Chapter Two – Buyer Will Want to See Dick
Uri Orlov drove very well for a man whom Jennifer estimated had drunk the best part of a bottle of Stolichnaya vodka. He could probably have driven better if he kept his eyes on the road rather than on Jennifer’s tits and legs. She tugged on her skater skirt but it kept riding up exposing most of her legs clad in the mauve opaque tights.
“No need to be shy. We will see plenty of each other over coming days,” Uri grinned and blew smoke out of the window.
They stayed on the I-95 heading north into Maryland, bypassing Baltimore and Towson on the I-695 until they came to Cockeysville off the I-83. Uri then took a series of secondary roads completely losing Jennifer. She was sure that he doubled back on some of the tree-lined lanes and he seemed to spend a lot of time looking in the rear-view mirror.
Uri turned his black SUV down a dirt road and came out of a grove of thick trees and pulled up next to an old colonial style house that looked like it could do with some renovations. It was what real estate agents called a ‘fixer-upper’. Jennifer saw a curtain twitch but the only sound she could hear was birdlife and somewhere in the distance a babbling stream or brook.
“Get suitcase. Come inside,” Uri puffed as he eased his large body of the car.
Jennifer buttoned her red wool coat and opened the back door of the car. She lugged her suitcase after Uri, the wheels useless on the gravel path. The door opened as they approached and Jennifer peered into the hallway of a two story cottage.
“Take your suitcase upstairs to the bedroom,” a woman’s voice with a Slavic accent called from inside the house.
Jennifer, with no assistance from Uri, lugged her suitcase up the wooden staircase and stopped on the top landing to survey her surroundings. The inside of the house had been renovated and she wondered if the exterior had been purposely left weathered and unchanged as a means of disguise. This was the obviously the safe house that Chase had referred to and she knew that Uri was in WITSEC. She presumed the female voice that she heard below came from Katya.
There were three bedrooms and one bathroom upstairs, the master had a half bath and it was obviously occupied by Uri because it stank of cigarette smoke. The second bedroom must be Katya’s. It was neatly kept with makeup, perfumes and lotions arranged neatly on a walnut vanity. A pair of vintage nylon stockings hung drying over the brass bedhead. A red satin evening gown was fitted to a tailor’s dressform; the garment looked to be nearly finished. A sewing kit was opened on the polished oak floorboards beside it.
The third bedroom was hers Jennifer supposed. It was small and neat with a double bed fitted with fresh bedding. It looked like it had been recently cleaned and aired. There was a red velvet chaise lounge arranged along one wall that seemed a little opulent compared to the rest of the surroundings. The bars on the windows were a little perturbing: were they designed to keep someone out or someone in?
“You can unpack later, come over to the window so I can get a good look at you,” Katya had crept up on Jennifer and made her jump.
How could she not near hear a woman wearing four-inch high heels walking on polished oak floors?
Katya Kuznetsova was a little over six feet tall in heels. A stunning slim woman with jet black hair cut into a severe bob which accentuated her deep blue expressive eyes. She had pert breasts and long legs clad in gossamer-sheer nylons and had a tattoo of a scorpion just above her left ankle. She made the simple black shift she was wearing look like high fashion. Her face was narrow, with accentuated cheekbones, a pointed chin and small nose. Her skin was pale and she wore heavy eye makeup and blood-red lipstick. If Uri Orlov was a caricature of Boris Badenov, then Katya was his Natasha Fatale, but with slightly better English.
Katya half-dragged Jennifer over to the window where the light was better and studied her. She lifted Jennifer’s chin, meticulously examined her face and opened her mouth to inspect her teeth.
“Not bad. I’ll need to fix your hair and makeup. Take off that skirt,” Katya ordered.
“What the fuck!” Jennifer was getting angry.
This woman, who hadn't even introduced herself, was treating Jennifer like a slab of beef, poking, prodding and scrutinising her.
“Don’t be bashful, take off your skirt,” Katya began to tug at Jennifer’s skirt and Jennifer slapped her hand away.
She unzipped her skirt and stepped out of it.
“Take off your top too,” Katya reached for Jennifer again and Jennifer stepped back out of the way but she pulled the body-shaper over her head.
“Stand still. Stop behaving like a brat,” Katya pulled Jennifer back into the light and inspected her body.
She lifted Jennifer’s small but shapely breasts and inspected the almost invisible silvery scars following the natural curve underneath her breasts.
“Your surgeon did a good job. Good size too… not too big. American women always want big hooker tits,” Katya said disdainfully.
“Don’t wear those shitty opaque tights again and take off those shitty shoes,” Katya tugged at the waistband of Jennifer’s tights and again she slapped Katya’s hand away.
“It’s good to put up fight a little. Customer will want that but don’t fight me; I am here to set you straight. What I teach you over next few days will save your skinny-ass life,” Katya let Jennifer take off her own shoes and roll down her tights.
Jennifer thought it was hypocritical that Katya called her skinny.
Katya studied Jennifer’s body critically and made her turn around. She cupped Jennifer’s buttocks and prodded and poked here and there.
“Nice ass cheeks and not synthetic, good figure, little bit of work done here and there but understandable, good legs, nice feet, fresh pretty face… you will do. Untuck please,” Katya said almost indifferently.
This time Jennifer gave Katya's hand a good wallop when she reached for her genitals. Jennifer didn’t tuck all the time because it was laborious but it was something she had learned to live with. She had developed a technique for everyday using surgical tape that didn’t cause discomfort and more importantly allowed her to pee without untucking.
Jennifer untucked and her penis swung free and her testes dropped out of her inguinal canals and filled her scrotum. She was freshly shaved down there. She flinched a little but managed to stand still while Katya hefted her genitalia in her hand.
“It’s a good size but not too big; you don’t want man to feel inferior,” Katya chuckled.
“Functionality ok? Not fucked up by hormones?” Katya gently squeezed Jennifer’s penis.
“It works fine!” Jennifer said indignantly.
“Ok, don’t get your panties in a bunch. Put on that robe and let me see what you brought with you. Just empty your suitcase on the bed,” Katya waved her hand at Jennifer’s suitcase.
Jennifer took down a white silk robe hanging off a coat hook fitted to the oak-panelled wall and put it on. While she was doing so Katya walked over to the door and held a whispered conversation with Uri who Jennifer didn’t even know was there. Had he been watching Jennifer undress? How did these two people get around so quietly?
