Tiffany's Deal Ch. 02

Chapter Two - The Flop

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 eighteen 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.