Poolside Pegging

by Joanne Queenin March 22, 2017

Poolside Pegging

Congrats to Mistress Kay of My Kinky World for winning best BDSM in our Valentine's Fantasy Contest. Her three-way poolside pegging fantasy definitely left us hot and bothered!

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Clang! I pull the name badge off from around my neck and drop it unceremoniously onto the glass-topped table next to my chair. Enjoying the weekend at a kink conference with two of my play partners had been a fantastic idea. Both my submissives, we had enjoyed some spanking and orgasm torture scenes the night before, and we were looking forward to today's activities of relaxation. The room's humidity told me that something besides the leather dress I was wearing might have been more conducive to relaxation, though.

This afternoon, the three of us are enjoying one of the amazing features of this conference: a hotel swimming pool with no clothes required and no rules in place. Various people are strewn throughout the deep water including a couple that's having sex on one of the sides of the pool. A bit adverse to messing up our make-up and hair so early in the day, my female submissive and I sit, clothed, in the poolside chairs while we watch my male submissive swim leisurely around the pool without a strip of clothing on his body.

"How has the conference gone for you so far?" I inquire, the side of my leg touching her own as my hand rests upon the bare skin of her thigh. "Anything you haven't gotten to try yet this weekend?"

"I, well", she pauses, her eyes downcast. "Well, I've always wanted to enjoy strap-on sex. I tried it once with a crappy harness," she mumbles, "but I think it can be better. It kinda scares me, though. I don't really know what I'm doing."

My fingers trace patterns on her thigh as I reassure her about her fantasies. "Well, would you be open to trying? It's certainly a safe space here, and I can help you through it."

Her hand envelopes my own, and it's only out of the corner of my eye that I notice the quick nod of her head as her cheeks flush. "First, I want to see you naked," I start, and the short-haired brunette stands up and starts to quickly strip off her clothing – not wanting to displease me. First her top, exposing her thick breasts, and then the bra to go with it. The skirt comes off next to display her perfectly-fitting thong panties that showcase her curvy butt.

"You look wonderful", I praise, as I stand to wrap a hand around her waist and plant a reassuring kiss on her neck. With her clearly ready and willing to fulfill her fantasy, it's time to get the other half of this party ready.

"Come here!" With a raised voice and a quick glance at my male sub, he's quickly pulling his naked body out from the steps of the pool ladder, his biceps looking good this afternoon as he uses them to hoist his own weight. My call catches the attention of a few of the other pool-goers, but they quickly go back to their own play.

Dripping wet, standing exposed in front of me, my boy waits to find out why I've called him. Poolside on the tiled area right next to the large body of water, I crouch and pat the ground, and he sits. A firm push onto his upper chest, and he gets the idea, and it doesn't take long until he lays flat on the towel I've laid out for him. A quick ruffling through my toy bag next to our chairs reveals the Suction Hand Cuffs I was looking for. Used time and time again for any play near water, I love that each cuff firmly attaches to a large, powerful suction cup. I rejoin my boy, and his wrists are soon encased in the soft material of the cuffs. With the flat tiled surface underneath him, I firmly press the suction cups against the floor and watch as he's effortlessly restrained. Unable to hide, his entire body is on display to the entire pool, and more importantly: to us.

"Now, to get you prepared," I state, as I pull my attention back to my naked girl, and it's another trip back to the my toybag. My boy's eyes follow my form as I rummage through my packed duffel bag. The flash of red peaking out from between the sea of black leather leads me to what I need, and I pull out my "Flare" dildo and drop it onto the chair next to my bag. More rummaging and untangling, and my harness is untangled and ready for use. Black and red to perfectly match the erotic, sensual red color of the dildo, the harness is one of my favorites. With the lace-up corset detailing in the back and the soft material throughout the entire harness, it looks sexy - and feels comfortable while doing it.

Looking so nervous she's almost shaking as I pull the toys from the bag, I offer a reassuring smile. "Don't worry. This harness is really easy to put on. Here, let me help". Organizing the straps into neat piles at her feet, I place the harness on the ground and let her lean onto my kneeling form as I help her place her feet into the proper places in the piles of straps on the ground. "Now just pull up", I command, and I help her pull the harness up around her curvaceous, tempting hips. Kneeling in front of her bare body - only clad in my newest harness addition - I help her adjust the various black buckles for a perfect fit.

Bending over a bit to watch what I'm doing to her, my girl's hands rest on my shoulders as I finish with the adjustments. In the perfect position for more, I press my palm between her legs, pressing the harness against her sensitive place. Wasting no time, I wiggle the harness even more as I pleasure her. A soft sigh escapes her lips which brings a laugh to mine. I meet her eyes with a cheeky gaze as I unbutton one of the harness's O-ring fasteners to slip the seductive red dildo through the ring. Once slipped through the ring, I refasten the snap, and I sit back onto my wrists to admire her newest choice of lingerie. The harness fits onto her luscious hips like a second skin, and the silicone cock protrudes proudly away from her body. I look over my shoulder to see my boy's biological appendage doing the same proud protruding, his eyes glued onto her transformed body.

