Haha I was 17 when I lost it, was waiting (doing the proper thing) and waited untill she was legal and everything, then that night, we were at my house, I'd convinced the parents and sister to be out, had the moodlighting, candles, everything, I mean, we'd had this planned. Took a bath together... dried each other and went to my room naked. She kept the towel but I was starkers XD. Anyways, she layed down on the bed nervous and faced away, not saying much, I asked if she actually wanted to go on and she said yes but didnt seem into it.
Heres the funny thing, before I psyched myself up enough to do it, I must have gone through three condoms where I'd waited so long each time I'd lost the hard on and you know how the box says something about changing them etc... Anyways, We had sex and I believe with her not saying much and me either... it was a terrible night, I think I came as I pulled it out as she had this look of so much pain on her face. Disposed of the condom and we went to sleep with the cuddling of deathly silence... I cried that night because for some reason, her face of pain went over and over and over in my head, that I had caused it, that she must not have wanted it really, that I'd raped her... She actually slapped me when Id told her how emotional I'd been that night, and said "Im a big girl now I can make decisions, if id wanted you to stop, I would have" and we were fine with each other...
Sex was never good with her, it always caused her so much pain. we just ended up doing other stuff instead lol.
Theres my story... Sorry to bore you lol