May 2025

His First Time

"Hi, I'm interested in being pegged...never done it before but your ad caught my eye..."

Out of all the text messages I get from potential clients this one is almost guaranteed to get an instant reply from me. It definitely gets an instant response from my body - call me perverted, but the prospect of taking a grown man's anal virginity thrills me that much it makes my pussy literally throb. Fuck, there's just something so hot about being the first one to fuck a man.

Opening you up slowly with lubed fingers, sliding in and out and feeling that tight ring of muscle, unused to being penetrated, begin to soften and yield. My fingertips probing gently inwards while I murmur words of encouragement, "Open up baby, that's a good boy, that feel good? Mmm, you like that don't you?"

Hearing your soft, sighing moans deepening into guttural masculine growls of assent, I push a little deeper. You push back to meet me, and feel the pad of my fingertip lightly stroke your prostate for the first time. This elicits an even deeper moan and an arch in your back as you raise your hips and begin to rock back and forth in rhythm with my finger sliding in and out. The tight, gripping ring of muscle begins to relax around the base of my finger as I curl it upwards for more direct contact with your prostate, my teasing flickers of touch increasing to a firm yet gentle pressure as your body opens up to me, hungry for more.

"Gooood boy, ohh, that's the way baby... how does that feel, feels good doesn't it? Mmmm you feel SO good inside, so soft and hot and tight, you're going to love feeling me fuck your ass aren't you baby? Mmmm yes you are....let me open you up a little more first, get you all nice and stretched and ready for my cock to fuck you... that's what you want isn't it? You want to feel me fucking you with my strap-on cock?"

A muffled moan of assertion, and a deepening arch to your back is all the response I need to know that yes, me fucking you is indeed what you want.

Fuck, it's what I want too. My pussy is dripping wet as I begin to work my middle finger in alongside the first, lightly pressing the pads of both fingers against your hole which is still slick with lube, but suddenly shy, tightening up again, and you squirming away from my fingers.

"Don't be shy now baby, you know you want this...Can you wriggle your toes for me a little?"

My secret Jedi mind trick works its magic here as always and you open up, letting both fingers sink all the way into you. Both of us exhale with deep sighs of release, the breath you didn't know you had been holding escaping you. Your hips buck back and forth to meet the rhythm of my fingers sawing in and out as you begin to lose yourself to the feeling of being penetrated.

"Fuuuuck yes baby, mmm, fuck yourself on my fingers, just like that, ohhh yes you sexy, dirty boy, you fucking love it don't you? Think you must be just about ready to take my cock in there now, yeah? Mmm feels like you are, let's see if we can get it into you then, see how you like being properly fucked in this virgin hole, yeah?" "Ahhh fuck... ....yea.. ....fuck me...!"

A couple more slow, twisting strokes of my fingers in and out of your now eager and pliable opening, before I reluctantly draw them back in order to reach for my harness. It's a simple black leather piece with a soft inner lining, and d-rings to tighten the straps that run between my legs and around my hips and buttocks.

Stepping into the harness and pulling it up over my thighs, I look at you and smile, my eyes following your wild, excited gaze to the dildo at the top of my bag of tricks, the toy I've chosen to take your cherry with tonight.

Hot pink in colour, it's 7 inches in total insertable length, with a slender, smoothly tapered tip that thickens gradually to a decently girthy base. With a subtle upward curve to it, it's perfect for the job at hand. Big enough to hit the sweet spot - you'll definitely know when you've got this baby in you, but not so big it'll cause any discomfort or limit me from fucking you properly - really giving it to you, the way you want it. The way I want to give it to you.

I take the toy by the base and thread it through the o-ring from behind, turning it slightly so it juts out proudly, curving upward toward my stomach, just like a real - and really erect - cock, albeit a vividly bright pink one.

"Help me tighten my harness, won't you?"

I barely have to finish asking, giggling a little at your eager compliance as you quickly reach for the straps. Your fingers fumbling slightly at first, then pulling firmly, till you've got all 4 straps tightened and the harness fits snugly to my body.

I keep eye contact with you as I stroke my hand slowly up and down the shaft of the pink dildo, my hips beginning to undulate as my excitement grows with yours, the lustful, wanting, hungry look in your eyes no doubt reflected deep in mine.

