I was the first guy to play with my ex-girl friend's asshole.
This story happened a couple years ago. I was dating a girl who was four years younger then me (I was 24, she was 20.) I was finished with school, but she was still attending university. Sadly, it was also a long distance relationship, so the times I got to see her were very few, but very special.
This happened one time when I came down to visit her at the school. She's was an incredibly cute girl. Very outgoing, funny, nerdy and loving. She was an average build, with curves in all the right places. Her breasts were just about the size of softballs, making them very fun to grab. But honestly her best feature was her face. A very kind smile, beautiful blue eyes (usually with glasses) and very long, big, brown curly hair that went all the way down past her shoulders.
She talked her roommate into staying somewhere else for the time I was visiting her, so we got her dorm room all to ourselves. After a particularly intimate night, the two of us fell asleep naked in each others arms. Now, I have a bad tendency to move and roll around in my sleep, and occasionally wake up in a drowsy state before falling back into deep sleep. It was late in the night (or very early in the morning) did I stir from my sleep in this fashion. My girlfriend was lying on her side facing me, and I was lying somewhat on my stomach (with my head facing in her direction) and my left arm lazily curled up over her.
Being in my drowsy state, I was about to try to fall asleep again when I heard my girlfriend weakly ask me, "do you like touching me there?"
It was then I realized two things. 1) My girlfriend was clearly awake as well and 2) My arm that was draped over her was over her ass. My arm curled around her checks and my fingers were actually touching very close to her asshole. Maybe I was rubbing her in my sleep, and this unusual touching woke her up.
Now, I didn't know what to say to this. I've never experimented with anally stimulating my partner before, although the idea had crossed my mind. I always wanted to ensure my partner got the best treatment in bed that I could provide, so I never ruled out the option. This was the first time the issue had been brought up. And as the seconds went on in that dark room, I became more aroused by the prospect of touching her cute little asshole.
So I responded quietly, "do YOU like me touching you there?" And with that I slowly and gently started to move my fingers to her hole. Using the palm of my hand to gently pull her ass cheeks apart, my index finger gently massaged the outside of her puckered asshole. It was clenched tight, and while doing this blindly I could hardly even tell where the opening was. It's clear she was very nervous about me touching her there; clearly, no one had done this to her before. And this was new to me too. It was incredibly hot and I was incredibly hard just from those beginning touches.
I kept massaging her hole as she barely even moved, or said anything. It almost seemed as if she was even holding her breath. Finally she said something to me. "It feels...weird..."
"Weird" seemed like the right word for her. At this point in our relationship I'm pretty sure I knew what she meant by that. It meant, "I don't know how I feel about this yet." So I decided to get a little bolder. As my index finger circled gently around her asshole, I noticed she was beginning to loosen up just a bit. My finger slowly got to the center of her tight opening and I slowly inserted the tip of my index finger. Only a tiny bit, and her ass instantly tightened up around my finger. As I inserted my finger, my girlfriend let out a very breathy gasp. I just paused there for a second and allowed her to get used to the first thing to ever penetrate her ass.
After a brief pause, I slowly started to moved my finger out, and then back in again, no deeper than before, but it appeared she wasn't ready for that. "Ok," she said to me, slightly overwhelmed at this point, "that's enough kinky stuff for tonight."
And of course, I didn't want to push her to anything that made her uncomfortable, so I stopped. "Ok," I said as my finger exited her asshole. It was also incredibly late, so I repositioned myself, and tried to go back asleep once again, even though I was blue balling like crazy.
The next morning however, was a little different. We lazily started to wake up, and casually chatted in bed. Talking about what we might do that day, and other things. The topic of me playing with her asshole last night didn't even come up. We began to get changed, and I was about to start the day, when she asked if I could give her a massage. I apparently give very good massages, so I agreed.
She sprawled down on her bed, lying on her stomach, dressed in a black tang-top and her black panties. I was only in my boxers. I straddled her upper legs and began massaging her back. It wasn't long until I pulled her top up and massaged her bareback. I asked her if there's any specific spot she wanted me to concentrate on and she said lower back. So I moved my hand down, just above her panties and asked her if that was good. "Lower," she said, while wiggling her ass. Very cute. I got the hint.
I moved my hands further down her sides, sliding my fingers under the waistbands of her panties. I slowly pulled them off to the greeting of her beautiful round ass. I began by massaging her checks, tenderly and slowly. Kneading both mounds in my hands. As I was working her checks, I decided to spread them apart, only for a second, before continuing the massage. In that second I caught my first clear view of her beautiful little hole. It looked so cute nested in the middle of her ass like that. Even though I was horny as hell at this point, I didn't drive right for her asshole, in fear that I might frighten her off again. So I continued to massage her ass. But then I noticed how wet she was getting underneath. So as I continued to massage her ass with my right hand, while my left went down and stroked the outside of her pussy lips. I was amazing. She was soaking wet!
So I continued stroking her wet pussy and even begin fingering her as well. First with one finger, then two, curving them up and inside of her. She was clearly enjoying this, but I noticed that while doing this, she still would occasionally wiggle her cute ass in my direction. So I thought this time she might be ready.
I withdrew my index and middle finger from her wet pussy, and pushing her right cheek aside with my right hand, I began to trace around her asshole with my newly lubricated digits. Again she was very quiet during this, but I think she loosened up much quicker. "How does that feel?" I asked.
"Good," was all she said back. And that's all she needed to say. I could see her tight little asshole was relaxing as I touched and teased her opening. Finally I decided to enter her again. This time with a well lubed up finger. It was so tight, but I made sure to go slowly to not harm her. She moaned gently. So I pulled my finger gently out, and back in. Surprising she let me continue, and I continued to finger her ass, she got more and more into it, moaning and panting, letting me know she was enjoying herself.
And I was enjoying myself too! A lot! My cock was getting so hard, I needed to free it from my boxers. The sight was so hot, me behind my girlfriend while fingering her adorable, tight asshole, and knowing I was turning my girlfriend on with something she'd never tried before made me go crazy. I didn't even have to stroke my cock, I just ejaculated all over her ass without even trying. That never happened to me before. I began to apologize, but she seemed to understand, and was very happy seeing me cum like that.
That was the first time we experimented with anal pleasure, but it wasn't the last. We're not together anymore, but it still makes me hard thinking that I was the guy who got her into anal play.