Sylvia's Boy Toy Ch. 01-02

Story Info
A face-sitting whore bites off more than he can chew.
10.8k words
4.64
13.4k
16

Part 1 of the 2 part series

Updated 06/11/2023
Created 09/29/2022
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Author's Introduction

Thank you dear reader for taking the time to check out this story! I am not a professional writer by any means, and this is my first attempt at writing anything. I appreciate feedback, both praise and criticism. Please rate and comment to your heart's content! I love comments, so let me know if you found this hot!

Setting: This story takes places in an alternate universe version of the United States in an unknown city around the present day.

In this story, brothels are not only completely legal in the United States, but are commonly found and visited by adults across the country. Medical advances have led to the chances of an accidental pregnancy to be around 0.01% or lower, even with unprotected sex. All STD's have been cured and are no longer a threat to the general population. Women in this futuristic world are much more sexually driven, being equal or even more direct in regards to their sexual needs than men. Because of this, women are also frequently found at brothels as regular paying clients, rather than as prostitutes. I hope you find this story to be a pleasurable read, in more ways than one!

Hope you enjoy!

- CunnilingusKing93

Chapter 1 - The Offer

"Oh my fucking God, yes!"

Josh gripped fistfuls of the sheets as the curvy woman above him wildly bucked her hips. He felt her ass press even harder against his nose and forehead. Tanya pushed herself downwards with each roll of her hips, squirting into his mouth.

He hurriedly swallowed three times as her juices flowed freely into his throat. He enjoyed her taste, but knew from past experiences to swallow her offering quickly - she always seemed to produce a massive amount of ejaculation. Truth be told, she squirted more than just about any woman he had ever met, and by far the most of his regular clients. If he didn't swallow, he might drown in it.

He chuckled inwardly as Tanya rode his face through her climax. He mentally pictured a news article titled, Male prostitute dead - drowns in ass and pussy. Most straight men would say that's one of the best ways to go out of this world, but Josh was not interested in dying today. He had one more client to see tonight, and his mortgage had to be paid by Thursday. And so he swallowed the last of her cum as Tanya rode out her orgasm, her pussy and legs quivering. She had cum at least 9 or 10 times during their 45 minute session. Her body was drained, at least temporarily. She had an incredibly high sexual appetite.

Tanya continued to sit on him long after her orgasm subsided, winded and breathing heavily. He waited patiently for her to collect herself, but Tanya seemed to be in no hurry to remove her ass from his face. His high school and college career as a competitive swimmer was ideal for his line of work - having excessively strong lung-power certainly helps when women sit on one's face for extended periods of time. Even so, he had to admit the lack of oxygen was starting to get to him. He ignored the burning in his lungs as he slowly ran out of air. With a grunt, she finally climbed off of him and laid by his side on the bed. Both of them were panting slightly, her in the afterglow of sexual excitement, him from holding his breath. Not that he wasn't sexually excited himself. On the contrary, his cock was stiff and pointed upwards towards his belly in a full erection. Tanya however was not paying any mind to Josh's sexual needs. He had hoped for it of course, but he did not truly expect her to. This was her time and she had paid for his services.

A client could suck him or jack him off if they desired, but they were not required to do so. Some did of course, especially if they got a craving for it during a session. He knew which of his regular clients could be counted on to reciprocate his services once they were horny. In fact his client after Tanya was one of them. Laila gave immensely pleasurable blowjobs, and he knew he would get a wonderful release from her soon.

Some people might find his job to be a dream come true. As a male prostitute, he had access to all the pussy and ass a man could want, and then some. And of course there were some times that he felt like a very lucky man indeed, as the work was often lucrative and pleasurable. This was not always the case, however. A smaller number of clients not only ignored his sexual needs, but abused them. Some clients seemed to get off on teasing him sexually to the point it could be called torture. He hated those women, although he saw small handful of them every week. Such a girl might reach down while riding his face, and stroke him all the way until he was on the brink of an orgasm. Then she would remove her hand with a cruel laugh, causing him to buck his hips and groan longingly in protest. Then the power and control they held over him would make them cum. Hard. Josh supposed most of the women who did this to him had a history of bad sexual experiences with their husbands, boyfriends, and/or former lovers. He believed these women took out these frustrations on him, wanting to see someone suffer or pay the price. Most clients however, like Tanya, simply left his cock alone.

