Caution: This Drama Sex Story contains strong sexual content, including boy, Ma/mt, Consensual, Romantic, NonConsensual, Reluctant, Rape, TransGender, CrossDressing, Shemale, Fiction, Cheating, Incest, Uncle, Nephew, MaleDom, Rough, Oral Sex, Anal Sex, Masturbation, Exhibitionism, Voyeurism, Foot Fetish, Leg Fetish, Transformation,
Desc: Drama Sex Story: Chapter 1 - Mike Harris was seventeen years old when the worst blizzard ever to hit Chelmsford forest struck in December 1986. Mike was staying at The Cottage deep in the woods where he liked to dress as Michele Nylons, tranvestite vixen. Little did Michele know that she was going to get an unexpected visitor and that the visitor was staying for a while.
Mike Harris was seventeen years old when the worst blizzard ever to hit Chelmsford forest struck in December 1986. That is when this story really begins. But first we need to learn a little about Mike Harris before that fateful winter's day.
Mike's father had left the family home when he was still a baby. He lived at home with his mother Doris and his older sister Charlotte. He had been an 'accident' his mother said. He wasn't 'planned' and his mother made no secret of the fact that she thought his arrival had been the final straw that led to her husband leaving their already shaky marriage.
His mother worked as a secretary for a legal firm and what little spare time she had from work she spent socialising with the staff from the office. His sister pretty much ignored him as he was growing up, concentrating instead on her small circle of girlfriends and of course her many boyfriends who seemed to come and go with monotonous regularity. Sometime during his adolescence he came to realise that Charlotte had a reputation; and that she was what was unflatteringly referred to in those days as 'the town bike'.
Not that lack of family affection particularly bothered him; he preferred his own company. Nor was his upbringing totally loveless; his mom and his sister readily showered with him with affection on his birthday and at Christmas. They also took annual holidays together at the cottage that they shared with the rest of the Harris family. It wasn't that his mom and sister didn't love him; it's just that they didn't have much time for him.
Mike grew up a loner, he spent most of his spare time indoors reading and watching television. He liked descriptive novels where the hero rescued the heroine from the clutches of the villain. He liked movies and television shows of the same genre. It wasn't until puberty that he realised he was identifying more with the heroines in the stories rather than the heroes and he begun to wonder why.
It was during his adolescence, around the same time that he realised his sister was a slut, that he admitted to himself that he had a predilection for women's underwear. But we will come back to this later.
The Harris clan was scattered across the shire, they were mainly working class stock who only got together for special occasions. Family celebrations were very much restricted to births, deaths and marriages, they were the sort of family who seemed to be happy not living in each other's pockets. They had one asset that they all shared and treasured. A cottage deep in Chelmsford wood.
The small cottage was set on a modest plot of land next to a small lake. A single dirt road wound three miles through the woods to the cottage and the nearest neighbour was a good mile away. There was no electricity line and a hand pump provided water from the lake. One of the more affluent families had installed a small generator but most of the visitors to the cottage preferred to use the combustion stove, which also provided hot water, and the kerosene lamps were more than adequate to light up the small two bedroom, one bathroom cottage.
The cottage had been in the Harris family for so long that no one really knew when or how the family acquired it. The cottage was shared amongst the five Harris families and an annual schedule was drawn up at the beginning of each year ensuring that the most popular spring and summer months were allocated fairly.
Mike considered it good fortune that his mother hadn't remarried because then they would no longer be members of the Harris clan and would forfeit their rights to the cottage. That said, because Mike's father had left them so long ago, they were only begrudgingly given access to the cottage, and their allocated periods seemed to be disproportionably in the autumn and winter.
Mike loved spending time at the cottage. When he was younger he would go to the cottage with his mother and sister and swim in lake, fish, hike and ride his bike along the forest trails. It was the only place he took an interest in the outdoors. As his sister got older she lost interest in the cottage and Mike had to plead to get his mother to take him. By the time he was thirteen his mother and sister had lost all interest in the cottage but his mother allowed him to go there by himself now that he was a teenager. The truth was that even though she couldn't give a shit about the cottage she didn't want her side of the family to give up on something she thought they had right to.
And so we return to Mike's penchant for ladies underwear. Living with two women who ignored his presence to a great extent Mike grew up surrounded by female paraphernalia. His earliest memories are of using a bathroom where stockings, panties and slips were rinsed in the sink and hung up to dry. The stockings eventually gave way to pantyhose and cotton panties and slips became satin, rayon and nylon. They hung from the shower curtain and towel rails like mystical talismans. He knew they were taboo; girl's things that boys had no right to touch. Mike couldn't remember when he first lifted one of the fascinating items down from the shower curtain rail and bought the silky garment to his cheek, caressing his body with the sensuous nylon and satin.
