This is a memory that popped up today when I was looking at porn at work. If you enjoy it, drop a buck over to the guys at Nifty for keeping us all dripping in our shorts, okay?
Years ago, I had this boyfriend that was totally sexy but very inhibited. He seemed shy about being naked in front of me even though I found his lean body and meaty cock totally addictive. We always played safe together, usually just blowjobs, but since he was not versatile, I let him fuck me a few times with a condom.
One night we were up late drinking and I stayed over at his apartment. The next morning, I remember slowly waking up with him hugging me from behind. I could feel his meat pushed up against my ass. He started gently pushing and grinding his cock against my ass, but I pretended to be still asleep. I think I wanted to see how far he would take it.
After a few minutes, he started slowly working the back of my boxers down, exposing my ass. Then he pulled away for a second, turns out he was pulling his cock out of the fly of his y-fronts. I was lying on my left side, and he pulled up on my right ass cheek with one hand to open up my crack, and lay his cock right in there. He started sliding it up and down my crack, then pushing the head of his cock right up against my hole. After a while, his precum had my pretty well slicked up, and his head started nudging, nudging, nudging into my hole a tiny bit at a time. Then when he had about an inch of his cock in my hole, he gave a good shove and the whole head of his cock just popped in. I heard him gasp and he held still for several seconds, I think to keep himself from coming. Then he started gently fucking into me really slowly. I couldn't believe it was happening. We had never barebacked before or even talked about it. I was too hot to stop him though, and just kind of groaned as he pushed more and more into me. He was only about two inches in (which isn't bad given that he wasn't using any lube) when suddenly he stopped, and I could feel his cock pulsing in my hole. Then I could feel the wetness of his come pushing out around his cock and sliding down my ass onto the sheets. It was a huge load! I was so horned up from him coming in me that I just pulled twice on my cock and came all over the place.
After he caught his breath, he got up and got a towel, cleaned me up and pulled up my boxers, then got in the shower. He never said a word during the whole thing, and we never talked about it afterward either.
All that morning, I walked around with a semi hardon, feeling the remnants of his come in my ass, squishing around as I walked. I felt like anyone that saw me could tell I had just been fucked in the ass and used as a cum dump. It made me so hot. I was hoping he was going to start fucking me raw from then on, but strangely he didn't. He did start being more aggressive about blowing me, however. So, I guess you win some, you lose some.