Cherry on Top

08:00

Cherry blinked at herself in the mirror. She was tired, and she was hungry. Her stomach rumbled. She sighed, took a sharp breath, and slid the thin plastic tube inside her arsehole. Squeezing the bulb in her hand, it filled her with lukewarm water.

Placing the douche down on the counter top, she leaned forward over the unit to look closer into the mirror as she shook her ass around. It felt like something was in her eye. An eyelash had come loose perhaps. It was just a wayward strand of her crimson red hair. No problem then.

She walked to the toilet, sat and noisily shat out all of the water. Her 17:30 appointment was a semi-regular. The session with him almost always involved hard anal, so that meant no breakfast, no food the night before and no coffee all day. Oh, and an enema for good measure. It was all worth it for the wad of cash that came was the assfucking, though.

Finishing up in the bathroom, Cherry strode nude into the kitchen, taking a glass of water from the sink and heading to the bedroom. She rolled some sheer black stockings on to her bare, milky thighs and attached them to a black garter belt. A few moments of indecision came, staring into the wardrobe, before she picked out some lethal heels, and a set of menacing leather boots. Those would be for her 15:00 appointment.

She stood in front of the full length mirror, awkwardly bending to put on the heels. Standing once again upright and proud, she studied herself in the mirror for any imperfections. She saw none. Throwing a silk dressing gown around her bare torso, she grabbed a cigarette and clacked across the laminate wooden floor to the balcony.

Staring out across the city from the 17th floor apartment, she watched as the metropolis bustled into life. The sun was pretty much up now and there was an omnipresent hum to the city's traffic. A police siren pierced the air as Cherry sucked the last drags of smoke from the cigarette and threw it over the edge.

*

09:00

She answered the door with the silk slip wrapped around her.

"Hey, honey!" She beamed, "How are you?"

Reggie padded into the apartment, rubbing his hands together.

"Oh, you know," he sighed, "better now that I'm here!"

He was a small man, with a slight build and greying hair, well into his fifties. He made no effort to conceal the wedding ring on his finger. He always wore a dark green raincoat and his face was soft and unassuming. He was the type of guy you'd walk past in the street without even noticing.

"Have you missed me, baby?" She teased, turning to lead him through the apartment and into the bedroom. She made the effort to exaggerate her swagger, making her fat bum move in hypnotic motion as she walked.

Reggie only nodded. His mind was focussed on her arse poking out beneath the silk slip.

In the bedroom, Reggie placed a brown envelope on the heavy wooden dresser and methodically began to undress himself. Cherry had come to know him as a simple man of very little words. He came, he shagged, he left. A good weekly earner.

The bed was a king, starched white and covered with a purple silk sheet. Cherry fucking loved silk. The way it felt against her skin made her feel a million bucks, even if she was being plowed by the ugliest, fattest builder in Britain.

Reggie stood before her nude, save for his socks. His stubby 4 inch cock was already erect, something she respected in a man of such silver years. Reggie, for all his plainness, still had that fire.

She removed the slip and it fell to the floor. He stood there, gazing at her bare body in the suspenders, garter and heels.

"I'm still thinking a small C, but I don't know which to try today," he said, coming towards her and taking her milky tits in both his hands. Her skin was deathly pale, in contrast to her tattoos and dyed red hair, and her nipples were fat and pink.

This was a game that they had been playing for some weeks now. Reggie had - during a previous drop of the silk - made a calculated guess at her bra size, but had been wrong. Every week since he had taken another guess, but he had still been incorrect. He wasn't very good at this, but he was narrowing down the answer.

"Close, baby," she purred, kissing him on the neck, "remember, when you get it right I'll let you cum all over my tits as a reward."

She dropped to a squat before him, making sure to catch a tit on the head of his cock as she did.

She took him in her mouth. His diminutive size made it a breeze for her to deepthroat him, and Reggie was always pampered with the full pornstar treatment; throated to the hilt, tongue on the balls, rough face fucking even at times, with all the spit and noises and moans that came with it.

"Urghhllchh! Urghllchh! Urughllchh!" went her throat as she impaled her face on his shaft over and over. She tried to look up, to give him a fake pained expression of struggle - the "I'm taking this cock just for you, Daddy" look - but Reggie's eyes were closed.

There were times when he finished in her mouth, but today, the thrust of his hips matched the pace of her mouth and she knew he wanted to fuck.

