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Tiffany is a high class call girl who moonlights as a poker dealer. After being caught rigging a game of Texas holdem she is fired but another opportunity comes her way. This four part story is the tale of a young transsexual girl who overcomes adversity and goes from being used to a position of power.
Author's note: I know very little about playing poker. I have played blackjack in a few casinos in the USA, Australia, Europe, UK, even Vanuatu but that's the sum of my experience with gambling. Blame any factual errors squarely on me rather than my researchers: Google and Netflix. As always, your comments and criticism is welcomed. xxx Michele
Tiffany was not the original name on her birth certificate but she loved the name regardless. Her fingers were long and elegant, her nails blood-red to match her lipstick. Dealers were not allowed to wear rings to prevent them from marking the deck.
She flipped over the river card and there was a gasp from the small crowd watching the game of Texas holdem from behind the velvet rope. Tiffany flashed her green eyes at them and they immediately hushed.
While the pit boss was distracted by the crowd Tiffany tapped her little finger infinitesimally on the green felt surface.
She had turned two aces on the board, the ace of diamonds in the flop and the river card was the ace of hearts.
Ravi Singh's heart was beating like a drum. His hole cards were a deuce and the ace of spades, he had three of a kind in aces. He didn't hesitate and went all in, he'd been hammering Kurt Bentley all night and now was the time to finish him off. The crowd gasped again and the pit boss growled at them. The other two players at the table had already folded.
To the amazement of those watching Kurt went all in too. Ravi grinned as he revealed his prial but his grin became a grimace when Kurt showed his five and six of hearts, he had the ace, three and seven of hearts on the board to make a flush.
This time there was no shushing the crowd.
Kurt Bentley raked in his chips and left the table without a word after tossing Tiffany a hundred dollar chip.
"A hundred dollars you cheap asshole!" Tiffany screeched at Kurt when she entered his hotel room an hour later.
"You're getting half the pot sugar, don't get mad," he grinned at her.
She saw the two stacks of bills on the counter.
"That was the deal, an even two way split and a fuck," Kurt reached out for her.
"I honestly thought you were joking about the fuck. You really want that?" Kurt held her close and she could feel the lump in his dress pants.
"You bet I do," he pulled her closer and tried to kiss her.
"Ok. Make it quick, I gotta run," she wiggled free of him and leaned against the counter, presenting herself for him.
"Jesus Tiff, where's the romance? Don't I at least get foreplay?"
"You want foreplay, play with yourself, I'm in a rush," she hiked her dress up and out the way and handed him a tube of lubricant she had taken from her handbag.
"Don't get any semen on this dress, it cost me a bomb," she looked back at him over her shoulder.
The casino was old-style and had a dress code, no grannies in tracksuits putting quarters in the slots here. Men were required to wear a suit and tie, women wore evening gowns or the equivalent. The male staff wore tuxedos and the female staff dressed accordingly.
Tiff was wearing a low-cut red satin sheath, it was split on both sides to the top of her thighs to show off her long legs clad in shimmering flesh-toned nylons. The bare-leg-brigade had no place in this casino where the cocktail waitresses wore micro-miniskirts, sheer pantyhose and four-inch high heels; every female employee was required to wear a skirt or dress, nylons and heels.
Tiffany yanked down her red satin panties and they pooled around her ankles, she kicked them away and tore off the surgical tape that was gaffing her. She manipulated her diaphragm so that her testes could descend down her inguinal canals into her scrotum, her large penis hung free between her legs.
"Come on, hurry up," Tiffany pushed out her creamy white buttocks, perfectly presenting herself for penetration.
Tiffany had a pragmatic approach to sex. She had been thrown out of home at the age of sixteen by her parents when their son declared that he would be going femme full time. Her parents thought that it was just a phase he was going through when he started crossdressing, just like when he went Goth and then Emo, but Tiffany, as she was calling herself by then, insisted it was no phase. She stated that she was genuinely gender dysphoric.
Tiffany ran to her aunt and uncle's place who were both sympathetic. Her uncle more so and he had taught her a few card tricks. He also taught her a few tricks she could do with her mouth and that her ass was not only for pooping. When her aunt caught them in flagrante delicto Tiffany had to put her new found knowledge to use on the street.
An enterprising pimp took her in and paid for breast implants and some other constructive surgery and got her started on hormones, all financed by the money she made for him. He turned an attractive young crossdresser into a stunning transsexual and then got her started in porn to supplement what she made as a high-class call girl.
Tiffany used sex like currency to get her way or to curry favour. Not that she didn't like sex, she loved it when she was in the mood with the right man or woman. Her tastes were eclectic.
Kurt moved in behind her, his trousers were down and his erect penis stood proud. He nudged her sphincter with his lubed-up cock and Tiffany pushed back, impaling herself on him.
"Jeez Tiff I wanted to tease myself a little before penetration," Kurt whined.
She placed his hands on her hips and began to rock back and forth.
"Shut up and fuck me," she wiggled her buttocks and adjusted her stance so that Kurt's glans pressed on her prostate.
"Hmmm, that's the spot lover boy, now get to fucking," her dirty talk spurred him on and he began to fuck her with long slow strokes.
Tiffany purred like a cat and pushed back to meet him, his hands moved to her thighs and his fingers entwined in the welts of her hold-up stockings. She encouraged him to quicken the pace, which he did. They were both panting, the thwok sound of his pubis slapping against her buttocks mingled with their passionate grunts and groans.
Kurt reached around and tried to take her in his hand but she brushed him away.
"Leave that alone, you'll only get it wrong, let me finish myself," she said through gritted teeth.
Tiffany masturbated herself while Kurt fucked her, she sensed that he was close when he held her still and drove himself deep inside her. Kurt gasped in her ear and she felt his hot spend fill her anus.
She held back until she felt Kurt was peaking and then she ejaculated, being careful not to get any on her shoes.
Kurt pulled up and adjusted his pants while Tiffany stepped into her panties.
"You put a runner in one of my nylons," she tsked while pushing her penis between her buttocks and pulling her panties tight.
"You just made close to a hundred grand and you're bitching about a ten dollar pair of stockings?" Kurt shook his head.
"I don't buy my hosiery at Wal-Mart you cheap prick," she fixed her lipstick, threw her compact and the lube into her clutch and hefted the wad of cash.
She tossed the cash and her clutch into a Gucci handbag.
"I'll count it later," she inspected herself in the full-length mirror, smoothing out her dress.
"You get any more action, you have my number," Kurt got the door for her.
"I'll email you to set up a meet, I don't like phones. And if you slap me on the ass on the way out I'll kick you in the balls," Tiffany pecked his cheek.
Kurt smiled, she had read his mind.
She nearly made it through the hotel foyer but was stopped by the concierge.
"He wants to see you," Serge raised his brows indicating it wasn't a request.
Serge was really Steve Goodman from Bumfuck Idaho who had started at the casino as a bellboy twenty five years ago. He had adopted an exotic ‘casino name’ and fake accent like a lot of hotel and casino staff did that worked the strip. He'd tip Tiffany off occasionally when a high roller was in town. She gave him a hundred and a hand job if the lead turned out to be productive. He had the option to forego the hundred and take a blowjob as full payment but Serge always took the money. He was so nervous the first time she rewarded him in the parking lot that he came all over her fingers as she was taking his cock out of his pants. She kissed his cheek, stuffed the hundred in his pocket and told him not to be so nervous next time, but for now to consider himself paid in full despite the premature ejaculation.
Tiffany turned around and took the elevator to the fourth floor where the counting room, the security room, and the hotel and casino managers offices were. She knocked on the door of the casino manager's office and entered.
"You're looking good Brian," Tiffany said, giving him her best smile.
"Bullshit Tiff, I look old and tired just like I feel," Brian was wearing a rumpled suit that he'd likely been wearing since five in the morning.
Brian Madsen didn't sleep much, the casino was his life. He'd never married and was devoted to his job.
Tiffany slid across the floor, her perfume proceeding her and announcing her presence. She deliberately sat on the edge of his desk so that her dress fell open revealing those magnificent legs.
Brian rested a hand on her thigh and sighed.
"What was our deal when you started here Tiff?"
"I attract the rollers, I make minimum and tips, and I give you a blowjob once a week," she smiled down at him.
As a reasonably famous transsexual porn star, accomplished croupier, blackjack and poker dealer, Tiffany was a drawcard. People would come to her table just to say that they had gambled with her. Security had to continually remind the mopes that photography was not allowed in the casino.
"What else?" Brian was not letting her off that easy.
"No scams, stings or trouble," she smiled meekly.
"Say, have you had your weekly blowjob?" she slid down off the desk, her satin gown rustling against her nylons.
Brian swivelled his chair round to face her.
She leaned down and kissed him, her tongue slid into his mouth. His breath was sour, whisky and cigarettes but she'd tasted worse, far worse.
Brian put a hand on the top of her head and instinctively she fell to her knees. She unzipped and unbuckled him with practiced ease. She freed his semi-erect penis from his underpants and improved his erection with her hand and then lowered her face into his lap to perform her duty.
She teased him, using the tip of her tongue on his fraenulum and then licking his glans whilst looking up at him with her pretty green eyes. Brian put his hand on her head again and applied pressure. Tiffany obligingly took him in her mouth and sucked him, working her lips on his shaft while her tongue lapped his glans.
"That's my girl," he grunted.
Tiffany worked her mouth, bobbing up and down, licking and sucking Brian's cock, swallowing his pre-ejaculate. He always came quickly and tonight was no exception.
Brian pushed her face down hard into his groin, she didn't like it when men did that but she willingly obliged this time. She took him deep and feathered her tongue on his glans and locked her lips on the base of his phallus as he spent himself. His semen filled her mouth and she had difficulty breathing but she kept to her task and allowed him to finish. She swallowed all that he gave her which was always a lot, she guessed that she might be Brian’s only form of sexual release. She swallowed the last of his issue and then licked him clean.
She got up from the floor and took a drink from the glass of bourbon on his desk, she swished it around her mouth and swallowed. Brian's semen was sweet compared to some that she had tasted but she wanted it gone from her mouth in case he wanted to kiss her, which he sometimes did after.
But not tonight.
She perched on the edge of his desk and fixed her lipstick.
"That looks like a decent roll you have there," Brian had picked up the bourbon and was sipping it, he nodded towards her open handbag.
She snapped it closed, guiltily.
"Let me show you something Tiff," Brian bought up a snippet of security video on his desktop computer screen.
It was the poker table she had worked tonight and the camera was zoomed in on the board.
"There!" Brian pointed to an infinitesimal movement of her little finger just after she had turned the river card.
"You're fired Tiff. There's probably not enough evidence to give to the cops or the gaming commission but I know and you know that you and that mope Kurt Bentley played mister Singh," Brian sighed.
"Ravi is making noises but everyone has him pegged as a sore loser. I know better of course," Brian shutdown the video.
"You waited until after I gave you a blowjob before you fired me!" Tiffany was pragmatic, she wasn't complaining, merely stating the obvious.
"Of course," Brian smirked.
"Hand in your security pass on the way out, the security boys will see you off the premises," Brian brought up a spreadsheet on the screen, he was done with her.
Tiffany had been thrown out of casinos before. Sometimes for shilling affluent highrollers and a couple of times for counting cards at the blackjack table but she had never been fired from a dealer job.
Two burly security guards accompanied her to the underground parking lot, which she thought was overkill, but at least they hadn’t created a spectacle by dragging her through the lobby and pushing her out the front door and making her wait indignantly for the valet to bring her car around.
She tossed her security pass at one of the guards and climbed into her red Dodge Viper, showing a lot of leg in the process. She kicked off her heels so she could use the pedals properly, you did not want your heels getting tangled in the pedals when you had a V10 engine with 640 horsepower under the hood.
Tiffany deliberately spun the wheels, leaving the two brawny men clouded in a miasma of burning rubber. She shot out of underground carpark with little regard for pedestrians or other traffic and replied to the cacophony of car horns with a raised finger out the driver’s side window.
She used the clicker to open the security door and parked her car under the condo building where she lived. She took the elevator to her one-bedroom apartment and locked the door behind her. The place was furnished Scandinavian style: simplistic, minimalistic and functional, featuring mostly grey and white furniture and fittings and polished blonde wooden floors. The odd rug and throw-pillow provided splashes of colour.
Tiffany tossed her heels on the couch, she did not want to damage her varnished Maple floors and more importantly her Christian Louboutin’s which had cost her over a grand from Neiman Marcus. She poured herself a generous gin and tonic from the small wet bar and looked out the window to views of Lake Tahoe.
She sipped her drink and considered her predicament. Money ran through her fingers like sand through an hourglass. Her condo was worth about three hundred grand with furnishings and fittings, her Viper was worth about one hundred and forty with depreciation. She had just made around a hundred grand from the Ravi Singh sting with Kurt Bentley but that was the only cash she had.
Tiffany had bought her condo when she worked for an LA pimp named Raffe Ignesman who also loaned her out to a pornography maker who owned Xavier Productions, a DVD and online porn distributor. Tiffany had to kick up a percentage of what she earned working as a high class hooker and porn actress to Raffe but she was still making a lot of money.
Some crazy tranny bitch named Sarah Carter had bought the whole thing crashing down. Something to do with trafficking young girls or some shit. Anyway Xavier Productions shut down, it was rumoured that Raffe Ignesman had been taken out by the Russian mob. Tiffany was left to fend for herself.
By the time that happened Tiffany had at least bought the condo and had a nice car and some money in the bank. She made enough working in casinos as a dealer and as a part-time call girl to pay her day-to-day expenses but she was now cash poor. The one hundred grand she had made tonight would be gone in a month. Tiffany had expensive tastes.
“I need a another job,” she said to herself as she stepped out onto the balcony and lit a cigarette.
No one was allowed to smoke in her condo and she herself only smoked when she drank or sometimes after sex.
She rolled down her stockings, and as Kurt had put a runner in one, she allowed them to slip through her fingers and float off with the breeze. The cool air on her bare legs felt good.
Her cell phone buzzed.
It was an alert from her website. Someone wanted to pay for her services.
Tiffany had been fucked once already tonight and had given Brian Madsen a blowjob that had turned out to be a waste of time and effort. Besides, it was way too late to go out on a date. But Tiffany charged two thousand dollars for a date and that was not to be sneezed at. Her website was password protected, the only people who had access to it were her current crop of clients. Potential new clients had to be recommended.
She kept her work as a card dealer and her work as a call girl separate from each other except for the very rare occasions she picked up a high roller at the casino. Her phone numbers and email addresses were unlisted, the only way prospective clients could contact her was through her website.
She opened the app on her phone and found she had one new message. She sat down on the lounge and tucked her feet under her. She reached for her tablet, it was easier than her phone when using her business app. The message was from a man named Stephen Bateman. He had references from two of her regular clients, one a high roller the other a wealthy entrepreneur. She tapped the thumbnails to enlarge his pictures.
Clients had to populate a profile on her website which included a recent face and full body picture and of course only she had access to the profiles. Tiffany wasn’t picky but she had standards.
Stephen Bateman looked to be in his fifties and he was handsome, very handsome. He had a mane of salt-and-pepper hair that had been stylishly coiffured, his features were chiselled and he had piecing blue eyes. She swiped to the body shot which he had taken of himself wearing only a pair of Speedos. He was tanned, fit, and didn’t have much body hair; it was likely he shaved or waxed. Unless he had stuffed a salami down his trunks he was also well endowed.
She read his profile. He was fifty-four and divorced. His occupation was listed as ‘other’ which was always interesting and he was looking for his first transsexual experience. His preference was to go for drinks and dinner somewhere public and see how things panned out from there. Her fee was guaranteed regardless of whether they consummated the evening or not.
Tiffany checked her Philippe Patek watch. It was nearly two in the morning but the little green button above Stephen Bateman’s profile icon glowed green which meant he was online. Her clients had to provide her with a phone number and email address, she knew the married guys kept discreet phones that they used only for liaisons such as this. Not that she cared that they were married, she made a living selling her ass so she couldn’t take anyone’s inventory.
She texted the number provided by mister Bateman.
‘You up? This is Tiffany.’
‘I’m looking at your pictures and videos. They have me up,’ he texted back immediately.
She smiled at the double entendre.
‘Too late to meet tonight of course. Tomorrow?’ she replied.
‘8pm the Grand Lake Hotel piano bar, ok?’
‘I’ll be there. Just click the link.’
The link she was referring to took the client to a payment page. Clients could use either a credit card or a secure online payment method such as PayPal to pay for her services. She didn’t care so long as they paid up front. She usually received a substantial cash tip from her clients too.
She drained her glass and watched the transaction take place and then Stephen Bateman’s online icon went from green to red. He was offline.
Tiffany raised her glass to the empty room.
“See you tomorrow mister Bateman,” she said dryly then arose from the couch to go to bed.
Tiffany had a lazy day the next day, she was still angry at losing her job but she put it all behind her. In the afternoon she worked out in her gym and then went to a yoga class. As time caught up with her she needed to diet and exercise more to keep herself trim and fit. She came home from yoga and stripped off her leotard and tights and looked at herself in the full-length mirror.
She was still striking. She wore her hair in a straight-cut bob with bangs. It was dyed jet-black with burgundy highlights and cut short to the base of her neck, flapper style. Her black hair accented her striking green eyes. Her lips were full, admittedly helped by just a tiny bit of botox; her skin was creamy white, she never saw the sense in sunbathing, all it did was age you. Most of her wrinkles had been taken care of with a facelift two years ago.
Tiffany’s breasts were a well proportioned 34C and very shapely. They should be, they had cost her plenty. Five years ago her surgeon had replaced her previous implants and had hardly left a scar. She tweaked a nipple and circled a finger around her areola and then hefted her bosoms in her hands.
“Not bad for an old girl,” she smiled to herself.
Her body was tight, her figure an hourglass although her pert buttocks were quite ample, not that she minded, nor did her suitors.
