Pop Star Cucks Boyfriend with a Professional Dom — Part 1 (Commission)

Themes: BDSM, Cuckoldry, Rough Sex, CNC, Bondage, Anal, Chastity, Celebrity, M/f/m

“Pop Star Cucks Boyfriend with a Professional Dom” was a commission for a client over on my Fiverr. They kindly provided permission for me to post their story on Medium! As a commission, it means that the content might be exceedingly specifically, or exceptionally broad.

Tiffany sighed heavily. She had just arrived home after an eight-month tour of the US, promoting her newest album. She was utterly exhausted. Her long blonde hair was messy, and she had bags under her eyes. At that exact moment, she only wanted two things — one; to sleep, and two; to be fucked and ravished beyond belief. She knew her boyfriend would be home soon, but as lovely and kind as Zac was, Tiffany had kind of shot herself in the foot when she agreed to let him move in.

She wanted a real man, a strong, powerful man who’d put her in her place and show her what being a woman felt like. Outwardly, Tiffany was a powerful feminist who inspired women around the world to demand equality, but sometimes, almost contrarianly, she just wanted to be treated rough, fucked from behind, have her hair pulled. Zac, to Tiffany’s disappointment, was not that kind of man, in fact, he was quite the opposite.

Zac was a complete submissive. He couldn’t get off unless she was on top, and she’d even caught him cross-dressing a few times — not exactly the masculine fuck machine she craved. It didn’t stop her from trying to get Zac to do her the way she wanted, but even when he did do her from behind, he had to be coddled, encouraged, and supported as if it was his first time ever. The best fucking Tiffany had received in years was from her favorite rubber cock, mounted to the door of her bathroom.

The door swung open, pouring afternoon light on Tiffany’s exhausted body. In walked Zac. He smiled, waved, and rushed over to her like a puppy seeing his owner after work.

“Hey, babe!” he kissed her on the cheek, “How are you?”

“Tired,” she sighed, “but also, I’m really desperate for a fuck,”

“Oh yeah? He smirked, “I can help you with that, you on top? Maybe you can sit on my face? I’ll eat your ass?”

“That’s not really what-”

“Oh, maybe you can tie me up!”

“Zac, I-”

“Maybe you can-”

“Ughh!” Tiffany groaned, standing up in a fluster.

“What — what is it?”

“Why do you have to be such a little sissy sub all the time? Why can’t you fuck me like a real man?” she lamented.

Zac looked dumbstruck. He visibly shook his head in confusion.

“I thought you were all about that?!” he gasped, “I thought you loved being in charge!? Putting me in my place and showing me all that raw, feminist energy!” Tiffany could tell he was getting hard just thinking about it. She hated the way her feminism had been fetishized by him.

“Ehh,” she exhaled, “sometimes Zac, sometimes. But I really just wanna be fucked by a man, not a sub.”

“I can do-”

“Zac, you can’t even get it up unless I call you a good boy or something! Just- y’know what?”

“What?” he shivered,

Tiffany sighed with contempt. She was too tired to deal with Zac’s pathetic displays of inferirorty.

“I’m going to find a dom, a real man who can fuck me the way I want,” she stated firmly, picking up her phone.

“But, what about me?”

“What about you!? You’re already a sub, cucking you isn’t a big step, Zac!”

“I-”

“You might as well lock your cock in chastity, sissy man, I sure as hell won’t be using it again,”

With that, she slammed the door, locking herself in her bedroom. She could hear Zac shuffling awkwardly outside. She wondered if she’d been too harsh to him, but he’d been inept for a number of years, and she was desperate to get manhandled. She scrolled up and down the web, searching for the man she craved. Eventually, she found herself on a website promoting a local Professional Dom who simply went by the alias of Sir. He was a master of discretion and required all his clients to wear masquerade masks. Tiffany smiled, this was perfect for her. She couldn’t risk her visit to a dungeon being publicized in the tabloids.

She applied for a session, noting that there was a time available in only three hours. She hungrily accepted it, using a false name and one of her many inconspicuous email accounts. The booking was confirmed and Tiffany fell back on her bed and exhaled a tremendous sigh of relief. She was about to get what she wanted, it was only a few hours away. She began to get ready. She showered, and quickly fingered herself to the thought of Sir plowing her. She applied makeup, neatened her hair, and put on a simple, black dress that rode halfway up her soft, pale thighs.