The sensation of the sleek fabric on his skin was like nothing he had ever experienced in his short life. What probably also nourished his fetish was the way his mother and sister dressed and behaved around him. When he was twelve his sister was eighteen and she dressed in eighties kitsch. She wore a lot of lycra tights and bodysuits around the house and tight pencil skirts, satin blouses and tight-fitting jackets for work. These short skirts were accessorised with silky pantyhose, high-heels, high hair and heavy colourful eye makeup. His mother also wore tight-fitting business suits, satin blouses, high-heels and heavy makeup. Sometimes Mother and daughter even borrowed each other's clothes.
What made matters worse was that they had no compunction in getting around the house partially clothed in his presence. His mother regularly turned up for breakfast dressed only in slip, bra, panties and hose. Her makeup would already be applied and she would eat her cereal dressed only in her lingerie, putting on her heels at the table, stepping into her skirt and pulling on her blouse and jacket just before leaving for work. Sometimes she would even ask Mike to tuck the back of her blouse into her skirt and zip it up or to buckle up her shoes if she was wearing sling-backs.
Mike's fingers would inadvertently come into contact with her silky slips and blouses and her gossamer nylons while he did these tasks; and the garments felt far more luxurious when filled with a warm perfumed body.
His sister was not quiet the exhibitionist that his mother was but she also seemed to ignore his presence and often sat with her legs open or would lie on the couch with her skirt riding high on her thighs. Charlotte had left school at sixteen and had a job as a shop assistant in a ladies clothing store. She didn't earn much but she loved the job because she was required to dress nicely for work and she got good discounts on her clothes.
Mike figured it was no surprise that he was developing a fetish for lingerie and hosiery being surrounded by it almost constantly. He knew that boys should admire the women wearing these garments but he knew they should not actually be obsessed with the garments themselves.
He didn't have an incestuous bone in his body and he did not lust after his mother and sister but he lusted after the clothes they wore; the feel, the texture of their lingerie and the smell of their makeup, powder and perfume. In a subconscious way he was jealous. He wanted to wear the pantyhose, the panties and the slips that they wore. Why couldn't he? Why couldn't boys wear luxurious silky underwear instead of boring cotton briefs and singlets?
And so it started. One day while his mother and sister were at work Mike found himself in the bathroom staring at the array of panties and nylons left hung up to dry by his sister and mother. He gently fondled the silky soft objects that had become his obsession. Eventually his fascination for the slinky garments became sexual in nature. He began masturbating with them; rubbing them over his erect penis as he slowly bought himself to climax. He found it immensely pleasurable to slide the leg of a pair of pantyhose over his erection and then wrap a pair of satin panties around his turgid member and slowly stroke it until he spent his issue in the diaphanous tunnel.
Mike was terrified that his mother or sister would find out what he was doing. He would carefully wash the semen-soaked garments and hang them back up to dry where he had found them; praying his mother and sister wouldn't notice that their lingerie had been defiled.
Then one day it was different; he wanted to feel what it would be like to wear the objects of his desire; feel the luxurious garments against his skin. He sat on the toilet seat and slipped his toes into a pair of his sister's flesh-toned pantyhose and slowly rolled them up his calves; he stood up and smoothed the nylons up his thighs pulling the gusset tight around his buttocks and groin. He had seen his mother and sister don their hose so he knew how to do it properly. The feeling of the cool sheer nylon sliding up his legs and tightly but gently caressing his legs and his scrotum and penis was incredible. It was indescribably erotic and exotic. He was instantly hard.
He slid into a pair of full-cut rayon panties and smoothed them around his buttocks, pulling the waistband high on his slim hips. The panties hissed as they rasped over his pantyhose-clad legs; the rayon was soft and slippery, sliding easily over the nylon hose. He gasped with delight and pleasure. Oh how lucky it must be to be woman and be able to wear such sensuous undergarments every day! He flooded the front of the pantyhose and panties with scalding semen without even touching himself.
It wasn't long before Mike was wearing his sister's panties and pantyhose every chance he got. Later he tried on their bras, filling the cups with socks to make fake breasts; then he tried on a slip, first a half-slip, then he tried on a full-slip. It was exquisite! He would dress in pantyhose, panties, bra and slip and parade around the house while his sister and mother were out. He was terrified that they might come home unexpectedly and catch him; exposing him for the deviant he was. Somehow the fear of getting caught added to the immense pleasure he found being dressed that way.
He felt tremendous guilt and many a time he vowed that this would be the last time but eventually he would return to the bathroom or the laundry basket and help himself to the forbidden treasures. He knew he wasn't gay; he didn't think about men when he wore lingerie; he just revelled in the feel of the garments against his skin.