With my other hand I grasp your rigidly hard cock and stroke up and down in a matching rhythm to the hand sliding up and down my toy, pressing my lower body up against yours and my toy right up next to your cock, letting both of 'our' cocks touch briefly with the gentle bucking of my pelvis.

"Mmmm...Now turn around and lie face down...lift that butt up over the pillow, yes good boy, just like that, nice and easy access for me... Think you're ready for me to fuck you properly now?"

Your hips shift upwards, and your gorgeously rounded ass perfectly presented to me on its pillow looks so good, so perfectly fuckable.

Lathering the toy with a generous coating of lube, I lean forwards towards you and gently press the head of the dildo against your hole. Gripping it at the base I ever so slightly begin to move the toy. Not penetrating you or pushing in at all yet, just teasing you with it, lazily dragging the tip over your hole and drawing slow, soft, slippery little circles. I'm enjoying taking my time, letting your imagination do the work as you feel it touching you and knowing that I'll have it deep inside you very very soon. Inside your ass, fucking you, taking your anal virginity... I know where your mind is going, that you're wanting this so much that you're almost ready to beg me for it, but I want to draw out this moment of exquisitely torturous anticipation a little longer yet.

I slide the length of the lubed up toy slowly up and down in between the cleft of your buttocks, priming you with yet more lube, till I've got you all nice and wet and slicked up, all ready for me to slide my strap-on cock into.

I pause for a second for you to let out the breath you've been holding since the toy first touched your hole, waiting for you to relax a little again.

I can feel the dripping wetness between my legs and the hot pulsing of my clit as I lean in toward you and press the head of the toy to your slippery hole. Leaning in deeper and holding the toy at the base I hear you inhale sharply as the first inch of the dildo sinks into you.

I ease off here and wait a moment for you to let your breath out and relax again, before leaning my hips forward again, letting my body weight do the work as I watch my silicone cock slide another inch inside you, the tapered end beginning to widen a little along the shaft and stretch out your tight pink ring. Fuck, it looks good.

You moan softly, and I ask if you're ok, ask if I can go deeper? You nod in response.

"Push back on me, show me how deep you can take it for me then."

Your eager compliance as you back up on the toy and easily take in another 2 inches without complaint elicits my genuine praise.

"Ohhh gooood boy, mmmm yesssss, look at you, you want it all the way in already don't you? So hungry to be fucked...you want a little more, don't you? Think you're ready for all of me now?" "Yesss... Deeper."

You growl through gritted teeth, and push your ass back to me as I hold you by your hips and lean further into you. Watching your no longer virgin asshole engulf the last 3 inches of the dildo, feeling your tight internal muscles pulling at it, swallowing every bit inside you like a sucking, hungry mouth, is a sight to behold.

"Fuuuuuuuck"

You groan as I shift my position ever so slightly until my pelvis rests right up against your buttocks, pulling you into me by your hips at the same time, letting you know just how deep I've buried my strapon cock in you.

"That's all of it baby, you've got this cock in you as deep as it gets... You took it so good too, I think you're ready to feel me really fuck you with it now, yeah?"

Your "fuck yes, fuck me, I wanna feel you fuck me..." wouldn't have been necessary, since you've already begun to buck your ass back and forth along the dildo eagerly.

"Well you need to stay still and let me do the fucking for now then."

You immediately comply, ceasing all movement as I dig my fingers deeper into your sides to hold you in place, then ever so slowly roll my hips back till only the last couple of inches remain in you. I pause for just a second here then push back in, almost all the way, before withdrawing again to almost all the way back out, and then again, in and out.

And in... Out...In...deep this time, sinking the toy all the way back inside you, the upward roll of my hips and the weight of my body giving power to my thrust so your body shudders slightly under the force of it.

"Fuuuuuuuck"

Your breathless gasp. Out. In. Out. In. Picking up the tempo a little, finding a natural rhythm, I feel you relaxing, surrendering to physical pleasure, as you start to push back to meet me on my inward strokes. You're still gasping out "fuuuck"s, breathing raggedly.

"Fuuuuuuck. Fuuuuuuuck. That feels so fucking good....fuuuuuuck"

I can feel what I'm doing has you close to cumming already. How you're tensing up and your breath is hitching, building up to what I know will be the most explosive orgasm you've had in your entire life. And I want to see it, want to watch your face while I fuck the cum out of you. I slow, then stop my movements, and steadily withdraw the toy from your ass, to your immediate cry of "ahh fuck!...don't stop!"

