The Devil You Know
By
Michele Nylons

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 just 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.

“Here!”

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.

Perfect!

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.

“Yes.”

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.”

Michele balked.

“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.

To be continued.

The Devil You Know - Part II
by
MicheleNylons©

Brian Davies sat at his desk struggling with his conscience as he remembered what had occurred the previous evening at Mike Harris' house. He didn't think of Mike as a man in drag; he thought of Mike as the uber-sexy transvestite Michele Nylons. But the outcome of his visit to Michele's had not turned out as he planned it; he had taken liberties with Michele that he had not intended. Or had he?

He admitted to himself that he had recently developed a fascination with sexy transvestites and that he was probably going to go a little further than just looking at her. Ok; so he had kissed her and dry-humped her! He hadn't penetrated her or touched her 'down there'. Brian was trying to rationalise his behaviour when two of the female office staff walked past.

Both were in their late thirties; one wore a baby-shit brown pantsuit with loafers; no makeup; her hair tied up in a bun. The other wore a drab shapeless khaki skirt that came to just above her ankles, flat heeled sandals, a featureless cotton blouse was buttoned to her neck, and a dab of makeup trying in vain to cover an enormous pimple on her cheek. She had mousy straggly hair. They chatted conspiratorially together as they walked past the glass walls of his office.

"I'd rather put my dick in a pencil sharpener!" Brian whispered to himself.

"Fucking women today!" he hissed.

Women today didn't seem to care about their appearance; as long as they were comfortable, fashion, sexuality and femininity seemed to be of no importance.

He scanned the office looking for Carolyn Jones; the sexy mature office manager who always dressed nicely.

She was leaning over a desk at the back of the office talking to one of the guys in sales. She was wearing a charcoal-grey business suit; her pencil skirt had a kick-pleat at the back. Her legs were encased in ultra-sheer skin-toned nylons that glistened on her shapely legs under the harsh lighting. He could see the cuffs of a mauve satin blouse peeking from the arms of her suit jacket; a gold bracelet glittered on her wrist and drew attention to her soft hands, long fingers, and her long red-painted fingernails.

She was standing on one leg; unconsciously swinging the other slowly back and forth; a black high-heel pump clicked on the tiled floor as her leg swung seductively back and forth.

Brian's cock hardened as he stared at the full-bodied woman. Then he had an epiphany. He realised that from the rear Carolyn, dressed in those clothes, looked very much like Michele Nylons had last night! That was probably the reason he found transvestites so fascinating; they dressed the way that he believed women should dress!

'Speaking of Michele Nylons; where was Mike Harris today?' he thought.

Brian called another member of team on the phone and found out that Mike had called in sick and was not coming into work for the rest of the week.

"We'll see the fuck about that!" Brian hissed as he replaced the receiver.

He was thinking about how he was going to handle the Michele Nylons situation whilst staring down at his desktop where a cold cup of coffee sat on top of an office memo. An idea began to germinate in his mind as he pulled the memo out from under the coffee cup. The memo was from one of the senior managers and instructed Brian to travel to Boston to meet with a counterpart at Houghton Mifflin; a rival publishing firm. Brian was going to blow the trip off and send one of the junior members of his team but now he had a plan. Road trip!

Michele Nylons lay under the bedcovers in her darkened bedroom. She had called in sick but what she really wanted to do was resign from her job and get as far away from Brian Davies as possible. She knew that it was going to be difficult; Brian had all of the contact details of her family and business acquaintances. Brian could fuck her over big time!

She thought long and hard about the orgasm that she had experienced when Brian had forced himself on her and had rationalised to herself that it was just an involuntary reaction bought about by physical stimulus over which she had no control. She equated it to the stories she had heard of rape victims who were made to experience orgasm by their attackers; they had no control over it; it was just their body's response; the victims still hated their assailants.

Deep down Michele thought it might all be a crock of shit. Deep down she thought she might have actually enjoyed being kissed, fondled and groped. Deep down Michele wondered why her throbbing cock was pushing against the sheer material of her pantyhose gusset as she thought about the experiences of last night.

