2 comments/ 32114 views/ 7 favorites The Odyssey By: Intercontinental This is a true story. As a result, the composition favours fact, over the conventions of a normal erotic tale. I dedicate it to every cross – dresser, who wonders where it might all lead to, and particularly those who have fantasised about being fucked. This is my story of turning fantasy into reality: Len had wrestled with his cross- dressing for years, unsure of his sexuality, yet certain of the uncertain journey of his transvestism. Like many, it had started with that inexplicable urge to slip on some of his mother's underwear. That was when it had happened. That familiar smell, and comfort, of his mother's unmistakeable aroma, combined with the unfamiliar but indescribably exhilarating sensation of female materials and styles. He was hooked. He was a tranny. And so it progressed ,in fits and starts. As he grew up he started to buy his own clothes. Firstly, those tentative steps into specialist lingerie shops. Then as his confidence, and urge grew, full scale buying expeditions in department stores, top clothes, shoes, accessories, jewellery. But it was never enough, each purchase required another. And each step provided an exquisite thrill. With a wardrobe full of women's wear, the urge to go out became irresistible. It had started with a smart jersey dress, court shoes, stockings , bra, panties and suspender belt, simply stepping out into the garden. The joy of the soft material swathing his skin, and the cool night air swirling around his hosiery clad legs heavenly. He knew that he had to repeat this, but was not going to be condemned to furtive night time dashes around his garden and to the post box, but he needed some help to take him further. That help was provided by Krystyna's dressing service. Professional make –up, a proper wig, and silicone breasts provided that quantum leap. From bedroom dresser - to girl about town. From Len to Lucy. Krystyna had insisted that she take a femme name. Now she could walk about, shop, and relax without anyone paying her undue attention. She could pass. And as her visits to Krystyna increased, so did her confidence. She could do her own make –up and hair, and was socialising with other T girls in the T bars and clubs around Manchester. But still she knew there was more, but was not quite sure what the "more" was. Until one day when she was enjoying a coffee with Krystna, and she spoke: "Lucy, you have come a long way since I first saw you. You look convincing, and behave like a woman, and your dress sense is just right for a woman of your age. But have you ever wondered why women, and you, dress, the way they do? Smooth legs and armpits, no body hair, high heels perking up the backside, immaculate make up, a skirt with a split which flashes momentarily a bit more leg than is perhaps decent, a blouse with material that when occasionally pulled taut, reveals the outline of that pretty bra and heady perfume. It's to be attractive to men, Lucy. It's to pull men, and get them to fuck you." Lucy reeled in shock. It was as if a blind man could see. She had never thought of herself as "gay" before, but all of a sudden it made sense. First she had wanted the clothing sensations of a woman, then she wanted to dress like a woman, then she wanted to go out like a woman, then to assume a woman's name and identity, then to behave and inter act as a woman, but where was it all heading? All of a sudden it made sense, it was to be fucked like a woman. That was the great divide. How could you be like them if you had never been seduced? Never been excited by the sight of an erect cock? Never given a man womanly satisfaction? Never giggled with your girlfriends about your bedroom antics? And so she started to trawl the private ads, the seedy underworld of off-beat sex. After numerous false starts she started to regularly chat on an internet messaging service. His name was Rob. He looked nice. He lived alone, he was ten years older than her, and was looking for a T girlfriend. They agreed to meet. Ostensibly it was just to get acquainted, but it was implicit that if they hit if off it could be more. As Lucy sank into the bath that late afternoon, she became aware that something was happening to her, or maybe it had happened. The perfumed soapy suds lapped around her. She checked for errant body hair for the umpteenth time, gliding the razor over her already smooth armpits, on the lookout for the faintest hint of a wisp of a hair on her legs. She smoothed the lather all over her body, whilst peeking her painted toenails and fingernails out of the water, seeking out every crevice. Excited, but a little afraid that she was preparing herself for someone else. To be admired, enjoyed, appreciated, fucked and violated. Damping the moisture on her rapidly drying body she surveyed the clothes she had previously prepared on the bed. Her skin was still tingling from the hot bath water. The pink t shirt bra with moulded cups was perfect. It offered a lovely shape to her silicone forms under the sleeveless black top. The little bows on the spaghetti straps and lace back band oozed femininity. The matching hi-leg panties were just right. She thought of going matching black under the top, but the colour didn't show through and she thought that pink panties were a nice