Memorable Grindr Encounters

The Time I Hooked Up with a Teacher

One of my best regulars for a while was this guy who I'll call Ron (not his real name). He was one of the first people to ever hit me up on Grindr, but ended up being like only the fifth guy or so I met from the app. He was around 35 years old, so a middle aged man. If it wasn't made obvious from the first chapter, I've always been into older men. Most of these encounters were from when I was about nineteen or twenty and just starting to find my sexual liberation.

I ended up planning to meet him at some point in our conversations on the app when he offered to host in his apartment. I ended up finding out that he lived on the other side of my old street about ten minutes away from where I was loving at the time, which was a pleasant surprise. In a way he was my "neighbor", though I'd never seen him around before.

So as usual I was specifically in the mood to suck someone off so I offered to meet him for a blowjob, which he agreed to. So I went off to meet him in his place. When I arrived I used the intercom to let him know I arrived and he had the door unlocked for me to meet him on the third floor, where he lived. I went up the stairs and knocked, and he answered the door to meet me and invite me in.

So Ron was quite a big guy, a little taller than me (I'm pretty tall myself), and obviously had a much bulkier frame. He was on the chubbier side (but in a kind of dad bod sort of way), but he had big strong hands and a cute stubble. I also recall his very big, luscious lips.He led me to his room, lay on the bed and I followed along, and got right down to business. Talk about a horny guy. We started kissing immediately and feeling each other under our shirts. Before long he was pulling out his cock and directing my hands to it.

Like most things about him, Ron's cock was very big. I'd argue it's the biggest cock I've ever taken. The good news was that Ron was a very patient lover so he'd let me explore him to my heart's content while he laid back and enjoyed himself. I lay myself between his legs and thoroughly savored it. I would suckle and kiss, occasionally lick across the shaft, and do my very best to get the whole thing in my throat. I knew I was doing a good job from his slight hip bucking and heavy breathing. All the while I would fondle his balls and play with his nipples, spreading my attention across his body. Occasionally I'd lift myself to suck on his chest and french kiss his lips. I really liked his patient enjoyment of it all. I guess he saw that I was pretty young and excited and wanted to see what I was hungry for.

Now the unexpected part of this hookup was the eventual interest he took in my body as well, which slowly led to him lying over me and rubbing his cock against my ass. I was a little hesitant but he assured me he wasn't going to put it in. At this point though I admit that I was just the right amount of turned on to consider a change of plans and letting him fuck me, so I asked him if he happens to have protection. He replied "yup, always," which was a pretty reassuring response (there are a lot of guys, in my experience, that will happily try and dodge using protection any chance they get), so I told him he could get it if he wanted.Before I knew it, Ron was wrapping a condom over his hard-on and coating it in a little lube. I was lying belly down and he got on top of me. Very carefully adjusting himself so his cock was aligned with my hole, he slowly began pushing into me. I'm a little squeamish so the first entry is always kind of a struggle for me, but before I knew it, he has slipped in completely. I remember distinctly thinking to myself how I expected him to take forever to get the whole thing in, but to my surprise I was able to take his entire length pretty easily despite his size.

Ron began thrusting very slowly in and out, giving me time to adjust to his cock. Despite that initial struggle, I was in heaven. His arms held up his upper body over me as he gyrated his hips to push his cock in and out. Considering how big and burly he was compared to my scrawny self, I'll bet he was delighted by how tight my hole was.

He was pretty soft spoken and not a very verbal top, so we fucked rather quietly, save a little moaning and huffing here and there, and the occasional whisper of the word "safado" (which basically means "horny boy" in Portuguese) in my ear while he fucked me. Dude could fuck all right, but he didn't last very long. Kinda out of nowhere, he let me know he came as he carefully collapsed onto me for a while to catch his breath (which I thought was both adorable and hot). He slipped out of me and yanked off his condom, threw it away and lay down next to me.What happened next was unexpected, as we lay and cuddled for a while, we began talking, and I realized just how friendly Ron was. Even though he was soft spoken, much like me he was quite the chatterbox, and we actually had a lot in common, which surprised me.

Firstly, he was very into art, which is always a plus in my book. Secondly, he was a teacher! This might not have been relevant to me at the time the same way it is now, but as someone who's studying to be an art teacher myself, it was really nice to have had that interaction with someone with similar interests to mine. Also I giggled to myself about the bragging rights I now had for fucking a teacher. We spent nearly two hours chatting about all sorts of stuff from the kind of art we liked to make, to his experiences as a teacher, to our tastes in movies (my guy has a great taste in movies).

He was also very open about his experiences as a gay man, which might sound like a given considering the hookup and all, but lemme tell ya. I'm from a little town in Brazil, a lot of Grindr guys are closeted or curious straight men who prefer not to think too much about their sexuality, and if they do there's always a layer of complicated feelings about it. And at this time I had barely any queer people around to interact with, so it was really refreshing to speak to someone so openly about our lives as queer men and such. He even sent me an ebook he was reading about pride later (though I confess I didn't get around to reading it).

In any case, Ron turned out being a really easy person to talk to, and I found myself lying around naked and lost in conversation with him. So much time had passed in fact that at some point we became aware of how naked we were and began to get horny again. So before I knew it, I was back between his legs and sucking on his now hardening cock. I feasted on his cock for about ten minutes or so before he began climaxing, and I took his second load in my mouth.

Ron ended up being a regular of mine for a while. We met up about three more times after that, though I believe we never fucked like we did the first time. Most of our encounters followed a similar routine of me meeting him in his place, us getting right to it, him finishing in my mouth, us hanging out for a few hours and chatting, and then me sucking him off a second time.

The most memorable encounter after that first one was the time when our round 2 got extra spicy as we were trying all sorts of weird and different positions. He lay my head against the wall and knelt over my chest, fucking my mouth while I rocked his hips with my hands. He began turning me on so much I couldn't keep my hands off my cock, so at some point he sat over my chest and stroked himself while staring deep into my eyes. With one hand stroking my own cock, I grabbed his cock with my other and began jerking us both off together. This set him off and he came all over my chest. He lay next to me, and seeing how I was close but not quite there, he inched really close to me and started feeling me up with his hands, touching my upper body while I tugged on my dick. He was driving me crazy, I couldn't keep my moans to myself. Eventually I reached my limit, and began shooting ropes of cum onto my chest, adding to his. By the end I was absolutely glazed in cum, and he laughed and called me "safado" again. It was easily one of the most intense sexual experiences I've ever had.

I eventually started drifting off Grindr and took sort of a "hiatus" for a while. When I eventually did get back onto Grindr, Ron was still around, but he had unfortunately moved to the next town over. He still was down to meet me at some point, but I never got around to visiting him in his new place. Depending on how things go down I might end up meeting him again sometime.