One day just before his sixteenth birthday he snuck into his mother's bedroom dressed in his sister's pantyhose, panties, bra and slip. He wanted to see what it felt like to wear high-heels with the lingerie. He had a collection of girly magazines; just soft porn really, and almost all of the women in the magazines wore high-heels with their lingerie.
He tried to get his feet into a pair of his mother's high-heeled pumps but they wouldn't quiet squeeze in. Then he found a pair of high-heeled sandals and although they were a tight fit he was able to adjust the straps so he could wear them. He got up from his mother's bed where he had sat down to try them on and unsteadily made his way over to the full-length mirror in the corner of the room. He was amazed at what he saw.
He stood so that his head was not visible in the reflection in the mirror. He could easily have been looking at the image of a slim young girl. His build was very slight but his legs were well defined. He turned around and was rewarded with the view of a magnificent, tight, well-formed arse. His senses of sight and touch were being stimulated; maybe one more thing? He tottered over to his mother's vanity and selected Poison, her favourite perfume and liberally sprayed himself. God he felt so sexy!
He walked back to the mirror. Mike regularly masturbated looking at pictures of models dressed in lingerie in his girly magazines and now he stared at his own reflection and furiously masturbated. He pulled his penis over the waistband of his pantyhose and panties and stroked himself until his issue spurted forth spraying everywhere. He was so engrossed in pleasuring himself that he didn't think of the consequences.
The slip, panties and hose were splattered with ropes of sticky semen. There were even gobbets of spunk on his mother's shoes and all over the floor of her bedroom.
Then he heard noises from downstairs.
"Mike? Mike? Are you home?" he heard his mother calling.
Mike panicked; he was going to be caught dressed in his sister's lingerie and his mother's shoes and to make matters worse he was soaked in semen!
"It's ok; he's not home," he head his mother say and then heard the ominous sound of high-heels clattering on the stairs.
Mike quickly pulled down his panties and kicked them off; he hurriedly wiped up as much of the semen as could off the floor. The floorboards were still a little damp but you would have to look carefully to see the stain. He walked as quickly and as quietly as could to his mother's walk-in wardrobe and pulled the door too just as she entered the bedroom. Mike looked through the slats of the shuttered door and found he had a decent view of the bedroom. His mother held the hand of a man Mike recognised as his uncle Steve and she pulled him through the door.
"We have to be quick; Mike's probably out on his bloody bike again but fuck knows when he'll come home," she pulled uncle Steve into the room and closed and locked the door.
"This is just so fucking naughty Doris; fucking my sister-in-law in her own bedroom!"
Mike knew his mother was no angel but fucking uncle Steve! Fucking her sister-in-law's husband! What on earth was she thinking? Mike knew that uncle Steve and aunty Joyce were the closest relatives they had, but he never dreamt that his mother and uncle were having an adulterous affair. He had to admit to himself that he found it quite exciting.
If he weren't hiding in the wardrobe dressed in his sister's underwear, scared shitless of being caught, he would probably be immensely turned on. His mother was wearing a snug black mini-dress, a pink satin blouse, black jacket, black open-toed heels, and what appeared to be a pair of ivory coloured pantyhose. It was a simple outfit that showed off her legs to good effect. She was also wearing her usual heavy makeup and lots of cheap jewellery.
She took off her jacket and threw it on the chair near the vanity. Mike breathed a sigh of relief that she hadn't taken the time to hang it in the wardrobe; the same wardrobe he was hiding inside dressed in pantyhose, bra, slip and high-heels, holding a pair of his sister's come-soaked panties.
"Come on Steve do me quickly!" his mother panted and held out her hand.
He fingers were bejewelled with rings, her fingernails painted a deep crimson; cheap gold bracelets jingled on her wrists. Steve heeded her beckoning and moved in even closer. His mother opened her legs wide apart and kissed him.
"Come on; I know what you like and you know what I like, now lets do it!" she panted.
Steve pushed up the hem of her short shirt, he exposed the entire front part of her waist right up to the waistband of her sheer white hose.
"No panties Doris? You naughty girl," he marvelled, his hand moved to her pubis.
"I hope you don't go out like this all the time?" he joked.
"Only when I'm meeting you," his mother smiled back.
Mike felt an erection begin to grow. He couldn't believe his mother spoke and behaved this way! It was shocking but it was also very exciting. He noticed he was gripping the come-soaked panties very tightly and he unclenched his fist and opened up the panties so he could press the damp satin against his hose-sheathed penis.