She detached her mouth from his dick. Even at 4 inches it stood veiny, flushed and proud at the face excavation it had been subject too.

"You want to fuck me, baby?" She asked.

Reggie barely nodded.

She stood up, opened the top drawer of the wooden dresser and pulled out one of a hundred condoms that lived in there. Tearing off the wrapper with her teeth, she rolled the sheath down his length, letting it attach at the base with a hollow smack.

She lay on the edge of the bed, opening her legs wide and bringing her knees up towards her head. She had already lubed herself up a few minutes before his arrival, and her pink pussy glistened with artificial wetness. This was it, the illusion bared.

Reggie's thumb found her pierced clit as the head of his cock probed at her entrance. The other hand placed flat on her thigh, he began to sink effortlessly inside her. She would have been lying if she said she didn't feel pleasure from her work, but it would have taken a great deal of effort to cum from fucking Reggie.

Nevertheless, the gentle friction back and forth on her clit was pleasant enough, and he was all the way inside her now, as far as his little cock could go. He rocked back and forth, in and out, and his breath quickened.

Cherry moaned softly, whispering sweet nothings to the old man and biting her lower lip hard so that the piercings stuck out at weird angles. She tried her best to maintain eye contact, she felt this hurried guys along naturally, but his eyes were all over her.

The sticky sounds quickened as he threw his cock into her wet hole. His body crashed against hers and she opened her legs wider, hooking her arms around the back of her knees and pulling herself wide open for him. She was folded up like a pretzel, but he was not big enough to do any damage to her cervix. The guy could go to town on her if he could manage it.

"Cum in me, baby," she begged, "oh honey, please give me that cum! That's right, fuck me good. Fuck me deep!"

She laid it on thick, and it worked. The man entered some sort of spasm, grunting as his pace became jagged and then slowed. And that was it. The first one of the day sorted.

Cherry left plenty of time between clients and preferred a quality over quantity approach to prostitution. She charged accordingly. She often enjoyed smalltalk in the moments after sex, maybe even a cigarette, but Reggie had pulled off the condom and thrown it into a bin by the bed in seconds. He began to get dressed in silence.

"I'll give you a text about next week," he said, buttoning his shirt.

"I'll be thinking about you, baby," she managed, before he scooped up his coat and zoomed out of the room.

*

11:00

With Reggie finished up in about 15 minutes, Cherry had time to treat herself to an orange and apple smoothie, read a magazine, check Facebook and Adultwork, and clean herself up for the next appointment.

11am came, and there was no sign of her client. He was a first timer, with her at least, who addressed himself in texts as Simon. She figured he was a no show, which was a fucking disappointment - her next client wasn't due until 3pm. For fuck sake.

The frustration was short lived, however. Her phone beeped at 11:02.

"I'm so sorry, but I can't find the apartment, can you help me?"

Cherry read the text aloud, before laughing.

"Fucking idiot," she said to herself.

She replied: "it is safe to ring you?"

He rang her in response. He had a thick accent, and it took a few times repeating the instructions for her to get it across. He didn't sound like he was from around these parts.

Eventually, at 11:16, the knock came at the door. He'd booked an hour, of which he would have usually lost fifteen minutes of, but Cherry was in no rush.

Opening the door, her jaw hit the floor.

Simon, if that was his name, was about 6'7, thick and musclebound. His skin was as black as night. He had narrow brown eyes set deep into a serious face, which was framed with a standard issue military style haircut.

"Hi," she said, weakly. He was the biggest man she had ever seen.

"'Ello, darlin'" he purred. His voice was gravely.

She invited him in and shut the door silently behind him. She smiled to herself. For all purposes, Simon was rather handsome. Cherry couldn't help but think why such a man, who could surely pull his fair share of attractive women, chose to visit an escort. Sure, gone were the days of whores catering just to the anorak crowd, many different men - and women - visited prostitutes for a myriad of different reasons. But that didn't stop her thinking.

"Is this your first time with someone like me?" She asked, as they sauntered into the living room.

Simon seemed quite interested in the decor.

"Yes, it is," he said.

"And is it... your first time... in general?"

Simon laughed heartily. It boomed around the apartment.

"What do you think, little lady?" He asked.

She responded with a smile.