“Amazing what thousands of dollars worth of surgery and a weekly dose of hormones can achieve,” she flattered herself.
Tiffany knew that her best attribute were her legs; they were long, toned and blemish-free. Her legs were also alabaster-white but seldom bare, unlike most women today Tiffany loved hosiery. She had an extensive collection of tights, pantyhose and stockings, ranging from winter legging to ultra-sheer eight-denier stockings that she only wore on special occasions.
And then of course there was her cock.
She was very well endowed which was both a blessing and a curse. She liked having a large penis when she was having sex but it took quite a bit of ingenuity to tuck it. If she was going out for the day or going to work she would retract her testes into her inguinal canals and wrap her scrotum around her penis and tuck it along her intergluteal cleft and use surgical tape to hold it there. It was a very effective technique that she had mastered and she could even wear swimwear without any fear of being recognised as trans.
If she was just hanging around the house or was going out wearing a dress or a skirt on some mundane task she would just tuck herself and use pantyhose and tight panties to hold her genitals in place.
Tiffany had worked hard on herself. Surgery, exercise, diet and hormones had produced a transsexual woman who was almost indistinguishable from a genetic female. She never made an issue of being trans, if she was asked she acknowledged it but she didn’t broadcast it either. She had some notoriety as a former porn star but not many men were going to publicly admit to watching transsexual porn, but if she was questioned about it she admitted that in the past she had worked in the porn industry. There were plenty of ex-porn stars who were now legit media personalities.
The notoriety, like her cock, was both a hindrance and help. It sometimes popped up at embarrassing times when she was in distinguished company, some men and women couldn’t take a pornographic actress seriously. But her celebrity status sometimes helped, some casinos prided themselves on being gender inclusive and made a point of subtly advertising that they had a beautiful transsexual dealer who had once been a porn star working for them.
Tiffany was often asked why she hadn’t undertaken gender reassignment surgery and her answer was always the same. Whys should she? She liked being a transsexual woman and had no wish become what some referred to as a ‘complete woman’. She had many transgendered friends and a few had bought themselves ‘designer vaginas’ and some were happy and some were not. She was happy how she was.
She pulled on a pair nylon full-cut panties and slipped into a satin robe, she would shower later after her douche. She walked into her wardrobe. Designer clothes hung from both sides of the closet and the shoe racks were filled with Louboutin, Choo, Saint Laurent, Blahnik and Miu Miu. The drawers were filled with expensive lingerie, locked display cases filled with jewellery.
A simple black Channel cocktail dress was selected for tonight’s date with mister Bateman. It featured a sheer back and sleeves and was short, but not ‘hooker short’, it was best described as elegant but revealing. She debated whether to wear stockings or pantyhose and decided that pantyhose would be more practical. She took out a pack of Wolford Naked-8 pantyhose. They were black which was a colour she thought was passe in hosiery but in this case would go perfectly with the dress. Besides, being eight-denier they were so diaphanous that they were almost transparent but they would put some colour on her legs.
She would really like to wear her cherry-red Jimmy Choo ‘fuck-me pumps’ but they would be too garish and she definitely would look like hooker. She had the same pair in black so she chose those.
She unlocked the display case and took out a silver choker and matching drop earrings adorned with emeralds which would compliment her eyes. A simple silver bracelet and four silver rings joined the collection on the dressing table.
A black strapless bra was the obvious choice for the dress but she decided to spice things up when it came to panties. She selected a pair of red full-cut satin panties with black lace trim which she would wear over her pantyhose so that she could flash the handsome mister Bateman should she feel inclined.
With the clothes laid out on the bed and jewellery on the dresser there was nothing to do but wait. Still dressed in her satin robe, she smoked a cigarette out on the balcony while she sipped a gin and tonic; she would not smoke tonight because she hated the smell on her clothes and on her breath.
She padded to the bathroom and ran a bath while she took care of the practicalities of using the toilet and douching. When she had worked in the porn business she sometimes hardly ate anything for five days in a row when they were filming just so that douching was not such a chore. Men seldom understood the efforts their partners went through just so they could enjoy anal sex.
The remainder of her gin and tonic accompanied her to the bath where she luxuriated for about an hour. She stood up and rinsed off the soapy bubbles with the hand-shower and stepped out of the bath to moisturise her face, bush her teeth, and rinse with mouthwash. She walked naked to the dresser. First she took care of her tuck and gaff using the minimal amount of tape because the odds were that it would be ripped away sometime during the evening.
Even though she had been living as a woman for well over twenty years she still got a thrill out of putting on her makeup and dressing. She loved to make herself look pretty.
She favoured Chanel and Mary Kay cosmetics and she spent the best part of half an hour just doing her face. After applying foundation, finishing power and a little rouge, she gave herself dark smoky eyes using lots of eyeshadow, eyeliner and mascara. She applied three coats of Hot Red Max Factor Lipfinity lipstick to her lips, waiting five minutes between applications, then did the same with the top coat. Although a cheap lipstick at around fifteen dollars it was a lovely bright red but more importantly, it stayed on during prolonged kissing and oral sex.
She painstakingly applied a fresh coat of nail polish in a colour that exactly matched her lipstick and after it dried she brushed her hair one hundred strokes.
Happy with her face and hair she put on a pair of cotton hosiery-gloves and opened the Wolford Naked-8 pantyhose. After carefully taking out the cardboard insert she sat on the bed and slipped on the pantyhose one leg at time and then pulled the gusset up tight. Being eight-denier and sheer-to-the-waist they would snag or run easily, hence the need for hosiery-gloves. The pantyhose gently clung to her legs like gossamer and the dark hue flattered her pale legs. She liked the shine they gave when the light fell on her legs from certain angles.
Next she shimmied into her panties, carefully pulling them tight.
“Perfect,” she smiled to herself in the mirror.
Most women wear their pantyhose over their panties but Tiffany preferred the appearance of wearing the panties over, in her opinion pretty panties should be openly displayed, not hidden under a pantyhose gusset.
She put on and adjusted her bra and then sprayed her body liberally with Shalimar. One of her prize possessions was a bottle of Les Grand Extrait Chanel No 5 but as $4,200 an ounce mister Bateman would not be inhaling that tonight.
She stepped into her dress and adjusted it so it sat right then she sat down in front of the dresser mirror and put on her jewellery then she slipped into her Jimmy Choo’s. Finally she went over to the full-length mirror to check out her appearance and the ensemble. She looked amazing even if she said so herself. The dress was figure-hugging and clung to the all the right places, she turned sideways and admired her ample but firm derriere and then turned face on.
The hem rested eight inches above her knees which some would say was too short for a woman in her forties but not many women in their forties looked as good as Tiffany did. She once again ruminated about trying on the cherry-red heels but that would be going too far.
The Hot Red lipstick, the emeralds on her earrings and the burgundy highlights in her jet-black hair all accented her emerald green eyes, which she considered her next best feature after her legs. She smoothed out the dress and then threw her Chanel clutch and other ‘essentials’ such as a pair of fifteen-denier Wolford pantyhose for backup, another pair of panties, a compact makeup case, and a tube of lubricant into a larger handbag. She may stay the night depending on how things went. A final spray of perfume and she was ready to go just as a text popped up telling her that her car had arrived.
She deliberately gave the chauffeur a panty-flash as she got into the back seat of limo and again when she alighted. Tiffany couldn’t help herself from teasing the boys and from the grin on his face the driver knew she had done so deliberately and he appreciated the gesture as well as the fifty dollar tip.
The Grand Lake Hotel and Casino wasn’t really that grand. The hotel was fine, in fact it had a well-deserved five-star rating and the dining room, lounge and piano bars featured magnificent views of Lake Tahoe. The casino however was really a ‘pocket casino’ added to the hotel as an afterthought just because the law allowed them to do so. It had a hundred or so slots, twenty gaming tables and a poker room.
Tiffany went into the main hotel entrance and immediately turned heads as she followed the sign to the piano bar where once again she drew all eyes to her. She knew that all the men wanted to fuck her and that all the mature women hated her because they knew that all the men wanted to fuck her; but they were also jealous because she was so beautiful and confident. She doubted that many of the men would still want to fuck her if they knew she was packing a penis in her panties.
She gave Stephen Bateman her biggest smile when he stood up to greet her and pulled a stool back for her.
“Tiffany Bishop, so wonderful to meet you,” she extended her hand.
“Stephen Bateman and the honour is all mine. You are magnificent,” he beamed back at her with dental work that must have cost a small fortune.
He was even more handsome up close if that was possible and his ice-blue eyes roamed freely over her body checking her out. He was wearing a tailored black suit and blue silk tie with a white cotton shirt, obviously expensive. She liked men who wore ties with their suits and thought the open neck look that was so fashionable now looked like the man hadn’t finished dressing.
Stephen kept hold of her hand and helped her up onto her high-backed stool. Not that she needed a hand; at five foot nine inches Tiffany was quite tall for a woman.
Stephen Bateman did not make any attempt to avert his eyes from her legs as she stepped onto the stool and the hem of her skirt rose to the top her thighs. Why should he? He was paying two thousand dollars for the view. Tiffany pulled the hem of her skirt down a little in a vain attempt at modesty.
“Drink?” Stephen shifted his gaze to her eyes and was captivated by them.
“Gin and Tonic,” Tiffany smiled at him.
They had drinks and then moved to the dining room and had dinner although Tiffany barely ate anything. All through dinner they made small talk. Stephen had the amazing ability to engage her in conversation whilst never really telling her anything about himself.
He held her hand over the dinner table and made other romantic gestures and Tiffany could see that he was enraptured by her but he was guarded about telling her anything intimate about himself. Tiffany didn’t mind; it was his dime, or in this case, his two grand.
“So how did you come to hear about me?” Tiffany asked.
“Well I, ahem, had seen some of your screen work,” Stephen blushed a little under his tan.
“And I’d always wanted to experience the pleasure of dating a transsexual woman,” he smiled.
“By date you mean fuck,” Tiffany gave him a impudent grin.
“Yes I mean fuck,” his face flushed redder.
“Don’t be embarrassed, my intentions are honourable. That is I intend to honour your payment to me and pleasure you all night long unless I exhaust you or you kick me out,” she took his hand from the table and put a finger in her mouth and sucked it seductively.
A man seated near them stared at the couple with abject jealousy until his wife kicked him under the table.
“Where was I? Yes… so I asked around to see if you were still in Tahoe, still single and dateable. Turns out that a couple of my contacts advised me that not only where you dateable, that you dated for money,” he held her hand gently.
“That I fuck for money,” she gave him the same cheeky grin.
“I don’t think about it like that. I desire you yes, but now that I have met you and you have told me something of about yourself I also admire and respect you. I wouldn’t be disappointed if I spent the night in your company and we didn’t go to bed together,” his smile was infectious.
“Hey! I hope your not reneging on my plans to take you upstairs to your hotel room and have you shag me senseless,” she laughed audaciously.
“I want to kiss you so bad and make love to you so much that I almost can’t wait,” he laughed with her.
“Well unless you want a quick knee-trembler in the parking lot I propose you pay the bill and we go up to your room because I’m as anxious as you are to get started,” she bit her bottom lip seductively.
“I’ll use the rest room while you settle the bill,” she leaned in and kissed him softly.
Tiffany did a little prep work for the evening in the toilet. She removed her gaff, urinated, wiped, and then carefully pushed three little lubricant capsules into her anus. She tucked herself, pulled up her underwear, washed her hands, preened in the mirror and was ready for the evening’s entertainment.
They kissed in the elevator, Stephen held her close and pressed his lips to hers. She opened her mouth a little and let him slide his tongue into her mouth. When they arrived at the penthouse floor he had her walk ahead of him.
“I will be honest, I just want to look at those lovely long legs and that magnificent ass,” he said.
Outside the penthouse Stephen pressed Tiffany against the wall and kissed her passionately again. His hands roamed freely over her body, enjoying the feel of her bumps and curves encased in the tight black cocktail dress. A hand slid under her skirt and fondled her thighs and slid softly over the front of her satin panties, his fingers caressed flesh clad in the sheerest of nylon and softest of satin.
Stephen wondered how Tiffany managed to hide her genitalia. He had seen her movies and knew that she was very well endowed. It would be fun to find out he thought to himself.
He reluctantly released her and fumbled the passkey and almost dragged her inside. There was single lamp burning in the lounge and another in the bedroom, soft music was playing from somewhere. A bouquet of fresh roses were arranged in a crystal vase on a sideboard. They pawed at each other on the way to the bedroom leaving behind a trail of clothing. Stephen had somehow gotten down to his briefs and Tiffany had stopped briefly to pull off her dress and unclasp her bra but that was as far as she got before Stephen threw her on the bed and leapt on her.
Tiffany could feel the warmth and girth of his penis pressing on her leg as Stephen kissed her lips, her face, her neck and eventually her breasts. He kissed her nipples and then took one into his mouth and suckled it, gently biting the berry-shaped teat while Tiffany gasped and writhed under him. He licked her areola, using his mouth alternately on each of her breasts while he ground his cock against her.
Tiffany reached for him, releasing his engorged phallus from his briefs. It was quite substantial and seemed to throb in her fingers. He disengaged long enough to shuck out of his briefs and Tiffany took the opportunity to put her hand inside her pantyhose and untuck herself. She eased her semi-erect penis from between her buttocks where it was becoming distinctly uncomfortable.
Stephen saw what she did and the mystery of her hidden genitalia was solved. Tiffany hooked her thumbs in the waistband of her pantyhose and was about to pull off her nylons and panties together.
“Not yet!” Stephen put his hands on hers to stop her.
“I love the feel of those sexy nylons against my body and I want to stroke you through your panties for a while,” he grinned down at her.
“And I want you to,” she smiled up at him.
“I knew I should have worn stockings. These pantyhose are going to get ruined aren't they?” she put a finger in her mouth seductively.
“Oh for certain they are; but I’ll buy you all the nylons you want tomorrow,” Stephen smirked.
Tiffany reached for him and Stephen lay on top of her, supporting his weight on his elbows. He stroked her hair and kissed her, his cock pressed against hers through the layers of satin and nylon and Tiffany lifted her groin and slowly ground herself against him.
They both gasped as their penises rubbed together separated only by the diaphanous fabric of panty and hose. Tiffany had lowered her testes back into her scrotum and the crotch of her panties bulged like a posing pouch.
Stephen stroked her breasts and tweaked her erect nipples, he rubbed his legs along hers delighting in the feel of her nylons on his sensitive skin.
“I knew that this was going to be different but I never knew it was going to be amazing,” he sighed.
“Less talking, more kissing,” Tiffany pulled his face to hers and kissed him passionately.
Tiffany reached for him again and began to caress him with featherlight strokes of her fingers. She felt him palpitate and ooze a dewy droplet of pre-ejaculate which she rubbed into his glans with her thumb, pressing it against his fraenulum.
“Oh god I’m so close Tiffany. Can I just fuck you now and then we can make love all night I promise,” he gazed into her eyes and begged for release.
Tiffany nodded, her full, red, lips looked inviting.
Again she tried to hook her thumbs into the waistband of her underwear and again he stopped her.
“Oops,” Stephen smiled wickedly as he tore a little hole in the gusset of her pantyhose.
“Oops indeed,” Tiffany smiled back at him and opened her legs and pulled the gusset of her panties aside for him.
She took him in her hand and guided him to her puckered bud. The lubricant gel caps has dissolved but she grunted as his girth slid inside her.
“Are you ok? Am I hurting you?” Stephen looked genuinely concerned.
“It’s lovely,” she smiled up at him and pushed herself upwards to impale herself on his big cock.
She wrapped her arms around his shoulders and nuzzled his neck as her ankles locked behind his back, her nylon-sheathed thighs rubbing on his flanks.
“Now fuck me. Nice and slow,” she whispered in his ear and playfully bit his earlobe.
Stephen required no further invitation and began to fuck Tiffany slowly and deeply, pulling almost all the way out of her and then driving himself all the way inside her. He could feel her hard penis pressing on his belly and the slippery pre-cum leaking from her.
“I can’t hold back I’m sorry,” he mumbled through crushed lips.
She urged him on, rising to meet his quickening thrusts. His huge cock filled her anus and elicited the most wonderful, pleasurable sensations, especially from the ring of her sphincter and her prostate when his bulbous glans pressed against it.
“Fuck me Stephen! Fuck me!” Tiffany moaned as she writhed and bucked beneath him, meeting his thrusts.
The pleasure was indescribable, nothing in Stephen’s life could compare. Tiffany’s anus clung to his cock like a velvet glove. Her silken-sheathed legs grazed his tender flesh, her lips pressed to his, her tongue squirmed in his mouth; Tiffany was a sexual entity lying under him, pleasuring unlike anything he had ever experienced.
“I coming!” Tiffany clung to him, raking her nails on his back.
“Oh god! Me too!” Stephen pressed his mouth on hers and drove himself inside her as far as could.
The pressure of his penis against her prostate and the taut flesh of his belly pressing on her penis trapped between their bodies triggered Tiffany’s orgasm and she literally screamed as she climaxed. This triggered Stephen’s orgasm and he clung to her and smothered her cries with kisses as he ejaculted deep inside her. She drummed her heels on his lower back.
The two lovers held each other in a powerful embrace, kissing and nuzzling as simultaneously ejaculated. Stephen felt Tiffany’s hot semen squirt against his belly and she felt his scalding seed fill her anus.
They kissed and writhed against each other until their passions were exhausted but neither wanted to break their embrace. So they didn’t. Stephen lay on top of her, kissing her, stroking the bangs out of her pretty eyes and she kept him trapped against her body with her legs locked behind him.
“That was pretty awesome,” Stephen broke the silence.
“That was pretty fucking monumental,” she smiled up at him and stroked his face.
“I’m probably going to ruin the moment but I have to ask. Is it like this on all of your dates?” he stroked her face too.