His mother fell back on the bed, pulling uncle Steve down on top of her. Mike had a perfect view through the small aperture. His mother lay on her back; her skirt hiked up and her legs wide apart.
"Come on; do me Steve, we don't have all day!" she demanded.
Steve stroked and rubbed Mike's mother through the translucent fabric covering her privates; he must have been hitting all the right places creating the most wonderful friction Mike thought as he rubbed his sister's panties on his cock. Then Steve lowered his head and began to lick his mother, it must have felt exquisite against her clit because the wet spot on the gusset of her pantyhose began to spread.
Doris lay back and closed her eyes, arms thrown up over her head as she let her brother-in-law have his way with her. His hands continued to stroke her thighs and buttocks, he kissed and licked all along the length of her cunt, drinking in the scent of her arousal. Biting with his teeth, he made a small hole in the crotch of her hose and proceeded to make an opening just large enough so he could access her naked clitoris peeking forth from its hood.
Her feet rose up and she clamped her thighs around Steve's face.
"Please don't stop," she softly begged, glancing down to the top of his head.
"I'm so close, please..."
She didn't have to worry. Steve was like a man possessed, intent on nothing more than the feeling of her hosiery beneath his fingers and the nubbin of her clitoris beneath his tongue. There was no mistaking her body language, or the way her increasingly desperate gasps suddenly gave way to open grunts, announcing her climax. Mike was amazed that it was not only he that had a fetish for nylons but his uncle Steve definitely did too.
Now that his mother had come it was obvious that Steve wanted some action. Mike rubbed his sister's panties harder against his cock as he watched Steve rise up from his mother's sopping cunt, he quickly stood up, kicked off his shoes and shucked out of his shirt and pulled down his trousers and underpants. His uncle's penis was fully erect, the glans was purple and it looked like it was throbbing; almost angry. Mike couldn't help but stare at that impressive erection, his own penis was throbbing and leaking pre-seminal fluid into the tight gossamer hose.
Mike watched his uncle take each of his mother's legs in his hands, he removed her heels and placed her nylon-clad feet against his broad chest. Closing his eyes, he moved her soles back and forth, revelling in the sensations. He took each foot in turn and kissed and sucked on her toes through the nylon, which his mother obviously found extremely arousing judging by her whimpers and moans. His hands glided along the undersides of her calves and thighs, elevating her legs so that they rested completely against this body.
He hugged her hose-clad limbs close to his chest and Mike watched with fascination as he proceeded to thrust his cock in the space between her thighs. Steve's face was one of unadulterated rapture as he fucked Mike's mother's thighs, and Mike stared fascinated at the obscene sight of his uncle's engorged glans appearing and disappearing from between his mother's legs.
"Does that really feel good Steve?" she asked.
"You have no idea," he rasped; sweat breaking out on his skin as he moved his hips ever faster, creating the most intense friction on his cock between the pale white nylons.
Uncle Steve nuzzled and kissed her feet, then held her legs firm once more as he redoubled his efforts, the smears of pre-seminal fluid wetting her pantyhose an unmistakable testament to the level of his arousal.
"Are you going to come like that," his mother asked with a quivering tone.
"God, yes," he replied, thrusting his hips hard into her thighs.
Mike was now furiously rubbing the sodden panties against his highly sensitive penis; the friction of the satin panties against the nylon hose was exquisite and he was close to his own orgasm.
Steve suddenly shuddered and Mike witnessed his uncle ejaculate. He was literally standing on his toes, riding each wave of his orgasm clasping his mother's legs to his chest, shooting long streams of warm semen onto her skirt and blouse; the final spurts dribbling down the insides of her pantyhose-clad legs. His uncle fell on top his mother and kissed her passionately and she rubbed her sodden hosiery on his body as they kissed and cuddled for a minute or two.
Mike had his second intense orgasm of the day watching his uncle spray his seed over his fully clothed mother; his semen flooded the gusset of his pantyhose, soaking into the slippery satin panties he was frenziedly rubbing on his cock. The smell of his mother's Poison still lingered on his body and as his orgasm wracked him he found the sensation of hose, bra and slip against his sensitive skin heightened the experience tenfold.
What he realised as his orgasm began to subside was that during the throes of his climax he had not identified with his uncle; he had imagined that it was he lying on the bed, taking his mother's place. That he was the one dressed in black miniskirt, blouse, heels and makeup being splattered by scalding semen. He shook his head to clear the image from his subconscious. What a silly idea! It was just the sensation of wearing his sister's lingerie that had bought on that notion surely!
"Ok lover let's get into the bathroom and clean up this mess, then I need to get changed and get back to work," his mother giggled and pushed uncle Steve off her.
Mike watched as his uncle, naked except for his socks, chase his fully clothed and semen spattered mother into the ensuite bathroom.
