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How Can I Make a Guy come in His Boxers?

I've been with my boyfriend for a while, and I am ready to start moving things along sexually for us. We are both virgins. and don't have a clue what we are doing. Up until now we have gotten to making out with both of us topless, and now I want to advance to below the belt.

Last weekend I started rubbing him over his boxers and with pants off, and while he guided me and said he enjoyed it and was close, he just wasn't able to cum.

I want him to enjoy himself, but I really have no idea what I am doing... I don't want to go yet to skin on skin contact, so how can I make him come over his boxers? Also, in what position should I be for my comfort and his pleasure?
How Can I Make a Guy come in His Boxers?
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