Her cell phone rang. She reached for it and saw it was a call from the office. She debated whether to answer it but she finally relented.

"Mike Harris," Michele went into male mode.

"Hi honey; I missed you at work today," Brian Davis sniggered into the phone.

"You bastard! I'm never coming back to that place; I'm quitting!" Mike hissed.

"Now Michele! Haven't I explained to you the consequences if you disobey me?" Brian threatened.

"I'm sure your colleagues and family will love the happy snaps I took of you last night; particularly the ones where you are holding your skirt up for me."

"You are a fucking asshole!" Mike spat into the phone.

"Ok; pack a bag; we're going to Boston tomorrow. Bring something sexy to wear. Be at the airport at nine am sharp. Got it?"

Before Mike could respond the line went dead. Michele kicked off the sheets; she was wearing a satin full-slip, pantyhose, makeup and a wig, nothing else, and she padded into the bathroom. She shucked out of her nylons, used the toilet, and then stripped off her slip and removed her wig and makeup. She didn't always sleep like this; most nights she slept as Mike Harris, but last night she wanted the comfort of sleeping enfemme.

Mike took a long hot shower and thought long and hard about the situation he was in. After five minutes of tortured contemplation he punched the tiled wall in frustration. He was fucked! Brian had him by the balls unless he could somehow figure a way to blackmail Brian back. He thought about the coming road trip with increasing trepidation.

"Fuck him; Mike Harris is going, but Michele Nylons is staying at home!" he spat and a smile crossed his face.

The next day at the airport Mike met Brian near the check in counter. Brian threw a ticket at him.

"You're in coach!" Brian snarled and walked off to the first-class lounge.

Mike didn't see Brian again until he arrived at the Radisson hotel. Inside the ticket folder Brian had given him at the airport was an agenda for their business meeting at Houghton Mifflin, and a reservation slip for the Radisson hotel. Mike read the documents on the plane and caught a taxi to the hotel when he realised that Brian was not waiting for him at Boston airport.

Brian had gone ahead in a limousine and waited for Mike in an adjoining room on the eighth floor of the Radisson Hotel. As soon as Brian heard the muffled sounds coming from the adjacent room he unlocked the interlocking door and let himself into Mike's room.

"We gotta get going to the meeting soon but I want to see what you bought to wear later?" Brian demanded.

Mike shrugged and opened his suitcase and shook the contents onto the bed. Brian didn't see any woman's clothing as he rifled through the pile of clothing on the bed.

"What's this shit?"

"I told you to bring something sexy to wear!" he hissed.

Mike shrugged his shoulders and gave Brian a contemptuous look and then smiled.

"I guess I forgot," he grinned.

"Ok; I can see what's happening here and I admire your determination but just bear with me a minute will you?" Brian said and flicked open his cell phone.

He punched up a number on his cell phone and spoke into the phone.

"Hello; is this Mike Harris Senior?"

"Yes Mister Harris; this is Brian Davis; your son's boss. I'm calling to let you in on a little secret," Brian grinned evilly at Mike.

Mike paled and nearly fainted. His father was not well; he'd recently had a triple bypass and any form of shock was likely to put him back in hospital or maybe even kill him.

Mike pleaded in a hushed whisper.

"Ok, ok, ok.............anything! Anything you want; just don't tell my dad!" he begged.

Brian continued to grin.

"The secret is that your son is the best member of my team and I'm putting him up for a productivity award this month; I'll email you the pictures of him receiving the award," Brian said, sounding pleasant whilst looking at Mike with steely eyes.

Mike breathed a sigh of relief and sat down on the bed before he fell down.

"That's right; nice talking to you Mr Mister Harris." Brian snapped his phone shut.

"Ok; here's the deal," Brian said taking out his billfold and handing Mike a credit card.

"I'm going to the meeting alone. You're going to go out and buy yourself a wig, makeup, shoes and all the other shit you need to make yourself look like a sexy woman."