"Wow Romeo," Tanya gasped. Her large tits glistened with sweat and were still heaving up and down. Looking at this erotic view made his cock twitch. She had used his stage name - none of his clients knew his real name. "You and that tongue of yours really outdid yourselves this time. I don't think I can take any more. Thanks for such a wonderful time. Same time next week?"

She gave him a smile, which he genuinely returned.

"It was my pleasure. And yes, of course we can meet next week."

Tanya climbed off the bed and bent over for her clothes. Josh admired the round shape of her bottom and the swinging of her breasts as she did this. He didn't know exactly how old Tanya was, but she couldn't have been any older than her mid-30's, probably younger. Her stomach had a small pudge, but otherwise she was curvy in all the right places. Both her breasts and ass were quite large and round. Her nipples were also large and quite puffy. She must have known he was checking her out, because she took a little longer than was strictly necessary to pull her panties up. She turned her head and smiled at him knowingly, enjoying his lustful gaze as she slowly got dressed. His cock twitched again.

It was an agonizing tease, watching her put on her clothes. Why exactly is watching a woman dress just as thrilling as watching them strip? He pondered this as she put on her matching green bra and panties. Half dressed, Tanya excused herself to freshen up. Her legs wobbled a little as she walked, but she gave him a small show all the same, wiggling her butt as she went. She knew she had a great ass and loved his attention.

Josh sighed heavily and slid off the bed to his feet. His erection was still standing tall and proud, aching with need. It bounced up and down a little as he walked to the separate sink in the room to brush his teeth and wash his face.

Standing in front of the mirror, Joshua Arnold Cardone paused to stare at his reflection. Staring back at him was a muscular and fit Italian man of 30 years of age. Standing at just over 6 feet, he was ruggedly handsome, with a strong jawline and a good-looking face. His eyes were a blazing blue, his short hair a light shade of brown. His skin was perfectly tanned to golden perfection. Some people said he looked a little like an Italian Jensen Ackles. His shoulders and chest were broad and muscular, his abdomen sporting a 6-pack. His legs and ass were also muscular from his regular workouts 6 days per week. Joshua had always been an active man, but his physique had reached new heights when he had thrown himself completely into a life of fitness and sex 5 years prior, eventually finding himself working in the brothel as a oral sex prostitute for the last 2 years. When not at the gym in the morning living off a diet of protein, he could be found here in the evenings, living off a diet of ass and pussy. His throbbing cock was fat and as thick as his wide wrist, with a single vein popping out distinctly along the side of his just over 7-inch shaft. When erect as it was now, his penis curved slightly upwards. His balls were large and heavy, and when he came it was usually in abnormally large loads. He shaved or waxed every off hair of his body apart from his head, making him smooth all over. He was a gorgeous man, a sexual plaything for women.

Josh also possessed an extremely long tongue. This came in handy as he could penetrate assholes and pussies with ease. And in the last two years he had become an expert in using his tongue to make women cum. He was really fucking good at it.

With his good looks, outstanding tongue skills, and strong lung power, he was one of the most popular prostitutes in the brothel. However, there was a limitation in place holding him back from making serious money. The biggest problem was that the brothel's boss did not allow the male prostitutes to fuck the female clients, in any capacity. Not even anal sex. It wasn't illegal, since the other brothel across town permitted their clients to get pounded to their heart's content. Josh had tried to find work there many times, but each time he tried he had been declined. He wasn't sure exactly why, and he hadn't asked why he was rejected. After trying for a good year or two, he gave up and shrugged it off as bad luck. He told himself it simply wasn't meant to be, and came to work at this place instead. Unfortunately this brothel saw way fewer clients, because women often want to get fucked, and the other establishment could provide that need. He had asked his boss why it wasn't allowed on the day he was hired, but all she had said was, "We do not want to be held responsible if a client gets pregnant. It's a lot of mess and isn't worth the hassle." But this didn't make sense either, since the chances of a woman getting pregnant was small if they took "the pill." "The pill" was widely available, affordable, and very rarely ever showed any side effects for women, so what was the problem? 98% of teenage and adult female women these days took the pill already unless they wanted a baby or had reached menopause. Also, her pregnancy excuse didn't make sense in regards to allowing anal. When he pointed this out to her, she ignored his question and promptly changed the subject. He hadn't asked since.

