Jerking with friends...

[AWSUMguy]

How do I go about it? I'm not gay, I'm just curious. do I ask? If so, how. When and where?

[Steddy95]

Have a sleep over. Play truth or dare and start off with mellow things and then ask's truth's like 'how big are you?' or dares like "i dare you to feel it..." more than likely he'll go along with things onc eyou get things rolling. Good luck.

[senior.2013]

Ease yourself into a conversation while at someones house. Maybe bring up some porn and ease into it. Dont be too bold and say "Hey, whip out your dick." or anything along those lines, because that will come off weird.

[Stronger]

Try talking along the lines of topics above but don't rush into it or force him to do it, if he doesn't want to make him. Should he feel uncomfortable, drop it

[Xandle]

Just start by doing something normal like playing video games, and get chatting. Maybe start talking about what girls in your school you think are hot or something similar like celebrities. Then say something like "I haven't had a wank for ages, do you masturbate?" and then if he says yes then just casually ask if he wants to join you. You just need to say it really casually... Also make sure that he would be into that sort of thing. If it's blatantly obvious that he wouldn't do it, then don't try. Good luck!!