gregboi

For me, one of the biggest turn-ons is discussing going bare with my partners beforehand, especially after we have been safe leading up to that point. The nerves, the thought of breaking that last barrier between us, making that mutual decision, the foreplay, those first few strokes, and of course that look on my partner's face when they take that first load, I love it! Unlike my condom-to-bareback experience, which was totally spur of the moment by my boyfriend at the time, one of my greatest experiences with going bare with a safe partner was with another boyfriend a few years later, who we will call Matty. Also, keep in mind that this was before PrEP was a thing, so there was a definite element of risk to this. By this time, Matty and I had been dating for about eight months, and we had been safe the whole time, respecting each other's limits; the sex was good, if a little routine, but we were happy. I'm a vers top, white, 5'10", thinner build, brown hair with blue eyes and twenty-six at the time, and Matty was twenty-three, primarily a bottom, also white, about 6'2", muscular, with black hair and grey eyes. We had not moved in together yet, and he was back living with his parents for a bit while finishing school, when I came over for dinner one evening. The rest of Matty's family was upstairs, chatting and hanging out after dinner, and we had gone down to Matty's room in the basement for a little before I headed home for the night. We talked a bit, and Matty playfully had rolled on top of me, looking down with those big grey eyes, bangs falling down to shade his face, and asked if I wanted to fuck as he started grinding on my cock through my pants. I had no intention of having sex with the whole extended family in the house, it was just too weird with his family upstairs, not to mention the chance of one of his many relatives walking in on us. I told Matty this, and he considered me for a moment or two, bent down to give me a peck on the lips, then rolled off me and agreed that having the family around was maybe not the best time to get laid. I also pointed out that we didn't have any condoms or lube, so even if we did screw, it would be bare and just with spit, unlike all the other times; when I said that, my heart did a flip at the thought of dumping a load in my boyfriend's ass, and despite my best efforts, ended up with a raging hard-on. My boyfriend made a little noise like he had just tasted something really good, then said that barebacking would be totally fine with him, but had to admit that without lube it wasn't going to happen, even if the family weren't there. We then talked about our sexual histories, when we had both last got tested (both negative), and decided that he would come over to my place the next afternoon, after I came home from work, and that we would go bare. A little while later, loaded down with leftovers from Matty's mom, I headed home, fighting a boner the whole drive. I made sure I had lots of lube, and even double checked that I had condoms in case Matty changed his mind and wanted to stay safe; the thought of getting to finally bareback my boyfriend was just such a massive turn-on, that I ended up cranking out a load before bed, even though I wanted to try and keep it all for the next night. The next afternoon, I got home, cleared the bed off, put out the lube, but kept the condoms in the bedside table drawer. I had just finished dimming the room when I got a text from Matty saying that he was just leaving home, and would be over shortly. I was buzzing with excitement the whole fifteen minutes or so it took for Matty to arrive, and I damn near sprinted to the intercom when he buzzed my code to get in. Finally, a knock at the door, and I let in my big lug of a boyfriend into the apartment, and after he took his shoes and jacket off, I pulled him in for a deep kiss, then led him to the bedroom. We decided to do it the way we usually did, taking our time, making things sensual with lots of making out, groping and dirty talk. Soon, Matty was down to a tight-fitting set of briefs, laying on his back, while I was totally naked, on my knees between his legs, as hard has I had ever been. I lay down over top Matty, my cock grinding against his through the briefs, our breath hot against each other's faces, his legs wrapping around me as we made out. "You want me to fuck you bareback?" I breathed, our foreheads pressed together, and all Matty could respond with was a breathy "Yeah." I gave him one more deep-tongue kiss before I kissed and licked my way down Matty's lightly haired chest, stopping briefly to run my tongue around the edge of his bellybutton, before hooking my fingers on the waistband of his briefs. Matty's good sized cock caught as I slid them down, then hit his stomach