I’m [M] straight but I met a stranger [M] to jerk off together

I’d like to start with some history that might explain why I eventually tried this out, but for those that just want to jump to the title story, it’s the section between the lines.

I’m in my 30s now, and I think my porn and masturbation experiences as a younger man were somewhat common at the time. I remember when my friend and I tried desperately to clearly see tits on the scrambled cable porn channels, or find someone who had HBO so we could watch Real Sex. Eventually we discovered (dial-up) internet porn, and I remember very late night chats on AIM or ICQ exchanging links. My friend eventually got broadband, and I remember staying over at his house frequently, and it would almost always turn into hours long porn surfing sessions. Of course we’d also talk about the women that we were interested in at the time. How hot they were, whether they might be interested in us, how far we’d gotten – normal stuff like that.

We’d never jerk off in front of each other, but I do remember sneaking off to jerk off in private or after we’d turned in for the night, and a few times it was clear he was doing the same. We eventually started talking more and more about our masturbation habits. Stuff like how often, how much cum we shot, whether we shot or dribbled, and so on. It really made me wonder how my cock compared, and wanting to see someone else’s cumshot. It also helped that my friend and I eventually gravitated to more and more cumshots in our porn. There were times we’d even be overtly rubbing ourselves through our pants. I remember thinking a lot in those times that it was silly we couldn’t just get our dicks out and jerk off – we both knew we did it, so why hide it. I finally worked up the courage to ask, and unfortunately my friend just didn’t want to do that. Luckily it didn’t make anything weird, and we’d continue our porn viewing and overt pants rubbing, but we never jerked off together. Eventually our lives just grew apart until we stopped talking to each other completely.

In that time I had a handful of other friends I was able to talk openly with about porn and masturbation. Another one in particular was a lot like my earlier friend. We’d surf porn together, talk about women, and be up front about masturbation. One time, over his house, after a particularly in depth discussion about our current crushes my friend announced “well, dude I really gotta jerk off before bed.” I told him that was fine with me, too nervous to take the opportunity immediately. He got up and laid down on the other side of a table that was positioned in the middle of the room. I heard him pull his dick out, but couldn’t see anything. Finally I said, “I need to jerk off, too…can I join in?” Sadly, he replied that I should go to the bathroom to jerk off. I just told him nevermind, and heard him continue his stroking. Eventually I could tell he finished and he came back over the his bed on the same side of the room as me, and went to sleep.

It was pretty disappointing to me, because at that point, I really wanted to at least try jerking off with a friend. All that horniness that accompanied those experiences with open conversation and surfing porn with a friend cemented in my mind the need to eventually do all that and also be able to get off in front of each other.

In college, ironically, I kinda forgot about my desire to try this out. It would have been the perfect time to try it, but I think being so busy with school, and having my first real experiences with dating had all my attention in those days. I continued being a pretty open person about porn and masturbation with my close friends, but not to the degree of my earlier friends. It was usually just casual jokes and one-off comments.

Settling down after college with a job and my first long-term girlfriend, I think I eventually got a little bored with my life. I started surfing more porn again and fantasizing about different experiences. Eventually I re-discovered my interest in wanting to jerk off with another guy. The trouble was that I had no idea how to make it happen. At the time, craigslist was the best option. So I found myself surfing the casual encounters section, wondering if I should try to contact anyone or post my own ad. The idea of meeting a stranger on the internet was way too risky to me. I didn’t want to go to a stranger’s house and I didn’t want a stranger coming to mine. I was too scared to tell my girlfriend about any of this and took the unfortunate option of just not wanting her to find out if I tried this. Eventually I’d find guys online to jerk off with, but get guilty and frustrated, and just delete those accounts. This probably went on for years.