Mike quickly cleaned the closet floor and took off his mother's high-heels and wiped them clean of his semen. He couldn't remember exactly how the shoes had been arranged in the jumbled mess on the floor the closet. Was there a method to her madness or were her shoes just thrown on the floor in a heap? He didn't have time to worry; he dropped them on the floor and quickly padded away down the hall to his own bedroom.
As quietly as he could he stripped himself out of the semen-stained lingerie. He waited for his mother and uncle to dress and leave the house. He looked out the window and saw them drive away in Steve's little car. He buried the stained underwear at the bottom of the laundry basket and changed into his own clothes. He went back to his mother's bedroom and noticed that his mother had changed her bed linen. He also noticed a streaky wet stain where he had cleaned up his own semen off the polished wooden floor.
He almost fainted. His mother had obviously noticed the stain and mopped it or wiped it with a damp cloth. He bolted for the built-in closet and flung open the louvred doors. Sure enough, another damp patch belied where his mother had cleaned away the semen stains he had left behind.
"Fuck!" he sighed.
The next few hours were the most terrifying of his life. He was dreading confronting his mother when she came home from work and even considered running away from home.
"Have you been mooching in my bedroom Mike?" his mother asked him later that night.
He fervently denied it of course; but guilt was written all over his face. His mother surprised him by giving him a wry smile.
"Well I better not find out that you've been up to shenanigans in my bedroom Michael Harris," she said sternly, but her face held an amused expression.
Mike blanched and shook his head.
"Never mom; I promise," he whimpered.
"I think the little perv plays with our knickers while we're out!" Charlotte chuckled and punched him playfully in the shoulder.
His sister was joking, but she was awfully close to the truth and Mike vowed never to touch their lingerie again. It was bad enough that his mother rightfully suspected he had spied on her and uncle Steve having sex in her bedroom; but if she or his sister found out that he had been dressing in their lingerie he would die!
"Ok Charlotte; I think Mike knows now that he better not ever go into our bedrooms without our permission," Doris said sternly; her face now very serious.
"He might see things there that he was never meant to," she finished, eyeing him sternly.
It was the closest he ever came to being caught; and he repeated his vow never to touch his mother's or his sister's lingerie again. He did not however vow to never wear lingerie again, just not his sister's or his mother's.
Mike waited a few weeks to see if his mother was going to bring up his indiscretion again but she never did. The compulsion to dress in women's underwear built up until it became undeniable. Mike was far too scared to ever dress up at home again; he was terrified of being caught, but he had to dress up somewhere. Then an idea came to him! But first he would need to buy his own lingerie.
Mike was very frugal, he saved his pocket money and the few bob he made from a paper route. He had a saved a reasonable sum of money and now he decided to put it good use. Mike's only form of transport was a twelve-speed bike he had been given for his fourteenth birthday. He rode it everywhere, including on his paper route; that was one of the reasons why his legs were so well defined and his body so slim.
He started taking regular bike rides to Luxton, the closest big town to Chelmsford. It was far enough away that he would be unlikely to run into anyone from his school or any other family members. It was fifteen miles from Chelmsford but Mike made the round trip on his bike with his large rucksack on his back without too much exertion. He found a big department store where he thought he could buy lingerie without being too conspicuous. He blushed with embarrassment when he was approached by the matronly shop assistant in the lingerie section. He used the excuse that he was buying something nice for his girlfriend for her birthday and she took pity on him and helped him pick out a nice panty and bra set with a matching slip.
Then he went to a few different stores ready to use the same excuse if needed but in most cases the lingerie section was unattended and he just helped himself to what he wanted and steeled himself for any inquisitive glances he might receive from the checkout staff. Most of the counter staff were bored with their job and took no interest in him or his purchases and just rang up his purchases and gave him his change.
Pantyhose were easy to buy at the supermarket; he just made his selection and put them in with some innocuous items in a shopping basket and no one asked him any questions. He had decided to make a special purchase and he went to a specialist lingerie store and bought an expensive satin and lace garter belt and a selection of fifteen-denier fully-fashioned stockings. He couldn't wait to try them on and he nearly fell off his bike riding home.
He stashed his lingerie away in a secret compartment he had built in the back of his wardrobe. Then he executed the second and most important part of his plan.
"It's our weekend at the cottage isn't it mom?" Mike asked innocently enough.
"Yes Mike but it's bloody freezing out and me and your sister have a lot on this weekend," his mother replied, not even looking up from the book she was reading.
She was sitting in her big overstuffed chair with her legs curled under her and Mike couldn't help staring at the dark reinforced toes of her stockings and then tracing her shapely nylon-clad calves with his eyes until they disappeared under her skirt.
