Strange Bedfellows Ch. 02

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Trans detective and tranny whore chase down sex traffickers.
13.6k words
4.86
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Part 2 of the 3 part series

Updated 06/11/2023
Created 01/08/2022
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MicheleNylons
MicheleNylons
3,969 Followers

Chapter Two -- The Wolf and The Bear

In the car on the way back to her leased penthouse suite Dmitriy texted Jennifer and told her he wanted sex.

Jennifer smiled to herself. It was a good sign that Dmitriy wanted her to participate even if only over video telephony. She went to the bedroom and douched and changed into lingerie, stockings and heels and freshened her makeup. Jennifer had a dildo manufactured that exactly matched the length, girth and shape of Dmitriy's erect penis. He had modelled for it personally and it was accurate right down to every vein and the tiny Tyson glands on the underside of his glans. She put it on the bed with a tube of lubricant ready for use.

Jennifer was far from stupid but none of her predecessors had been stupid either, including Katya Kuznetsova. But some of them had thought that they could hold onto Dmitriy by trying to encourage him to be monogamous. Jennifer knew from the start that strategy would never work; this was a man who liked to deflower virgins for fuck sake!

Jennifer was unique amongst all of Dmitriy's Girl Fridays in that she not only helped run his business empire; she was also his most trusted field operative. On his behalf she had seduced business impresarios, politicians and senior law enforcement officials to obtain sensitive information or to blackmail them. She had smuggled blood diamonds out of Africa inside her rectum. She had assassinated Dmitriy's opponents and any other targets that he told her to. All of this without ever questioning the morality of it.

This put Jennifer in a unique but dangerous position.

Before Jennifer there had been a string of other beautiful intelligent women who had been Dmitriy's personal assistants including Katya Kuznetsova and the girl Jennifer had replaced, Tiffany Crouch.

Dmitriy preferred to have a woman as his personal assistant and consigliere. A woman was less likely to try to overthrow him. Not that he didn't trust his many lieutenants, but he kept them distant. His PA was dependent on him for her life and she was treated with loving respect and knew his darkest secrets. But he eventually tired of them, some sooner than others. All of his former Girl Fridays were kept under surveillance because they knew so many of his secrets and he'd killed two of his previous PAs who for various reasons had lost his trust.

The others had retired to live a life of luxury and two of them ran high-class bordellos run by his organisation. On retirement Katya had worked for Dmitriy through Vlad Volkov, a sex trafficker, finding girls to fill the ever-increasing demand for fresh-faced pretty young women. Until Katya teamed up with a Bratok named Uri Orlov and assisted in an FBI operation to insert an undercover operative close to Dmitriy with a view to bringing him to justice as part of a witness protection guarantee for Uri.

Jennifer had been that operative and Uri and the FBI Special Agent in Charge, Donald Chase, had been assassinated and Katya sold into sex slavery as a life-long punishment. Jennifer had been sold out by a corrupt senior FBI official named Mike Cole who had wiped all official records of her existence and she had no choice but to turn to Dmitriy and the dark side. And she loved it.

Jennifer knew that when her time was up as Dmitriy's Girl Friday it would be easier for him to kill her and ensure his secrets went with her to the grave rather than to allow her to live and work for him as a brigadier, supervising his lieutenants which was what he had proposed. She also knew that the longer she remained his Girl Friday, the longer her life was guaranteed and the longer she had to arrange for her retirement and with that in mind she made it her business to hand-pick the women that Dmitriy slept with.

The first time had been opportunistic. Dmitriy usually flew in private jets but the first time Jennifer had travelled with Dmitriy overseas they had flown First Class direct from LA to Sydney Australia on a Qantas flight and when the cabin lights dimmed and most passengers were asleep Jennifer and Dmitriy had made love in his first class cocoon. When the flight attendant discovered them, rather than instructing them to stop she had taken her break and joined them; slipping out of her skirt but leaving on the rest of her uniform which Dmitriy found very kinky.

Jennifer had enjoyed the experience and had arranged with Vlad Volkov to provide her with pretty virgins for Dmitriy to deflower and she joined in enthusiastically. The frightened young girls were often comforted by having a pretty young woman in bed with them while Dmitriy seduced them. Most had been compliant but one or two had had to be restrained. It turned Jennifer on immensely to hold down the young girl while Dmitriy fucked her until she became compliant and a willing recipient of Dmitriy's huge cock. Sometimes Dmitriy held down the virgin while Jennifer deflowered her.

