On the hotness of prostate play

One afternoon last spring, I was messing around in bed with someone I was seeing at the time. Let’s call her Daisy. Daisy’s big thing was orgasm denial; it was a kink she’d only just started exploring, but she got off on it in a way I found incredibly sexy, and as a result I was an enthusiastic participant in her various experiments.

For her part, Daisy liked the fact that I could exercise that sort of control – or maybe just that I was willing to do so while she played with me. I could spend a couple of hours fucking her, then get up and struggle back into my jeans while she lay on the bed and stared at my twitching, straining cock. I was happy to edge in front of her, bringing myself closer and closer as she made herself come repeatedly with a vibrator, then stopping the second she decided she’d seen enough.

Sometimes I’d go without an orgasm for a few days before we met up, and those were the sessions that really brought out her inner sadist.

“How badly do you want to come right now?” she’d ask, her fingers curled firmly around my cock, or her cunt squeezing it with every thrust. I’d grit my teeth and stare at the patterned wallpaper above her bed, my stomach and arse tensing with the effort of holding back.

Daisy liked those visual cues, those little signs of distress, and she would find ways to intensify them. On one occasion, she smiled down at me, tightened her grip on my cock, and whispered “you can come now” as she slowly pumped her hand up and down. It was only when I started to push my hips up to meet her, my cock sliding through her fist and the white noise in my head fuzzing out conscious thought, that she opened her fingers and sat back with a smug grin on her face.

“Just kidding,” she said, and licked the pre-cum off her fingertips.

Anyway, back to that afternoon last spring. We were in my bed this time, and Daisy had two fingers jammed in my arse. Her other hand played lazily with my cock and balls, but most of her attention – and increasingly mine too – was focused on the way my muscles clenched around her each time she pushed in a little deeper, as if they were encouraging further exploration.

It was the first time we’d tried any focused anal play, and I realised very quickly that Daisy knew exactly what she was doing. There was nothing tentative or random about the way her fingers curled up into me, and she clearly wasn’t trying just to fuck my arse.

“You like that, don’t you? You like it when I press….just…there…”

And all I could do by that point was nod. Pretty much all of my previous experience of prostate stimulation had been trial-and-error solo prodding with one of my toys; to have someone else massage that part of me so casually was intense in a way that suddenly made it hard to breathe, let alone speak.

As Daisy continued to work her fingers inside me, I lifted her other hand away from my cock, scared that if she kept touching it I wouldn’t be able to hold back. The drop in pressure, in the tingling, aching sensitivity, lasted a matter of seconds. If she picked up on the change in my breathing, on my sudden helplessness, she certainly made no allowance for it; instead she just flexed in and out, pressing the tips of her two fingers against my prostate and kissing my lips, muffling my weak sounds of protest.

Until that afternoon, my willpower with Daisy had always been top-notch. Since we’d started playing around with denial, I’d never come during one of our sessions, even after hours of her own special brand of provocation. Even when I’d gone the best part of a week without an orgasm, and it was just about literally the only thing I could think about. But with her fingers inside me like that, all my self-control vanished. I knew it was going to happen – could feel it building in a way that I’d only rarely experienced before then – and for the first time with Daisy I said and did nothing to stop it.

Maybe a part of me didn’t quite believe that I could come like that, with absolutely no cock stimulation, or maybe I thought she’d ease off when it became clear that I couldn’t do so myself. I don’t know – at that point everything got pretty blurry, and I barely had time to gasp “I’m coming” before it happened.

At the last moment she realised what was going on, and forced her fingers hard inside me, moving them back and forth to the rhythm of my spurting cock, as it shot cum all over my stomach. I was going crazy, overloaded with sensation and desperate for her both to stop and to really really never stop; in the end I grabbed for her wrist and she took the hint, easing her hand off my arse and rolling over to look for tissues.

That remained the only orgasm I had with Daisy. We stopped hooking up a short while later, after a couple of more controlled attempts at prostate play, and I went back to my butt plugs and other anal toys. Every now and then though, the memory of that afternoon would bubble up to the surface, and I’d have to make myself come pretty much immediately – something about the thought of her fingers working in and out of my arse is just impossible to resist, in the same way it was when she actually had them there.

Orgasms triggered by anal penetration are different in a way that’s actually not easy to describe. As they build up I feel constantly like I’m about to come, or even that I am coming, but without quite getting to the point of full release. It’s agonising and glorious and overwhelming all at the same time, and when I do finally push past whatever’s holding it back, there’s nothing that quite compares to that first rush of energy flowing out of my body.

It wasn’t until this week though that someone else touched me in the same way. Again it was unexpected, and this time the prostate stimulation was accompanied by her soft, warm tongue on my cock, and her lips moving up and down it. I knew right away that I was in serious trouble; at first I tried to fight it, but then those little surges of pleasure started, and with her mouth over me I suddenly couldn’t tell whether I was coming or not.

That disorientation was perhaps responsible for me yanking her up my body, onto my cock. Either way, it took no more than another 30 seconds before I really was coming, unstoppably and with one arm around her torso, clutching her tight against me as I pushed my cock deep inside her.

Having got back into bed expecting a long, lazy afternoon fuck, the urgency and intensity of that orgasm was the best kind of surprise. Ever since then, I’ve been thinking about her mouth and fingers, working together on my cock and arse, but also about the similar effect prostate play had on me with Daisy last spring.

Given how much I enjoy anal penetration more generally, I’m surprised by how reticent I’ve been about initiating or asking for that kind of stimulation. That’s perhaps because it requires the sort of anatomical explanation or guidance that can feel a little jarring in the heat of the moment – “no, a little more to the…yes, like that, only deeper…ouch, too much, too much” is pillow talk I maybe try to avoid with more casual partners – but I think it also has something to do with how I tend to want anal play to work psychologically. I want to feel like the other person is in total control of me, and that can make asking for it weirdly difficult – or confusing, at least.

I don’t know. What I do know is that having your prostate touched and massaged in that way is something every guy should try at least once. For my part, I certainly don’t intend to let another 10 months go by before I ask for it again.