Diary of a Prostitute - Cover

Diary of a Prostitute

by Michele Nylons

Copyright© 2024 by Michele Nylons

Erotica Sex Story: Bored with their sex life and seeking to supplement their income a husband and wife decide to enter the world of prostitution. This is a vignette in the day of a life of a high-class prostitute and explains how a married couple can live happily together while they each have sex with strangers for money.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/Ma   Consensual   BiSexual   CrossDressing   Shemale   TransGender   Fiction   Vignettes   Sharing   Black Male   Anal Sex   Analingus   Cream Pie   Facial   Masturbation   Oral Sex   Petting   Foot Fetish   Leg Fetish   Prostitution   .

Jordan looked at herself critically in the mirror. Her makeup was ostentatious; loud and sluttish. She had gone heavy on the black eyeliner and mascara and used flamboyant eyeshadow, rouged her cheeks to highlight her perfect cheekbones and painted her plump lips with vibrant red lipstick. Her beautiful face was framed by jet-black bangs.

“Perfect,” she smiled at her reflection.

She looked like a whore. But then again she was supposed to. She was a whore.

She took a sip of Johnnie Walker Blue Label whisky leaving an impression of her lips on the glass despite her lipstick being advertised as colourfast. The whisky was just to take the edge off, she didn’t need Dutch courage. Jordan had been a prostitute for long enough that she did not need alcohol to settle her nerves. She did not use drugs.

She checked her appointments calendar in her phone. Her first trick would be arriving in thirty minutes.

Jordan had laid out the clothing she would be wearing this evening on the bed and put away the small suitcase in which she carried the ensemble and hung the clothing she had worn to the hotel in the wardrobe. She didn’t want any evidence of her mundania to spoil any of her johns experience or remind them of her everyday existence. She was supposed to be their fantasy girl after all.

She removed the bathrobe and checked herself in the mirrored doors of the wardrobe and was pleased with what she saw. Her body was trim, her legs long and her ass rounded. At her age, diet and exercise were essential in keeping her figure.

The bathrobe was hung on the back of the bathroom door ready to be used again when needed; it was time to get busy if she was to be ready when her first john arrived.

She stepped into a black satin suspender belt, trimmed with red lace and cinched it around her waist, the garters dangled provocatively down her flawless alabaster thighs. She had already opened the package of Wolford fully-fashioned black stockings and she carefully drew them up her legs, careful not to snag them with her long red fingernails. She clipped the welts to the garter snaps and smoothed out any wrinkles and straightened the seams.

The donned the matching bra and panty set and picked up a short-skirted black cocktail dress off the bed and stepped into it, wincing as she reached behind herself to close the zipper. She stepped into shiny black Christian Louboutin fuck-me pumps and straightened the hem of her dress. The hem rested high on her thighs exposing the dark gauzy welts of her stockings.

The ridiculously short dress would be impractical in any other setting and was likely superfluous but her tricks expected elegance and she always gave them what they paid for. Besides, some of her clients liked to undress her. If she stained the dress she was wearing tonight she would simply dispose of it. Although the dress looked expensive, it wasn’t and Jordan had bought five of them when they came on sale. The Louboutins however were the real thing and her one extravagance.

Jordan advertised the full GFE and that’s what she provided. The full girlfriend experience included kissing, foreplay, oral and unprotected penetration should they so desire. Her job was not only to satisfy her customers’ sexual urges but to pamper them and behave like she adored them. If men just wanted a blow-and-go or a quick and dirty fuck there were plenty of girls on the streets who offered those services.

That is why she used the five-star Ambassador Hotel rather than some no-tell motel flea pit that leased rooms by the hour. Jordan provided her services to men of distinction.

She fitted the silver drop earrings to her ears. They dangled almost down to her shoulders and the faux diamonds twinkled in the ambient light, peeking out from her glossy raven bob. She hung a matching choker around her swan-like neck and bracelets on each wrist. Dousing herself in Dior Poison perfume she was ready and she dimmed the lights and took another sip of whisky.

