call them. I have never been as attracted to females or males as I am to she-males. The only problem I have is that beautiful she-males are hard to find who would be willing to fuck me but I am okay with waiting. I am not going to go search for this person, I am just going to wait for someone to come to me. My best friend, Emily is one of the only people that know about my sexuality but she does not know about the whole she-male thing. Emily is a very pretty pale skinned, blonde and tall woman. When I describe Emily to ...
    people, they usually think of her as an 18 year old like me but they are usually surprised when they find out she is actually in her 30’s. For most people, it is weird to be friends with someone so much older than them but not for me. We met when I was 15 and going through a tough time. She was the one that was helping me deal with everything because she was actually my therapist. I know it’s weird but she really was the only friend I had so even after we stopped seeing each other for therapy sessions, we still hung out a lot. It was mostly because I still needed her to help me. So once in a while I would call her and we would go to a restaurant and talk. She was like a second mother to me and we tried to keep in touch as much as possible and we still do. But now we hang out much more frequently and we have started to enjoy each other’s company. One day, I was hanging out with Emily at my house and we were playing video games which she surprisingly loved. I guess I must have started doing badly in the game because Emily turned to me and asked if I was okay. I decided to tell her about my whole virginity thing and how I want to lose it to a she-male. I could tell that something was bothering her after I said that but I didn’t think it was because she was weirded out or anything. She then looked up and kind of half smiled. “There is something I have to tell you,” She said. “but it might be easier to show you.” She pulled down her pants and to my surprise, I saw a bright pair of ...
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