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Ciaran McNamara was restless as he sat in the makeshift office he had set up in his garage with two friends from his old investment bank. They had grown close over the years working long grueling hours, a shared Irish heritage, gonna the gym, sleep, repeat.  The months with Sarah had been intense and passionate. Following the conference she had basically moved in, but when she was assigned a new desk in their London office, the opportunity and money were too good to pass up.

After Sarah left, Ciaran began to realize months ago how dreadful his life actually was working long hours with little time for outside pursuits.  Sarah had been an incredibly sexy diversion and in her absence, burn out had taken its place. He needed a break and while conversing over drinks with his best friends, discovered he was not the only one looking for an exit plan.  Over the following months, Ciaran, Eamonn, and Patrick had discussed setting up their own hedge fund.  After a few years working as analysts and with no spare time to spend it, the three had amassed sizable savings.  What had begun as small talk about leaving the corporate grind behind had eventually evolved into a detailed plan of pooled assets and most importantly, freedom.

After putting in their notice, the three packed their belongings and made their way to the Florida Keys, a destination that provided friendly taxes, scenery, beaches, women, and a pace of life that all had been longing for.  After considerable searching, the three had each found relatively modest homes in Islamorada in the same neighborhood. Ciaran’s garage became their office and in the months since their new adventure began, their returns had beaten their own lofty expectations. They were still young, each in their late 20s and for the first time in years, able to enjoy the advantages of their growing wealth.

Ciaran, Patrick, and Eamonn walked in to their regular afternoon bar.  They had become regulars and were already making friends among the locals.  Ciaran locked eyes with the bartender as soon as he walked in and they exchanged flirty smiles as Patrick and Eamonn make their way to a table.  Her name was Emily and though you’d never guess it, she was exactly the sort of girl that caught Ciaran’s attention.  Bright orange hair that clearly wasn’t natural, tattoos in all the right places, and a tight, firm body that proved she had a pretty serious fitness routine.  Ciaran had been ensorcelled since the first moments he had laid eyes on her, but had tried to play it cool during their brief time here.  However, tonight he was no longer interested in playing it cool.  He wanted her and the wondered of what he wanted sent a pulse of energy coursing through his entire body.

Emily was having the exact same thoughts. For months she and Ciaran had flirted, but she hadn’t given it much more wondered prior to tonight. There were at all times a steady stream of bikini clad vacationing school girls hanging around him, but tonight she sensed something in his stare that stirred inside her and made her ache with desire. He had been a mystery to her since he and his friends first moved in.  He was clearly wealthy, but did not appear to carry himself like a trust fund kid.  She knew from their brief conversations that they were somehow involved in investments, but he did not look the part.  Tall, muscular, and covered in tattoos just like his friends.  She had seen many of those tattoos, but tonight she wanted to see them all.

Rather than joining his friends, Ciaran made his way to an empty spot at the bar and ordered a beer. Despite others having waited longer, Emily made sure to get to Ciaran’s drink first.  He didn’t know for sure if this was a sign of interest or just a result of his habit of tipping her very well.  However, after finishing up with the other patrons, she came over and removed all doubt. ‘So are you finally gonna ask me back to your place?’  The forwardness of the question caught him off guard, but he found his footing quickly asking her what time she was off.  ‘The bar closes at 1, but I am sure I can get someone to cover the rest of my shift…if you promise to make it worth my time!’  With that, she gave a sly smile and a wink before heading back to talk to a coworker.  After a brief exchange, she tossed the bar rag in her hand and came around the bar, taking Ciaran by the hand.  Ciaran yelled to his friends that he was heading home for the night as he clasped Emily’s hand and hastily exited the bar.

Realizing his friends still needed a ride home, they ran to Emily’s Tahoe where Ciaran pressed her firmly against the side of the vehicle.  There was the briefest moment of breathless hesitation as they looked into one another’s eyes, the hunger growing before their lips were pressed together, hands frantically running over one another’s bodies!

‘GET A ROOM!!!’, ‘It’s about time, you two!’