Jennifer tipped out the contents of her suitcase on the bed as instructed and took a pair of panties, ripped off the price tag and stepped into them.
“You getting a good look?” she called indignantly to Uri who was watching her over Katya’s shoulder.
Uri stormed into the room and pushed Jennifer onto the bed where she fell with her arms and legs akimbo.
“You think you the first tranny-girl I’ve seen? Get over yourself! What we are doing here is important and for you means difference between life and death. Ok to fight a little when man come for you but don’t be insolent,” Uri loomed over Jennifer, his face red and menacing.
“Ok Uri, point made. Now leave us women to do women stuff. You brought me a good candidate. I’ll contact Vlad and tell him that the pictures will be up this afternoon,” Katya pulled Uri off Jennifer and he let her lead him to the door.
She closed it behind him and came back to the bed and helped Jennifer sit up and then sat down beside her and put her arm around Jennifer’s shoulders.
“Uri is under a lot of pressure; you understand?” Katya said by way of apology.
Jennifer just nodded.
“Good, now let’s see what you have here,” Katya actually smiled.
“Oh, Katya Kuznetsova by the way. Pleased to meet you,” Katya gave Jennifer a little hug and kissed her cheek which surprised her.
They arranged the clothing that Jennifer had purchased on the bed. Some items Katya dismissively threw into the corner of the room but most of the clothing they kept.
“No time to waste. Come with me and I’ll fix your hair,” Katya took Jennifer by the hand and led her to the bathroom.
She sat Jennifer down on a stool and began to arrange hair styling accoutrements on a towel next to the sink.
“What are we doing?” Jennifer asked.
“You saw the ad on website. The man wants a girl twenty or younger. Make you look younger,” Katya said by way of explanation.
Katya was all business. She made Jennifer put her head over the sink and washed her hair and towelled it dry then she went to work with hair-cutting shears and Jennifer felt some trepidation as her locks fell to the floor.
“Don’t worry you will look beautiful,” Katya said and kept snipping away.
Jennifer endured what seemed like an eternity of having her hair cut, dyed, crimped, and styled. Halfway through the process she was surprised when Uri arrived with cups of Russian coffee and they took a break to drink it.
The drink made with espresso coffee, cream, sugar and a shot of vodka was delicious and Uri offered his Marlboro’s but Katya refused and lit one of her own Marlboro Menthol’s and handed it to Jennifer and then lit one for herself.
“Ok. Fuck off and do whatever it is you do. We’re busy,” Katya stubbed out her cigarette and ushered Uri out of the bathroom.
After Katya had applied the finishing touches and blow-dried Jennifer's hair she led Jennifer to her bedroom, refusing to show Jennifer the results of her salon work until she had done her makeup.
Katya spent half an hour fussing with Jennifer’s makeup until she was happy with the results.
“Now you can see,” Katya spun Jennifer around on the swivel chair so that she faced the mirror.
Katya had cut Jennifer’s hair into a pixie-cut with swept bangs and coloured it a deep red with darker and lighter red highlights. She’d matched Jennifer’s pale skin tone with foundation and finishing powder, given her winged eyeliner, she’d used deep plum, vibrant copper and a shade of peach eyeshadow and finished with bright red lipstick.
She had painted Jennifer’s nails to match the shade of her lipstick.
Jennifer hardly recognised herself. Her face was transformed. She looked younger, prettier and very feminine.
“That’s amazing!” Jennifer admired herself in the mirror.
“I will teach you how to do your makeup like this and style your hair. The man will want you looking pretty at all times,” Katya said in her Slavic accent and Jennifer was abruptly reminded of why she was here.
“Come. We will take photos,” Katya pulled Jennifer out of the chair and ushered her down to her bedroom.
Uri had arranged lighting and set up a camera on a tripod in front of the chaise lounge.
“This first,” Katya pointed to a black basque lying on the chaise lounge which was not part of the collection that Jennifer had brought with her.
“Get yourself tucked and put on these panties,” Katya snatched up a pair of black nylon panties with red lace trim off the bed.
Katya disappeared while Jennifer stepped into the panties and put on the basque. The suspender straps flapped around her thighs and she looked to see if she could unhook them from the garment.
“No!” Katya screeched at her as she stormed into the room.
“Put these on,” Katya held out a pair of stockings and Jennifer wondered if they were the ones she had seen drying on Katya’s bedhead.
“Fucking American women with their fucking bare legs! They think they are liberated because they refuse to wear nylons! Wouldn’t dream of stepping out of the house without wearing makeup on their face or styling their hair but happy to show off their pale scabby legs, or fake-tanned limbs that look fucking awful. Fucking housewives of wherever!” Katya ranted.
“Real women wear stockings or pantyhose. Not shitty K-Mart hoses but quality, sexy nylons,” Katya settled down a little while Jennifer sat on the lounge to put on the stockings.
She didn’t understand Katya’s rage about hosiery, Jennifer herself was a fan of wearing nylons to enhance her legs but Katya seemed fanatical.
The stockings felt delightful, silky-sheer and decadent as she pulled them up her legs and smoothed out the wrinkles. Being fully fashioned they were cut to the shape of her leg and had a backseam which she had a little difficulty getting straight. Katya came over to help, making Jennifer stand while she straightened her seams and garters and evened out the dark smoky welts at the top of her thighs so that they matched.
“Here. Put these on,” Katya held out a jewellery case which contained a silver necklace, drop earrings and a bracelet all set with emerald stones.
“Swarovski crystals. Not expensive but not cheap either,” Katya explained.
She helped Jennifer fit the necklace and her sweet breath on Jennifer’s neck was quite pleasant. Katya’s perfume was something exotic and eighties, possibly Poison.
“Put on the fuck-me heels. You shouldn’t really wear open-toe sandals with stockings but we want to show off the Cuban heels and reinforced toes in the pictures.”
She helped Jennifer buckle the high-heeled sandals and because she was kneeling down Jennifer could see up Katya’s skirt. She was wearing hold-up stockings but it was too dark to see her panties. Katya saw her looking and smiled and Jennifer snapped her eyes away.
“Ok, go pose on lounge. Look sexy,” Katya waved at her.
They spent the next two hours taking photographs of Jennifer dressed in lingerie, an evening gown, daywear, even wearing schoolgirl and Girl Scout uniforms. Jennifer didn’t complain or ask where the costumes had come from. Katya fussed around her making sure Jennifer posed perfectly, touching up her makeup and brushing her hair as needed.