Jennifer also arranged for select young women to keep Dmitriy entertained while she was away but never the same girl twice. She also made it a practice to have select young women join them in bed. Dmitriy liked to fuck young women and have Jennifer watch or participate. He also liked to watch Jennifer fuck pretty young women and Jennifer liked to do it. Dmitriy would take Jennifer from behind while Jennifer fucked the pretty young prostitute missionary. She liked it when he timed his orgasm to come in her ass just as she was coming inside the girl.

Dmitriy had a voracious sexual appetite and unlike the Girl Friday's before her who had tried to restrict it, Jennifer encouraged it but she made sure that she remained his staple diet.

Jennifer sprayed herself with Dior Poison perfume, the only scent that Dmitriy let her wear. She didn't need to of course, but the aroma of the perfume would add to the excitement and realism. She brought her laptop onto the bed and opened up a secure video conference channel with Dmitriy who was lying naked on their huge Venetian traditional Italian-style wooden four-poster bed with silk sheets and satin comforter. Beside him lay a pretty young blonde girl barely eighteen years of age. She was wearing only fully-fashioned stockings attached to a red satin and lace suspender belt, diaphanous red hipster panties and high heels.

Jennifer was well aware of Dmitriy's nylons fetish and had selected the lingerie, hosiery and shoes herself for the young woman to wear. Jennifer was wearing exactly the same lingerie, nylons and heels and her makeup was identical to the eighteen-year-old's: heavy eyeshadow, mascara and eyeliner and bright red whore-lipstick.

"Hello my love. Shall we begin? I know you've had a long day and you must be tired," Dmitriy smiled into the camera which was set up at the foot of the bed and lazily stroked the young woman's small breast.

"Take your time my love. You know I live to serve you," Jennifer snaked a red-painted fingernail down her left leg, stroking her flesh through the silky stocking and tapping the scorpion tattoo above her ankle.

Jennifer mimicked Dmitriy's actions and lazily stroked her own breast, causing her nipple to engorge. Dmitriy took the young girl's hand and directed it to his groin and she dutifully took his semi-erect phallus in her fingers and softly stroked it and Dmitriy lowered his face to the girl and kissed her.

Jennifer wished she could feel Dmitriy's lips on hers but she made do by putting her fingers in her panties and began to finger her cock. She became fully tumescent and so did Dmitriy. Jennifer stroked her breasts and her cock and was pleased to see Dmitriy looking at the screen now and then to watch Jennifer while he played with the young girl.

Jennifer didn't know the girl's name, nor did she want to. As far as Jennifer was concerned she was just a surrogate for her in her absence.

Dmitriy spent some time kissing the girl and playing with her breasts while she stroked him to full tumescence. Then his hand wandered down her flat belly and inside her panties. Jennifer mirrored his actions and slipped her other hand inside her panties. The girl gasped when Dmitriy opened her labia and stroked her clitoris. Jennifer fingered her puckered bud, watching the screen intently.

Jennifer could sense Dmitriy's impatience. He wanted relief. When he was in this mood Jennifer knew to satiate him quickly so that he could then take his time and make love to her again slowly. The girl had been instructed accordingly by Jennifer and when Dmitriy pressed on her head she willingly lowered her face down to his lap and began to suckle his huge member.

Jennifer took the silicon replica-cock and sucked on it while she fingered her sphincter, lightly circling her fingertips around the puckered pink ring. The cock in her mouth felt exactly like Dmitriy's but of course she couldn't taste the pre-seminal fluid oozing from the eye like the girl on the screen could. The girl was suckling Dmitriy's penis, as much as she could fit in her mouth anyway, while Dmitriy worked on her cunt. Her nipples were erect and girl was moaning sluttishly around the mouthful of cock.

Jennifer sensed what was coming next and reached for the gel-lubricant and smeared a good dollop on her sphincter. When Dmitriy drove two fingers into the girls cunt Jennifer pushed two fingers inside herself. She sucked harder on the prophetic penis as she worked her fingers deeper into her anus. Her penis stood proud above the waistband of her panties, a rope of clear precum dribbling from her glans.

Dmitriy turned to the camera and smiled. He nodded at Jennifer and she nodded back.

Dmitriy flung the girl onto her back and opened her legs wide. Jennifer emulated his actions and lay on her back with her legs wide. She stuffed a pillow under the small of her back.

