Tiffany's Deal - Chapter Two free porn video

Tiffany's Deal By Michele Nylons 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 sixteen year old girl. Tom is no more," Tiffany said defiantly to her mother. "Ok Tiffany. Let's see how that works. To start with lets go and get your hair done and buy you some decent clothes." She patted her new daughter's hand. Kay took her new daughter out and did exactly that, getting Tiffany's hair cut in a style that suited her, buying her clothes and makeup and even helping Tiffany present herself as a young woman. Kay told herself that it was just another fad but deep down inside she knew that her boy was not happy in his skin and as she watched as Tiffany blossom she wondered how her husband would take it on his return. Tiffany's father was away on a navy deployment for four months in South East Asia and neither Tiffany nor Kay had told him that Tom was now Tiffany. There were also problems at school. Although Tiffany's school prided itself on being inclusive and tolerant the practicalities of a male student suddenly turning up one day and claiming to be female were very hard to deal with. What toilet was she to use? Which team did she swim for? And of course the daily ridicule and taunting from the less tolerant students was awful. Tiffany dropped out of school with the intention of completing her studies elsewhere when she had fully transitioned. Kay was heartbroken and fearful of her husband's reaction, which she had every right to be. When Tom senior returned home from duty overseas and saw his boy was now presenting as a girl he lost it. He threw Tiffany out of the house with all of her belongings. "I'm going down to the CPO Club to get drunk. I want that freak out of my house by the time I get back!" Tom senior roared. Kay arranged for her sister Shelley to take Tiffany in. Shelley was the family misfit who had left the family home as soon as she could to pursue a bohemian lifestyle. She had lived like a gypsy, moving around various communes and alternative cooperatives following her dreams. In her mid-forties she found that reality bites and that apart from her looks and her knowledge of all things arty and spiritual, she had nothing. Shelley moved in with her partner Remy and they scraped together enough money to open 'Bric-a-Brac', a curio, trinket and antiquities store which did moderately well. Shelley had settled down with Remy but they had no children, nor did they intend to. Because of the rebellious alternative lifestyle that Shelley had lived she could identify with Tiffany's struggle to be accepted living in a gender to which she was not born. "A new city, a new home, and a new beginning." Shelley hugged her new niece and welcomed her into her home. The arrangement was that Tiffany would live with her aunt, who lived four hours drive away, and Kay would come to visit her daughter once a month. Tiffany loved living with Shelley and Remy. She had her own room, was given all the freedom she wanted, and she worked in the store to help pay her way. Free of the bonds of her past Tiffany went about reinventing herself. With practice she was soon totally passable as a girl, a flat-chested girl, but a girl still the same. She had developed female mannerisms and patterns of speech and importantly, after exploring the Internet and with extensive practise, she learned how to tuck and gaff. Tom Robinson disappeared off the face of the earth completely, replaced by Tiffany. There were still many challenges ahead of her, she was still legally male and dealing with the authorities was difficult. Tiffany had to spend time under the care of a psychologist and get a sworn statement from her mother in order to get her gender altered on her birth certificate and a driver's licence issued reflecting her new name and gender. But she counted herself lucky, some states required proof of sex reassignment surgery before they would change a person's gender. Living full time as a girl was both a relief and joy. She developed her own style and as much as Shelley encouraged her to adopt her bohemian-chic dress style of flowing embroidered skirts and 'peasant look', Tiffany decided to go to the other extreme. Tiffany had developed a taste for eighties fashion, smart casual, and business wear. The exact opposite of her aunt. "It's so funny that I rebelled by wearing tie-dyed t-shirts and bell- bottoms and you rebel against me by dressing like a model out of a Robert Palmer music video," referring to Tiffany's pale skin and heavy makeup. "Actually I think it's good that we have totally different styles, you should present yourself to the world as you see fit," Shelley encouraged her niece. Tiffany initially spent most of her wages on clothes, makeup, and accessories, supplementing the accoutrements that her mother had bought her. Working in Bric-a-Brac she wore a uniform of her own design: a tight-fitting navy-blue skirt, white blouse, flesh-toned pantyhose and black high heels. Her makeup featured smoky eyes, bright red glossy lips and a little rouge on her alabaster skin to highlight her cheekbones. Tiffany had continued to dye her hair black from the days when she had been Goth because she liked the contrast of the black hair against her ivory skin. She wore it in a shaggy shoulder-length bob with bangs. She was tempted to buy a pair of breastforms but discovered that a padded bra gave her just enough bosom. It suited her not to have large breasts, being tall, svelte and long-legged. "I really like your look Tiffany. Very professional and it somehow works; me dressing like a hippy and you dressing like a businesswoman. You must be driving the boys wild." Shelley beamed when Tiffany presented herself in the shop for the first time sporting her new professional look. Tiffany blushed. She was still uncertain about her sexuality. She wasn't particularly attracted to boys her own age but she was attracted to older men; she was also attracted to some women. When she masturbated her choice of pornography was usually transsexual women having sex with mature men but she also liked tranny-on-tranny porn. She found it all a little confusing and decided to defer engaging in a physical relationship until she was absolutely ready to do so. Of course it didn't take long for word to get around that a stunning young woman was working in the store. Bric-a-Brac was soon a regular haunt for teenage boys and young men who wanted to see the striking young shopgirl who