“I’m going to be honest with you since you asked. Sometimes it’s good and sometimes it’s bad but it’s my job to ensure the client has a wonderful experience.”
“This does not feel anything like that,” she said seriously.
Stephen frowned.
“This feels like we are lovers,” she kissed his cheek.
“Me too. I’ve known you only a few hours and I already feel a deep affection for you,” Stephen softly kissed her eyelashes.
He reached down and pulled the covers over them. It was chilly in the bedroom but that only encouraged them to cling to each other. Stephen was still inside Tiffany, he hadn’t become fully flaccid, and in fact he was becoming fully erect again.
“Already?” Tiffany smirked.
“Already,” Stephen began to slowly fuck her.
Tiffany put her arms around him and kissed him.
On the occasions that Tiffany stayed overnight with a client it could be awkward in the morning but not so with Stephen.
Tiffany got up to use the bathroom and came back to bed still dressed only in panties and pantyhose because Stephen wouldn’t let her take them off. Then Stephen used the bathroom and came back to bed and they made love again.
They lay in each other’s arms exhausted.
“Did we get any sleep at all last night?” Tiffany lazily stroked his chest.
“I’m sore,” Stephen grinned.
“You're sore! My ass feels like it’s been fucked by a bull elephant. I mean that in a nice way by the way. And how did you stay hard all night for goodness sake?” she playfully waggled his penis which had finally become flaccid.
“With the help of my little blue pills,” Stephen grinned.
“Well they certainly work honey,” she squeezed his cock.
“Oh no. Most of that was you. You are so gorgeous and sexy that I probably didn’t need the pills,” he turned on his side to face her.
“I bet you say that to all the transsexual prostitutes,” Tiffany giggled.
When she saw the look of disappointment on his face she regretted saying it.
She moved in close to him and searched his eyes.
“I didn’t mean that. You are a wonderful man and last night was one of the most wonderful nights of my life,” she leaned in and kissed him.
“Thank you,” he sighed and kissed her back.
“No. Thank you. Now let me out of this bed so we can order breakfast I’m starving,” Tiffany grinned and threw back the covers.
Stephen admired the view as she gathered her clothes and purse and padded to the bathroom.
Tiffany emerged freshly showered but she had taken time to put on her makeup; nowhere near as daring as last night, but she had done her eyes and put on a light coating of lipstick.
“You know you even make that white terry-towelling bathrobe look good,” Stephen lay back in bed with hands behind his head.
Tiffany slipped into her heels and paraded coquettishly across the room. She did a little burlesque for him, laughing the whole time.
“Bravo, Stephen applauded her.
“Ok mister get out of bed and get showered. I’m calling room service and I want a big breakfast,” Tiffany sat down in the lounge and lifted the receiver.
“Order me what you’re having,” Stephen called through the door.
They had breakfast together chatting about nothing in particular and then Tiffany went back to the bedroom to change. She gaffed and put on clean panties and the Wolford pantyhose she had bought for backup. She retouched her lipstick and slipped into her dress.
She gathered all of her belongings and checked her phone. Nothing important. She came out the bedroom ready to depart.
“Wow! You look amazing,” Stephen was still taken with her.
“Yeah. Well it won’t be that amazing doing the walk of shame through the hotel lobby dressed in a cocktail dress and high heels at ten in the morning,” Tiffany teased him.
“You could always stay,” Stephen said solemnly.
“I could come back later tonight. I have things to do today,” she bent down to kiss him on the cheek, he was still dressed in his bathrobe.
Stephen grabbed her arm and pulled her into his lap.
“Please stay. I’ll put another two thousand into your account,” he nuzzled her ear, his hand strayed to her thigh.
“Look Stephen, I have to go, but when I come back tonight you don’t have to pay. It won’t be a business proposition,” she struggled to get out of his lap but he held her there.
“I actually have a business proposition for you,” Stephen went on.
“Have you ever heard of Lyle and Tina Brinkman?”
Tiffany paled.
To be continued.
Tiffany’s earliest memories are of her as a young boy growing up in the Midwest. To say that her upbringing was difficult would be an understatement. Although not particularly small for his age Tom Robinson was very lithe and almost effeminate in manner. From the outset Tom knew he was different. He began to feel trapped in a body in which he just didn’t belong, so he tried his best to make himself look like what he thought he really should.
He grew his hair long as soon as he was allowed to and dressed very androgynous. He had developed a fascination for lingerie, skirts, heels, makeup, and all things feminine. He took female roles in school plays and every Halloween he dressed as a female superhero or famous female movie character. Tom excelled at his academic studies and the arts but he was no jock. Much to his father’s disappointment he never tried out for football, baseball or track, but his long lithe body was suited to swimming at which he excelled.
Tom’s father had given up on his boy by the time Tom entered his teens but his mother doted on him. Kay was forever kissing and cuddling him. She knew about the collection of girls underwear, shoes and clothing that Tom had hidden away and she tolerated her son dressing up as a girl at home while her husband was away, which was often because he was military.
Tom would even dress in babydoll pyjamas or wear a satin slip to bed and often wore panties instead of briefs. He took every opportunity to dress enfemme. Needless to say these habits caused him to be ostracised at school by the jocks and popular students but he formed an allegiance with the fringe groups and eccentric cliques.
In his mid-teens he became a Goth. He was not particularly interested in their music and culture but feigned an interest just so he could dress enfemme. The Goth culture favoured androgyny and he could get away with wearing skirts, makeup, black pantyhose and jewellery. He dyed his hair black, had it cut into a shag, pierced his ears and painted his nails. Even the Goths he hung out with noticed that he seemed more attracted to gender freedom than the Goth lifestyle.
Both his mother and his father hated it. He was berated by his father who threatened to throw him out but Tom had a good academic record, performed well at swim meets, and didn’t get into any trouble.
Tom soon tired of being Goth, he wasn’t really into the culture and using it as an excuse to dress as a girl wasn’t worth the other bullshit he had to pretend to like. For a brief period Tom transitioned from Goth to Emo but he wasn’t the introverted, emotional geek that the genre proposed, so he decided to just be honest and come out to his mother.
He told Kay how he felt like he was really a girl not a boy. That he loved all things feminine and wanted to dress like a girl and present as female full time. The first question his mother asked him was about was his sexuality and Tom admitted to her that he was attracted to both girls and boys but unlike most of the teens his age he had not acted on them. He was still a virgin.
“Mom. I can’t live a lie any longer. From now on I’m Tiffany, a sixteen year old girl. Tom is no more,” Tiffany said defiantly to her mother.
“Ok Tiffany. Let’s see how that works. To start with lets go and get your hair done and buy you some decent clothes,” she patted her new daughter’s hand.
Kay took her new daughter out and did exactly that, getting Tiffany’s hair cut in a style that suited her, buying her clothes and makeup and even helping Tiffany present herself as a young woman. Kay told herself that it was just another fad but deep down inside she knew that her boy was not happy in his skin and as she watched as Tiffany blossom she wondered how her husband would take it on his return.
Tiffany’s father was away on a navy deployment for four months in South East Asia and neither Tiffany nor Kay had told him that Tom was now Tiffany. There were also problems at school. Although Tiffany’s school prided itself on being inclusive and tolerant the practicalities of a male student suddenly turning up one day and claiming to be female were very hard to deal with.
What toilet was she to use? Which team did she swim for? And of course the daily ridicule and taunting from the less tolerant students was awful.
Tiffany dropped out of school with the intention of completing her studies elsewhere when she had fully transitioned. Kay was heartbroken and fearful of her husband’s reaction, which she had every right to be.
When Tom senior returned home from duty overseas and saw his boy was now presenting as a girl he lost it. He threw Tiffany out of the house with all of her belongings.
“I’m going down to the CPO Club to get drunk. I want that freak out of my house by the time I get back!” Tom senior roared.
Kay arranged for her sister Shelley to take Tiffany in. Shelley was the family misfit who had left the family home as soon as she could to pursue a bohemian lifestyle. She had lived like a gypsy, moving around various communes and alternative cooperatives following her dreams. In her mid-forties she found that reality bites and that apart from her looks and her knowledge of all things arty and spiritual, she had nothing.
Shelley moved in with her partner Remy and they scraped together enough money to open ‘Bric-a-Brac’, a curio, trinket and antiquities store which did moderately well. Shelley had settled down with Remy but they had no children, nor did they intend to. Because of the rebellious alternative lifestyle that Shelley had lived she could identify with Tiffany’s struggle to be accepted living in a gender to which she was not born.
“A new city, a new home, and a new beginning,” Shelley hugged her new niece and welcomed her into her home.
The arrangement was that Tiffany would live with her aunt, who lived four hours drive away, and Kay would come to visit her daughter once a month.
Tiffany loved living with Shelley and Remy. She had her own room, was given all the freedom she wanted, and she worked in the store to help pay her way. Free of the bonds of her past Tiffany went about reinventing herself. With practice she was soon totally passable as a girl, a flat-chested girl, but a girl still the same. She had developed female mannerisms and patterns of speech and importantly, after exploring the Internet and with extensive practise, she learned how to tuck and gaff.
Tom Robinson disappeared off the face of the earth completely, replaced by Tiffany.
There were still many challenges ahead of her, she was still legally male and dealing with the authorities was difficult. Tiffany had to spend time under the care of a psychologist and get a sworn statement from her mother in order to get her gender altered on her birth certificate and a driver’s licence issued reflecting her new name and gender. But she counted herself lucky, some states required proof of sex reassignment surgery before they would change a person’s gender.
Living full time as a girl was both a relief and joy. She developed her own style and as much as Shelley encouraged her to adopt her bohemian-chic dress style of flowing embroidered skirts and ‘peasant look’, Tiffany decided to go to the other extreme.
Tiffany had developed a taste for eighties fashion, smart casual, and business wear. The exact opposite of her aunt.
“It’s so funny that I rebelled by wearing tie-dyed t-shirts and bell-bottoms and you rebel against me by dressing like a model out of a Robert Palmer music video,” referring to Tiffany’s pale skin and heavy makeup.
“Actually I think it’s good that we have totally different styles, you should present yourself to the world as you see fit,” Shelley encouraged her niece.
Tiffany initially spent most of her wages on clothes, makeup, and accessories, supplementing the accoutrements that her mother had bought her. Working in Bric-a-Brac she wore a uniform of her own design: a tight-fitting navy-blue skirt, white blouse, flesh-toned pantyhose and black high heels. Her makeup featured smoky eyes, bright red glossy lips and a little rouge on her alabaster skin to highlight her cheekbones. Tiffany had continued to dye her hair black from the days when she had been Goth because she liked the contrast of the black hair against her ivory skin. She wore it in a shaggy shoulder-length bob with bangs.
She was tempted to buy a pair of breastforms but discovered that a padded bra gave her just enough bosom. It suited her not to have large breasts, being tall, svelte and long-legged.
“I really like your look Tiffany. Very professional and it somehow works; me dressing like a hippy and you dressing like a businesswoman. You must be driving the boys wild,” Shelley beamed when Tiffany presented herself in the shop for the first time sporting her new professional look.
Tiffany blushed. She was still uncertain about her sexuality. She wasn’t particularly attracted to boys her own age but she was attracted to older men; she was also attracted to some women. When she masturbated her choice of pornography was usually transsexual women having sex with mature men but she also liked tranny-on-tranny porn. She found it all a little confusing and decided to defer engaging in a physical relationship until she was absolutely ready to do so.
Of course it didn’t take long for word to get around that a stunning young woman was working in the store. Bric-a-Brac was soon a regular haunt for teenage boys and young men who wanted to see the striking young shopgirl who worked the costume jewellery and trinket counter. Shelley was no harpy either and the young men often gave her a second look.
Tiffany remained shy around men and rejected any advances made to her. The extra traffic helped sales because the young men needed an excuse to be in the shop so they made purchases. The young men attracted young women, so the cycle generated an increase in income.
But it wasn’t just the young men who were attracted Tiffany. Remy had watched her blossom like a butterfly, transforming from a gangly young boy dressed as a girl into a sophisticated self-assured young woman who you would hardly guess was a genetic male.
He liked her style. He would never tell Shelley this but he thought she had become dowdy as she had gotten older and the ‘vintage-hippie’ thing was no longer appealing. Shelley was still attractive but Tiffany’s ‘killer-chic’ look was sophisticated, young, and sexy.
Even when she wasn’t working in the store Tiffany wore full makeup usually with dresses and skirts. She was seldom seen out of nylons and heels even on the rare occasions when she wore jeans, which she did with panache.
Remy was captivated by Tiffany and although he knew it was wrong, he desired her. He fantasised about having sex with her, she sitting in his lap kissing him, on her knees fellating him, bent over the shop counter while he fucked her. He knew that the worst possible thing he could do would be to try to seduce her but he couldn’t help himself when the opportunity arose.
“Don’t you guys burn down my store,” Shelley joked and waved goodbye out the driver’s side window of her Ram Promaster City van.
Shelley was off on her twice-yearly treasure hunt as she called it. Inspired by the TV show American Pickers she travelled around the bazaars looking to buy curios, small antiques, jewellery and baubles to sell at a profit in Bric-a-Brac. Remy thought it was a waste of time and money once you deducted gas, food and accommodation from the calculations. But this time he was glad to see her go. He would have nearly three weeks alone with Tiffany.
Because she had recently moved in and because of her unique situation Tiffany was pretty much a loner, although not really a recluse. She loved to go out and she loved to engage with Shelley and Remy but she was disinclined to form any friendships just yet despite the many offers from both boys and girls.
She and Remy had gotten very close and she had to admit that she had a teenage crush on him. He was a little younger than Shelley and incredibly handsome. He had his own style which Tiffany described as ‘urban cowboy’. She had seen him with his shirt off and he was toned, he worked out every day.
He and Tiffany played cards together and he taught Tiffany to do card tricks and sleight of hand. He showed her lifts and riffle deals where he was able to stack the deck and win every time. He also showed her how to ‘second deal’, how to count cards even how to mark a deck. He had worked as a blackjack dealer in Reno before he met Shelley.
Tiffany trusted Remy and asked him to take her swimming as she was embarrassed about being flat-chested and although she had to learned tuck and gaff she was not really confident about being seen in a swimsuit.
Not that she need have worried, although she was not at all endowed in the chest area she was still stunning in her black spandex Nike high-neck one-piece swimsuit. It clung to her like a second skin and the high neck averted attention from her meagre breasts and accentuated her long elegant neck and pretty face. The suit flattered her figure. She was a little self-conscious about her ample behind but she needn’t have been; it was sexy. Swimming gave her the opportunity to flaunt her long, toned legs. Her flesh looked almost translucent when the black spandex was wet and clung to her creamy white skin.
Remy took her to an indoor pool three times a week and it was one his favourite activities. He’d change into his Speedos and watch her swim lap after lap and ogle her whenever she got in and out of the pool. After her laps he’d join her in the pool and they would horseplay around. He took every opportunity to rub against her and often had to wait for his erection to go down before he could get out of the pool.
Tiffany was no fool and she knew what he was up to, but because of her infatuation with Remy she tolerated his behaviour. She also noticed that he liked to leer at her, particularly when she was dressed in her work attire. She deliberately teased him, bending over in his presence, asking him to hold the stepladder steady while she climbed it and sitting with her legs slightly open. Whenever the occasion presented itself Remy would brush or graze against her, he particularly liked to squeeze past her when she was behind the counter and his groin pressed against her buttocks.
Tiffany began to fantasise about Remy. He would take her in his arms and kiss her and then they would do unspeakable things to each other. She’d seen plenty of transsexual porn and knew how transsexual women used their mouths and anuses to satisfy men’s desires. She would wake up with her panties sticky and have to wash the sheets.
Shelley had only been gone one day when Remy made his move.
“Hey Tiff, wanna sit with me and watch some Netflix?” Remy called out to her.
Bric-a-Brac stayed open late on Fridays and Saturdays and it was Tiffany’s turn to lock up the store. They took it in turns working the late shift so it was dark in the house when she came in.
The living room was cozy, the only light came from the TV. Remy was sitting on the two-seater couch and he patted the space beside him.
“Come on and I’ll buy you a beer,” he quipped.
Shelley and Remy had a very tolerant attitude to drugs and alcohol and believed both should be used often but in moderation. Tiffany was allowed a beer or a glass of wine with dinner.
Tiffany, still dressed in her work attire, sat down next to Remy who popped her a cold beer and put his arm along the back of the sofa. His feet rested on a poufe and he schlepped it her way with his feet so they could share. Tiffany put her feet on the poufe and slipped off her heels.
“Lovely,” she rubbed her feet and wriggled her toes.
Remy leered at her feet and her cute toes sheathed in gossamer tan nylons, her toenails were painted bright red. His eyes followed her legs, her skirt had ridden up and the top of her thighs were exposed to his gaze. Tiffany felt his eyes on her and caught her breath; she pretended not to notice and sipped her beer. She was aware of how close they were on the couch, his body was almost touching hers and his arm was behind her on the back of the couch. She felt crowded by him. Tiffany could smell him too. There was a manly undercurrent to his scent, almost musky, despite that he was obviously freshly showered and applied aftershave and deodorant and used mouthwash.
And that was another thing she hadn’t noticed until she sat down. He was dressed only in a bathrobe and she suspected the expensive Dolce and Gabbana cotton-spandex briefs he liked. She and Shelley shared the laundry duties so she knew what type of underwear he wore.
“What are we watching?” Tiffany attempted to break the tension.
“It’s a show called Easy and this episode is called Art and Life,” Remy pointed his chin towards the TV and slurped on his beer.
“Oh my god,” Tiffany whispered.
A stunning young blonde bombshell dressed only in a black lace bra and pink panties worn under black sheer-to-the-waist pantyhose was taking selfies while lying on a couch. She moved into a bedroom and took more selfies with a man lying asleep on the bed behind her. They had obviously made love earlier.