She slipped on a pair of heels and dug through her wardrobe to find a masquerade mask that she’d used for a fancy dress party some years ago. She found it discarded on a shelf in her closet and quickly tucked it away in her purse, before leaving her bedroom. Zac was sitting on the couch, on his phone.

“I’m heading out,” she nodded, trying to be discrete,

“To the dom?” Zac solemnly nodded,

“Yes,” she quickly retorted.

“Okay.” his head dropped.

She began to walk towards the garage when he spoke up again.

“I- I ordered a cock cage… just — just like you said” he mewed, vying for her approval.

Tiffany rolled her eyes and muttered ‘pathetic’ under her breath, before storming off without another word. She stepped into one of her cars, an unassuming Kia she used when she didn’t want to be hassled by the press, and zoomed out of her compound, heading for a discrete warehouse in the outskirts of LA.

Tiffany couldn’t ignore the intense thudding of her heart as it pounded aggressively in her chest. Adrenaline was surging, and she was unable to shake the feeling of taboo that pervaded her mind. She pulled into the underground carpark and steadied herself. She inhaled slowly, paused for a few seconds, and exhaled, slowing her heart rate and calming her nerves. Once she felt ready, she donned the mask and stepped out of the car, heading for the entrance. She walked inside and found herself standing in a dimly lit room surrounded by black curtains and a handful of chairs. There was a small desk with a bell and a sign that read ‘If unattended, please ring,’.

Tiffany’s hand hovered above the bell for a moment, shivering with anticipation, before it slammed down, sending a rippling ting sound throughout the otherwise silent room. A few seconds later, one of the curtains was brushed aside from behind, and out stepped a man. He was shirtless, buff with a dabble of chest hair and tight leather trousers that left very little to the imagination. He was wearing a masquerade mask, black and ornate.

“Hello,” he smiled, his voice calming and silken, “you must be…” he picked up a tablet and scrolled through his bookings, “…Esme…” his eyes portrayed not an ounce of belief as he looked her up and down.

“Okay… Esme,” he winked, “I’ll be with you in just a few minutes. Here’s the ToS and waiver, just sign that, and we can start,” he handed her the tablet.

Tiffany was shaken. She couldn’t escape the feeling that he had recognized her. She was, after all, one of the most recognizable women in modern history. She signed the documents without even reading them and pressed submit. A few minutes later, his voice called out.

“Come in,”

She stood and followed the voice, passing a curtain. She stood in shock at the scene before her. Shackles on the walls, benches, and beds with cuffs attached. Whips, dildos, vibrators, gags, and anything and everything sexual hung from the wall in a vast array of sexual paraphernalia.

“This is… a lot,” she gasped,

Sir just smiled at her as she became accustomed to his dungeon. There were two other women in the room, both locked in metal chastity devices and bondage hoods. They were cleaning the dungeon at Sir’s request. Tiffany tried not to look shocked at their naked appearance.

“Your form submission said you wanted to experience manhandling and rough sex. Is that correct?” Sir asked,

“Y-yes,” Tiffany whispered,

“Do you have any aversion to toys or restraints?”

Tiffany shook her head. No.

“Do you have a pre-prepared safe word?”

“Safe word?” she asked innocently.

“If things get too much, a safe word is uttered, and it means ‘stop immediately’. Sometimes words like ‘no’ or ‘stop’ are just sexual moanings, so we use safe words, words that won’t be uttered in the heat of the moment. For instance, pineapple is a popular one.”

“Let’s just go with pineapple then,” Tiffany nodded, a little overwhelmed.

“So just say pineapple if you want me to stop at any point. No other word will make me stop and unless you say it, I’ll assume you’re enjoying yourself, understood?”

Tiffany agreed.

“Alternatively, if for whatever reason you can’t speak, three loud taps will suffice.” he knocked on the wall thrice to demonstrate.

“Let’s get started then, up against that wall. Facing the brick,” he demanded.