worked the costume jewellery and trinket counter. Shelley was no harpy either and the young men often gave her a second look. Tiffany remained shy around men and rejected any advances made to her. The extra traffic helped sales because the young men needed an excuse to be in the shop so they made purchases. The young men attracted young women, so the cycle generated an increase in income. But it wasn't just the young men who were attracted Tiffany. Remy had watched her blossom like a butterfly, transforming from a gangly young boy dressed as a girl into a sophisticated self-assured young woman who you would hardly guess was a genetic male. He liked her style. He would never tell Shelley this but he thought she had become dowdy as she had gotten older and the 'vintage-hippie' thing was no longer appealing. Shelley was still attractive but Tiffany's 'killer-chic' look was sophisticated, young, and sexy. Even when she wasn't working in the store Tiffany wore full makeup usually with dresses and skirts. She was seldom seen out of nylons and heels even on the rare occasions when she wore jeans, which she did with panache. Remy was captivated by Tiffany and although he knew it was wrong, he desired her. He fantasised about having sex with her, she sitting in his lap kissing him, on her knees fellating him, bent over the shop counter while he fucked her. He knew that the worst possible thing he could do would be to try to seduce her but he couldn't help himself when the opportunity arose. "Don't you guys burn down my store," Shelley joked and waved goodbye out the driver's side window of her Ram Promaster City van. Shelley was off on her twice-yearly treasure hunt as she called it. Inspired by the TV show American Pickers she travelled around the bazaars looking to buy curios, small antiques, jewellery and baubles to sell at a profit in Bric-a-Brac. Remy thought it was a waste of time and money once you deducted gas, food and accommodation from the calculations. But this time he was glad to see her go. He would have nearly three weeks alone with Tiffany. Because she had recently moved in and because of her unique situation Tiffany was pretty much a loner, although not really a recluse. She loved to go out and she loved to engage with Shelley and Remy but she was disinclined to form any friendships just yet despite the many offers from both boys and girls. She and Remy had gotten very close and she had to admit that she had a teenage crush on him. He was a little younger than Shelley and incredibly handsome. He had his own style which Tiffany described as 'urban cowboy'. She had seen him with his shirt off and he was toned, he worked out every day. He and Tiffany played cards together and he taught Tiffany to do card tricks and sleight of hand. He showed her lifts and riffle deals where he was able to stack the deck and win every time. He also showed her how to 'second deal', how to count cards even how to mark a deck. He had worked as a blackjack dealer in Reno before he met Shelley. Tiffany trusted Remy and asked him to take her swimming as she was embarrassed about being flat-chested and although she had to learned tuck and gaff she was not really confident about being seen in a swimsuit. Not that she need have worried, although she was not at all endowed in the chest area she was still stunning in her black spandex Nike high- neck one-piece swimsuit. It clung to her like a second skin and the high neck averted attention from her meagre breasts and accentuated her long elegant neck and pretty face. The suit flattered her figure. She was a little self-conscious about her ample behind but she needn't have been; it was sexy. Swimming gave her the opportunity to flaunt her long, toned legs. Her flesh looked almost translucent when the black spandex was wet and clung to her creamy white skin. Remy took her to an indoor pool three times a week and it was one his favourite activities. He'd change into his Speedos and watch her swim lap after lap and ogle her whenever she got in and out of the pool. After her laps he'd join her in the pool and they would horseplay around. He took every opportunity to rub against her and often had to wait for his erection to go down before he could get out of the pool. Tiffany was no fool and she knew what he was up to, but because of her infatuation with Remy she tolerated his behaviour. She also noticed that he liked to leer at her, particularly when she was dressed in her work attire. She deliberately teased him, bending over in his presence, asking him to hold the stepladder steady while she climbed it and sitting with her legs slightly open. Whenever the occasion presented itself Remy would brush or graze against her, he particularly liked to squeeze past her when she was behind the counter and his groin pressed against her buttocks. Tiffany began to fantasise about Remy. He would take her in his arms and kiss her and then they would do unspeakable things to each other. She'd seen plenty of transsexual porn and knew how transsexual women used their mouths and anuses to satisfy men's desires. She would wake up with her panties sticky and have to wash the sheets. Shelley had only been gone one day when Remy made his move. "Hey Tiff, wanna sit with me and watch some Netflix?" Remy called out to her. Bric-a-Brac stayed open late on Fridays and Saturdays and it was Tiffany's turn to lock up the store. They took it in turns working the late shift so it was dark in the house when she came in. The living room was cozy, the only light came from the TV. Remy was sitting on the two-seater couch and he patted the space beside him. "Come on and I'll buy you a beer," he quipped. Shelley and Remy had a very tolerant attitude to drugs and alcohol and believed both should be used often but in moderation. Tiffany was allowed a beer or a glass of wine with dinner. Tiffany, still dressed in her work attire, sat down next to Remy who popped her a cold beer and put his arm along the back of the sofa. His feet rested on a poufe and he schlepped it her way with his feet so they could share. Tiffany put her feet on the poufe and slipped off her heels. "Lovely." She rubbed her feet and wriggled her toes. Remy leered at her feet and her cute toes sheathed in gossamer tan nylons, her toenails were painted bright red. His eyes followed her legs, her skirt had ridden up and the top of her thighs were exposed to his gaze. Tiffany felt his eyes on her and caught her breath; she