The parallel of her and Remy’s current situation to the situation on TV was self-evident. A young girl dressed provocatively, uncomfortably close to a handsome older man. The difference being the man on the screen was asleep and Remy was wide awake.
“I like her pantyhose,” Remy pointed his beer can at the screen.
“I like that they are sheer-to-the-waist but I prefer flesh-toned nylons,” Tiffany croaked, her mouth was dry, she sipped more beer.
“But they look good over those pink panties though,” Remy countered.
“I wear my panties over my pantyhose,” Tiffany replied and immediately regretted saying it.
It was an incongruous thing to say given the situation.
“I know,” Remy’s hand alighted on her shoulder.
“How do you know?” Tiffany whispered.
“You keep showing me. I’m not sure if you’re doing it on purpose but I like it,” it was Remy’s turn for his throat to be dry and scratchy.
“I know you like it. I know you like to watch me in my swimsuit too,” Tiffany took a final pull on her beer and put down the empty can on the table beside her.
Remy followed suit.
Remy’s arm felt like a lead weight on her shoulder even though he was hardly touching her. She leaned in and put her head on his shoulder and Remy cradled her in his arm.
They sat like that, neither of them saying anything, for what seemed like an eternity. Tiffany summoned up all her courage and turned her face to his, the sweetness of her breath was provocative to him. He turned to face her and gazed into her pretty green eyes and leaned in and kissed her softly on the lips.
They kissed. Closed mouthed and tenderly. It was a beginning.
Tiffany stroked Remy's cheek and he brushed her hair out of her eyes and then they kissed again. Tiffany felt Remy's eagerness and she opened her mouth a little and Remy slid just the tip of his tongue into her, she nervously put her tongue in his mouth too. It was her first French kiss and it was amazing.
“This is so good,” Tiffany gasped.
“So good,” Remy kissed her again, this time a little longer and a little harder.
“I feel guilty about aunt Shelley,” Tiffany whispered.
“She’s probably getting laid by some redneck right now. We have an open marriage,” Remy lied.
He wanted this sweet, virginal girl so much that he would say anything.
Remy purporting an open marriage comforted Tiffany but she suspected the lie. Maybe they were open back when Shelley was on the road as a hippie for sure, but all Tiffany had witnessed since she’d been here was Shelley doting over Remy.
The pang of guilt disappeared when Remy took her hand and put it inside his robe.
She leaned into him and kissed him while her hand stroked his chest, she felt his muscled flesh through the matt of hair. Remy gasped as her fingers slowly moved down across his flat stomach.
“I’ve never done anything like this,” Tiffany murmured.
“You don’t have to anything you don’t want to sweet-pea,” Remy gazed into her eyes earnestly.
Tiffany leaned in and kissed him, pressing her lips hard against his and driving her tongue into his mouth. She was kissing him with passion and enthusiasm, her tentativeness gone. Her hand grazed over the front of his briefs and she felt the heat and girth of his penis through the slinky material.
“Oh Jesus,” Remy gasped into her mouth.
Tiffany lightly stroked Remy's penis through his shorts, feeling the heft of him, feeling the warmth, feeling it pulse. She was equipped the same way and she knew what she liked so she did it to Remy who was writhing on the couch loving it.
Tiffany was getting uncomfortable. She was sitting awkwardly, having to turn sideways to kiss and fondle Remy. More importantly, her own penis was becoming erect and it was casing her some distress.
“Just let me…” she disengaged briefly and Remy was more than a little disappointed.
But when she stood up and unzipped her skirt and let it pool around her ankles he was overjoyed. He gazed at her long coltish legs encased in the sheer, shimmery nylons. He reached out and traced a finger up her thigh stopping at the juncture where her leg met her torso. He smoothed the tiny wrinkles in her nylons.
Tiffany was shaking. She had stood to remove her skirt and gaff and had not expected Remy to touch her. But she loved it. It was the first time anyone had touched her this way and it felt wonderful.
She continued to do what she had originally stood up to do and reached inside her panties and nylons and tore away the tape holding her penis between her legs. It sprang free, semi-erect. She eased it into place along her lower belly and pulled her pantyhose and panties tight to hold it there. She pushed down on her diaphragm and her testes descended.
Tiffany looked down at Remy and saw that he was watching her intently.
She lowered her head bashfully. She realised what she had done and what she was.
“Do I disgust you? Is it awful?” a single tear ran down her cheek.
Remy reached out and pulled her into his lap, she was sitting sideways and he nuzzled her neck and whispered in her ear.
“On the contrary. You are fascinating. You are beautiful,” he lifted her chin and kissed her.
His hand went to her belly and stroked it, luxuriating in the feel of his fingers on her sheer pantyhose. His fingers continued their journey down to her pubis, slipping over her shiny satin panties. They found her fully erect and he slowly stroked her.
“Oh my god!” Tiffany groaned.
The feel of Remy's fingers gently caressing her through her panties was amazing; she had never felt anything so wonderful. She writhed and wriggled in Remy's lap as they kissed and caressed and then she became aware that his bathrobe was open and that his penis was pressing against her buttocks. It felt steely and powerful. It felt wonderful.
Tiffany turned in his lap so that she was straddling him. They were now face to face and were able to kiss with wantonness and abandon. Tiffany was a quick learner and she was soon exploring Remy's mouth with her tongue. Now there was no mistaking the fact that Remy was grinding his cock against her ass. She lifted herself a little and reached inside his shorts and freed his erection and then sat back down and began to rock back and forth.
For the trice that she had held the bare flesh of his phallus in her hand she had felt such a feeling of joy and wonder.
She was aware that Remy was leaking against her panties, she could feel the wetness of his precum as he ground himself against her. She too was wet, her penis pressing against his belly through her underwear. The feel of the nylon and satin sliding against his hard flesh was scintillating.
She kissed him again and he put his arms around her and held her close, grinding against her, kissing her forcefully, muffled whimpers of delight coming from his lips.
That was when she felt something else. Something that would remain with her for the rest of her life.
Power.
She realised that anyone who saw what they were doing would be disgusted that a man in his forties was seducing a teenage transgendered person. The reality was the tables had turned as soon as she straddled him. She might be a novice but she was in control. She could tease this man all night or get him off in a trice. Or she could be a bitch and just get up and leave him hot and unsatisfied.
But she had no intention of doing either.
She liked what they were doing and she intended to use Remy to teach her. To guide her.
She felt Remy's anxiousness to move on, to take their passion to new heights. He broke the kiss and eased her out of his lap. She furrowed her brow, confused and wondered if she was doing something wrong. What did he want?
Remy took off his briefs, never taking his eyes of the beautiful young girl standing before him dressed only in pantyhose, panties, blouse and heels. Her erection was bulging the front of her panties and he couldn’t help but reach out and squeeze it. He was rewarded with a gasp from those pretty red lips which he now intended to put to good use.
Remy opened his robe and opened his legs wider and nodded to the space between them.
A light went on in Tiffany’s head as she realised what he wanted.
She smiled seductively and got on her knees between his legs. She gazed at him, smiling wantonly as she took him in a firm grip and began to slowly stroke him. Remy threw back his head and groaned with pleasure. Tiffany took the opportunity to inspect his penis. It was long, sleek and veiny. The eye was leaking silvery threads of pre-ejaculate. It was not as big as hers but it looked slick and powerful. She wondered how it tasted.
Tiffany was technically a virgin but she’d seen enough porn to know that there were many ways to give a man fellatio and now was her opportunity to practise.
She lowered her mouth to his organ and tentatively lapped at it. Remy's precum was a little salty but otherwise tasteless. She lapped up every drop as it oozed from the eye of his glans. Then she ran her tongue along the girth of his penis listening to him whimper, hearing him beg her for release. She was in no hurry to give it to him.
When he put his hands on her head and tried to force her down she didn’t like it one bit. She shook her head and nipped at the tip of his penis. Remy got the message and removed his hands, content to let the pretty young girl between his legs take charge.
Tiffany teased Remy. She endlessly ran her tongue along the shaft of his penis, over his glans and across his scrotum listening to him cry and whimper with pleasure and frustration. The feel of her tongue, sometimes featherlight, sometimes coarsely lapping at his genitals was exquisite. The way she lapped at his glans and tickled his fraenulum, teasing him with little jagged darts of intense pleasure was incredible. This virgin was a quick learner.
Curiosity finally overcame her. Tiffany had always wondered what it would be like to take a cock in her mouth and she decided that now was the time to find out. She took all of him into her mouth and locked her lips around the base of his phallus and began to work her lips up and down his shaft, stopping at the glans to lick it and nip it gently.
“Oh my god!” Remy roared.
He instinctively put his hand back on her head and again she shook him off.
“Of sorry but that is so wonderful,” Remy gasped.
She stopped what she was doing and looked up at him from between his legs. Remy looked down at her gorgeous face, pale in the light from the TV, framed by the shock of black hair. Those blood-red lips. Those magnificent green eyes. When she grinned at him she almost seemed malevolent, she seemed to be sneering. Tiffany smiled at him wickedly and lowered her face to his cock.
Remy threw back his head and moaned as she earnestly worked on his penis. Tiffany slathered at it to get it lubricated and then worked her lips up and down the shaft, using her tongue on the bulbous head, swallowing the continuous flow of precum.
Remy was writhing in his seat and almost sobbing. He called her name over and over.
Tiffany sensed he was about to climax and she was as excited as he was. She reached into her underwear and took herself in hand. She worked her cock as she sucked and slathered Remy’s quivering phallus. They were both close.
Remy actually screamed when he climaxed. Tiffany felt his cock pulse and undulate in her mouth and then a torrent of hot salty semen filled her mouth. She swallowed the offering which triggered her own release. She orgasmed, muffling her groans on Remy's cock as the intensity of it washed over her. She slathered, sucked and lapped at Remy’s cock, milking him of every drop of his semen. She liked the taste of it.
The musky smell of ejaculate filled the air as her own issue splashed against the base of the couch and then spurted onto the cherrywood flooring. Tiffany wrung every drop of cum from her throbbing cock, the intensity of her orgasm magnified by the feelings of decadence and power as Remy came in her mouth.
She sucked him dry, swallowing every drop of him and then lifted her head and smiled up at him. Remy smiled back at her, a look of contentment and joyfulness on his face. He lifted her into his lap and they kissed passionately. He could feel that her panties were damp and guessed that she too had orgasmed. They kissed and caressed until Tiffany became tired. She extricated herself from his embrace and got to her feet.
“I’m tired and I’m going to bed,” she pouted like a petulant child.
Remy looked up at her, still fascinated and enraptured. He nodded at her, a look of utter content on his face.
She leaned down and picked up her skirt.
“Clean up my cum. Tomorrow you’re going to teach me how to fuck,” she said casually and then walked away, her heels clicking in the wooden floor.
Remy was astonished and perplexed.
Then he began to laugh.
All the next day Remy pestered Tiffany in the store. Whenever Bric-a-Brac was devoid of customers he pawed at her but she pushed him away. He even suggested closing the store over lunchtime so they could have sex.
“If we start doing anything different or suspicious people are going to notice,” Tiffany didn’t realise how fateful this statement would turn out to be until later.
“You tell me you are in an open marriage which is fine. But people and particularly my aunt and my mother are not going to be impressed that you are having sex with your sixteen-year-old niece are they?” Tiffany berated him.
Remy nodded wistfully. Tiffany was his Lolita and he was enraptured.
“And just think how much more you are going to enjoy me when you finally get me into bed tonight,” Tiffany smiled seductively.
Tiffany left the shop early to prepare herself and Remy could hardly contain himself. He kept glancing at his watch but the time seemed to pass immeasurably slow.
Tiffany locked the bathroom door behind her and took out her douche. She’s douched before but this was the first time she had to do so because she was going to have sex with a man. She got the unpleasantness out of the way, showered, brushed her teeth and used mouthwash.
She went back to her room and applied her makeup, very heavy and very sexy. She didn’t bother to tuck, she just stepped into a pair of red satin panties and then pulled on a pair of very sheer black hold-up stockings. She knew that Remy liked black stockings and tonight she was dressing for him. She didn’t bother with a bra either, she just put on a sheer black negligee, checked her makeup, brushed her hair, put on her jewellery and finally a pair of red high heel pumps. The red panties and heels contrasted nicely with the black stockings and negligee.
Tiffany doused herself in perfume and lay on the bed and waited excitedly, her cock hard in her panties in anticipation.
Remy closed and locked up the store right on closing time at 6pm. He quickly shaved, showered and brushed his teeth. He used mouthwash, deodorant and aftershave and almost pranced down the corridor to Tiffany’s room, his erection leading the way.
He burst through the door and Tiffany opened her arms invitingly and Remy fell on her. They kissed and fondled each other, rubbing cocks, grinding and groping. There was no tenderness; this was raw passion, this was lust.
They were both so turned on and eager that they were impatient.
“Let’s forego the fellatio Remy, I want you to fuck me,” Tiffany gasped.
Remy got off her and tried to roll her over.
“You can do me doggie any time you want to after this, but not now. This is my first time and I want to look at you, to see the expression on your face while you are fucking me,” Tiffany insisted.
She took off her panties and lay back down and put a pillow under the small of her back to raise her buttocks. She opened her arms and then her legs.
“Come fuck me lover. Take my cherry,” she whispered, her voice thick with lust.
Remy took the lubricant off the bedside table and slathered his cock with the slippery gel and squeezed a gobbet on Tiffany's sphincter. She looked up at him, his penis rampant and glistening. He looked down at her and was so aroused, she lay there with that black hair, that dark eye makeup, luscious red lips, long stocking-sheathed legs wide open in anticipation.
Remy slipped a finger inside Tiffany’s anus and worked the lube deep inside her, being her first time he did not want to cause her any discomfort.
“Come on,” Tiffany said impatiently, grabbing his cock and pulling him towards her.
“Ready?” Remy's cock trembled near her puckered sphincter.
Tiffany nodded.
Remy positioned his rock-hard penis at the entrance to Tiffany’s anus and then ever so slowly pierced her sphincter.
Tiffany gasped and grimaced. It hurt, as she expected it would. She knew from what the research she had done online that if she could tolerate the pain until Remy was fully inside her, her anus would become dilated and she would start to feel pleasure.
Remy had his glans inside Tiffany’s sphincter but was reluctant to thrust any deeper because he believed he was causing her pain.
“Come on Remy, fuck me!” she goaded him.
She wrapped her legs around him and thrust upwards, ever so slowly skewering herself on his cock. She grimaced and gasped the whole time but she was already starting to feel ripples of pleasure from her sphincter and the feeling of being full of cock was incredible
Tiffany put her arms around Remy's neck and pulled his face to hers.
“Nice. Lovely,” she whispered and kissed him deeply.
Remy began to deliberately fuck Tiffany using long leisurely thrusts. Tiffany whimpered underneath him, feelings of intense pleasure radiated from her sphincter and when Remy drove deep inside her his cock pressed on her prostate gland which emitted waves of pure gratification.
Remy kissed her hard and she responded, raking her nails on his back and shoulders and squeezing him with her thighs. Her tight anus clung to Remy's cock, contracting it as he fucked her. He was close to coming but he wanted to wait for Tiffany. The feel of her stocking-clad thighs against his sensitive skin was delightful.
Tiffany encouraged Remy to fuck her harder, her excitement was intensifying and she could feel an orgasm building deep inside her. The feel of Remy's cock buried deep in her anus combined with her cock rubbing on his stomach was going to tip her over the edge.
“Fuck me Remy! Take me! Make me come!” she gasped.
“Oh Tiff! I’m coming,” Remy hissed.
He held her down on the bed and jackhammered his cock in and out of tight anus. Tiffany squealed as she came. The most intense orgasm of her life surged through her body. Her cock convulsed, spewing scalding semen whilst concurrently her anus throbbed, her sphincter spasmed and her prostate throbbed. She beat her fists against Remy's chest and drummed her heels on his back.
Remy pushed his cock all the way inside Tiffany and ejaculated, her tight anus expressing every scintilla of semen from his quivering cock.
He held her down on the bed as she thrashed writhed beneath him until she was sated.
Tiffany was finally spent and exhausted, she lat still as Remy kissed her softly, his cock still inside her slowly contracting, she felt his spend dribbling out of her anus. She returned his kisses and stroked his cheek lovingly, keeping her legs wrapped around him to hold him close.
“That was wonderful,” she kissed him tenderly.
“It was amazing,” Remy grinned down at her.
He could feel her semen, sticky between their bellies.
“Can we do it again later,” Tiffany said coyly.
“Of course when can. As soon as I recover,” Remy grinned.
“I’ll let you do it to me every day if you are nice to me,” Tiffany teased.
And so it came to be that Remy and Tiffany entered into a fiery love affair that lasted nearly three weeks. She was a good student when it came to both cards and sex. She was soon beating him occasionally at cards and teaching him new sexual techniques as she became more adept and self aware.
They were both insatiable, during the day Remy would lock the door to the shop and pull the blinds and bend her over the counter and fuck her. They would spend all night in her bed making love. She learned how to control her sphincter muscles and would sit astride him, impaled on his cock, not moving; edging him until he begged for her to grant him release.
When Shelley came back from her road trip Remy and Tiffany found they couldn’t stop. Remy was infatuated with Tiffany. She was his teenage dream-girl. Tiffany liked Remy but not in the same way. To her sex with him was just a side benefit of living with her aunt and uncle, he was an attentive lover and doted on her.
Shelley soon became suspicious of them; the way they acted around each other, their furtive glances and gestures. One morning she told Remy that she had a doctor’s appointment and would be gone for three hours. He offered to drive her but she said it was fine, it was just a routine test for a woman her age.
Shelley snuck back home an hour after she left and found the store locked and shuttered. She unlocked the door to Bric-a-Brac and found her life partner with his cock buried up to the hilt in her niece’s behind.
