Back in the late 2000s, I had been talking with this guy online for months, and we had finally decided to meet up one afternoon. Just like online, we really hit it off in person, and found each other attractive - I was in my early 20s, about 5'10" and 150 lbs, with brown hair in a crew cut, blue eyes, and he was around 20 or so, 6'1" and about 180 lbs, with shaggy blonde hair and blue eyes. I met him at a nearby bus terminal, and we went for a walk for a bit and got a coffee, and things were going great.
We ended up heading back to my place, and after chatting for a while longer, he started playing footsie with me, then we stood up, and I did my best to shove my tongue down his throat, while he pulled me tight into him. We started pulling each other's clothes off until we stood there naked, my hard cock pressed up against his, precum oozing all over, his big hands running up and down my back as I groped his wonderfully squishy ass. I backed up over to my bed, and pulled him down on top of me, and we kept at it, making out hard, grinding our cocks while I started fingering his ass.
He then slid down while I lay back, and he started sucking my cock, and I enjoyed watching his shaggy mop work up and down for awhile before I pulled him back up on top of me, and we started making out again. We rolled over, and this time, I went down and sucked him as deeply as I could, his hands holding me against his cock until I had to come up for air, the scent of his cock driving me wild. I all but leapt back up on top of him, our cocks mashed together all slippery from the blowjobs and precum as we made out again, and he asked me to fuck him.
I reached over to the bedside table and pulled out the lube and a condom packet, which tore open and rolled the rubber down my shaft as he popped open the lube and started on his hole. He rolled on his back and pulled his legs back to show me his hot, pouting, lube-slicked hole, while I put even more lube on my rubbered up cock, after which I knelt down, and lined up with his ass. My cock pressed against his asshole, and after a moment of resistance, I slowly slid into him until my pubes were grinding against his ass as I pinned his legs to his chest, and started fucking him gently at first then picked up the speed as we both started really getting into it.
Eventually, we ended up with me on my back and him riding me cowgirl as his cock kept leaking like a faucet as I nailed his prostate, making him whimper and bite his lip. I pulled him down to start making out again as I fucked him slowly from below for a bit, then slid out of his ass. My little apartment was really hot, and we were both covered in sweat from the heat and from fucking for the better part of an hour. Thinking that we should give his ass a break for a bit, I pulled the condom off so we could go back to oral for a bit, however he had other ideas.
He pushed me down on the bed with a hand on my chest, straddling me, and gave me a look I'll never forget as his other hand guided my now bare cock back inside of him. I'd fucked plenty before, but never bareback, and the difference was unreal; the heat of his ass, all the lube and the velvety texture of his insides were almost too much to take. He gently worked my raw cock with his ass, squeezing and flexing on me as he jerked his own drooling member, sighing as I angled again to hit his spot. I wanted it to go on forever, but all good things must come to an end, and I could feel my impending orgasm, and I asked him where he wanted me to cum. His response was to clamp down on my dick as he leaned in for a kiss then told me to cum inside him, so I grabbed his hips and slammed upwards a few more times before I blew my first ever bare load inside a guy, breeding him deeply. This pushed him over the edge too, and he came all over my chest a few moments later, and I rode the wave of his hole clenching in time with his orgasm.
In the afterglow, we went to get cleaned up together in the shower, and talked some more about what had just happened. I told him that was my first time bareback, and he admitted it was his first as well. He said he had no intention of going bare our first time, let alone fucking on what was technically our first date, but the idea of me breeding him just sort of popped in his head when I pulled the condom off. We laughed about the whole thing, and ended up screwing again a couple of more times that day and into the evening, each time ending with another of my loads in his ass.
We ended up dating for awhile after that, and even though we discussed our histories of safe sex, got tested just to be sure, which came back negative for both of us. After a few months of being together, things just didn't work out, and we ended it as amicably as possible. From that point on, I was hooked on barebacking, but without that trusted, exclusive partner, it was back to being safe for me until I was well into my next real relationship, and we talked about it at length and got tested before finally ditching the condoms for good.