At one point an old friend (different from the ones I already described) was going to be in town and wanted to stay with me. It just so happened my girlfriend was going to be out of town for something – I can’t remember. We had a great time, just like the old times, playing video games and talking about women. One night we wound up on my computer, just bullshitting, and kind of filtering through old pictures. I can’t really remember what happened but I think I must have scrolled over to the next picture and it switched folders. Lo and behold there was a picture of my topless girlfriend sucking my cock. This was a long time ago but I really don’t think I planned this. I remember being kind of embarrassed and apologizing, particularly for seeing my cock – I assumed he didn’t really mind the surprise view of my girlfriend’s tits. He didn’t mind at all, and actually said he was ok if I wanted to keep going through that album. I agreed, and we started going down the rabbit hole. I’d gotten a new camera around that time and I used it a lot, so there were lots more pictures like it. Full disclaimer, I recognize now that this wasn’t a good thing to do without my girlfriend’s acceptance, but unfortunately it seemed harmless enough at the time. I think I’ve grown, but I admit I did get a vicarious exhibitionist thrill out of it at the time. He kept all this knowledge completely to himself, pretty much as if none of this ever happened. Anyway, like my other friends, we never got our cocks out or anything like that. Just browsed, and had a pretty open discussion about our relationships. I remember his girlfriend at the time had a pretty huge set of tits, and he also indulged me in a few pictures he had. Anyway, again, the night winded down naturally and we ended up going to sleep, and nothing like that happened since. Unfortunately this is another friend who I’ve also lost contact with over the years as our lives took us in different directions.

That was another experience that really solidified my interest in eventually trying this, one day.

*****

At some point, I was going to be traveling for my job, without any coworkers, for the first time. I think any guy who’s spent days or weeks in a hotel, by themselves, for work, will attest to the amount of porn and jerking off that inevitably leads to. It’s a lot. I found myself surfing craigslist and wondering if I should finally find someone to jerk off with. I decided to post an ad thinking I’d maybe never get a better opportunity to try it. I went through a lot of responses, and I get the usual mixture of complete nightmares and normal-enough seeming guys. I think I whittled the list down from a dozen or so responses to maybe 2 or 3. Eventually it came down to one candidate and I had the same familiar flaky feelings of not really wanting to risk meeting a complete stranger for this, and feeling guilty about wanting to try this without my girlfriend’s knowledge.

He was just persistent enough to push me past my flakiness without turning me away, somehow. He suggested that I just tell him what hotel I was staying at, but not give him the room number. He’d show at the lobby, email me, and I could come down to scope it out. If I was comfortable, I could invite him to my room, but if not I could email him that it was off. I was still a little uncomfortable but it seemed ok enough to accept that small amount of risk that he was a total nutjob that would make the rest of my stay at that hotel a nightmare.

So I sent him the hotel address. He said he’d be there in 20 minutes. We exchanged our first names to identify each other. I immediately regretted everything, and became all nerves with a very small amount of excitement. Finally I might try this out, maybe he will rob or murder me, I hope my girlfriend never finds out. I spent the 20 minutes tidying up, pacing around, getting my laptop set up for some porn, and wondering what the hell I was doing.

I got the email from him saying he just pulled up and would be in the lobby in a minute or two. I peaked out my hotel window and saw someone walking from his car to the hotel front door. I feel like he must have seen my window movement and looked up, catching me, and I think I saw a small grin or something, but maybe it was just my nerves at that point. I decided “fuck it, I’ve come this far” and headed down to the lobby hoping nobody there would immediately figure this situation out.

I saw the guy that had just entered the lobby and it did look like he was waiting for someone. He looked to be maybe 10 years older than me, a bit heavier set than me, but not really overweight, average height, his hair was a little thin. He wasn’t completely what I expected, but he looked sane and normal enough.

I approached him and called his name. He responded questioningly with my name.

At this point I was completely nervous, possibly shaky, but this was happening now. So I just went with it. We gave each classic “hey how’s it going” greetings and I asked if he wanted to head up to my room.

I think I could tell he was a little nervous and feeling awkward, too. Which helped reassure me. We headed down the hall, to the stairs, to head up to my room. Along the way, he laughed nervously which put my nerves right back on edge. I asked him what was up and he only said that this was all pretty strange and he was feeling uncomfortable. I just sorta laughed it off and agreed.

We made it to my room. It conveniently had a small armchair in addition to a small sofa and a coffee table. I had my laptop already set up on the coffee table. I offered him the sofa and I took the armchair, so we were probably sitting about 6 feet apart, each of us off to one side of the coffee table. For a while we just chit-chatted. I was there for work, had a girlfriend back home, he also had a girlfriend who he was having some kind of argument with at the time. Eventually there was a lull in the conversation and our attention focused on the laptop between us. I took the cue to start pulling up some porn.