After the tantrums, recriminations, allegations, and counter-allegations, Shelley accepted Remy's side of the story. Remy had been duped and seduced by the little vixen transsexual. Tiffany was to blame. She was a Lolita.
The fact that Remy was forty years old and Tiffany was only sixteen seemed to be lost on Shelley.
Shelley kicked Tiffany out of the house, exactly as Tiffany’s father had done.
This time Tiffany was better prepared. She had some life skills that she didn’t have the last time she was kicked to the curb and she had a little money she had made working in the store.
Tiffany tossed a coin, heads LA, tails New York. It came up heads.
She took a bus to Los Angeles instead of an airplane because it was cheaper and she was in no rush to get there.
Raffe Ignesman spotted Tiffany Robinson as soon as she alighted from the bus. Most of the passengers had travelled in tracksuits, jeans or some other kind of comfortable clothing. Tiffany had changed her clothes at the last stop because she wanted to arrive in LA looking and feeling good. She was wearing a short denim skirt and matching jacket under which she wore a red satin blouse. She was wearing full makeup, nylons and red high heels.
Tiffany looked around with awe at the busy bus station which was noisy and dirty. She didn’t care. She was in the big-smoke now and as far as she was concerned the world was her oyster.
Raffe was delighted with the spectacular young creature standing next to the bus looking lost and alone. She was undoubtedly pretty. She was downright gorgeous in fact; and young, and sexy, and obviously bewildered. As he got closer to her he guessed that she was trans. Even though she was very feminine there were tells that guys in Raffe's line of work knew by heart. She would still be a wonderful addition to his stable.
Tiffany had two suitcases which was going to be awkward for her. She took them both in hand and turned around and ran smack into Raffe.
“I’m sorry doll. Here, let me help you with those,” Raffe gave her his best smile.
Although he was young and handsome Tiffany thought he smiled like a wolf. He was rake thin and wore an expensive suit and shoes. She guessed that the Philippe Patek on his wrist was worth at least two grand. Tiffany immediately figured out what Raffe was up to, but she did not let on that she knew.
“Can I give you a lift somewhere?” Raffe opened his hands as if to indicate that he was harmless; which was the opposite of what he was.
“I’m going to the Central Hotel and Boarding House, downtown,” Tiffany replied.
“I can do that,” Raffe smiled again.
“I’m Raffe Ignesman by the way,” he offered his hand.
“I’m Tiffany Robinson or Tiff if you like,” she shook his hand.
The Central Hotel and Boarding House was a cheap flophouse used by waifs and wanderers when they first came to LA and Raffe had picked up more than his fair share of prospects for his stable from there.
Raffe drove a white Chrysler LeBaron just like in the song. He wheeled one suitcase and she the other. Tiffany was also loaded down with a travel bag and a handbag. Raffe hefted her suitcases and travel bag into the trunk and she took her handbag into the front seat with her.
As they exited the parking lot Raffe began a rehearsed speech.
“What you in town for sweet-pea? How long you staying?” he glanced at her.
Traffic was busy so the ride was going to take a while, which suited him.
“I’ve been thrown out of home so I’ve come to LA to try to find a job and hopefully a future,” Tiffany gave him an innocent smile.
“Wow! Too bad. And you are so young too,” Raffe sympathised with her.
“Doesn’t help that I’m transgender and haven’t yet started hormones or had any surgery. And I’m only sixteen, so you know…” her voice trailed off.
Tiffany was playing Raffe just as he was playing her.
“That is so sad honey. I just wish there was something I could do to help,” the sharklike grin returned to his face.
“Well there is Raffe,” Tiffany had allowed her skirt to creep up her thighs and Raffe’s eyes wandered to her legs, then to the road then back to her legs.
“I’m so glad that you are going to let me help,” Raffe did his best to sound sincere.
“What is it I can do?” he asked the fifty-four thousand dollar question.
“Well when I start working for you as a prostitute I don’t want to work on the streets. I don’t want you to be violent with me. I don’t want to get hooked on drugs, and I want a fair share of what I make for you,” Tiffany said straightforwardly.
Raffe almost left the road he was so shocked.
“What did you think? You were going to woo me, seduce me, promise me the world and then throw me out on the street working for you as a hooker?” Tiffany said casually.
“How old are you really?” Raffe frowned.
The pleasantness had gone from his voice.
“I’m sixteen going on seventeen but I’m learned a lot the last few months. It’s hardened me. I’ve been used and I’ve been discarded and I’m not going to let that happen again,” she too spoke plainly.
“You any good?” Raffe nodded at her crotch.
“My uncle seems to think so,” Tiffany quipped.
“Jesus! Your uncle?” Raffe swerved the car again in reaction to her answer.
“Look. Let’s cut the bullshit. Take me back to your place or a hotel, somewhere decent, and let me show you what I can do,” Tiffany smiled at him and placed a hand on his shoulder.
“Jesus,” Raffe sighed.
“Ok little girl. Let’s go to my place and try you out,” Raffe smiled as he stared at the road through the windshield; he liked ‘em young.
“We won’t unpack. If you ain't as good as you say you are you can find your own way to your hotel. If you are as good as you say are I might even spring a room for you here. Of course it goes on the tab,” Raffe offered her his wolfish grin again.
They had driven into the underground parking garage of a swank apartment building.
Raffe led her to the elevator and waved his passkey to take it to the penthouse floor. Tiffany didn’t get to see much of his apartment because he led her straight to his bedroom. He put down a towel and pushed her down on his massive bed.
“We’ll take the foreplay as wrote, you can begin by sucking my dick,” Raffe chuckled, stripping out of his clothes.
Tiffany opened her mouth and took Raffe’s long thin cock into her mouth and went to work. She applied all of the oral skills that Remy had taught her and some she had invented herself. She fellated Raffe slowly at first, building up speed until she was sucking his cock with gusto. When he was close to coming he pushed her off him.
“Not bad sugar, now let’s get you undressed and see what else you’ve got offer,” he helped her out of her jacket and unbuttoned her blouse and she took it off.
He unhooked her bra.
“You really need some tits honey,” he inspected her flawless white skin like she was a farm animal for sale.
Tiffany lay back and Raffe pulled down her skirt and threw it in on the floor.
“I’ll say one thing, you got a great ass and those legs just go on forever,” he stroked her thighs and worked his hands down as far as her ankles and then opened her legs.
He removed her panties and freed her cock.
“Wow that’s big! A lot of guys like trannies with big dicks, that’s another asset,” he said as he stroked Tiffany to full tumescence.
He took a tube of lubricant from the top drawer of the bedside table.
“I’m not really prepared,” Tiffany said sheepishly.
“Oh come on now. I’m not gonna let that stop me,” Raffe viciously ripped out the crotch of her pantyhose.
He plunged his cock into her tight anus and Tiffany smiled up at him despite the pain. She gripped his hips and began to fuck him. He rolled her over and pulled her to her knees and continued. She squirmed for him and used her anal muscles to squeeze his cock as he fucked her.
“Jesus you are good,” Raffe grunted.
“Play with yourself sugar, I wanna see that thing spurt,” Raffe said as he gripped her thighs and began to plough her.
She willingly obliged. This was the first time she had been used roughly and she found that she quite liked it.
Tiffany orgasmed with him when Raffe pulled her back hard against him and ejaculated deep inside her.
Once he had finished he released her and pulled his cock from Tiffany’s dripping anus and wiped it on her ass. Tiffany fell forward on the bed, sore but satisfied. Raffe came back from the ensuite bathroom with a wet cloth and had her clean herself. He made her strip naked and parade in front of him.
“The good news is I can use you. You’re young, sweet and know how to fuck. I’d say that blowjob was as good as any I’ve ever had,” Raffe said sitting on the edge of the bed, now dressed in a silk robe.
“The bad news is, is that even though you are exceptionally beautiful and have a great ass and legs; you need some feminine curves and tits,” he continued to prod and poke at her.
“I have my own doctor who looks after my girls. I’ll get him to start you on hormones and get you booked into a hospital he uses down in Mexico to get you a nice big set of titties,” he walked over to the wet bar and poured them both a drink.
He threw her a robe similar to his and beckoned her to come sit with him in the lounge.
“Put your panties on sweet-cheeks, this lounge is white leather and I don’t want it stained,” Raffe sniggered.
He handed her a drink and lit a cigarette. He offered her one and she took it.
“I’m not gonna put you on the streets, you are way too valuable an asset for me to do that. You are going into my stable as a callgirl for my well-paying clientele,” Raffe spoke to her like she was his chattel.
“What’s the deal?” Tiffany asked sipping her drink.
“Fifty-fifty straight up. But you pay me for the hormones and the tits, plus you pay rent, ok?” he said.
“You will be a specialty. There’s guys out there who will pay big bucks for a night with a special girl like you with your talents,” Raffe explained.
“Sounds too good to be true,” Tiffany pulled up her legs up and folded her arms around them.
“It is. I don’t usually give my girls deals like this. But you are special and we can both make a lot of money. I have interests in other businesses,” Raffe gave her his wolf-grin again.
“Can I think about it?” Tiffany said wistfully.
“Yeah. You can. You have until the door hits you in the ass to make up your mind,” Raffe got up to indicate the meeting was adjourned.
“I’m in,” Tiffany said with determination.
“Ok then, lets seal it with a kiss. I haven’t tried your kissing skills yet,” Raffe pulled her up off the lounge and kissed her.
He kissed her long and hard and then started to ease her back towards the bedroom, still kissing her.
“Let’s fuck a little more and then we can sort out the finer points of our deal,” Raffe said through crushed lips.
The next twenty years of Tiffany’s life was ordained that very day.
Raffe settled her into an apartment and had his doctor come see her. The doctor gave her a complete physical and provided her with female hormones and gave her instructions on how to use them. Tiffany and Raffe argued about the size of the breasts she was about to receive. Raffe wanted 40-DDs so she would have huge tits on her lean frame but Tiffany argued against it. Her selling point would be that she was young and girly; putting huge tits on her would spoil that. They compromised on 38-Cs and Tiffany had the surgery.
Raffe gave her a week to recover and put her to work.
Tiffany was hugely popular and was constantly in demand. She soon developed a string of clientele who repeatedly demanded her services. Some offered to take her away from her life as a prostitute, they fell in love with her. Tiffany knew that they were fantasising about a life that could never be, but she milked her clients for whatever she could get from them.
Raffe finally admitted to Tiffany that he really wanted her to get the huge DDs so he could put her into porn. Tiffany argued that a sweet young thing with a huge cock like hers would be very popular anyway.
They met with a man named Lyle Brinkman, who used the pseudonym Devon Devine, owner of Xavier Productions. Xavier Productions was a pornography business producing magazines and DVDs and was venturing into online video streaming sales.
Raffe negotiated a good deal for her. She would be paid four thousand dollars per movie, five thousand for the stuff involving bondage and discipline, degradation and pissing, which was becoming more popular. She churned out an average of one movie per week and she never turned down a role. She worked in ‘man fucks tranny’ movies, ‘tranny fucks woman’ movies, and ‘tranny fucks tranny’ movies and tolerated doing the more degrading stuff for the extra cash. She wouldn’t fuck men though, she just couldn’t do it.
She gave Raffe fifty precent of everything she earned and she eventually trusted Raffe enough to let him invest her money. Although he was her pimp they became more like partners and occasional lovers. He invested her money wisely and bought a condo for her in Lake Tahoe which she rented out to cover the corporate-body fess. The condo was almost paying for itself.
Tiffany still had her fascination with cards and practiced her moves every chance she got. On the rare occasions that she took vacations she went to Las Vegas or Reno and practiced counting cards and carefully watched the dealers and the pit bosses. Raffe pulled a few strings and she got her gaming licence. She was surprised when a casino offered her a short stint as a dealer.
It was a small casino and it was cashing in on her celebrity by advertising that they had a famous porn dealing on the tables. Tiffany loved the thrill of working in the casino but it didn’t pay her enough. It was merely a diversion a few times a year.
As Tiffany got older she began to work less. She was still stunning but she was no longer as popular on Raffe’s online dating site as the younger girls. It didn’t matter, she had a steady income from her regular customers, all wealthy men. She sometimes, but rarely, took on a high-roller in a casino on as client but only if she liked him. This was a bonus to her as far as she was concerned and she didn’t split the fee with Raffe.
The porn business was slowing down too. Lyle wanted younger actresses, the younger the better, for his movies and Raffe was supplying them. Young girls that he conned or bullied into a life of prostitution and pornography.
What Tiffany didn’t know was that Raffe was selling some of the girls on the dark web. The dark web is a secret part of the Internet that has a few special websites that can only be accessed through certain gateways by certain people who know how to get there. It’s a place where you can buy anything from drugs, to weapons, to stolen goods and even people. Wealthy Russian, Indian, and Arab men in particular liked young, light-skinned, American girls.
Tiffany had been in a few movies with Tina, Lyle’s common-law wife, who was also a transsexual woman. They clicked both on and off screen. They had a torrid love affair which eventually tapered off to become friendship, although they still liked a roll in the hay together when the mood took them. Tina was Tiffany’s only close friend other than Raffe.
Tiffany had grown up hard. Selling her body had toughened her and she saw the worst and sometimes the best in people. She didn’t feel sorry for herself, she was pragmatic. This was the life she had chosen. By then she had a decent nut in the bank she could have got out at any time, but the truth was she loved her life.
Then it all came crashing down. Raffe was selling two young girls to two Russian gangsters but one of the girls was the step-daughter of the wealthy construction mogul, Steve Patterson, who had hired a guy named Randy Carter to rescue her. Randy enlisted the help of his sister-in-law, Sarah Carter. At the handover to the Russians there was gunplay. No one got killed but Sarah Carter got wounded. The girls got free and Raffe had to go into hiding.
The Russian mob found him and executed him. This meant Tiffany was out on her own, but by now she had the skills to look after herself.
Although Lyle and Tina Brinkman were not intimately associated with Raffe Ignesman’s business of selling girls online, they were guilty by association, possible accomplices. Both the Russians and the FBI were looking for them.
Lyle and Tina disappeared, some said to Mexico, some said to Europe. They did manage to transfer all of the money out of their business and private accounts, so wherever they were, they were living the highlife.
So all those years later when Stephen Bateman said to Tiffany in that Lake Tahoe hotel where they had just made love:
“I actually have a business proposition for you.”
“Have you ever heard of Lyle and Tina Brinkman?”
You can fully understand why Tiffany paled with shock and was speechless.
To be continued.
Author's note: As well as the thumbs up thingy, I'd appreciate some comments please.
“Is that the real reason I’m here!” Tiffany’s mood shifted from bliss to outrage at the mention of Lyle and Tina Brinkman.
“What do they want? I’m not even sure that they didn’t set up Raffe and make up that bullshit about him peddling girls online,” Tiffany struggled to get up out of Stephen’s lap.
“Settle down Tiffany. Listen to me. Listen to me,” Stephen let go of her and helped her to her feet.
He tried to take her in his arms but Tiffany pushed him away.
“I need a drink,” Tiffany said furiously.
“It’s ten in the morning,” Stephen said.
Tiffany glared at him and he knew better than to argue. He went over to the bar to pour her a drink.
“And a cigarette,” she snapped at him.
“This is a non-smoking hotel and…” Stephen started to say and then he saw the fury reflected in those green eyes.
“Top drawer of the sideboard,” he nodded over towards the flower arrangement.
Tiffany snatched the cigarettes from the drawer and lit one, her hand shaking. She blew smoke at the ceiling and glared at Stephen. She snatched the drink out of his hand and took a sip. Stephen went back to the bar and fixed his own drink and came back to where Tiffany was standing in the middle of the room.
He indicated a chair and Tiffany dropped into it. She crushed out her cigarette in an antique crystal dish and reached for another.
“They’re going to fine me and make me pay for the room to be deodorised and for that dish,” Stephen began but when he saw the rage reflected in Tiffany's eyes he shut up.
“Ah fuck it. Give me one of those,” he snatched the cigarettes off the side-table and lit up.
“The dish is a knock off. If they charge you more than a hundred for it they’re ripping you off,” Tiffany hissed.
Stephen looked at her quizzically.
“I started work in an antique business when I first left home. It’s a short story with no happy ending, except for my cunt uncle who got plenty of happy endings out of me,” Tiffany stared down into her glass but Stephen knew better than to pursue this interesting segue.
“Ok the truth,” Stephen began.
“I did initially pay for your services so that I could put a business proposal to you. I also did ask around about you, I had to get two references to log into your website after all.”
“Everything I told you last night is true. I do admire and respect you and I love being in your company,” Stephen tried to take her hand but she snatched it away.
“You don’t know anything about me,” Tiffany finished her drink and waggled the glass at him.
Stephen continued to talk while he made her another drink.
“You’d be surprised what I know Tiffany. I know you were kicked out of home by your mother and father and then by your aunt and uncle. It must have been terrifying being a transsexual girl only just beginning her transformation, abandoned, then arriving in LA not knowing anyone.”
“But you made a success of your life. You overcame all the obstacles. Yes your lifestyle would appear, shall we say, unorthodox to some, but you are a success, there is no doubting that,” Stephen raised his glass to her in a mock toast.
“What is this? This is your life?” Tiffany said sarcastically.
“You don’t know anything about me,” Tiffany snapped.
“I know enough though. I know that you are one of the best card dealers around and that you have on occasion, determined the outcome of a game,” Stephen studied the end of his cigarette.
Tiffany took a deep breath. They were sailing into deeper water now. Was this a sting? Was she about to be arrested? Unlikely, most investigators don’t fuck their suspects.
“Ok. Enough bullshit. What do you want?” Tiffany arose and took Stephen's glass from him and refilled both their drinks.
“First Lyle and Tina did not set up Raffe Ignesman. Why kill the golden goose? Raffe was finding them young girls to appear in their porn.”
“Second off. It’s possible that you didn’t know what Raffe was selling on the dark web, but you are so quick and intelligent that I bet you at least suspected,” Stephen took a sip of his drink.