Jennifer was instructed not to smile. She was told to pout or look disinterested or peeved: to act like she didn’t like wearing the clothes or posing for the pictures.
“Ok good. Now we take a couple of dick picks,” Katya said matter-of-factly.
“What?” Jennifer thought she had misheard Katya.
“You are a tranny-girl that I want to trade for money. Buyer will want to see dick,” Katya said clinically.
“Get back into the basque and stockings and lie down on lounge,” Katya waved at the basque and balled up stockings on the bed where they had been thrown after the shoot.
“Why couldn’t we just take the pictures when I was dressed in the basque the first time?” Jennifer said a little sulkily.
It had been a long day already and she was tired.
Jennifer untucked again and put on the basque, stockings and fuck-me heels. Katya had her put on the black panties with the red lace trim and took some shots with Jennifer showing off the bulge in her panties and then she had Jennifer pull her cock out of the leg-hole of her panties and took some more and finally she took a couple with Jennifer without the panties.
“Ok, I need a few with you erect. The buyer want to know that it is fully functional,” Katya pointed to Jennifer’s flaccid penis.
Jennifer was no prude but she blushed.
“I’m not sure I can do that right now; I’m not really in the mood and I’m tired,” Jennifer complained.
“Last couple of pictures, couple of nudes, then we are done,” Katya smiled but she sounded annoyed.
Jennifer played with her penis but it would not respond. Being in this strange bedroom with a woman she had only just met and a brute of a man downstairs and being manhandled and ordered around were not conducive to arousal.
Katya held out a hand and helped Jennifer up off the lounge and Jennifer gave a sigh of relief now that the photography session was finished.
But it wasn’t.
Katya pulled Jennifer in close and pressed her body against her.
“I saw you looking up my dress earlier. You like women as well as men?” Katya’s voice was throaty, sexy.
Katya’s body was warm and in the tight black dress Jennifer could feel every curve and bump of her body.
Jennifer blushed again. Being so tall, Katya towered over her and Jennifer’s face was level with Katya’s breasts where Katya rested Jennifer’s head.
“It’s ok. Were nearly done,” Katya’s hand snaked down and she took Jennifer’s limp penis in her fingers.
Katya lifted Jennifer’s chin, lowered her face and kissed Jennifer full on the lips. Katya tasted like coffee-cream and vodka. Jennifer’s penis began to bloat as Katya slowly stroked it and tenderly kissed Jennifer. Jennifer felt soothed as much as she did aroused and she put her arms around Katya and nuzzled against her.
“Good; it’s working,” Katya whispered and continued to stroke Jennifer to full tumescence.
When the first little droplets of pre-ejaculate leaked from Jennifer’s penis Katya massaged the slithery fluid into Jennifer’s turgid cock. Katya kissed Jennifer tenderly, using only the tip of her tongue, the tips of her fingers flickering along Jennifer’s penis and tender parts.
“Ok. Now we can take pictures,” Katya disengaged from Jennifer and arranged her on the chaise lounge.
She took a series of pictures of Jennifer before her erection began to subside. Jennifer’s lipstick was smudged but it only made her look sexier.
“Ok. Take off the basque,” Katya helped Jennifer to her feet and unfastened the basque.
She carefully rolled up the fully fashioned stockings.
“Here. Put these on,” she handed Jennifer a pair of hold-up stockings still in the package.
Jennifer pulled the package open and slipped into the sheer black stockings, Katya knelt on the floor and helped her put on a pair of red high heels. Jennifer was naked except for the stockings and heels. Katya fussed with Jennifer's makeup a little and then she leaned in and kissed her again, pressing Jennifer into the lounge. Katya lightly caressed her small firm breasts and when Jennifer reached for Katya’s breasts she let her squeeze them through her dress.
Jennifer was becoming tumescent again and Katya broke the kiss and lowered her face into Jennifer’s groin and lapped at her penis. It immediately sprang to full attention and Katya sucked on it a little using her lips and tongue.
“You have a wonderful cock,” Katya whispered and disengaged and went back to the tripod and took a series of posed pictures.
This time Jennifer remained fully erect.
“No sense in wasting perfectly good erection,” Katya said clinically as she reached under her dress and pulled down her panties.
She came over to the lounge and eased Jennifer into a sitting position, her hard cock standing up proudly. Katya placed her legs either side of Jennifer’s and squatted down, putting her arms around Jennifer’s neck for support. Her soft lips found Jennifer’s and her tongue slid into Jennifer’s mouth at the same time as Jennifer’s cock slid into Katya’s warm, wet sheath.
In her high heels Katya was the perfect height to straddle the diminutive trans-woman. Jennifer’s long thick penis slid into Katya’s slick cunt all the way, Jennifer’s pubis pressed on Katya’s clitoris, furthering her arousal. She ground her groin on Jennifer’s and squeezed her cunt tight around Jennifer’s shaft. The feel of their stockings rustling together was delectable and Jennifer stroked Katya’s thighs and then cupped her buttocks.
She lifted Katya up a little so that she could fuck her and Katya took her weight on her heels and rode Jennifer's cock in time with her thrusts.
Not a word was spoken, their lips remained glued together, their tongues entwined. Jennifer felt her orgasm building and she could feel that Katya was becoming wetter and had begun to pant into Jennifer’s mouth as her climax approached. Their stockings rubbed against each other, sending little ripples of pleasure through their legs and into their groins.
Katya slammed her buttocks down into Jennifer's crotch, forcing every inch of Jennifer’s cock deep inside her and ground her clitoris on Jennifer’s pubis. Katya’s heels began to drum on the floor as her orgasm erupted and she hung onto Jennifer, driving her tongue deep into her mouth, sucking the breath out of her. Jennifer held Katya by the hips and pushed upward, driving her cock all the way inside Katya's tight, wet vagina and ejaculated.
The two women held onto each other, grinding against each other, kissing passionately, extracting every scintilla of pleasure from each other.
When they were done Katya put her head on Jennifer’s shoulder and sighed. She clung to her, the bigger of the two women hanging onto the smaller for support. Jennifer kept her cock inside Katya until it began to deflate and plopped out of her.
Katya abruptly stood up and lifted her dress up clear of her crotch.
“Can’t get spunk on my expensive black dress,” Katya said pragmatically.
