The Devil You Know
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Ma/Ma, NonConsensual, Reluctant, Coercion, Blackmail, TransGender, CrossDressing, Incest, Mother, Son, Spanking, Rough, Humiliation, Group Sex, Oral Sex, Anal Sex, Masturbation, Petting, Sex Toys, Cream Pie, BBW, Foot Fetish, Leg Fetish, Transformation,
Desc: Erotica Sex Story: Chapter 1 - Secret transvestite Michele is found out by her boss who blackmails her forces her to comply with his demands.
Brian Davies sat on the hard toilet seat in a cubicle of the men's room on the twelfth floor of the building housing the large publishing company he worked for; he was reading the Daily Mail and trying to kill the last half hour before quitting time. As a middle-management employee he didn't really work mandated hours; he was expected to work whatever hours were necessary to ensure his small team met or exceeded their productivity quotas. Brian thought that productivity quotas were a crock of shit; what the bosses really wanted was income in the form of hard currency. He also thought that in the current economic climate he and his small team might not be around much longer,
"Fuck it!" he whispered to himself.
"Five fucking years of late nights, constant travel, and hard work and all I've got to show for it is a mortgage I can only just pay, and a fucking second-hand Beamer!" he whined quietly and flicked the page over to look at the 'Employment Opportunities' section.
Brian was sitting sideways on the toilet hoping that his feet wouldn't show under the door of the cramped cubicle. At five o'clock he intended to shut down his workstation and get the fuck out of the office and he didn't want any of his staff chasing him down with the mundane crap they called work.
He was vaguely aware when the door to the rest room opened and closed and then he started as the door to the toilet cubicle next to his opened and closed.
'Fuck!' he thought to himself.
Mike Harris was one of five employees of the publishing company who worked on the team headed up by Brian Davis. Mike didn't like Brian much and was damn sure that Brian didn't think much of him. They seldom socialised, but when the team got together for 'team building activities' (read amateur team sports followed by heavy drinking), it seemed to Mike that Brian picked him out especially for belittlement and derision. There was nothing that Mike could actually formally complain about; but Mike seemed to treat him with an undercurrent of disdain that Brian didn't use with the other team members.
'Fuck him!' Mike thought to himself as he entered the men's room on the twelfth floor.
Mike quickly looked around the men's room and checked to ensure that the adjoining cubicle was empty. The door to the cubicle was closed but he couldn't see any feet under the door so he assumed it was vacant.
'We're all getting the arse soon anyway; so fuck him and the rest of the team!' he thought as he closed and locked the toilet door.
Mike hung his coat on the hook on the back of the door and unbuckled his belt and unzipped the fly of his suit pants. He slid his trousers down; the fabric hissed quietly as his trousers slid down his legs. Mike shuddered at the sensation as the micro-fibre trouser material rubbed against the sleek lycra of the sheer-to-the-waist pantyhose he was wearing under his suit. His underpants consisted of a pair of full-cut satin panties and his cock was tenting the front panel. A small wet patch of pre-seminal fluid had soaked through the gusset of the pantyhose and was spreading across the front of his panties.
Mike Harris was a closet crossdresser and sometimes he just couldn't resist the urge to wear women's underwear to work under his suit. He knew it was dangerous and the consequences of being caught were horrific but he couldn't help himself.
Mike reached into the inside pocket of his jacket where it hung on the door and pulled out a folded piece of paper. He opened it with trembling fingers and looked at the image printed on the paper. It was a beautiful transvestite; heavily made-up and wearing sexy lingerie, fully-fashioned stockings and high-heels. She was on her knees fellating a similarly dressed transvestite who was sporting an enormous erection which was sticking out of the front of her open-crotch panties.
Mike had downloaded the image on his workstation only thirty minutes ago and stored it in a hidden folder on his desktop. His workstation was set in a corner of the office where the screen could not be viewed by his co-workers and he had kept opening the file and looking at it even though he knew it was dangerous; if someone came over to chat they might see his screen before he could close the file.
He couldn't help himself and as his erection grew inside his trousers, encased and caressed by the panties and hose, he knew he would have to take care of his erection or go home with an obvious bulge in the front of his pants. He'd scanned the office carefully to make sure the coast was clear and then dumped the image onto the high-speed colour printer on his desk, stuffed it in his jacket and quickly headed for the men's room.
That picture and the resultant hard-on were to seal Mike Harris's fate and determine his future for some time to come. Mike would normally never use the rest room at work if he was wearing lingerie under his suit. He'd hold it in, or if he had to go, he'd leave the building and use the rest rooms in the shopping centre across the street; they had floor to ceiling doors on the cubicles. Then he'd puff a quick smoke on the sidewalk and then return to the twelfth floor with everyone thinking he had just ducked out for a smoke.
