I Asked Men About That Time They Jerked Off With Their Friends

If you did all this with a friend or two, you probably weren’t alone – as it were. In the heady puberty-and-constant-sleepovers era, many curious young men polished the banister in the company of their pals in the early hours of the morning – often with barely a word spoken about the deed before, during or after. This was largely what sleepovers were for, wasn’t it?

There’s a little bit of a taboo here. Because of its homoerotic connotations, mention of the behaviour causes some men to bristle. It also seems like isn’t generally something that friends continue to do past their A-Levels. But while wanking with your mates might not exactly be a rite of passage, it’s an extremely prevalent phenomenon in the sexual development of young men. 

“It’s been a common practice since the beginning of time,” says 40-year-old Jason Wimberly, a gay personal trainer who was interviewed for this piece. “For me, I truly believe mutual masturbation between men is an activity that lives beyond the spectrum of self-prescribed sexual orientation.” Wimberly is currently writing a book about men masturbating together.

For some, a communal teenage wank was just a communal teenage wank. For others, including those interviewed, it was a significant step in the journey towards discovering their sexual orientation. Charlie, a 28-year-old gay man, says, “I remember, even then, thinking about what this meant for my sexuality but was quick to ‘reassure myself’ that there was no way my friend was gay, so doing that didn’t mean that I was gay either.”

Here, Jason, Charlie and four other men tell us about a time they masturbated – or nearly masturbated – with their teenage friends. Maybe it’ll bring back some memories for you.

“We were 15 years old, on summer vacation, and my two best friends and I decided to have a sleepover at one of their houses. I guess because of our age, peaking puberty and hormones, we were going through a phase where we talked a lot about sex, relationships, porn and all that stuff. I also had a condition where my testosterone levels during puberty were way higher than normal; I had to take medications to control it until I was 20, and that made me a bit hornier than other guys.

That was also the year we had to start using the showers after PE class. I guess I was lucky because genetics made me pretty well-endowed, and that started a rumour about me in school - guys used to give me nicknames because of it. The mains ones were Centaur (because it’s half-horse), Tripod, and Kid Bengala (a famous well-hung Brazilian porn star).

At the sleepover we were talking about sex, because I’d lost my virginity a few months prior. During the chat, one friend asked if my size was an issue and I said it kinda was – then we started arguing about penis size. After talking about it for a while, my other friend suggested we should compare to see whose was bigger. We lowered our pants and compared – I was clearly bigger. Then this friend said it wasn’t fair because he wasn’t hard and we should get hard to compare. We all agreed (a bit less enthusiastically than before) and then just stood there. I remember one of them said something like, “So we just jerk off here…?” We laughed and decided that each one should go to a different room, get hard, and then come back to compare. I went to one bathroom, grabbed my phone, looked for some porn and started stroking.

I remember it was weird to see all my friends hard like that. It was obvious we were all shy, but after a minute or two we got more comfortable: We compared and measured, and that’s when I found out I was already quite big for my age. After we were done talking about it, we were just three boys with half-hard dicks. That’s when one of my friends said something like, “Well since I'm already like this, I might as well finish,” and we all laughed. He opened his computer to show us some porn and we all got hard again, then started stroking. I remember I was a bit shy at first, but we were able to do it and we actually did it more than once. The first time was definitely awkward but then we realised that if we all enjoyed it, what was the problem?

From that day until we were 16, every time we slept at each other's place we’d jerk off together. It became something quite natural for us, but after 16 we just naturally stopped. We kept sleeping at each other’s places but we stopped doing it – maybe because we started dating, or talking less about sex, or maybe by the end of puberty we were less horny. We’re still best friends.” – Nicholas Martins, 23 

“I found my dad’s Playboys in first grade and learned about jerking off early on. When I discovered how great it felt, I always wanted to tell everyone. My cousins and I started jerking off around ten, well before we could cum, but it still felt amazing – it was just boys enjoying their favourite toys together.

I had my first circle jerk in freshman year with a bunch of my teammates after cheerleading practice. I invited around five friends over to watch an old VHS I’d stolen from my dad, and in a matter of minutes we were jerking off in my childhood living room.

It became a regular thing. A few guys would come over regularly before football games and we’d all rub one out. I was a cheerleader but the other guys on my team were all football players who cheered in the off season. I was the only gay guy. It’s safe to say I was pretty obsessed with circle jerks from then on, I remember them being so fun. Even though I was gay, I never pushed anything until they asked – of course, that time did come.

Just yesterday at the beach, my partner and I jerked off with four new guys – we all stood in a circle and shot a load in the sand. Many think of masturbation as sex, but for me and my friends it’s not a sexual activity as much as it’s a personal activity we just share and enjoy together. My straight friends send me dick pics all the time. We compliment each other’s cocks and say things like, “Dick looks good, bro! Strong!” We can share the pleasure of our hard cocks with each other because our cocks are fucking awesome.

Masturbating with friends is something that’s been so integral to my life. Professionally I lead masturbation rituals and groups: It’s been pretty epic to give guys memories of a 12-guy circle jerk on the top of a mountain.” - Jason Wimberly, 40

“It all began when we were about 11, soon after I discovered masturbation. We had a school trip, so my two friends and I stayed in one room together. One morning I woke up with an erection and curiously asked my friends if they’d ever touched their penises when they got hard and whether it felt good for them, too. They both said yes, so I casually suggested we do it. We basically spent the whole school trip in our room, jerking off under covers - we were too shy to see each other naked. Another friend told us about porn sites then, saying it was “just like YouTube, but with sex” – we thought it was too good to be true.