“Do you know that when he first took you in, he put you up for auction for offers of over two hundred thousand dollars. Right after you recovered from your reconstructive surgery,” Stephen waited for a reaction.
“That makes good business sense. It would have been an excellent return on his investment,” Tiffany said frankly.
Inside she was seething. Raffe was willing to sell her into sexual slavery for a few bucks.
“Anyway, let’s get back on track. Lyle and Tina had to go overseas into hiding but they are back now. They were able to convince the Russian mob that they had nothing to do with the Sarah Carter incident which resulted in the FBI investigation into human trafficking,” Stephen continued.
“Sarah lives in Waikiki by the way, with her husband Randy Carter and to this day denies that she was at the house where the exchange was to take place. She claims that she received the gunshot wound when someone tried to snatch her bag in the Dodger Stadium parking lot.”
“Lyle and Tina cooperated with the FBI and brokered a deal. They admitted that they procured girls from Raffe and that they abetted the brokerage of young girls, albeit unknowingly. They just assisted. Tina hosted special parties hosted by Raffe at his safehouse. They didn’t know it was a trafficking venue, they claim they thought it was just prostitution,” Stephen made an sympathetic gesture.
“Bullshit they didn’t know!” Tiffany growled.
“Maybe. Maybe not, but some people could say the same about you,” Stephen smiled.
Tiffany squirmed in her seat. This was an accusation that she could never disprove. She had been interviewed by the FBI when Raffe disappeared and it was obvious they didn’t believe that she didn’t know about that side of Raffe’s business.
“Get to the point,” Tiffany wanted another drink but knew better than to have one.
“Lyle and Tina Brinkman had to pay off the Russians and they paid a hefty fine to the FBI but they are now free and clear. But…” Stephen looked at Tiffany expectantly.
“But their porn business is gone and they’re broke,” Tiffany finished his sentence.
“Not quite broke,” Stephen smiled conspiratorially.
“They have a nest egg. Not much. Two million and change. And they have an idea how to grow it,” his smile widened.
“What is it you do exactly Stephen? You list your occupation as ‘other’ on your profile, which I usually find interesting, but in this case I think I’m going to regret it,” she reached for another cigarette.
“I’m a broker, I bring people together,” Stephen flashed the smile at her.
“So what are we going to do; play Ocean’s Eleven?” Tiffany said sarcastically.
“Not quite, but close. I’d like to set up a meeting with you and Lyle and Tina Brinkman. I’ll mediate. It’s a business proposition. One where you are likely to make a lot of money,” Stephen crossed one leg over the other.
“How much?” Tiffany glared at him.
“A lot. Nearly a million,” Stephen opened his hands to emphasise his point.
“When and where?” Tiffany finished her drink and crushed out her cigarette.
She was ready to leave.
“Why not here, as we previously arranged,” Stephen smiled magnanimously.
“Sure. But now you have to pay for my time,” Tiffany replied spitefully.
“Of course Tiff. I’d pay for you regardless,” he walked with her to the door.
“I meant what I said last night. I’ve known you only a few hours and I already feel a deep affection for you,” Stephen leaned in and softly kissed her lips.
He opened the door and Tiffany began to leave. She stopped and looked over her shoulder at him.
“There’s something you should know,” she said.
Stephen shrugged his shoulders.
“I’ve fucked both of them,” Tiffany said and then turned away and walked down the corridor.
“You forgot your tip,” Stephen called after her.
“I’ll put it on your tab,” Tiffany called back.
“I have a tab? Does that mean I’m going to be seeing you again?” Stephen chirped.
Tiffany just smiled to herself and pressed the button for the elevator.
Tiffany deliberately arrived late for the meeting. She didn’t want to appear too eager to take up their offer, whatever it was. As promised, Stephen Bently had deposited two thousand dollars into her business account to pay for her services.
She had gone for the power look when she dressed for the meeting. A tight-fitting navy-blue suit with short skirt, a white satin blouse, flesh-toned pantyhose and black high heels. Her makeup featured smoky eyes, bright red lipstick and a little rouge on her alabaster skin to highlight her cheekbones.
Stephen came down in the elevator to greet her and she was surprised, or rather disappointed, that he didn’t make a move on her on the way up.
“Don’t you like what you see?” Tiffany playfully pouted at him.
“I love what I see. I’m trying hard to hide an erection in case you didn’t notice. But I don’t mix business and pleasure,” Stephen said pragmatically.
“But I’m going to fuck you senseless after the meeting,” his face broke into a grin.
“Who says I’m staying?” Tiffany liked to banter.
Stephen pressed her against the wall of the elevator, his face only an inch from hers. His hands squeezed her thighs.
“When I pay for something I expect to get it,” he was breathing heavy.
Tiffany grinned at his childish attempt at bravado.
She kissed the tip of his nose.
“We’ll see mister Bateman,” she smirked.
Stephen smiled back at her.
“I really do like you, you know,” Stephen held her at arms length and studied her face.
Tiffany blushed. It was rare that she ever became embarrassed.
Tina had to be in her fifties but she was still stunning. She was wearing a green satin Cheongsam with a Mandarin collar; the hem rested at the top of her thighs showing off her long elegant legs sheathed in sleek flesh-toned hosiery. Her waist had thickened a little and her bosom had obviously had some work done to it, as had her face.
It was elfin; heart-shaped, with blue eyes, tiny nose and cupid’s-bow lips. Her jet black hair was worn shoulder-length, emphasising her long elegant neck and alabaster skin. Her makeup was perfectly applied with dark smoky eyes and red lipstick.
She broke into a genuine smile when Tiffany entered the room. Tina could be mistaken for Tiffany’s older sister because they looked so much alike. Lyle had taken advantage of their resemblance when making his porn. He promoted their movies as mother-daughter or sister-sister tranny incest. Two trannies who had an uncanny resemblance was bound to tickle the fancy of those who had eclectic tastes in pornography.
Lyle too had aged gracefully. His hair was still thick and had retained its colour; Tiffany guessed it was an expensive weave. He was trim and good looking. Her mind couldn’t help but flick back to him fucking her bent over the executive desk in his office.
Not that she was special, Lyle fucked all the girls who worked for him. He saw it as his duty to sample the wares before he put them in his pictures.
Tina stepped forward and took Tiffany’s hand and kissed her check.
“Tiffany darling; it’s been so long,” she gave her that smile.
The smile that had melted a thousand hearts.
Tiffany had liked working with Tina. When they had sex on set they didn’t have to fake enjoying each other.
“Hello Tina. How was Juarez? Or was it Tijuana? Or some nice resort on the coast maybe?” Tiffany goaded her.
“Really Tiff? Are we going to play that game?” Tina gave her the killer smile.
“Hi Tiff,” Lyle stepped forward and hugged her and kissed her cheek, she felt him subtly squeeze her backside.
He couldn’t help himself, Lyle was still a sleaze.
“Let’s talk about the elephant in room shall we before we try to do business,” Lyle said.
“Tina and I had nothing to do with what happened to Raffe, other than that we used the girls he procured for me in my movies and Tina hosted parties at his house,” Lyle opened his hands expressing his innocence.
“I thought the parties were just an extension of Raffe’s prostitution ring but for high-rollers. Rich guys would come to the parties, take the young girls to the bedroom and try them out and if they liked what they sampled they took them home,” Tina explained it like it was just a business transaction.
Tiffany believed them both not one little bit but it would change nothing. Raffe was gone and she was broke and still selling her ass to make ends meet.
Stephen got everyone settled and made them all drinks.
“So what’s the deal?” Tiffany got straight to the point.
Lyle nodded at Stephen who began.
“Lyle and Tina approached me with an idea which at first I thought was ludicrous but having mulled it over for a while I think it will work,” he began.
“As you know there are several high stakes poker tournaments going around but we’ve decided to host our own.”
“It will be exclusive and require each prospective player to buy in for one million dollars. Six players equals six million dollars. One million of that comes from our stooge so we kick in another four, making the pot ten million dollars,” Stephen sipped his drink.
“That’s a lot of money for a game of cards,” Tiffany was interested.
“Yes and here’s the kicker. It’s a knockout tournament. We whittle them down. As the players lose they drop out of the tournament so the last two players play for everything,” Stephen had a satisfied grin on his face.
“And let me guess. We rig it so that one of the two final players is our stooge and because we own the dealer he wins,” Tiffany finished the tale for him.
“Yes Tiff. You’re the dealer and I bet you’ve worked with someone before who knows how to do this sort of thing who can be our stooge,” Lyle interrupted.
“But that someone would need to be able to ante up one million in cash,” Tina said.
“I probably know someone who can do that,” Tiffany mused.
“We make a spectacle of it. We hold the tournament here, at the Grand Lake Hotel and Casino. It’s small but it’s classy. We put the money on display, I’m having a safe built out of perspex so the players and gawkers can drool over the cash during the tournament. It’s cheesy but players like that sort of shit,” Stephen grinned.
“What’s the rake?” Lyle asked.
The rake is the percentage of the pot that goes to the house.
“Five percent, so half a million,” Stephen replied.
“Seems fair,” Lyle nodded.
“So all I need to do is kick in a million dollars cash and rig the game without being caught,” Tiffany said.
“Can you get a million?” Lyle raised a brow quizzically.
“Everybody in this room has done their research. I’m asset rich but cash poor but I know where I can get my hands on the money,” Tiffany studied her fingernails.
“A loan? Tiff, if you’re going to do that let me lend you the money,” Stephen interjected.
“No Stephen. I don’t borrow money from clients. I have some dignity,” Tiffany replied.
“I never meant…” Stephen was interrupted by Lyle.
“So does that mean you’re in? You can get the cash and find us a player?” Lyle’s eyes were burning with greed.
“Can you find the other patsies?” Tiffany countered.
“Got them lined up already,” Lyle grinned.
“Ok. Let’s do it. I’ll have my guy here tomorrow. Let’s meet here at the same time,” Tiffany was all business.
Tiffany excused herself to make a phone call while Stephen made small talk with Lyle and Tina and eventually showed them out.
Tiffany was on the phone to Kurt Bentley when Stephen snuck up behind her and put his arms around her, nuzzling her neck.
“See you tomorrow,” she said to Kurt and tossed her phone on the nightstand.
“I can tell by the feel of that thing digging in me in the butt that you are ready to take your money’s worth,” Tiffany twisted in Stephen’s arms so that she was facing him.
“Why do you have to say things like that? Like you are some chattel for sale?” she could see the disappointment in Stephen’s eyes.
“Because I am. I always have been. You can put lipstick on a pig but it’s still a pig,” Tiffany sighed.
“Jesus Tiff I hate it when you talk like that,” Stephen dropped his head.
“I’ve told you Stephen. You think you know me but you don’t really. What do you think this is? Are you playing some other movie in your head now? Am I Julia Roberts and you’re Richard Gere in Pretty Woman?” Tiffany said.
She lifted Stephen’s chin.
“I really like you Stephen. I mean I really like you a lot, but let’s just let things run their natural course ok?” she smiled and Stephen couldn’t help but smile back at her.
“Now why don’t we take advantage on the big bed right there,” she grinned.
Stephen kissed her and backed her up to bed and when she fell onto it he fell on top of her.
He kissed her, pushing her down on the bed with his body. Her skirt had ridden up and her blouse had become untucked.
“Let me get undressed,” Tiffany gasped when Stephen finally stopped kissing her.
“Uh-uh. I want to fuck you fully clothed in that power suit,” Stephen’s throat was thick with lust.
Stephen became a little rough with her but Tiffany enjoyed it. He’d been very affectionate with her up to now and it was good to see him show a little tenacity.
He dragged Tiffany to her feet and bent her over. Her knees rested against the edge of the big bed and she supported her weight with her hands spread on the mattress. Stephen kicked her heels apart and she heard him unzip.
He yanked down her panties and pantyhose and tore away her gaff. Tiffany was aroused and Stephen squeezed her penis.
“You like it a little rough don’t you Tiff,” he wheezed in her ear.
She nodded and felt him probing in the crevice of her buttocks.
“Oh my god!” Tiffany gasped as Stephen thrust himself all the way inside her.
“Push back! Push back like you want it!” Stephen growled.
Tiffany pushed back against him and wriggled her buttocks. His cock filled her anus, his glans pressing on her prostate, her own cock was leaking rivulets of precum.
“Beg me to fuck you!” Stephen gripped her shoulders and pressed her body against his.
“Fuck me please Stephen, please fuck me,” she gasped.
Stephen placed his hands on her hips and began to brutally fuck her, burying his cock deep inside her and then pulling out nearly all the way and then thrusting himself back inside her.
Tiffany moaned with pleasure as Stephen violated her. He was holding her hips so tight that it hurt, but it hurt in good way. His cock was ravaging her anus but the pleasure was phenomenal. Stephen’s thick cock stimulated the nerves in her sphincter while his bulbous glans pushed on her prostate causing Tiffany to cry out with lust.
Tiffany came.
Without touching herself she ejaculated, spattering her warm seed onto the satin comforter.
“Oh god yesss!” she moaned like a harlot as Stephen held her tight and ejaculated inside her.
She pushed back against him and ground her buttocks, draining him of his issue. His hot cum filled her anus, some of it dribbled down her leg and soaked into her pantyhose.
Stephen collapsed on top of her, pinning Tiffany to the bed, his cock still buried in her ass. Her legs were tangled in her pantyhose and with Stephen on top of her she was pinned face-down and finding it difficult to breath.
Stephen suddenly realised what he was doing and climbed off her and cradled her in his arms.
“I’m so sorry. I hope I didn’t hurt you,” Stephen looked lovingly into her eyes.
“Sorry for what? That’s just the fucking I needed thank you very much,” she patted his face.
“Now let me get undressed so we can get a little loving going on and you can do me again, but slowly,” she smiled at him.
She saw him sulk.
“Ok I’ll leave on my nylons and heels, I know you like that,” she grinned at him.
While Stephen and Tiffany spent the night making love Kurt Bentley was on a chartered plane flying in from LA. He arrived late but there was a room waiting for him at the Grand Lake Hotel. He crashed and slept til late in the day. He contacted Tiffany who confirmed that the meet was still on.
So at the next meeting the five conspirators: Lyle and Tina Brinkman, Kurt Bentley, Stephen Bateman, and Tiffany Robinson all met together in Stephen’s hotel room.
Tiffany had been home and changed and collected the one million dollars cash she needed from her anonymous donor. She refused to tell Stephen where she got the money when he pressed her. Kurt had bought his million in an attache case. Lyle and Tina put their two million on the table and Stephen put in the remaining one million to bring the total to five million dollars.
“That’s a fucking lot of cash!” Kurt whistled.
“And our patsies are going to ante up five million between them which we split equally when they lose. We all chip in for the rake so we make nearly a million each in cash,” Lyle grinned.
“So you and Tina are happy with a million dollars each?” Kurt was sceptical.
“Look. We put up two million and make back another two mil, that’s one hundred precent profit. Where else do I get that return on investment except for selling drugs,” Lyle replied.
“Selling people,” Tiffany couldn’t help herself.
“Tiff! Really!” Tina admonished her.
“Sorry, sorry. Dumb thing to say,” Tiffany apologised.
Introductions had already been made and Tiffany could see that Kurt was taken with Tina. If Lyle wasn’t here she bet Kurt would make a move on her.
Tonight Tina was wearing a plain blue dress that hugged her curves, sheer tan nylons and black heels. Her makeup was perfect as usual.
Tiffany was looking just as good in a red low-cut, figure-hugging dress that showed a lot of breast and a lot of leg. Stephen would have been distracted by her if not for the pile of cash sitting on the table.
“Check this out. The money will go into the casino vault for safekeeping overnight but during the games it will be on display in this,” Stephen showed them the perspex safe.
The inner workings of the safe and the money would be visible to the players and the spectators. It was just a stunt, but one designed to attract the kind of gamblers they wanted.
Lyle and Tina had found five very rich and very reckless poker players. All five had played and lost in high stakes games before but they won every now and then. Even the worst players get lucky and that’s why Tiffany was crucial to their plan.
Kurt was no schmuck when it came to Texas Holdem and he could beat the patsies fair and square nine times out of ten but they needed certainty. Because the rules of the tournament required each player to go all-in at least once in the game and it was winner takes all for the final pair, those odds weren’t good enough. Tiffany would only assist Kurt when he needed it but it would always be at a crucial time in the tournament.
Tiffany was good. Very good. She could riffle stack, overhand stack, and double lift and it would be imperceptible to almost anyone. The problem was that if you cheat too often you get caught; the odds are against you. Tiffany would be very judicious in doctoring the deal.
Stephen was liaison with the casino and had organised a poker room for their exclusive use. The casino advertised the tournament discreetly to its best customers. Those who were disappointed not to be playing could pay to watch. There would be places for only twenty spectators and they were sold out immediately.
The five dupes would be arriving in two days and Tiffany and Kurt worked hard at practicing their trade. Tina, Lyle and Stephen sat in to play so that Kurt had someone to play against.
That evening Kurt invited Tiffany to his room so they could practice their signals. Poker players watch each other and the dealer intently so they had to work hard to send and receive almost imperceptible signals to one and other. There wouldn’t be many, just a subtle signal to tell Kurt when to fold, when to bet and when to go all-in.
“We gotta be better than last time. I got caught out on the security camera,” Tiffany said, a little embarrassed that she had.
“Bullshit! Someone tipped off Brian Madsen. That asshole couldn’t find his ass with own hands,” Kurt was standing at the wet bar pouring them both a drink.
“All cheaters get caught eventually,” Tiffany took the proffered drink.
“Hey Tiff. If you were thinking of running a scam and you needed the best card mechanic on the West Coast, you wouldn’t think twice about getting her fired so that she needed the job,” Kurt looked at her over the rim of his glass.