with a smack as I pushed his legs up to his chest to finish taking them off. Now we were both stark naked, rock hard, cocks oozing freely. Matty brought himself up onto his knees then wrapped me up in a bear hug while I groped his big, firm ass, our cocks pressed together, my head tilted back as Matty tried to stick his tongue down my throat. After a bit, Matty said he wanted to suck my cock before we actually fucked, so I stood beside the bed as he got down and easily deep-throated me, and it took all my self-control not to blast my load down his throat. For both of us, oral was fun, but it was never the main event, and it wasn’t sex unless it involved cocks in asses. I pulled back from the brink, reached down, and helped Matty up so he was sitting on the bed, and we could make out again for a bit. I asked Matty of he was ready, and he responded wordlessly with a nod and those big “fuck me” eyes, so I gently pushed him down onto his back, got onto the bed, and manoeuvred us both so I was again kneeling between his legs. Running my hands down his thick, hairy legs, I grabbed them by the knees and pushed them up to Matty’s chest, then kept pushing until his asshole was pointing straight at the ceiling. Matty’s hole was staring back at me as I pulled his cheeks as far apart as I could, then leaned in and softly traced the edge with my tongue. I kissed and licked my way to the middle, feeling Matty relax and sigh as I worked my tongue deeper inside him, then slipping a finger inside to stroke his spot, making my boyfriend gasp in pleasure. This was enough foreplay for Matty, as he quickly pulled my face from his ass, furiously made out with me, wrapping his legs and arms around me so there was no escape, even if I wanted to be let go. Wordlessly, I reached over for the lube as Matty let go of me and pulled his legs back to show his vulnerable pink hole while I covered my bare cock with as much lube as I could before closing the bottle with a snap. I lined my raw cock up with his pouting anus, and pressed, Matty easily letting me inside before stopping at his second hole for a moment; I looked deep into his big grey eyes as I saw my boyfriend take a breath, hold it, then allowed me all the way inside of him. That wonderful, velvety texture I had missed so much from my previous boyfriend, was there inside my man, and I quickly found Matty’s spot with my cock as he let out a gasp of pleasure. Matty pulled me in for another hug, wrapping his legs around me as I hooked my arms under his shoulders, gently rocking us back and forth as we kissed deeply. The thought of my leaking cock, deep inside his ass, our moist, delicate tissues rubbing against each other, my fluids leaking into his vulnerable guts, my cock stewing in his juices, sharing absolutely everything. It still gets me rock hard to this day! I don’t know how long we stayed like that, but eventually I picked up the pace, sliding in and out of Matty’s hole as he whispered encouragement. When I told Matty I was going to cum, he pulled me tight as I pushed as far inside of him as I could, cumming hard enough for his eyes to go wide and let out a “fuck yeah!” as I did my best to het him pregnant. My chest still heaving, I thought we might take a break, but Matty had other ideas. Still holding me tight with my hard cock inside of him, Matty rolled us over so I was pinned to the bed, then leaned back and rode me mercilessly as he tugged out a huge load, coating my chest in sticky white ropes as his ass rhythmically gripped my poor cock as it marinated in our mixed juices inside of him. When it was all over, and Matty eased himself off me, we lay side by side wordlessly for some time until we went to the shower together to clean up. I want to say we went for round two later on, but the truth is that we were both totally exhausted floating on one hell of a post sex high, and I’m pretty sure Matty kept my load in him for as long as he could. After that, it was no more condoms for us, and once we moved in together most nights ended with my load in Matty’s ass. With a little gentle persuasion, I was able to convince him to be the first guy to top me bare, and I was instantly in love with the feeling of sexy vulnerability as he squirted inside me; even with that experience, I’m still mainly a top, and happy to be one. Matty and I stayed together until he had to move for his career a couple of years later, while I had to stay put for mine, but this remains as one of my greatest sexual experiences.

So damn hot!

Shameless bump!

That was incredible! Thanks Voyeur94!

Thank you Voyeur94, this was worth the wait!

Shameless bump, but Voyeur94 this is a fantastic story, please finish it!

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.

So hot! I hope you pick this story up again!