Today Mike was so sexually aroused that he risked using the toilet at work so that he could quickly relieve himself. He figured it was that close to quitting time that everyone would be too busy packing up for the day to bother using the bathroom before they headed home for the weekend.
Mike sat on the cold toilet seat; his trousers bunched around his ankles, and looked at the picture of the two transvestites. He stroked his cock through the diaphanous material of his pantyhose and panties. He needed release quickly so he stood up and without thinking he pushed his pantyhose and panties down his legs until they bunched together in a silky gathering around his shins.
In the silence of men's room Brian Davies heard the occupant of the adjacent cubicle unzip and drop his pants. He heard the crackle of paper being unfolded and assumed that the guy was putting one of the disposable paper toilet seat covers on the seat. He hoped the guy would hurry and do his business so and then fuck off and leave him in peace to finish his newspaper.
Brian heard the man stand up again.
'Fuck! What's with this guy?' he thought to himself.
He glanced at the partition separating the cubicles and looked down. Brian nearly choked at what he saw. The faggot in the cubicle next door pulled a pair of flesh-toned pantyhose and white satin panties down his legs and sat back down! Brian was dumbfounded; and then even more so when he heard the unmistakeable sounds of a man masturbating.
Mike was acutely aware of the slapping sounds he was making in the silence of the men's room as his hand feverishly wanked away at his cock. He didn't care because he knew he wouldn't take long. Mike only just had time to drop the picture and grab a handful of toilet tissue and shove it into his crotch before his throbbing penis expelled copious ropes of hot semen.
Mike gasped and sucked in and out huge lungfuls of air as his orgasm washed over him. He caught all of his emission in the wad of toilet paper; and the cleaned up his slowly deflating penis and then stood up and carefully pulled up his pantyhose, smoothing the wrinkles out of them as he slid them up his legs. He pulled up his panties and adjusted his cock inside the layers of nylon and satin so that his slowly shrinking erection was not too obvious, and then pulled up his pants. He flushed; and then left the men's room after washing his hands.
If Mike had not been breathing so heavily when he was masturbating or in such a hurry to leave after he had finished masturbating he might not have been found out. As it was, Brian Davies was able to get a good look at his shoes under the cubicle partition and when the phantom masturbator left the men's room Brian checked out the cubicle and found the picture of the two transvestites on the floor where Mike had dropped it. He put the picture in his coat pocket.
Brian Davies would recognise those ugly brown Oxfords anywhere! They belonged to Mike Harris. Now what was he going to do with this delicious titbit of information? Mike Harris wore women's clothing under his work clothes and liked to masturbate to pictures of transvestites!
"Hmmm; there are some possibilities here," he said to himself as he made his way back to his office.
As team leader, Brian Davies had his own office. He looked out the glass walls into the large open-plan office where his team worked and watched that skinny runt Mike Harris pack his pathetic belongings into his briefcase and then turn off his workstation and leave the office. Brian opened the bottom drawer of his desk and took out a bottle of single malt scotch whiskey and poured himself a large drink.
He sipped his drink and watched the office quickly empty as his team left in dribs and drabs in a hurry to get home for the weekend. Some of them called by to say goodbye and he tipped his glass to them, barely acknowledging their presence. He was thinking and plotting.
He had planned to leave early himself but was now determined to stay at work until everyone had left for the day. Once they had, he punched up a spreadsheet on his computer screen which listed all of his staff's logins and passwords. He made his way over to Mike Harris's workstation and fired up his computer and logged in.
Mike Harris was a fucking idiot! He worked for a publishing company, sitting at a computer all day but wasn't smart enough to cover his tracks on his computer!
Brian perused Mike Harris's internet browsing history and then pulled up his temporary internet files. Mike Harris had accessed dozens of transvestite sites on his work computer. Using the Tools menu Brian clicked Folder Options and displayed the hidden files on Mike's computer. Two hours later he had looked at over a hundred pornographic pictures of transvestites having sex with each other. What surprised him was that he sporting a throbbing erection!
Brian did not in anyway consider himself a fag.
"Goddamn; some of those trannies look sexy as hell," he said to himself as he adjusted his erection in his pants to make himself more comfortable.
He absentmindedly rubbed his cock through his trousers and continued to browse the images until he came to the end of the files in the folder. Then he found a sub-folder called 'video'. He opened the folder and double-clicked the first file. A heavily-built transvestite in full makeup, blonde wig, red bustiere, black stockings and high-heels was between the legs of a slender transvestite dressed in white satin and lace. The larger transvestite held the legs of the other transvestite far apart whilst she thrust her long thick cock in and out of her anus.
