Fingered and fucked my girlfriend's ass in her sleep. [m/f] | 2016

So my girlfriend has been a bit 'off' lately which means no sex... Anyway I've always had a thing for ass play but my gf doesn't really like it. We tried anal once and never again because it hurt her too much. In the past I've dry-humped her and groped her ass a little in her sleep but never really got too far because she usually wakes up, last night was a little different. She was lying on her side facing away from me so I started off with the usual groping her as gently, testing how heavily asleep she was. She was wearing loose cotton shorts and no panties. I slowly put my finger tips up the one leg of the shorts and softly cupped her bare ass-cheek. At this point I was getting hard. I began gently squeezing her small soft ass-cheek, with each squeeze my fingers edged closer to her asshole. I was sure she was going to wake up at this point as I was getting kind of rough but to my surprise she didn't seem to budge. Soon my finger was toughing her asshole. It felt soft but was slightly clenched, I started slowly rubbing it. I decided to pull down her shorts so my hand could reach her ass from a better angle. I also pushed her head and feet away from me so her ass was a bit more open. I noticed her ass was getting wet and she was breathing a a little heavier. I knew she was still asleep though (she 100% would have made me stop). My hand was back on her ass and my index finger was rubbing her asshole which seemed to be responding by clenching and letting loose as I rubbed. I slowly pushed my finger about an inch into her asshole, she let out a soft breath and arched her back so her ass was a bit more open. I pulled my finger out and pushed it back in the whole way. She let out a tiny groan. I continued this for a while, in her sleeping state she seemed to like what I was doing, she was even slightly moving her pelvis in a grinding motion and still occasionally clenching her asshole. It was so warm inside her and felt so good I never wanted to stop. As I fingered her ass more vigorously I began masturbating. When I was almost finished I pushed her onto her stomach gently climbed on top of her and held open her asshole open with my thumb and index fingers, I put my dick right on her now wet, throbbing asshole and pushed until I was inside her, a few thrusts later I came. The next morning we went for breakfast, she didn't say anything so I assume she was really asleep.

Best night ever!