once upon a time, (a few years ago) I was dating this girl in high school for two years. I was 17, her 18, and up until this point we were both virgins. Like the ol' cliche, after a dance, we got a hotel room because we wanted to lose our virginity. I was super pumped, because at first she wouldn't even touch my cock, let alone let me see her naked. No blowjobs, no nothing (I was naive and thought all girls were extremely prude in high school), but finally, she agreed to the idea. that night after the dance when we went back to the room I had candles set up and the whole shpeel. We took a shower and I played with her tits (nice C-cups) and started rubbing her pussy and she said she was going to go get ready for me by the bed. I went out of the bathroom to meet her and she took off the towel I had around my waist and started giving me a handjob. at this point in my life I was probably around 6"x5.75". she said "wow, I've never seen all of it. When I squeeze it, it feels heavy as hell..." as she was stroking it (I'll remember this forever, it was my first compliment memory
). she laid down on her back and I asked her if she was ready. she said "yes." I put the condom on and pushed my cock up against the opening of her pussy. remember now...we were both virgins. I got probably half an inch in and she made a whimper. when I slowly put it all the way in past my cock head (about a measly inch), she started to tear up and then started crying. she kept saying "ow, it stretches me so bad." and "ow, it's too thick! it hurts!" every time I tried to put it further in past my head, she put a hand out on my stomach to stop me. eventually I decided that I needed to stop and we would try another time. she said she had no idea it would hurt that bad, needless to say there was a little blood. neither of us orgasmed, obviously.
a few weeks later we had my parents' house to ourselves so we decided to try again. I put the condom on this time and tried entering her again, with some difficulty. When I finally popped in, she let out a slow and drawn-out moan of discomfort. This time she let me put half of my cock in her, but then she said "okay, that's far enough." i asked if i could put it in further a few minutes later cuz i didn't want to just do it and have her mad at me, and she said "hell no, i feel like if you put it in any further my pussy will rip." after a lot more moaning and about 10 minutes of me half-thrusting (oy...), she asked me if I was going to finish soon because it was starting to hurt so bad. even with the half-thrusting, i managed to blow a nut. she had trouble standing up afterward. when we were laying there, she said she didn't like it, and that something was wrong with my dick cuz it was too big. lol. definitely some of the worst sex i've ever had. she was mad, lol.
a few months after that we broke up. we fought a lot and she was really stupid, thought she was a lot smarter than me cuz of a year's age difference, and a lot of other things I could list off but that's not the point. I've moved onto immensely better things since then, even though we ended up going to the same college. It might be a little wrong of me, but I take a huge amount of pride in the fact that I took her virginity and the size of my penis hurt her so bad. even when we make eye contact nowadays, there is a glimmer of suBathmateissiveness in her look. :s