He was thinking of these transvestites as 'her'. They dressed in sexy clothes and wore lots of makeup and sexy lingerie, stockings and high-heels. They were sexier in some ways than most of the women he knew. His cock was throbbing as he watched the video repeat itself in an endless loop.
Brian rummaged through Mike Harris's desk drawers looking for some tissues when he saw something a lot more interesting. A skerrick of coffee-coloured nylon poked out from under a file cover. He gently tugged at it and single nylon stocking unsheathed itself from its hiding place in the bottom of the drawer.
Brian looked around; the office was dark except for the glow of the computer screen in front of him; the overhead lights worked on a timer and it had clicked over and turned the lights off promptly at 7:00pm. He checked again to see that no one was around; the cleaners wouldn't be in until 9:00pm.
Sweating a little in anticipation, Brian Davies opened his flies and freed his throbbing cock. He slid the nylon stocking over his member and stroked it with long slow strokes whilst his eyes remained glued to the screen.
He managed to stroke his cock six times before the material of the stocking darkened and then a gobbet of white cream formed on the outside of the stocking where his penis pushed against the fabric. The gobbet continued to grow forming a large globule of warm semen, the globule swelled as his cock throbbed and his scrotum contracted, emptying the contents of his sac.
Brian shuddered and gasped until he was spent. He wiped his shaft with the sticky stocking and then wrapped it in his handkerchief and put it his pocket. He zipped himself up and then went his office and came back with a flash drive. It took a few minutes to copy the contents of Mike's hidden files onto the flash drive. He then opened Mike's Outlook folder and downloaded all of his email contacts. He removed the flash drive and smiled evilly to himself.
He shut down the programs he was running and returned Mike Harris's computer to the same state that he had found it in and then logged off.
Brian would be having words with Mike Harris; but he hadn't quite decided what he was going to with him yet.
That evening and all of the next day Brian sat in front of his home computer looking though the files he had downloaded from Mike Harris's workstation. He became fascinated and entranced by the images of the transvestites. They wore sexy skirts and blouses made from silk, taffeta, lace, nylon, lycra and satin. They wore sexy lingerie: bustieres, garter-belts, suspenders and diaphanously sheer nylon stockings or pantyhose and silky panties. Their makeup was heavy and feminised their male features such that most of them could pass as real women unless you looked very close. They wore high-heels: pumps, sandals, court-shoes and boots.
"They dressed how women should dress!" Brian said to himself.
As part of the company management he sat on the 'office administration board' and had been at the meeting last year when the company had reviewed its dress code. Some of the women employees had complained it was too strict and not up with times.
The result had been that the bare-legged, pantsuit-wearing, minimal-makeup, flat-heeled, comfortable-shoe, brigade had won out and most of the female staff now wore 'comfortable but appropriate office attire' to work. Appropriate!!! One of the secretaries even had the cheek to wear khaki walk shorts to work last summer; and the bitch hadn't even shaved her legs!
Few of the women in the office now wore skirts, hosiery, or high-heels to work. There was one exception however.
Carolyn Jones was the office manager. She was fifty-ish; and sexy in a matronly sort of way. She always wore nice business suits with skirts to that came to just above her shapely knees or skirt and blouse combinations that showed a bit of cleavage. She always wore hosiery and heels; and her makeup was perfect, her raven hair was carefully coiffured, and she smelt wonderful.
Last year she had turned up at the office fancy-dress Christmas party wearing a bright red satin 'Santa's helper' outfit which consisted of a tight dress with a hem that stopped at mid-thigh, a matching Santa hat, bright red high-heeled sandals and shiny taupe pantyhose. Brian had spent most of the day hiding a boner under his desk with his eyes glued to her tight ass and long legs. Carolyn Jones might have been old enough to be his mother but she was sexy as hell!
Later, as the party was nearing its boozy completion, she had cornered him under the mistletoe and drunkenly demanded a kiss. Her bright-red lipstick tasted lovely and she had surreptitiously slipped her tongue into his mouth a little, pressing her body against his as they kissed. Brian squeezed her ass and she had reached between their bodies and slowly squeezed his hard cock just once.
"You wish!" she had whispered breathlessly into his mouth and then broke away laughing and disappeared into the crowded room.
Everyone was drunk and Carolyn had flirted with some of the other men at the party so he had never followed up on the incident but the memory had fuelled quite a few wanks.
Now that was how women should dress! Like Carolyn Jones; not like some Hillary Clinton wannabe in pantsuits; or barelegged and 'cankled' in drab peasant-skirts and boring cotton blouses.
