Sex Advice: How to Overstimulate Your Man Until He Begs You to Stop

Advanced Techniques for Intense, Controlled Pleasure, from our sex positions and techniques collection

Dear Deni,

My boyfriend and I have great sex, honestly; no complaints there. But lately I've been craving something more intense. I want to push him past what he's used to, past the point where he's just enjoying himself and into the point where he's actually begging. I've heard about "overstimulation," but I don't really know what that means in practice or how to do it without it just feeling like I'm doing too much. How do I actually take him there?

Wanda

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Dear Wanda,

Honey, sit down, pour yourself something, and let's talk.

I've written a lot of columns over the years. Letters about first times, about dry spells, about the guy who wouldn't stop talking during sex (we'll get to him another day). But today I want to talk about something a little more advanced. Something for the women who've already made him come. Who've made him moan, made him scream a little. It's routine now, and honestly? Routine is beautiful in its own way. I've had routines with men I loved that I wouldn't trade for anything.

But some nights you don't want routine. Some nights you want to break him a little.

That's what I'm here to teach you today.

What Overstimulation Actually Is

It was never about making him come harder. It's about making him feel everything.

I learned this by accident, decades ago now, with a man who begged me to stop while pulling me closer at the same time. That contradiction taught me more about male pleasure than any book ever did.

You take him right to the edge. Then past it. Then further past it, even when he swears he can't take one more second. His body stops knowing what to do with itself. He's shaking. Gasping. Completely, deliciously out of control.

Here's my secret, the one I want you to remember above everything else in this letter: keep going after he comes. That's the moment. That's when every nerve ending is standing at attention, when the lightest touch feels like a current running through him.

I want to be very clear with you, because I take this seriously: the point was never to torture him. It's to show him a kind of pleasure he didn't know his own body could produce. There's a difference, and a good woman knows it.

The Slide

This one's simple. And devastating. I've never met a man who could stay composed through it.

When you're on top, don't take him inside you yet. Instead, slide your wet pussy along the length of his dick. Let your lips grip his shaft. Slide up and down, slow, like you've got nowhere else to be tonight. Let him feel every inch of you without ever letting him inside.

The friction alone will undo him. He can feel exactly how wet you are. He can feel every contour of you pressed against the most sensitive skin on his body. And that anticipation, the "not-yet" of it, that's what really drives him crazy. It always has been.

He'll already be right at the edge before you've even taken him in.

One thing I always tell the women who write to me: look into his eyes while you do this. That eye contact turns a technique into an experience. Don't skip it.

The Bottom Lick

This is the one that'll make him shake, and I mean genuinely shake.

When you're going down on him, forget the tip for a moment. Focus on the underside, right at the base, where his shaft meets his balls. Lick it. Slowly. On purpose. Like you know exactly what you're doing, because after today, you will.

That spot is packed with nerve endings, and most women walk right past it. When you give it real attention, you're touching a place he probably didn't even know could feel that good.

Watch his legs. They'll shake. His hips will start to buck without his permission. He'll grab your hair and pull you in closer, and that's how you know it's working.

Pair it with gentle suction. Tongue and suction together is a combination I've never seen fail.

The Edge and Keep Going

Bring him right up to the edge of orgasm, and then stop. Completely. Let him cool off for a moment. Then start again. Bring him close again. Stop again. Do this three, maybe four times, however long your patience holds out.

When you finally, finally let him come, don't you dare stop. Keep your mouth on him. Keep your hands moving. Keep that rhythm going right through his orgasm and past it.

He'll be so sensitive that every single touch will feel like fire. He'll beg you to stop. I promise you, sweetheart, he won't actually want you to.

Here's the line I've told every woman who's ever asked me this: when he says "stop," that's usually your sign you're doing it exactly right. Trust him to actually tell you if it's too much, and trust yourself to listen when he does.

The Overstimulation Finish

This is the one for when you want to completely wreck him. I don't use that word lightly.

Once he's finished coming, keep touching him, but change everything about how. Lighter now. Slower. Let every nerve ending in that area fire off at once.

Right after orgasm, his dick is almost unbearably sensitive. A stroke that would normally feel nice now feels like a lightning bolt straight up his spine.

He'll squirm. He'll beg. He might even try to push your hand away. He won't really mean it. If he's too sensitive to touch directly, move to his inner thighs instead. The sensation travels there too; he'll still feel every bit of it.

The Perineum Press

While you're going down on him or using your hands, press your fingers gently into his perineum, that spot between his balls and his ass. Apply light, steady pressure. Circle it. Add a little vibration if you're feeling generous.

What you're doing, without him needing to know the anatomy of it, is stimulating his prostate from the outside. It adds an entirely new layer to what he's already feeling.

His orgasm, when it finally comes, will be deeper. Longer. More intense than he's used to.

Combine this with the overstimulation technique I already gave you, and honestly, he won't know what hit him.

The Riding and Grinding Without Penetration

This, to me, is the ultimate tease. I saved it for near the end on purpose.

Get on top of him. Slide your wet pussy along his dick, same as before, but don't take him inside. Just grind. Let your lips grip his shaft. Let your wetness coat him completely. Move a little faster this time than you did with the slide.

He can feel everything, the heat, the wetness, the pressure of you, but he's not inside you. And that anticipation is its own kind of torture, the good kind.

He'll get desperate. He'll beg you to finally let him in. And when you do? Don't expect him to last long. That's the whole point.

The Finishing Move

When you're ready to bring the whole thing home, go out with a bang.

Bring him right to the edge one more time. Then past it. Way past it. Keep going right through his orgasm, and keep going a little after that too.

He'll be completely wrecked by the end of it. Shaking. Gasping. Barely able to string words together.

And when he's finally, truly done? Kiss him. I mean it. Men need that connection just as much as we do, and it's the part too many of us skip when we're focused on technique.

So…

Overstimulation was never about cruelty, and if you take one thing from this letter, let it be that. It's about showing a man pleasure he didn't know existed in his own body.

Master the tips I gave you, and you're not just making him come anymore. You're making him lose control completely.

You're making him beg.

Until next time,

Samarel, in the spirit of Deni

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Deni answered hundreds of letters like Wanda's over the years. If you'd like more of her honest, no-nonsense advice on sex techniques, her collected letters are in 'Dear Deni: Sex Positions and Techniques'

Disclaimer: The information contained herein is for educational purposes only, and is not intended as a substitute for the diagnosis or treatment of any health problem, whether it be physical or psychological. 'Dear Deni' assumes no responsibility for how this material is used.