Tiffany was a little hesitant at first, but she soon found herself facing the wall just as instructed. She could feel her arousal growing immeasurably, and nothing had even happened yet. She could hear Sir shuffling about, picking up what she assumed were cuffs and shackles. She was right, for the most part.

“Lift your hands above your head,” he instructed firmly.

He wrapped a pair of shackles around her wrists and clipped them into a hook on the wall, securing them in place. Without asking, he brushed her legs apart, widening her stance. To steady herself, her backside shot out and her back arched, almost pressing her face into the cold wall. He clamped one shackle around her left ankle, and another on her right, before affixing a steel bar between them.

Tiffany spoke, “What does that-”

“Shh, you don’t have permission to speak,” Sir interrupted.

He smirked and kicked the spreader bar. The telescopic metal sprung forward, forcing her legs even wider apart. She moaned in shock, but her arousal was soaking her panties.

With his new pet secured against the wall, Sir began running his hands down her sides, feeling every curve of her body beneath the tight-fitting dress. His hands slipped under her skirt and firmly squeezed her backside, eliciting a soft mew from Tiffany. He began to kiss her shoulder, exhaling passionately as he placed his lips in the nook of her neck.

“As of now,” he whispered in her ear, “I own you, Esme, you do as I say or get punished. Understood?”

“Y-yes,” she cooed,

Suddenly, an open palm spanked her ass.

“Yes, what?” he sneered.

“Yes, Sir,” she gasped, suddenly feeling a rush of excitment.

“Better. When you are here, you exist to please me, you exist to obey me. If I want to fuck your ass, I will. If I tell you to suck my cock afterward, you will. Understood?”

“Yes, S-sir.” she whimpered, incredibly aroused and excited.

“Good,”

Tiffany heard a distinct click and suddenly felt her dress get sliced off from the rear. It fell to the floor in a heap, and Tiffany was now standing in her lace lingerie, chained to the wall.

“Hey!” she gasped,

“I told you, no speaking,” he snarled, “now I’ll make sure you can’t,”

He took his small knife and sliced her panties off. They hung from her tightly clenched butt for a moment before he pulled them out. He lifted them to his nose and inhaled her scent deeply.

“Excited, aren’t we,” he smirked.

Sir bunched the panties up in his hand, before stuffing the sodden, sweaty panties into Tiffany’s mouth, pussy-first.

“Mmphm, mmphmm?!”

The taste of her own ass sweat and arousal flooded her mouth with potent flavor. The bitterness of her excitement made her wince and the salty, stale sweat of her backside almost made her gag, but Sir’s complete control over her was making every discomfort entirely worth it. Sir picked up her dress and folded it until it was a single, long strand of fabric, which he then pulled through Tiffany’s mouth and tied around her head, sealing the pungent panties inside. Tiffany now had absolutely no choice but to endure the bitter taste of her own nether as her saliva coated with sweat and pre-cum and trickled onto her tongue and down her throat.

Sir was busy rubbing his hands on and around Tiffany’s assets. Her thighs quivered with each touch, her butt wobbled as he squeezed it, and her breasts heaved when he tweaked her nipples. She mewed through her gag, shivering every time his big, masculine hands touched her soft, delicate, feminine body. He leaned forward, placing his mouth just beside her ear.

“You’re mine,” he whispered.

His words sent chills down her body, her skin became pocked with goosebumps. He stood back to admire his work. Tiffany, the international celebrity and feminist pop star, was bound to his wall, naked and begging for his touch. Her body was as incredible and amazing as he’d expected it to be. Her legs were long and slender, and with her stilettos still on, they looked even better. Her backside was broad and perky, her waist was narrow, and her breasts were delectable. It was an image of pure beauty, and if he could take a photo of it and display it on the wall above his bed, he would do so in a heartbeat.

“Time for some fun,” he smirked,

“Mmmphm mmmhmm,” Tiffany muffled into her gag.

Sir approached the wall on which his vast array of toys was displayed. He pondered for a moment, ‘which toys should I use on her?’. He settled for a clitoral massager, nipple clamps, and a vibrating butt plug. With a grimace, he turned back and strolled confidently over to Tiffany. He applied the clamps to her erect, firm nipples, and Tiffany groaned and winced as the sharp sting shot through her body. He squeezed her breasts and flicked her nipple with his tongue, teasing her before withdrawing the buttplug and showing her.