Her phone pinged. Buddy was in the lobby and she texted back her room number and made sure that the door to her hotel room was unlocked. Buddy was not his real name of course but most of her johns used pseudonyms. They would be horrified if their wives, friends or colleagues knew that they were using her services but they knew that Jordan offered complete confidentiality and discretion.

Jordan was waiting inside the door when Buddy came through it, closing and locking it behind him. He dropped his briefcase on the floor and took Jordan into his arms and kissed her passionately, thrusting his tongue into her mouth and holding her close.

He tasted of breath mints which didn’t quite hide the taste of the numerous cups of coffee he had drunk at work or the illicit cigarette he had smoked outside the hotel. Jordan knew that Buddy worked as an executive in a city office and he stopped at the Ambassador to see Jordan once a week on his way home under the pretext of working late. He was always in a hurry but liked to savour Jordan’s delights for as long as he could during their brief interlude.

“God, I really need this tonight Jordan. Work is chaos and Cindy is refusing sex until I agree to take her to Paris for our anniversary. I told her our anniversary is the week we close the deal with GenTech but she’s insisting we go anyway,” Buddy extricated himself from Jordan’s embrace and struggled out of his overcoat and dropped it on the bed.

They would not be using the bed so Jordan left it there and listened to Buddy, pretending to care about Buddy’s work and marital problems while she poured him a scotch over ice. Buddy never stayed long and he had a ritual she had grown accustomed to. She handed him the drink and he drank it one long swallow and handed her the glass and shucked out of his suit, shirt and tie which joined the overcoat on the bed. He kicked off his shoes and but left on his socks as usual.

His underpants were bulging at the front in anticipation and as soon as Jordan returned from rinsing his glass he pulled her to him and began to kiss her excitedly, his hands gasping her ass and pulling her tight against him. Jordan stood five-ten in her heels but Buddy was a tall man too and he pressed his cock into her belly. His ardour was fuelled by the little blue pill he had swallowed on the way to the hotel. In his mid-fifties with a high pressure job and a much younger trophy wife, Buddy needed all the help he could get.

As his hands slid down her buttocks and found her thighs, Jordan snaked a hand between their bodies and grasped Buddy’s hard cock and freed it from his underpants. She felt him gasp into her mouth as she began to massage the swollen appendage.

“Jeeze, I love those stockings. I bought Cindy two pairs but she refuses to wear them. Says only hookers and showgirls wear black stockings,” Buddy broke the kiss long enough to whine.

The unintentional insult slid off Jordan like water off a duck’s back. Jordan had been called worse. Instead she closed her mouth on his and slipped her tongue between his lips and stroked his cock a little faster, just how he liked it. Buddy pawed at her thighs, playing with her garter snaps and fondling the translucent welts of her stockings. Then his hands cupped her buttocks under her dress, his fingers digging into her black satin panties.

Right on schedule Buddy broke the kiss and placed his hands on her shoulders and Jordan dropped to her knees. She anticipated the next movement in their weekly habitude.

Jordan pulled down Buddy’s underpants and ran her tongue along the length of his phallus. She gathered the sweet dewy droplet of precum and swallowed it before she engulfed his entire protuberance in her mouth. Buddy rested his hands on her shoulders and began to slowly fuck Jordan’s mouth while he gazed down into her pretty visage.

He watched his cock slide in and out of those perfect red lips and stared longingly into her sparkling emerald-green eyes enhanced by the black eyeliner and mascara. Jordan knew that men liked to look at her when she fellated them. It was as much about power as it was sex. When they thrust their cock in and out of her willing mouth, her eyes looking pleadingly up at them, they felt like they owned her.

She used her tongue to lash at his glans, the tip of it tickling his fraenulum, her lips caressing the steely shaft, measuring her progress by Buddy’s jagged accelerated breathing, listening to his gasps of delight and watching the pained expression on his face as his fervour escalated. She cupped his scrotum and gently raked her nails along the wrinkled sac.

“Cindy hands out blowjobs like they are a rare commodity. I get one on my birthday, one on our anniversary, one at Christmas and sometimes if I buy her an expensive present,” Buddy whined.

Jordan had heard this lament before. Many of her tricks complained that their wives either withheld sexual favours or wouldn’t submit to their husband’s licentious demands. It was not her job to comment. Her job was to listen to them and sympathise with their plight while she provided the services that their wives withheld.