pretended not to notice and sipped her beer. She was aware of how close they were on the couch, his body was almost touching hers and his arm was behind her on the back of the couch. She felt crowded by him. Tiffany could smell him too. There was a manly undercurrent to his scent, almost musky, despite that he was obviously freshly showered and applied aftershave and deodorant and used mouthwash. And that was another thing she hadn't noticed until she sat down. He was dressed only in a bathrobe and she suspected the expensive Dolce and Gabbana cotton-spandex briefs he liked. She and Shelley shared the laundry duties so she knew what type of underwear he wore. "What are we watching?" Tiffany attempted to break the tension. "It's a show called Easy and this episode is called Art and Life." Remy pointed his chin towards the TV and slurped on his beer. "Oh my god," Tiffany whispered. A stunning young blonde bombshell dressed only in a black lace bra and pink panties worn under black sheer-to-the-waist pantyhose was taking selfies while lying on a couch. She moved into a bedroom and took more selfies with a man lying asleep on the bed behind her. They had obviously made love earlier. The parallel of her and Remy's current situation to the situation on TV was self-evident. A young girl dressed provocatively, uncomfortably close to a handsome older man. The difference being the man on the screen was asleep and Remy was wide awake. "I like her pantyhose." Remy pointed his beer can at the screen. "I like that they are sheer-to-the-waist but I prefer flesh-toned nylons," Tiffany croaked, her mouth was dry, she sipped more beer. "But they look good over those pink panties though," Remy countered. "I wear my panties over my pantyhose," Tiffany replied and immediately regretted saying it. It was an incongruous thing to say given the situation. "I know." Remy's hand alighted on her shoulder. "How do you know?" Tiffany whispered. "You keep showing me. I'm not sure if you're doing it on purpose but I like it," it was Remy's turn for his throat to be dry and scratchy. "I know you like it. I know you like to watch me in my swimsuit too." Tiffany took a final pull on her beer and put down the empty can on the table beside her. Remy followed suit. Remy's arm felt like a lead weight on her shoulder even though he was hardly touching her. She leaned in and put her head on his shoulder and Remy cradled her in his arm. They sat like that, neither of them saying anything, for what seemed like an eternity. Tiffany summoned up all her courage and turned her face to his, the sweetness of her breath was provocative to him. He turned to face her and gazed into her pretty green eyes and leaned in and kissed her softly on the lips. They kissed. Closed mouthed and tenderly. It was a beginning. Tiffany stroked Remy's cheek and he brushed her hair out of her eyes and then they kissed again. Tiffany felt Remy's eagerness and she opened her mouth a little and Remy slid just the tip of his tongue into her, she nervously put her tongue in his mouth too. It was her first French kiss and it was amazing. "This is so good," Tiffany gasped. "So good." Remy kissed her again, this time a little longer and a little harder. "I feel guilty about aunt Shelley," Tiffany whispered. "She's probably getting laid by some redneck right now. We have an open marriage," Remy lied. He wanted this sweet, virginal girl so much that he would say anything. Remy purporting an open marriage comforted Tiffany but she suspected the lie. Maybe they were open back when Shelley was on the road as a hippie for sure, but all Tiffany had witnessed since she'd been here was Shelley doting over Remy. The pang of guilt disappeared when Remy took her hand and put it inside his robe. She leaned into him and kissed him while her hand stroked his chest, she felt his muscled flesh through the matt of hair. Remy gasped as her fingers slowly moved down across his flat stomach. "I've never done anything like this," Tiffany murmured. "You don't have to anything you don't want to sweet-pea." Remy gazed into her eyes earnestly. Tiffany leaned in and kissed him, pressing her lips hard against his and driving her tongue into his mouth. She was kissing him with passion and enthusiasm, her tentativeness gone. Her hand grazed over the front of his briefs and she felt the heat and girth of his penis through the slinky material. "Oh Jesus," Remy gasped into her mouth. Tiffany lightly stroked Remy's penis through his shorts, feeling the heft of him, feeling the warmth, feeling it pulse. She was equipped the same way and she knew what she liked so she did it to Remy who was writhing on the couch loving it. Tiffany was getting uncomfortable. She was sitting awkwardly, having to turn sideways to kiss and fondle Remy. More importantly, her own penis was becoming erect and it was casing her some distress. "Just let me..." She disengaged briefly and Remy was more than a little disappointed. But when she stood up and unzipped her skirt and let it pool around her ankles he was overjoyed. He gazed at her long coltish legs encased in the sheer, shimmery nylons. He reached out and traced a finger up her thigh stopping at the juncture where her leg met her torso. He smoothed the tiny wrinkles in her nylons. Tiffany was shaking. She had stood to remove her skirt and gaff and had not expected Remy to touch her. But she loved it. It was the first time anyone had touched her this way and it felt wonderful. She continued to do what she had originally stood up to do and reached inside her panties and nylons and tore away the tape holding her penis between her legs. It sprang free, semi-erect. She eased it into place along her lower belly and pulled her pantyhose and panties tight to hold it there. She pushed down on her diaphragm and her testes descended. Tiffany looked down at Remy and saw that he was watching her intently. She lowered her head bashfully. She realised what she had done and what she was. "Do I disgust you? Is it awful?" A single tear ran down her cheek. Remy reached out and pulled her into his lap, she was sitting sideways and he nuzzled her neck and whispered in her ear. "On the contrary. You are fascinating. You are beautiful." He lifted her chin and kissed her. His hand went to her belly and stroked it, luxuriating in the feel of his fingers on her sheer pantyhose. His fingers continued their journey down to her pubis, slipping over her shiny satin panties. They