surprise; sexy, girly and colourful. Her still moist fingers struggled with the cellophane, slipping slightly on the packet of 10 denier matt nude hold up stockings. The gossamer soft material offered a discreet and pleasing appearance, the matt finish giving a, "is she / isn't she" look, obviously it had to be stockings, as she fully intended to be screwed wearing them. A short grey print skirt with kick split completed the ensemble. Applying her make-up she smiled at the paradox of the actor preparing for the performance. But this was no performance, it was for real. Smooth foundation, a hint of grey eye shadow, mascara and lush pink lips, plumped and glossed to deliver the blow job they craved giving. Even the jewellery had to be carefully selected. A ring to give some extra glitz to her fingers. Chunky necklace to occupy a plunging neckline, stud earrings that were not going to shake around too much, and loose bracelets to give a delicate rattle as her fingers worked up and down on that hot cock. These things matter! A final squirt of perfume and she was "good to go". As she left the house she stepped into her black high heeled courts, the transformation was complete. She WAS Lucy. Stepping up to the front door was a strange experience. Feminine, female, confident, vulnerable, sexy, hot. Rob casually answered the door. "You look gorgeous" he complimented. He was taller than she had imagined and casually dressed, she asked to visit the bathroom first to freshen up. She glanced into the mirror, checking her lipstick and straightening her skirt ready for what was next, then walked though to the lounge, and sat down next to him on the settee. Far closer than she would ever have normally sat next to a man. It felt very daring. As they exchanged small talk Lucy extended her left leg, exposing the sheer, smooth flesh. The hem of her skirt sat just above her knee. But neither of them were there for small talk. Rob leaned across, putting his right arm across Lucy's shoulders, pulling her towards him and kissed her. It was a simple act. But it changed everything. Lucy's emotions swirled as she returned his kisses, his tongue invading her mouth as vigorously as his cock would surely invade her body later on. Their tongues swished and weaved sending her libido into over drive. As her palm moved to touch Robs face so she was aware of his palm, settling between her thighs, and moving north! Her first snog, then her first goosing ,all in seconds. His hand moved up, past the fine stocking material, past the sturdier lace tops, on to the soft fleshy inner thigh before hooking his fingers under the flimsy elasticated gusset to probe her virgin entrance. Lucy kissed Rob more urgently, then passionately necked with him as his fingers caressed and probed. She was being worked like a puppet, and as she leaned across to offer him better access her hand fell on his lap, and the unmistakeable outline of a big swollen, cock. Instinctively, she knew what to do. Her fingers tore at the buttons on his shirt revealing a heaving, hairy chest, she then moved lower yanking down the waistband of his trousers to unleash a swaying pole of tumescent joy. There was really no hesitation. This is what girls do. She steadied the cock with the fingers of her right hand and then sank her eager lips onto the engorged helmet like a an eagle swooping on its prey. Rob let out a throaty cry as she got to work, licking, slurping, sucking and kneading as Rob manipulated her, his cock down her throat, and two fingers up her ass. Lucy wondered what some women didn't like about it as she enthusiastically went about her task, settling into a nice bobbing motion with her mouth and light wanking action with her fingers on the upstroke. Her bracelets chimed to her movements. Rob's shaft was now coated from top to bottom with her saliva as it slipped around in her mouth, which was just as well , if he was going to use that love monster as she hoped he would. Then he shifted his body: "Let me take you to the bedroom" Rob purred into her ear. Lucy was unsure whether this was a request, a question, or a command. She did not verbally answer. She just stood up, straightened her skirt, and took his outstretched hand as he led her out. It felt almost child like. She was trusting, he was in control. He wanted it, and she was going to give it to him. She felt as meek as a lamb being taken to the slaughter. As she stood facing the bed he started nuzzling her neck. "Put your feet further apart, there's a good girl ," he whispered. As he continued to nuzzle her neck, she felt both of his hands grab the hem of her skirt and lift it up. "Whoa, Lucy, pink panties" "Do you like them?" "I'd prefer them a little lower down" And with that he rolled the waist of the panties down to crotch level, she then felt the warm slippery head of his cock as he pressed it between her ass cheeks. She squirmed, pressing back, delighting at the feel as it slithered between her legs, turning her head around she kissed Rob's lips. The expectation was becoming unbearable as he teased her, prodding around without doing the deed. "Rob, please put it in me" she pleaded. "Move over there then, lean forwards, legs apart and put your hands on the wall ," he ordered. Instantly, she complied, knowing that they were moving to the "business" stage. She could hardly