"Don't bother buying a skirt or a blouse; it ain't like I'll be taking you out to dinner," he sneered.

"I'll be back here at eight; you better look as good as you do in those pictures I downloaded off your computer or else!"

Brian slammed the door adjoining the two rooms behind him; he cleaned up, changed into a fresh shirt and left for the meeting.

Mike sat on the bed looking at Brian's platinum American Express card; spinning it in his fingers as he thought about how close he had come to his family finding out about his crossdressing. After a while he reached for the phone book and grabbed a pen and paper and began to write down addresses. He was quite surprised to find that he was smiling to himself by the time he had extracted all of the information he needed from the phonebook. He locked the door behind him, went down to lobby and had the doorman hail him a cab.

"The Prudential Center," Mike said to the cabbie.

At eight o'clock Brian left the bar and went up to his hotel room; he had taken a couple of drinks to settle his nerves and was shaking a little in anticipation. He showered, shaved, brushed his teeth and splashed aftershave on his face. He slipped into the complimentary bathrobe provided by the hotel; he was naked underneath it and his cock was already semi-erect with anticipation.

He opened the door adjoining the two hotel rooms. Michele's room was dim; lit only by the bed lamps. The exotic smell of perfume hung in the air. Brian's cock throbbed briefly and he looked around the room for Michele. The door to her ensuite bathroom was ajar spilling light into the darkened room. He padded over to the bed, his bare feet relishing the feel of the luxurious carpet pile; his senses heightened and his libido aroused.

"Your credit card and the receipts are on the bedside table," Michele called from the bathroom; in her falsetto voice.

Brian sat on the bed and picked up the pile of receipts from the table. He read through the receipts slowly becoming incensed as his arousal turned to rage. Gucci, Saks 5th Avenue, Aldo Shoes, Pandora Jewellery! The bitch had spent over two thousand dollars on lingerie, makeup, shoes and jewellery at stores in the Prudential Center. Then she had spent over five hundred dollars at Venus Cosmetics on a wig!

"You told be not to buy any skirts, blouses or dresses; so I didn't; I guess I saved you a few bucks," Michele called sarcastically through the bathroom door.

Michele smiled to herself as she put the final touches to her makeup.

'That will teach the fucker! He wants me to look feminine and sexy; well that costs money honey. He might hold the upper hand, blackmailing me for sex; but fuck him! He can pay the price' she thought.

"Get the fuck out here you bitch!" Brian called.

He was going to teach this smart-assed tranny a lesson she would never forget! By the time he was finished with her she would wish that she had never met Brian Davies. He would drive her around dressed in drag and make her return all the stuff she had bought piece by piece.

"Fucking cunt!" he hissed.

Michele stepped through the bathroom door and posed in the lamplight. Brian gasped and all thoughts of retribution took flight as he gazed at the magnificent sight before him.

"You like?" Michele grinned; a radiant smile lit up her face.

Michele was wearing a burgundy satin basque cinched at the waist and it accentuated her curves; she had not bought breastforms but her own small breasts filled the cups adequately. Her heavily made up face was framed by a blonde bob, the fringe cut straight across her brows; the nape falling softly to her shoulders. Gold drop-earrings glittered through the silky mane. Her pretty hazel eyes were exotically defined by black eyeliner, black mascara and multi-hued eyeshadow. Her high cheekbones were defined by rose-coloured rouge and her full lips were painted with glistening plum-red lipstick.

Michele's stood with one leg pushed forward and one hand on her hip; her long fingernails were painted with plum-red glossy fingernail polish which exactly matched her lipstick; gold bangles and bracelets glittered on both wrists and matching necklaces accentuated her pale décolletage and small breasts.