The transvestites in the pictures and videos he had found on Mike Harris's computer dressed like he believed women should; and he thought of the transvestites as women not as men. Even when they displayed their cocks! In fact seeing these women dressed up all sexy, with a boner sticking out from under their skirts made them all the more exotic and erotic.
He had masturbated so often over the course of the weekend that his cock was sore and the stocking he had stolen from Mike Harris's desk was now a sodden mass of laddered nylon.
By Sunday afternoon he was determined that he would have meet one of these sexy transvestites in the flesh. He didn't want to see the trannie transform from a man to a woman; he wanted to see her post-transformation. He didn't think that he would even want to touch her; he was no fag! But he wanted to see one up close and see if they were as appealing as they looked in the images on his screen.
He idly opened up another hidden folder, this one labelled: 'Michele', and flicked through the images. The transvestite in the images was attractive but the images were boring compared to the other X-rated files he had looked at. They were just pictures of the tranny, who obviously called herself Michele, dressed in different outfits. She was attractive and had great legs but she wasn't having sex with anyone like the trannies in the other pictures.
Brian was juts about to close the file when it hit him like a ton of bricks! The attractive transvestite on the screen before him was no one other than Mike Harris! Fuck! He looked closer at the image and sure enough it was Mike! He was totally feminised in the pictures and looked very attractive but when he looked very hard he could see it was Mike alright.
He sat back in his chair as a plan began to develop in his mind. By dinnertime that night he had his scheme hatched; he could hardly wait for tomorrow!
Mike Harris spent most of the weekend dressed as Michele Nylons, his transvestite alter ego.
Mike had started dressing in lingerie in his teens. During puberty had become fascinated with his mother's and sister's hosiery and underwear. He liked the feel, the smell and the look of the delicate garments and had initially just caressed and sniffed the various dainty articles that he surreptitiously stole from the laundry basket; he had then progressed to masturbating with them and had finally graduated to wearing them. He loved the feel of the sensuous attire against his skin and liked to look at himself in the mirror dressed in panties, hose and bra.
One day he even slipped into a pair of his mother's high-heels and had stood in front of her full-length mirror admiring himself, naked except for a pair of his mother's black satin panties, matching bra, taupe sheer-to-the-waist pantyhose and red high-heels.
His mother had come hope early and caught him.
"You naughty boy! I wondered who had been staining my underwear and ruining my best sheers!" she exclaimed and stormed into the room.
She sat down on the bed and pulled him roughly towards her and threw him over her knees.
"Now you'll get a spanking; just like I would give to a little girl who has been naughty," she hissed, and bought the flat of her hand down on his buttocks.
His bottom burned and he cried with pain and humiliation. He was mortified and distraught.
"Please don't tell daddy," he begged as his mother flailed away at his reddening cheeks.
"Oh shut up you sissy!" his mother replied, counting the strokes as she spanked her son's pantied ass.
After a while the pain subsided and much to Mike's chagrin he became aware that he was getting an erection. The feel of the satin panties rubbing against his penis, intensified by the feel of his mother's warm, nylon-clad thighs, overcame any feelings of discomfort.
The glans of his penis protruded above the waistband of his panties and his frenulum was rubbing exquisitely across his mother's sheer stockinged thigh. Despite his best efforts his erection continued to grow until it became obvious to his mother.
"Oh you little bugger!" she screamed and kicked her legs in an effort to dislodge him.
Her efforts backfired however and her son's hard shaft slid between her stockinged thighs and began to spurt torrents of hot semen all over her legs. It dribbled down her legs and pooled in her shoe, darkening the sheer nylon of her stockings as it soaked in.
Mike was crying and his mother screeched and flailed at her son until she eventually extricated him from her lap. He fell to the floor; the last of his spend soaking into the black satin panties he was wearing.
She stood up and clattered on her heels into the ensuite bathroom where she scrubbed her nylons with a damp cloth and then kicked off her heels and lifted her skirt and unhooked the damp stockings.
She threw the flimsy semen stained garments at her son.
"No one needs to know what happened here today son, especially your dad. It will remain our secret," she said coldly staring him in the eyes.
"You can keep the clothes you are wearing and my stockings that you just ruined; but you cease forthwith to borrow any of mine or your sister's clothes and shoes!"
"Do you understand?" she hissed.
"Yes mother," Mike replied meekly, his head bent and his penis slowly deflating.
And so it was; he and his mother never bought up the subject again. He would occasionally find his mother's or his sister's discarded nylons and underwear in the trash and he took them believing they were fair game as they had been thrown away; but he never again stole any of their lingerie.