She picked her panties up off the floor and wiped at her dripping cunt with them then threw them in the corner and dropped her skirts.
“You are a good fuck and you have a good cock,” Katya leaned down and kissed Jennifer quickly on the lips.
“Have a shower. Fix your makeup like I showed you and join us downstairs. We will post the photographs and then have dinner,” she stoked Jennifer’s cheek and left the room.
Jennifer lay back on the lounge, her head spinning.
“What the fuck was that?” she said to the empty room.
Jennifer showered and worked on getting her makeup the same as Katya had shown her. Jennifer prided herself on her makeup skills and she thought she did a pretty good job. Her face looked fresh and the mascara, winged eyeliner and red lipstick looked sexy. She slipped into a pair of sheer-to-the-waist flesh-toned pantyhose using the gusset to tuck, pulled a pair of purple satin panties over them and put on a simple red dress.
Katya had tossed her Mary-Jane’s and anything that didn’t have a heel into the corner so she put on a pair of black high heel pumps. She accessorised with costume jewellery and checked the results in the full-length mirror inside the wardrobe door.
With her diminutive frame and pixie haircut she thought that she looked like a young girl trying to look older.
As she made her way downstairs she could hear Uri and Katya talking loudly to each other in a foreign language she presumed was either Russian or Ukrainian. Uri was in the kitchen banging pots and pans around, the ever present cigarette dangling from his mouth; Katya was sitting at the dining table working on a laptop computer.
“Come and see,” she smiled at Jennifer and called her over.
Jennifer sat next to Katya who had was freshly showered and changed into a crimson satin robe which was partially open revealing a bright red lace camisole. She was wearing sheer tan pantyhose and red heels, her makeup was freshly applied, heavy and perfect and she smelled of the same perfume that Jennifer thought might be Poison. The deep red satin contrasted magnificently with Katya’s ivory skin.
It felt a little strange sitting beside the woman whom she had only recently fucked but Katya did not seem the least bit perturbed. Jennifer watched her stripping the metadata off the photographs she had taken of Jennifer then she cropped selected images and adjusted the white balance, exposure and contrast, colour vibrancy and saturation, and sharpened the images.
“You look good eh? Like a little girl dressed to look older. Not happy but compliant,” Katya explained.
Jennifer read between the lines. She would stay here at the safe house while Uri and Katya prepared her and then she would be handed off to one of Dmitriy Yakovich’s people smugglers.
She was not looking forward to leaving the comfortable, centrally heated cottage to be taken who knows where but she understood the machinations of it all. Katya uploaded the images to a secure website.
“Ok. It won’t take long for Vlad to bite or reject you but he will bite. There are not many twenty-year-old pretty trans girls around for sale. Well not, how you say, American white-bread girl, anyway. Uri; how is dinner coming?” she called into the kitchen.
“You women set table, open wine and food will be ready soon,” Uri called from the kitchen from which delicious odours were emanating.
Jennifer didn’t realise how hungry she was. She hadn't eaten since the room service she’d had at the Conrad. She helped Katya set the table and Uri brought in a series of dishes and arranged them in the middle of the table. Katya poured wine and then they settled in and began to eat.
“Uri is good at many things. He’s a good fighter, good driver, good with money, good drinker, good fuck but he is also a good cook,” Katya leaned across and kissed him.
Jennifer had wondered if Uri and Katya’s relationship was more than just professional.
“Katya good at all those things too and she a lot smarter than me but lousy cook,” Uri downed his glass of wine in one long gulp and poured another.
“My wife was a lousy cook too so I had to learn to be good cook,” Uri forked a varenyky dumpling into his mouth.
“My husband was a lousy fuck but a good cook,” Katya shrugged her shoulders and shovelled a spoonful of borscht into her mouth.
“Ok. Need backstory. We have new identity documents for Jennifer Edwards. Good to keep same first name so you not become confused when called. Good backstory is same as real life story but altered only as required to fool interrogators. Easy to lie when most of lie is truth,” Uri counselled.
Uri and Katya looked at Jennifer expectantly and she realised that they wanted her to tell them her life story.
She did.
*****
Jennifer Jones
Jeremy Jones knew that something wasn’t right very early in his life. It wasn’t just that he was small and effete; he just didn’t feel right in his skin. He felt most right when he surrounded himself with feminine things. Not dolls and unicorns but books written from a female perspective (he loved bodice-rippers and identified with the heroine rather than the hero), he liked fashion (women's not men's) and he was a swimmer and a runner who also played soccer whilst most of his male classmates pursued football, baseball and hockey. He did enjoy rock climbing and was a good shot with both rifle and pistol.
Jeremy preferred his own company. He wasn’t really bullied; he just didn’t fit in and honestly wasn't interested in most ‘boy things’. Fiercely independent and headstrong, he didn’t care what others thought about him or the way he perceived himself and the way he presented himself. He began experimenting with makeup at a very young age and began to secretly dress enfemme.
Eventually he was caught. Jeremy’s mother, as diminutive as he and fatally attractive, suspected her son was crossdressing long before she caught him in the act. Jeremy and his mother had a long honest conversation about how Jeremy felt and the state of his sensibilities and his deep-rooted emotional state. She took him to a phycologist who referred him to psychiatrist who diagnosed gender dysphoria which came as no surprise to Jeremy or his mother.
It was Jeremy’s father who was horrified and outraged that his son was a sissy faggot (his words - not anyone else's). The family quarrelled and Jeremy’s father threatened to send him to a military school to ‘toughen him up’. Not that Jeremy really needed toughening. Despite being diminutive he was fit and wiry and could outshoot his father at the range.
Jeremy’s father had always been disappointed in him and Jeremy’s diagnosis confirmed to him that his son wasn’t right in the head. Jeremy was dispatched to a conversion therapy camp where he spent the most agonising eight weeks of his life and came home suffering from depression, anxiety, and feeling suicidal but remained ‘uncured’.
His father felt thwarted and betrayed by a wife who supported Jeremy and condoned Jeremy presenting as femme. There was no prolonged bickering, no late night fights, no drunken rages or custody battles. Jeremy’s father simply took the opportunity to walk away from a marriage he was done with and a wife and son who had bitterly disappointed him.
This left Jeremy and his mother financially marooned. Jeremy’s mother Sally was an attractive woman who had married his father right of high school and didn’t have any further education or employment skills. She could be a waitress, work in sales or be a room attendant, all of which she did to make ends meet. Sally was determined that Jeremy was not going to end up without the education he deserved.