Her eyes widened with a mixture of fear and excitement. The only thing Tiffany had felt up her ass before was Zac’s nose, and occasionally his tongue. Sir spat on his hand and coated the plug with his saliva, before parting her cheeks and staring eye-to-eye with her cute, puckered asshole. He looked forward to plowing it with his cock, but for now, his new pet needed to be edged to submission. The plug slipped into her ass, and Tiffany flinched as her anus tightened around the base of the plug. Sir tugged it gently to ensure it was firmly entrenched in Tiffany’s magnificent asshole. With a wicked grin, he used the Bluetooth controller on his phone and turned the vibrator on to the max. Tiffany’s legs almost buckled, and if it wasn’t for the chains suspending her hands on the wall, she might’ve fallen.

“Hnnghh, hmmmphh!” she moaned as it tickled her from within.

Sir smiled, pleased with his work, but he wasn’t done yet. He watched as Tiffany squirmed, the tantalizing sensations emanating from within her butt made her weak. She’d never felt such a sensation before, let alone whilst bound to a wall with her legs spread, in the presence of one such as Sir.

Her quiet, gagged moans were literal music to Sir’s ears, he could feel his own cock straining against his tight leather pants, dripping pre-cum down his leg as Tiffany’s perfect body rippled with pleasure. Her whimpers of arousal echoed off the otherwise quiet walls of the dungeon. Her back arched and her backside stuck out in all of its exquisite roundness. The flared tip of the plug covered her cute sphincter with a red jewel. Sir picked up the clitoral massager, wishing to enhance Tiffany’s experience, but really, to enhance his own. There were few things on this mortal plane that aroused him as much as a bound woman, writhing, moaning, and whimpering as they are forced to endure great amounts of sexual stimulation. Perhaps the only thing better was it happening to a globally worshiped, physically perfect, famous, female pop star like Tiffany.

Even he wasn’t sure how long he could hold himself back from ravishing her. He was already struggling to do so, but for the sake of professionalism, he’d try to hold himself back… for now.

He slipped the clitoral massager’s tail into Tiffany’s cunt, and pressed the oscillating massager against her clit. With a quick kiss on her neck, Sir smiled and turned that up to the max as well.

“MMHPMM!” Tiffany squealed, her knees completely gave out.

She fell, suspended only by her shackles. Her moans were long and drawn out, broken only by frantic inhalations. Her body was writing as if she could feel bugs in her skin, she slowly staggered to her feet, her backside flexing as she struggled to stand. Her chest was heaving up and down as she breathed laboriously, fighting against the immense urge to unleash any number of uncontrollable orgasms. Sir mewed in enjoyment, watching her strain and wriggle. He waited and watched until her pale, smooth skin began to flush red, and that was when he lowered the devices to a quiet hum — low enough that she wouldn’t cum, but high enough that she’d be held in orgasmic stasis, right on the cusp of climax, but never passing it. He kept her there for a moment, listening to her almost therapeutic, involuntary whimpers each time she exhaled.

Her excitement was running down her legs, and her body was quivering like a leaf in a hurricane, at this point, any touch against her delicate warm fresh would make her shiver and moan. This was exactly where he wanted her. He approached, standing right behind her, so close that he could feel the warmth of her back against his bare chest.

“Enjoying yourself?” he mewed,

“Mmhmm mmmm,” was all she could muster.

It sounded like a yes to him. He gently placed his splayed fingers on her outer thighs. As predicted, she shivered at his touch. The additional stimulation, no matter how small, was almost enough to make her cum.

“Mmhpmm! Ennghh!” she moaned, her body twisting to escape his arousing touch.

He began to run his fingers up her side, curving around her voluminous backside, to the ticklish part of her hip, and up to her ribs. She moaned a long, slow, moan, her breath was stammered as though she had hypothermia. Sir smiled again, relishing her situation. He began kissing her back, working his way down, planting his lips on her flesh each and every inch until he was squatting down, his face eye level with her perfect ass. He planted a kiss on her inner thigh and she practically melted. He chuckled to himself and began gently stroking her inner thighs with a feather.