He kept his little store of intimates hidden in his room and when he finally graduated college he left home as soon as he got job and could support himself. His mother threw him a little going-away party for him and gave him some presents; stuff that would be useful in his new apartment. He was quite surprised when he opened that last present; it was a small plastic egg.
It was a pair of L'eggs pantyhose inside their trademark packaging. His mother smiled and gave him a surreptitious wink. He didn't know what to make of the gift but he was glad to finally move out into his own residence.
The age of the internet had started to boom and Mike spent many hours researching his favourite subject: crossdressing! He found plenty of crossdressing sites and had soon added to his collection of female clothing so that he had quite a number of outfits. He bought a wig and some makeup and began to experiment. He shaved his body and used hair-removal cream on the parts he couldn't shave.
By the time he was in his late thirties Mike was an accomplished crossdresser and had adopted the name Michele Nylons to use when he was enfemme.
Mike took pictures of himself in sexy poses and added them to the thousands of images and videos he had collected off the web. He didn't consider himself gay; when he was dressed as Michele he thought like a woman so how was that gay?
He had seen a word used on some his favourite websites that accurately described him. He was a transbian; a crossdresser who is aroused by other crossdressers or transvestites but not by men. He was still attracted to women when he was in his male role and had had quite a few girlfriends; all of whom he had bought sexy lingerie and hosiery. He'd even had a girlfriend who let him wear pantyhose while he fucked her, but he was afraid to tell her the full story about his crossdressing peccadilloes.
Although he was now in his mid thirties Mike had still not summoned up enough courage to arrange a meeting with another crossdresser. He made do with looking at transvestite pornography and masturbated, sometimes while sucking a dildo or with a vibrator embedded in his anus, imagining he was having sex with another sexy transvestite.
Technically Michele Nylons was a virgin.
On Monday morning Mike was surprised to see Brian Davies prowling around his office. Brian usually didn't come in until a little later in the day; the privilege of being a boss. Mike fired up his PC and got himself a cup of coffee whilst the Outlook program downloaded his email. He sat at his desk and sipped coffee whilst opening his email. He was a little unnerved when he noticed that Brian Davies had stopped prowling his office and was now staring at him through the glass wall.
Mike shrugged his shoulders and opened the next email; it was from Brian and had two large attachments. Mike opened the first attachment and all of the blood drained from his face and he nearly fainted.
Mike's screen filled with the image of a mature woman stylishly dressed in a charcoal-grey business suit. The tight pencil shirt had a double pleat at the front and was split at the side with a kick-pleat framing a shapely set of legs encased in sheer taupe pantyhose. Her feet were shod in black high-heeled pumps; on one ankle a silver chain bracelet glittered. Her jacket was open and under the jacket she wore a mauve satin blouse; the lacy top of a black brassiere just visible at her décolletage. Silver necklaces and bracelets adorned her delicate neck and slim wrists; matching drop earrings adorned her ears, just visible through her brunette bob, which was highlighted with discrete crimson streaks.
Her mature but attractive face was heavily made-up; lashing of black mascara and eyeliner, and multi-hued eyeshadow enhanced her sparkling hazel eyes; her cheeks were rouged and her lips painted with plum-red lipstick. Her fingernails were painted with matching nailpolish.
She was posed front-on, standing with one leg thrust forward, ensuring a tasteful glimpse of thigh, one hand on her hip, and her lips pursed in a kiss.
She was Michele Nylons! She was Mike Harris in drag!
When he opened the next attachment his heart felt like it would explode. It was an image of two transvestites fucking; the same image he had printed on Friday afternoon and taken to the rest room to masturbate with.
Mike gasped and then his eyes flicked down to the email text.
'I think we need to discuss this, (signed) BD' it said.
Mike collapsed in his chair, gasping for breath; his mind reeling and his body trembling. He sat like that for two minutes before his Outlook program alerted him to an incoming email. It was from Brian Davies and the subject simply read 'Now!'
Mike managed to pull himself to his feet, and sweating and trembling, he slowly made his way over to Brian Davies' office. He went through the door and blurted out:
"Brian; I'm sorry, I'll resign immediately!"
"Not so fast Mike, close the door and take a seat," Brian replied, closing the vertical blinds on the walls of his office so they had complete privacy.
Mike sat down and waited for the derision and humiliation that was sure to come his way before Brian eventually fired him.
"Now Mike I'm not going to lecture you on the company policy about using the internet for accessing pornography."
"Nor am I going to bother to relate to you the details as to how I came to know about your peccadilloes; nice underwear you were wearing on Friday afternoon by the way," Brian sniggered.
