Rick's First Time by FantasyFreak

Rating: 86%, Read 28890 times, Posted Nov 14, 2014

Fiction | Anal, Bi-sexual, First Time, Male, Old Female, Transgendered, Transsexual

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 panties but there was a bulge. Emily then took her panties completely off and there it was. Emily had a cock. A beautiful cock. I couldn’t stop staring and I got an instant hard-on.

Emily started to touch herself and it was the hottest thing I have ever seen. I had no idea that she was actually a she-male. It’s usually pretty obvious, either because of looks or voice but Emily seemed like a normal woman. Emily took my hand and took me to my bedroom. She shut the door, turned around and then she started to undo my pants. I took off my shirt as she was taking off my pants and before I knew it, we were both completely naked. Emily pushed me onto the bed and started to dance over to me. She was the sexiest thing I had ever seen. Emily crawled onto the bed and she leaned forward and stuck her tongue into my mouth. I felt her cock touching mine as we made out passionately. Emily then started kissing my cheek, and then my neck, and then my chest, and she kissed me all the way down to my cock.

Then, without warning, she put the whole thing into her mouth. It was the best thing I have ever experienced and I was glad that I experienced it with Emily. She made me feel so good. I almost came after a few seconds of her sucking my cock. I guess she could tell that I was about to cum because she stopped. I decided to make her feel as good as I did so I gently laid her down on her back and I went straight for her cock. I started to kiss her cock all over and then I took about half of it into my mouth. Emily let out a moan and it made my cock jump. Her cock tasted so good and it felt awesome in my mouth. I sucked her for about a minute and then she stopped me and said, “I want you inside of me.” Hearing these words to me was like hearing that I won the lottery. Emily spread her legs and she rested them on my shoulders. I moved closer to her until our cocks were touching. Emily then reached for my cock and started to guide it toward her beautiful ass. I slowly put it in and we both moaned. It was so good. I went in and out and it felt great. Emily stroked her cock and moaned loudly as I fucked her hard. I liked how her ass tightened around my cock and it didn’t take long for me to cum. It was the biggest load I have ever shot out of my cock and I shot it deep inside Emily. Emily came at the same time and I bent over and licked up all of her cum on her stomach. After that we both laid on my bed and hugged each other tightly until we both fell asleep.

Rating: 86%, Read 28890 times, Posted Nov 14, 2014

Fiction | Anal, Bi-sexual, First Time, Male, Old Female, Transgendered, Transsexual


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