The first time I had sex was when I was 18. My boyfriend and I had been together for 2 years and we've always joked about 'doing it,' but never really took it seriously. One day while I was bored at home during the summer and decided that I wanted to visit my boyfriend at his house since my parents were at home and I knew that his folks were at work. Once I arrived, we were just hanging out and he ask if I wanted to make-out just kissing of coarse. I could feel that he was getting excited, but I don't think much of it because I could feel something poking me. I looked down and saw his shorts looked kinda weird. I love him so much because he said he was sorry it poked at me. I asked if he wanted to try it (have sex) he said ok, i think he was more nervous than me but that's ok because I have know him for so long there was nothing to be embarrassed about. Before I go any further in my story I need to say that when we would make-out I would touch his thing. This time I decided to try seeing his thing and boy it was huge, I mean it was fatter than a cucumber..I was very nervous after that, but at the same time I began feeling kinda wet in between my legs. I think it was because I was scared, but I wanted to know what it was all about. He put on a condom while I was taking off my cloths. We laid down on the bed while I looked at his penis, I could not believe the thickness of his penis. We began kissing again and his hand found its way between my legs and when he touched me I felt very wet, my body really was quaking during the time he was touching me. He slowily moved between my legs and he stuck it in and boy it hurt really bad, but he was trying to be very gentle and sliding in and out carefully until I felt ok, but it did hurt. After the first time it did not hurt as bad we did try different positions and found out that me being on top is the way for me. After a while, sometimes he would bend me over and I would really get it then. I think its better when you are in love with the person then it make the experience more pleasurable. I have tried anal sex whit my boyfriend and unless you know what you are doing don't try it. My boyfriend's penis is 8 inches long and I usually have to lubricate before I have anal sex.