Their kiss was interrupted by the yelling and howling laughter of Eamonn, Patrick, and several female bar patrons and servers who were now standing on the deck laughing at the pair.  ‘On our way there now!’ Ciaran replied as he and Emily chuckled before climbing in and quickly exiting the parking lot, spinning up gravel as they sped away.  Emily could barely focus on the road as Ciaran ran his hands along the inside of her thigh, much higher than is typically polite on a ‘first date’, but the sexual tension between them had been building for some time now.  This was not the ordinary first date and Ciaran had no intention of allowing it to be.

Emily hears him moving around the room, the click of the toy box as it opens, and Ciaran rummaging through for all the items he planned to use on her. The unknown excites her as she lies completely naked in the bed, hands bound above her head and ankle cuffs holding her legs wide aside.  She is in total darkness under the blindfold and the anticipation of what is to come has her wetter than she wondered efficient, but also nervous in this moment.  This was a significant departure from what she had been imagining for months. She had never experienced anything like this and the wondered of being completely at his mercy elicits a small amount of fear.  No matter, she trusts him and has wanted this for so long. In this moment, she thinks there is nothing she wouldn’t do for this man and besides, after the hours she has sat for tattoos, she feels confident that she can take whatever he has planned for her.

Ciaran watches her body writhing on the bed.  She is perfection in his mind and though he loves these games, he has no intention of inflicting any real pain. Her hips press upward into the air, desperately wishing to feel something against her swollen clit. Without warning, thwack!!! She feels the slight sting of the riding crop on the inside of her thigh.  Her body tenses in surprise and excitement and Emily is suddenly aware that she liked it!  She hears him moving again…thwack!!!  The familiar sting, this time on the inside of her other thigh….thwack, thwack, thwack….three in succession on her stomach and each nipple, which stand at attention from the sensation.  She groans softly and wiggles in the restraints as Ciaran watches her glistening pussy, already soaked.  She feels him brush the crop up the inside of her thighs before brushing it ever so slightly across her clit. She can feel her whole body tingle at this slight touch, but knows that she will have to wait for more attention.

She feels the weight of him on the side of the bed and feels his body hovering above hers.  Suddenly, she feels the warmth of his tongue flicking across her nipple, followed by slow circles, before finally being sucked into his mouth.  Her nipple stretches as he sucks it in and she can feel his teeth gently biting before finally feeling the clamp being applied.  Emily squirms slightly as she feels him slowly release the handle allowing the full force of the clamp onto her nipple.  Ciaran pauses briefly as she adjusts to the pain of the clamp before slowly kissing his way over to her other nipple.  He repeats the process and once again gives her a moment to adjust to the feeling before….thwack!!!  She feels the sting of the crop on her belly, though he is clearly not being forceful with each strike.  Emily had already realized this and was no longer anxious, she loved every second and every sensation he was providing. Thwack, Thwack, Thwack!!!  Three more in quick succession down her belly to just above her swollen clit.  She gasps with each strike, but having become more comfortable, she even considers where on her body she wants him to strike next.  She doesn’t wait long before she feels the crop once again slap the insides of her thighs, down her legs to her calves, and finally the bottoms of each foot.  Her toes curl with each strike and though she can’t see him, she knows that has brought a smile to his face. She had long ago noticed his stolen glances at her feet over these past months and had made pedicures a more regular part of her routine.

Emily braces herself for the next impact from the crop, but suddenly she feels Ciaran’s lips on her toes, slowly taking them into his mouth, sliding his tongue between each as he uses his hands to gently massage them. She smiles wondering how long he had dreamed of this. Ciaran takes his time with each foot, with every toe, the gentleness a big departure from the previous activity.  He watches her body heave as she breathes deeply, letting out soft moans as she enjoys every sensation from his hands, lips, and tongue.  There are moments where she is a bit ticklish on the bottoms of her feet, but the restraints do not allow for an escape.  She begins to spread her toes wide, silently letting him know that she wants to feel his tongue between each one again.  Ciaran is all too happy to oblige as her hips continue thrusting towards the sky, begging to be touched. One slow final lick between each toe and she feels him once again on the move.