"Turn over, I want you on your back, I want to watch you when you cum."

You're so eager to comply and have my cock back inside you, you almost fall off the couch as you leap up and spin over onto your back. We giggle a little, then I pull your legs up and apart and shift position till I'm ready for re-entry, holding the toy in one hand and lightly grasping your cock in the other as I ease back into your waiting hole.

Your sigh as you feel the dildo sliding steadily inside, opening you up yet again, your cock twitching in my hand. Only semi hard despite you being so intensely aroused, all your attention is focused elsewhere right now, on these delicious new sensations you're feeling as I start to fuck the head of the toy in and out. The nerve endings tingling as it stretches your tight hole open again. The exquisite satisfaction of my strapon cock filling you up as I slowly sink all 7 inches all the way back in.

In. Out. In. Out. Your prostate swollen and beginning to pulse as the head of the dildo rubs back and forth over it, an almost unbearable pressure, one that you've always craved to know, building within you with every deep stroke. I grip your cock a little more firmly and start to stroke up and down the shaft in rhythm with my fucking. Which is picking up the pace again. A little bit faster... and harder. In, out. In, out. My hand, sliding up and down your cock. Up, down. Up, down.

"Mmmm yes baby... You're going to cum aren't you?" "Fuuuuuck yes I'm gonna cum... please...like this...ahhh fuck, fuck...that feels so fucking good in me, ah fuck don't stop, fuuuuuck yes..."

In, out, in, out, in, out. My hips slamming against your groin as I pound the strapon in and out of you, leaning in and up against your spread open thighs, as your leg muscles begin to tense. You're gasping now, eyes wild with desire as they lock with mine, your entire body quivering as the first waves of your orgasm begin to hit.

"Oh fuck yes baby, that's it, cum for me baby give it to me, let me fuck the cum out of you!"

"Aaaah" you hiss out between ragged breaths, eyes rolling back in your head. Not chancing on your muscles tensing up so hard you push the toy out, I wrap my free arm around one of your thighs and pull my body in towards yours, burying the dildo as deep as it will go in one final powerful thrust.

"Uuunnggggfffffhhh!!!"

Your deep, primal roar as your cock swells to its hardest. The hot, thick jets of a copiously large load of milky white cum begin to shoot out, long white ropes of it hitting your chest, thighs, the pillows behind you, yet more spilling over my hand wrapped around your cock, as your pelvis jerks up and down and you gasp and moan incoherently.

It's so fucking insanely hot to watch I'm almost right there with you, so turned on my body is primed for pleasure and on the edge of orgasm myself. I know I'll have more than one later thinking of this moment again when I'm alone...

"Fuck yes baby that is so fucking hot, look how much cum you just made for me, fuck!"

Your eyes flutter back open and you smile weakly at me in response, then throw your head back and groan loudly once more, as another wave takes over. Your body shudders, cock jerking, spilling yet more of your seed to dribble down over my hand as I loosen my grip. Catching my own breath, a bead of sweat rolling down from between my breasts to where I'm joined with you at the hip, I stay still for a few minutes, watching you ride out the full power of your first prostate orgasm. So powerful that with my strapon cock still buried deep in you I can feel each rolling wave rising and peaking through your body. The sexiest soft murmurs and moans are still escaping between your shaky gasps of breath as your muscles tense and relax, alternating currents of pleasure pulsing deep within you.

"Holy. Fuck. Fuck...that felt...so fucking good. I never realised..." "You could cum that hard?" "Yea or that it would feel so good...the whole thing... just wow...I can still feel it now...Fuuuck!" "I told you I'd make it feel good. You took it so good too, fuck, it was hot as fuck...good boy."

I withdraw the toy slowly and you exhale in a long deep sigh as it slides out of you, your body relaxing a little now, a shiver every few seconds as another ripple of physical pleasure hits and then gently subsides.

I lean in to kiss you. It's a quick, yet deep and passionate kiss, a kiss I hope conveys to you my gratitude, my pride, and most of all, how fucking turned on taking your anal cherry has made me.

There's nothing like being the first.