She led him to the bedroom, where he was prompt with presenting the money. Sometimes, extracting the cash from newbies was difficult. They did not know the etiquette.

Again, she slid the silk slip off her shoulder and it dropped to the floor.

Simon sighed a hungry sigh as he devoured her with his eyes. He was going to fuck the shit out of her, she thought.

"Take off your clothes," she ordered.

He peeled off his shirt, revealing a rock hard set of abs. Damn. She dropped to her knees, unbuckling his belt, tearing at the zipper, loosening his jeans and boxers and yanking in one swift motion.

She took an awkward step back, shifting on her knees.

"Fucking hell, mate," she said.

Simon laughed heartily once more.

She had never seen anything like it, and Cherry had seen her fair share of dicks. It was beyond massive. Her brain was probably over-calculating but she could of sworn it was a foot long, and as thick as any soda can.

"I mean, don't get me wrong," she said, climbing to her feet, "I'm very, very fucking impressed, mate."

She crossed her arms and scratched her chin, tilting her head to one side as she studied his member.

"But, I have no idea how I'm going to fit that inside me," she admitted.

Simon smirked.

"I get that a lot," he said.

"I guess that's why you're here?" She inquired.

"Oh yes," he said, sitting on the bed, "most women, they see my cock, and they run scared. Not all, but most."

"What about the ones that don't?" Cherry asked, sitting next to him.

"African women can take this dick deep," he said proudly, but his expression darkened as he reached out and slowly ran his hand across her chest, cupping a tit and twisting gently at the nipple, "but Simon likes slim white girls like you, you feel me? Whoever put fat asses on tiny white bitches is God in my eyes."

Cherry amply fitted that description.

She sighed.

"Simon, I'm gonna level with you," she said, standing up, "I want to fuck you as much as you want to fuck me, I'm sure. Shit, the size on that thing, it's a matter of principle. On whatever honour I have as a whore, I want to fuck you, I really do, but I see no way physically how that cock is going to fit inside any of my holes."

"I see," Simon said, dejected.

"If you like, you can take the money back, I'll figure something out," she suggested, "I have lots of friends who do the same work. If you leave the matter with me, honey, I'll find you a white slut who can take that thing?"

Simon seemed to mull this over.

"Ok," he said, "but keep the money."

"I can't," she protested, as much as it pained her to give it back, "I haven't done anything."

"Use your hands," he proposed, "and your mouth, if your can. Simon needs release."

She smirked at the man, placing the cash back on the dresser.

"You want my little white slut mouth on that massive cock?" She asked, padding slowly towards him.

"Yeah, that's right," he groaned.

She took him in her hand. Her fingers barely wrapped around it, even when semi-erect. She stood there before him, jiggling her tits and slowly jerking him.

"You big black cock is much too big to fit in my tiny white pussy," she purred, "I wish I could stuff that cock deep in my holes, but it's far, far too big for me."

He hardened in seconds.

"Get your mouth on me, bitch," he spat.

"Oh God yes, Daddy," she sighed, falling to her knees, "fucking dominate me with that thick black cock."

On the downstroke she made a point of pulling back the skin so that the massive mushroom head stood proud and firm. Gobbing up some spit in her mouth, she planted a wet kiss on the underside of his glans, marvelling how the cock was bigger than her fucking head.

She tried to take it in her mouth, and whilst she could just about get her mouth around it, she was afraid to press down too much and catch him with her teeth.

She stroked him wildly, as he lay back on his elbows, looking down at her on her knees between his legs, wrestling with the python that nested there.

"You wanna cum on my face, Daddy?"

Simon laughed.

"I ain't your daddy, bitch," he said, "I'm your nigga, slut."

"Yes, baby," she breathed, running her tongue all over his cockhead.

"Say it," he demanded.

She looked up at him, uneasy.

"I mean it, bitch, say it," he repeated, "you know what I mean. Say it!"

She felt quite small. This was out of her comfort zone.

"Cum on my face, nigger," she said quietly.

Simon laughed.

"Bitch, don't be so polite about it," he roared, "beg for it."

She jerked his massive cock.

"Cum all over my fucking face, nigger!" She screamed.

"Yeaaah," he groaned, "that's what I'm talking about."

She was about to go back down onto the head, but Simon exploded, thick globs of pearly white cum shot into her face. A stream shot across the bridge of her nose, thankfully missing her eyes. A small amount got her mouth, but the final spurt landed across her chin, and trickled down, droplets pooling onto her tits.