After a brief moment, Emily feels his hands as he slowly slides them from her feet, barely touching her skin as he brushes his fingers along her ankles, calves, inner thighs.  The light touch send chills down her spine as she feels Ciaran’s hands getting closer and closer to her throbbing pussy.  She feels him slowly slide his finger inside of her and begins to circle her clit with his thumb.  Emily gasps loudly and holds her breath as he slowly slides his finger back out, pressing firmly against her as he slowly slides his finger down to her asshole.  She relaxes as she feels him start to slowly slide his finger around the edge, pressing slightly, but not enough for insertion. Ciaran uses her wetness as lube before slowly sliding my finger inside and out again.  Suddenly, Emily feels the cool pressure of the butt plug as it presses against her tight asshole.  She relaxes and raises her hips off of the bed allowing him to slowly slide it inside before lowering herself back down onto the bed.  Once again, Ciaran allows her a moment to adjust to this new sensation as she makes herself aware of her entire body.  She can still feel the dampness of his saliva on her toes, which is making them cooler than the rest of her body.  She feels the clamps, tight around her hardened nipples which is providing just the right amount of the ‘hurt so good’ feeling.  She clenches her butt and feels the metal plug inside of her ass and of course, her swollen clit and pussy.  She is so ready to be touched as she continues to feel his hands slowly rubbing her entire body. Ciaran makes his way back over and she can hear him as he pulls something new out of the box.  The anticipation is driving her wild as she wonders what is next.

Suddenly, she hears a click followed by the familiar buzz of a wand vibrator.  She can feel him approaching and wiggles her hips in excitement as he leaves it on the lowest setting and lays it between her legs, resting the vibrating head on her clit and holding it in place as she slowly gyrates her hips, pressing firmly against it.  All the anticipation, excitement, and fear already has her on the edge of orgasm and her breaths become heavier, moans louder as she feels the low vibrations against her. Ciaran slides his fingers along her wet pussy around the edge of the wand and pulls her skin tight around her clit as he suddenly increases the speed of the wand. Her hips start to move more erratically and the moans grow louder as her body clinches and she pulls tight against the restraints. She can feel herself ready to cum and once again, he watches her toes curl as her moans turn into screams of pure pleasure.  As the waves of pleasure take over her body, she begins to spasm, her head raised and body stiff. Emily has been waiting patiently for this release and she feels herself cumming harder than ever before.  As her body spasms, she feels the head of a large dildo slowly slide up and down between her wet slit before it slowly slides in. Ciaran uses one hand to slowly slide it in and out while continuing to hold the wand in place with the other.  Emily can no longer hold the tension in her body as she falls back onto the bed. With each stroke Ciaran begins to pick up the pace, slamming the dildo inside of her again and again as she cums.  He watches as her wet pussy lips grip tightly to the dildo and hears the air escaping with each thrust.  Her whole body remains rigid in the midst of her orgasm and suddenly he feels the warm wet splash on his hands as she squirts again and again, raising her head once again, toes curled and turned inward as the restraints are pulled to their limits.  

As Emily’s orgasm begins to subside, he lowers the speed of the wand and slows the pace of the dildo as she continues to enjoy the final ripples of orgasm. The tension in her body had lasted so long that she notices a slight headache forming from all of the clinching.  Finally, as she begins to catch her breath, he slowly slides the dildo from inside of her and turns off the wand, setting it to the side.

Emily can hear the rip of the velcro straps and feel her legs unbound.  Immediately she hooks her heals around Ciaran’s back and tries to pull him onto her. She can feel that he is already naked as her feet and legs slide along his body and he slowly lowers himself onto her and she can feel the head of his cock resting against her slick pussy. He slowly slides forward and raises his hips, careful not to allow himself to slip inside. He presses his body down onto her and uses the bottom of his stiff cock to slide slowly, back and forth across her clit. Emily arches her back and inhales sharply at the feel of his cock against her. He continues to hold himself up with one arm and with the other reaches to take off the blindfold.  He is almost ready and he wants to see the lust and longing in her eyes.

