Advice For Roommate Fun??

Hawkeye319

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This is all probably a really far fetched fantasy but figured why not ask for peoples advice on potentially having a mutual masturbation situation with my roommate

So I’m a single gay male, been pretty horny lately and as a result have been listening in on my straight male roommate while he jerks it. He’s not necessarily loud or anything but sometimes I’ll hear the bed squeaking or some deep breaths, and not gonna lie it’s hot thinking of a guy jerking off near me. We’ve got a pretty cordial and casual friendship/roommate situation but haven’t really opened up to talking about sex and stuff like that, but I guess that wouldn’t be normal. So I’ve really just been thinking of a potential platonic situation for masturbating. Honestly I just wanna watch him jerk off and like nothing else I don’t have any romantic feelings for him or anything like that but the idea of seeing him jerk off has really been turning me on, I’ve even been having dreams about it lately. Any advice on how I should go about this? I’m thinking maybe one night we both have a little alcohol that way we both feel comfortable at least talking about masturbation and sexual stuff(obviously I’m not trying to get drunk and try to do stuff to him) think it could be harmless fun honestly and honestly I just wanna see if he would be even open to the idea of something like that. I know this is far fetched considering he’s straight and all but we’re both stuck in our apartments most of the time anyway, might as well have some platonic fun with jerking off lol
 
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So disclaimer first: be careful going down this road. If it should backfire on you in some way, it may get uncomfortable living together. Or he could just decide to move out before the lease is up and leave you with figuring out how to pay the rent.

That said, one thing you could try is to let him "catch" you in the act of watching porn. Do this at a time when you expect him to be coming home, like when he gets off work. If you have a DVD player, that would be best since it would be obvious on your TV what you are watching whereas he might not notice it if you are on your computer or phone. Straight porn would be best as it might entice him to join you in watching it. Just be prepared if he asks you why you are watching straight porn so you sound convincing when replying that you like watching all kinds of porn. You can be shirtless, but definitely still in shorts or sweats. That way you can sport a semi or more without scaring him off by being fully nude.
 

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I was in the exact same situation. My roommate is incredibly sexy. I wanted to hook up with him from the moment we met. But he was is my best friend, my brother, and I didn't want to do anything to mess that up.

So one day, he said he had a girl coming over to hook up. She got there and as they were about to go in his room, he called me over and told me to come with them. A mmf three-way was the easiest way to get him naked and he was already naked and horny so whatever happened happened.

Now we have a lot of fun together. We even have a fleshlight that we share. So maybe try that. Having a woman there made him a lot more comfortable.
 

Hawkeye319

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Maybe I’ll just keep updating this thread as I build up courage to talk to him about jerking off together lol. So maybe this will be a fun lil adventure for us all!
Today I did something a little adventurous I guess, when jerking off today I left my door cracked and didn’t use headphones while watching porn nothing to forward but I guess just a way to be like I’m a bit comfortable with jerking it in the open I guess? Will probably be a slow process but eh I’m bored and horny so why not I guess?
 
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That's not a bad way to start in my opinion, but not sure how wide you want to leave the door open when you know he's home. Still, even just a crack and no headphones does add some danger of being caught. And if it helps build up your courage to properly get "caught" one day when he's coming home, more power to you.

Good luck.
 
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Freedmanj

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Sounds like a good approach so far. Not sure if you share a bathroom but maybe show him you’re comfortable walking to and from the bathroom in just a towel etc to start building up a level of confidence between you
 
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This is all probably a really far fetched fantasy but figured why not ask for peoples advice on potentially having a mutual masturbation situation with my roommate

