Cherry on Top

Soundlessly, the naked woman started scrabbling at the clasps on Cherry's right leg. She worked the connections apart, and tried to pull, but the boot would not give way.

"Gently, Fuckpig," Cherry warned, "I am not some shop mannequin or nightclub tart to be roughly undressed; I am a porcelain doll of perfection and you need to treat me as such."

Karen began to mumble an apology but Cherry put her boot back to the woman's shoulder and forcefully kicked her across the floor. She tumbled over in a crash and lay there in a heap.

"Try again, Fuckpig, and do it properly this time."

Karen crawled, pathetic and weak, and attempted to remove the boot more gently this time. With a little patience, it slid easily off Cherry's slender leg, still clad in the black stockings. The large boot fell to the floor.

"Pick it up," Cherry said. The woman scooped it up in her hands, sitting there on her haunches waiting like a dog.

"Smell it," Cherry went on, "put your nose inside the boot and take a nice big whiff."

The woman did as she was told, and inhaled deeply. On the exhale, she shuddered. Cherry thought the woman was about to orgasm.

"How does my foot sweat smell, Fuckpig?"

"Divine, mistress, simply divine."

Cherry had her repeat the whole process with the left foot, before ordering her to lie flat on the floor beneath her, where she teased the woman's breasts and face with her feet. Every so often, she would stretch down and rub at Karen's cunt with her right foot.

"Times up, Fuckpig," Cherry informed her regretfully, "get up, get dressed, and fuck off."

Once Karen had returned from the bathroom with her clothes in hand, Cherry had removed the PVC top and slipped into her silks. She chatted idly with Karen, who made some effort at least to contribute to the conversation.

"I really love what we have going here," Karen had said, "I wish that we could take it further, really get under my skin and make me a live-in slave, but with work and all, I don't know if that is possible."

Cherry knew that work wasn't the real issue. Karen was a busy woman, this was true, but something told her Karen wasn't completely ready to submit for long periods of time. Cherry too, who often dabbled in BDSM several times a day, had to admit she would struggle to keep the session fresh for longer than a few hours. She offered domination because her clients demanded it, not because she was particularly good at it. Cherry enjoyed the switch up, but was more often than not in submissive or compromising scenarios when it came to the majority of her customers.

"We'll work you up to it," Cherry explained, rubbing Karen's shoulders, "maybe we should try and organise a few hours first, or maybe like as long a working day? 6 to 8 hours should be a nice trail run, before going the whole hog."

*

15:00

Ian was Cherry's second dom-related client of the day, so the leather boots and PVC top went back on after half hour or so of lounging about reading a crappy tabloid magazine. Cherry couldn't decide which it was that she hated more; tabloid gossip magazines, or her addiction to them.

Ian was a regular, and one of her oldest customers. He was a used car salesman in his mid to late 30s. They had a thing going where they would carry out the entire session in silence. He would come, he would be abused, and he would leave. There was never any fucking. Ian often only booked half hour sessions, something she usually discouraged for domination or BDSM play, but Ian was a regular. While he didn't stay long, he visited often, sometimes twice a week.

They stood across from each other in the bathroom, her in her PVC and leather and he completely nude save for his silver wedding band, which he had never bothered to conceal from her, like many other clients. He was a fairly regular looking bloke, with regular guy hair and a regular guy cock. His stomach had started to grow a little in recent years, as had his love handles.

Cherry did her best intimidating stare, using her eye lasers to wear the man down. Ian did not break the gaze with her, not even once. The silence was deafening. Cherry tensed up and flexed the muscles in her right leg, priming herself for what she was about to do.

In a swift motion, her leg shot out, her thick boot kicking Ian square in the balls with incredible force. The man gasped in agony, buckled, and fell to the floor in a heap, howling through gritted teeth.

This continued for quite some time. This week she had really caught him with a fucking shiner, which she was rather proud of. It was the same ritual every week, Ian was strange like that, but nevertheless Cherry found herself enjoying the sessions.