Buddy gripped her shoulders a little tighter and she felt his cock begin to shudder as it bloated to full tumescence. Buddy sometimes liked to come in her mouth but usually he wanted to fuck her and this evening was no different. Buddy ripped his cock from Jordan’s mouth and helped her to her feet.

Jordan smiled inwardly. As usual Buddy was in a rush and he would soon be done with her.

He pushed Jordan towards the sofa but she knew that she wouldn’t be reclining on it. Instead she took up her usual stance: arms spread wide with her hands gripping the back of the sofa for support, heels parted, bent over with her ass raised.

Buddy moved in behind her and slowly lifted her dress, taking some time to stroke her legs and caress her plump buttocks. He eased aside the gusset of her panties and Jordan took a deep breath as Buddy slid half of his hard cock inside her then paused.

Jordan gasped which she knew that Buddy would like. All men wanted know that their cocks were big enough to elicit verbal confirmation of their manhood.

“You like me inside you, don’t you, you dirty whore,” Buddy hissed as he grasped her hips and thrust himself all the way inside her moist passage.

Jordan just nodded and pushed back against Buddy, encouraging him to fuck her. It wouldn’t take long, it never did.

Buddy held her tighter and thrust his engorged flesh in and out of her, grinding his pubis into her satin-shrouded globes. Jordan grunted and held on to the back of the sofa as Buddy’s fingers dug into her flesh and his breathing became ragged. She could feel his cock begin to judder and then Buddy pulled Jordan hard against him and ground his groin into her buttocks as he unloaded a week’s worth of scalding semen deep inside her.

She moaned and whimpered and undulated her buttocks, simulating passion that she didn’t feel.

“Fuck me big boy! Make me yours! Fill me with your spunk!” Jordan moaned her well-rehearsed chorus.

She knew exactly what to say to make Buddy feel like the man he wanted be, not the whimpering lap-dog who begged his wife for sex and pandered to her every whim.

The ritual was complete and Buddy clung to Jordan as the last of his issue filled her void.

When Buddy extracted his withering flesh Jordan reached down onto the sofa and snatched tissues from the box she had placed there just for this purpose. She wiped between her legs, mopping up Buddy’s fluids before they could stain her dress.

Now would come the post-coital remorse.

“I’d really like to stay for a while and go again but if I’m not home by nine Cindy will have a fit,” Buddy lied as he made his way to the bathroom.

He looked a little pathetic as he hobbled away naked with his saggy ass clad in his tighty-whities and his argyle socks pulled up high on his bony calves. Jordan waited while Buddy washed his face and checked himself in the mirror to make sure there was no tell-tale lipstick on his mouth. He gave his undercarriage a quick clean at the sink using a facecloth, carelessly splashing water on the tiled floor.

Jordan poured herself another scotch and checked her phone, waiting patiently for Buddy to dress and check his appearance in the mirror. He took out his wallet and counted out the agreed stipend using crisp banknotes taken from the ATM in the foyer from an account that he kept secret from Cindy.

Jordan dealt only in cash, not because she didn’t trust her clients but because checks and bank transfers left a trail. It was safer for both herself and her clients if there was no record of the transaction.

She saw Buddy to the door, handing him his briefcase and air-kissing him before he left and then stuffing the money in the room safe. She knew that Buddy would stop at the hotel bar and have a drink or two and smoke a cigarette, both as an excuse he could use to tell Cindy if anyone told her that they had seen Buddy at the Ambassador and also to disguise any lingering scent of Jordan’s fragrance.

Her next client would be here soon so Jordan got busy. She peeled off her dress and hung it in the wardrobe and kicked off her heels and went into the bathroom where she cleaned up the mess Buddy had left at the sink and on the floor. Then she took a fresh washcloth and cleaned her privates. She fixed her makeup and brushed her hair and went back into the main room to prepare for Jamar, her next client.

She carefully removed her stockings and slipped out of her garter belt and panties. As she began to dress for Jamar, Jordan thought briefly about how she had entered the world of prostitution.

