u/Adventurous_High5644

TLDR: after having had open masturbation with a previous friend and a roommate, I am hoping to ask a current friend to masturbate together.

As the title says, I have had previous fun with friends, and even a glorious period of time where myself and my roommate would masturbate totally freely and openly.

Since then though, I have moved and havn’t had any such mutual fun. So I am planning on bringing it up with my current friend.
I’m sooo nervous because the last few occasions it happened a bit more naturally, and emerged out of practicality with my roommate, but this time I’m purely motivated by my desire for fun with them.
I have seen them naked before, and them me, when we have been changing at a swimming pool, so we are a little more comfortable in that regard, but it’s still a big risk.
We have spoken about sex before, and a bit about when and how often we masturbate, so we are both definitely a pair of horny fuckers but it’s going to be pretty challenging to bring up.

I’m thinking of inviting them over for a drink and then bringing up sexual topics until it feels more natural to bring up my desire. I’m also wondering about maybe asking them to stay over, I feel like at night it’s gonna be more normal to mention it, and I could also say, this is my usual time to masturbate, so do you wanna do it with me?

Idk though, I’m gonna have to play it by ear, any advice let me know. I’d be curious to hear. Thanks!

TLDR: A long term friend who I had seen naked many times finally masturbated with me when I brought up their dick.

A couple years ago I was really good friends with a guy, we studied together most days, went out together, but crucially we were in the kayaking society together. Because of this, we would go to the local swimming pool semi-regularly to practice kayaking, and we would also go out to events ect. This often involved open plan changing rooms where we would get changed into our kayaking clothes. This meant I had routinely got changed with him, and we were both extremely familiar with being naked together.
This gave our friendship a unique edge that made us wayyy more intimate than I would be with any other friends.

Anyway, I had often noticed how he looked when we were getting changed, and I can’t lie, I thought he had a really nice cock, so I did catch myself starting from time to time but I generally tried to be discreet about it.

On one occasion we went to practice and I was already in a kind of horny mood for whatever reason, and he caught me looking at his dick, I looked away, though I saw him glance at mine too.
Anyway, I thought no more of it and after practice we got changed as usual, and he invited me to go for some drinks after. This wasn’t uncommon and I went with him. Over the course of the evening we chatted about our work and various other topics, which stretched quite late into the night and left us both fairly drunk. So he invited me to stay at his place instead of making the bus journey back to mine. Again, this wasn’t too uncommon and I obliged.
We got to his place and he lay out an air bed on his floor and stumbling around we prepared to go to bed.
As I was washing my face he came into the bathroom and grabbed his pyjamas, he then got naked and started changing into them. I saw him in the mirror and in a slightly drunken blurt said ‘have I ever told you you have a nice cock’ he just laughed, as did I, and he said thanks. He also said I need to stop looking. We both laughed as everything is funny when you’re a bit drunk and I continued to look at him, this time being deliberate to stare. I said ‘wouldn’t it be more fun to sleep naked, I have no pyjamas anyway’, again laughing. He responded ‘we can if you want, I don’t want you to be left out.’ He said this in a kind of teasing fake cry voice. Again we both laughed. He then left the room to go to bed. I was now pretty turned on as my inner exhibitionist would be, and I quickly went back to the bedroom.
We both kind of laughed as I entered and he was laying with the covers to the side, and was clearly naked.
I then got naked in front of him and was now almost certainly a little hard, he looked as I had done to him before, which only made the situation more horny as far as I was concerned.
He laughed a bit more, but it was notably subdued now. He said ‘I saw that’ and laughed slightly.
Drunk as I was, I was kind of embarrassed now, and said ‘what’, he said ‘I saw you were hard’. He laughed and I did. I said ‘sorry, I get a bit horny sometimes’. He said, ‘it’s fine, have a wank if you want to, I might’. I was kinda shocked but loved being naked so said thanks, and asked what porn he usually watches. ‘He said he likes ts stuff’. I was shocked and pulled some up on my phone, and said ‘like this’ he said yes and was now visibly hard. I was also throbbing to the point of feeling the precum slide down the inside of my shaft and out onto my tip.
I said ‘I might need to have a wank, I’m not sure I can take it’ my breath short as I said it. He said ‘me too’ and we both started jerking off and sharing porn between each other. I made sure to keep myself fully visible and enjoyed him looking at me, and i made sure to look at him. Eventually he came and I watched the cum spray across his chest and i came shortly after. he then handed me a tissue and said how fun it was.
We both agreed it was super fun and went to sleep quite quickly after.

Hope you enjoyed this recount from my university days. Any similar stories, feel free to share.

TLDR: after hearing my roommate masturbate regularly, I confronted them and we masturbated together. After that, things got REALLL casual…

I posted about catching my roommate in more detail before. But the long and short of it was that we were both superrrr horny people, and I caught him jerking it after he *thought* I was asleep. So I confronted him and encouraged him to just be open about it so we could do it at the same time and stop having to avoid each other to do it.

Anyway, after the initial jerk session that kind of broke the ice, things were pretty awkward in the morning I can’t lie. However, the whole experience I found really thrilling and I knew it couldn’t be the last time.

Because of this, and because I knew I was the more confident one (or horny one), I made sure to take the lead the next night.

So after a slightly awkward time getting ready for bed, with my roommate avoiding eye contact we both lay in bed and my mind flashed through what happened the night before. I could feel myself getting hard and knew I needed to try and initiate it. So, out of the darkness I just looked across to his bed, and said, ‘I can’t lie, I’m pretty horny, and last night was fun, wanna jerk off again’. I think flustered by my directness, my roommate nervously said ‘yeah I’m kinda horny too’. To help ease us into it I asked him what kinda porn he usually watched while I’m ‘asleep’ I said this in slightly teasing way and he laughed a little. He said he likes amateur blowjobs, so I used my IPad to pull up some videos and showed him, I asked if he likes them and now feeling more bold he said yeah, and told me he’s starting to get hard. I said me too. Then we discussed how it would be wayyy easier if we can get more comfortable with this because trying to sneak in sessions while the other person is out is sooo annoying.

Fairly soon I decided I couldn’t take it anymore and went back to my bed and got my dick out. I made sure it was visible under the light from the screen, and when I looked over, my roommate had done the same. This time I made sure he saw me looking at him and he responded in kind. It was sooo hot feeling observed while doing it, and we both enjoyed ourselves until I looked over and saw him shoot cum over himself, and I let myself do the same.

In the days that followed, we got more and more used to it, and things got a lottt easier, we would even start by getting into bed naked and just watching porn without much discussion and it came a fun little part of the day.

Eventually, things escalated further, but perhaps that’s a story for another day…

Hope you guys enjoyed.