As if on cue, as the pain no doubt subsided, Ian began to shuffle towards Cherry's feet, dragging himself across the floor as if he was mortally wounded. He wrapped an arm around her leg, and pushed himself over onto his back, breathless. He lay there, staring up into her cunt.

Cherry widened her stance a little, and pressed down. A thin stream of clear piss started to trickle out of the folds in her labia and drip down onto the injured man below. He opened his mouth wide, sticking his tongue out eagerly and closing his eyes. The trickle became a hefty stream which splattered across his face and torso. The man lay there, writhing and moaning in the torrents of piss.

It had splashed back on her boots, which she wasn't best pleased about. The stream reduced to a few final drops, and Cherry marched out of the room. She was having a cigarette on the balcony when she heard Ian leave several minutes later.

Domination could be easy work if you could get it. But now, she had to clean up all that piss whilst mentally preparing herself for the anal which was to come.

*

17:30

Tears streamed from her eyes as she withdrew his cock from her throat. She coughed violently, spit and drool hanging from the hole in her face. He had a grip on her ponytail, and getting up for air was difficult.

She'd gotten a good gulp down her before he started smacking her in the face, making her cheeks red raw.

"There's a good girl," he taunted.

His tattooed arms were muscle bound, which made resisting his movement difficult. He as much as forced her head back down onto his cock, and thrust it into her. It struck the back of her throat repeatedly, as if he was trying his damnedest to push through the blockage.

Cherry coughed, and gagged noisily, hacking up bile through her nose as she slowly drew over the cock once more. Her eye makeup was streaming down her face.

He picked her up and threw her onto the bed, her tits flopping everywhere as she flew through the air. Her arse wobbled like a jelly as she hit the sheets face down.

"Present yourself properly," he ordered.

Cherry took several deep breaths, before pushing her behind up in the air, and bringing her knees up as close to her tits as possible. She could feel the cool air caress her exposed holes.

He smacked her ass hard. She yelped. A fat gob of spit landed squarely on her arsehole, and a finger quickly probed at her hole.

She had taken the liberty of lubing up prior to his arrival, but you could never have enough when it came to assfucking. Nevertheless, she was still already amply greasy down there, enough for him to slide a thumb in undeterred.

He pushed his thumb in and out of her arsehole multiple times, slowly at first but then with increasing speed. She felt something else. It was the thumb of his other hand, he was working that in to her too. He began pushing each thumb inside in turns, before he pressed both inside at once, her ring slowly adjusting to accommodate the extra digit.

He hooked his thumbs inside of her sphincter muscles and firmly tugged to each side. He encountered some resistance, so he curled his thumbs a little harder. It was uncomfortable, but it did not hurt.

"Push," he said, between heavy breaths. He was clearly enjoying himself.

Cherry made to bear down, as if taking a shit, and the muscles in his hands loosened somewhat. He doubled down on his own grip and pulled her arsehole agape. Cherry silently prayed that her pushing down wouldn't cause her to shoot a wet fart at her client. He would most likely just laugh and smack her on the arse, but she would also die of embarrassment.

As if reading her mind, he removed his thumbs and gave her a great thwack on the right cheek. She exhaled and gave a jump. The blow rippled out on the cheek. She knew what was coming next. Afterall, she'd been here before many times.

"Lube," she said into the sheets, "lots and lots of fucking lube, you hear me?"

There was the faint smacking sound of a condom being let go of at the hilt of his dick. Another blow came down on her right asscheek.

Cherry closed her eyes and gritted her teeth.

"Fucking Christ!" She swore.

"Don't tell me how to fuck," he snarled.

Slippy sounds came from behind her, as if someone was stirring mac and cheese with a spoon. He was - hopefully - applying a large amount of silicone lube, wanking himself inside the condom with the liquid on his hand. She had placed a great big tub of Lubrifist on the top of the dresser, with the lid off. No bigger hint could have been left.