Her spouse Logan worked as an air traffic controller which paid well enough and Jordan worked as a law clerk and was adequately recompensed. Their combined income allowed them to live comfortably but they both wanted a lifestyle that neither of them could afford: nice cars, overseas travel, fine dining, a swimming pool; all the toys that a couple in their prime could enjoy. They talked extensively about how to supplement their income and money had become an obsession that was affecting their marriage.

One evening they were watching a miniseries called Secret Diary of a Call Girl when Logan joked that one or both of them should undertake sex work to supplement their income.

They both agreed that their sex life was jaded after ten years of marriage and were looking for ways to spice things up. They had been considering swinging or opening their marriage when Logan had made the quip.

“You wouldn’t get jealous if I was to have sex with other people?” Jordan had asked.

“Not if I was doing the same. We would need to set some ground rules though,” Logan replied.

And that was how the conversation that would change their marriage had started.

Jordan came out of her reverie. She unwrapped a pair of Wolford fifteen-denier caramel pantyhose. They were sheer to the waist and delicate so Jordan took great care putting them on. She smoothed out any wrinkles and ensured that the seam of the panty sat in her buttock crease at the rear and along her pubis at the front. She shimmied into a pair of translucent white nylon full-cut panties and admired herself in the mirror. Then she slipped into a simple black satin slip and sprayed herself liberally with Poison perfume.

Jamar was in his mid-thirties and an incredibly handsome African-American who was a prominent businessman and was married to an incredibly attractive African-American woman. Jordan had seen pictures of them together in the social pages.

Jamar also had a raging pantyhose fetish that his wife did not satisfy. He blamed Sex in the City and millennial celebrity women for speaking out openly against pantyhose and calling them a fashion faux pas. His wife absolutely refused to wear nylons, except in the dead of winter when she wore thick opaque tights with boots which Jamar despised. His pleas for her to wear sheer hosiery fell on deaf ears and when he told her he thought they were sexy and he would like her to wear them to bed she had accused him of being some kind of pervert.

Jamar had found Jordan’s profile in the personals under the heading Adult Services on an online dating site and after some trepidation had approached her, looking for someone who would pander to and genuinely appreciate his fetish. After some back and forth to ensure that Jordan was genuine and consummately discreet they had hooked up in this very hotel and Jamal went away completely satisfied and happy that he had found a unique woman who had enjoyed his company as much as he had enjoyed hers.

This was to be their third meeting and Jordan was confident that she would be able to meet Jamar’s needs. His text pinged in her phone and she waited for him by the door. Jamar used the stairs rather than the elevator even though her room was located several floors above the lobby and Jordan was keenly aware of his need for discretion as she opened the door a crack and as soon as she saw the stairwell door open she flung the door to her room wide open so Jamar could slip inside unseen.

Even though he had jogged up the stairs Jamar looked fresh and unfazed by the exertion and his handsome face beamed a bright smile at Jordan. He appreciated that she was dressed exactly how he wanted her to be.

“Perfect,” he whispered and pulled her into his arms.

He kissed her softly, his hands immediately seeking her legs so he could stroke her gossamer nylons, rubbing the satin slip against the diaphanous hosiery.

Jordan could barely get her arms around his muscled torso as she rubbed against him feeling the bulge in his crotch begin to grow. The kiss became more impassioned. Their lips pressed together harder and their tongues intertwined. Jamar stroked Jordan’s thighs a little harder, moving his fingers to the crease where her legs joined her torso, stroking the fine wrinkles in her nylons before progressing to the rounded orbs of her buttocks. He caressed her ass, rubbing the satin panty material against her pantyhose for his own enjoyment rather than Jordan’s, although she sighed with contentment when he touched her there.

He frogmarched Jordan towards the bed and pushed her down. She lay there in an erotic pose, her feet crossed at the ankles, her long legs clad in the shimmery hose, the hem of her slip high on her thighs so that Jamar could see the crotch of her translucent nylon panties and the dark seam of her pantyhose running along her pubis. She smiled up at him seductively and put a finger in her mouth and pouted. She knew that her provocative pose would ignite Jamar’s passions.