She jutted and tried to avoid its sensitive touch. Each moment of contact felt like it was injecting an orgasm right into her bloodstream. She couldn’t bear it, but at the same time, she could. She wanted more. As strained moans passed through her panties and out of her gagged lips, she realized this was exactly what she needed, what she wanted, what she craved. She wished Zac was like this, and not the closet sissy she suspected he was. Her mind was in bliss, flooded with endorphins and adrenaline and orgasmic energy the likes of which she’d not thought possible. She was so dangerously close to cumming so furiously that she feared she might flood the dungeon, but somehow, Sir, in all his professional glory, was touching her just so perfectly that she couldn’t quite finish, but was, instead, left to quiver and shudder as the orgasm built like water behind a dam.

“Mmmhpm mmhmm phmm! Enguhmmm!” she moaned, begging for said dam to burst.

She was so desperate to cum, she couldn’t take it any longer, but she also didn’t want it to end. Ever. Sir smiled that cheeky, sultry smile of his and slowly amped the clitoral massager and vibrating butt plug back up to level 11, whilst he continued to kiss, massage, and tease her thighs. Tiffany contorted, the shackles rattled and her moan echoed loudly throughout the dungeon as the culmination of almost an hour-worth of edging finally reached climax. She felt as though the life had been drained from her, her knees gave out, her head dropped limply and her vision faded into nothingness as her mind seemed to transpose with pure bliss. For a moment, she felt herself hovering above her quivering body, looking down as Sir gently ran his hands down her side. She shivered, slowly coming back to reality. Her eyes opened, she was staring at her feet and Sir was leaning above her, unshackling her from the walls, but not undoing the cuffs.

“Mmphmm?” she drearily moaned,

“Do you wish to finish?” he asked, ensuring she was comfortable.

She shook her head, no, never. He smiled and ushered her bound body over to a large bench that stood about waist-high on Sir. He propped her against it, slowly lowering her chest onto the broad, wooden platform until she was bent over, her feet on the floor, her head on the bench. Sir affixed her cuffs to a clip at the top of the table, and secured her ankle cuffs, still attached to the spreader bar, to the feet of the bench. He playfully spanked her ass, eliciting a quiet, muffled yelp from her. Sir was about to have his fun, and he, like Tiffany, wanted it to be perfect. This was as much a fantasy for him as it was for her. He’d be kidding himself if he said he never fantasized about Tiffany, to the point where he’d sat at his desk, his mouse hovering above an invite for her to come around for a session, and where he’d played her music whilst enjoying himself, both alone, and with other clients — often imagining them to be her.

Now, his fantasy was real, as was hers. He wanted to hear her moan, so he untied her gag, and withdrew her panties.

“Holy fuck,” were the first words out of Tiffany’s mouth,

Sir affixed her ruined dress and tied it around her eyes, blinding her. Straining against her bonds, she could only hear the rattling of chains and the ruffling of fabric as Sir did something behind her. Suddenly, after a moment of pressure relief, the buttplug was removed, as was the clitoral massager. Tiffany moaned, but the moment was short-lived, she soon felt something else prodding into her pussy and it didn’t take long for her to realize exactly what it was. Blindfolded or otherwise, she knew a cock when she felt one.

Her body contracted, feeling the oncoming storm of the rampant fucking she had been begging for, for who knows how long. Her mind sent out a wave of endorphins as Sir’s cock nestled its way past her pussy lips and deep into her cunt. He was big. Really big. Just from feeling alone, she could tell that his cock made Zac’s look like an infant’s thumb. His movements started slow, with each thrust pressing the side of the bench harder against her soft thighs. He began to pick up the pace, burying his thick cock deeper and deeper, faster and faster with every thrust, until he was vigorously fucking her. He could see her tight cunt slowly turning red from the impact of his body slamming against it with such volition. She was gasping and moaning, barely able to string together a word.

He kept going, his hands grabbed her ass cheeks and squeezed, using them as a counterweight to his thrusts, and pulling himself back in at the moment of withdrawal. Over and over again, a near-constant battering of her femininity.

“Oh fuck,” she bellowed,

He leaned forward, placing his hand on the back of her head, pushing her face into the hard bench. She moaned and he just kept going. He was utterly relentless, dispensing the fury of thousands of fantasies of doing exactly this — fucking Tiffany from behind as she’s bound to a bench, unable to fight back.

