Sexual Relationships
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How to make him cum with underwear on?

So my boyfriend and I want to wait before we begin to have sex or oral sex or actually any means of sexual activity involving touching on the bare skin. I know it may seem weird but j guess we just want to wait. Anyhow, I want to know how I can pleasure him on top of his underwear? Like to the extent where he cums. I want to prove to him we can still do this and make it feel amazing. So please, desperately in need of help. Remember, I don't want to go into his underwear but I really want him to cum. Another question I have is, when j grab my boyfriends penis (with underwear on) occasionally I can feel it like twitch-throb like it moves like something's moving through it I guess. Why does this happen and what does it mean? (My best guess is the blood flow) but does it have anything to do with how he's feeling? Anyways, thank you :)
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Most Helpful Guys

  • You can give him a HJ through his underwear. That's where everything starts. You do NOT want movement between cloth and skin (chafing). So lay his hard cock flat toward his tummy and stroke rapidly with firm pressure with a flat hand so his underwear doesn't move. Be sure the waste band is above him so it contains the cumshot. Going skin to skin will be so much better. You can milk him then. The throbbing can be heartbeat as his boner grows. It inflates from blood pressure. It can also be a voluntary response to pleasure, pulling up like a girl Kegeling. I do that during a BJ. It's like I can feel her sucking deeper.

  • Here is a suggestion that I haven't read yet...

    What you could do is sit across from one another naked and watch each other masturbate. You could both sit Indian style with your legs criss-crossed. Talk dirty to him and play with yourself and allow him to do the same.

Most Helpful Girls

  • that is a tough question... i understand not wanting to have intercourse, but if you are willing to make him cum, i dont see the harm in at least giving him a handjob. You wouldn't want him to ruin his underwear, would you, and i'm sure it will not feel comfortable getting an erection or cumming in such an enclosed space for him.

    Other than that, you can just do dirty talk and make hi jerk off, but, to me that's lame. I need physical contact. But i respect your stance...

  • my boyfriend was cumming all over his boxers when we weren't having sex yet just from making out with me and grinned his dick on my vagina xD
    you can try that.

  • It's his muscles contracting to your touch.

    Just curious, why are you happy to wank him off through his pants but won't touch him?

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What Girls & Guys Said

1 11

  • Pole dance? Or play with your self amd make him watch it... more intensive it gets, he will go for it 😂

  • Why do you feel you need to have oral sex?

  • Just massage the tip through his ubderwear, works best with tighter fitting ones like boxer briefs or briefs, or put your hand inside and stimulate him gently, it can feel real good, my girlfriend use to do that
    Sometimes, sure it gets sticky and wet, but i have never ruined a pair of underwear from vuming inside them.

  • i think grinding can make him cum.. but if you really want this then why no give him a handjob?

  • If he wears loose boxers you can give him a handjob with them on but it'd be much more enjoyable for him if you let him take his underwear off

  • Grind on him bit the cloths against the head of his penis might stat to hurt. You should just pull it out and give him a hand job if you are comfortable enough seeing it and touching it

  • For Christ's sake at least give him a handjob.

  • If his penis is twitching you're doing the right thing. You little tease.

  • Just in case so you don't get your feelings hurt, I feel like you should be warned that some guys will not cum with their pants on. It feels amazing, but just doesn't produce the same sensation that makes me ejaculate.

  • Lap dance (filler)

  • This is a relashionship I need we're we can take I slow like this I have a lot of trouble with being touched sexually for reasons and it makes things really tuff bu tho sounds really nice and would work for me

  • This will probably lead to doing more than what you are planning, probably actual skin touching, and sex. If you want to wait just wait.

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