“Fucking Lyle Brinkman!” Tiffany hissed.
“What about Stephen Bateman? How can you be so sure it wasn’t him?” Kurt countered.
“It could be either of them I suppose. Either way it’s too late to worry about it now,” Tiffany drained her glass and held it out for a refill.
“Aren’t you having a few too many Tiff? I thought you might have a hot date with mister Bateman, that guy is nuts for you, I can tell,” Kurt put more ice and a double hit of Jack in her glass.
“That’s why I’m throwing you a freebie tonight you lucky boy. Mister Bateman is getting a little schmaltzy for my liking. I’m the girl you fuck and tip as she leaves, not the girl you fall in love with,” Tiffany drained her glass and held it out again.
“I don’t know Tiff. You’d make the perfect wife. You understand baseball, you have a penis, you don’t get a period, and you love anal sex,” Kurt said sarcastically.
Tiffany just rattled the ice cubes in her glass.
“Hit me again lover, then come and fuck me a little. This time I’ll throw in some foreplay,” Tiffany chuckled.
She finished her drink and came over to where Kurt was sitting in a big overstuffed chair and straddled him, her dress hiked up to the top of her thighs. She put her arms around his neck and leaned in to kiss him. She teased him, putting just the tip of her tongue into Kurt’s mouth and then retracting it when he tried to kiss her harder.
“Bitch!” he sighed and pulled her closer, forcing his tongue into her mouth.
Tiffany growled with lust and wriggled in his lap, Kurt’s cock was pressing against her thigh and she broke the kiss just long enough to unzip him and free it. She let his cock rub on her silken-sheathed thighs while they kissed, then she reached between their bodies and squeezed him.
“Careful you don’t get cum on that dress Tiff, it looks expensive,” Kurt mumbled through crushed lips.
“I’d best take it off then,” she whispered into his ear and nibbled his lobe.
She stayed straddling Kurt but lifted herself up. She caught the hem of her skirt in both hands and lifted it up her body, peeling off her dress. Kurt helped her pull the dress over her head and then she dropped it to the floor.
She looked gorgeous. Her red satin bra and panties, red lipsticked lips, red high-heels, jet-black hair with subtle highlights contrasted with her ivory skin. She was wearing the sheerest of flesh-toned hold-up stockings which Kurt softly caressed as his mouth found hers again.
He freed her breasts and lowered his face to them, alternately suckling them as Tiffany’s nipples hardened in response. She cradled his head and encouraged him to lap and nip at her teats, gasping every time he did so.
They took a beat for Kurt to take off his shirt and pants and for Tiffany to free her penis and then she straddled him again, resuming their canoodling, kissing each other while Kurt stoked her breasts and she stroked his penis to full tumescence. Tiffany was hard too and freed her erection from the confines of her panties. Kurt deftly stroked it. It was big. Bigger than his in both length and girth and it seemed to pulse in his hand.
“I want to take you in my mouth,” Tiffany gasped in his ear.
“No honey. Stay exactly where you are,” Kurt whispered back to her.
He lifted Tiffany up, pulled her panties a side and lowered her onto his rampant penis, burying himself inside her all the way. Tiffany sighed and nibbled his ear and then kissed him passionately as she began to ride him. She clenched her buttocks and as she slowly lifted herself up and down as Kurt held onto her waist to guide her.
They didn’t talk. The communicated by gestures, by grunts and groans, as Tiffany, fully in control, rode his cock. She teased him, when he wanted to her go faster she slowed down, when he wanted to pull her tight she held him at arms length. Her cock was so inflamed and aroused that it was leaking a continuous stream of silvery pre-ejaculate onto his belly.
Kurt scooped up some of the slippery fluid and began to stroke Tiffany’s cock.
This had the desired effect.
She leaned into him and kissed him viciously, biting his lip, driving her ass down hard into his groin. She fucked him hard and fast and Kurt held her close with one arm around her waist and the other stroking her hard cock.
“Fuck me! Fuck me! Fuck me you asshole!” Tiffany was frenetic with lust.
Sitting astride Kurt this way drove his cock all the way inside her. She could lean either way, adjust her position and wriggle her buttocks to exhort every scintilla of pleasure. Her anus was alive with wonderful sensations as she worked herself on Kurt’s cock. She gasped into his mouth as she kissed him, her nails raked his neck and shoulders, and she bit his lip and thrashed herself against him as she felt her orgasm approaching.
Tiffany’s anus squeezed and massaged Kurt’s cock as she rode him, bucking in his lap and grinding her buttocks into his groin. He held onto her cock and squeezed it, feeling it convulse as it became close to eruption.
Kurt ejaculated, his scalding semen filled Tiffany’s anus just as she too orgasmed.
Her searing spend splashed onto his belly as Kurt gripped her by the hips and drove her down on his cock. Tiffany thrashed and writhed, milking him of his seed, her own cock convulsing and splattering his flesh with her issue.
She fell against him exhausted; spent. They were both panting. Kurt put his arms around her and she put her arms around him, nuzzling him, his cock slowly deflating inside her as she squeezed him with her anus, kissing him softly.
When they had caught their breath she made to move but Kurt held her close so she acquiesced and curled up in his lap like a kitten.
“Just as well you took that dress off,” Kurt pressed his lips to her soft cheek.
“Just as well,” she purred.
After a beat Kurt whispered in her ear.
“I have a proposition for you.”
“I seem to be getting a lot of those lately,” she snuggled up to him, cold in the air conditioning.
“You know the money splits a lot better two ways,” Kurt said.
Tiffany lifted her head and looked him in the eye.
Was this a test?
“Go on,” she said cautiously.
“I’m going to win the tournament. The casino manager will make a big deal of giving me the cash. Then they will issue me a bank check and the cash goes back to the cashier. What if I don’t share it?” Kurt softly ran his fingers through Tiffany’s hair.
“Then I think mister Bateman and mister and missus Brinkman will hunt you down. Lyle and Tina still know some pretty dangerous people Kurt,” Tiffany lifted her face to his.
“But what if I just disappeared. Liquidated everything I have and put it into a numbered account. Change my name and my identity and go and live on a beach somewhere,” Kurt mused.
“So why tell me?” Tiffany began to extricate herself from his lap.
She dabbed at herself with tissues and then cleaned up Kurt as best she could.
“What if you came along later and joined me? Disappeared, just like me?” he espoused.
“I gotta pay back my stake Kurt,” she replied gravely.
“Not if they can’t find you?” Kurt got out of the chair and began to dress.
Tiffany was stepping into her dress and turned her back to Kurt so he could close the zip.
“You don’t run out on the people I lent the money from. Their expertise is finding people,” Tiffany said.
“So pay them. We split nine million instead of ten,” he said resolutely.
“I know things are tight with you Tiff. You can stop selling your ass and retire. Live a life of luxury with me. Or not with me if you prefer, we still split it fifty-fifty,” Kurt turned her around to face him.
“I hate beaches. I burn easily,” Tiffany slipped out of his embrace and began to fix her makeup.
“So we go to the snow; whatever the fuck,” he held up his palms.
“Let me think about it,” she brushed her hair and got ready to leave.
“I thought you were going to stay the night. I though you wanted me to take me in your mouth?” Kurt grinned.
He was handsome and Tiffany’s heart skipped beat.
“Hey. You got a freebie with foreplay, don’t get greedy,” she lightly kissed his cheek and walked to the door.
To be continued
The app on Tiffany's phone buzzed and she checked it.
Stephen Bateman wanted to book her services this evening. She declined his request by simply pressing a soft key. She didn't have time for him tonight, Tina Brinkman had requested that Tiffany come around for a drink. They'd talk about old times and bury the hatchet.
Tiffany knew that there would be more than old times to be discussed. She really liked Tina but Lyle was a snake. Tina was enamoured with Lyle, she loved him unconditionally, it was one of Tina's few flaws.
Tina answered the door in a black lace peignoir that was virtually transparent. She was braless and wore black boy-leg panties, black fully-fashioned stockings and kitten-heel pumps. Her makeup was heavy but perfect as usual and her jewellery glittered in the lamplight, she was surrounded by a miasma of perfume.
"Why don't you just hold up a sign that says fuck me," Tiffany said caustically as she stepped around Tina into the apartment that was dark, lit only by a single lamp.
"Shut the fuck up you sarcastic bitch," Tina grabbed Tiffany by the wrist and spun her around.
She pulled Tiffany into her arms and kissed her deeply and intensely.
Tiffany dropped her handbag and wrapped her arms around Tina. Tina still had that lovely sweet taste and her body felt the same as it had all those years ago, a little bigger, but it was still Tina, the woman she had made love to so many times on and off camera that she had forgot how many.
"You still taste the same," Tiffany gasped as they broke the kiss.
"You smell the same and you even feel the same. I've missed you Tiff," Tina whispered and kissed her again.
Tiffany was wearing a simple navy and burgundy shift dress. It was Chanel of course, and cost over one thousand dollars off the rack. Tina flicked the shoulders of the dress down Tiffany's shoulders and she was left standing clad only in cerise full-cut nylon panties, bra and the same sheer hold-up stockings that she had worn to Kurt's hotel room the previous evening. She teetered on four-inch Jimmy Choo heels.
Their bodies moulded together, they instinctively knew where to touch and tease each other. Lipstick-lips parted as they gasped and probed each other's mouths with their tongues. Tiffany stepped out of the dress that was pooled around her ankles and allowed Tina to lead her to the bedroom. Neither of them pretended that they hadn't had sex on their minds from the second Tiffany had accepted Tina's invitation.
Tiffany lifted the thin straps of Tina's peignoir and smoothed them down her arms. It fell to the floor leaving her naked except for her underwear. Both women were left wearing only their intimates and were soon bra-less as they began the slow, lingering, exploration of bodies that were once very familiar. Tiffany found Tina's breast fuller than she remembered, but still firm, the flesh creamy. Her lips kissed Tina's areola and her tongue flicked across her stiffening nipples. Tina guided Tiffany's mouth from one succulent teat to the other and moaned as Tiffany teased her with her mouth.
She returned the favour, stripping Tiffany of her brassiere, softly caressing the heft of her bosom and then lowering her mouth to the enticing globes. Fingers replaced mouths on their bosoms as they yearned to kiss. Lips crushed together in restrained passion. Either of them could easily throw the other on the bed and fuck, but they wanted to savour the moment, to take their time rekindling their lust for each other.
Tiffany smoothed her hands along Tina's thighs, tracing the backseam of her stockings, knowing that it would drive Tina wild with desire. She lightly drifted her fingers across the front of Tina's panties and found her erect, the fabric of her panties wet with precum. Tina gasped and slid her hands down Tiffany's taunt flesh and found her also tumescent. She hadn't taped and her large member was folded under her buttocks. Tina released it, using featherlight caresses she bought it fully erect.
They were standing next to the bed and Tiffany sat down on it so that Tina stood before her. She used her mouth on Tina's belly, following the curve of her hips with her tongue, kissing and licking the juncture where her thighs joined her torso. She glided her hands up down Tina's thighs, listening to her mew with desire.
She played her tongue on the milky flesh above Tina's stocking-tops, her fingers digging into Tina's buttocks. Only when Tina begged for it did Tiffany release Tina's penis from the confines of her panties. She used her fingers to sylphlikely caress the throbbing appendage. Tiffany felt Tina shudder, her knees nearly giving way as she slowly and tenderly teased Tina's rampant phallus. Tiffany licked the silvery issue oozing from the eye of Tina's cock.
She suddenly engulfed the rampant flesh, using her tongue and her lips in ways she knew would drive Tina wild with lust and wantonness. Tina gently put her hands to Tiffany's face to guide her mouth where she needed it. She knew that Tiffany hated men pushing her head to their groins so she encouraged her lover rather than being insistent. Tiffany suckled Tina's scrotum, taking it into her mouth and using her tongue to tease and fondle the delicate flesh while her fingers caressed Tina's rampant member.
Tina mewed and gasped as her lover drove her to the edge of climax and then retreated, keeping her on the verge of fulfilment and then backing off.
"You bitch! You know how to grind my gears," Tina sighed.
Tina reluctantly pulled away from Tiffany and sat beside her on the bed. She wanted to kiss her, to hold her, to caress her. Tina lowered Tiffany onto the bed and explored Tiffany's body with her mouth and her fingers. When she had Tiffany fully tumescent she knelt on the bed and offered her buttocks in supplication.
"Fuck me darling, please fuck me," Tina pleaded.
Tiffany knelt between Tina's upraised derriere and lowered her panties. She licked Tina's puckered sphincter until Tina heels drummed on the bedspread and demanded that Tiffany penetrate her.
Tiffany's cock was hard and throbbing, ready to be enclosed inside Tina's tight furrow. She knew that if she plunged it into Tina's anus she would likely hurt her lover so she prodded at her crinkled entrance and slowly inserted herself inch by inch, holding onto Tina's waist to steady herself.
"Oh god yes. Oh please fuck me lover," Tina begged when Tiffany had fully inserted herself inside Tina's tight, hot burrow.
Tiffany began to work her hard cock in and out Tina's ass, enjoying the pleasure and the power. Tina, supplicant before her, was begging to be taken.
It came as no surprise to Tiffany when Lyle climbed on the bed, naked and rampant. He'd obviously been watching them from the dark corner of the room. Tiffany knew he was a voyeur who loved to watch his wife be taken by both friends and strangers. He used to watch Tiffany and Tina perform for the camera and then ravage them both when they were finished on set still covered in semen.
Lyle kissed Tiffany's buttocks and fondled her scrotum as she fucked his wife. Then he scooted between her legs and positioned himself at the entrance to her anus. He pressed forward, holding Tiffany by the hips until he was inside her all the way then began to fuck her.
Tiffany was in the unique position of fucking someone while she herself was being fucked. The silence was broken by gasps, cries and moans as they fucked. Tiffany enjoyed the fullness of Lyle inside her whilst her own penis was buried inside Tina's tight ass. She was being pleasured doubly and would soon climax.
She reached under Tina and squeezed Tina's cock, feeling it throb in her grasp. Tina was pushing back hard and Tiffany knew that Tina was close to orgasm too. She drove herself all the way inside Tina's rectum and ejaculated, howling with delight as she felt Lyle spend himself inside her. Tiffany's fingers were drenched in hot sticky semen as Tina released. All three of them climaxed in concert.
Tiffany collapsed on top of Tina and expended the remainder of her issue deep inside her. Lyle fell on top of Tiffany and continued to pound away at her buttocks until he had finished coming.
Tina was nearly suffocated under the weight of them both but she was so aflame with desire that she didn't care, in fact it heightened her satisfaction.
Lyle rolled off Tiffany when he was done and Tiffany eased herself out of Tina. The three of them kissed and caressed each other on the big bed. The ladies kicked off their heels and got under the covers with Lyle and began to canoodle and fondle one and then the other until they were ready to fuck again.
After their second round Lyle got out of bed and bought back drinks. Lots of drinks. They drank and fucked the evening away until they were exhausted.
And then Lyle began to talk.
Tiffany knew this was why she was really here.
"Do you know Scoot Spetman?" Lyle asked as they sat drinking and smoking on the deck outside their room.
"I know of him. He's a poker player who loses more than he wins. Can't help overcalling a small pocket pair pre-flop or calling with a weak ace, hoping the other dupe will fold," Tiffany replied.
"He's the player that Kurt Bentley will be up against in the final game," Lyle explained.
"He's a lazy fuck who likes to spend his dad's well earned cash but daddy has had about enough. Daddy has threatened to cut off his cash flow so we offered him a proposition," Lyle turned on his lounge to face Tiffany.
"We already have a proposition. We take the dupes for five million and split it between the five of us," Tiffany studied the end of her cigarette giving away nothing.
"Yeah but if we let Scoot win the tournament we can split it two ways, half for you and half for Tina and myself," Lyle grinned.
"That math doesn't work. What about Scoot?" Tiffany sat up, she was interested.
"Anyone with a name like Scoot deserves to be taken. He can't put the money in his trust fund because daddy is about to lock him out of it. So my lovely wife has used her winning charms to convince him to put his money into an interest bearing account. He's already put his ante in there," Lyle handed Tiffany his tablet which had a webpage open to Scoot's bank account.
"Pretty sure what you are proposing is illegal," Tiffany studied the ledger.
Scoot had nearly three million dollars in the account.
"Everything we are doing here is illegal Tiff. Everyone knows you had to borrow your buy in, that you're the poor cousin. Why not split the ten million two ways instead of five?" Lyle said.
"But there are three of us," Tiffany countered.
"You take half the pot from the poker game, we'll take the other half plus whatever Scoot has left in his account. We'll clean him out and he can go beg daddy for more," Tina joined in.
"So I throw the game and Scoot takes the pot, pays the rake and puts the cashier's check into his interest bearing account which Tina has illegally acquired access to?" Tiffany mused.
"Kurt and Stephen will be pissed at you but what can they do? You can tell them that Scoot was stupidly lucky, you know you can't guarantee the outcome of a poker game. And if Scoot goes to the authorities daddy finds out he's been playing high-stakes poker and cuts him off. The worm Tina's will use to access Scoot's account is untraceable," Lyle had it all planned.
"So I walk away with five million and you guys get around seven or eight, depending on what Scoot has in his account when you fleece it?" Tiffany did the math.
"We're happy with that Tiff. You're doing the heavy lifting; we just rake in the rewards," Tina gave Tiffany her winning smile.
Tiffany had seen alligators in the swap smile exactly like that. She trusted them not.
"Ok let me think it over," Tiffany stood and started to gather her things.
"Don't think about it too long Tiff," Lyle said, sounding a little more threatening than he wanted to.
"Hey lover; aren't you gonna stay the night?" Tina sidled up to her.
"Tina. My ass is sore, my cock is sore, my lips are sore and my brain is sore. Time to go home and rest and get ready for a busy three days. Those mooks won't fleece themselves," Tiffany stepped into her heels and picked up her handbag.
