Danny sat at the bar of the Holiday Inn nursing his fourth double scotch, espousing to the man beside him the reasons why his company was the best designer and distributor of accounting software in the world.
Danny was a large man in his forties and was running to fat. He was dressed in a travel-weary navy-blue business suit, a crumpled white shirt now open at the neck, and a ratty tie. He was attending a convention for accounting software distributors at the hotel, and he mistakenly believed that the well-dressed black man to whom he was imparting his knowledge of software design and distribution was attending the same convention and that he gave a shit about what Danny had to say.
Danny was also complaining about his travelling companion and business associate Mike, who he said, spent most of his free time locked in his hotel room whenever they were on the road together.
"Unsocialable asshole!" Danny ranted on, "he hardly ever comes to the bar with me after we have finished for the day; he just heads for his hotel room and locks himself away for the night."
"Well screw him pal! Work hard and play hard I say!" Danny said through a cloud of boozy fumes.
Mike had his own reasons why he didn't like to socialise with Danny when they were on the road together. One reason was that in Mike's opinion, Danny was only a few drinks away from becoming a full blown alcoholic. The second reason was a closely kept secret.
Whilst Danny was in the bar getting drunk and boring to death the well dressed black man sitting beside him with stories of accounting software sales and criticising his travelling companion; Mike was sliding a pair of expensive sheer-to-the-waist pantyhose up his carefully shaved legs. Yes; Mike had a very good reason he didn't want to be anywhere else except inside his hotel room tonight. Mike was a closet crossdresser!
Mike; or Michele in his femme alter ego; liked to dress as a woman. She occasionally met with other crossdressers but this didn't happen very often, and Michele considered herself a virgin, as except for a little nervous foreplay with other crossdressers, she had not yet had a sexual experience whilst dressed as a woman.
When on the road Mike kept a travel bag hidden inside his suitcase. The small travel bag contained a skirt, blouse, high heels, lingerie, cosmetics, jewellery and a wig. Mike had become adept at packing the minimal requirements to transform into Michele inside the small soft travel bag and hiding it discretely inside his larger suitcase.
He sometimes had nightmares where one the 'Travel Nazis' who provided airport security screening inspected his suitcase and opened the travel bag and held up his female requisites for everyone in the airport to see whilst demanding to know why Mike had ladies clothing secreted in his suitcase.
Of course this had never happened, and it was highly unlikely to happen, but a little paranoia is common amongst most closet crossdressers.
So whilst Danny engaged the well-built black stranger in inane barroom prattle, Mike concentrated on transforming into Michele. She had already applied heavy makeup and fitted her favourite brunette bob wig. She smoothed out her nylons, carefully pushing her penis under her crotch so the gusset of the pantyhose would hold it there.
Michele stepped into a pair of red boy-leg satin panties and then pulled on a matching bra. Unable to bring her breastforms with her on the road, she stuffed the cups with balled up pantyhose; a poor substitute but adequate for the task. Next she slid a cream coloured nylon half-slip up her legs, exhilarating in the sensuous feel of the slip against her hosed legs, and adjusted it so that the hem rested about six inches above her knees.
She didn't really need to wear the slip as a foundation garment but she loved the feel of the slip against her hosiery and panties.
Michele buttoned up a teal coloured satin blouse, cursing under her breath because even after all this time dressing as a woman she still had difficulty with the buttons because they were on the opposite side to a man's shirt. She stepped into a navy-blue A-line skirt; closed the zip and adjusted the waist. She smoothed out the skirt so that the hem sat just below the hem of her half-slip. The skirt had a kick pleat in the rear and her slip would show but as she was spending the night alone that didn't really matter.
She slid her feet into a pair of black leather four-inch high-heeled pumps and opened up the small cosmetics bag and took out the small bottle of Poison; her favourite perfume. She sprayed herself liberally with the scent and giggled as she sprayed a couple of squirts under her skirt. There would be no one to appreciate it of course; but Michele liked to dress as feminine as she could.