Brian's eyes travelled down Michele's body. A pair of red satin full cut panties peeked from under the black lace which decorated the bottom of her basque. Michele had made no attempt to gaff her sex organs and the front of her panties bulged slightly; surprisingly Brian's cock pulsed at the sight. The basque's suspender straps were pulled taut on Michele's creamy thighs; clipped to the welts of black silk stockings. The stockings were fully-fashioned with reinforced heels and toes and back-seams. A gold ankle-chain sparkled on one slim ankle; it contrasted with the dark sheer silken hose. Michele's red-painted toenails peeked seductively through the gauzy reinforced toes of her nylons; her feet were shod in leopard-print, stiletto-heeled mules.

'Poison'; Brian's favourite perfume swathed her body; Michele radiated femininity, sensuality and sexuality.

Brian took a few steps forward and pulled Michele into his arms and pressed her soft body against his.

"You cheeky bitch," he whispered into her ear; her silken hair tickling his lips.

"You naughty boy," Michele whispered back.

Michele slid her arms inside Brian's bathrobe and wrapped her arms around his warm hard body.

Michele had the day to think about where her relationship with Brian was going. She didn't like being blackmailed but the more she though about what had happened to her when Brian had forced himself on her, the more she came to realise that she had enjoyed it.

She had always thought of herself as a transbian, a transvestite who only likes other transvestites, but she now comprehend that it wasn't just her body's reaction to a forced stimulus; she actually got turned by being treated like a woman by a handsome man.

Brian shucked himself out of the bathrobe and stood naked; Michele's body pressed against his. He kissed her softly, relishing the taste of her lipstick on her pliant lips and the scent of her alluring perfume. Michele slid her tongue inside his mouth and slid her leg up and down Brian's; her stockings hissed against his skin.

Brian kissed Michele passionately and she dug her long nails into the flesh of his back and she felt him stiffen against her. Brian groaned as Michele reached between their bodies and gently took his hardening member between her fingers and slowly began to stroke him.

It was the first time Michele had touched another man's penis and she found the experience delightful. The soft outer skin covering his shaft was warm and sleek and covered the hard spongy mass of his shaft; his veins pulsed as Brian's cock thickened to her touch. She slid her hand along his shaft and tickled his frenulum with a fingernail sending shivers of delight through his body.

Michele felt Brian shudder and her own penis began to harden inside her satin panties and she pressed her groin against him and squeezed his glans. She gripped his penis a little harder and began to slowly stroke him; squeezing his shaft and glans sporadically to further excite him. She felt the first bead of pre-seminal fluid seep from the eye of Brian's penis and she smeared the lubricant along his shaft.

Brian squeezed Michele's buttocks through her panties and kissed her harder; exploring her wet mouth with his tongue. He felt her stiffen against him and was surprised that he found it exciting; it wasn't that he was a homo; he wasn't holding another man in his arms he was holding a delightfully sexy mature woman. The woman just happened to have a penis.

Brian let Michele stroke him until he was fully erect as he continued to massage and squeeze her yielding buttocks. Michele continued to rake Brian's back with her fingernails; responding to his fervent kisses she slid her stockinged leg up and down his and scraped her high-heel along his leg occasionally to contrast the feel of her silken hose. She smiled inwardly to herself; she was becoming quite the seductress!

Michele decided to try something a little different to determine how far Brian was prepared to take his newfound enthusiasm for transvestite sex. She took Brian's cock guided it to her satin-encased phallus and proceeded to slide his cock up and down her own erect penis.

They both groaned into each other's mouths and slowly ground their groins together. Michele could feel the heat and pulse of Brian's cock as it humped against her own panty-clad engorged member and Brian felt the throb of Michele's cock against his. He was close to coming but he had other plans. He'd been dreaming about this all afternoon.

Brian took his hands from Michele's buttocks and placed them on her shoulders and began to press down. Michele knew what he wanted and she too had been thinking about how far they would go tonight. She had often masturbated whilst sucking on a dildo imagining she was having sex with another transvestite. The fantasy had evolved as she had thought about during the day; and whilst she was dressing in the late afternoon she had wondered what it would be like to fellate a man.