believe how easy it was to play the part. This was not make believe. This was for real, ready and prepared for cock action. Arms braced against the wall, legs taut and butt raised by the heels, skirt rucked up around her waist, and panties yanked slightly down sitting around her stocking tops. "Oh, please fuck me, Rob. Please give it to me, make me a woman, make me your woman," she begged. She could feel him guiding the head to her entrance, he was rock hard. Then he moved his hands to grip the fronts of her thighs. "If you want it Lucy, I am happy to oblige" "For fucks sake Rob, just do me, screw the ass of me" "You dirty little slut" sneered Rob as he drove his cock meat all the way in using one stroke. Her body short-circuited on emotions, pain, excitement, shock, pleasure and relief. She marvelled at the way she had taken it all, every inch of his manhood. She let out a little moan, as he took up staccato thrusting motions, then began to relax, and backed up to take his thrusts. Suddenly, she started as she heard, and felt, the slap of his hand across her right ass cheek. "Come on, you bitch, you're loving this, aren't you?" he taunted, as she bucked in rhythm with his thrusts. She was shocked, she was being fucked AND spanked, but somehow it was alright. She was pleasuring her man, and if he felt like urging her on a bit, well that was his prerogative wasn't it? The anonymity of staring at a blank wall, while her man had his way with her was, oddly, an aphrodisiac. She was his woman, his lover, his slut, his plaything, all at once. She wallowed in the impersonal air of being used, being taken, being banged. But that was soon to change. He withdrew, then pushed her onto the bed. "On your back Lucy, I want to look at you as I fuck you." Rob stripped naked, Lucy lay there, ready to be taken again. "Hitch up your skirt you little slut" Obediently, Lucy pulled up her skirt, her pink panties still down to her crotch. Rob leaned forwards and yanked them off. Lucy's senses reeled again as she realised what it meant to be dominated, taken and to be at the mercy of your lover. Rob kneeled in front of her on the bed and then pulled her hips up onto his lap. Her legs draped helplessly either side of his body. Carefully, he inserted his cock into her again. Far more comfortable, and relaxed, Lucy lay back, longing to be used, and abused. Rob, leaned forwards, and started to bang her. As he got going, she began to enjoy it, her ass skewered and pumped, her hips slid up to take his length with increasing urgency, at last she began to understand what it meant to be a real woman. The whole length of her body shuddered as she took each stroke, and with each stroke she wanted to draw him in more tightly. Kicking off her shoes she crossed her legs behind the small of his back. She could feel his cock swelling inside her. She stretched her arms forwards, touching first his hips as they muscled into her, then his hairy chest, then she tweaked his nipples sending him into a mini spasm of joy. This was it wasn't it? Giving pleasure, being loved, giving love, being taken. She looked into his eyes as he fucked her, a glazed mixture of desire and love. He was hers, and she was his. But love was giving way to lust: "Fuck me you bastard" she taunted. "That's it, make me your bitch, I want to feel your cum inside me. I want to be your cum soaked whore." "Ok bitch, you want it? You'll get it," he snarled. To her shock, and amazement, Rob stood up, lifting her hips as he went and forced her onto her shoulders, then, pushing his cock into her once again he took up a frenzied, jackhammer, pace on her. Her whole body shuddered as he battered into her. She was like a floppy doll, wholly at his mercy. She felt, and was helpless as he drove into her. Then his thrusts became more determined and she could feel his cock swelling inside her. "My God, he's going to come. He's going to come inside me," she thought. A strangled cry from her lover coincided with what seemed like an explosion of cum, hosing her insides. Rob collapsed on her, exhausted by his efforts, Lucy lay there, bedraggled, pummelled, but strangely contented. She had done it. She was a woman now. And she knew that there could be no turning back. She was now Rob's girl. Lucy walked back to her car along the busy street, her mind a muddle of emotions, totally unselfconsciously. She mingled with other women, who did not give her a second glance. She smiled inwardly as she felt a little trickle of cum slip back out into her pretty pink panties. Glancing around she looked at the faces of other women around, and wondered how many of them had been fucked that day, how many lips had tasted cock, how many fingers had struggled to contain a swelling erection? Well she had, and now she too could join the exclusive club of Girls Talk. That secret world where women shared their most intimate experiences. She was no longer looking for something else, the next thrill, that journey was over. She had arrived at her destination. Her place was not simply to look like a woman, but to be a woman. To make love and give satisfaction as a woman. She had promised to ring Rob the next day, and wondered what her next adventures as Robs girlfriend would bring? Well that's for another time............... The Odyssey Ch. 02 Lucy sat, staring into the