Initiating Idea To Jerk W/close Friend

[navywill83]

Best friend of mine from college plans to vacation together and prob share room. He was bi then straight in college and I’m gay. We talk sex to this day in detail. For every str8 bar I go to w/him, he goes to gay ones w/me...likes the attn of guys even. We’re in our 30s.

How do I start the conversation or see if he wants to jerk together to porn or something? I’m not into him, but really believe that jerking together or comparing bods is an awesome bonding btw two friends.

 

[navywill83]

Ideas I have-

- Come out of shower with towel loose and change in front of him
- Ask straight up what he thinks
- Have him see me sleeping nude
- Mention out of 10+ years of being friends, we never seen each other

What do you all think?

 

[navywill83]

Just walk out of shower and bathroom naked?

 

[cedarizzo]

Sounds like the two of you have a very close personal relationship. Why not just ask him to join you in jerking off? Maybe to a porn?

 

[Bonerfan]

I’ve managed to get several of my straight friends to jack off with me over the years. Every time it has started by watching porn together. Sometimes, but not always, alcohol was invoked which just helps lower inhibitions. With each of these friends I had had many sexually charged discussions. They all knew that I openly talked about how much I enjoyed masturbation and how frequently I did it. So it was not that shocking to them when I put my hand in my pants while we watched porn. Soon after I did it they would invariably start squeezing their crotches etc. eventually I would lower my pants enough to expose my erection and then I’d start openly stroking in plain view. Before you know it everybody has their pants down and is openly beating off together.

 

[deleted1025121]

I find the best way is when sharing a hotel room is to just be naked. Take a shower and walk back to common area for something and back. Sleep naked, etc. Be chill about it. All guys get some chub or erections come and go. See if he comments on it. He'll probably laugh. Then you can like shake it in front of him or do the helicopter. Then ask him..what's so funny? Is yours any better? Lets see yours then?

 

[navywill83]

I’ve managed to get several of my straight friends to jack off with me over the years. Every time it has started by watching porn together. Sometimes, but not always, alcohol was invoked which just helps lower inhibitions. With each of these friends I had had many sexually charged discussions. They all knew that I openly talked about how much I enjoyed masturbation and how frequently I did it. So it was not that shocking to them when I put my hand in my pants while we watched porn. Soon after I did it they would invariably start squeezing their crotches etc. eventually I would lower my pants enough to expose my erection and then I’d start openly stroking in plain view. Before you know it everybody has their pants down and is openly beating off together.

This is prob the best. Just to watch and rub some then take it out. I think he would follow. We’ve been best friends forever. Talk about fucking pussy, ass, oral, one nite stands, etc.

Big question - do you need to say anything along the lines of ‘This is nothing gay between us, just being guys’ or ‘Don’t worry I’m not hitting on you.’ Or would that be to direct and set off alarm bells? Lol

 

[navywill83]

I find the best way is when sharing a hotel room is to just be naked. Take a shower and walk back to common area for something and back. Sleep naked, etc. Be chill about it. All guys get some chub or erections come and go. See if he comments on it. He'll probably laugh. Then you can like shake it in front of him or do the helicopter. Then ask him..what's so funny? Is yours any better? Lets see yours then?

Great ideas thanks. Just chill and let it be normal. I like the ask about his if he laughs or says something about mine.

 

[Barberseville]

Let us know how it goes... good luck.

 

[NIMBUS]

If you're sharing a room and have been mates for years, then I can see no problem with setting out the lie of the land from the outset. Just be honest with him:
"Mate, we're going to be stuck in a room together for (X) nights. I know that you jack off, you know that I jack off. Are we just going to go for it and to hell with it or are we going to pussy around each other and pretend that neither of us does?".
Just be open and make it clear that if you wake up in the morning and he's lying on his bed stroking one out, then it wouldn't freak you out and you'd probably do the same and ask him if he would feel uncomfortable if the tables were turned.
There's no point in you tiptoeing around each other and missing an opportunity to bond even further. If he says that he'd prefer not to do that and to jack off privately in the bathroom, then you know the situation and it shouldn't affect your friendship if you're close mates.

 

[Lucius2s1]

This is prob the best. Just to watch and rub some then take it out. I think he would follow. We’ve been best friends forever. Talk about fucking pussy, ass, oral, one nite stands, etc.

Big question - do you need to say anything along the lines of ‘This is nothing gay between us, just being guys’ or ‘Don’t worry I’m not hitting on you.’ Or would that be to direct and set off alarm bells? Lol

pretty awesome

 

[dreamer20]

Ideas I have - Ask straight up what he thinks
What do you all think?

^^This.

 

[collegebud6]

I think you’d just ask him straight up if he’d be down. Sounds like he would be.

 

[navywill83]

I keep feeling that asking straight up may come off as ‘too gay’ or that we are planning on doing something naked versus it being less strange if it just happened. We are really close, but I’d still be afraid that it would leave that time that he may overthink it vs just enjoying the moment.

 

[3877251]

I keep feeling that asking straight up may come off as ‘too gay’ or that we are planning on doing something naked versus it being less strange if it just happened. We are really close, but I’d still be afraid that it would leave that time that he may overthink it vs just enjoying the moment.

You can ask in-person, in the moment when it feels right.

 

[dreamer20]

I keep feeling that asking straight up may come off as ‘too gay’ or that we are planning on doing something naked versus it being less strange if it just happened. We are really close, but I’d still be afraid that it would leave that time that he may overthink it vs just enjoying the moment.

It's not going happen spontaneously or occur as a result of seeing you nude as you proposed. As you will be sharing a room, first ask if he has any issues with being nude around you and vice versa. Even if he responds "No" , be mindful of his feelings by posing the question "Would you be comfortable, or not, with the idea of jerking off to porn with me?" instead of wanking in front of him and expecting him to join in. He may not be comfortable doing that activity with you.

 

[3877251]

It's not going happen spontaneously or occur as a result of seeing you nude as you proposed. As you will be sharing a room, first ask if he has any issues with being nude around you and vice versa. Even if he responds "No" , be mindful of his feelings by posing the question "Would you be comfortable, or not, with the idea of jerking off to porn with me?" instead of wanking in front of him and expecting him to join in. He may not be comfortable doing that activity with you.

I like this. Another idea: I’d probably simply start by sharing that you’re horny/turned on. In my experience, when the conversation goes to sex and what turns you on, you’ll know if he’s comfortable by his reaction. If he changes the subject, that may be a good sign that he’s more uptight. If he goes with that, you can let him know that you need to jerk off or can’t wait to. Listen to see what he says. If he agrees or seems interested, I think it’s a good time to ask if he wants to jerk off — “so, do you want to do it?”.

 

[The Law]

When is this room-sharing situation happening?! Would love an update afterwards to see how it went!

 

[navywill83]

When is this room-sharing situation happening?! Would love an update afterwards to see how it went!

Not for a while. Especially since covid happened, we had to push things way back.

Will def update!

 

[ronin001]

You are not in college any more, you are in your 30s; and scheming how to JO with a close friend, is kind of immature
The old put on porn and start rubbing myself works well in porn videos. The I'm just out of the shower and casually expose one self thing, sounds pervy / creepy . and would probable just be an quick glance, with nothing coming out of it

Friends generally should not scheme / plot against other friends . Try being Honest , all he can do is decline. But you would still have a friend