The first time I met this guy was about a year and a half ago, and I've met with him on and off ever since.
One night while casually browsing the apps, I came across this 19 year old that was just a few miles down the road from me. From his profile, he was a big boy, 6'5, fairly built but seemingly a little awkward (think offensive lineman in football but leaner), SUPER hairy, masc, and listed himself as "curious but somewhat experienced top".
For context, I'm in my late 20s and fit, bi, and very masc/hairy. I tend to lean more towards my age range/build or the fit daddy type and I'm vers so I don't usually gravitate towards younger or his type but for whatever reason, I was intrigued so I fired over a message and a few pics.
Ended up chatting on and off with him for a bit. Super nice kid and we had actual conversations about sports and had fun just chatting. But, he said he was more into the fem, trans, smooth type and I am absolutely not that and wasn't interested in meeting for the most part.
Fast forward a week or so (I almost NEVER carry chats that long to be honest haha) and after talking about experiences, I get the idea he's trying to figure out what he wants or what he's about, but he's clearly a horny ass dude and sharing lots of pics and videos back and forth. Eventually, I just straight up ask him if he wants to come by for a bit and if nothing else I'll give him some head instead of jerking off all day long haha.
Few minutes later, he responds, "okay, where?" and I send him the address and a time and begin to get ready.
When he arrived, he was clearly very timid and nervous. It was kind of funny to me because even though I'm 6' and fit, this dude could easily pick me up and throw me across a room like a toddler and seemed really timid. But, I was sure to be really respectful and cool and let him work at his pace and not get into anything he's uncomfortable with. Honestly, I wasn't expecting much, but definitely wasn't expecting what happened next.
After a bit of touching, jerking, and body contact, I made a move and started to work his cock a bit with my mouth slowly. He has a great cock. Decent length, but really thick and wide and has some big balls. Fun to play with.
I was sure to be really enthusiastic about sucking it and working it with 110% effort…mainly because I was genuinely excited to have it in my mouth haha. But he was absolutely eating it up and moaning like crazy. From there, I got a little more adventurous working his balls, taint and eventually rimming his ass (apparently the first time and he loved it haha).
After a bit, he asks to play with my ass. Luckily, I was wearing a lubed up plug for fun because he pretty much immediately started double finger banging it and tried licking it a few times. Shortly after, he asks very respectfully in a wholesome way: "may I fuck you?" to which I reply absolutely! So I get into doggy, put a TON of lube in and he plops it right in. I had to get really upright because he was so damn tall so he didn't have to squat so far haha.
After about 5 minutes of pounding like a jackrabbit and hearing him moan like crazy he starts to finish and does this awkward move where he clearly started to cum inside and then tried to pull out and finished on my back. He started apologizing profusely for "almost cumming inside without asking" which was really wholesome and I told him I wanted him to haha. Full honesty, wasn't great but still enjoyable.
But, after he leans back and I notice he's still hard as a rock after a minute or two. I start playing and licking a bit and start to slowly start sucking to see how he reacts and I'm met with an immediate joyful "ahhh" as I put it in my mouth. He quickly asks for round two and I'm like yes PLEASE and I end up getting into a prone bone position.
He gets on top and goes back to business. This time he went a little slower and lasted about 10-12 mins and he was really hitting my prostate so it was extremely enjoyable. Feeling this behemoth of a dude wrapped on top of me and feeling all of his hair rubbing against me was hot as fuck.
After we take a quick break, go to the bathroom, and start chilling for 5-10 mins. I start talking about how much I enjoyed that (thinking he's about to leave) and then all of a sudden as I'm talking I see his cock twitching and swelling up. I said something like "damn man you've got some stamina" and he says "damn right I do" and he's clearly feeling very confident and into it which I love. He was about 2/3 hard so I start sucking again.
I'm not loose at this point, so I go full on blowjob mode and I haven't really had the chance to give him the full show. I start working it for a bit, getting sloppy with it, and about 10 minutes in again he finishes. I was impressed with how much cum came out because usually for round 3 for me I'm firing blanks but not him.
At this point, Im like "okay he's done" he came three times in an hour. But, he asks if he can top again so after I loosen back up I go to town. This time, I get missionary and eventually rotate to riding for the last 5 minutes he lasts about 20 minutes. Before I pull myself off he says with a direct tone "keep going" so I ride it for a bit and he cums AGAIN with absolutely no cool down in about 10 minutes and I'm mind blown.
After that night, as I mentioned, I've met him several times since and every time he cums at least three times and can do it with little to no break in between. One time, I wasn't ready to bottom since it was short notice but he said he hasn't got off in two days, so I ended up blowing him for an hour straight without stopping other than sucking his balls and rimming and he came 4 times shooting nice loads each time. Unfortunately, he moved away for school or i'd most certainly still be working him regularly.