So I’m a single gay male, been pretty horny lately and as a result have been listening in on my straight male roommate while he jerks it. He’s not necessarily loud or anything but sometimes I’ll hear the bed squeaking or some deep breaths, and not gonna lie it’s hot thinking of a guy jerking off near me. We’ve got a pretty cordial and casual friendship/roommate situation but haven’t really opened up to talking about sex and stuff like that, but I guess that wouldn’t be normal. So I’ve really just been thinking of a potential platonic situation for masturbating. Honestly I just wanna watch him jerk off and like nothing else I don’t have any romantic feelings for him or anything like that but the idea of seeing him jerk off has really been turning me on, I’ve even been having dreams about it lately. Any advice on how I should go about this? I’m thinking maybe one night we both have a little alcohol that way we both feel comfortable at least talking about masturbation and sexual stuff(obviously I’m not trying to get drunk and try to do stuff to him) think it could be harmless fun honestly and honestly I just wanna see if he would be even open to the idea of something like that. I know this is far fetched considering he’s straight and all but we’re both stuck in our apartments most of the time anyway, might as well have some platonic fun with jerking off lol


I think the messages of don’t shit where you eat are valid. Especially in this COVID word. It would suck to have to find new living conditions in all this shit.
That being said, if he is a straight guy living with a gay man, he probably isn’t a homophob, so you probably have a little more wiggle room to not have a massive disruption.

I would bring it up in a round about way, and read the room. If he is super cold, don’t bring it up again. But if he kind of laughs or whatever, explore it more.
I am straight, but I wouldn’t care if my gay roommate saw me naked or even if I was having sex or jerking off to porn or something. But I don’t have any interest in sitting side by side or facing each other and both jerking. I am an exhibitionist but not in that way I guess.
Maybe you guys watch some straight porn or something. He focuses on the porn and you focus on him???

this is a crazy world right now, so anything is possible.
 

Hawkeye319

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I think the messages of don’t shit where you eat are valid. Especially in this COVID word. It would suck to have to find new living conditions in all this shit.
That being said, if he is a straight guy living with a gay man, he probably isn’t a homophob, so you probably have a little more wiggle room to not have a massive disruption.

I would bring it up in a round about way, and read the room. If he is super cold, don’t bring it up again. But if he kind of laughs or whatever, explore it more.
I am straight, but I wouldn’t care if my gay roommate saw me naked or even if I was having sex or jerking off to porn or something. But I don’t have any interest in sitting side by side or facing each other and both jerking. I am an exhibitionist but not in that way I guess.
Maybe you guys watch some straight porn or something. He focuses on the porn and you focus on him???

this is a crazy world right now, so anything is possible.
Yeah I’m definitely not expecting to start giving my roommate blowjobs every day or anything like that lol, just looking to maybe have some fun with watching porn together and yes maybe something where he’s more so focusing on the porn but I’m more so focusing on him.
 

Hawkeye319

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No updates for the past few days lol all I did yesterday was watch open without headphones with my door closed this time. Still trying to work up the courage to just start talking about sex/masturbation like I said our friendship is pretty cordial so I feel like talking about jerking off out of the blue might be coming out of left field lol
 
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Excited to see how this progresses. Watching porn with the door cracked is a solid entry point. Wouldn’t be a bad idea to drink together one night and bring it up when you’re both feeling more open, gauge his reaction.

Jacking it in the living room, porn on the TV, where he can catch you is also a great idea to gauge how upset he is by seeing that (although I wouldn’t expect him to join that first time).
 

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Before I came out, I had a roommate that was dating a coworker of mine. One day while he was gone. I jacked off to a gay porn. I forgot to put it away when I was done and he found it. He moved out of the apartment before I got home. He never talked to me again but he did continue paying his rent. He eventually did find somebody to take over his past if the rent. It worked out because the new guy was really cool and we got along great.

Years later, I let a fuck buddy move into my house. Before he moved in, we had sex usually once a month for a few years. When we lived together, we never messed around again. He always had a different guy over each night. But the few times I was horny, I would watch porn in my bedroom, with the volume turned up and the bedroom door cracked open. He would walk by my room (the bathroom was across the hall) but he never did join in or watch. A few weeks before he was moving out, I had a guy come over. The ONLY guy I ever had over. My roommate freaked out, caused a scene and left the house. He moved out the next day. I haven't spoke to him since.

In both cases, I wish things had happened differently. But either way, I learned that the roommates weren't who I thought they were going to be.
 