Jeremy was top of his class in every subject and had already developed a fondness for the law. He dreamed of being a high-flying legal-eagle but in his dreams he was a she with flaming red locks, killer makeup, dressed in a short-skirted business suit. Sally allowed Jeremy to present as female at home and present as androgynous outside. Jeremy made no secret of his desire to become a woman but he didn’t push his agenda on others.
Enter Uncle Raymond. Raymond was not really Jeremy's uncle but that’s how Sally and Raymond preferred Jeremy refer to him. He was a man of some wealth and means and Sally had caught his eye and she was allured by his handsomeness, his personality and generosity. Sally might be a small gal but she was drop-dead gorgeous and dynamite in the sack.
Sally put it right up front that Jeremy was gender dysphoric and that if Raymond wanted them to live with him under his roof he would have to accept Jeremy as Jennifer, Jeremy’s femme alter ego. Raymond was not only understanding, he was supportive. He paid for Jennifer’s medications and surgeries including breast enhancement, some facial procedures and a tracheal shave. He also paid for Jennifer’s psychiatric support during her transition. In consultation with Sally and her psychiatrist Jennifer stopped short of genital reassignment because it was irreversible and because Jennifer felt she didn’t need it, at least not yet. If she changed her mind she could always undergo the procedure later in her life.
When Jennifer presented herself to the world as a trans-woman it surprised nobody who knew her.
But Jennifer was soon to be heartbroken. She had finally become the woman she wanted to be when her mother was diagnosed with an aggressive form of cancer that killed her in three months. Raymond was heart-sick too but life goes on. Jennifer was already in college but she continued to live under Raymond’s roof. Raymond remained supportive but Jennifer sensed that with her mother gone, Raymond was becoming more aloof and distant and was using the bottle for a crutch.
Despite or more likely because of her dysphoria Jennifer performed exceptionally well at school and had skipped a couple of grades and entered college at sixteen and began to study law. Two years on and Jennifer was a stunning young eighteen year old who still looked like she was fifteen when she wasn’t wearing makeup.
Because she was so busy studying and when she wasn’t studying she was engaged in swimming, rock climbing and running; she had given up team sports, Jennifer didn’t really have the time to think too much about sex. As she got older she had of course been approached by young men. Because she was so attractive and sweetly diminutive and made no secret that she was transgender she was coveted by certain types who pursued her with little success.
Masturbation and online pornography fulfilled Jennifer’s needs. She had no doubt that she would find a suitable man when the time came. She had no dreams of a white wedding or of settling down in suburbia with a loving husband or of adopting children. Jennifer was alone in the world with no other family except for those on her father’s side who despised and had disowned her and her uncle Raymond who seemed to be over Sally’s death and was actively pursuing short-term bed partners.
She was also aware that Raymond was becoming very forward with her. He kept telling her how much she looked like her mother and how pretty she was. She could feel his eyes on her ass when she wore her tights to go climbing or running and all over her body when she wore her swimsuit to go swimming.
Jennifer was not really perturbed because he was her uncle Raymond after all. He was also paying her bills and putting a roof over her head so she couldn’t afford to get him offside. Did she tease him a little? Maybe? She liked girly things and when she was home she didn’t dress down like most of her classmates. She liked little skirts and tight low-cut tops to show off her new rack, she liked nylons and makeup and heels. It almost seemed that because she had recently transitioned she had a need to present as ultra-feminine to juxtapose herself from her past.
Raymond cooked Jennifer a sumptuous dinner on the evening of her eighteenth birthday. They had celebratory drinks before dinner, wine with dinner and champagne with dessert and Jennifer felt a little tipsy. Raymond, like many others, believed the MDLA of 21 was a joke in a country that sent teenagers to war and let Jennifer partake freely in the booze he had provided.
Jennifer had dressed for the occasion in a red satin evening gown, flesh-toned fifteen denier sheer-to-the-waist pantyhose, red high heels, heavy put perfect makeup including cherry-red lips to match her dress and had her crimson locks piled high in an up-do. She looked beautiful and sophisticated but because of her size and her fresh looks she still looked her age. She was not wearing panties because she didn’t want to spoil the lines of the dress and she wasn't wearing a bra because the tight bodice of the dress supported her perky breasts perfectly.
Jennifer wasn't sad that she had no friends to share the happy event of her transition into womanhood but she was sad that her mother was no longer here to celebrate her becoming an adult.
Raymond did his best to make it a celebration, even offering to take Jennifer to a club but even with a fake ID she doubted she would gain entry; she just looked too young, besides Raymond was far too drunk to drive anywhere.
Instead Raymond put on some music, her mother Sally’s favourite playlist, and they danced in a cleared area of the lounge room. Jennifer was melancholy but content. She counted her blessings. The alcohol had made her mellow and she rested her head on Raymond’s chest contentedly as he held her close and they shuffled around the lounge room.
She wasn’t sure when she actually realised that Raymond was erect, but at some point in the evening she became aware that his penis was pressing into her belly. She didn’t want to embarrass him so she let it go. Having the same privy parts she knew that males often became aroused at the most inopportune times.
But when Raymond began to grind his erection in a circular motion on her body she knew that it was not just random penile tumescence that sometimes plagued Jennifer when she was tucked. Raymond was aware that he was aroused and he was furthering his arousal by pressing it against his de facto niece’s body. Raymond lowered a hand to her bottom and squeezed it gently.
Jennifer raised herself on her tippytoes.
“Please don’t do that Uncle Raymond,” she whispered in his ear.
That actually made matters worse.
Her sweet breath in his ear and her breasts pushing against him when she leaned in to whisper, inflamed her uncle’s passion. Raymond knew that his desire for this young woman was inappropriate. She was almost like family, like a daughter or a niece but Jennifer looked so much like Sally: so beautiful and sexy, she was even wearing her mother’s perfume, that Raymond found it difficult to supress his lust.
There was also the fact she was transgender. Raymond had never had a particular penchant for transgender women. He was not the type that entered ‘chicks with dicks’ into his web browser when the compunction for self-gratification overcame him. In fact he was firmly in the camp of: ‘there are no chicks with dicks, only guys with tits’ until he had met Sally and her daughter.
He had never thought of Jennifer as anything but female and been respectful and loving towards her. But with Sally now gone and Jennifer of age he often wondered what that beautiful young woman kept hidden inside her panties.