She imagined the feelings of dominance and control that she would have over him as she knelt on the floor before him. Suckling him in her mouth would be both sexually exciting and empowering.

Michele broke the kiss and slowly sank to her knees, kissing and licking his hard body as she descended; stroking his smooth skin with her hands. She knelt before him; his penis at eyelevel bobbing up and down and throbbing with excitement. Michele tentatively slid out her tongue and speculatively licked the head of Brian's penis with the tip of her tongue. Brian moaned as he felt her slick wet tongue cautiously explore his glans.

Brian pushed his groin forward and his penis slid over Michele's lips. Michele found the taste of Brian's pre-seminal fluid quite pleasant and her own penis began to pulse. When Brian thrust forward and his cock smeared her lipstick she smiled; she was right! It was empowering.

Michele opened her mouth, and, lifting a hand up to Brian's erection; she guided it inside her mouth and clamped her lips over the shaft. She explored his glans with her tongue and then moved her hands around his body and grasped his buttocks and pulled his cock deeper into mouth. She sucked Brian's cock.

Brian began to hump Michele's face, relishing the feel of her lips on his shaft and her tongue slavering at his glans as his cock slid in and out of her mouth. He looked down to see the blonde fringe framing her pretty face; her eyes looked up at him with delight and pleasure as she sucked his hard cock. Her legs were parted slightly to maintain her balance and his eyes followed the dark seams of her stockings down her shapely calves to her leopard-print mules. He was in ecstasy and he felt his orgasm building.

Michele increased the tempo as she felt Brian's cock begin to throb. She could feel his orgasm approaching and she was a little trepidatious but she was considerably more curious about how this man's semen would taste. She removed a hand from his buttocks and placed her fingers around his scrotum and squeezed him; milking him of his seed.

Brian exploded in Michele's mouth; flooding it with hot semen. Michele fervently sucked and slathered at Brian's pulsating cock, swallowing his spend as it gushed forth into her mouth. Brian's knees buckled with the intensity of his climax and he placed his hands on the back Michele's and fucked her face enthusiastically; emptying himself into the pretty transvestite whore.

Michele realised that she too was close to climax; her cock was throbbing in her panties and aching for release but she didn't want to move her hands away from Brian's body. She was enjoying bringing this man to extremis with her lips, tongue and hands; it was exhilarating and powerfully erotic.

Michele swallowed the last of Brian's discharge and licked his cock clean as it slowly began to deflate. Brian reached down and pulled Michele to her feet and to her surprise he kissed her passionately with an open mouth. She tasted the remains of Brian's spend mingled with his saliva as he French-kissed her; wrapping her in his arms and muttering sweet sentiments into her mouth. Eventually his fervour ebbed and he broke the kiss; holding her in a warm embrace and gasping for breath.

"My God Michele; that was magnificent!" he whimpered into her ear; inhaling her perfume.

"Thank you darling; a girl like's to know she's appreciated," Michele giggled coquettishly.

She felt amazingly feminine and sexy. She was quite taken aback at how enthusiastically she had responded to Brian's advances. She was still peeved that he had blackmailed her and forced himself upon her, but if he hadn't done, she would never have experienced these wonderful feelings.

Brian led picked up his bathrobe and Michele excused herself and went into the bathroom to fix her makeup; her lippy definitely need some attention!

Brian called room service and ordered champagne and a plate of canapés and they arrived just as Michele re-entered the room.

"So; what are we on a date now? You told me you weren't going to take me to dinner but this is a little extravagant isn't it?" Michele said sarcastically.

"Behave Michele; after the beating you gave my credit card today you don't want to get too sassy," Brian replied, opening the champagne and pouring two glasses.

"But wasn't it worth it? Don't you like your sassy gal?" Michele laughed and pirouetted on her heels.

Brian reached out and pulled Michele across his knees.

"I'll teach you about sassy!" he laughed and playfully spanked her panty-covered buttocks.

Michele hardened slightly and Brian felt her stiff cock rub against his thighs. He reached under her and tugged playfully on her satin-sheathed member.