The next day at the Grand Lake Hotel and Casino Stephen Bateman opened the poker room for the casino's first high-stakes Texas holdem poker tournament. The six players sat at the table with Tiffany Robinson dealing. The players had drawn cards for their position at the table and lucky for Tiffany, Kurt Bentley was to her left in the best spot for her to deal to.
There were twenty paying spectators around the table and Tiffany guessed that some of them were there to see the tranny porn star turned card dealer as much as to watch the game. Being VIP benefactors, Lyle and Tina Brinkman and Stephen Bateman had high-backed stools to sit on to watch the game. The casino manager made a show of putting the ten million dollars in cash in the perspex safe, the door of which was left open with a stoic-faced rent-a-cop guarding it. There was a hush from the crowd when the money arrived.
Scoot Spetman was to Tiffany's right. The first few rounds the players played tight, folding often with mainly small pots at stake. Tiffany spiced things by dealing two of the dupes a pair of hole cards each and laying down a flop that both thought was to their advantage. One of the dupes went all-in on the river and the other followed suit, by then the other four players had folded.
One down and five to go thought Tiffany.
By the end of the day's play two of the dupes were out, Kurt and Scoot were up half a million each with the remaining two players just about even.
After the money was returned to the cashier Tiffany, Kurt, Stephen, Lyle and Tina retired to Stephen's suite. Tina acted as hostess pouring drinks. Everyone was happy with how thing were panning out but Stephen was not happy with Tiffany. He followed her out to the balcony. She was leaning on the rail, drink in hand, smoking a cigarette.
Tiff was wearing a low-cut white satin sheath, split on up one side. The breeze blew the spilt open displaying her long legs clad in shimmering flesh-toned nylons all the way to the top of her thighs. Stephen caught his breath.
"You've been avoiding me," he said as he sidled up to her.
"No. I'm just not servicing any clients while I'm doing this job," she stared off into the distance.
"Is that all I am; a client?" he turned her face to his.
He brushed away her bangs and looked into those emerald green eyes.
"No you're not. That's why I turned you down last night," she stared back at him.
"So what did you do?" Stephen stroked her cheek.
"I had a business meeting," she took a drag of her cigarette.
"Really?" he took his hand from her face.
"Don't pout. It doesn't become you," she flicked her cigarette away.
Tiffany stepped into him and put her head on his shoulder.
"I'll stay the night ok?" she nuzzled his neck.
Stephen lifted her face to his and kissed her.
They went back inside and Stephen did his best to get the others to leave but they were all excited and wanted to talk about the day's events. Tiffany excused herself and went to use the restroom. Lyle and Tina had a secret meeting with Scoot Spetman so they made their excuses and left, followed a little later by Kurt Bentley.
Stephen wondered where Tiffany had gone and was worried that she might have slipped out with others.
He was delightfully surprised to find her lying on his bed sans dress.
"If you think you're putting your leaky cock anywhere near that white satin dress you're dreaming," she smiled up at him.
"What about your leaky cock," he began to hurriedly strip.
"As a matter of fact it is leaking in anticipation. Another reason I took my dress off," she showed him the bulge in her panties.
She looked magnificent lying on the black satin comforter wearing white satin panties, bra, flesh-toned sheer hold-up stockings and white four-inch heel Christian Louboutin's.
Stephen leapt on the bed and Tiffany opened her arms and her legs for him.
"Take the foreplay as wrote. I want you in me. Right now!" she growled and wrapped her arms and legs around him.
She raised her buttocks off the bed so that Stephen could easily find her sphincter. He pulled aside the gusset of her panties and slid inside her, his passage eased by the pre-placed lubricant capsules.
"Oh god yes fuck me!" Tiffany slid her stocking-sheathed legs along his flank to encourage him.
Stephen felt Tiffany use her anal muscles to squeeze his cock as he slowly fucked her, grinding his pubis against hers, her hard cock pressing on his belly. He could feel her slippery precum on his flesh.
Stephen kissed Tiffany deeply, driving his tongue into mouth as he drove his hard cock deep inside her anus, Tiffany writhed beneath him, encouraging him to fuck her harder. She felt so wanton and sluttish, she just wanted Stephen to use her; to fuck her like she was his toy. Sometimes she just wanted to let go, not be in charge, to be a plaything for a powerful man.
Tiffany slid her gossamer-sheathed legs along Stephen's tender skin, she knew it drove him wild, she raked her high-heels on his flanks.
"Take my cock Tiffany. Take my cock in your ass you fucking whore!" Stephen howled as his excitement peaked.
"Come in me Stephen, fill my ass with your hot spunk!" Tiffany lifted her buttocks up high so that Stephen could get all of his cock inside her.
"I'm coming! I'm coming!" Stephen ejaculted, filling her anus with his warm creamy issue.
"Oh god yesss!" Tiffany came too, her semen splashed on Stephen's belly.
He jackhammered his cock in and out Tiffany's tight ass until he was spent and Tiffany was exhausted.
They lay in each other's arms later kissing and canoodling. Stephen tenderly flicked a stray lock of hair from her eyes.
"You know I don't really think you're a whore," he said bashfully.
"Stephen. Sometimes it's just sex and it's ok to roleplay a little. I know you have real feeling for me, just as I really like you," Tiffany stroked his cheek.
"I think it's more than that Tiff. I think I..." Tiffany put her finger to his lips to silence him.
"Don't say something we will both regret you saying Stephen. Just hold me, kiss me, make love to me. That will do for tonight," she sighed and snuggled up to him.
The next day they lost two more dupes from the tournament leaving only Kurt Bentley and Scoot Spetman at the table.
It was decision time for Tiffany. Did she take up Kurt's proposal or Lyle's, or neither.
Kurt's proposal was the easiest to accomplish, the safest, and guaranteed her half the pot but going into hiding from the people she had borrowed the money from was impossible. They would search the ends of the earth for her and they wouldn't be nice to her when they found her.
She didn't like Lyle but she did like Tina so that was a conundrum. If Lyle told Tina to take all of Scoot's money and give Tiffany none would she do it?
She could lie to Kurt and Stephen easily enough, nothing was guaranteed in poker but neither would believe her. But what could they do? Accuse her of cheating the cheaters?
Tiffany made up her mind and reached for her phone.
The final day of the tournament was winner takes all, at some stage both players would have to go all in. Tiffany played it straight for most of the afternoon and let Kurt get the upper hand using his poker skills. Scoot copped a few lucky breaks and at one stage it looked like he was going to upset their plans.
Scoot was holding a small pair with nothing else he could use on the board but he had bet big on the flop, the turn and the river hoping to get his three of a kind. He was tempted try his luck and pretend he had a winning hand.
You could cut the tension with a knife. Scoot Spetman studied his hole cards and then his hands moved to the stacks of chips in front him and hovered there. He was thinking of going all-in. If he did then Kurt would have no choice but to also go all-in also which would put Scoot out of the tournament. That wasn't the plan.
Scoot looked at Kurt intently, watching the sweat bead on his forehead. Kurt knew that Scoot was bluffing and Scoot knew that Kurt knew. Scoot was fucking with him; having some fun.
Tiffany tried to look unperturbed but she was seething. This wasn't how this round was supposed to go down. Scoot was supposed to keep playing a while longer, building the tension, not to have his ass handed to him by Kurt Bentley.
"I fold," Scoot backed his hands away from the stacks.
Kurt exhaled and dragged in the pot without showing his hand.
When it was time to make the sting Tiffany gave Kurt the sign.
Tiffany had dealt Scoot a pair of nines. Kurt have been dealt two kings.
Tiffany burned a card and dropped a nine, a king, and a seven in the flop.
The betting got heavy and the Tiffany dropped a seven on the turn.
Kurt went all in and Scoot followed suit.
When Tiffany turned a nine on the river everyone gasped. Kurt Bentley was reaching for the pot when he realised that he hadn't won. He looked at Tiffany with astonishment. Stephen Bateman looked equally amazed. Lyle and Tina Brinkman worked hard at keeping po-faced.
Stephen was trying to understand what was happening. Why was Scoot Spetman raking in the chips instead of Kurt?
Suddenly the doors burst open and four black-suited individuals holding badges in one hand and pistols in the other rushed into the room, fanning out to cover everyone in the room.
"FBI! Nobody move. You three stay put and put your hands on the table," the lead agent pointed her weapon at the gamblers and the dealer.
"And you people; get against the wall, put your palms flat against it," the second female agent growled.
There were two female and two male agents, and as a sign of the times, the female agents were obviously in charge. They looked to be hiding killer bodies inside their MIB suits. One was a trim redhead and the other taller and blonde. The men were muscled and sported buzzcuts.
"What the hell is going on here?" Stephen Bateman demanded.
"What's going on is that five people in this room are under arrest for conspiracy to commit fraud, deception with intent to commit a felony, and a whole bunch of other charges that I'm sure will follow," the redhead said.
"Tiffany Robinson, Kurt Bentley, Stephen Bateman, you're coming with us to be interviewed and charged. You too mister and misses Brinkman," Lyle and Tina hung their heads.
"Cuff them and take them downstairs," the blonde said to the buzzcuts.
Tiffany, Stephen, Lyle, Tina and Kurt were handcuffed.
The spectators, their backs against the wall, look on in stunned amazement.
"What about the money? There's ten million in cash in that safe," Stephen was furious.
"We are taking everything in this room into evidence as soon as our forensic team get here and do their thing. The paperwork will be lodged with the Federal prosecutor and you will receive copies. At this stage we don't know who has legal ownership of the cash but that's not our concern, that's for the court to decide," The redhead explained.
"Okay get them out of here," she ordered the two buzzcuts who had holstered their weapons but were still not to be messed with.
Tiffany, Stephen, Lyle, Tina and Kurt were led outside, one agent in front and the other in the rear. The casino manager was standing outside the room wringing his hands looking alarmed and frightened.
They were led to the back of the casino and into a service elevator which stopped at the basement. An unmarked black van with the rear doors open was parked next to the elevator. Another buzzcut, probably the driver, helped his compatriots load them into the van and get them seated.
The van took off with a screech of tyres and all five bounced up and down until the van settled onto the blacktop.
"What the fuck just happened?" Kurt Bentley looked around at the others, the accusation evident in his tone of voice.
"Someone ratted us out," Tiffany was equally angry.
"Is this part of your deal with the FBI? Did you trade us to get out from under the Raffe Ignesman thing?" Stephen Bateman growled.
Tina and Lyle shook their heads violently.
"We already had our deal with the FBI. What about Tiff? Did she need to do a deal?" the attention turned to Tiffany.
"She was supposed to deal me the winning hand but somehow Scoot won the pot. What the fuck was that about?" Kurt glared at Tiffany.
Tiffany looked at Stephen who shook his head.
"Were you two in cahoots!" Kurt looked at Tiffany and then Stephen.
Tiffany began to cry.
"The people I borrowed money from won't care who doublecrossed who. They'll just want their money back and the vig and when I haven't got it..." her voice trailed off; she could no longer talk because she was sobbing so hard.
"I can help you out Tiff," Stephen tried to take her cuffed hands in his but she shook him off.
The accusations went backwards and forwards for the next thirty minutes until the van finally came to a halt. They had no idea where they were, there were no windows and the rear of the van was walled off from the cab. They heard the driver and passenger doors open and the crunch of receding footsteps and then nothing.
And then still nothing.
And then still nothing.
"Fuck!" Stephen Bateman shook his head.
"We were so busy blaming each other that we didn't realise that we've been scammed!"
He got up from his seat and sat down on the floor of the van and began to kick the back door. Lyle and Kurt joined him and after fifteen minutes the door finally sprang open.
The van was parked exactly where they had been loaded into it. They were back at the Grand Lake Hotel and Casino.
It was almost comical watching the six figures, two of them dressed in evening gowns, scramble out of the van with their wrists handcuffed in front of them. They took the elevator to the gaming room floor and then ran to the poker room. There was a small crowd of bewildered hotel staff milling around inside the room. They stopped what they were doing and stared at the six well-dressed handcuffed people.
"Don't just stand there you imbeciles! Call the police! We've been robbed!" Stephen Bateman screamed at them.
The safe was empty.
The police came and released them from their handcuffs and took them downtown to be interviewed. The other witnesses were innocent and couldn't tell the police anything and Tiffany, Stephen, Kurt, Lyle and Tina could only tell the police that their game had been raided and the money stolen. They had to keep schtum about their scam to steal the pot or risk going to jail.
Scoot Spetman was raising hell claiming he had won all the money fair and square but the police didn't seem to care who had won the final pot. As far as they were concerned a casino had been robbed and that was bad for business, they just wanted to catch whoever had done it. The casino could decide who rightfully had claim to the money if it was ever recovered.
The police released the five conspirators one at a time and their phones lit up with texts back and forth. They agreed to meet in Stephen's penthouse and try to unravel what had happened. Tiffany didn't come to the meet. She disappeared that very evening and they argued amongst themselves as to whether she was hiding from the men who had lent her the million dollars or if she was somehow involved the scam involving the phoney FBI agents.
For three months Stephen Bateman tried to find her. Tiffany's condo had been sold fully-furnished and she had cleaned out of all of her personal possessions. Likewise her Dodge Viper had been sold off. All of her bank accounts had been closed and the money transferred offshore. Try as he might, Stephen couldn't trace the money.
It was as if Tiffany Robinson had disappeared off the face of the earth.
Stephen Bateman sat in a well appointed conference room on the first floor of Executive Solutions, a company that specialised in covert surveillance, finding missing persons, and in civil investigations. Having exhausted all efforts to find Tiffany, Stephen Bateman had decided to go to the experts.
He was met by a man dressed in a business suit who looked like he could kill you with his thumb. Which he could.
They ordered coffee and then Stephen Bateman explained why he was here.
"So how much is it going to cost me for your company to find Tiffany Robinson?" Stephen asked.
"I'm sorry mister Bateman I don't think we can take your case," the man said.
"It's a conflict of interest for us you see."
Stephen Bateman looked bemused and was about to speak.
"Before you say anything sir. Let me introduce our two CEOs, Natalie Styles and Cassandra Rivers," the man waved his hand at the double-doors which opened right on cue.
Two stunning women entered the room, a miasma of perfume announcing their arrival.
The first, a trim redheaded woman in a tight-fitting navy-blue business suit, a cream silk blouse and silky sheer pantyhose, her ginger hair was styled with layered bangs and rested on her shoulders, her makeup emphasised her peaches-and-cream complexion although she favoured heavy black mascara and bright-red lipstick.
The second was dressed almost identically, she too was stunning and was a little taller with blonde hair.
"The FBI agents," Stephen smiled and shook his head.
"Natalie Styles, ex FBI agent and co-founder of Executive Solutions," the redhead approached and offered her hand.
"Cassandra Rivers, ex biker-bitch and also co-founder of Executive Solutions," the blonde shook his hand and then they all sat.
The trained killer in the business suit left them to their business.
"Look..." Stephen tried to begin but Natalie held up a finger.
"I'm going to let Cassie explain. She's closer to the source of this incident than I am," she said calmly.
"Believe it or not, a few years ago, I was recruited by the FBI to work undercover as a biker; a full-patch member of the Beasts of Burden MC. Natalie here was my FBI handler," Cassie began.
"At one point the Beasts of Burden patched over the Sisters of Satan, an all-girl biker club who happened to own the Medusa casino in Las Vegas which was fronted by a woman named Jill Saint John. Jill became a very close personal friend of mine," Cassie looked at Natalie almost apologetically.
"No further details will be provided other than at one time Miss Tiffany Robinson worked for Jill Saint John as a dealer in the Medusa casino. Being a trans-woman myself, Tiffany and I became very good friends," Cassie could see the lights switching on in Stephen's brain.
"So when Tiff realised that she couldn't trust Lyle and Tina Brinkman, Kurt Bentley and even you mister Bateman, she came to us," Cassie turned to a small wet bar set up at the end of the conference room.
"So let me get this straight. Tiffany, the woman I am hopelessly in love with, didn't trust me," Stephen took the double scotch that Cassie had poured for him.
Nat and Cassie had bourbon the rocks.
"She didn't trust anyone. But she trusts me so I used my company to protect her interests," Cassie raised her glass.
"She and your company robbed us of ten million dollars!" Stephen slammed his glass down on the conference table.
He put his hands to his face and rubbed his eyes and then ran his fingers through his mane.
"God. I always knew that Tiff was the smartest person in the room wherever she was and regardless of the company," Stephen raised his glass and to the sky and drained his glass.
He was resigned. There was nothing he could do. He'd been doublecrossed or triple-crossed or something. There was no taking on Executive Solutions, they could make him disappear in a instant and no one would ever find him.
He pushed back his chair, ready to leave.
"Wouldn't you like to see her before you go?" Natalie asked just as he got to the door.
Stephen froze.
"She's here?" he turned around.
"We'll give you some privacy shall we," Cassie and Natalie put down their drinks and left the room.
Tiffany entered.
Tiffany had changed a lot. She'd put on some weight and died her hair red and let it grow out. She wore it piled on top of her head. Also her breasts were a lot bigger. She was still stunning, she was curvy and had those curves in all the right places. Think Christina Hendricks in Mad Men.
She was wearing a tight-fitting black business suit with a skirt that was indecently short and showed off a lot of nylon-sheathed leg. The buttons on her blouse and jacket strained to contain her large breasts. She was gliding on black stiletto high heels.
Stephen stood there stunned and speechless.
"Did you mean what you said about me being the smartest person in the room?" those succulent red lips curved into a smile.
Stephen just nodded.
Tiffany walked right up to him and put her lips on his. Instinctively Stephen put his arms around her.
They kissed... for a long time.
"But how?" he began.
"Not now; later," Tiffany took his hand and led him towards the doors.
The End
Please, please, please leave a comment. What was good? What was bad? I can't improve without criticism and encouragement xxx Michele