She had a fantastic body; there was no doubt about that. He should know; he’d paid for most of it. She paraded around the house in her short skirts, slinky tights, tight tops and tits out… he was only a man after all and even though he’d found solace in the one night stands he brought home from the bars, there was something about Jennifer lately that caused him an itch he needed to scratch.
Raymond also felt a little entitled. He’d taken Jennifer into his house and under his wing. He’d paid for her transition and was paying for her education. Wasn’t he entitled to a little ‘payback’ in return? It wasn’t like she was his real niece and she kept parading those long legs, pert tits and tight buns in front of him. It was like having a Barbie doll that he wasn't allowed to play with.
Raymond knew that he was rationalising but the feel of this girl-woman in his embrace: her tits pressing into his chest, her perky ass in his hands, her perfume in his nose, her breath on his neck was enrapturing and she hadn't actually said no had she?
‘Please don’t,’ wasn't NO!… was it?
Raymond squeezed Jennifer's buttocks again, feeling the satin of her dress slide over the slippery silky pantyhose underneath. His cock twitched and Jennifer felt it, as well as her uncle’s hand caressing her ass. She tried to ease away from him a little but he held her tight.
Jennifer wanted to make it all stop before it got out of hand. It had already got to the stage where they would both be embarrassed the next day but the situation was recoverable. At least she thought so.
When Raymond lowered his face to hers and tried to kiss her, Jennifer pulled her face away. Raymond held her tighter and chased her lips with his. He pressed his lips to Jennifer’s and sighed into her mouth and caressed her buttocks and his cock shuddered again.
Raymond was a handsome man and in another time and another place where Raymond had not been her mother’s lover Jennifer might have been tempted to let him take her virginity but this was very inappropriate. She told herself that as she held onto him to stop herself collapsing as he kissed her like she had never been kissed before.
Raymond’s muscled body pressing on hers, his handsome face so close, his soft sensuous lips on hers, the scent of his aftershave, the faint scratchiness of his beard on her soft cheek… the very manliness of him was arousing but so improper.
When Raymond slipped his tongue into her mouth she didn’t resist but she didn’t encourage him either. When Raymond put his hand between their bodies so that he could caress her nipples through her tight dress she didn’t resist but she didn’t encourage him either. When Raymond caressed her buttocks and rubbed her smooth satin dress against her glossy pantyhosed ass she didn’t resist but she didn’t encourage him either. When Raymond pressed his cock into her tiny body and ground it against her she didn’t resist but she didn’t encourage him either.
Being a law student Jennifer was very good at rationalisation. In class they were often asked to present an argument to prosecute an offence and then switch it around and offer a defence.
This was what Jennifer was doing now. She was condemning her uncle for molesting her whilst she defended her own actions for not fighting him off: she was too weak, she was the fairer sex, he was like family and should have been trusted, and he was twice her age and then some, so he should know better. All of her arguments held up under the scrutiny of the imaginary jury in her head.
Raymond was guilty and she was innocent.
But the defence had to be heard too: Why had she opened her mouth and let Raymond put his tongue inside her, why had she tentatively sought out said tongue with her own, why were her nipples hard and tingling with delight at the touch of his caress, why were her buttocks radiating rings of pleasure while her uncle kneaded and stroked them, why did being held against his firm muscled body make her feel like the woman she had always wanted to be.
And more importantly… why was her penis painfully erect against her perineum.
Raymond kept up the pretence that they were dancing and guided her toward the couch. She felt the edge of the seat on the back of her legs and when he gently pushed her she fell into the couch and Raymond followed her down so that he was lying on top of her.
“Don’t” she whispered when Raymond slipped a hand inside the split of her gown and began to caress her thigh.
Raymond smothered her objections with a passionate kiss which Jennifer found herself unable to resist. When he began to stroke her thigh through her glossy pantyhose she shuddered and sighed but she knew that she should put up a fight so she began to struggle. Raymond liked the feel of her small body writhing beneath him. He got to his knees and pulled down his pants and eased his erect cock out of his shorts.
Jennifer lay there gasping. She couldn’t believe this was actually happening. Then Raymond lowered his face to hers and she turned away but she didn’t flinch when he turned her face to his. He kissed her again and guilt coursed through her as she responded to the man who had once been her mother’s lover. When he guided her hand to his rampant penis she instinctively gripped it.
It was the only penis she had ever held beside her own. She liked the turgidity of it, the sleek flesh of the veiny shaft and the spongy mass of his glans as Raymond thrust his cock against her. Raymond was enraptured by the feel of Jennifer's fingers lightly grasping his cock and his glans rubbing on her satin gown when it pushed through her fingers.
The feel of Raymond’s throbbing penis in her fingers and pressing into her belly was exciting and empowering, even though she knew it was wrong. Her own cock was uncomfortable, cramped inside her pantyhose tucked between her buttocks where it was throbbing and leaking pre-ejaculate.
When Raymond’s hand slipped into the crevice where her thighs met her torso and caressed her there it felt like butterfly wings tickling her tender flesh. When it moved across her pudenda and between her legs she tried to clamp them shut but it was too late. Raymond's fingers caressed her swollen organ and she craved for it to be released. The pleasure and the pain were inseparable.
She sighed into his mouth when Raymond eased her bloated phallus from between her legs. Raymond moved her penis so that it lay flat against her belly, held there by the gossamer gusset of her pantyhose. Raymond caressed it and kissed her harder and Jennifer drummed her heels on the couch and struggled to get free but Raymond's muscled body pressed her down into the couch.
Jennifer justified to herself that she had tried her best when Raymond pressed his cock against hers and began to hump. Jennifer knew about frottage but she didn’t realise how wonderful it would feel as Raymond’s pulsing manhood rubbed on her own turgid cock.
Jennifer returned Raymond’s kisses, driving her tongue into his mouth. She wrapped her legs around him and pulled him tight. She was close to climax and thought that Raymond would be as well. She could live with it if there was no penetration. What they were doing wasn’t much more than foreplay and they were both intoxicated so they could justify it… laugh it off as an illicit drunken tryst.
Jennifer knew that her red sheath dress was close to being ruined when Raymond pulled down the bodice and exposed her breasts so he could suckle them. The seam on the side pleat was already torn where Raymond had tugged at the skirts so he could get his hands on her thighs and her ass.
