Where it happened: mom's bedroom
Langauge: english
Sex: Female
Rating: 5
Category: Straight
Growing up, I always knew I wanted to be a girl, but alas I was born a boy. Now that I am physically a woman, I had SRS three years ago, I just thought I would recount the first time I was with a boy…very special to me because I realized then what I really wanted. Anyways, it was summer and my mom was away for two weeks. My friend from school got clearance from his parents to spend those couple of weeks at my house. I was always very small for my age, and had a feminine face and he had told me so before…”you kind of look like a girl” that sort of thing. I think we both knew what we had in mind when I invited him over. Down in the basement, my mom kept all these donated clothes that were for the church…an awful lot of women’s clothes, jewellery, etc…even a couple wigs.
So me and him were sitting on the couch playing video games and he touched my ear, and brushed my hair. We just looked at each other and then started kissing, gently at first, then more passionately…his tongue inside my mouth. I said hold on a sec I want to dress up, and told him about the clothes in the basement. I went down and dressed up, in bra with socks, panties, and a flower pattern summer dress. I also found lipstick and mascara (yes, I had done this many times before when my mom was away).
Then I went up stairs and sat on the couch with him, and we started kissing again. I was passive and let him control the situation. After kissing for awhile, he pushed down on my head and I knew what he wanted…so I unzipped his pants and pulled out this enormous penis dripping with precum. I hesitantly put it in my mouth, and it tasted very salty but I liked it. I went down as deep as I could, as he had his hands on either side of my face. He told me it felt good, and I was so pretty, it made me go harder and deeper, I even gagged a couple times. Being that we were both inexperienced, he came without warning while I was deep on him and it filled my mouth. Surprised, I almost threw up but recovered. It was all over my face and all in my mouth, but I swallowed what I could. At this point, I would have done anything to please him. I also wanted him inside of me but that would have to wait. We sat back and I told him I wanted to be his girlfriend. He said that would be fine and we started kissing again. It wasn’t long before he got hard again, I helped with my hand, and asked him if he could put it inside of me. We found some lubricant (I don’t remember what) and I rubbed it on his penis and then myself. I laid back on the couch with my legs open and he laid on top of me. He entered me and it really really hurt, but he was nice and kept asking me if I was okay and told me how beautiful I was. We weren’t just having sex, we were making love, and while he was fucking me he was also kissing my mouth, my nose, my ear, my neck…it hurt but it was wonderful too. After about ten minutes he came again and I swear to God I came too like a woman. I felt it all over my body as he came inside of me.
So after it was over I lay on top of him and we dozed off watching TV, falling asleep in his arms. At this point I realized that not only I wanted to be a girl but I was in love with him too. About an hour later, I woke up and he was still asleep. I pulled out his penis and put it in my mouth again, waking him up. This time I went all the way and let him cum in my mouth, and I swallowed it all. It was amazing how he could cum so much three times in two hours! After I swallowed I looked up at him and told him I loved him. To my joy he said he loved me too…I don’t know if it was real but it seemed like it at the time. So I stayed dressed as the girl I felt like and for the next two wonderful weeks we were pretty much husband and wife. I was pretty passable for a female, and we even went out to the movies and to the mall a couple times, holding hands. Eventually the two weeks ended and so did our relationship…
After high school I had surgury and became a real girl, a couple years later I married a real husband, whom I love and have a very normal sexual relationship. But I will always hold Tom, and those glorious two weeks, very near to my heart as my first real love.
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