u/Ok-Umpire774

My fist time all the way

This was a long time ago but was my first time. Everyone in story is at least 18.
So I guess I should preface that I have known I was bi from pretty early on. This takes place in a small conservative southern town in the 80s so you could imagine what I would have faced if my family found out I loved cock. 😁
By the time of this story I had sucked off every guy in my friend group in my neighborhood. Several brothers and even one of the dads. Variety of sizes from tiny to OMG. But no one wanted to fuck me. I guessed getting sucked off by a guy was fine but fucking one crossed a line. 🫤
One of our older friends we will call Brian was home for break from college. I had heard he had gotten caught balls deep with another guy from school so figured he would be my ace in the hole so to speak if I could get him alone. I was 18 Brian was 24 he was built like an NFL linebacker and about 6’2” I would describe myself then as a heavy metal twink. 6’ about 140 long hair. I played guitar in a band so I did ok with girls too.
We had been playing basketball with the guys most of the day we wound up back in my parents basement den playing video games. We decided Brian would stay over. We pulled out the bed in the couch and made it up. I told him I liked to sleep naked but would keep on underwear if it weirded him out. He said that it was ok with him(score) We got in bed but he still had boxers on he said he liked to cuddle but it wasn’t gay. I said cool and as he scooted in to spoon me I arched my back so I could rub my ass on his cock. I felt him getting hard but he still didn’t make a move. We fell asleep spooning. I woke up at about 2:30 and I was kinda on my knees straddling him I was suprised and looked back he said I had rolled over him and he was holding me. I grinned and dropped my naked ass down on his cock and grinded him. I slid off and told him we can’t fuck while everyone is home but I would suck him off if he could be quiet. He agreed and I pulled down his boxers. His cock was so nice about 6.5” cut, thick but not too thick and neatly trimmed pubes a rarity in the 80s land of the huge bush. I held him stroked him a few times and then gave him the best head I knew how to give. It must have been nice because it took him about 5minutes before he unloaded in my mouth. We spooned again and fell asleep.
I woke up about 7:30 hearing my mom and dad getting ready for work. Once they were gone I told Brian let’s go up to my room. Once there he said he wanted to shower and while he did that I found some vasoline and started rubbing and fingering my hole. I heard the shower turn off so I got up on all fours, arched my back and placed the vasoline beside me. Brian came out of the shower and said ohh that looks nice. He came over and I thought would just stick it in but instead he got down and started eating my ass. I must say to this day that is one of my favorite things. He ate my ass, fingered my hole and stroked my cock until I was literally begging him to fuck me. I guess while he was doing this he had been lubing his cock up so he stood up and pushed the head in. OMG it hurt like hell I thought he was going to tear me in half. He asked if I was ok and all I could do was grunt yeah. He slowly kept pushing in I was biting the pillow to keep from screaming and trying to breath through it before long I felt his balls against my taint and knew it was all in. He just held it there for awhile until I started to loosen up. He slowly started fucking me with short deep strokes, slowly pulling out further each time until he was pulling all the way out and going all the way back in. I still love the feeling of a cock right when it crosses the threshold. It took a bit but before long he was just railing on me. He flipped me over into missionary and put a pillow under my ass and slid back in. Now while he was fucking me he was holding my hard as a rock cock and stroking me. He grabbed my hips and went back to railing. In this position he was really hitting my spot and before long I came shooting long ropes between us. I could feel my ass clenching and griping his cock in my orgasm. I swear I could feel every vein and bump on his cock. I guess that was too much and sent him over the edge he went balls deep grabbed my ass cheeks and unloaded a massive load deep in me. We laid on the bed for awhile in post sex bliss. Then got up showered and went and hung out with the guys like nothing happened. We had a few more sessions before someone at my dad’s work told him about Brian getting caught fucking the other guy and forbid him to come around anymore. If he only knew. Sorry so long but this is a pretty vivid memory for me.

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u/Ok-Umpire774 — 9 days ago