found her fully erect and he slowly stroked her. "Oh my god!" Tiffany groaned. The feel of Remy's fingers gently caressing her through her panties was amazing; she had never felt anything so wonderful. She writhed and wriggled in Remy's lap as they kissed and caressed and then she became aware that his bathrobe was open and that his penis was pressing against her buttocks. It felt steely and powerful. It felt wonderful. Tiffany turned in his lap so that she was straddling him. They were now face to face and were able to kiss with wantonness and abandon. Tiffany was a quick learner and she was soon exploring Remy's mouth with her tongue. Now there was no mistaking the fact that Remy was grinding his cock against her ass. She lifted herself a little and reached inside his shorts and freed his erection and then sat back down and began to rock back and forth. For the trice that she had held the bare flesh of his phallus in her hand she had felt such a feeling of joy and wonder. She was aware that Remy was leaking against her panties, she could feel the wetness of his precum as he ground himself against her. She too was wet, her penis pressing against his belly through her underwear. The feel of the nylon and satin sliding against his hard flesh was scintillating. She kissed him again and he put his arms around her and held her close, grinding against her, kissing her forcefully, muffled whimpers of delight coming from his lips. That was when she felt something else. Something that would remain with her for the rest of her life. Power. She realised that anyone who saw what they were doing would be disgusted that a man in his forties was seducing a teenage transgendered person. The reality was the tables had turned as soon as she straddled him. She might be a novice but she was in control. She could tease this man all night or get him off in a trice. Or she could be a bitch and just get up and leave him hot and unsatisfied. But she had no intention of doing either. She liked what they were doing and she intended to use Remy to teach her. To guide her. She felt Remy's anxiousness to move on, to take their passion to new heights. He broke the kiss and eased her out of his lap. She furrowed her brow, confused and wondered if she was doing something wrong. What did he want? Remy took off his briefs, never taking his eyes of the beautiful young girl standing before him dressed only in pantyhose, panties, blouse and heels. Her erection was bulging the front of her panties and he couldn't help but reach out and squeeze it. He was rewarded with a gasp from those pretty red lips which he now intended to put to good use. Remy opened his robe and opened his legs wider and nodded to the space between them. A light went on in Tiffany's head as she realised what he wanted. She smiled seductively and got on her knees between his legs. She gazed at him, smiling wantonly as she took him in a firm grip and began to slowly stroke him. Remy threw back his head and groaned with pleasure. Tiffany took the opportunity to inspect his penis. It was long, sleek and veiny. The eye was leaking silvery threads of pre- ejaculate. It was not as big as hers but it looked slick and powerful. She wondered how it tasted. Tiffany was technically a virgin but she'd seen enough porn to know that there were many ways to give a man fellatio and now was her opportunity to practise. She lowered her mouth to his organ and tentatively lapped at it. Remy's precum was a little salty but otherwise tasteless. She lapped up every drop as it oozed from the eye of his glans. Then she ran her tongue along the girth of his penis listening to him whimper, hearing him beg her for release. She was in no hurry to give it to him. When he put his hands on her head and tried to force her down she didn't like it one bit. She shook her head and nipped at the tip of his penis. Remy got the message and removed his hands, content to let the pretty young girl between his legs take charge. Tiffany teased Remy. She endlessly ran her tongue along the shaft of his penis, over his glans and across his scrotum listening to him cry and whimper with pleasure and frustration. The feel of her tongue, sometimes featherlight, sometimes coarsely lapping at his genitals was exquisite. The way she lapped at his glans and tickled his fraenulum, teasing him with little jagged darts of intense pleasure was incredible. This virgin was a quick learner. Curiosity finally overcame her. Tiffany had always wondered what it would be like to take a cock in her mouth and she decided that now was the time to find out. She took all of him into her mouth and locked her lips around the base of his phallus and began to work her lips up and down his shaft, stopping at the glans to lick it and nip it gently. "Oh my god!" Remy roared. He instinctively put his hand back on her head and again she shook him off. "Of sorry but that is so wonderful," Remy gasped. She stopped what she was doing and looked up at him from between his legs. Remy looked down at her gorgeous face, pale in the light from the TV, framed by the shock of black hair. Those blood-red lips. Those magnificent green eyes. When she grinned at him she almost seemed malevolent, she seemed to be sneering. Tiffany smiled at him wickedly and lowered her face to his cock. Remy threw back his head and moaned as she earnestly worked on his penis. Tiffany slathered at it to get it lubricated and then worked her lips up and down the shaft, using her tongue on the bulbous head, swallowing the continuous flow of precum. Remy was writhing in his seat and almost sobbing. He called her name over and over. Tiffany sensed he was about to climax and she was as excited as he was. She reached into her underwear and took herself in hand. She worked her cock as she sucked and slathered Remy's quivering phallus. They were both close. Remy actually screamed when he climaxed. Tiffany felt his cock pulse and undulate in her mouth and then a torrent of hot salty semen filled her mouth. She swallowed the offering which triggered her own release. She orgasmed, muffling her groans on Remy's cock as the intensity of it washed over her. She slathered, sucked and lapped at Remy's cock, milking him of every drop of his semen. She liked the taste of it. The musky smell of ejaculate filled the air as her own issue splashed against the base of the couch and then spurted onto the cherrywood flooring. Tiffany wrung every drop of cum from her throbbing