The Devil You Know Ch. 01

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.