Taking His Cherry (Part 1)

Why I love pegging a man with my strap-on for the first time -Part 1 of 2


Charli Dixin

4 min read

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 cherry 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 at first with a generously lubed finger, sliding in and out, feeling that tight ring of muscle unused to being penetrated soften and yield to my finger as it probes 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, 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...that elicits an even deeper moan, an arch in your back, as you raise your hips and begin to rock back and forth along my finger, the tight ring of muscle beginning to relax more and more as I push with a little more pressure.

"Gooood boy, ohh, that's the way, 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? 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 assertation 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 index 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. "Dont be shy now baby you know you want this. Can you wriggle your toes for me a little?" My secret little Jedi mind trick works its magic here as always and you open up to let both fingers sink all the way into you, both of us exhaling with deep sighs of pleasure, the breath you didn't know you had been holding escaping you. Your hips bucking back and forth to meet the rhythm of my fingers sawing in and out as you begin to lose yourself to the pleasure 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?...I think you must be just about ready to take my cock now don't you baby...Mmm feels like you are, let's see if we can get it into you, see how you like being properly fucked, yea?"

"Ahhh....yea...fuck me..." Your gasping response.

A couple more twisting strokes of my fingers in and out of your now eager and pliable opening, before I reluctantly draw them out in order to reach for my harness, a simple black leather piece with a soft inner lining, o-ring at the front to hold a toy, and d rings to tighten the straps along my hips and buttocks.

Stepping into the harness and pulling it up and 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 and with a subtle upward curve to it, its perfect for the job at hand tonight. 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 at the front of the harness 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 ask, giggling a little at your eager compliance as you quickly reach for the straps, fingers fumbling slightly at first then pulling firmly till you've got all 4 tightened and the harness fitting snugly to my body. I keep eye contact with you as I stroke my hand up and down the shaft of my pink toy, 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 slowly 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 cocks touch briefly with the gentle bucking of my pelvis.

"Mmmm...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?"

...tbc in the next post ,
Charli xx

closeup photo of cherries
closeup photo of cherries