Ciaran holds himself above her, continuing to slide his hips up and down, pressing his cock firmly against her clit.  He begins to slide a bit faster as she moves her hips, desperately wanting to feel him inside of her. He raises up and lifts her legs against his chest, her heels resting on his shoulders as he takes his cock in his hands and slowly guides it inside of her. Emily moans and arches her back again as she feels him slowly fill her, stretching her as he lowers his body, folding her in half. He is completely buried inside of her as they look into one another’s eyes before he leans to kiss her.  Their lips meet and then slowly part as their tongues slowly circle each other.  He slowly raises his hips, sliding out of her slowly before slamming back inside and holding once again.  She cries out with pleasure as he slowly slides back out of her all the way, this time, re-entering and sliding back in slowly. He continues this several times as Emily begins to grow impatient. ‘Fuck me….please, fuck me!’  Ciaran loves the teasing, but decides to do as she has asked.  

Gradually, he begins to pick up the pace with each stroke, she moans encouragement as she feels the pace pick up. ‘Yes….yes….faster….harder!’ He sees her toes curl again and her face begins to contort with pleasure as he slams himself in and out of her as fast as efficient. He feels her legs start to shake and her body tensing, holding her breath as another orgasm approaches.  Their bodies are slick with sweat and Emily pulls tightly on the bindings above her head.  He watches as her toes spread wide beside his face as he feels her pussy start to spasm around his cock.  She cries out something indiscernible as suddenly he feels the warm wet splash across his stomach and thighs exploding from inside of her.  He lets her legs fall to his sides, but keeps the same rhythm, driving his cock deep inside of her.  With her legs once again freed, she wraps them tightly around his waist, feet locked together behind his back.  He presses his mouth to hers and she responds, aggressively kissing him. He can feel her ragged breathing and moaning in his mouth as her pussy continues to spasm and grip his cock.  She feels so amazing and Ciaran can sense that it won’t be long for his own orgasm, but he doesn’t want to cum in her pussy.

As her orgasm begins to subside, he slides his cock out and rolls her onto her belly, hands still firmly restrained.  Emily pulls against the bindings to position her knees beneath her as her face rests flat on the bed.  Ciaran slides his cock back inside of her, and slowly slides in and out of her once again as she feels the cold, slick lube start to drizzle down the crack, over the plug, and onto him.  As he continues slowly sliding in and out of her, he gently pulls the plug from her ass.  Thwack!!! Emily lurches forward, slightly as the crop across her ass was unexpected. A few more strikes to each cheek and he is ready. He slides his cock from her pussy and slides it up, gathering all of the lube he can along the way. With one hand on her hip, he feels her brace herself, knowing what was coming next.  He slowly presses forward, feeling her tight asshole allowing his stiff cock inside. Once the head is in, he pauses for just a moment allowing her time to adjust.  She moans again seeming to enjoy the sensation so he presses forward once again.  He slides in a little further and pauses again, making sure she is okay before proceeding yet again.  He continues to slide slowly, but this time there is no pause until his stiff cock is completely buried in her tight asshole.  He can feel her pull and push slightly and though a bit uncomfortable, the feeling of having him inside of her ass appeals to her. She feels loved and dirty, exactly the way she imagined it would be the first time she saw him walk into her bar. Her orange hair is damp from the sweat and clinging to the side of her face as he grabs her hips firmly and slides almost all the way out and back in slowly.  This only repeats a couple of times as his cock feels so good inside of her tight asshole and he knows he cannot hold back any longer.  Ciaran can feel his balls start to tighten as he begins  to forcefully slam his cock in and out, in and out again and again.  Emily offers him breathless encouragement, ‘Cum in my ass, baby!’ That was all he needed to hear as he feels his cock twitch slightly, then pulsating as he feels shot after shot of thick cum shooting deep into her beautiful ass. She rocks back against him, matching his thrusts and squeezing her ass cheeks together until she has completely drained him.  

Ciaran collapses beside her and frees her hands and she immediately pushes him onto the bed, straddling him and giving him one final passionate kiss.  She lays her head on Ciaran’s chest and slides to his side with one arm and leg thrown across him.  They are both covered in one another’s fluids, but neither has the energy to get up and clean themselves off. Emily pulls the comforter over them and resumes her previous position and gently rubs his chest before one final kiss.  In her final moments of wakefulness, she can feel his warm cum slowly sliding from her ass and down her leg, reminding her of all tonight’s events.  As she begins to fall asleep, she wonders to herself what else he may have planned for her and she smiles at the wondered.

NSFW: yes

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