I started crossdressing when I was in high school. Small things that I had found or stolen: stocking, make up, thongs... I loved to look sexy, but I didn't feel gay at all. In high school I met a boy some years older than me. He was a great friend, we used to go to his house to play videogames since I didn't have a console. 

One day he started dating a girl, and we started to talk about porn and sex (I was virgin, so I was really interested in that topic). We eventually ended watching some porn. I had some magazines, but no videos, so it was awesome to go to his house, play for a while with the console and then watch some porn films. We jerk off several times before he proposed to jerk off each other, he told me his girlfriend kissed him a lot, but she refused to touch him because she was very shy, so he wanted to feel somebody touching him... I didn't like the idea. His cock was way bigger than mine (I've been always aware of the small size of my cock), not too long, but definitely thick. I didn't want him to touch my small cock, but I had and increasing curiosity about his cock. We started to touch each other while watching some porn. He probably get borred of my cock quickly because he stopped after a couple of minutes, I didn't care. His cock was totally hard in my hand and I was hypnotized by his cock and his face of pure pleasure. Then he asked me to kiss it, I though about his girlfriend, I don't know why but I wanted to be better than her... so I kissed the top a couple of times and looked again his face (I loved the idea of making him feel so much pleasure!). He asked me to suck it, but I just jerked him off.

I didn't go to his house for a week or so, I was very ashamed, though I was still crossdresing and imagining that he was seeing me being a girl... We returned to "normality" until one day he asked me to masturbate him again. I didn't think it very much, I wanted to see his hard cock again and his face, to make him feel pleasure. He just waited some minutes before asking me to kiss it again. After some kissing he grabed my head and pushed softly, his cock was entering a little bit in my mouth, I was shocked. I noticed, as the top of his cock was inside my mouth, the salty and strong flavor. His moan made me move my tongue a bit, and I discovered that he was moaning more, so I started moving my tongue faster. As I had seen in some movies, I took hiscock with my right hand and I started masturbating him while sucking the top. His cock was definitely thick and I was afraid of sucking more than the top. His hand in my head was doing a soft pressure, so I decided to suck a little bit deeper. I touched his cock with my teeth, but he didn't say anything. I was feeling very awkward, but I continued sucking his cock. 

I had seen that in the movies the girls got the entire cock in their mouth, but I couldn't get any more than the half... After a few minutes he started moving a lot and to moaning even more, and suddenly I noticed a shoot of semen filling my mouth. It was thick and the flavor was very salty and strong, much more than the flavor of the cock when I started to suck it. I thought it was very disgusting and I took the cock out of my mouth, though I kept masturbating him until he stopped cumming. I had no idea what I was going to do when started to cum (I didn't think about that possibility), but at least I expected him to warn me before doing it! I spat in a chunk of paper, but the flavor was still in my mouth. I asked for water to take out that flavour, but he didn't want to give me any, he was a little bit upset because I didn't keep sucking until the end. I had to go to my house with all the flavor of his semen in my mouth. The truth is that, in the following days, I imagined several times how it would have been to be sucking his cock until the end and to feel all his cum in my mouth. Something I had the pleasure to feel in other times, but not that day.