I really should invest stock in Crest or Colgate, he thought as he reached for his toothbrush. Josh probably brushed his teeth anywhere from 4-8 times a day, and sometimes more, depending on how many clients he had. He always needed to be clean and ready for the next woman paying for his services.

He was swishing around Listerine when the bathroom door opened. From the sink mirror he saw Tanya stood behind him, fully dressed. She clearly tried to dress modestly, but failed as her breasts were too busty to hide completely. They stuck out like cantaloupes on her chest. Her dirty-blonde hair was pulled back and her makeup touched up, but she still had a slightly windswept look and her cheeks were flushed.

She sauntered up behind him and gave his ass cheek a playful squeeze followed immediately by a smack. He spit into the sink.

"Thanks again, sexy. I'll see you next week."

He turned to face her, careful to stand slightly apart from her so his erection would not brush her midriff.

"I look forward to it."

Tanya reached into her purse, pulled out an envelope, and placed it into his hand. He accepted it gratefully.

"Your fee. I also included your tip."

"Thank you, Tanya dear."

"Have a good night, Romeo. Don't work that tongue too hard the rest of the night."

"I'll try not to," he chuckled softly. "Good night, Tanya."

He glanced at the clock. It was 9:58. Laila would be here in 2 minutes. Tanya turned to leave, stopping only to blow him a kiss from the door. He pretended to catch it. She left.

Josh let out a soft groan the moment she closed the door and looked down longingly at his erection. He needed release, and soon. He desperately wanted, no needed to cum, but there was no time - Laila would be here any minute. With her hunger for dick, he believed she would prefer to find him hard like this anyway, and as long as he did his job, she would take care of his needs.

Laila was one of his favorite regular clients. She had an angular but pretty face, with a long nose, deliciously plump DSL's, and big brown eyes. He never asked what her race was, but he supposed she was at least partially Arab/Middle-Eastern. Her prodigious skill with her tongue also rivaled his own. Her body was lean and fit. His cock twitched again painfully as he imagined her naked at the foot of the bed. He pictured her petite and athletic figure, with dark tan skin and lust burning in her eyes. He pictured her perky breasts with their pointy dark brown nipples, with surrounded by tiny light brown areoles, with small bumps orbiting each long nipple. He had jokingly asked her once if the bumps were braille for "suck here." She had laughed heartily at this comment and had happily cupped one of her breasts towards his mouth for him to suckle. His imagination wandered to her amazing abs that she worked so hard in the gym to perfect, to her tight pussy, down to her long thin legs. She didn't have much of an ass, but the enthusiasm she had for his cock was undeniable. As an added bonus to her cock sucking skills, she also happened to love the taste of cum. His cock hurt at the thought of her swallowing his load. He felt like he was about to burst.

He opened the envelope Tanya had given him and peeked inside. Inside was $400 - $300 for his fee, $100 extra as a tip.

Enough here to pay The Bitch for the night plus a little extra, he thought. The Bitch was his boss and the owner of the brothel. Her nickname was commonly used amongst the male prostitutes, although none of them actually called her that to her face. Her real name was Sylvia, yet she forced all of the workers under "her roof" to refer to her as "Mistress." Josh refused to refer to her as such.

Josh hated just about everything about her, from her sadistic outlook and treatment towards men, to her psychotic behavior. She was also exceptionally greedy and charged him heavily for the use of his room every night. The bitch relished in the torture of males and loved getting off on it. But what he despised about her most of all, was that she had the most perfect body he had ever seen. It was as if a man's dick had created her, had built her specifically for sex. She also knew perfectly well how stacked she was, and she exploited it to the extreme. Why should such a shitty person get to be so god damn hot? The injustice was infuriating beyond belief!

Josh placed the envelope in a dresser drawer, closed it, and turned to the bed to straighten the sheets and pillow to prepare for Laila. When finished, he sat upright against the headboard and waited for his favorite cocksucker to arrive, staring down at his throbbing, aching dick. It was really becoming painful now. He yearned for release, to feel her lips and tongue swirl along the swollen head of his shaft...