“Oh god,” she cooed, her mouth half-muffled by the table.

He could feel his own orgasm building rapidly. He’d taken a handful of pills prior, black market ones that he always had on hand. They made Viagra look like Tylenol. He could cum ten, maybe fifteen times if his cock could handle it, and all within rapid succession of each other. He pounded her relentlessly, almost brutally. The sound of flesh slapping on flesh intermixed with Tiffany’s moans and Sir’s animalistic groans and filled the dungeon with a cacophony of sex.

“Oh fuck, stop!” she bellowed, wincing at the ferocity of his fucking, “Stop!”

He did not. The safe word had not been uttered, and Tiffany was wholeheartedly aware of that. Despite her words, she did not, in the slightest, want him to stop.

“Stop, ah!” she cried.

Sir fucked her harder, clasping her hair in one hand and pulling it back, causing her neck to crane backward. She pulled it hard until her arms were straining against the taut chains. Tears were beginning to streak down her face, which was wincing with pain and arousal. His cock was burying itself so deeply inside her, it was exploring places she didn’t even know she had. She could feel the walls of her pussy stretching and conforming to fit his massive manhood. Each thrust sent a beautiful mixture of pleasure and pain surging through her body.

She’d never felt such a sensation. She craved more, but every time she went to speak, all she could muster were cries, moans, and sulking mess. Sir’s thighs tightened up, and he climaxed with intensity, his body seized up, and he filled her nether with his essence. Tiffany gasped, shocked that he’d just cum inside her. She shivered, feeling it begin to trickle outwards.

She exclaimed, “Did you just-”

“Shh, you don’t get to speak,” he playfully snarled, withdrawing his cock.

Sir stood, panting, with his dick in his hand and cum dripping from it and landing on Tiffany’s calf. She was exhausted, but her booking still had two hours left on it, she wasn’t going to waste it, and neither was he. The pills were starting to kick back in, and just as soon as he’d finished, Sir was erect and ready to go again. Before he could push himself into Tiffany’s cunt, she stopped him.

“In my ass,” she gasped,

“What?” he smirked. He heard her, he just wanted her to beg.

“Put it in my ass,” she mewed, “fuck me in the ass, Sir,” she bit her lip, “fuck my tight ass as hard as you can, make me scream,”

That’s what I like to hear, he thought to himself. He coated his cock with lube and ran a very lubricated finger around her rim and then dived deep inside, spreading the slippery liquid. Tiffany leaned forward, broadening her cheeks and opening her backside to allow him in. He started slow, as before, and watched with glee as her tight, pink, perfectly immaculate asshole stretched around his throbbing member, engulfing it in tight warmth. It rippled as it swallowed his entire cock, and from where Sir was standing, with his manhood buried in Tiffany’s rear, he had an exquisite view.

She gasped, part in pain, part in desperate arousal, as he began to thrust, just as before. He took more time building up, not wanting to damage her beyond what was pleasurable. Her pussy was dripping with arousal as her ass hungrily enveloped his cock time and time again with each and very laboriously slow and tantalizing thrust. The wrinkles in her anus stretched out and flattened as her booty accepted him inside, and as delightful as the spectacle was, he was too eager to keep moving so slowly.

He wrapped her hair around his hand as if it were rope and pulled, forcing her neck back. He ran his fingernails down her back, leaving a trail of red marks, before he committed to furiously pounding Tiffany’s virgin asshole. She gasped and moaned loudly with each and every impact, feeling her asshole contort and stretch to sizes it never had before. Zac’s tongue had nothing on this. Sir’s cock buried itself in so deep she could almost feel it prodding her stomach, and he was so ferocious with his fucking that she barely felt as if she had time to breathe. To Sir, it felt even more incredible than her pussy. It was tighter, warmer, and even more taboo.

He couldn’t put his finger on exactly why it was such a wildly different experience, in his mind, to just fucking her vaginally, but something about knowing he was the first and only cock in the one and only Tiffany’s asshole was indescribably erotic and arousing. It was as if he’d claimed it for himself, marked his territory. No cock would ever feel as good inside her tight ass as he did, and both he and Tiffany knew it.

