Maid to Order Ch. 02

Mick had been shit unlucky. He had driven over sixty miles on the day she bought all of his girly accoutrements. He had even stayed overnight, confident that she wouldn't run into anyone that he knew while he was shopping.

But, as has been said, he was shit unlucky. Of all the people in the world who happened to be in the same city, shopping in the same shopping centre, at the same time was his father-in-law Bill. Bill had been away overnight to play in a regional darts competition and had gone to the shopping centre to browse before driving home.

Bill saw Mick coming out of the shoe store and began to approach him to say good day. He saw the beaming smile on Mick's face and something instinctive inside told him to back off so he ducked into another store where he could keep an eye on his son-in-law unseen. Something was going on here; why was Mick leaving a ladies shoe store with a large bag smiling like he'd won the lottery?

Bill followed him to the car park until he saw Mick approach his car then he ducked behind another car until Mick had deposited his purchases on the back seat and locked the car. Decisions time; check out the car or keep following Mick? He was definitely up to something secretive.

Bill raced over to Mick's car as soon as it was safe to do so. The big bag had spilled its contents and lying on the back seat were three shoeboxes. Bill read the labels on the boxes and sure enough they were ladies high-heels, size 10.

"What the fuck? Has Mickey boy got himself a girlfriend?" he pondered.

He quickly picked up the trail and followed Mick into the department store. It was difficult to remain concealed, particularly as Mick appeared very cautious, constantly looking around. It was made harder because the large store had so few customers. With some difficulty he was able to hide behind the racks, shelving and displays and was amazed to see Mick select the cosmetics and lingerie and take it to the self-serve checkout. He knew where Mick was going, to his car, so he waited at the carpark entrance for him to return and followed him to the same department store.

Bill watched Mick for about thirty minutes and was now pretty much convinced that his growing suspicion had been confirmed. Mick wasn't buying this stuff for a girlfriend; he was buying it for himself!

Bill broke off his surveillance and checked his watch. Good, the pubs were open. He needed a pint and a ciggy so he could do some serious thinking.

Bill sat sipping his pint in the nearly empty pub and his thoughts drifted back in time.

About seven years into her twelve year marriage, his daughter Cynthia had told her mom about Mick's tights, slip, and knicker fetish and she had told her husband. Bill hadn't believed it at first.

"Bollocks! He's in the fucking army! They don't have Nancy boys in the army!" had been his response.

"You sure the dopey cow doesn't mean that he likes her to wear the sexy tights, knickers and slinky stuff. You know, like I like you to do," he grinned sliding his hand under his wife's skirt, stroking her thighs and buttocks.

"Piss off! She said he likes to wear them himself and that he wears them to bed on his own sometimes," his wife retorted.

"Anyway, none of our business. Each to their own," she grinned and encouraged her husband to explore inside her knickers.

"Now take me upstairs and give me a good shagging," she giggled.

They hadn't spoke of it again but Bill recalled the conversation as he sipped his pint.

"That could explain it I suppose?" Bill muttered to himself.

Bill thought he knew better. Bill thought he knew better because he was a secret transvestite admirer and had been for years.

It all started when Bill was in his early twenties and had gone on a drinking binge in Manchester. He and his mates had ended up in a dingy disco, pissed and looking for easy sex.

Bill had zeroed in on a big-boned middle-aged stunner in a sequined mini-dress, too much makeup, big hair, fuck-me heels and stocking-clad legs longer than Sackville Street (and this was long before Sparkle). Her name was Linda and he chatted to her, buying her gin and tonics and admiring her many attributes until she succumbed to his advances and went back with him to his sleazy hotel. He was so pissed he didn't know she was a transvestite until they got to the room.

He kissed the woman and she slid her tongue into his mouth and she ground herself against him, they embraced and fondled each other his hand going straight under her dress and caressing her stocking-tops and creamy thighs. His hand slid further up her leg and slid across her satin panties his fingers seeking her moist crevice. Instead they found a hard lump held in place by a gaff.

Bill wasn't sure if it as the alcohol or his sexual inquisitiveness but he wasn't perturbed; surprised yes, but still highly sexually aroused. He rubbed the hard flesh through her panties and groaned with lust.

"My god, I would never have guessed you were a trannie," he moaned and kissed her passionately.

"Do you like transvestites love, I thought you knew?" the attractive transvestite giggled drunkenly.

"Oh fuck yeah baby, I do now" Bill responded, excited about his first upcoming trannie experience.

