My ex (F19) is a very tiny girl.  She is one of those girls that I could put my two hands around her waist and they would touch at the finger tips. Needless to say being a bit bigger myself it took some time for her to get used to me. For a while I would have to go very slow and she wouldn’t be able to take all of it. Never did fit it all in her mouth. Despite that I really enjoyed everything about her; she had the most beautiful personality, the cutest little breasts, and this face that could go for innocent to sex kitten in a heartbeat. She had a sneaking around fetish that could never be satisfied, so we often were in small or cramped places trying our best to be quick and get away with what we can. That is how the mistake happened.

After a while she was able to take me deeper and kind of fast, but I could never get going too fast due to her size vs mine. One night however, we were going at it in a place we never should have been. I was a bit nervous this time about being caught as it was very public and we could be walked in on if we made too much noise. This turned us on so much that I kept going at her from behind, faster and faster. I had my body pressed on top of hers and her legs apart but not enough to give us lots of room. I lifted her hips so I would be going at more of a down angle and she started to lose it, just moaning and screaming into her rolled up jacket. This just made me keep speeding up faster and faster.

That’s when I lost it…  My cock slipped away from her pussy and I didn’t aim right or something when I went back and slammed hard into her (then) virgin asshole. It hurt like hell for both of us, because I didn’t make it all the way in and it felt crushing on my cock. She let out a loud scream that I was sure had us busted. I did not get all the way in, I mean she wasn’t ready and it was tight, but she was instantly in tears. I told her it was an accident and she believed me, yet, could not stop crying. Realizing we could get caught and soon I put all her clothes into her bag, pulled up my pants and put my coat around her. I still don’t know how I got her out without anyone noticing but got her back to the car that was just outside the door (if you do public sex have two escape routes ready).

The car was parked in an obscure place you had to want to go there to find it. So I knew we were safe her and I just held her inside my coat as she cried for a half hour. It just hurt that bad. I did inspect her and clean her up, that didn’t help much. I just held this crying naked girl in the back seat of my car for a half hour or more.

The confession is:

I loved it.  I feel bad I hurt her, yes. Did I love that she was crying naked and helpless in my arms; I can’t explain why that turned me on. In all thinking it shouldn’t have. The fact she was hurt wasn’t the turn on but that she was so vulnerable and naked somehow made me want her in ways I have never been able to explain correctly. It didn’t make me want to have sex with her in that moment; thinking about it now it does not make me want to have any kind of sex, but it gets my heart going. I never wanted to hurt her like that again, we never even talked about it or attempted anal after that, nor did I want to.  It was something about the state she was in and how the only thing she could muster herself to do was to hold on to me while she cried.

We would eventually move on to some bdsm type things. We did keep the “public kink” but became a lot safer with it and realized our idea of having more than one escape route to the car was a really good