"I'm not going to the shitty cottage," Charlotte whined.
She was lying on her back on the lounge staring at some inane soap opera on the television. She was wearing a little A-line skirt and her long legs were bent at the knees with her platform shoes flat on the cushions; her skirt had rode up almost to her waist and Mike could just see her red satin panties under the gusset of her flesh-toned pantyhose. God these women made him horny! He wanted to dress just like they did!
"Can I go up on my own then mom? I'll ride my bike up and back and it'll get me out of the house for the weekend," he asked.
"Sure you can son," Doris replied turning a page and reaching for her obligatory glass of wine.
A quick recollection flew into his head depicting his mother lying on her back fully clothed while uncle Steve fucked her white-stockinged legs and he shook his head to remove it.
"Thanks mom," he beamed and bounced up the stairs to his room to pack his treasures for the weekend.
And so Mike's regular excursions to the cottage by himself began. And of course while he was there alone he could do whatever he wanted.
He enjoyed parading around the cottage dressed in lingerie and did it whenever he could. The solitude and privacy of the cottage set deep in the woods meant he could dress in lingerie all day and all night if he wanted too. He found a hiding place in the cottage where he could hide his girly requisites and added to them and replaced items as they became worn out. He also added to his magazine collection and stared endlessly at the seductively clothed models contained in their pages. His compulsion to dress like a woman kept developing until eventually it was not just lingerie that fascinated him. He wanted to wear high-heels and maybe try on a nice mini-skirt and sexy blouse. He loved skirts. He even loved the word 'skirt'! It evoked images of his mother and sister's tight little skirts, hems wore high on the thigh, rustling against their nylon-clad legs when they strode around the house on their high-heels.
Mike thought about it for a while; he knew his lingerie sizes from trial and error when trying on his mother and sister's panties, bras and slips. But what dress size was he? What blouse size? What woman's shoe size? This was before the days of the Internet and books that converted ladies sizes to men's sizes were just not available; where would one get such a book anyway?
Besides; he couldn't walk into a department store and just ask to try on a few skirts and blouses and he certainly couldn't just take a few items off the racks and take them to a checkout. That would raise a few eyebrows!
Then one day he was riding around Luxton when he rode past a big Oxfam depot and when hit him! Problem solved! He could buy second hand ladies clothing from Oxfam or other charity shops and if it didn't fit he could simply throw it away; it wouldn't cost him much and the staff there were less likely to care what he bought; they just wanted his donations.
So Mike summoned up the courage to enter the Oxfam shop and after thirty gruelling heart-stopping minutes he had a nice collection of skirts and blouses. He even found a nice business suit skirt-jacket combination that he thought would fit him. It was almost exactly like the suits his mother wore to work. Sure enough the little old lady at the counter couldn't give a toss about his purchases, she just added up the total and took his cash.
A few days later he returned, early in the afternoon when the store was quiet, and quickly kicked off his shoes and tried on four pairs of high-heels. Three of the four pairs fitted him and he took them to the counter. This time the little old lady did give him an inquisitive look but she didn't say anything, she just gave him a knowing smile and handed him his change. Mike blushed, his face turned a deep crimson and he bolted from the store with his purchases.
And so Mike continued to go to the cottage and dress up in lingerie, skirts, blouses, hose and heels but he still looked like a boy in girl's clothes.
He looked good dressed as girl; that is he had a good body and great legs but it was still the face of teenage boy that was reflected in the mirror. It was time to take the next step!
He rode into Luxton and he bought a makeup case, explaining to the shop assistant that it was a birthday present for his cousin who was only just beginning allowed to wear makeup. The shop assistant was very helpful and helped Mike select some nice shades of lipstick that his 'cousin' might like. She also advised him that girls love perfume and Mike purchased a bottle of his beloved Poison perfume 'because he liked his cousin so much'. The shop assistant was happy because she though she had fleeced the young naïve teenager of his cash and Mike was happy because he had acquired all of his makeup and perfume requisites at one shop with no fuss or embarrassment at all.
He bought some cheap jewellery and clip-on earrings at a department store and then returned to the Oxfam shop where he found two good quality wigs. One was a shoulder-length dark brunette bob and the other a honey-blond, which came just below his shoulders.
He took these purchases home and couldn't wait to get them to the cottage so he could undergo his first transformation from Mike Harris to Michele Nylons; the enfemme name he decided to call himself. A few months after his seventeenth birthday and one week before Christmas his mother dropped the bombshell that she was going to Majorca for the Christmas holidays with a friend from work.
"You two are old enough to look after yourselves now," she said dismissively when she gave her son and daughter the news.