cock, the intensity of her orgasm magnified by the feelings of decadence and power as Remy came in her mouth. She sucked him dry, swallowing every drop of him and then lifted her head and smiled up at him. Remy smiled back at her, a look of contentment and joyfulness on his face. He lifted her into his lap and they kissed passionately. He could feel that her panties were damp and guessed that she too had orgasmed. They kissed and caressed until Tiffany became tired. She extricated herself from his embrace and got to her feet. "I'm tired and I'm going to bed." She pouted like a petulant child. Remy looked up at her, still fascinated and enraptured. He nodded at her, a look of utter content on his face. She leaned down and picked up her skirt. "Clean up my cum. Tomorrow you're going to teach me how to fuck," she said casually and then walked away, her heels clicking in the wooden floor. Remy was astonished and perplexed. Then he began to laugh. All the next day Remy pestered Tiffany in the store. Whenever Bric-a- Brac was devoid of customers he pawed at her but she pushed him away. He even suggested closing the store over lunchtime so they could have sex. "If we start doing anything different or suspicious people are going to notice," Tiffany didn't realise how fateful this statement would turn out to be until later. "You tell me you are in an open marriage which is fine. But people and particularly my aunt and my mother are not going to be impressed that you are having sex with your sixteen-year-old niece are they?" Tiffany berated him. Remy nodded wistfully. Tiffany was his Lolita and he was enraptured. "And just think how much more you are going to enjoy me when you finally get me into bed tonight." Tiffany smiled seductively. Tiffany left the shop early to prepare herself and Remy could hardly contain himself. He kept glancing at his watch but the time seemed to pass immeasurably slow. Tiffany locked the bathroom door behind her and took out her douche. She's douched before but this was the first time she had to do so because she was going to have sex with a man. She got the unpleasantness out of the way, showered, brushed her teeth and used mouthwash. She went back to her room and applied her makeup, very heavy and very sexy. She didn't bother to tuck, she just stepped into a pair of red satin panties and then pulled on a pair of very sheer black hold-up stockings. She knew that Remy liked black stockings and tonight she was dressing for him. She didn't bother with a bra either, she just put on a sheer black negligee, checked her makeup, brushed her hair, put on her jewellery and finally a pair of red high heel pumps. The red panties and heels contrasted nicely with the black stockings and negligee. Tiffany doused herself in perfume and lay on the bed and waited excitedly, her cock hard in her panties in anticipation. Remy closed and locked up the store right on closing time at 6pm. He quickly shaved, showered and brushed his teeth. He used mouthwash, deodorant and aftershave and almost pranced down the corridor to Tiffany's room, his erection leading the way. He burst through the door and Tiffany opened her arms invitingly and Remy fell on her. They kissed and fondled each other, rubbing cocks, grinding and groping. There was no tenderness; this was raw passion, this was lust. They were both so turned on and eager that they were impatient. "Let's forego the fellatio Remy, I want you to fuck me," Tiffany gasped. Remy got off her and tried to roll her over. "You can do me doggie any time you want to after this, but not now. This is my first time and I want to look at you, to see the expression on your face while you are fucking me," Tiffany insisted. She took off her panties and lay back down and put a pillow under the small of her back to raise her buttocks. She opened her arms and then her legs. "Come fuck me lover. Take my cherry," she whispered, her voice thick with lust. Remy took the lubricant off the bedside table and slathered his cock with the slippery gel and squeezed a gobbet on Tiffany's sphincter. She looked up at him, his penis rampant and glistening. He looked down at her and was so aroused, she lay there with that black hair, that dark eye makeup, luscious red lips, long stocking-sheathed legs wide open in anticipation. Remy slipped a finger inside Tiffany's anus and worked the lube deep inside her, being her first time he did not want to cause her any discomfort. "Come on," Tiffany said impatiently, grabbing his cock and pulling him towards her. "Ready?" Remy's cock trembled near her puckered sphincter. Tiffany nodded. Remy positioned his rock-hard penis at the entrance to Tiffany's anus and then ever so slowly pierced her sphincter. Tiffany gasped and grimaced. It hurt, as she expected it would. She knew from what the research she had done online that if she could tolerate the pain until Remy was fully inside her, her anus would become dilated and she would start to feel pleasure. Remy had his glans inside Tiffany's sphincter but was reluctant to thrust any deeper because he believed he was causing her pain. "Come on Remy, fuck me!" she goaded him. She wrapped her legs around him and thrust upwards, ever so slowly skewering herself on his cock. She grimaced and gasped the whole time but she was already starting to feel ripples of pleasure from her sphincter and the feeling of being full of cock was incredible Tiffany put her arms around Remy's neck and pulled his face to hers. "Nice. Lovely," she whispered and kissed him deeply. Remy began to deliberately fuck Tiffany using long leisurely thrusts. Tiffany whimpered underneath him, feelings of intense pleasure radiated from her sphincter and when Remy drove deep inside her his cock pressed on her prostate gland which emitted waves of pure gratification. Remy kissed her hard and she responded, raking her nails on his back and shoulders and squeezing him with her thighs. Her tight anus clung to Remy's cock, contracting it as he fucked her. He was close to coming but he wanted to wait for Tiffany. The feel of her stocking- clad thighs against his sensitive skin was delightful. Tiffany encouraged Remy to fuck her harder, her excitement was intensifying and she could feel an orgasm building deep inside her. The feel of Remy's cock buried deep in her anus combined with her cock rubbing on his stomach was going to tip her over the edge. "Fuck me Remy! Take me! Make me come!" she gasped. "Oh Tiff! I'm coming," Remy