Jamar undressed, hanging his suit and his shirt on the coat hanger that Jordan had left out for him. He fastidiously tucked his socks into his shoes and folded his boxer briefs and laid them on top. While he did this he stared at Jordan and she saw the lust on his face become more intense, signalled by his ever growing erection. She scooted to the edge of the bed, never taking her eyes off him.

His cock was huge. The shaft was dark mahogany with thick blue veins running along the velvety flesh, the head was purple and glistened in the lamplight. Jordan swallowed as Jamar approached the bed wondering how she was ever able to take that massive organ inside her but she had done so twice before and she would do so again.

Jamar stood beside the bed, his cock inches from her face, an offering she was meant to imbibe. He pushed his phallus towards her mouth as he glided her slip up her narrow back slightly so he could take in the vista of her pert bottom clad in the flimsy white panties and glossy hose, the seam running perfectly straight down the crack of her ass just the way he liked it.

A translucent pearl of pre-ejaculate had formed at the eye of Jamar’s penis and Jordan flicked out her tongue and licked the salty-sweet dewdrop and swallowed it and opened her mouth wide as she did her best to assimilate his organ. She could accommodate the glans and about a third of the shaft of the mighty appendage in her mouth, her red lipsticked lips stretched wide, her tongue slavering the slick spongy head.

Jamar was caressing her bottom, his finger tracing the dark seam of her pantyhose through the transparent panties. Jordan felt herself becoming aroused but her job was to please her customers, not herself. She sucked on Jamar’s cock as best she could and he stared at her intently as she made a valiant effort to suckle his bloated phallus. Her pretty face was screwed up a little in consternation as she worked her lips up and down the shaft of his cock, her glacial eyes sparkling, enhanced by the black kohl and mascara and gaudy pink and purple eyeshadow, the nostrils of her cute nose flared as she struggled to breathe, her mouth was distended, her red lips stretched around the circumference of his mighty organ.

But he could see the pleasure in her eyes too and feel her shiver with delight as he massaged her buttocks. He didn’t touch her pubis but Jordan was sufficiently aroused that the crotch of her panties was moist. She stared up at him and fluttered her eyelashes and Jamar sighed as he felt her mouth working on his cock, his hands exploring her buxom bottom sheathed in the diaphanous pantyhose. This was his fantasy.

It wasn’t so much that Jordan was white. He had beautiful white women furtively solicit him every day. The secretaries and PAs in the office, businesswomen at meetings and conferences, mothers at the daycare centre when he picked up his son; even his colleague’s wives flirted with him. He was a very tall handsome black man with a fit muscled body. He was intelligent, polite and articulate; a good conversationalist who engaged with women as equals and they coveted him. But other than his weekly interludes with Jordan he never strayed.

If only his wife Cynthia would pander to his pantyhose fetish and occasionally suck his dick he wouldn’t need Jordan’s services. Jamar justified his infidelity because having sex with Jordan wasn’t really cheating as far as he was concerned. Jordan was exotically different to the other women in his life and she was a prostitute. All he was doing was exchanging cash for services; there was no emotional or personal connection.

Jordan reached out and raked her red-painted fingernails along Jamar’s substantial scrotal sac then she cupped his testes and caressed them while her tongue tickled his fraenulum and her lips caressed his shaft and all thoughts of Cynthia vanished. Jamar returned to the present and slid his hand inside Jordan’s panties so he could touch those stupendous globes enveloped by her gossamer hose.

He ripped his cock from her mouth with a resounding plop and leapt on the bed. Jordan took a deep breath and rolled onto her belly anticipating Jamal’s next manoeuvre. He lay down on top of her pressing her into the bed with his muscled weight as his cock slipped inside her panties and nestled in the crevice between her buttocks, his legs on top of her legs.

She awkwardly turned her face sideways so that Jamal could kiss her while he humped her pantyhose-sheathed ass and thighs, his cock felt like a hot iron bar as it pressed against her delicate flesh. Jamar liked to feel every scintilla of Jordan’s body on his skin. The silky, slinky satin slip on his abdomen, the sleek sensuousness of her nylon panties on his lower belly and of course the tantalising diaphanous sleekness of her pantyhose on his cock, crotch and legs.

 
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