She adjusted her makeup; applying another coat of plum-red lipstick. If she was at home she would use her favourite 'Estee Lauder Pure Color' two-coat long-lasting lipstick; but on the road, regular lipstick sufficed and was a hell of a lot easier to remove. She clipped on gold earrings and a matching necklace, bracelets, and rings on three fingers of each hand. Then she reached down and fastened a gold ankle-bracelet around her nylon-sheathed ankle.
Although Michele was dressing purely for her own pleasure, she liked to look as femme as possible and paid attention to detail. Of course at home she would wear a garter belt and stockings instead of pantyhose and paint two coats of nailpolish on her toe and fingernails, but on the road, with the ever-present chance of being disturbed, she made sacrifices so that she could quickly wash off her makeup and get out of her clothes if she had to. She was also limited by how much space she had in the travel bag.
Occasionally Michele had met up with other crossdressers whilst she was travelling; usually at their house or at a different hotel than the one she was staying in with Danny; but these occasions were very rare and mostly she just dressed, surfed the net for transgender websites and sometimes fired up her webcam for some online fun. The evening usually ended with her masturbating whilst fantasising about being with another crossdresser or; very rarely, she might jack off on the webcam at the request of another crossdresser.
Michele eyed the small bottle of nailpolish lying unused in the cosmetics bag with regret and then she reached in and grabbed it.
"Fuck it! I'm going to do my nails." She said to herself as she sat down on the bed and poured herself a gin and tonic from the minibar and prepared to paint her nails.
Michele rarely painted her nails when she was on the road as it was very risky if she had to leave the hotel room in hurry. Washing off her makeup and shucking out of her femme clothing could be done in a few minutes but removing nailpolish took time. She didn't have room for nailpolish remover in her small bag so she would have to clean off the nail polish with vodka from the minibar which could take quite some time to do properly.
Also Danny insisted they book adjoining hotel rooms and it was not unknown for him to return to his room late at night drunk and hammer on Mike's door insisting that Mike join him for a drink. A few times Mike, fully dressed as Michele, had had to shout some made up excuse through the closed door as to why he couldn't join Danny for a drink.
Michele sat on the bed and carefully painted her fingernails with a single coat of plum-red nailpolish. 'Important that a girl's nailpolish and lipstick match, ' she thought to herself.
Half an hour later she was seated at her laptop computer, her body illuminated by lamplight in the darkened hotel room, chatting online with other crossdressers and transmitting her image via webcam to a Yahoo chatroom whilst also surfing transgender websites.
She didn't realise that events were about to unfold that would change her life forever.
At the same time that Michele made the decision to paint her nails, the well-built, well-dressed, black man decided he was going to rob Danny.
The black man's name was Ronnie and he was carefully dressed in the business suite so as to look like any other businessman at the hotel bar; but he was in fact an accomplished thief and robber. His accomplice, Jermain, waited outside in the car. Ronnie's modus operandi was to befriend a gullible businessman at a hotel bar, drug him, and then pretend to help the businessman to his room, where he and Jermain robbed the unconscious victim of everything worth stealing.
Ronnie looked around the bar, and certain that no one was watching, he emptied a small vial of powder into Danny's drink. The strong sedative instantly dissolved and within a few minutes of Danny returning from the toilet and gulping down his drink he was unsteady on his feet and feeling incredibly sleepy.
"Let me help you pal," Ronnie said, sliding a strong arm around the fat drunk and guiding from the noisy bar to the elevators in the foyer.
"What room are you in?" Ronnie asked Danny, and when Danny answered Ronnie flicked open his cell and called Jermain.
"We're on! Room two one four; see ya'" Ronnie said into his cell and snapped it shut and put it away.
Danny was now at the pint where he could hardly stand because of the combined effects of the booze and drugs and Ronnie struggled to hold him upright in the elevator while he rummaged through Danny's pockets until he located his hotel room key.
.... There is more of this story ...
Ma/Fa / Ma/Ma / NonConsensual / Reluctant / Rape / Blackmail / Drunk/Drugged / TransGender / CrossDressing / Fiction / Rough / Light Bond / Humiliation / Sadistic / Gang Bang / Interracial / Black Male / White Female / First / Oral Sex / Anal Sex / Masturbation / Size / Foot Fetish / Leg Fetish / Violent /