This happened many years ago, I was in my early 20's. I had been seeing this girl on and off for a while, by this time our relationship had turned more into sex than any real "girlfriend boyfriend" thing. I enjoyed sleeping with her but we didn't have a connection emotionally. She came over to my apartment one evening at my request and we began to mess around, she was notorious for staying the night after we had sex and for some reason I did not want her to, I wanted to have sex and to have here leave so I lied to her and told her I had to work in the morning hoping she would take off after knowing that I had to get some sleep. Needless to say after we had sex we fell asleep and in the morning I awoke to find her still in the bed. I had morning wood and while she was still sleeping I thought I would wake her up with some morning sex. She was lying on her side in a pseudo fetal position facing away from me. I began blindly poking at her crotch with my penis but was having no luck finding her vagina, so I began feeling around with my hand assuming all this touching and poking would wake her up. She showed no signs of waking so I hatched a devious plan and decided to try and put my penis in her butt. I felt with my finger to find the butt hole and lined my penis up, (all the while in the back of my head knowing this was wrong and assuming she would wake up at any moment.) After lining up I began to push, and it started to go in... The feeling was intense, I was trying to go slow and not wake her up but I hit a point where I could not push any further with my hips alone so I wrapped my arm around her stomach for leverage and pushed again. One single stroke was almost enough to make me cum. As I finished the initial penetration she felt me (I'm not sure if it was my arm or my penis) but she woke up, turned her head to the right to see it was me wrapping my arm around her, I can only assume she figured I was spooning and laid her head back down. I was petrified and as much as I wanted to keep going until I finished I was scared because she obviously didn't realize that I was actively sodomizing her and was not sure how she would react. I waited what felt like 10 minuets but was in reality probably 30 seconds and pulled out, laid on my back and jerked off. To this day I regret not beginning to pump, I think because I was past the initial penetration if she had woke up she might have enjoyed the actual sex, although I do not know how long I would have lasted anyway. A year or so later I openly asked her if we could try anal and she told me she had never done it (to which I giggled inside thinking to myself "yes you have"). We did try it this time with her conscious and she ended the experience after 1 min citing pain as the reason. I respectfully stopped and we cuddled. We stopped fucking soon after and now flash forward years later she is married and has 2 kids. I am still friends with her on Facebook... sometimes I go through her pics and fantasize about that morning.