Several of my closet buds jo with me, and sometimes, I think its b/c we jo together that they're my closest buds.
My friends know my routine. I always clean the pipes before going out at night, so they know if they're hanging at my place when we've got plans later, it's a given we're all going to empty our chambers before getting ready. Dudes at this point invite themselves over, so I know they're not just indulging me, but its a mutual bonding experience we all enjoy.
Now, it has probably been about a year since I've 'introduced' someone new to my routine, but just as always, it wasn't a big deal. The guy is a really good buddy now and we hang out (and jo together) on the regular. At the time, he was a friend of a friend and a bartender at a new local taproom I had started to frequent. We got to chatting one night and he was saying how we needed to hang out. He saw the girls I would bring to the bar, and "had to see" my approach to meeting women. I agreed to hang out the next night and we exchanged numbers.
The next morning, I texted him and told him he should come over to my place early to hang. I invited him over to bbq and play xbox. He said, "see you in an hour!"
So here are the 3 things I did to get this newbie warmed up to eventually rocking out with his with cock out....
1. The transition from playing xbox to a mutual jo session has to be easy and seamless, so I go shirtless and commando while wearing my basketball shorts. Of course there's some legit VPL, but that's kinda the point.
2. I like to pull out some weed. It just chills everyone the fuck out.
3. While hanging, talk about sex. Start with a question like "when was your last relationship?" and transition to "when was your last fuck?" Talking about conquest. Get descriptive.
Do all three of those things, and the dude will be ready when you say, "Well, I guess it's about time to get ready to go out for the evening. I'm going to take a quick shower, but before I go out, I usually like to clear my head by rubbing a quick one out. What kind of porn you into?"
You notice, I don't ask if he wants to jack off? Or if he cares if I jack off? You just presume he's going to be cool with it and he will be. The dude responded like they always do, "Oh... uh... I don't know. I guess I like everything." Or something of that nature.
To make him complicit and more comfortable, I tell him to pull up something he really likes on his phone and chromecast it on my tv. While he's doing that, I'll go grab a tissue box for him. I also tell him "I just put some fresh towels in the guest bathroom if you'd like to shower off afterwards" and "you can borrow anything in my closet for the night." I assure him that when we meet some girls later, we can bring them both back to my place to party... the guest bedroom is all his.
The guy puts some Kendra Lust on the tv. I commend his choice while rubbing my cock through my shorts. I sit back down in my chair and lower the waistband just under by balls and start to slowly stroke. The guy plays with himself through his pants for a little while longer, but no one is going to cum in their pants, so his cock of course eventually comes out too. I find it helps in making the other guy comfortable if you keep commenting on what you're watching and making it about what is on the tv and not the other cock in the room.... but to be clear, also don't be afraid to make eye contact with your buddy. This is nothing to be ashamed about and in fact, feels less shameful if you two can look at and talk to each other while you're stroking your cocks.
And it's that easy! I'll cum on my stomach and my chest. I'll wait for him to cum if he hasn't already (which is fun to watch), then I'll just stand up, pull my shorts completely off and walk off into my room with a "gotta shower this off!"
And again -- to this day, the guy is still a good friend who has continued to hang and jo with me and others on occasion under similar circumstances. It can be a very natural, masculine and enjoyable thing if approached in a really chill way.