He was cupping her buttocks grinding his cock against hers through her gossamer pantyhose while he suckled her breasts, using his lips and teeth on her nipples. Jennifer’s head was thrown back, her hair wildly tousled, her lips parted as she begged him to stop.
“Please, stop, please don’t,” she whispered, but the lust in her voice betrayed her.
What Raymond heard was ‘please don’t stop’ or so he justified to himself.
When Jennifer felt his fingers go back down into the crevice of her ass and begin to claw at her pantyhose gusset she really began to struggle. She was not ready for this!
Raymond held Jennifer down with his bodyweight and guided his cock to the hole he had torn in Jennifer's pantyhose. He nestled his glans in the little virgin winkle of her sphincter and Jennifer stopped struggling and froze. Raymond’s cock was slick with his own pre-cum and Jennifer’s pre-seminal fluid and she could feel more of the little droplets oozing from the eye of Raymond’s penis.
“Please don’t,” Jennifer’s beautiful green eyes enhanced by her heavy mascara and eyeliner had a pleading look in them.
But was it a pleading look implying that Raymond should stop what he was doing or was it a pleading look that implored him to deflower her?
When Jennifer lifter her legs and wrapped them around his body Raymond took it for the later.
He lowered his mouth to hers and silenced a scream as he slowly pushed his glands through the tight clutch of Jennifer’s sphincter and inside her anus.
He stopped there.
Jennifer felt the most incredible pain as Raymond’s rock-hard penis pieced her anus. There was only an inch or two inside her but the pain was undefinable. But not for long. Raymond had the good sense to stop and let Jennifer get used to accommodating his penis in her tight rectum.
After what seemed like an eternity the pain began to subside. Not completely but it was replaced by a wondrous feeling that Jennifer had never felt before. The delicate nerves in her sphincter and her anus began to tingle. The feel of the man-flesh filling her back passage was actually pleasant.
Jennifer had stopped struggling and sobbing and she was sucking on Raymond’s tongue. Raymond felt an almost imperceptible little kick from her heels on his flank, like one might use to encourage a horse to canter and Raymond took his cue.
He took his time and he had to. He was so close to coming. This gorgeous creature's anus was gripping his manhood, almost resisting him as he pushed himself further inside her. She would give a little whinny when the pain returned and he would stop. Then Jennifer would give him another little kick when she was ready and he would slowly begin to push again.
As Raymond’s bloated phallus began to fill her back passage Jennifer began to experience the most delightful sensations ringing out from her anus. Her cock was steely-hard and Raymond could feel it pressing into his belly.
Jennifer whimpered and began to shake when Raymond’s glans pressed on her prostate and it immediately triggered Jennifer’s orgasm. She began to writhe violently beneath him, wrapping her arms and legs around him and rising up off the couch to bury all of Raymond’s cock deep inside her tingling rectum. She screamed into his mouth as her boiling spend spurted from her penis. Her cock was tingled with the most delicious sensations and her anus was awash with delight, a deep gratifying magical buzz was radiating from her prostate.
Raymond had never been inside a cunt that was as tight and glorious as Jennifer’s ass and when she rubbed her nylon-sheathed legs on his flanks and pulled him deep inside her, kissing him with abandon, he had no recourse but to climax along with her. He could feel Jennifer’s hot cream saturating his belly as he unloaded his issue deep inside her.
Jennifer felt Raymond's cock judder in her bowels. His semen lubricated her back passage and when Raymond began to fuck her so hard that he literally drove her into the couch she hung onto him and squealed with delight as her orgasm intensified and then slowly began to abate.
When they had both peaked and plummeted from their climaxes Raymond lay still on top his tiny niece, his cock still inside her but slowly deflating. Jennifer could feel Raymond’s semen dribbling from her sphincter and soaking into her dress and Raymond could feel Jennifer’s spend cooling on his stomach.
The enormity of what they had done was suddenly apparent to them both.
Jennifer remained silent when Raymond disentangled himself from her, his cock slipped from her anus releasing a dribble of semen. She felt like a slattern lying there in her torn dress and pantyhose with her dead mother’s lover’s semen dribbling from her ass.
Raymond buckled his pants as he shuffled off to his bedroom, saying nothing, feeling guilty but at the same time feeling more satiated than he had ever felt. He cleaned up in the half bath and heard Jennifer down the hall using the shower. He turned out the light and climbed into bed filled with guilt, wondering what he was going to say to Jennifer the next day.
A few minutes later his bedroom door creaked open and the miasma of Jennifer’s perfume preceded her into the room. He felt her pull back the covers and climb into his bed. She was wearing pink rayon babydoll pyjamas and hold-up stockings. He couldn’t see them but he felt them as she snuggled up to him. He could taste her lipstick as she softly kissed his lips.
“We need to get some lube tomorrow,” she whispered in his ear as she took his burgeoning erection in her little hand.
Jennifer obtained her law degree in three years and went to work as a judicial clerk for a federal judge whilst earning her master’s degree and passing the bar exam. Although she had specialised in criminal law she had yet to practice and at the age of twenty three she made an application to the Federal Bureau of Investigation. She had seen enough of the criminal justice system to turn her away from the drudgery of the courts. Her time clerking for the federal judge counted as work experience and she met all the other employment requirements and the slipup by the bureaucrat who directed Jennifer to complete a Reasonable Accommodation Request ensured that she had to be recruited.
She had moved out of Raymond’s house as soon as she graduated and started clerking. By then Raymond and Jennifer knew that their relationship was doomed not only by their age difference but by the lingering guilt they both felt about Jennifer fucking the man who had been her mother’s lover. Their parting was amicable and by then Raymond had found a nice little cabaret singer who tickled all of his fancies and eventually Jennifer and Raymond stopped calling each other.
Jennifer liked living alone. She had her appetites and she appeased them usually with one night stands or sometimes she engaged professionals. She had no time for a serious relationship; her heart was set on graduating from the FBI academy and becoming a field agent for the Bureau.
*****
“Story is good mostly,” Uri nodded his head and looked at Katya who agreed.
“Like part where you live with uncle and he’s fucking you,” Uri chuckled.
“You know he wasn't really my uncle right?” Jennifer furrowed her brow.
“Yes I get it. You just call him uncle because he fucking your mother until she died. All that works. Except part where you graduate college. Man who place ad want educated girl but twenty years old or less so you are twenty and still in college. Use same college because you familiar with it. But you still working on degree and have to work part time in convenience store because uncle not paying way through college.”
