Tiffany's Deal Ch. 01

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.