It was late June 2020. I was 23-years-old, living by myself. Ever since I had come out as bisexual in March, I had been exploring the darker side of Snapchat. I was cruising the relevant Reddit pages like DirtySnapchat and GaySnapchat, but also various R4R pages. I’m not sure if I reached out to him or if he reached out to me, but in one way or another I met Joshua. I think I had reached out to him because he was advertising on an R4R page that he lived in the same city as me. We began talking and I found out that he was only a year or two older than me living a short drive away. We chatted for a bit, and at some point in the conversation I mentioned that I was in the middle of binge-watching *Legend of Korra*. He says that he makes an effort to watch *Legend of Korra* in its entirely once a year, and we bring up the possibility of having a little *Korra* date. So, eventually we set everything up for something during the upcoming week. At this point, we’ve seen each other’s faces (and other body parts), so I know what to expect. He arrived in the late afternoon. He sat on the couch, I made some tea, which he kindly refused, and we got to talking. We talked about ourselves, what we like to do, random things like that. We were staying a little distant from each other, I noticed. But I got *Korra* set up (I was in the middle of season 2 at the time), and we both, rather naturally and instinctually, curled up with each other, alternating with one of our heads on the other’s shoulder. We watched three episodes.
At the end of the third episode, I didn’t immediately reach out to my computer to skip to the next episode like I had typically done. We stayed in that position for a few minutes, with my head on his shoulder. Joshua was a little heavier than me, so he served as a great cuddle buddy. But (one thing about me), any intimate human contact will almost immediately get me hard. So the thought entered my mind of whether I should make a move. Pretty soon our hands were touching, playing with each other’s fingers in a kind of interesting, flirtatious dance. Then in a moment of bravery that I rarely display, I grabbed his hand that I had been playing with and I placed it directly on my erection through my shorts. He gave a little chuckle and a little squeeze. He said something in response, but I can’t remember what he said. All I remember is that we began making out shortly after. It was the first time I had kissed a man (outside the context of a dare). He opened his mouth wide when he kissed me, so it was a little sloppy, which I didn’t mind. He was also unshaven, with a little bit of visible stubble making his cheeks a little rough. We kissed, and we were getting a little handsy. I had my hand on his thigh, working my way towards his crotch. His hand was already on my crotch (you know, since I had placed it there). We took each others’ shorts off, which led to taking our underwear off. Our cocks were both average, around the same size. But I’m circumcised while he was not. I had always been a little weirded out by uncircumcised cocks, mostly because of aesthetics, but also because of health reasons. I had been taught that uncircumcised men were more likely to contract diseases (at least, if they weren’t hygienic). But, of course, I wasn’t thinking about that. All I was thinking about was this boy, the first man with whom I ever had a genuine sexual experience, with his cock out right in front of me. I grabbed it as he grabbed mine. We stroked each other a little clumsily, but then he pushed me back and leaned over and wrapped his mouth around me. It had been years since I had a proper blowjob, so this was heavenly to me. I tried to continue stroking him, but I couldn’t concentrate. It just felt so good.
He stopped after a couple of minutes. We kissed for a few seconds, and then he asked, “Have you ever thought about sucking a dick?” I had been anticipating this question, hoping it wouldn’t come up. I had only come out as bisexual a few months before, and cocks were a little scary at the time. After stumbling over my words a little bit, I just took a deep breath, leaned over, and tried as best I could to take as much of him into my mouth as possible. I began to suck his cock, and it wasn’t as bad as I thought it would be. It was like sucking on a big, thick, soft finger. Plus, I was finally realizing the benefits of the uncut cock. I realized that the uncut foreskin acts as a bit of a built-in pocket-pussy. It’s a sleeve that aids with jerking off, and I was a little amazed that I hadn’t realized it before. We continued this cycle for some time. At one point, he said something about one of his goals of giving straight, bicurious, and bisexual men the best head they’ve ever gotten so they would never go back to girls again. I must admit, it was the best head I’d ever gotten at the time. This went on for some time. At one point, he straddled me and continued kissing me. I grabbed his enormous ass and squeezed.
After a few minutes, I asked if he felt a bit crammed. He said yes, so he got off me. Then, in a move that part of me regrets, I grabbed his cock as if it were a dog’s leash and led him to my bedroom. We laid on my bed and continued the cycle of sucking and stroking and kissing. At one point, my face was directly between his legs. I was sucking and jerking his cock, while the other hand did a bit of exploring. I started to circle his hole with the tip of my finger. He didn’t react, so I started pressing harder. Still no reaction. A little annoyed, I looked him right in the eye, plunged my finger into my mouth to lube it up a bit, and then slowly pushed it into his ass. He exhaled with a big grin on his face. But once I started wriggling about inside him, he started to breathe heavily. Then that heavy breathing turned to moaning. I fingered him and sucked his cock at the same time. He started to moan louder. I alternated between sucking and stroking, but keeping my finger in him all throughout. When I took my finger out, he grabbed me by the wrist and said, with a grin spread across his face, “You have to realize, I never moan when I finger myself… you’re really good.” I smiled, hoping that he was being genuine and not trying to make me feel better about my lack of experience. We flipped over so he was on top of me. We continued to kiss, and he continued telling me that I’m cute (again, not sure if that was genuine or just compensating flattery). He began to grind on me a little bit, making sure that his asscheeks were keeping my cock hard. He looked over at my bedside table and spotted my lube. He grabbed it and, after briefly chastising me on my brand choice, made sure my cock and his ass were thoroughly lubricated. He sat down on me, and I felt the tight warmth of the first ass I’d ever been in. I smiled, but I was also shaking nervously. He rode me slowly for a few minutes before getting off and getting on all fours. I entered him again and fucked him doggystyle, with the only noise being the sound of our thighs slapping against each other, as well as the occasional moan. But I kept sliding out of him and had to awkwardly find his hole again. Eventually he flipped himself over again and pulled me onto him. But at this point, my worst fears had come true. I was so nervous I was growing soft. I tried to get myself hard again and squeeze myself back into him, but it was no use. I gave up and plopped myself right next to him.
Both of us were disappointed to say the least. I said I was sorry, and he tried telling me it was alright, but after a few minutes of laying there, he got up to put his pants back on. It was dark at this point. I made myself a drink and we chatted for a few minutes more before he decided it was time to leave. I reflected on what had just happened. Over the course of a couple hours, I had kissed a guy for the first time, had a cock in my mouth for the first time, fucked a guy’s ass for the first time, and probably a few other things I’ve left out or forgotten. We gave each other a hug as he left. He blocked me the next day.
Source: reddit.com/r/gonewildstories/comments/l4mm69/a_day_of_firsts_mm