hissed. He held her down on the bed and jackhammered his cock in and out of tight anus. Tiffany squealed as she came. The most intense orgasm of her life surged through her body. Her cock convulsed, spewing scalding semen whilst concurrently her anus throbbed, her sphincter spasmed and her prostate throbbed. She beat her fists against Remy's chest and drummed her heels on his back. Remy pushed his cock all the way inside Tiffany and ejaculated, her tight anus expressing every scintilla of semen from his quivering cock. He held her down on the bed as she thrashed writhed beneath him until she was sated. Tiffany was finally spent and exhausted, she lat still as Remy kissed her softly, his cock still inside her slowly contracting, she felt his spend dribbling out of her anus. She returned his kisses and stroked his cheek lovingly, keeping her legs wrapped around him to hold him close. "That was wonderful." She kissed him tenderly. "It was amazing." Remy grinned down at her. He could feel her semen, sticky between their bellies. "Can we do it again later," Tiffany said coyly. "Of course when can. As soon as I recover," Remy grinned. "I'll let you do it to me every day if you are nice to me," Tiffany teased. And so it came to be that Remy and Tiffany entered into a fiery love affair that lasted nearly three weeks. She was a good student when it came to both cards and sex. She was soon beating him occasionally at cards and teaching him new sexual techniques as she became more adept and self aware. They were both insatiable, during the day Remy would lock the door to the shop and pull the blinds and bend her over the counter and fuck her. They would spend all night in her bed making love. She learned how to control her sphincter muscles and would sit astride him, impaled on his cock, not moving; edging him until he begged for her to grant him release. When Shelley came back from her road trip Remy and Tiffany found they couldn't stop. Remy was infatuated with Tiffany. She was his teenage dream-girl. Tiffany liked Remy but not in the same way. To her sex with him was just a side benefit of living with her aunt and uncle, he was an attentive lover and doted on her. Shelley soon became suspicious of them; the way they acted around each other, their furtive glances and gestures. One morning she told Remy that she had a doctor's appointment and would be gone for three hours. He offered to drive her but she said it was fine, it was just a routine test for a woman her age. Shelley snuck back home an hour after she left and found the store locked and shuttered. She unlocked the door to Bric-a-Brac and found her life partner with his cock buried up to the hilt in her niece's behind. After the tantrums, recriminations, allegations, and counter- allegations, Shelley accepted Remy's side of the story. Remy had been duped and seduced by the little vixen transsexual. Tiffany was to blame. She was a Lolita. The fact that Remy was forty years old and Tiffany was only sixteen seemed to be lost on Shelley. Shelley kicked Tiffany out of the house, exactly as Tiffany's father had done. This time Tiffany was better prepared. She had some life skills that she didn't have the last time she was kicked to the curb and she had a little money she had made working in the store. Tiffany tossed a coin, heads LA, tails New York. It came up heads. She took a bus to Los Angeles instead of an airplane because it was cheaper and she was in no rush to get there. Raffe Ignesman spotted Tiffany Robinson as soon as she alighted from the bus. Most of the passengers had travelled in tracksuits, jeans or some other kind of comfortable clothing. Tiffany had changed her clothes at the last stop because she wanted to arrive in LA looking and feeling good. She was wearing a short denim skirt and matching jacket under which she wore a red satin blouse. She was wearing full makeup, nylons and red high heels. Tiffany looked around with awe at the busy bus station which was noisy and dirty. She didn't care. She was in the big-smoke now and as far as she was concerned the world was her oyster. Raffe was delighted with the spectacular young creature standing next to the bus looking lost and alone. She was undoubtedly pretty. She was downright gorgeous in fact; and young, and sexy, and obviously bewildered. As he got closer to her he guessed that she was trans. Even though she was very feminine there were tells that guys in Raffe's line of work knew by heart. She would still be a wonderful addition to his stable. Tiffany had two suitcases which was going to be awkward for her. She took them both in hand and turned around and ran smack into Raffe. "I'm sorry doll. Here, let me help you with those," Raffe gave her his best smile. Although he was young and handsome Tiffany thought he smiled like a wolf. He was rake thin and wore an expensive suit and shoes. She guessed that the Philippe Patek on his wrist was worth at least two grand. Tiffany immediately figured out what Raffe was up to, but she did not let on that she knew. "Can I give you a lift somewhere?" Raffe opened his hands as if to indicate that he was harmless; which was the opposite of what he was. "I'm going to the Central Hotel and Boarding House, downtown," Tiffany replied. "I can do that." Raffe smiled again. "I'm Raffe Ignesman by the way." He offered his hand. "I'm Tiffany Robinson or Tiff if you like." She shook his hand. The Central Hotel and Boarding House was a cheap flophouse used by waifs and wanderers when they first came to LA and Raffe had picked up more than his fair share of prospects for his stable from there. Raffe drove a white Chrysler LeBaron just like in the song. He wheeled one suitcase and she the other. Tiffany was also loaded down with a travel bag and a handbag. Raffe hefted her suitcases and travel bag into the trunk and she took her handbag into the front seat with her. As they exited the parking lot Raffe began a rehearsed speech. "What you in town for sweet-pea? How long you staying?" He glanced at her. Traffic was busy so the ride was going to take a while, which suited him. "I've been thrown out of home so I've come to LA to try to find a job and hopefully a future," Tiffany gave him an innocent smile. "Wow! Too bad. And you are so young too." Raffe sympathised with her. "Doesn't help that I'm transgender and haven't yet started hormones or had any surgery. And I'm only sixteen, so you know..." Her voice trailed off. Tiffany was playing