Well, first off, it's not gay. Only actual sex is considered gay. A lot of friends do this, and it's perfectly normal!
I don't have much advice since I've never done it. But, this is what I know.
Maybe you could invite him over, grab a couple beers, and some porn vids (If you're old enough to drink of course) and if he gets drunk, in combination from the hornieness from watching the porn, he might go with it.
It's worth a shot, because wheather he says yes or he says no, he probably will be too drunk to remember. I wish you the best of luck! (^^)v
How to masturbate with friend
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Well, first off, it's not gay. Only actual sex is considered gay. A lot of friends do this, and it's perfectly normal!
I don't have much advice since I've never done it. But, this is what I know.
Maybe you could invite him over, grab a couple beers, and some porn vids (If you're old enough to drink of course) and if he gets drunk, in combination from the hornieness from watching the porn, he might go with it.
It's worth a shot, because wheather he says yes or he says no, he probably will be too drunk to remember. I wish you the best of luck! (^^)v