Some unexpected sleepover fun in my 20s

NSFWOne Night Stand

So I'm 30, male, and mostly straight; but back in 2020 (9 months before I met my now-wife), this confusing but also hot experience happened.

I had been living overseas for two years, and I had just gotten back in touch with my former best friend from high school (who we'll call Alex - not his real name). We agreed to have a sleepover like old times so we could catch up, play some video games, and just talk about life. So fast forward to the sleepover & when it came to later at night, after food & video games, we both stripped down to underwear (as said before, we used to be best friends so boxers weren't a big deal) and lay on the bed. We were talking about relationships each of us had had in the previous few years, and that topic turned to girls (and eventually to sex).

After talking about sex a little - mostly his experiences as I was inexperienced - we were both getting visibly turned on and hard through our underwear, and both sort of casually moving our hands down there. I don't know who did it first, but pretty soon we were both masturbating while talking, and soon after that the boxers came off as we got totally naked. I was very turned on, albeit a bit confused as I'd never done this before, both watching me stroke himself naked just felt so taboo and exciting.

After a few minutes of that, we moved closer on the bed and switched hands to start stroking each other, which was the first time I ever touched another guy's cock. Both of us touched and stroked each other for a while before he went down and started sucking me off. That was enough to make me cum in his mouth, although afterwards I was too embarrassed and confused (not to mention residual religious guilt from my upbringing) to return the favour, so I just watched as he got himself off.

I'm married to an amazing woman now, but sometimes I still think about that night and fantasise a little!

Posted Mar 8, 2026, 5:53 PM UTC

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