We surfed porn for a little while, probably over the span of 20 minutes or so. We’d make comments about what we found hot, mixed in with conversation about our relationships. It was starting to feel a little too normal, maybe normal enough that it would be weird to suddenly offer to jerk off together. I started having doubts about the whole thing, and maybe I didn’t really want to do this after all. Still, I was definitely sporting a hard cock in my jeans, and needed to jerk off. So I didn’t not want to do it either…

He finally broke the ice, thankfully, I think. He just went for it and said “well, dude I really gotta jerk off!” And, just like that, he slid his pants and underwear down. His hard circumcised cock sprang out. I’d never seen another guy’s cock in person before. It was a little bit shorter than my cock, but a little bit thicker. He had a bit of a mushroom head. Then my eyes scanned downwards, and I saw that his balls were huge, and hanging low. I couldn’t help myself and exclaimed “wow, man, your balls are huge!” He laughed it off and just said he knew and he hadn’t cum in a long time, too.

Anyway, I’m a polite host if anything, so I followed suit, and pulled my pants and underwear off, too. By comparison, I’m also circumcised, my dick’s a little over average in length, and maybe just slightly over average thickness. My cock head’s one of those that sort of just run straight out from my shaft; a pointy arrow quality rather than a bulbous mushroom head. My balls aren’t nearly as big as his, and they usually sit pretty tight, especially once I’ve started jerking off. So overall, it was cool seeing a guy’s cock and balls that were somewhat different to mine.

We started off just playing with our cocks a bit, while we surfed porn. Slowly this turned into full on pumping, and our dirty comments about the porn got a bit dirtier. I was still sitting over in the armchair with him on the couch, and we were both still wearing our shirts. I still wasn’t sure what was ok or not to do. I was really curious about seeing another guy’s cock, and watch him jerk off, but I didn’t want to make him uncomfortable. So, I just stole some quick glances over in between watching the porn. Eventually I noticed he was doing the same thing. So I just went for it and announced that the whole point of jerking off together is to be able to watch each other jerk off, too, so we might as well be more open about wanting to do that.

This turned into more openly watching each other and making some comments about each other’s cock and balls. I eventually took my shirt off, and he did the same. I made my way over to the other side of the couch, rather than the armchair. It was clear we were both edging hard at this point and thinking more and more about cumming. Our stroking was getting faster and our breathing was getting deeper.

At some point here I made an offhand comment about how much his big balls were bouncing around. He chuckled and then unexpectedly said “you can touch them if you want…I was thinking about doing the same to yours”.

I kind of froze. I really didn’t want to do that. There was an awkward tension in the air, and I just wanted to keep jerking off, watching each other, so I tried to keep it simple and clear with “sorry, I’m not comfortable touching each other”. I got the sense he was maybe a bit frustrated with it, but didn’t bring it up again, and we continued jerking off like before.

Eventually, he started pumping his cock hard and fast. I’d been on edge for a while at this point, so knowing where this was going, I started stroking harder and faster, too. He was ready to cum, and so was I. After a few seconds he announced “damn, I’m gonna shoot!” He leaned way back in the couch, bucking his hips, and after a beat, cum sprang forth out of his cock. All of a sudden he was spraying it all over the place, it wasn’t very thick, but it was so much cum, shooting out in small ropes and droplets. He covered himself, and a good portion of the couch seat between us. In retrospect I feel bad for the cleaning person but I’m sure every hotel couch has seen far worse.

I kept pumping my dick hard and fast now, feeling my own finish building. I uttered “wow, fuck, that was a ton of cum!” and he replied with “haha, you saw my big balls dude, I was so ready to shoot”. At this point it was my turn, and I announced “yeah, fuck, I have to shoot too…”. I leaned way back myself, glanced over to see him watching intently, and erupted. I tend to shoot pretty large, thick, ropes, and after a long edging session like this, I shoot really far. This was certainly no exception. I didn’t cover the couch seat like he did: most of it landed on me, but some landed around my neck, on the seat. Again, sorry cleaning person.

After that, clear post-cum regret sank in. We quickly said that was a lot of fun, offered goodbyes, and he left probably within about 2 minutes. Overall, I realized I really enjoyed the experience, despite the small awkward parts here and there.

*****

I’ve had a few more experiences over the years, mostly online, but a few times in person. All of my in person experiences are many, many years behind me at this point, but I’ve had some fun online experiences more recently. My interest in wanting to do this comes and goes, and I have a girlfriend now that at least knows of my interest in wanting to do this, but unfortunately I’ve still been too scared to share my experiences.

Source: reddit.com/r/gonewildstories/comments/m32l2i/im_m_straight_but_i_met_a_stranger_m_to_jerk_off