After that my best friend and I would regularly go to his house after school, since his parents were always out. He had two computers in his room on opposite sides. One of us would play games on one, while the other jerked off while watching porn on the other - then we’d swap. Sometimes we watched porn and masturbated together, but rather than sit next to each other, we put one chair behind the other. We never spoke about it, but I think we were afraid of being ‘too gay’.

One day my friend whipped out his cock while I sat next to him and I freaked out a little bit. We also masturbated every time we slept over at each other’s houses – always under covers and, since it was pre-smartphones, rather than watch porn we told each other about our sexual fantasies, usually involving our female classmates.

It all lasted until we were about 15, then we just stopped doing it for no particular reason. I sort of wanted to keep it doing it, but the longer we didn’t do it, the more awkward it became to bring up. In the end, we both just pretended it never happened and never mentioned it again - we’re still best friends, though.” - Klaus, 26

“I was staying overnight with my best friend, at around 12 years old, and we were discussing how we’d discovered the fun of masturbation. We were also discovering the joy of being candid, vulnerable and open with someone you trust, too.

We were in his bed, talking sleepily into the night, when we admitted to each other that we were both doing it multiple times a day. We somehow decided that we’d masturbate, then we simply removed our underwear under the covers and had a go at ourselves individually. I remember it being exciting, nerve-wracking and awkward. I finished before he did, so I courteously waited quietly until I heard him stop - I don’t think either of us made a peep the whole time, climax included.

When it was over, we both cleaned up and exchanged a few words before drifting off to sleep. I don’t think we ever talked about it again, but it was a fairly innocent exploration and we were soon back to planning activities for our secret club - namely uncovering proof of aliens and exploring forgotten local caves for treasure.

Maybe it’s odd that we never acknowledged it, but it didn’t make the friendship awkward at all. These days I’m still sexually adventurous - I’m currently exploring sex with other couples, parallel play and looking forward to a MFF [male, female, female] threesome in the near future. I can confidently say guys aren’t my cup of tea, though.” - Ryan, 44

“The first time it happened I would’ve been around 13, with a good friend at his house the day after a sleepover. It came completely out of the blue for me and I was a bit of a late bloomer, but he just pulled his phone out and started watching straight porn while we lay on his bed. He started jerking himself off and then encouraged me to start. After a couple of minutes of this, he put his hands down my pants and then I did the same to him. I can’t remember if either of us came, but I was turned on and felt confused and awkward in equal measure. I think the most shocking thing was how nothing was said afterwards and we never spoke about it again. This made me feel like it was something completely normal that maybe he did with other mates – or maybe everyone was doing it? I didn’t realise I was actually gay at the time. There was also shame around it, plus the fear that it was a ‘trap’ and people at school would find out.

I remember thinking, even then, about what this meant for my sexuality. But I was quick to ‘reassure myself’ that there was no way my friend was gay, so doing that didn’t mean that I was gay either. I also remember feeling very seen – how did he know I wouldn’t freak out when he started wanking? And how did he know that I’d be into it too?

Later, around 15 or 16, there’d be the occasional sleepover where talk about hot girls would intensify and end up with the other guys having to ‘let it out’. I’m still unsure how much of that was homoerotic and how much was just sexual frustration. Even from my perspective, I found the general horniness in the air hot, not my friends.

My first actual gay experience was also with a friend at a sleepover, just after I left sixth form. It was pretty similar to the experiences I’d had with straight guys at school, so trying to figure out if this was just another example of the same thing, or something more, was really tough. Any thought that the other guy could actually like me was quickly suppressed by the fear that, for him, this was just another quick release we could never speak about.” - Charlie, 28

“At about 13 I was invited over to my friend Paul's house for a sleepover, as his mum was away. Half-way through the evening his best mate Wayne randomly turned up - I'd never met him, he was from another school. We watched a film and had a takeaway, then just as I was starting to relax Wayne surprised us by getting out a porn film he’d brought with him. Paul then announced we were to have a ‘wanking competition’ - the panic hit me like a truck.

I fled to the toilet and just sat there for a while, my mind flooding with questions. I didn't want to get my penis out but I didn’t want to look a wimp in front of them, either. I definitely didn't want to see theirs. Would we have to compare? If I was the smallest would this change things at school? How would Paul act with me knowing he's the bigger man? Should I moan with pleasure, laugh, or should I stay silent? How do I win? What happens if I lose?

I decided to hit the eject button. I came out and said I needed to ring my mum, I tried to act casual on the phone: ‘Did you say I had to come home?’ My mum wasn't getting the hint and said, ‘No, you're fine.’ The boys got distracted by something and I seized my chance, whispering, ‘Please come and get me, we have porn and they want to have a masturbation competition!’ Mum shouted, ‘Oh God, tell them Nan’s sick, I'm leaving now!’ She ran to the car, shouting to my dad, ‘James is trapped in a masturbation competition and he's panicking!’

I made my excuses to Paul and Wayne, and stood at the window praying they wouldn't start while I was still in the room. My mum couldn't come soon enough – pardon the pun. Mum arrived and left like it was the last flight out of Saigon. I wonder who won.” - Jimmy Jameson, 43

@OhHiRalphJones