My First Time...

When I was younger I had a theory about sex. That if I didn't try to make my first time this big special event, that I would prevent myself from falling in love and being forever broken by my first. Even before high school... I would have to say that I was more sexually curious than most but never acted too quickly on them. I just surrounded myself with promiscuous friends that allowed me to exlore with the support of some friends. So in high school when my friends starting having sex, I fell witness to the torment and the questioning that everyone would report to me and it all seemed that the more they liked the person they were sleeping with, the harder it was for them to deal. So I was 15 and the last in my circle of friends to lose their virginity. So following my logic, I wanted to plan it in a way that I would remember but save the worry afterward. There was a boy who was a year older than I was and I found him to be very cute..... I was quite infatuated, he played football and was the older brother of a boy in my class so, we were around eachother. He was the one I was going to experiment on so to speak. He was the first one that fingered me, the first guy I ever jacked off and my first *******..... so lets just say I was quite inexperienced. After that we drifted apart for a while. A few months later, I finally worked up the courage to finally do it. My favorite holiday being Halloween, and it being right around the corner, that's when I decied to do it. I had it all planned out, I would go to his place and he would take me to do the deed. So that day during school, on halloween, we talked about it and he told me to come over at night and we would go for a walk. I was in costume and everything, short skirt, corset, the whole thing. We walked down the street together, it was just after dark and I was very nervous. I followed him around to where the houses ended and there was a large hill, we climbed over a wall to make it to the hill. When we finally got down to it, my heart was pounding as we started kissing. I remember it was cold and we were outside, I didn't even take off my clothes he just started to pull down my panties and got on top of me. I lay there waiting for it to happen. I remember the pain, because he couldn't even get it in all the way. He grabbed his **** with his hand and brushd the tip up and down to try to get me more wet. He stuck it in somemore and still had the same problem. After some time struggleing with it... it was over. He laid on top of me for a moment and then rolled to my side. He asked if I was ok, all I said was yes I'm fine, and we laid in silence a few moments. We started walking back, he went home, I met up with a friend and my parents picked us up and we went to dinner. I wondered if I looked different or anything because I didn't feel any different. Over the next two years, I had a few more experiences under my belt and I slept again with the boy I lost it to, twice in fact and both other times, including the first time absolutly sucked. So now that I'm older I know he was just not the right choice, because he couldn't find the button if you hit him in the head with it.

Thinking back on it now, I feel I may have jipped myself the real experience of loosing my virginity, but it did give me a real insight on sex and relationships. Not to bad to walk away with.