Uri explained the rest of the backstory. Jennifer is working part-time at the University Market and Deli to help pay her way through college. Katya sees her there and offers Jennifer a modelling job; if she’s interested she’s to meet Katya at the Starbucks just down the block.
While she is drinking her coffee Jennifer begins to feel woozy and has a vague recollection of Katya helping her out of Starbucks and into a car. Next thing Jennifer knows she wakes up at the cottage where Katya keeps her drugged and takes pictures of her which Katya insists are for her modelling portfolio but Jennifer is not stupid and realises that she has been abducted but is too drugged to fight.
“You're very certain of yourself,” Jennifer sounded sceptical.
“Spotters working for Dmitriy’s organisation keep eye out for potential girls. Always looking for young pretty girls. Special girls for special orders and Katya find you. Is perfect,” Uri grinned.
“Where they find pretty young trans girl like you, already have top surgery? Not hooker, not porn star… poor little Jennifer Edwards working hard to put herself through college, abducted by nasty Ukrainian lady and sold to Dmitriy’s people,” Uri rubbed his hands together again.
“Ok. Go with Katya and examine documents. Practice backstory and get right. Not much time. You must be Jennifer Edwards by tomorrow,” Uri pushed his chair out from the table and stood.
“Tomorrow!” Jennifer said heatedly.
“Tomorrow we hand you to Vlad. Need to have everything in place when he collect you,” Katya explained.
Katya stood too and put out her hand indicating for Jennifer to join her. They went upstairs to Jennifer’s room and Katya opened a valise containing Jennifer’s new identity documents: a social security card, a driver’s licence issued in Maryland, a University of Maryland student ID card and a Bank of America credit card. The cards were sufficiently scuffed and worn to look authentic.
“Learn your social security and student ID numbers. The bank account in your name has three hundred and twenty seven dollars in it with records of transactions for last two years including deposits from the University Market and Deli where you worked until I drugged you in the Starbucks on St Paul Street,” Katya explained.
Jennifer knew that area well. It was about three miles from her old college campus. She knew that the ability to set up legitimate social security, driver’s licence, student ID and a bank account in a false name in such a short amount of time could only have been done using the Bureau's resources. Donald Chase had been busy once she agreed to the assignment.
Jennifer spent the rest of the evening going over her backstory with Katya who finished the evening questioning Jennifer to make sure she had it right.
“Ok Jennifer your life depends on this,” Katya tapped an innocuous little black box.
“This is a GPS tracker with a long-life battery. We will be able to track you to within five meters accuracy,” Katya tapped the little box with a painted nail.
Jennifer imagined a dark room at Quantico where a man sat behind a bank of computer screens intensely watching a little blip on the screen which indicated her position. She would be disappointed to know that it would be just Uri, Katya or Chase watching her on an app on their phones or a laptop. No one at Quantico knew where Jennifer was or what she was doing except Donald Chase and Mike Cole. The Director knew about the op but not the details. He wanted plausible deniability.
“When you eventually make contact with Dmitriy Yakovich and have enough evidence that you can testify against him you activate this button,” Katya tapped a recessed button on the small device.
“Only when you are certain, don’t panic and set it off early,” Katya said sternly.
“How will I know him when I see him?” Jennifer rightly asked.
Katya held up her phone and showed Jennifer one of the few pictures ever taken of Dmitriy Tanas Yakovich. Jennifer shivered involuntarily.
Uri poked his head around the door.
“Hey girly. You want join us tonight? Last night of freedom for a while; good fun. Threesome,” Uri grinned.
“Thanks for the offer but I think I’ll graciously decline,” Jennifer gave him a wan smile.
“Sleep well. Remember your backstory. Tomorrow the game is afoot,” Katya leaned in and kissed Jennifer’s cheek affectionately.
But Jennifer didn’t sleep well. The walls were thin and she heard bedsprings bouncing, moans and groans and other sex noises coming from Uri’s room for hours on end until Katya finally left Uri’s room to sleep in her own bedroom.
Jennifer fell into a fitful sleep and was up at first light.
She showered, fixed her makeup and dressed in a little black skirt and jacket with a red satin blouse under. Her pantyhose were glossy and flesh-toned, black high heels and the jewellery that Katya had given her completed the ensemble.
“Ah good, you are ready. Come we will pack your suitcase and I will show you where we will hide the tracker,” Katya put out her cigarette and led Jennifer upstairs.
When Jennifer was packed and ready to go Katya put her hands on Jennifer’s shoulders and looked down at her. Towering over Jennifer, Katya looked pale and sombre.
“The next few days will not be pleasant. Don’t panic; just remember it is only a job. No one is going to hurt you badly because you are an expensive commodity… but men will be men,” Katya shrugged her shoulders.
“Just keep your eyes on the prize: Dmitriy Tanas Yakovich,” Katya patted Jennifer’s cheek.
“Now it gets real. You will feel a little sting but then you feel good,” Katya whipped out a hypodermic and injected Jennifer in the neck.
Jennifer’s feet fell out from under her and Katya caught her and eased her onto the bed.
“Sorry kid, I have to make it look authentic,” Katya took off Jennifer’s jacket and rolled up the sleeves of her blouse.
She pricked the inside of Jennifer’s arm a couple of times in the crooks of her elbows and rubbed the wounds until they bruised.
“Now it looks like you’ve been kept drugged for a couple of days. Time to meet Vlad,” Katya said.
To Jennifer it sounded like Katya’s words were coming from a swirling dark well. She felt like she did just before she went under anaesthetic. It was a pleasant buzz but disconcerting that she had so little control over her body. She saw the shape of Uri’s huge body and then he lifted Jennifer and carried her downstairs and put her in the backseat of Katya’s car then he returned for her suitcase and put that in the trunk.
“Good luck,” Uri kissed Katya hard.
“No luck involved Uri. This is all planned. Our future depends on that girl,” Katya turned her face towards the car.
“Good luck anyway,” Uri kissed Katya again and Katya climbed in the car and was gone.
To be continued
Comments
Good, but
Could have done without all the graphic sex scenes.
"Life is not measured by the breaths you take, but by the moments that take your breath away.”
George Carlin
Click bait
Yes, I'm loving the sex scenes. Well done. It makes for a nice balance. Thanks, Michelle
Michelle