Tiffany's Deal Ch. 01

Chapter One -- The Deal

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 xxx Michele

Tiffany was not the 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.