Charlotte was the first to chime in.
"Can I have Ben over for Christmas then?" Ben being her latest beau.
"You mean can you bend over for Ben at Christmas!" Mike sniggered and both of the women gave him a steely look.
"It's ok mom and Sis; I'll go to the cottage," he added quickly.
"Don't know what you want to go to cottage for in the middle of winter for, but sure ok," his mother answered.
"So he can stroke his little peeny-weeny all day long," Charlotte teased.
"Jesus! I'll be glad when I'm on that plane," his mother sighed.
And that is how Mike happened to be in the cottage when the worst blizzard ever to hit Chelmsford struck in December 1986.
Mike arrived at the cottage just before it started to snow and he was so excited that he didn't even notice when it began. He opened his rucksack and laid out his recent purchases and started preparing himself to learn how to become a transvestite. He knew what a transvestite was; a man who dressed in women's clothes and looked very much like a woman when transformed. He was going to become Michele Nylons for the first time and he was very excited about it.
He got the generator going and lit a blazing fire in the open fireplace; it warmed the cottage and soon the hot water system was piping hot. He had very little body hair but he painstakingly shaved his chest, stomach and legs and then the fine hairs on his hands and arms. He shaved his face and felt his skin; it was smooth and supple.
Then he opened a pot of hair removal cream and after reading the instructions he applied a thick coat of the smelly cream over the hairs in his crotch and buttocks making sure that he got into all of the crevasses. He watched with amusement as small clumps of his body hair disappeared down the drain when his rinsed it off in the shower. He was amazed at how smooth and sensual his shaved body felt and he decided to keep his body permanently hairless from now on. Its not like anyone would notice.
Now came the difficult part; learning how to apply makeup. Mike sat down at the dresser in the small bedroom and arranged the contents of the cosmetics case in front of him. He was fascinated with the cosmetics. Long tubes of mascara, eyeliner and lipstick, bottles and pots of foundation and nailpolish, palettes of bright coloured eyeshadow, blush, rouge and finishing powder.
He opened up a magazine featuring pictures of overly-madeup models and selected one of favourites and decided to try and duplicate her makeup; his first ever attempt at applying cosmetics. The foundation, finishing powder, blush and lipstick were not too hard to get right with a little practice but it took several attempts to get the eye makeup anywhere near as good as the girl in the picture. After two frustrating hours was reasonably astute at getting his eyeliner and eyeshadow right. Applying the mascara was not quite so difficult, but the first few times he slipped and smeared some on his eyelids. Also it tended to clot on his eyelashes; but he eventually got the hang of applying a nice thick even coat to his upper and lower eyelashes.
When he had the hang of putting on the makeup he washed his face completely clean with warm soapy water and applied some moisturiser so he had a clean palette for his very first full transformation from Mike to Michele.
What Mike didn't know was why his mother was going to Majorca. It was because of a developing family scandal. Aunty Joyce had found out about his mother's illicit affair with uncle Steve. Doris was running off to Majorca to avoid the disgrace and uncle Steve had packed a bag and moved out of his home at the insistence of his wife. He had nowhere to go so he decided to spend a few nights at the Harris cottage until Joyce either got over her anger and took him back or he found somewhere permanent to live. He was driving down the highway towards Chelmsford forest when it started to snow heavily.
"Hope I get to the cottage before this fucking snow cuts off the access road," he said to himself.
Mike had been experimenting with how to make more realistic breastforms rather than just stuffing socks into his bra cups. He now had a tried and true method that did the job. He opened a packet of pantyhose and cut the legs from the gusset. He filled the feet of the pantyhose legs with rice until he had the desired size and then doubled the legs over and tied them off with a couple of overhand knots. The knots made nice imitation nipples when the breastforms were placed inside his bra cups.
Mike sat down at the dresser and applied foundation and finishing powder. He worked on his eyeliner next, concentrating on getting it just right from the inner corner to the outer corners of both top and bottom eyelids, gradually thickening the line. Next he went to work on the eyeshadow using a combination of light blue, purple and pink; blending it as close as possible to resemble the eyes of the model in his fashion magazine. He rouged his cheeks with blusher and applied another coat of finishing powder. He painstakingly mascaraed his eyelashes and reached for the plum red lipstick and carefully applied three coats, biting down on a tissue to set the lipstick just like he had seen his mother and sister do.
He painted his toenails and fingernails with matching plum red nailpolish. Coating the fingernails of his left hand was relatively easy, but Mike found it awkward using his left hand to paint the nails on the fingers of right hand. When he was happy with his makeup he reached for a wig. The shoulder-length brunette bob sat perfectly on his head, the fringe level with his eyebrows. He brushed it out until it was sleek and glossy.
