Where it happened: hotel in a Chicago suburb
My “first” was really not great at all. I was 21 but I had a 16 year old girlfriend from England who came to the US to see me. We had met overseas a few years before and I had seen her a few times. We had planned on having sex for about 3 months, ever since I spent a week with her in London. We went to Chicago for the weekend and stayed at a hotel near the interstate in the suburbs. So here we are for the first time we ever have sex and she was having her period. What the fuck?! We got in bed and I put myself inside of her and then she cried and bled and pushed me off of her and didn’t want to do it any more, even though I begged for it. Although I was inside of her I never came, so does that count? Can you believe that we never tried again? She went home and we moved on to other people. Luckily I got drunk with a girl at a college party about a month later and had sex with her but since I was so drunk I just got hard, fucked for over an hour and didn’t come again! This shit was getting old. I had penetrated two girls but hadn’t ever shot my wad. Christ. A few days later we did it again but then I came right away. Although I lost my virginity late and the first two times were so bad, since then I have made up for it by having sex with anybody I can, even fat girls. They’re easier to get than good looking ones. I’ve had more women than anybody I know.