computer screen. It had been three weeks since she had met Rob, since he had made a woman out of her. And since then, everything had changed. Before it had been enough to dress. To go out, perhaps to a T club and socialise, or to drive into town and shop. She had quickly learned to find her style, and blend. Sensible smart skirts, neat jackets and discreet make-up and kitten heels made her indistinguishable from the mighty mass of womanhood that was out there. Apart from one niggling thing. Most of them were getting cock on a regular basis, and she wasn't. As her confidence had grown, so the everyday normalities of life had become more......................well, everyday. And her solo T existence had become more mundane. Enjoyable of course, but incomplete. The realisation dawned upon her that simply dressing, behaving, and convincing as a woman was not enough. That to be a woman she needed to explore what it was like to be with men. For how was it possible to have proper girl talk, if she hadn't experienced the nuances and foibles of life as a woman dating men? Yes, the ephemeral pleasantries of exchanges with shop assistants and restaurant staff were nice. But it wasn't enough. Who wants to be limited to swapping compliments with girlfriends about shoes, when you really want to be able to discuss how your boyfriend' s cock almost made you pass out with pleasure the night before? His profile had stood out. Phil, mature, mid 50's, rugged good looks, fit and dominant by nature, looking for no strings fun. They swapped emails, then telephone numbers. Then they arranged to meet, a car park at a country pub near Albrighton, what was going to happen after that was left unspoken. But Lucy wanted it, and liked it, that way. The idea that she was going somewhere to meet someone whom she didn't really know, but whom she was going to surrender herself to, excited her. And she could not wait until the day came around. His instructions had been quite explicit. High heels, stockings, short skirt, white blouse and lacy black underwear, with bold make-up, as if going to a night club. The first law of girls going out is that it always takes longer to prepare than you think it is. What looked like a comfortable three hours soon started to vanish with frightening speed. Leg, under arm and pubic shaves always seemed to miss one straggling hair, one eye lash seemed always to be carrying just a shade too much mascara, a few millimetres of lipstick line was not quite straight enough. And then there were the perfectly manicured artificial finger nails, beautiful to look at, but hell to put on right. What looked like a comfortable half eight meet, now looked like an eight forty five meet at the earliest as she made her way through the unexpectedly busy early evening traffic. Then the texts started to arrive. He had arrived. Where was she? Why was she late? Lucy frantically text back, explaining her predicament and that she was on her way. Half of her was pleased that he was there, the other half was apprehensive about what her tardiness might mean. She turned into the pub car park and instantly spotted his car, he too had noticed her and turned his headlights on and off. Parked next to him, he got out of the car. She couldn't help but notice how lean he looked. As he got into the passenger seat of her car she quickly checked her make up in the mirror as the courtesy light flashed on, then off. "So we meet at last. Better late than never," he spat. Lucy started to mutter some apologies but the words were trapped as he leaned across and clamped his mouth firmly over hers, his tongue lewdly probed between her lips and into her mouth, there was no doubt who was in charge here. "Drive," he ordered. With some trepidation she followed his instructions until they arrived at a remote spot down a country lane. Pulling off the road, Lucy turned off the ignition and turned towards him. Suddenly her skirt seemed to be showing far too much leg and she tried to make out his facial expression as he leered at her in the darkness. "Get out of the car" he commanded. Anxiously, she obeyed as he beckoned her over to the passenger side of the car. Standing behind her he told her to put her hands on the roof of the car. "Now spread your legs, bitch. When you are on a date with me you don't keep me waiting. You probably think you are something special, don't you? Some sort of cock tease. Well you are not, you are just a cheap slut cruising for cock. And you, lady, need to be taught some manners." And with that she felt his hand smack against her buttocks three times. The shock pulsed through her body. Here she was, with a man she hardly knew, out in the middle of nowhere, and he was spanking her for being late! "Lift your skirt so I can see your panties, nice, now slip them down just enough to show me your cheeks, now I'm going to teach you a lesson you will not forget" And with that he started to rain blows with the palm of his hand on each of her buttocks in turn. She flinched as each rasping smack rippled through her flesh. She could feel her cheeks redden, and them tenderise, as he kept going. Ten, twelve, fifteen, twenty, she was beginning to lose count. She had never been so humiliated in all her life, but then, slowly, the humiliation gave way to excitement. Sexual excitement. It had been her fault