First Time

It took me a while to know what my sexulity was. When I was younger I thought I was bi but liked girls more. I guess I was so confused because I was always secretly feminine. I started crossdressing when I was around 10. I loved feeling girly and submissive. I used to think submitting to a man's cock was the ultimate way of being submissive. Later on I learned you can be submissive to women. I won't get into all those details but I learned I am not gay, I'm actually only attracted to female presenting people. However, I've had one gay experience which helped me realize this much later.

I used to have this best friend from kindergarten to end of middle school, who I hung out with all the time. I used to go to his house every weekend and sleepover. Sometimes I would go hang out during the week. He would also come to mine but we were mostly at his place because his parents and siblings would usually leave and it was only his grandma who "took care" of us. Sometimes they would just leave us by ourselves.

When we got to middle school we both got increasingly horny. We would watch porn together sometimes. It was probably around the beginning of my last year in middle school that I went to sleepover at his house one day. I remember, weeks prior to this incident I was thinking of introducing him to my crossdressing hobby by bringing him some panties but I feared he might have a bad reaction as he had never shown any sign of interest in that. Anyway, that night it was only the two of us in the house. It was late and we went to his room to sleep, he got on his bed and I had to sleep on some bedsheets and blankets on the floor. I was really horny and feeling really submissive. I was really curious, I wanted to feel a cock in me. My nerves were high and I had that feeling when you know something is wrong but you want to do it badly, all of my sense were firing. I waited about 25 minutes after we had gone to bed. I let my eyes adjust to darkness, there was only a bit of light coming from one of the windows. He usually went to sleep quickly. I got on his bed and got on top of his legs. I pulled down his pants a bit. He had not gone to sleep but he sounded sleepy. He stopped me from pulling them all the way down although I could already see his dick. He laughed a bit and asked "what are you doing?" I pulled them a bit more until his half erect cock was out. I grabbed it and asked "do you want me to suck it?" He said "sure we're young." I put my lips around his now fully erect cock. The taste was bad, tasted like dirty dick. But it felt good. His cock was bigger than mine and it made me feel more submissive. I was fully hard while I sucked him. I didn't suck him for long maybe 1 or 2 minutes but I salivated quite a bit on him. I was precumming quite a lot. I took off my pants and trousers. I grabbed my precum and rubbed my ass with it. Naively, I thought I could have anal sex with little lubrication. I turned around and put myself in a squat position. I guided his cock into my hole. The tip definitely entered a bit but I realized it was too hard and stopped. When I got off I felt the pain from what little had entered. That was enough to turn me off and stop completely. I was hurting for a little while until I went to sleep.

Next day, we did not talk about it and basically pretended it never happened. But, after that day it took a while for us to hang out again which was weird from him. It was about 2 months later that we hung out again. I had no plans of something like that happening again but I really wanted to. I was not attracted to him at all. But the idea of playing with a cock was so enticing.

Maybe I'll make a part 2 for the next time we saw each other.