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Before I came out, I had a roommate that was dating a coworker of mine. One day while he was gone. I jacked off to a gay porn. I forgot to put it away when I was done and he found it. He moved out of the apartment before I got home. He never talked to me again but he did continue paying his rent. He eventually did find somebody to take over his past if the rent. It worked out because the new guy was really cool and we got along great.

Years later, I let a fuck buddy move into my house. Before he moved in, we had sex usually once a month for a few years. When we lived together, we never messed around again. He always had a different guy over each night. But the few times I was horny, I would watch porn in my bedroom, with the volume turned up and the bedroom door cracked open. He would walk by my room (the bathroom was across the hall) but he never did join in or watch. A few weeks before he was moving out, I had a guy come over. The ONLY guy I ever had over. My roommate freaked out, caused a scene and left the house. He moved out the next day. I haven't spoke to him since.

In both cases, I wish things had happened differently. But either way, I learned that the roommates weren't who I thought they were going to be.
Omg thank you for this i swear
 

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Like the idea of “accidentally” leaving something out that might be a catalyst to opening up conversation.

Does he know you are gay?
Have you had a discussion about overnight guests?
Are you comfortable enough making a light-hearted comment to him the following morning following one of his more “active” JO sessions?
 
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Hawkeye319

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Like the idea of “accidentally” leaving something out that might be a catalyst to opening up conversation.

Does he know you are gay?
Have you had a discussion about overnight guests?
Are you comfortable enough making a light-hearted comment to him the following morning following one of his more “active” JO sessions?
He does know I’m gay, we have not had a conversation about overnight guests but he does talk about dates he goes on with girls and stuff but these are all non sexual situations, and I eventually could see myself making a light hearted joke the morning after or something like that. Like I said our roommate situation is fairly cordial but we really haven’t gotten to that point of openly talking about sex, or at least he hasn’t. I’ve mentioned hooking up with guys in a fairly general sense
 
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He does know I’m gay, we have not had a conversation about overnight guests but he does talk about dates he goes on with girls and stuff but these are all non sexual situations, and I eventually could see myself making a light hearted joke the morning after or something like that. Like I said our roommate situation is fairly cordial but we really haven’t gotten to that point of openly talking about sex, or at least he hasn’t. I’ve mentioned hooking up with guys in a fairly general sense
How does he react/respond to your comments about hooking up?
 

Hawkeye319

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How does he react/respond to your comments about hooking up?
Nothing out of the ordinary just a neutral reaction I guess. I’ve only mentioned hooking up with guys a few times and it’s only in general conversations we don’t really dive into talking about sex. Honestly think we need to just have a night of drinking to maybe chill out enough to both talk about that kind of stuff.
 

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I used to experiment and hookup all the time with my roommates in college. Every year I'd be paired up with a random jock or frat bro who would become my friend. Things would always escalate since they/he would know that I was bi and hung.
 

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Nothing out of the ordinary just a neutral reaction I guess. I’ve only mentioned hooking up with guys a few times and it’s only in general conversations we don’t really dive into talking about sex. Honestly think we need to just have a night of drinking to maybe chill out enough to both talks about that kind of stuff.

I think this where you need to start. If he is not comfortable enough to talk about sex with you. He is def not going to be comfortable enough to masturbate in front of you.

In my experience as an openly gay dude who had many straight roommates in college getting him to feel comfortable around you will be the biggest hurdle. Not because he’s homophobic or anything like that. He probably nervous he’s going to say or do something that going to offend you. You need to get him to see you as one of his boys than his gay roommate. A night of drinking and sharing can aid heavily in this effort.

once he feels like he can joke with you and be open. Your chances of seeing him Jack off goes up immensely.

Trust me! once I was considered one of the “boys” by my straight roommates all but 3 (7 total) had exposed themselves to me by the end of us living together. I probably could have gotten a couple of them to do more if I really pushed it back then- haha
 

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I used to experiment and hookup all the time with my roommates in college. Every year I'd be paired up with a random jock or frat bro who would become my friend. Things would always escalate since they/he would know that I was bi and hung.
Sounds like fun. I never hooked up with roommates in college, but I did hookup with guys in my dorm.