The tip of his cock was rubbery, wet and cold as it pressed against her loosened hole. These were good signs that he was suited up and slippery enough to enter her without any serious pain occurring. Nevertheless, Cherry closed her eyes, bit down on her lower lip and focussed on her breathing. She was as ready as she'd ever be.

She felt him press into her. Her sphincter widened slowly to accommodate him. His fingerwork had loosened her up a bit, and by pushing down she opened the muscle as much as she could. The lubed up head of his cock popped into her ass, and her body adjusted around it.

Hands gripped at her waist as he worked his cock into her gut. Sliding in and out, with each stroke her pushed a little further inside her. So far there had been very little pain, but in general she found anal sex to be very uncomfortable. Even as a sub in her personal sexual life, Cherry took no physical sexual pleasure from the act. Maybe the pleasure from being owned, fucked and dominated, sure, but from the anal sex itself? Not so much.

He growled like an animal as he worked her hole. Cherry started some low deep moans of her own, trying to make herself sound more vulnerable. As soon as her ass was fully adjusted to his girth, she would employ her own tactics to milk his cock dry in a shorter length of time. For Cherry was always on top, even when she was on the bottom.

He withdrew and stopped fucking. Hands gripped hard at her butt cheeks, spreading her wide. He was gaping her. There was something about men who were into assfucking, she thought. They just loved to admire their handiwork. Nobody ever did that to her pussy.

He slid his whole cock back into her butthole in one smooth motion. Air farted out the sides. She was more opened up than she'd initially thought. It was time to speed this along!

A gay friend had once told her the "secret" to anal sex. She'd laughed it off initially, but then when she'd actually thought about what she'd been told, it made all kinds of sense.

As he thrust his cock into her, she pushed out, as if she was taking a shit. Her sphincter muscle, already adjusted to the size of his cock, opened all the more to allow him to throw his meat into her with ease. And then, as he withdrew, she tightened and squeezed her arsehole shut as much as she voluntarily could.

"Damn girl," he said, smacking her raw ass again.

It worked every time, Cherry thought.

It took a few goes to match his strokes, but before long they were in a sloppy, wet unison of assfucking. Push down on the penetration, squeeze in on the withdrawal. And on and on.

Joel, her client, was getting rather animated. He slid out of her, groaning as he did. He placed a hand flat on her pelvis and pushed her ass down towards the bed.

Cherry let out a ripping fart, as all the air he'd fucked into her gaping hole escaped in one go. Joel laughed, a sleazy perverted gurgle of a laugh, and smacked her ass, this time thankfully on the left cheek for a change.

He slid back inside her and fucked her butthole with a vengeance. She struggled to keep up with his strokes, but the volume of his moans and the new depths of his thrusts told her that he was cumming. Like that, it was over, his pace slowed considerably and his erection shrank.

Cherry rolled over and grabbed some kitchen cloth, holding it to her battered hole, to catch anything that would run out of her. He was protected, so the usual sticky mess that followed was considerably less, but plenty of lube would find its way out over the next few minutes.

Joel was as sweet as they come, that was, after they had finished fucking. He'd brought her flowers, chocolates and prosecco. There was something about the sweetness of his personality; Cherry thought it was as though he was almost sorry for each time he treated her like meat and paid to turn her ass out. That was, until a few weeks later when he showed up again, rock hard, wanting to bust open her holes once more.

It was dark outside now, too dark to stand on the balcony and really see anything, so after Joel left, Cherry locked up for the night and removed her make up.

Exhausted by the whole ordeal, Cherry lowered her sore bottom into a hot bubblebath and let the warmth of the water caress her into relaxation. After a day of not eating in order to take a care-free anal pounding, she treated herself to a pizza, which she ordered online using her phone.

She slid down into the bubbles until only her head remained above water, and sighed heavily. Soon it would be time to sleep, and tomorrow she would do it all over again.