Raffe just as he was playing her. "That is so sad honey. I just wish there was something I could do to help." The sharklike grin returned to his face. "Well there is Raffe," Tiffany had allowed her skirt to creep up her thighs and Raffe's eyes wandered to her legs, then to the road then back to her legs. "I'm so glad that you are going to let me help." Raffe did his best to sound sincere. "What is it I can do?" he asked the fifty-four thousand dollar question. "Well when I start working for you as a prostitute I don't want to work on the streets. I don't want you to be violent with me. I don't want to get hooked on drugs, and I want a fair share of what I make for you," Tiffany said straightforwardly. Raffe almost left the road he was so shocked. "What did you think? You were going to woo me, seduce me, promise me the world and then throw me out on the street working for you as a hooker?" Tiffany said casually. "How old are you really?" Raffe frowned. The pleasantness had gone from his voice. "I'm sixteen going on seventeen but I'm learned a lot the last few months. It's hardened me. I've been used and I've been discarded and I'm not going to let that happen again." She too spoke plainly. "You any good?" Raffe nodded at her crotch. "My uncle seems to think so," Tiffany quipped. "Jesus! Your uncle?" Raffe swerved the car again in reaction to her answer. "Look. Let's cut the bullshit. Take me back to your place or a hotel, somewhere decent, and let me show you what I can do," Tiffany smiled at him and placed a hand on his shoulder. "Jesus," Raffe sighed. "Ok little girl. Let's go to my place and try you out." Raffe smiled as he stared at the road through the windshield; he liked 'em young. "We won't unpack. If you ain't as good as you say you are you can find your own way to your hotel. If you are as good as you say are I might even spring a room for you here. Of course it goes on the tab." Raffe offered her his wolfish grin again. They had driven into the underground parking garage of a swank apartment building. Raffe led her to the elevator and waved his passkey to take it to the penthouse floor. Tiffany didn't get to see much of his apartment because he led her straight to his bedroom. He put down a towel and pushed her down on his massive bed. "We'll take the foreplay as wrote, you can begin by sucking my dick," Raffe chuckled, stripping out of his clothes. Tiffany opened her mouth and took Raffe's long thin cock into her mouth and went to work. She applied all of the oral skills that Remy had taught her and some she had invented herself. She fellated Raffe slowly at first, building up speed until she was sucking his cock with gusto. When he was close to coming he pushed her off him. "Not bad sugar, now let's get you undressed and see what else you've got offer," he helped her out of her jacket and unbuttoned her blouse and she took it off. He unhooked her bra. "You really need some tits honey." He inspected her flawless white skin like she was a farm animal for sale. Tiffany lay back and Raffe pulled down her skirt and threw it in on the floor. "I'll say one thing, you got a great ass and those legs just go on forever," he stroked her thighs and worked his hands down as far as her ankles and then opened her legs. He removed her panties and freed her cock. "Wow that's big! A lot of guys like trannies with big dicks, that's another asset," he said as he stroked Tiffany to full tumescence. He took a tube of lubricant from the top drawer of the bedside table. "I'm not really prepared," Tiffany said sheepishly. "Oh come on now. I'm not gonna let that stop me." Raffe viciously ripped out the crotch of her pantyhose. He plunged his cock into her tight anus and Tiffany smiled up at him despite the pain. She gripped his hips and began to fuck him. He rolled her over and pulled her to her knees and continued. She squirmed for him and used her anal muscles to squeeze his cock as he fucked her. "Jesus you are good," Raffe grunted. "Play with yourself sugar, I wanna see that thing spurt," Raffe said as he gripped her thighs and began to plough her. She willingly obliged. This was the first time she had been used roughly and she found that she quite liked it. Tiffany orgasmed with him when Raffe pulled her back hard against him and ejaculated deep inside her. Once he had finished he released her and pulled his cock from Tiffany's dripping anus and wiped it on her ass. Tiffany fell forward on the bed, sore but satisfied. Raffe came back from the ensuite bathroom with a wet cloth and had her clean herself. He made her strip naked and parade in front of him. "The good news is I can use you. You're young, sweet and know how to fuck. I'd say that blowjob was as good as any I've ever had," Raffe said sitting on the edge of the bed, now dressed in a silk robe. "The bad news is, is that even though you are exceptionally beautiful and have a great ass and legs; you need some feminine curves and tits," he continued to prod and poke at her. "I have my own doctor who looks after my girls. I'll get him to start you on hormones and get you booked into a hospital he uses down in Mexico to get you a nice big set of titties." He walked over to the wet bar and poured them both a drink. He threw her a robe similar to his and beckoned her to come sit with him in the lounge. "Put your panties on sweet-cheeks, this lounge is white leather and I don't want it stained," Raffe snickered. He handed her a drink and lit a cigarette. He offered her one and she took it. "I'm not gonna put you on the streets, you are way too valuable an asset for me to do that. You are going into my stable as a callgirl for my well-paying clientele." Raffe spoke to her like she was his chattel. "What's the deal?" Tiffany asked sipping her drink. "Fifty-fifty straight up. But you pay me for the hormones and the tits, plus you pay rent, ok?" he said. "You will be a specialty. There's guys out there who will pay big bucks for a night with a special girl like you with your talents," Raffe explained. "Sounds too good to be true," Tiffany pulled up her legs up and folded her arms around them. "It is. I don't usually give my girls deals like this. But you are special and we can both make a lot of money. I have interests in other businesses." Raffe gave her his wolf-grin again. "Can I think about it?" Tiffany said wistfully. "Yeah. You can. You have until the door hits you in the ass to make up your mind." Raffe got up to indicate the meeting