Linda slavered her tongue around in Bill's mouth as his erection rubbed against her through her clothing. She manoeuvred a hand between their bodies and squeezed Bill's penis through his jeans. Bill groaned and pushed her back onto the bed and fell down on top of her, never breaking their kiss.

He humped away at her, his need for release overwhelming. Linda reached between their bodies and opened his flies and freed Bill's cock from the prison of his trousers and Bill shuddered. She produced a condom packet and a tube of lubricant from her purse while Bill removed his jeans and then slid the condom over Bill's throbbing phallus. She slathered his latex-clad phallus with the lubricant.

Bill didn't even remove her panties; he simply slid the gusset to one side and then slowly slid his entire length inside Linda until his scrotum rested against her buttocks. Linda grunted as Bill's cock filled her and his cock quivered as her anus gripped his turgid member.

Their fucking was almost savage; Bill pounded away at Linda as she rose her buttocks up off the bed to meet his thrusts. They never broke their kiss and they gasped and groaned into each others mouths as their tongues entwined and teeth occasionally cracked together with the ferocity of the sex. Bill had managed to shuck off his shirt and when Linda bought up her legs and wrapped them around him he savoured the feel of Linda's stockings rubbing against his skin.

The fucking became a frenzy, Bill jack-hammered his cock in and out Linda's tight anus and Linda, impaled on Bill's hard throbbing cock, clung to him and wriggled and shook her arse. She thrust her hips upward to match his strokes ensuring his full length penetrated her slick anal sheath and crossed her ankles behind Bill's back, her stockings hissing as they rubbed together and against Bill's sensitive skin.

Bill howled and moaned with the rush of his climax and filled the condom with his hot seed. Linda's cock was erect and rubbing against Bill's stomach through the flimsy material of her panties as Bill savagely fucked her. The pressure and friction induced Linda's own climax and she groaned in ecstasy as she flooded her panties with hot semen. Bill was surprisingly not disgusted and relished the fact that his fucking had invoked an orgasm from the gorgeous creature that lay under him.

Bill's thrusting slowed down as his orgasm subsided and eventually he lay still on top of Linda with his slowly deflating penis buried in her anus. He was still kissing Linda and he could tell that her orgasm was still raging through her body, he felt her penis convulsing in her panties and her hot seed flooding through the panty material, soaking his belly.

Bill and Linda lay in each other's arms, they were not concerned that her emissions were soaking into the cheap hotel sheets.

"Your first time with a transvestite, really?" Linda asked.

"But not my last babe, that was fantastic! I've never been so turned on before," Bill replied.

"So, if I may ask? Why does a bloke want to dress like a girl and have sex?" Bill posed, getting up to get them both a can of lager and a cigarette.

"Well its different for all of us but my story is that I started to wear knickers, tights and slips as a young boy" Linda began.

Linda told Bill her story about how she had a compulsion to crossdress at an early age and where that had led her. About thirty minutes into the saga Bill found himself becoming aroused again; surprised given his alcohol intake, and shut her down by falling on her again and giving her another good shagging.

Bill slipped her a tenner for a taxi and sent her on her way in the wee hours. He wasn't really interested in her story, he had just found out that he had developed a new compulsion; to fuck crossdressers.

That night, as he drifted off to sleep, he decided this needed some further exploration.

Over the years Bill had nipped out of town to go to transvestite friendly venues and had often scored an interlude with a becoming crossdresser.

Sitting in the pub drinking beer and smoking cigarettes he pondered the current situation and remembered the story Linda had told him about how she became a transvestite having developed a fetish for wearing knickers, tights and slips at an early age.

So Mick was now progressing from being a knicker and tights wearing Nancy boy to becoming a full on crossdresser. Or was he already a secret transvestite and Bill had caught him on a shopping spree. Anyway it didn't matter. What mattered was that there was now a closet transvestite living close to him and Bill knew her secret. Bill wondered what Mick looked like in drag. He certainly intended to find out!

Two weeks later on a Saturday night Bill went out telling his wife that he was going down the pub as usual and not to wait up for him.

"As if?" she scowled.

"You'll come home reeking of beer and cigarettes and fart all night any way. Sleep in Cynthia's old room," she yelled at him as he headed for the door and then turned back to the telly to watch a re-run of Coronation Street.

Bill drove the short distance to his son in law's house and parked one street over. He walked past Mick's house and noticed that it was effectively blacked out; a single shard of light was visible from a crack in the curtain at one of the side windows. He noted Mick's car was in the driveway so he was obviously home.

