I've known my fuck buddy James for years. We met at a party I had at my downtown apartment. We hit it off, and he ended up being the last one at the party. We were talking in the kitchen as it was the farthest room from the bedroom where my boyfriend had gone to sleep. James and I were both leaning against the counter when we reached the inevitable lull in the conversation. At the same time we both leaned in and started kissing. He's a short Hispanic dude, wiry but muscular frame, and you'd think he was a total bottom just by looking at him, but I found out he was actually a total top. We kissed for a few minutes and he started groping my ass so I grabbed his cock through his trousers. He was huge. Right about 8 inches and girthy, with a wide bulbous head. Holy fuck I thought to myself, I need to get fucked by this cock.

Alas, it wasn't to be that night, but James did turn me around up against the cabinets, sliding my trousers and underwear down just below my ass. While he stroked my cock, his slid up and down my ass crack, every once in a while he'd let the wide head push up against my hole, but he wouldn't go inside. It felt so big it seemed like it would never fit. He ended up just dry-humping my crack until he shot his load over my back and I shot mine on the countertop.

We kept in touch for the next couple years, and the first time he fucked me was about 6 months after my breakup. He insisted on wearing a condom, which I was kind of bummed out about, but still totally cool with. I respect people's choices in that area. It took a while to take his cock at first and it felt like he was splitting me open, but eventually I got used to it and the sex was always good. Usually he'd pull out, take the condom off and cum on me. We hooked up a couple of times a year for years, him always using a condom.

Then a couple years ago I was sitting on top of him with his massive condom covered cock buried in my ass and we were chatting a bit while I got used to his cock splitting me open. He asked me if I had any kinks and I told him not really. I mean I like fucking while wearing only sneakers, and I love wearing a jock strap while bottoming, but I don't really consider those kinks. Then I mentioned that I really like getting fucked bareback and having a guy cum in me, but can never really find the right guy I want to do it. Suddenly he lifted me off his cock and rolled me onto my back. I watched as he pulled the condom off his cock and he went up between my legs, and for the first time, I watched his massive cock sink bareback into my hole.

I didn't think it was possible but my cock got even harder and I started furiously masturbating as his muscular ass drove his bare cock in and out of my hole. This went on only for a couple minutes until he told me he wouldn't last long fucking me bareback. I told him I didn't care as long as he shot his load inside me. About 20 seconds later he let out a moan and told me he was cumming. As he was thrusting his load deep in my ass my own load started spewing so hard it hit me in my face. He laughed in shock and licked a bit off my face as his cock kept slowly moving back and forth in my cummy hole.

Finally he pulled out and his cum spilled out of my gaping hole. I left satisfied. The next time we had sex was memorable as well. I was on my hands and knees wearing only a jock strap as he ate out my hole. Then with no talk of condoms, he just lubed up his cock and sank it bare into my hole and fucked another load into me. We haven't used condoms since.