He was amazed at the transformation; he looked very attractive. He looked as good as some of the models in his magazines. Mike took his homemade breastforms and fitted them inside the cups of a red satin and lace brassiere then he opened a packet of flesh-toned Pretty Polly sheer to the waist pantyhose. He carefully fitted the toes of the pantyhose around his feet and admired the lustre of his nailpolished toenails through the reinforced pantyhose toes.
The next task was a little uncomfortable but essential if he wanted a woman's silhouette. He tucked his penis and scrotum under his crotch and taped them in place. He had found the tape in a shop that specialised in actor's accoutrements and stage makeup. The stage makeup was not suitable for his purposes but when he saw the gaff tape, which actors used to affix prosthetics, he had an idea how he could use it and bought a couple of rolls.
He smoothed the small wrinkles out of the pantyhose as he drew them up his legs. The luxurious feel of the silken hosiery on his shaved legs was very sensuous. He stepped into a pair of red bikini-cut satin panties. The panties hissed as they slid up his nylon-sheathed thighs and as he adjusted them to fit snugly around his buttocks, he once again marvelled at the opulent feel of the satin and nylon against his body. He selected a white rayon half-slip, the cool sleek material fluttered like the wings of a butterfly against his legs when he stepped into and eased the garment up his legs and adjusted it so the hem sat high on his thighs.
It was about this time that Mike began to think of himself as Michele. He was no longer Mike, the skinny teenage boy with a feminine figure; she was Michele Nylons, transvestite vixen!
Michele stepped into a navy blue A-line skirt and then buttoned herself into a mauve satin blouse. She tucked the blouse into the waistband of her skirt and closed the zipper. She adjusted the waistband of her skirt around her midriff, and smoothed the skirt down her legs so the hem just covered the lace edging on her slip. The skirt was tight around her buttocks and thighs and the hem sat high up her long legs. Perfect!
Someone had bought an old full-length dressing mirror to the cottage and it had stood in the corner of the bedroom, disused and fly specked. Mike had cleaned it up during his many visits and regularly made use of it; putting it back in the corner and covering it with an old sheet before he left. He pulled the mirror into the centre of the room where the light was best.
Michele looked at herself in the mirror and saw exactly what he was hoping to see: a young, attractive, slightly slutty-looking, young woman. She stepped into a pair of black high-heeled sandals then sat back down at the dresser and accessorised herself with the jewellery. She sprayed herself liberally with Poison, her favourite perfume, and then stood in front of the mirror once again.
She pirouetted, curtsied, lifted her skirt, lowered her skirt, blew kisses and posed seductively and then lewdly in front of the mirror for the good part of an hour as the snow continued to fall heavily outside. She was amazed at how seductive and sexy she looked. She never heard the car pull up outside of the cottage.
When Steve drove up to the cottage he was quite surprised to find smoke coming from the chimney and hear the hum of the generator. The lights were on and there were obvious signs of occupation.
He looked through the various windows of the single story structure trying to see who was staying at the cottage. He eventually he saw movement in one of bedroom windows. Steve couldn't believe his eyes. A young coquette was posing in front of a full-length vanity mirror; vamping it up and putting on a show. She was dressed in skirt, blouse, hose and heels and wearing heavy makeup. She wore her hair in a brunette bob and was very attractive. She was sexy as hell and he stroked his hard cock through his jeans as he watched her prance and pose in front of the mirror. He particularly liked her long, well-toned, nylon-clad legs.
Steve had been looking at the girl though the window for about thirty minutes mesmerised by her performance when he realised that if he stayed outside much longer he would probably get frostbite. He went back to his car and rummaged around in his duffle bag until he found his Polaroid camera. He made his way back to the window where the snow was now beginning to drift quite significantly and took several pictures of the young woman as she posed in front of the mirror.
Maybe his excommunication from the family home might not be such a bad thing? He was alone in the woods with a sexy teenage girl who had legs that went on forever. He looked at the Polaroids he had taken, they were pretty good; he had a couple of the woman front-on reflected in the mirror and a few of her brazenly lifting her skirt. He didn't recognise her; but there was something familiar about her that he couldn't quite fathom. He stuffed the pictures in his pocket. It was time he went inside and introduced himself.
The snow began to fall harder; the snowstorm was developing into a blizzard.
boy / Ma/mt / Consensual / Romantic / NonConsensual / Reluctant / Rape / TransGender / CrossDressing / Shemale / Fiction / Cheating / Incest / Uncle / Nephew / MaleDom / Rough / Oral Sex / Anal Sex / Masturbation / Exhibitionism / Voyeurism / Foot Fetish / Leg Fetish / Transformation /