My "Girlfriend"

I'm 15 and go to a pretty progressive high school in California. There are lots of different cliques in my school, one of them being about a dozen or so transexual girls (t-girls). There are a few senior t-girls and a couple of juniors, but most of them are my age (14-15) freshmen and sophomores. I'm not sure why this past September, we had a whole new mess of them because I don't think any of the junior high schools in our district allow this sort of thing.

I was told that since most people don't know you when you come to high school, this is the time to switch over. I asked my dad (he's pretty cool) about what was it like in his time (back in the early 70's) and he said there were t-girls during that time, but they hung around the gay guys in school and usually didn't look much like a girl--more like a femine guy wearing makeup and girls clothes like jeans and halter tops.

After seeing some of these babes last year, I started to visit some of the t-girl websites over the summer and downloaded a ton of pictures and was masturbating like crazy everyday after I came home from school and in the morning before leaving for school. When this semester started, it got even worse because there was this really cute t-girl named Jessica sitting next to me and she'd be wearing some pretty sexy stuff like all of the other female girls in class. She's one year younger than me (14) and she has these small, nice sized breasts. Once she wore this loose halter top that you could see inside by the arm if you looked from the right angle and my desk was in that perfect spot. So for the whole class, I just kept stareing at her pink nipples and nice tits that she caught me once or twice cause she turned to me and gave me a really big smile. This is when I had to be excused to go to the bathroom and jack off. It was one of the best cums I ever had!

I'm pretty shy with girls, much less with someone like this cause she's really beautiful. She could be the younger sister of Jessica Alba, the one on that series Dark Angel. Her real name was Jennifer back in junior high, but everyone started to call her Jessica, so she started using that name at our school. Anyway, the first time I even talked to her was about 2 weeks into class as I totally lucked out as I got to be her lab partner.

In my school, most of the guys are pretty cool with the t-girls and everything--I guess because they look so much like the other girls. The only rule that goes around school is that you don't not tell the guy when you meet them that you're a t-girl. For the most part, most of the guys know anyway. And these girls usually either hang around with themselves or some of these kind of off the wall guys into heavy metal and stuff like that.

Anyway, Jessica and I got to be pretty good friends in class that I didn't take too much heat from my friends about hanging around with her. About a month ago before Christmas, we had a big project due and we had to work with our lab partner alot. So one day, Jessica asked if I wanted to come over to her house and study, so I didn't think much of it. She only lives with her mother and the mother doesn't get home until after 6:30 or sometimes even 7:00 that we had the whole house to ourselves. She and I laughed alot and so I got really comfortable with her. We ended up kind of like wrestling on the floor and that's when it happened. I started to get this huge hard-on that I had a hard time hiding it and as we wrestled, my hand would brush up against her nipples which were getting hard. She must have known about my hard dick because she would "accidentially" brush her leg or foot on it making it more hard that it really was.

When we stopped for a moment, she just looked at me and started laughing and said I had better do something about "my problem". I was kind of embarased but then when I looked down at her croutch, I could see an outline of her dick. It then hit me that she really was a t-girl and not a real girl. I knew this of course, but I guess it didn't hit me until just that moment. I also started to laugh and told her "What about you?"

We just stopped laughing, looked at each other and then bust out laughing full on again and started wrestling again. She got me so our faces were next to each other and then she sort of stopped and just looked into my eyes and we just started kissing. We must have kissed for a long time and then she stopped again and took off her halter. I couldn't believe my luck because her tits were perfect! Small, like the size of a apricot that was perfect for her sized body and nice pink nipples. I started to suck on them like there was no tomorrow.

I'm not gay or anything like that and the only other contact I've had with another guy's cock was when I was 13 with some close friends in school that I still hang around with. We would jack each other off, but never did any sucking or in the ass or stuff like that. That went on for the whole summer and then we would only do it once in awhile in the last couple of years.

Anyway, Jessica and I were getting so hot that the next thing I knew, she unzipped my fly and pulled my dick out and started to give me a really slow handjob. She knew just when to stop and start again and did this for about three times until I was begging her to let me cum. She just laughed and said to wait. During this time, I was rubbing on her hard dick through her pants. All of a sudden, she unzipped her pants and pulled her dick out. She had a dick almost identical to mine--about 5-1/2 - 6 inches, circumcised, but she also was completely hairless down there. She put my hand on her dick and I instintively started to jack her off and she began to moan. I did this for about a minute or so, wanting to do the same thing to her about not letting her cum, but before I knew it, she got up and straddled me so our dicks were touching each other. She took both of our dicks and rubbed them like sticks together and then rubbed the undersides together, just under the head. I couldn't hold back any longer and I started to shoot gobs and gobs of cum. Jessica put her dick up to mine and milked the both of us and that's when she started to cum too. It wasn't has much as mine, but it was still pretty creamy and thick.

After that, we laid around for a few minutes and by that time, I had to go home for dinner. Shit! The next day at class, we were closer and would be kind of touching each other on the shoulder or hands that the other kids started to notice. At that point, I didn't care a flying fuck so I kissed her in class. Pretty soon, it was all over school and at lunchtime, my friends started to razz me. But the four other guys that I used to masturbate with just came up to me and ask me how it was. I told them it was AWESOME! They accepted it right away and now two of them are going out with a couple of other t-girls in school and the other one wants me to ask Jessica if she can introduce him to her best friend. That guy is one of the captains of the football team and kind of popular in school, so nobody's saying shit anymore. Pretty cool!!!

One last story happened over the Christmas hoilday I want to tell you about. It got to be that when we went over to Jessica's house, we knew that the mom wouldn't be home, so we started having all kinds of sex all over the house. The only thing that we hadn't done up to that point was fucking in the ass because I wasn't sure of that. But we would do mutual masturbation alot and my favorite was "69". Yes, we got into that too and I even like the taste of her cum too.

One day, Jessica says she wants to show me something. We strip down naked and get into her bathtub, but before we do that she takes a hand towel and wraps it around the shower head so the water comes down in one stream really hard like. She tells me to kneal down in front of the water so my dick is sticking out and put it under the water. She gets behind me and puts her hand under my dick so it rests on the palm of her hand and then she had me lean in. When my dick hit the water, It felt like heaven! It was like jackin off without having to do anything! Before I could get into it, Jessica pulled me back and said wait. Everytime I've heard that from her I knew something even better was going to come. With her behind me, her dick was also super hard and she put on some lotion on the head of her cock and started to rub it between the cheeks of my ass while pushing my dick back under the water with her little hand under it. At that point, I didn't care if she fucked me, and a minute later, I felt the head of her dick slip inside my hole. The stimulation of the water and of her dick in my ass going in and out gently bought up the biggest orgasum to date. I yelled out a big "OH!" and started cumming and cumming like there was no tomorrow and with the water pounding my dick, it was like I was being milked without being touched. This apparently made the muscles in my asshole contract everytime I shot that it squeezed her dick and made her cum too. She yelled out and shot a huge load in my ass. I was so worn out after that that we had to rest before we could do anything else, so we just spent the time kissing. Since it was getting late, I wasn't able to pleasure Jessica like that until the next afternoon when I got my chance to put my dick up her ass. I can't tell you what an awesome feeling it is to feel her ass muscles clamp down and release over and over again that made me cum inside her and I could also feel her dick spazzing in my hand as she came with the water hitting her dick.

I'll write back to you later about some other times we had, but for now this is all. In closing I would say to anyone to try a t-girl, especially if you're still in high school. Don't let other people bother you as you might be having more sex than all of your friends combined.