Bill vaulted the fence and made his way silently to the side window. He stood perfectly still for five minutes and when he thought it was safe he peeked in through the window looking inside through the small gap in the curtain.

He was amazed at what he saw.

An attractive, tall, slender woman with fantastic breasts and legs stood in the lounge drinking a glass of wine. She wore a black bob and her eyes were smoky with eyeshadow, eyeliner and mascara, her cheeks were rouged and her lips ruby-red with glossy lipstick framed her pretty face. The red dress clung to her body and then flared slightly at her trim waist, the hem caressed her stunning legs clad in sheer black fully-fashioned stockings and her feet were shod in black patent-leather high-heeled pumps. She had accessorised with gold earrings, necklace, bracelets and rings.

Bill's cock hardened in his trousers at the sight of the stunning transvestite.

He took his phone from his pocket, selected the camera app and set it to video and recorded Michele as she sipped her wine and paraded around the lounge room striking poses to amuse herself. Then he took a series of still pictures and looked at the files he had recorded and smiled.

Michele had spent the last two weeks locked in the house experimenting with makeup, trying on various outfits and wigs, practicing walking in high-heels and talking in a smoky feminine voice.

Tonight she had dressed in the red dress, which had now become her favourite and she was flouncing around the living room when all of a sudden the front door opened and Bill crashed into the room.

She wanted die, she wanted to crawl under the table and cry, and she wanted to be anywhere but here.

"Hello Mick, or what are you calling yourself now?" Bill grinned.

"Oh my fucking god Bill! What are you doing here?" Michele was appalled.

"Don't panic dear, your secret is safe with me," Bill said.

"Fuck! Fuck! Fuck!" was all Michele could cry.

Bill casually walked over to the sideboard where a bottle of Shiraz was opened and poured two glasses.

"So what do you call yourself, I can't keep calling you Mick while you stand before me looking so femme and I have to say downright sexy."

Michele was more confused than she had ever been in her life.

"Err Michele; that's what I call myself," she whimpered.

"Come sit," Bill patted a seat on the couch and offered a glass of wine.

Stunned, Michele sat on the couch, demurely pulling her hem down and crossing her ankles. She had been practicing feminine traits and they were now coming naturally to her when she was dressed.

"Look don't worry. You will be surprised to know I know quite a bit about transvestism," Bill explained.

He offered her a cigarette and lit it for her and lit one himself.

"Michele, I saw you at the shopping centre a few weeks ago and was going to say hello when I realised what you were up to. Well I did after I saw what you were purchasing and after some serious thinking."

"I'm what is known as a transvestite admirer; you have heard of them?" Bill asked, taking a gulp of wine and drawing on his smoke.

"Well my understanding is, they are men who find transvestites attractive, err, sometimes sexually attractive," Michel replied, still using the smoky femme voice she had perfected.

"Yes that's right. Now let me tell you a story about when I was a lot younger and went to Manchester to get on the piss with some of my mates," Bill said.

He told Michele about his encounter with Linda. He wasn't too graphical about the sex but said they had had a good time at the nightclub and hinted they had gone back to his room for a romantic interlude.

Michele was both fascinated and shocked at Bill's story. And when he told her he continued his pursuit of transvestites and crossdressers throughout his marriage she became a little concerned. Where was all this going?

"Well that's fascinating Bill, but what has any of that got to do with me?" Michele asked, crushing out her cigarette.

Bill inched over and sat closer to Michele, almost shoulder to shoulder. Michele was now feeling entirely uncomfortable. Michele flinched when Bill reached into his pocket but was relieved when all he did was produce his phone.

"Michele; all our side of the family know about your tights, slip, and knicker fetish, Cynthia told us. And I'll bet your side of family know about that too, am I right?"

"My fucking bitch sister couldn't keep her mouth shut!" Michele replied.

"Yeah, so it's a family secret that know one really cares about," Bill said, lighting another cigarette and passing it to Michele.

He lit one for himself and blew out the smoke in a long hard drag.

He picked up his phone from the coffee table and played with the apps.

"But this. This is something completely different. This is a secret of monumental proportions"

Bill played the video of Michele prancing around the lounge room and then showed her the series of still pictures he had taken.

Michele paled and gulped at her wine. She began to shake.

"There, there darling. Your secret is safe with me. We just have to come to a suitable arrangement, that's all."

Bill pressed himself against the trembling transvestite and put his arm around her shoulders. His free hand found her knee and began to slowly stroke her, slowly progressing up her nylon-clad thigh.

Michele began to sob.

To be continued...