"Behave," he said and lifted her to her feet and pulled her down beside him on the bed.

He kissed her softly; one hand stroking her hair and the other exploring the welt of her stockings. Michele mischievously pushed him away.

"Time to eat, drink and be merry!" she said taking a glass of champagne in her hand.

They ate and drank; neither saying much; uncomfortable now with the situation in which they found themselves. After a while:

"Would you really have told my father and my colleagues about my crossdressing?" Michele asked, plaintively.

"I honestly don't know. All I know is that I became fascinated with you and I wanted you," Brian replied.

"To tell the truth; if you hadn't forced yourself on me, I would still be a transvestite virgin," Michele said.

"I would probably have never mustered the fortitude to arrange a meeting with another tranny; and I definitely would never have approached a man," she admitted.

"So; you like it?" Brian smiled at her and pulled her towards him.

They lay on the bed kissing and fondling each other; both becoming aroused again. Michele was still unsure where she wanted this relationship to go and she eventually pushed Brian away as his ardour began to intensify.

"I need to pee and fix my makeup again," Michele smiled and hopped off the bed and sauntered over to the bathroom.

Brian watched her ass sashay across the room and followed her long, silk-sheathed legs. Her red satin-sheathed buttocks peeked below the burgundy basque and her blonde hair draped down to her shoulders. The scent of her perfume remained on the bedclothes and Brian realised his cock was hardening again. He improved his erection until it was rock hard and then he jumped off the bed and followed her into the bathroom.

Michele was leaning over the vanity fixing her makeup when Brian came in and stood behind her. He put his hands around her waist and pushed his cock into the crevice of her panty-clad buttocks and began to hump.

Michele wriggled her buttocks trying to extricate his cock.

"Stop it you naughty boy," she giggled.

Brian did not stop; instead he pulled the gusset of Michele's panties aside and slid his cock into the crease of her soft creamy buttocks.

"Stop it!" Michele yelped; seriously now.

Michele had fucked herself many times with dildos and vibrators but she didn't think she was ready yet for anal sex with Brian.

Brian had other plans.

He wrapt his arms around Michele's waist and pulled her back against him and his glans probed her sphincter. Michele screamed and wriggled but Brian was too strong. He held her with one arm and his free hand snaked out and grasped a little bottle of moisturiser from the vanity shelf.

"Please don't do this Brian," Michele begged.

Brian ignored her and flicked the cap off the bottle and squeezed the cold creamy liquid onto his cock and poured the remainder down Michele's ass-cleft. Michele struggled and stamped her feet when she felt the cool viscous fluid on her ass.

Brian pushed forward and the head of his glans entered Michele's puckered bud. Michele was shocked and she quit struggling as Brian slowly slid the full length of his penis inside her until his groin pushed against her soft round ass.

Michele's back passage felt uncomfortably full and for few seconds she felt excruciating pain but as the lubricated invader slid inside her anus she began to experience wonderful feelings of sexual excitement that no plastic dildo could bring forth.

"Ohhhh!!!" Michele groaned.

"Yessss!!!" Brian hissed.

His cock felt like it was being squeezed by a tube of warm pliant satin; Michele's anus was tight and velvety. Michele could feel Brian's cock slowly pulsing inside her; expanding and contracting the walls of her anus, his glans stimulated her prostate, radiating rings of intense pleasure.

"Take it slow!" Michele whispered and slowly began to rock back and forth on her heels.

Brian took hold of her waist and got into the rhythm; slowly fucking Michele's tight ass. Michele began to increase the tempo as her anus dilated and Brian's cock rubbed against her prostate; small spikes of delightful stimulation emanated from her sphincter which was tightly clamped around Brian's turgid shaft.

"Oh fuck me honey!" Michele moaned and began to push back against Brian as he jackhammered in and out of her tight passage.

Michele's cock became semi erect and she took one hand off the vanity to try to stroke herself but she couldn't maintain her balance because of the intensity of the fucking. Brian saw what she was trying to do and, with his shaft buried himself inside her hot tight anal cavity, he reached around and squeezed Michele's penis through her panties.

