Chapter 2

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 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 it 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.