Leaning over and unzipping a pocket on my bag, I pull out a bottle of lubricant. "Part of the fun of having a cock", I explain, "is being able to stroke it. At least, that seems to be case considering how much time most men spend doing it." As her hand lifts off my shoulder and she presents her palm to me, I squirt a large amount of lubricant onto it. The view is delicious as I watch her stroke the red cock, base to tip, coating it in a thick layer of lubricant. The splashing water, gentle conversation, and soft moans make up the background noise to this show as the rest of the guests in the pool go about their business.

"Don't be shy," I coach. "Try pressing the base against your body". Her next stroke is done with more force, and the base of the dildo presses into her body. Her body tightens as the strong muscles of her thighs visibly tense under the pleasure. Another carefree laugh escapes my lips, and I pat her thigh reassuringly. "And that's how women can orgasm from pegging."

His preview show reaching its end, it's time to get my short-haired boy into place, and I crawl the few feet required to reach his side, the bottle of lubricant in my hand offsetting my usual balance. Using the tabs on the suction cuffs, I remove them from the harsh, unforgiving tile and require him to flip over with the front of his body pressed into the damp towel underneath him. I watch as an errant water droplet runs down his back and onto the towel underneath him. A quick press of the suction cups has refastened his arms straight out away from him on both sides, giving us plenty of room above and below his arms. Once in place, his cheeks are spread, and I squirt a dollop of the lubricant onto his entrance for a bit of added slickness. As a final touch, a blue, non-slip knee pad is placed on either side of my boy's hips. After all, we wouldn't want her getting uncomfortable during her first pegging session, now would we?

With all of the preparations complete, I take my place to enjoy the action as I kneel over his head, my knees touching both shoulders as I face his butt. Holding his shoulders down onto the ground with my panties right above his head, I watch as she crouches over his naked butt, her new-found silicone body part in hand. Slickened and lubricated, she wastes no time positioning the tip of the thin, long cock against his entrance. With a bit of adjustment from her as my hand to help position the toy where it needs to be, she pushes the red toy into his body. As her length pulls the first whimpers from his mouth, she slows and lets his body adjust to the penetrating toy.

With her weight pushing his hips into the tile beneath him, I begin to let my hands wander all over his upper back, leaving red trails behind as my nails lightly etch their visit into his skin. The lovely woman in front of me continues to sink her length into his body, and his heavy breathing between my legs is the only proof I needed of that. She falls forward onto her hands, her head pressed against my right hip as the final inches of her toy escape into his body. I slip a hand along the length of her back as my other hand finds its home within the soft tendrils of her short hair. In our little bubble, the only sound I can hear is the harsh breathing coming from both of my submissives.

"Now", I instruct, "Go ahead and pull out a bit and push back in. Not all the way out, though."

No sooner are the words out of my mouth than the brunette is pulling her body away from his and pushing back into him. Her reward is a high-pitched, pleasured gasp that escapes his lips. "Good boy", I praise, reaching between my legs in order to move a hand to pet his hair.

"Huh", she muses with her next thrust. "I don't think I've ever moved my hips like this."

I trace my hands up the soft skin of her stomach and onto her plentiful chest. Grasping her breasts and playing with her nipples, I hear the soft displacement of water as some of the other guests of the pool have started to swim their way over to our side of the pool to enjoy the show. "Don't look now", I whisper into her ear as I bend over to talk to her, "But you have an audience."

The knowledge causes her hips to freeze for a second before I offer a reassuring pinch of her nipples. With a squeak from her throat, she resumes her thrusting, and I watch the rise and fall of her curvaceous ass with each stroke that she gives the boy underneath us both. The harness straps support her ass beautifully and add even more curves to what she was born with. Some of the couples in the audience are clearly enjoying the show, and I watch as a woman strokes the length of her partner's cock underwater. My girl's breathing becomes more labored as she slips her length in and out of his body, her knees resting on the knee pads beneath us, her head pressed into my side to support some of her body.

"Time out for a second," gasps the boy underneath us, barely audible as he speaks into my thighs. I pull myself off of my heels and let him speak, easier to hear now. "You're doing a great job," he continues, "but I'm just too hard, and you're pushing me into the concrete." I watch as my girl giggles but learns to accept her dominant role as she leaves the length of her cock within his body to tease him for a few more seconds, careful to avoid pushing him into the concrete, to make him reflect upon his request.

"Now that doesn't have to mean the fun is over," I say with a mischievous smile that matches her own as I catch her eye. "Let's let you experience what it's like to have him on top."

 




Joanne Queenin
Joanne Queenin

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