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I would think it'd be a lot better to not ask him and while you're making out or whatever, slowly put your hand on his leg and slowly move it up towards that area, and just keep slowly progressing until you unbutton his pants and put your hand in. If he is uncomfortable with it, he'll tell you, just don't go to fast, that could ruin it. Good luck!
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Handjob questions
I've been wanting to give my boyfriend a handjob. How do I give him one? How to I bring it up that I want to give him one?