"Damn, girl," he said, sighing heavily, "don't be so uptight about that shit. You did good, though."

He got dressed as she ran to the bathroom to clean up. She offered him a smoke on her return, but he declined. He sat in the kitchen drinking a Sprite as she smoked on the balcony. She realised, prodding at her forehead as the ciggie burned, that she had missed a bit of cum which was glued to the corner of her face. For fuck sake.

She came in off the balcony as he cracked the bottle down on the surface of the counter.

"I like your attitude," he said, refreshed, "and I like your face. I would like to return, if you can find another woman to help you with this." - He grabbed at his crotch.

"I'll see what I can do," she said.

*

13:00

Her phone had beeped about half hour after Simon had left. She had been lounging, feet up on the sofa, watching daytime soaps and bitching with her friends on Facebook, when a text from Karen came in.

She was in town on a meeting, and was keen to be able to see her favourite escort. Likewise, Cherry found Karen to be one of her favourite customers. Luckily, Cherry was wide open until 3.

1pm rolled around and the door bell rang. Seeing as she had got them out already for her 15:00 appointment, Cherry wore the brutal leather boots over her stockings. They had full chocks on the bottom; hellish chunky bases that added another two inches to Cherry's height, and they came up above her knee in a series of buckles and straps. Instead of her silk night gown, she now wore a petit PVC top to cover her chest.

"Karen," Cherry acknowledged, upon opening the door.

"Good afternoon," the women said politely, ducking into the apartment, "thank you for seeing me on such short notice."

Karen was a woman that always looked tired. She was a dirty blonde who always seemed to have on some variation of pinstripe business attire. She had a bit of cushion around the hips and thighs, and dark circles around her eyes.

Karen had been in meetings all morning and wanted to shower before the session began, so Cherry once more found herself out in the cold, smoking on the balcony in full fetish gear. She wondered if anyone could see her.

Karen returned from the bathroom with a towel wrapped around her and her hair damp. She smiled nervously, and headed for the bedroom.

"No, not today," Cherry barked, "get on the floor by the coffee table."

Play time had begun.

Cherry watched as Karen shuffled nervously over to the main area in the open living room. She wondered quietly to herself about how old the woman was. Early 40s maybe? It was hard to tell.

"Lose the towel," she ordered.

Lose it she did. Unhooking it, she tossed it over the arm of the sofa. She had huge, drooping tits and a belly that could have done with a few months in the gym. A patch of dark fluff sat at the top of her legs. Karen wasn't an ugly woman per se, she just seemed far too busy to look after herself.

"On your knees," Cherry commanded, marching on over slowly from the balcony door.

Karen obeyed.

"Get down on all fours, like a dog,"

Again, the woman did exactly as she was told.

Cherry stopped above her. She looked down on the shivering mass of flesh that lay on the floor, and put a boot into her shoulder.

"From this moment forward, I shall address you as Fuckpig," Cherry explained, "and after every time you are addressed as such, you will respond with "yes mistress." - do you understand me clearly, Fuckpig?"

"Yes mistress," Karen, or Fuckpig, said into the floor.

Cherry let the silence develop, before ordering: "Lick my boots clean, Fuckpig."

Karen went to get up, but Cherry pushed weight down with her boot.

"Stay down,"

Karen was silent.

"Good piggy," Cherry said, "you'll turn your head and lick from the floor. You shan't get up until you are commanded to. Do you understand, Fuckpig?"

"Yes mistress."

She took her boot off Karen's shoulder, and placed her foot down next to her head. Karen enthusiastically started lapping at the sides of the foot.

"Get that shit nice and clean for me," Cherry encouraged.

Hands on her hips, she stood there daydreaming for a few minutes, letting the woman live out her fantasy.

"You're a good little foot slave, aren't you, Fuckpig?"

"Yes mistress," she replied dutifully.

"Follow me, Fuckpig," Cherry ordered.

She turned and took a few steps towards the couch, before slowly lowering herself onto it. She made sure to cross her legs slowly, allowing Karen a tantalising glance at her pussy, and allowing the boots to slide over each other slowly. The material creaked and groaned as she moved.

Karen crawled towards her.

"Unbuckle my boots," she said, "they are starting to sweat too much."