was adjourned. "I'm in," Tiffany said with determination. "Ok then, lets seal it with a kiss. I haven't tried your kissing skills yet," Raffe pulled her up off the lounge and kissed her. He kissed her long and hard and then started to ease her back towards the bedroom, still kissing her. "Let's fuck a little more and then we can sort out the finer points of our deal," Raffe said through crushed lips. The next twenty years of Tiffany's life was ordained that very day. Raffe settled her into an apartment and had his doctor come see her. The doctor gave her a complete physical and provided her with female hormones and gave her instructions on how to use them. Tiffany and Raffe argued about the size of the breasts she was about to receive. Raffe wanted 40-DDs so she would have huge tits on her lean frame but Tiffany argued against it. Her selling point would be that she was young and girly; putting huge tits on her would spoil that. They compromised on 38-Cs and Tiffany had the surgery. Raffe gave her a week to recover and put her to work. Tiffany was hugely popular and was constantly in demand. She soon developed a string of clientele who repeatedly demanded her services. Some offered to take her away from her life as a prostitute, they fell in love with her. Tiffany knew that they were fantasising about a life that could never be, but she milked her clients for whatever she could get from them. Raffe finally admitted to Tiffany that he really wanted her to get the huge DDs so he could put her into porn. Tiffany argued that a sweet young thing with a huge cock like hers would be very popular anyway. They met with a man named Lyle Brinkman, who used the pseudonym Devon Devine, owner of Xavier Productions. Xavier Productions was a pornography business producing magazines and DVDs and was venturing into online video streaming sales. Raffe negotiated a good deal for her. She would be paid four thousand dollars per movie, five thousand for the stuff involving bondage and discipline, degradation and pissing, which was becoming more popular. She churned out an average of one movie per week and she never turned down a role. She worked in 'man fucks tranny' movies, 'tranny fucks woman' movies, and 'tranny fucks tranny' movies and tolerated doing the more degrading stuff for the extra cash. She wouldn't fuck men though, she just couldn't do it. She gave Raffe fifty precent of everything she earned and she eventually trusted Raffe enough to let him invest her money. Although he was her pimp they became more like partners and occasional lovers. He invested her money wisely and bought a condo for her in Lake Tahoe which she rented out to cover the corporate-body fess. The condo was almost paying for itself. Tiffany still had her fascination with cards and practiced her moves every chance she got. On the rare occasions that she took vacations she went to Las Vegas or Reno and practiced counting cards and carefully watched the dealers and the pit bosses. Raffe pulled a few strings and she got her gaming licence. She was surprised when a casino offered her a short stint as a dealer. It was a small casino and it was cashing in on her celebrity by advertising that they had a famous porn dealing on the tables. Tiffany loved the thrill of working in the casino but it didn't pay her enough. It was merely a diversion a few times a year. As Tiffany got older she began to work less. She was still stunning but she was no longer as popular on Raffe's online dating site as the younger girls. It didn't matter, she had a steady income from her regular customers, all wealthy men. She sometimes, but rarely, took on a high-roller in a casino on as client but only if she liked him. This was a bonus to her as far as she was concerned and she didn't split the fee with Raffe. The porn business was slowing down too. Lyle wanted younger actresses, the younger the better, for his movies and Raffe was supplying them. Young girls that he conned or bullied into a life of prostitution and pornography. What Tiffany didn't know was that Raffe was selling some of the girls on the dark web. The dark web is a secret part of the Internet that has a few special websites that can only be accessed through certain gateways by certain people who know how to get there. It's a place where you can buy anything from drugs, to weapons, to stolen goods and even people. Wealthy Russian, Indian, and Arab men in particular liked young, light-skinned, American girls. Tiffany had been in a few movies with Tina, Lyle's common-law wife, who was also a transsexual woman. They clicked both on and off screen. They had a torrid love affair which eventually tapered off to become friendship, although they still liked a roll in the hay together when the mood took them. Tina was Tiffany's only close friend other than Raffe. Tiffany had grown up hard. Selling her body had toughened her and she saw the worst and sometimes the best in people. She didn't feel sorry for herself, she was pragmatic. This was the life she had chosen. By then she had a decent nut in the bank she could have got out at any time, but the truth was she loved her life. Then it all came crashing down. Raffe was selling two young girls to two Russian gangsters but one of the girls was the step-daughter of the wealthy construction mogul, Steve Patterson, who had hired a guy named Randy Carter to rescue her. Randy enlisted the help of his sister-in- law, Sarah Carter. At the handover to the Russians there was gunplay. No one got killed but Sarah Carter got wounded. The girls got free and Raffe had to go into hiding. The Russian mob found him and executed him. This meant Tiffany was out on her own, but by now she had the skills to look after herself. Although Lyle and Tina Brinkman were not intimately associated with Raffe Ignesman's business of selling girls online, they were guilty by association, possible accomplices. Both the Russians and the FBI were looking for them. Lyle and Tina disappeared, some said to Mexico, some said to Europe. They did manage to transfer all of the money out of their business and private accounts, so wherever they were, they were living the highlife. So all those years later when Stephen Bateman said to Tiffany in that Lake Tahoe hotel where they had just made love: "I actually have a business proposition for you." "Have you ever heard of Lyle and Tina Brinkman?" You can fully understand why Tiffany paled with shock and was speechless. To be continued.