"Ohhh!!!" Michele moaned.

Brian fucked Michele and she fucked him back; both of them moaning and groaning with the intensity of their passion. Brian squeezed and stroked Michele's hardening penis and the stimulation she felt from having her cock massaged through her satin panties amplified the rings of pleasure that radiated from her anus. She was going to come!

Brian's cock throbbed and he pulled her back hard against him with his free hand burying himself deep in her bowels as he frantically squeezed her cock. He unloaded inside her; his cock pulsing and juddering as his scrotum contracted and forced steams of hot semen to spurt for his pulsating penis. Michele felt her back passage flood with Brian's sperm and this triggered her own orgasm.

A dark stain spread across the front of her panties and then a puddle of warm white semen formed on her panty-panel as her spend soaked through the diaphanous fabric. Brian reached inside her panties and smeared the hot come over her shaft and milked her of the last of her seed.

They remained locked together as they shuddered and gasped; their orgasms slowly subsiding. Brian slid his deflating member out of Michele's anus and roughly spun her around. He kissed her forcefully and she responded by hiking her ass up on to the vanity bench and wrapping her legs around him, pulling his body close to hers. Warm semen trickled from her anus and soaked into the rear of her panties; the front of her panties, already soaked with her own come, absorbed the few remaining dribbles of Brian's semen as it oozed from the eye of his cock.

Michele slid her stocking-sheathed legs up and down Brian's torso and pulled him harder against her; her fingernails raked his back as their lips crushed together and their tongues intertwined. Michele drummed her heels against Brian's hard buttocks and then pulled her face away from his; gasping for breath.

"We need to talk," Brian said.

They talked late into the night; stopping now and then to make love. By the time the sun crept across the room and woke them, it was late in the day.

Mike flew back home first-class seated next to Brian and they continued to talk and refine their plans for the future.

Two months later Mike Harris sat behind the desk in the office of the online publishing company he had set up with Brian. He had his feet on the desk and he was checking out the ample behind of Carolyn Jones who was bent over the bottom drawer of a filing cabinet. They had made Carolyn an offer that their previous employer couldn't match and she had joined the three-person company as a partner.

Mike allowed the leg of his pants to slide all the way up his calf revealing sheer taupe pantyhose. He wore pantyhose and panties under his male clothing all the time now and as soon as he got home he immediately transformed into Michele. He and Brian shared a house and on most nights they shared a bed.

Carolyn stood up and walked over and perched her shapely ass on the edge of his desk.

"Mike; I notice you make no secret of the fact that you wear nylons under your trousers. Is there something you want to tell me about?" she smiled.

"As a matter of fact............" Michele replied.

Later that evening Brian returned home. He preferred to arrive home after Michele so that she had time to transform. He let himself in and was surprised to find the house was dark. There was a sliver of light coming from the slightly-ajar bedroom door.

"Michele?" Brian called as he approached the door.

What he saw when he opened the door both astonished and excited him.

On their king-sized bed Michele was lying on her back dressed only in panties, bra, stockings and heels; her heavily made up face framed by a black bob was contorted in ecstasy. Kneeling between Michele's legs was Carolyn Jones dressed in a black bustiere, black seamed stockings and black high-heeled pumps. Her makeup was dishevelled and she was sweating profusely.

Carolyn was wearing a large strap-on dildo and was fucking Michele in the ass with enthusiasm; both of them were grunting and panting.

Michele turned her head and grinned at Brian.

"Are you going to get over here and join us; or just stare at us all night?" she smiled.

A few minutes latter, as Brian slid his cock inside Carolyn's buttery quim, he thought to himself how lucky he was to have two gorgeous women in his life.

When Brian's cock slid inside her, Carolyn didn't miss a stroke; she continued to enthusiastically fuck Michele in the ass as Brian began to enthusiastically fuck her sopping cunt.

The End