Mike was mortified; the memory came flooding back! He had masturbated in the men's room and had forgotten to take the picture of the two transvestites engaged in flagrante delicto with him when he left! Brian must have been in the adjacent toilet cubicle and seen his feminine underwear bunched around his ankles!
"So Mike you see my dilemma here don't you?"
"Not only have you violated the firm's anti-pornography policy; you have also contravened several rules of the company's code of conduct!"
Mike dropped his head into his hands. The day he had dreaded had finally arrived! He had been caught in the closet!
"Of course I'll resign and write a letter of apology to the management for breaching the rules and regulations regarding the private use of the internet at work. I hope I can trust you to respect of my privacy regrading my penchant for female attire as that is no one's business but mine."
"Well you see Mike, or should I say Michele, you ain't gettin' off that easy!" Brian grinned.
"You see; as well as all of those lovely pictures of you dressed as Michele, and they are lovely by the way, I also have in my possession the contents of your email contact list."
"I'm sure your mom, dad, and family will be very happy to see their son dressed as Michele. Ah; what the hell; I'll just send the images to every name in your Outlook address book!"
"Then I'll send copies to all of the publishing houses in the state, as well the details of your breach of company policy."
"You'll be lucky to get a job at a newsstand!" Brian finished.
Mike blacked out for a few seconds and when he came too Brian was sitting on the edge of the desk and holding out a glass of water. Mike took the glass in trembling hands and sipped the cool liquid.
"How Much?" he asked.
"How much what?" Brian replied a little confused.
Then he realised what Mike meant.
"Oh! You mean how much money?"
"You silly girl I don't want your money!" Brian laughed.
"First off; I am not in the least bit gay; but those pictures have piqued my interest in transvestites," Brian said.
"For some reason they fascinate me."
"So here's the deal: I want to see you dressed up as Michele."
"Nothing kinky! I just want to see what a trannie looks like in the flesh."
"I might get you to pose and take a few pictures of you but that's the extent of my interest."
"As I have all of these pictures here; a few more aren't going to matter are they?" Brian smiled and held up his flash drive.
The wheels in Mike's brain cranked as he took on board Brian's proposal.
"And my job here?" Mike asked.
"You can keep your fucking job my friend; I doubt any of us will be employed here for much longer anyway unless the economy takes a sharp hike in the right direction."
"Give me the morning to consider?" Mike asked.
"You have until noon," Brian replied and stood up from his desk and began to open the blinds.
Mike left Brian's office and went back to his workstation. His mind was racing and various plans and ideas swam around inside his head but in the end they were all hopeless. Brian Davies had him by the balls! He could capitulate or lose his job and be exposed to his family and friends as a closet transvestite.
It would probably not surprise his mother, given the incident in her bedroom all those years ago. But his dad would be mortified; and his sister? How would she react? It wouldn't be too bad if Brian just knew about his crossdressing; but he had the pictures! Oh my God those fucking pictures!
If they got around he would be ridiculed for the rest of his life!
He opened up Outlook and sent off an email to Brian; it simply said: 'when?'
A few seconds later a reply came through.
'Tonight; your place at 8:00pm. Wear the same clothes you are wearing in that picture I sent you. I'll call your cell when I'm outside your apartment.'
'Don't fuck this up Michele (signed) BD'
The rest of the day dragged on for both Mike and Brian. Mike fretted and worried but by the time he left work, earlier than usual, what could Brian do - fire him; he was resigned to his fate.
Brian was worried that he may have gone too far. Batting off over images of sexy transvestites on the computer screen was one thing; but actually meeting a trannie in the flesh?
What did he think he was going to do with Michele? He wasn't going to touch her; she was a man!
But his growing obsession overcame his diffidence and he set his mind at rest with the thought that he would finally get to see a sexy transvestite in the flesh, take a few pics, and satisfy his curiosity. He wouldn't be doing anything in least bit homo!
Later that evening Mike made the mental transference into his enfemme personality: Michele Nylons. He had taken a long shower and shaved away a few rouge hairs on his legs and chest. As soon as he sat down to do his makeup his mind clicked over to 'femme mode' and he thought of himself now only as Michele.
Michele applied foundation and finishing powder followed by black eyeliner with and then pink and blue multi-hued eyeshadow. She rouged her cheeks and painted her lips with two-coat long-lasting plum-red lipstick. She then applied lashings of black mascara to her eyelashes and completed her makeup with dusting of finishing powder. She carefully painted her fingernails and toenails with plum-red nailpolish to match her lipstick.
