How Can I Make a Guy come in His Boxers?

[Anonymous]

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?

[Jeppi]

I guess it depends from guy to guy, my girlfriend usually rubs me and massages my balls through my briefs, and ask him how it feels, just continue doing that, maybe putting your hand inside his underwear and jerk him off faster and faster, be sure it is still pleasant for him. It could take 5-10 minutes for me to cream my underwear, but when i do, it feels gr8, i dont mind the mess and my girlfriend seems to like it too.

[Anonymous]

Stroke his dick with your hand. It'll be easiest if you reach into his boxers and rub his penis directly. Otherwise, have him lay back and use one hand to gently massage his balls and the area just behind them while you stroke his dick with the other hand. Pay special attention to the area right where his head meets the shaft on the underside of his dick. Good luck!

[NewYorkCity]

Cumming in his boxers is going to be such a mess don't do it. Give him a BJ but you have to ether swallow it or give him napkin so he can finish him self off. I'm just telling you right now, jezing into pants is not cool, it is sticky smelly feeling and sensation after which he has to get brand new boxers and take a shower.

[sirspauldo]

Either dry hump each other or grind on him.

[DodgersGM]

It can be very difficult to make a guy come like that. Lots of dudes don't even orgasm frequently from handjobs, so seriously don't feel bad if it doesn't end in him cumming. Just focus on having fun and making it a pleasurable experience for both of you. The rest will follow.

[Dandeus]

If I were in his position I'd just prefer to wait until you're ready for skin to skin. Having dried come in your clothes and in your pubic hair is a huge pain in the ass. If you want to move beyond what you're doing, I suggest masturbating in front of each other without touching.

[the-man-who-knows]

You can use your hand and jerk him off through the boxers. you could give him a lap dance with the boxers on grinding your ass on his cock.

[CRamos3]

dry hump him...get on top of him (fully clothed) and grind on him through the rhythmic motions of sex...grab the back of neck and pull him close to you...he'll bust a nut in no time at all...