He jerked his head up swiftly as the door to his room suddenly swung open. He knew it wasn't Laila, as she would have politely knocked first. He knew exactly who it was because only one person he knew would barge into his room without knocking...The Bitch.

Sylvia's entrance was preceded by her colossal tits, protruding proudly from her chest, seeming to defy gravity. A sheen of jet black hair hung loosely to the square of her shoulders. She had a stunningly beautiful face, with large dark eyes, a cute button nose, and dazzlingly white and even teeth. She was wearing purple lipstick and a broad stroke of purple and black eyeshadow. She also wore long eyelashes. Her pale and creamy complexion contrasted starkly with her all-black lingerie and multiple tattoos all over her body. While already somewhat tall at around 5'7 or 5'8 or so, she appeared even taller than she actually was due to the black high-platform stilettos she was wearing, complete with black fishnet stockings and garter belt. Her legs were long and shapely, the kind of legs a man might desire to wrap around his waist. She was wearing a tight leather corset, covering her soft and tiny waist. The corset left her round and enormous breasts completely bare, with large, bright pink areoles. Her pointy and erect nipples were a slightly darker shade of pink - both were decorated with silver piercings. Her leather panties were crotchless, exposing her most of her pale ass cheeks as well as her bald and puffy pussy lips. She had multiple other piercings apart from her breasts: several earrings, a nose stud, her bellybutton, and the hood of her clit.

With her pale skin, ginormous breasts, and gothic-whore style, she reminded him of the pornstar Larkin Love. Her flawless figure however, more likely resembled the body of YouTuber/model Erin Olash. It was as if she was a cross between the two women, and yet she was more lush and ripe than either of them. It was common knowledge that the legendary Larkin Love's huge tits were fake - Josh knew Sylvia's knockers, similar in shape but even larger than Larkin's, were quite unbelievably real. And while Erin Olash certainly had a great ass, it couldn't hold a candle to Sylvia's perfectly-shaped bubble. She simply oozed with sex appeal from head to foot. Too bad she is also soulless, Josh smirked.

To complete this sexy ensemble, she carried a small whip in one hand - in the other, a leash. The leash was tied to the collar of tall but skinny young man being pulled into the room behind her.

Her personal sex slave. Every month or so she got herself a new one. She had been this way for as long as he had known her. In his past two years of working at the brothel, Josh had seen at over two dozen different people connected to a leash in her hands, and he knew there were others before they had met. She always assigned her slaves a number - her slave count. He wasn't exactly sure how old she was, but she looked quite young, perhaps in her early 20's. It was quite possible she had started this routine as young as her late teens. Most of these poor, stupid bastards were men, but a handful of them had been women. Sylvia was bisexual, but seemed to have a preference for males slaves. Her current slave was wearing nothing but the collar around his throat and a metal chastity cage around his groin. Why would anyone willingly put on one of those? He thought with bewilderment, staring at it. It looked extremely uncomfortable. The cage seemed to be especially small - the man's penis would not be able to become erect inside it. If it did, it would attempt to swell beyond the cage's size and would probably hurt like hell. Which is most likely the point, he reminded himself.

Sylvia halted in the middle of the room and raised the whip. The other man, who had closed the door behind him on his way inside, dropped to his knees quickly at the sound of its crack. He proceeded to crawl on all fours until he was facing her. Josh realized he was wearing an something else as well - a large silver butt plug was shoved up his ass. He didn't need to guess who had put it there. It looked painful.

"May I please eat my dinner now, Mistress? I am very hungry."

His voice was a pleading but gravelly low growl. She stared down at him with a frown. At first Josh thought she would not answer. Yet the man waited and did not look away. Finally, she replied almost nonchalantly, "You may eat, number 39."

He began to lick her. Josh then noticed one of her tattoos - an arrow pointing down to her vagina. Just above the arrow were the words "Your meal." Sylvia gently stroked 39's bald head as if he were a pet and said, "Good boy." He didn't reply but continued to lick her enthusiastically. She seemed satisfied with this response, because she finally turned her attention fully to Josh. Her eyes had quickly glanced up and down his body before doing a double take and landing with a disbelieving stare at his huge erection. She frowned, a furrow creasing her brow. When she spoke again, her tone was icy.