Taking His Cherry (Part 2)

The long awaited conclusion to my story of how I took his anal virginity....

Charli Dixin

8/6/20236 min read

2 red cherries on white textile
2 red cherries on white textile

"Mmm... Now turn around and lie face down on the bed... 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 now baby?"

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

Lathering the toy with a generous coating of slippery lube, I lean forwards towards you and gently press the head of the dildo against your asshole. 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. Sliding it up and down your ass crack 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 wait for you to let out the breath you've been holding since the toy first touched your asshole and you relax a little again.

I can feel the dripping wetness between my legs and the hot pulsing of my clit when I lean forwards 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 for me then" I instruct you.

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

Mmmm. 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.

"Fuuuuuuck" 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, yea?"

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.





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 "ajhh 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 the pleasure you're feeling as I start to fuck the toy in and out of your asshole. The nerve endings tingling as it stretches your tight hole open again. The delicious feeling of me filling you up as I sink it all the way back inside you.





Your prostate swollen and beginning to pulse as the head of the dildo rubs back and forth over it, an almost unbearable pressure that you've always craved to know building within you with every 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, stroking your cock. Up, down. Up, down.

"Oh fuck. Fuuuuuck" you groan as I thrust in and out of you harder, faster, letting my body weight add power as I start to really pound into you, your cock beginning to throb and swell in the tightening grasp of my stroking hand.

"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... Cum for me while I fuck your ass!"

"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.


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 moan softly once more, as another wave takes over and your body shudders, your cock jerking, spilling yet more of your seed to dribble down over my hand as I loosen my grip.

"Holy. Fuck. Fuck...that felt...so fucking good."

You finally manage to utter some properly formed words, shaking your head with a look of disbelief "I never realised..."

"You could cum that hard?" I smile.

"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, 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.