Michele lifted the brunette bob wig off the wigstand and brushed it out and carefully adjusted it on her head so that it sat right. The fringe came to just above her pretty eyes and the nape touched her shoulders.
Michele stood up and slid her legs into a pair of sheer taupe pantyhose, carefully smoothing out the wrinkles. She pushed her penis under her crotch and used the gusset of the hose to hold it in place. She stepped into a pair of black satin full-cut panties and pulled on the matching brassiere with lace trim. She stuffed a set of expensive breastforms into the bra to fill the cups.
Next she stepped into the charcoal-grey pencil skirt with the double pleat at the front kick-pleat at the side. She put on her mauve satin blouse and tucked it into her skirt, zipping up the skirt and adjusting the waistband and the hem. The hem of the skirt tickled her nylon-clad thighs and sent a ripple of excitement though her body.
The excitement was soon quashed as she remembered who she was dressing for and why.
She sat down on the bed and slid her feet into a pair of black high-heeled pumps and then clipped a single silver ankle-chain to her left ankle. He heels clicked on the tiled floor as walked back to the mirror where she put on her silver necklaces and bracelets and clipped matching drop earrings to her ears.
She sprayed herself liberally with 'Poison' perfume including a couple of sprays under her skirt on the tops of her thighs. She pulled on her jacket and checked herself out in the full-length mirror.
Brian Davies sat in his old BMW outside of Michele Nylons' apartment block smoking a cigarette and debating with himself as what the hell he was actually doing here. He no longer thought of the person he was about to meet as Mike Harris, he thought of her as Michele Nylons.
He felt a trace of self-loathing but he was fascinated by the idea of meeting a sexy transvestite in the flesh. He almost wished he hadn't found all of those images on Mike Harris' computer because now he found himself compelled to keep looking at them. His cock thickened as he recalled the images of the sexy transvestites sucking and fucking each other.
"Christ!" he muttered, and flicked his cigarette out the window and got out of the car and locked the doors.
He opened his cell-phone and punched up Mike's number. It was picked up on the second ring.
"You ready?" he whispered into the phone.
In his apartment, dark now except for the light of a single lamp, Michele answered.
Michele had only a few seconds to consider her predicament before she heard a gentle rapping at her door. She was hoping that Brian would change his mind and not come tonight; she hoped that he would show a little remorse and compassion regarding her situation, but as expected, he hadn't. She set her resolve and looked through the peephole to check that it was Brian and then opened the door just enough to allow him to enter.
Brian entered the gloomy apartment and was immediately stuck by the delicious smell of Michele's perfume. He had not expected her to smell as good as she looked; but then again he hadn't really thought about it.
Michele looked gorgeous; the tight business suit accentuated her curves and the tight pencil skirt clung to the tops of her legs, the kick-pleat in the side displaying a pleasing glimpse of sheer-hosed thigh. Her hair and makeup were perfect and her clothes were very much to Brian's taste. Michele looked just how Brian liked his women to look.
Brian closed the door behind him and Michele turned and walked further into the small lounge room. Brian couldn't help staring at her shapely buttocks encased in the tight skirt and her long nylon-encased legs. The sound of her heels clicking on the tiled floor provided aural stimuli to compliment the wonderful sights and smells that stimulated his other senses. There was one sense left to stimulate; dare he touch her?
Michele barely made it into the lounge room when Brian reached out and pulled her around so that she faced him.
"I want to see you," he said, his eyes roaming over her body.
Michele trembled; she had never been in the company of another person whilst she was dressed. She felt Brian's eyes on her body. She felt a little nauseated and revolted by the situation; but, although she wouldn't admit it to herself, she felt a scintilla of satisfaction in the knowledge that Brian obviously found her attractive.
"Turn around for me! Slowly!" Brian ordered.
Michele complied and slowly spun around on her high-heels.
"Fuck you do look great!" Brian gasped.
"Well thank you I guess; what now? Can't you just leave?" Michele whispered.
"Like I told you I want to see some poses and them I'll go."
Michele nodded and self-consciously struck a couple of poses that she used when she had taken pictures of herself. Brian bought out his cell-phone and snapped some pictures using the camera feature.
She posed with one leg thrust forward and her head thrown back and then with her legs parted and her hands on her hips. Brian snapped away with his camera. After about five minutes Michele had run out of ideas.
"Ok Brian; you can leave now," she hissed.
"Oh no babe; I want to see a little more than that. I want you to lift your skirt for me."
"Oh come on Brian; I've done what you wanted of me. Please leave me alone," Michele pleaded.
"Get your fucking skirt up or I'll email these fucking pictures right here from my phone!" Brian answered angrily.
