Ask a man if he wants a prostate massage and you will usually get the same two reactions, in this order: a nervous laugh, and then a question about what it says about him. The answer is nothing. The prostate is a walnut-sized gland every man has, sitting a few centimetres inside the anus, and it is packed with nerve endings. Stimulating it has no more to do with orientation than stimulating a clitoris does.
What it does have to do with is intensity. Men who let their partner explore it usually describe a deeper, longer, full-body orgasm - and often the first "hands-free" finish of their life.
This guide covers how to do it properly - hygiene, lube, position, how to actually find it - and 15 real dares from the NaughtyApp database, written out in full, from a first touch on the outside to two that end in an orgasm. All of them are her doing it to him.
Before you start: the boring part that makes it good
- Nails short and filed. No sharp edges. The tissue inside is delicate - this is the single most common cause of pain. Disposable gloves are a good idea and make cleanup trivial.
- A shower, and an empty bowel. A normal bowel movement a couple of hours before and a proper wash is enough. Nobody needs an enema for a finger.
- Lube, far more than you think. The anus produces none of its own. Use a thick water-based lube and reapply often; if you are using silicone toys, water-based is the only safe choice.
- Nothing goes from his anus to her vagina. Not a finger, not a toy, not without washing first. This is the one rule with a real health reason behind it.
- He is in charge of the pace. "Stop", "slower" and "more" are the entire vocabulary. Pain is always a signal to stop, never something to push through.
How to find the prostate
With him relaxed - on his back with his knees up is the easiest position for her - she slides one well-lubed finger in slowly, up to about the second knuckle, with the fingertip pointing toward his navel. Two to three inches in, on the front wall, she will feel a rounded bump, firmer than the tissue around it. That is it.
The motion that works is not thrusting. It is a slow "come here" curl of the fingertip, or steady pressure held and released. Think of pressing a doorbell rather than rubbing something. Most men feel an odd urge to urinate for the first minute - that passes, and it is normal.
Start outside. Massage around the entrance for a while before anything goes in. The muscle has to relax on its own, and it will not be rushed.
First contact (levels 2-3)
Outside, then one finger. Short, and nothing else happening at the same time.
- Outside only. She orders him to lie face down and spread his buttocks. She massages around his anus for two minutes - without touching anything else.
- Tongue and one finger. While she licks his testicles, she slides a finger into his anus. Sixty seconds.
- Clamped, and nothing for his penis. She clamps his nipples, slides a lubricated index finger into his anus and gives him a prostate massage for a little over two minutes - and does not touch his penis at any point.
Learning the technique (level 4)
This is where she finds out what actually works on him. Every one of these is a different combination of mouth, hand and fingertip.
- Circles, changing. She starts masturbating him very slowly, then runs her fingertip around his prostate in circular motions - changing the pressure and the speed, and staying with whatever combination works best, for two minutes.
- Frenulum only. He lies on his back. She holds his penis tight and pulls it so the head is fully exposed, then slides a finger into his anus and massages it while licking his frenulum. No stroking - just the tongue on the frenulum and the finger on the prostate, for 100 seconds.
- The full combination. He lies on his back. She holds his penis tight so the head is exposed, slides a finger into his anus and massages it while she gives him a blowjob, for 100 seconds.
- Just the head. He lies on his back with his legs apart. She puts his glans in her mouth and does nothing but run her tongue around it, while massaging his prostate with a finger, for two minutes.
- Deep, and completely still. He lies on his back. She takes his penis as deep into her mouth as she can and then holds perfectly still - no tongue, no movement - while she slides a finger into his anus and massages it, so all he feels is the heat of her mouth and the pressure from the inside. Just over two minutes.
- Three places at once. He lies on his back with his legs apart. She strokes him very slowly while licking his testicles, and slides a finger into his anus to massage his prostate at the same time, for two minutes.
- How long can he last? He lies on his back. She finds out how long he can go without coming from prostate massage alone - no touching his penis at all. She can stroke his nipples while she does it.
She takes over (levels 3-4)
The same thing, with an order attached. This is where prostate play and femdom overlap.
- Spanked and opened. She orders him to lie face down and combines light spanking on his buttocks with a prostate massage using two fingers - making him moan and beg for more, without letting him come.
- Push back. She orders him onto all fours on the floor. She works two lubricated fingers into his anus and then a third, opening him slowly - and orders him to push back against her hand.
With a toy (level 4)
- Two motors, swapped. He gets on all fours with the Edge inside him. She swaps between the prostate motor and the external one every 30 seconds, stroking his penis to the same beat, for three minutes.
The Edge is a prostate massager with two separate motors, one on the prostate and one on the perineum, both app-controlled. A finger works perfectly well - the toy just frees her hands. The link is an affiliate link: if you buy through it, we may earn a commission at no extra cost to you.
All the way (level 5)
Two ways to finish. Both end with him coming with her finger still inside.
- While he is inside her. She lies on her back and spreads her legs, and he penetrates her. While he does, she stretches her arms around him and slides a finger into his anus, massaging it until he comes.
- Come here, faster. She starts stroking him very slowly, then slides a lubricated index finger into his anus and curls it upward in a "come here" motion toward his navel. She keeps repeating it, gradually speeding up as the pleasure builds, until he comes.
The taboo, briefly
Most of the hesitation around this has nothing to do with the act and everything to do with what men think it means. So, plainly: the prostate is anatomy, not orientation. Straight men have one, gay men have one, and what a man enjoys having touched says nothing about who he is attracted to. The only thing that changes when a couple tries it is how good his orgasms are.
If it turns out he likes handing over control as much as the sensation, the femdom guide takes that further. For everything else anal, including her turn, see the anal challenges for couples, and the Lovense toys guide covers the Edge in detail.
FAQ
Does liking prostate massage mean he is gay?
No. The prostate is part of male anatomy, and enjoying stimulation there says nothing about sexual orientation - exactly as enjoying oral sex says nothing about it. Plenty of straight men have their strongest orgasms this way.
Does a prostate massage hurt?
It should not. Pain almost always means one of three things: not enough lube, going too fast, or a fingernail. Start outside, use far more lube than feels necessary, and let him set the pace.
How do you find the prostate?
One lubricated finger, palm up, about two to three inches inside, pressing gently toward the navel. You are looking for a rounded bump that feels firmer than the tissue around it. Use a slow "come here" curl rather than thrusting.
Can he orgasm from prostate massage alone?
Many men can, though it usually takes practice and patience - and it feels different from a normal orgasm: slower to build, deeper, and sometimes without much ejaculation. Dare 10 above is built around exactly that.
Do we need a toy?
No. A finger and plenty of lube is all you need, and it is the best way to learn what he responds to. A prostate massager like the Edge is worth it later, mostly because it frees her hands for everything else.
Let the app run the session
These 15 dares come from the anal and femdom categories of the NaughtyApp dare database - the app has hundreds more, and it picks them for you.
- 4,500+ dares across more than a dozen categories, from first-touch to level 5.
- Five levels, in order. Start where you are comfortable and climb only when you both want to.
- A built-in timer for every timed dare, so neither of you has to watch the clock.
👉 Download NaughtyApp free and start with dare 1 tonight
Tried it? Tag us: #ProstateMassage #PSpot #CoupleChallenge #CoupleGames
