First and last time with an older man
my first and only time with a man
First and only time with a guy
I’ve(22m) never shared this story with anyone, not even my current gf who’d probably like it. It’s my first time posting, but I think it belongs here. It’s a long story, tldr at the end.
This happened about four years ago. I’ve always consider myself straight, but around that time I had just gotten out of a long term relationship that I was in since high school and was very lonely and very horny. I started jacking off on Omegle and getting real turned on by watching other guys jack off. Never thought I’d be into that, but seeing another cock cum because of me was a huge turn on.
After awhile doing it online wasn’t enough so I decided to do it irl. I was young and had never done anything like this so I turned to the internet, found the m4m on Craigslist and started browsing. I didn’t want sexual or anything, just wanted to watch someone else jack off.
I responded to what seemed like a hundred posts, not one wanted a first timer, or they always wanted to have sex and no one wanted someone with a small cock.
Finally I found a post with someone looking for a bate buddy(had to look up what that was) I responded and told him it was my first time and that I was young, chubby and had a small cock. He was into it, asked for a pic and loved my hairless body(I used to shave my entire body back them). He was 55, fit, married, and in town on business. He had a room at a hotel downtown and wanted someone to come over and jackoff with him while watching porn.
It seemed too good to be true, I told him how nervous I was, but he was very nice and reassured me that he would be respectful and wouldn’t do anything I didn’t want.
So I go to the hotel and my heart is racing. As I’m going up the elevator I start to second guess myself, but then I reach the floor the doors open and I decide to just do it. I walk to the room and knock, my heart is beating even faster. He answers in a robe and invites me in. We say hi and talk a bit, but all I can think about is what he has underneath. He offers me some weed to smoke, I do. I can’t take my eyes off this crotch, his robe open just a bit and I see it. He notices and pulls it open a bit more revealing a huge cock, not the biggest I’ve ever seen, but way bigger than mine. At first it hangs, but then it starts to get hard, he starts to touch it slowly stroking it. He asks if I want to join him, by this time I’m rock hard. I begin to undo my pants, he tells me to get completely naked so I do. Then he tells me to just stand there in front of him naked, he’s still stroking. He tells me to turn around and show him my asshole. This wasn’t exactly what I wanted to do, but I’m so turned on I do what he says and spread my cheeks. He asks if he can rim my asshole, but I tell him no.
He tells me to come sit down and to touch myself. As I do he turns on the tv and orders a porn, I don’t remember what it was, I never even looked at the tv, all I could do was stare at his cock. I’m like 4 inches on a good day, he had to have been twice the size as me. We stroke ourselves for a bit, he tells me he’s never seen an uncircumcised cock before and asks to touch it. I let him, he pulls the skin back and then over the head again. He’s fascinated with it, he keeps moving the skin and eventually is just jacking me off. I ask to touch his cock and he lets me. Its nice and girthy, couldn’t even close my entire hand around it. We play with each other for a bit, then he tells me to stand up again and jack off for him, I do. He tells me he’s about to cum and then shoots a couple thick ropes onto the carpet. Seeing him cum gets me going and I tell him I’m about to cum, but he tells me to stop so I do. He gets on his hands and knees, crawls over and takes my cock in his mouth and starts to suck me off. I’ve gotten blowjobs before, from my ex and a couple other girls, but this is definitely the best blowjob I’d ever received. I don’t last very long and within a minute I’m about to blow. I tell him and try to pull away, but he grabs my ass and deepthroats me(which isn’t too hard lol) I don’t think I’ve ever cum as hard as I did in that mans mouth, not from sex, or blowjobs or handjobs from anyone. Probably one of the most intense orgasms I’ve ever had. He sucked every last drop out of me and swallowed it all. I had to sit for awhile after, my legs felt like jelly.
After I came he asked if I wanted to suck him, but I was feeling a bit of post coital disgust, especially because all I wanted to do was jack off together.
I got dressed as fast as I could and got out of there. The whole drive home all I could think about was the pleasure I just felt. When I got home I was hard again and had to masturbate.
Thinking back on it turns me on. I still masturbate to the memory. If I could I would do things a bit different. I would’ve sucked his cock or let him eat my ass. But hindsight’s twenty twenty.
TLDR; met a guy on Craigslist to jack off together, ended up having the best sexual experience of my life.
Source: reddit.com/r/gonewildstories/comments/g8or3e/my_first_and_only_time_with_an_older_man_m
Would u do it again?