Michele reached down and reluctantly took the hem of her skirt in her fingers; her red fingernails contrasting nicely with her grey skirt. She slowly lifted the hem and revealed her shapely thighs; her sheer taupe pantyhose glistened in the lamplight.
Brian gasped and snapped away; he felt himself becoming erect.
"How far?" Michele asked.
"I want to see your panties," Brian replied.
Michele lifted her skirt until her black satin full-cut panties were visible; they covered the gusset of her sheer-to-the-waist pantyhose. Brian's cock throbbed and then the reality of the situation came back to him. This was not a sexy mature woman; it was a transvestite!
He took a couple more shots as Michele hung her head in shame.
"Ok; I think that's it," Brian said.
Michele gratefully lowered her skirt and walked to the door. She opened it a fraction and then stepped back. Brian put his phone away and walked over to the door, conscious of the bulge in his trousers.
"I hope that was it! Is it over now?" Michele whispered as Brian approached the door.
Brian stepped close to Michele and hissed into her face.
"It's over when I say it's over!"
The proximity of the provocatively dressed transvestite, the smell of her perfume, and Brian's state of arousal, overcame his reluctance to touch her. He reached out and pulled Michele into his arms and kissed her fiercely driving his tongue into her mouth.
Michele was caught off guard and she offered no resistance at first. Then she felt Brian grinding his erect penis against her body through the layers of clothing and she began to struggle. She tried to pull her face away from his but he followed her lips with his and rained kisses down on her painted lips. The smell and feel of the attractive woman in his arms was extremely arousing and any aversion Brian had to her being a transvestite disappeared.
Michele managed to break their kiss.
"Please Brian; please leave," she begged.
Brian's response was to drag her into the lounge, throw her on the couch and then fall on top of her. As she struggled underneath him Brian again pressed his lips to hers and began to savagely tongue-kiss her; his hands moved down to her legs and slid along her nylon-encased legs and disappeared under her skirt.
Her struggles only aroused him further and he ground his body against hers, rubbing his hard cock against her soft body. He managed to get his body between her legs and pawed at her tight skirt; hiking it up her legs. Michele kicked and hissed but Brian pinned her down with the weight of his body and stifled her screams with his kisses.
Michele wrapped her legs around Brian's torso and drummed her heels against his back and tried to flip him off her. This was her undoing; Brian delighted in the feel of her stockinged legs against his body and he reached down and unzipped flies and released his rampant penis.
Michele felt the hot spongy mass of Brian's cock humping her thigh and screamed into his mouth.
"Stop! Brian, stop this for god's sake!"
Brian was not to be discouraged and covered her mouth with his again and kissed her passionately whilst grinding his hips against hers. He loved the feel of her silken-clad legs against his cock; he moved around until his cock was positioned in the V of her panties and began to dry fuck her.
Michele stopped struggling when she realised that her struggles were only arousing Brian further. She lay still; her legs wrapped around Brian's body, while he humped her, his cock sliding along her satin panties. Brian reached down and slid his cock inside the leg opening of Michele's panties so that his cock was now trapped between the soft satin panty and the diaphanous nylon of her pantyhose gusset.
He thrust against her a few times and then he exploded. Torrents of scalding semen spewed from his penis and soaked into Michele's panties and pantyhose. Michele felt the hot viscous fluid seep through her panties and hose, scalding her sensitive skin. Brian groaned and humped away at her as his orgasm washed over him. He fluttered his tongue in her mouth and pulled her body hard against his as the last of his spend oozed from his cock.
Michele lay still as Brian slowly recovered from his climax. He eventually broke the kiss, extricated Michele's legs from around his body, and pushed himself up until he was kneeling between her legs. He looked down at Michele. She lay there with her skirt hiked up; her panties a sodden mess, white gobbets of semen pooled on the front panel of her black panties. Her hair was mussed and her makeup smeared. Black mascara ran down her cheeks. She was silently crying.
Brian grabbed a handful of her skirt and wiped his cock clean on it and then stuffed his deflating penis back inside his trousers.
Without a single word he got up from the lounge and let himself out of Michele's apartment.
Michele lay on the couch sobbing. She felt defiled and confused.
The front of her panties was soaked with Brian's semen. The crotch of her panties was flooded with her own semen; she had climaxed at same time as Brian.
Ma/Fa / Ma/Ma / NonConsensual / Reluctant / Coercion / Blackmail / TransGender / CrossDressing / Incest / Mother / Son / Spanking / Rough / Humiliation / Group Sex / Oral Sex / Anal Sex / Masturbation / Petting / Sex Toys / Cream Pie / BBW / Foot Fetish / Leg Fetish / Transformation /