Dmitriy snaked his throbbing organ inside the girl's panties and positioned it inside the folds of her labia and Jennifer covered the silicon phallus with lubricant, pushed it inside her panties and pressed the glans against her sphincter.

As Dmitriy slowly impaled the young girl on his monstrous phallus Jennifer slowly pushed the lifelike replica cock inside her tight anus. The dildo stretched her sphincter causing little rings of pleasure to radiate from the tight muscle. Dmitriy watched Jennifer on the screen intently as he slowly impaled the girl on his massive cock.

Jennifer pushed the prosthetic cock all the way inside her anus, biting her lip at the pleasure and pain as the monstrous cock dilated her tight asshole. Dmitriy smiled at her, almost wickedly, then slowly began to fuck the beautiful young creature lying beneath him. He grabbed her stocking-sheathed legs and made her wrap them around his flanks to increase his pleasure as he fucked her at a leisurely pace.

Jennifer could hear the girl, gasping and grunting, sighing and crying with pleasure as Dmitriy fucked her. Jennifer reached for her cock and began to stroke it as Dmitriy fucked the young blonde prostitute. She thrust the dildo in and out of her tight anus, pressing the glans on her prostate to maximise her pleasure as she firmly gripped her cock and stroked it. She imagined that Dmitriy was lying on top of her, ploughing her with his huge cock, whispering endearments, smiling down at her, kissing her softly as he fucked her.

Dmitriy was doing exactly that to the young girl on the screen, regularly craning his neck to watch Jennifer. He made kissing gestures to her and smiled; the lust on his face evident. He fucked the girl harder and Jennifer worked the dildo faster and harder inside her anus and stroked her cock a little faster too. She was close to extremis. The pleasure radiating from deep in her bowels was matched by the tingling delight coming from her throbbing penis.

She saw Dmitriy grab the girl by the thighs and drive his cock all the way inside her. The muscles on his back rippled and his whole body quaked as he roared with pleasure and spent his load deep inside the young girl who cried out at as her own orgasm shook her. She writhed beneath Dmitriy's tattooed muscled body, scissoring her nylon-sheathed limbs against his body, raking her high heels on his abdomen, screaming obscenities as she climaxed.

Jennifer pressed the button on the bottom of the dildo and it suddenly began to vibrate and pulsate. She drove it deep in her ass and pushed it on her prostate as she frantically stroked her engorged member until it ejaculated a geyser of hot semen on her tits and her stomach. She raised herself up off the bed and drove the dildo in and out of her anus at a frenetic pace as her the last of her issue spattered on her belly.

She stared intently at the screen and watched Dmitriy fuck the little girl into a paroxysm of bliss as he spent his load deep in her tight cunt; his head was turned towards the screen smiling at Jennifer.

Jennifer felt a pang of jealousy but it passed fleetingly and then she was suddenly sated and very tired, nearly exhausted.

Dmitriy waved her goodbye, his cock still buried in the pretty blonde. He hadn't finished with the girl yet by a long shot but he knew that Jennifer was tired and he allowed Jennifer to break the connection as she carefully switched off the vibrating dildo and extracted it from her ass.

Jennifer knew that she should undress, shower and change into night attire but she was just too tired. She put the laptop on the nightstand, tossed the dildo aside, kicked off her heels, pulled up the covers and immediately fell asleep. She would tip the maid extra for having to deal with the soggy semen-stained sheets in the morning.

She had a busy day ahead of her: a friend to betray and a goat to tether.

*****

Katya Kuznetsova -- One Year Earlier

Katya Kuznetsova had been Dmitriy Tanas Yakovich's personal assistant and Girl Friday until she was usurped by a pretty young virgin named Priscilla Montgomery. Katya knew that the day would come when she would be replaced, just like she had replaced Liza Lawton. For three years she had effectively been Dmitriy's sex slave, working for a man who sold people, drugs and stolen property and committed crimes such as kidnap for ransom and murder at a whim and headed up his own arm of the Russian Mafia whilst distancing himself from the dirty work. It had hardened Katya.

When she was replaced, Katya moved east and set herself up in a well-appointed cottage in Southold on Long Island, hiding amongst the moneyed elite. She tried marriage for a while but it didn't stick so she established a business scouting young virgins to pass onto Vlad Volkov who would arrange to have them abducted and sold into sexual slavery. She became immune to the everyday barbarity of it and knew that she herself was only a heartbeat away from meeting a similar fate to the abducted sex-slaves or the possibility of being killed by Dmitriy because she knew too much about him.