“Fuck, fuck, fuck, fuck,” she rhythmically moaned. “Oh god, it hurts, fuck, stop! Stop-”

He pulled her hair tighter, interrupting her false lamentations. He knew it hurt, but it hurt good. Her entire body was quivering with anticipation, and even as his hand pressed her face down again, and his cum trickled down her calf and onto her feet, he knew she was in heaven. He knew, beyond that, that she’d be back, regularly. His balls slapped up against her cunt as his cock was swallowed by her stretched asshole once again. The way her ass cheeks bounced with each impact was hypnotic — an image that would forever be in his mind. In, out, in, out. He wished he had two cocks, so he could fuck her twice.

And then he realized. He did. Without extracting himself from her virgin asshole, he reached over for a dildo and buried it deep into her pussy. He held it with one hand, and her head with the other. It thrust as he did, filling her twice as much. The only lamentation was that he couldn’t feel the dildo. Tiffany was gasping and panting like she’d run a marathon. Sweat was dripping down Sir’s body, giving him the appearance of glistening in the clinical dungeon lights.

He was close to orgasm again, and judging from her moans, so was Tiffany. He kept going, filling both her holes with his fat, juicy cock and the girthy silicone dick buried in her snatch. He could see tears streaking from below her blindfold, and that her mouth was agape, drool pooling below her chin. The pleasure was so potent she had seemingly escaped her own mind. She exploded into a series of sensual yelps and moans, her body seemingly fighting back against the sensory overload as another insane orgasm powered through her like a tidal wave.

Her pussy began to shoot forth a stream of her juices. Sir smirked. Tiffany’s a squirter, he thought to himself, as her essence sprayed out onto the floor. It was such a coveted thing — he could bottle it and sell it for a fortune if he wanted, but that’s not where his mind was. His mind was fixated on the overwhelming pleasure that he was experiencing, and he wasn’t going to pull out this time — not from Tiffany’s asshole, he wasn’t. He was claiming it for his own. He groaned through gritted teeth. His hands clamped firmly around her ass, and his stomach buckled him over into a hunched position as he deposited a gargantuan load of his manhood deep inside her magnificent ass.

Even with all the years of professional sex work, Sir was not ready for the sensation. It had been some time since an orgasm had flawed him so, but when he came too, he was sitting on the floor, staring up at Tiffany’s ass as his cum dripped from it and fell into the pool of her squirted fluids on the floor. It was picture-perfect. He scrambled to his feet and stroked her backside. She shivered at his touch.

The session was over. He unshackled her and took off the spreader bar and blindfold. She fell into a heap on the floor, absolutely ruined. Her delicate, natural-style makeup had run with sweat and tears, and she’d gone from looking like a naturally feminine beauty to a member of a 90s goth band with all the leaked mascara. Sir comforted her as she came too, she looked up at him with pleading eyes. More, they pleaded, more…

He nodded, but couldn’t. He, too, was spent, and somehow he had to still see two other clients that day. Nothing could top what he’d just done.

“Come back next week, I’ll free up an entire day for you,” he smiled, “Tiffany…”

Her eyes widened, even behind the masquerade mask, Sir could see her surprise.

“Am I that obvious?” she mewed,

“To me, yes,” he smiled.

“It’s a secret, right?” she pleaded,

“Of course, but please, do keep coming back,”

“How could I not?” she blinked slowly.

She stumbled to her feet, and he supported her. Her panties were sodden with spit and cum, her dress was ruined. Sir smiled as he saw the realization enter her head. She’d have to run to her car naked, with a ruined cunt and an asshole dripping with cum. More than that, she’d have to go home like that, to her boyfriend, who’d no doubt feel jealous upon seeing her well-used asshole. The thought excited him in a mischievous way, and her too.

Part Two:

— — — — — — — — — — — — — — — — — — — — — — — — — — —

If you want more devilish stories like this, visit my links page! You can find my Kindle, my Smashwords/D2D, more stories on Medium, my Twitter, and even my Fiverr page if you wanted your own personalized erotica!

All reviews, claps, feedback, comments, and shares are immensely appreciated!

-Mel