Howdy! So the person I've had sex with the most, regardless of gender, is my best friend. We have been friends since a month after he moved to our small town actually 10 years ago now. We pretty much immediately clicked as we bonded over video games, and he easily meshed into my friend group who would play Black Ops 2 wayyy too much for the time. What was special about him wasn't just the shared interest or similar social activity, but it was how easily we shared personal, emotional things with each other. Little would I know, this one connection would lead to a type of friendship I couldn't ever imagine.
So first, a little background about what we look like. I'm Matt; 5'10", very average build, though I've got somewhat broad shoulders. I have thick, dark brown, curly hair with matching dark brown eyes. I'm clean shaven. Let's call him David. He's about 5'6" tall, stocky, and barrel-chested with a light stubble throughout his face. His hair is cut short, almost high and tight.
Then, some context into how this all started: So you could say I was pretty "lame" in high school. I didn't have a ton of friends, didn't go to parties, wasn't involved in sports; heck I didn't even get drunk until a family gathering shortly before graduation. Instead, if I was with a friend, I would go to their house or the would come to mine (more regular) and we would just eat junk food, play video games, and just crash on the other's couch. Those memories defined my adolescence to early adulthood, and little would I know it, this exact arrangement would be what led to David and me uncovering some unrealized sexual preferences.
So there we were one such night, November of senior year (2019). I was 18 and he was 19 (despite his intelligence, he was held back a year in pre-k). It was late, pushing midnight, everyone in my family was asleep and we were in my unfinished basement, each laying on a separate couch. We've had lots of late nights talking like this, usually it's the latest and greatest with Call of Duty, or we were talking about school, maybe some upcoming plans with friends. Occasionally, the conversations would turn to more personal matters; girls, problems at home if there were any, and occasionally which teachers we had found the most attractive. These sexual conversations were a little more common than I'd like to admit (hell, we were teenage boys who didn't get enough action lol).
One such night, we were talking about which teachers we thought were hot, and who we would want to have a threesome with. I said I would want one with two of the science teachers at our school. They were hot and blonde, and I said I'd want one to sit on my face while the other rides me. He said he'd take the second of those science teachers and one of the art teachers, saying he'd love to fuck one in doggy while she ate the other out. After his decision, I said, "Maybe we should have a threesome with the second science teacher together," laughing after I said it. He agreed. We talked for a little while longer, joking; but I can't lie. That conversation really turned me on tonight and I was already hard as a rock. I don't even know how we got to it, but the conversation shifted to talking about porn.
At this moment, I found out that we both watched porn more than I thought we did. We started talking about our favorite categories. I spoke up first about it, saying that, "My favorite categories are probably lesbian and cumshots. I love hot girls fuck and the cumshot is my favorite part of a video with a guy in it." David told me that he respected my choice, but his taste was a little different. He said, "I guess lesbian is alright, but I prefer things with penetration. I really like fat-asses and anal. Anal penetration really turns me on, it's why Remy LaCroix is my favorite pornstar."
Me: "I've never heard of Remy LaCroix before. Is she good?"
David: "She's the best. Look her up dude she has such a fat ass."
And so I proceed to look her up and one of the first images was her face in ecstasy taking a huge dick in her ass. "Damn, she is nice. Want to know my favorite?"
"Sure man."
"Kennedy Leigh. Beautiful blonde I love her. She gives great head and her cumshots are always so hot." He proceeded to look her up and, while Remy was still his favorite, he liked what he was seeing. After that a moment of silence passed before David spoke up.
"Hey man, totally cool if you say no, but I'm actually kinda horny, is it okay if I jerk off? You can, too." I was taken aback by his question but also excited at the thought of getting off with my best friend.
"Sure man, I'll jerk off too." So there we were, two best friends in the dark, in separate couches. The sound of the blankets ruffling as we took off our pants and the nervous, heavy breathing of two virgins excited to get some action; albeit not the action we expected to have. In the pitch black, some light came on as the two of us found videos to watch. He found his video first. I immediately heard moaning and a guy groaning.
"Whatcha watching David?"
"I found a Kennedy Leigh cumshot compilation. Figured I'd try it. I like it. You?"
"Nice dude. Haven't found mine yet, but I think I'm gonna watch some Remy anal."
He chuckled. "Good choice man."
And then there were three sounds in night. The shifting of blankets as we jerked off, the quiet sounds of pornography, and our soft moans as we shared our moment of pleasure. David was the one who came first who had a small grunt and then came, wiped himself down with tissues, and told me he had finished. I wasn't done yet but was close. "Is it alright if I finish, David?"
"Of course bro." So I did, with a small grunt I came watching Remt LaCroix take a huge cock in her ass. We didn't say anything for the rest of the night other than, "That was fun, goodnight dude."
That was the first experience we had had with each other, but I'm so fucking happy to say that it wasn't the last. We'd go on like that for a while. Separate couches, Separate videos, but jerking off at the same time. I had never even seen the guy's dick before but we've came together so much already. It wouldn't be until spring break of that year, just before all of the COVID lockdowns hit, that we would take our friendship to the next level.
I'm sorry if this post isn't quite "gay" enough (the story will get like that later). But if you enjoyed let me know! If you have questions I'll answer them as best I can!