Katya had been in the safe house just outside Cockeysville when Uri's car exploded the day after she had handed Jennifer Jones over to Vlad Volkov. Their FBI handler Donald Chase's car had been involved in fatal collision on the I-95 that afternoon and they knew it was no coincidence. Uri's car was packed with their belongings and they were trying to escape Dmitriy's clutches.

Vlad Volkov had burst into the safe house with three other henchmen and put a gun to Katya's head and had taken her to Dmitriy Yakovich who had viciously fucked her at gunpoint over his office desk laughing as she cried tears of sorrow for Uri. He had then handed her Vlad Volkov with instructions that she was not to be killed.

Vlad could do with her as he pleased but she was to live a life of constant sorrow and regret, knowing that her betrayal of Dmitriy Yakovich was the reason for her wretchedness.

Vlad and Katya had worked closely for years, she supplying him with victims for the sex trafficking trade but she had always been haughty and aloof, secure in the knowledge that she was protected by Dmitriy Tanas Yakovich.

"As the Americans say: out of the frying pan, into the fire but I prefer the Russian version: I ran from the wolf but ran into a bear," Vlad chuckled as he drove Katya back to her house in Southold.

"Dmitriy has arranged for the deeds to your fancy house to be signed over to me. I think that I will live in it instead of selling it. You will work in my brothels in New York and New Jersey, not that far away, but I will have you brought to your old house now and then so you can see what you have lost," Vlad grinned wolfishly.

Katya snaked her hand across his thigh and stroked it lazily.

"What if I give you willingly what you are going to have to take? I have a considerable amount of cash and jewels in a safe deposit box and investments in an overseas company," Katya found Vlad's cock erect, lying along his thigh, held there by his tight jeans.

"Dmitriy knows about your safe deposit box in the Chase Bank in New York and it is being cleared as we speak. Your shares in Rio Tinto have already been transferred to one of Dmitriy's holding companies. You have nothing Katya," Vlad chuckled coldly.

Katya snatched her hand away from his thigh. Her position was helpless. She had nothing left to bargain with.

The two-car convoy arrived at Katya's estate at Southold and Vlad led Katya into her house while his henchmen secured the perimeter to make sure they weren't disturbed. She willingly opened the safe in her office knowing that resistance was futile. Vlad cleaned out the cash and jewellery and led Katya upstairs, walking behind her so he could admire her firm ass and long legs sheathed in glistening sheer nylons.

He made no pretext of his intent and threw her on the bed and fell on her.

Katya did not resist as Vlad straddled her prone body and stripped himself naked while he gazed down at her long lithe body dressed in the tight black silk dress.

He stared at her pale blue eyes accentuated by her dark eye makeup and seductive lips painted with blood-red lipstick. He had longed to kiss those full sensuous lips, to lie on top of her alabaster flesh, longed to feel those silken-shrouded limbs on his sensitive flesh as he entered her.

Vlad tore at her dress and Katya didn't resist him. She lay prone with her limbs spread, her long legs clad in flesh-toned hold-up stockings, her shaved mound shrouded in translucent white panties, her small breasts cupped by a matching brassiere, her erect red-berry nipples visible through the sheer fabric.

He eased aside her panties and thrust himself into her tight tunnel, still moist with Dmitriy's semen, and she wrapped her legs around him and snaked her tongue into his mouth as he kissed her.

Vlad Volkov revolted her more than any man in the world but right now he owned her and he could do anything he wanted with her. He was going to fuck her regardless so she might as well be compliant. Dmitriy had often used Katya to seduce men that she loathed but she had done it willingly because he was her master. This was no different as far as Katya was concerned. She had nothing left except her body and one single secret that she would never tell no matter what.

Vlad rutted against Katya, thrusting deep into her tight cunt, staring into her ice-blue eyes looking for signs of fear and loathing but her eyes were empty. She met his trusts and he could feel her becoming wetter, she ground her pubis against his so that her clitoris was stimulated. She wrapped her legs around his torso and he stroked them and ran his nails down them, laddering the sheer nylons.

He kissed her viciously, biting her lip, thrusting his tongue into her mouth, tasting the blood. The blood matched her lipstick and Vlad watched her lap it away with her tongue. He wanted to defile her, this woman who had always made him feel inferior, but even now in her ripped dress, her tattered nylons and bleeding mouth she stared up defiantly at him and the harder her fucked the harder she fucked him back.

MicheleNylons
MicheleNylons
3,969 Followers