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Tiffany's Deal By Michele Nylons Chapter One - The Deal 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 shut down 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