Happened once. Had a friend that lived in the neighbourhood, grew up together basically so we’d seen each other’s junk before plenty of times during the “show me yours, I’ll show mine” phase or just randomly. Anyway, by now we’d message occasionally and at some point confided in each other about crushes and girls we were into. This led to a conversation (still over messaging) where we both admitted to jerking off while thinking of our crushes sometimes, and then from that moment on the ice was broken and we’d occasionally chat about masturbation and porn and what got us off. I’d usually jerk off during those chats and eventually we both admitted to doing so, talking about it and even mentioning when we’d cum.
So then for the one time, the thing you asked about. I was over at his place like usual. And also like usual we were home alone while his parents were at work. We started talking while playing a game and for the first time brought up the topic of porn while actually face-to-face. Talked a little about the specifics of what kind we liked and where we watched it, what sites etc. So I told him to show me some of his favourite videos, and I’d share some of mine. When we we’re watching his video I was hard as a rock inside my pants and just kinda blurted out to him that it was okay if he wanted to jerk off. Just projecting really, hoping I could do it if he did it as well.
Was sort of an awkward game of chicken / “you first, no you first” situation to start, but we both got them out first and focussed back onto the video. At which point we both “sneakily” started stroking. The whole thing stayed quite awkward to be honest. Unlike with messaging, talking about this stuff out loud and face-to-face was a lot more difficult. So there was a lot of awkward silences and unsuccessful attempts at hinting things. Didn’t really last all that long anyway as he got close to cumming he got up and went to the bathroom to finish. I was planning to do the same after he’d come back, but accidentally got myself to close and not wanting to make a mess in his room I finished into my boxers.
I put those boxers back on and zipped my pants up, he got back from the bathroom, I’d closed the porn. We played a bit more of the game we were playing before until I had to go home and we never really acknowledged it happening after.
Yeah, it was a surprise just how different it felt. When it’s just text over chat your imagination fills in a lot of blanks, and of course while you’re masturbating you fill imagine it as the hottest thing to do. Also not having to say any of the things you type out loud helps. When you’re actually in the same room with your dick out it’s so very different.
Chatting about porn and jerking off kind of stopped as well. I actually did bring it up once to ask him about how he’d finished in the bathroom, but it immediately felt like that same awkward vibe about it. So from then on we occasionally still brought up crushes, but our main crushes never really went anywhere at that point and we kind of stopped talking about them too.
I think the whole thing was mainly driven by horny curiosity, and after talking about all the details and having done the thing IRL, it was kind of… done? I guess. I did afterwards occasionally fantasise what it’d have been like if I’d reached over and jerked him off. But I’m 99% sure that would’ve taken it too far for him. Since he wasn’t comfortable cumming next to me and stuff.