that she had arrived late. She should have started to get ready earlier. But instead of just saying sorry. As Lucy she had another role to play, as a woman whose aim was to please her man, and she had actually displeased him. She deserved this and he deserved his pleasure. Then he stopped. "Pull up your panties and get back in the car" She could only murmur a mumbled thanks as she eased her silky panties up over her smarting buttocks, the cool material providing some balm to the savage assault they had just endured. Quickly she wriggled her skirt down to offer some modesty as she returned around the car to sit down inside. "You're a cheap whore, aren't you Lucy? Well come on then, show me your slutty tricks. Because at the moment you have a lot of ground to make up if you want to ever see me again" Lucy leaned over and kissed him, her right hand resting on his upper right thigh, he started to respond and grabbed her face with his left hand pulling her towards him. She slipped her fingers a little further up his thigh and found his bulging cock. Inside she swooned. She had done this. She had caused his cock to swell with spunk, she had him wanting her, and she wasn't going to disappoint him. Instinctively, she knew what he wanted, as she moved to his waistband, unbuttoned and unzipped, and let his pulsing cock bounce out of its denim confines. His pubic hair was shaved, and his cock meat smelt of soap, and the dusky scent of sex. Lightly she traced her fingers along its length, letting her nails trace a light furrow. "Oh, that's better" Phil sighed as she started to set up a rhythm. His head tilted back onto the headrest as she got to work, offering a magic just as exquisite with her own fingers on his cock, as the palm of his hand had done on her buttocks. And for a moment she was in control. Each change of pace, or variation of intensity of stroke instantly registering on his face as she pleasured him. "Stop looking so pleased with yourself slut, you think that's going to satisfy me? Now get down there and suck me off" Before the words could register he had his hand on the back of her head and forced it down onto his crotch. Lucy knew what she had to do, and she wanted to do it, but there was certainly no choice. She pulled his jeans down and off, so that she could do the job justice, and she was determined to make up for her previous transgressions.. Pulling his thighs apart she lapped around the sides, and then the base, of his balls, gently pulling at the now rock hard cock as she did it, then she bent as far down as she could, lifted his balls and darted her tongue around his asshole. The results were electric. It was as though he convulsed, then grabbed her head with both hands and drove her mouth down onto his weeping cock. "God damn you're a dirty bitch aren't you, Lucy? Now make me come with your mouth" They were simple words, but they meant so much to her. Her man needed pleasing, he needed relief, and release,, and it was her task to deliver. The force of his hands had impaled his cock into the back of her throat, and her nose was sunk deep in the fleshy folds of his ball sacs. She came up for air then sank down again, slurping and sucking on his love meat. And that was her job. To bring tat lovely spunk up from those balls and spurting into her willing mouth, and she was going to do it. Careful not to catch him him with her teeth, she began to intensify her bobbing motion, swirling her tongue around the glans as she went. Then imperceptibly the motion changed, instead of her setting the pace, he did. His cock sliding in and out of her pink lipstick coated lips with increasing urgency. He was fucking her mouth now. Gently, she cupped his balls with her right hand. "Go on, bitch" he snarled. And with that he felt his right hand snake behind her and slip a finger up her asshole. Well that was seventh heaven moment as she slavered over his swelling cock for all she was worth. And so as to drive her home Phil then raised his hand and started to spank her ass again exactly in time with her cum inducing bobs. As her tender ass cheeks screamed at the treatment they were now re-experiencing, Phil's cock exploded into her mouth, fizzing warm spunk over her tongue, sliding down her throat, and starting to ooze out from her lips. it was as if a soda siphon had exploded. "Don't you lose a drop" he yelled at her. Obediently, Lucy swallowed the salty load, caught the errant drips with her fingers and then licked them back in. Eagerly she ran her tongue and lips around the now spent cock to ensure that she had indeed caught every drop of spunk, and that the shaft which had given her so much pleasure was now clean. Silently they both got themselves dressed and straight again. Lucy was in awe at what she had just done, of the psychological shift which had taken place. No longer was she simply seeing what sex with men was like. Now she was experiencing it as a woman. And she loved it. Dressing pretty, enticing and exciting her man, then submitting to his will, to his fingers, to his hands, to his cock. She wondered what was to happen next. "Right Lucy, drive, and follow my instructions. I'm not finished with you yet. We're going to go to a dogging site now, where I want to introduce you to a few of my friends..............................." To be continued....