The Transvestite Stalker

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Man takes an attractive woman hostage, a surprise ensues.
5.6k words
4.38
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MicheleNylons
MicheleNylons
3,912 Followers

The man sat at a corner table in the coffee shop surreptitiously eyeing off the woman sitting on a stool at bar. She was dressed in a navy blue suit; her jacket was open, revealing well-formed breasts swelling her white satin blouse, which opened to the second button so that a hint of lace bra was displayed. Her legs were crossed and her skirt had ridden up revealing most of her well-formed thighs atop long legs encased in sheer flesh-toned hose. He thought he could make out a subtle seam running up the back of one of her legs and she dangled a black patent leather spiked stiletto from one foot, exposing a reinforced nylon heel. He also thought that the top of her hosiery where it disappeared under her skirt was of a darker hue; most likely the shadow welt found on expensive stockings.

'Slut! Sluts wear stockings! Sluts dangle their trashy 'fuck-me' high heels! Sluts like her wear too much makeup and show off their tits! Fucking slut! She deserves what she gets! They all do!'

His sick fevered brain was like a radio that he couldn't turn off. Sometimes there was just static, sometimes he played music and sometimes the announcer ran a commentary like now, while he stared at the voluptuous middle aged woman.

"Slut!" he hissed.

It came out as an involuntary whisper and he quickly looked around to see if anyone had heard him say it. Sometimes he unconsciously regurgitated what the radio in his head was playing; more often these days than was safe. His thoughts once again turned to the elegant woman sipping coffee at the bar.

'She's a slut alright and she deserves what she gets!' the psychotic commentator announced in his deranged brain.

He held up a newspaper to disguise his furtive surveillance of the woman. The headline banner proclaimed:

'POLICE STILL STYMIED BY CHELMSFORD STALKER'

The story beneath read:

'Police are asking members of the public to come forward with any information they may have that may assist them with their investigation into the man who has become known as The Chelmsford Stalker.

He is known to have committed six assaults over the last three months on middle-aged women who were home alone and police suspect there are other victims who have not come forward.

The victims are usually single, middle-aged, middle-class women; but in one case the woman's husband was away on a business trip. The Stalker broke into the women's houses and held them hostage overnight, repeatedly assaulting them then robbing them before tying them up and leaving. So far police have been unable to identify him by his DNA or fingerprints so they have determined he is not in their criminal databases.

"We need help from the public. This man will keep doing what he is doing until we catch him or until he moves on to commit similar crimes elsewhere." Inspector Jean Burgess of Chelmsford CID said in a press interview this morning.'

(What the newspaper did not reveal was that the team of young detectives led by Inspector Jean Burgess derogatory called the perpetrator, 'the MILF Fucker' or 'the Cougar Shagger', in reference to the fact that all of the middle-aged victims were attractive, well dressed and in at least two cases, promiscuous.)

The story went on for three more columns; rehashing the previous crimes, dwelling on the known facts and speculating on the atrocities inflicted on the women. 'If it bleeds - It leads' as they say in the newspaper business.

The Chelmsford Stalker watched the woman; his trousers tented by a throbbing erection as his eyes flicked from her attractive face with those smoky eyes and ruby-red lips, to her heaving breasts, then down to her stunning legs.

'The cunt is dangling that shoe on purpose! She wants you to look at her! She wants you to touch her! She wants you to fuck her!' the radio assured him.

The Stalker's radio began to play Midnight Rambler by the Rolling Stones and he quietly hummed the tune to himself as he stared at the woman.

Michele sipped her coffee enjoying being out and about dressed up to the nines. She had been a closet transvestite right up until her mid thirties and then become confident enough to go out dressed. She was now seldom dressed in drab, being single and living alone she could remain dressed enfemme 'twenty four seven, three sixty five', as people were want to say nowadays.

She never dressed conservatively. Why should she? She knew she looked stunning when she was dressed up, so why dress down? She liked the attention she drew and she didn't mind the odd dalliance now and then either. With the right man of course. She made no attempt to hide the fact that she was a transvestite, quite passable with a convincing 'Bonnie Tyler' voice, but up close she could be clocked.

She had an idea that the man pretending to read the paper and humming to himself was checking her out. She had deliberately not pulled down the skirt of her business suit and was dangling her high-heel to tease him. He was not the only patron sneaking furtive glances at her either. She had smiled to herself when a balding man in his fifties sitting with a frumpy woman who was obviously his wife had received a whack around the head when his wife had caught him looking at her legs.

But her coffee was finished and to be honest, her well-formed arse was getting sore from sitting on the stool for nearly an hour. Besides she had places to be and things to do.

She made a show of putting the dangling heel back on her foot, sliding her calf along the other leg to lift her foot to where she could adjust the shoe. This caused her legs to open slightly and her skirt to ride right up revealing a V of silky white satin panty.

'Just a tasteful glimpse,' she thought to herself and smiled when 'baldy' got another clip across the ear, and she, a baleful glare from his missus.

She alighted from the stool with dignity however, straightened the hem of skirt, (she thought about straightening the seams of her stockings but that would be too much) picked up her purse and strode confidently across the room, heels click-clacking on the polished wooden floor.

The Chelmsford Stalker had not missed the panty-peek and in fact probably would have ejaculated into his underpants if she had kept it up much longer. Not that it would have affected his libido; he seemed to be almost constantly erect and capable of sex immediately after finishing off. How many times had he fucked that last bitch? At least eight? 'They moan that they don't want to and that it hurts but they want it. All the sluts want it!' he thought.

'She wants it! She showed me her knickers on purpose! She needs a good fucking! Fucking stuck up cunt! Let's see how likes it when I put it in her!' the radio played a familiar tune.

A handsome forty-something man wearing a grey pinstriped business suit alighted from the corner table. He carried his newspaper in front him, hiding his erection, and made his way to the cashier and dropped a five pound note on the counter.

The cashier was in her early twenties and thought the man was strikingly handsome; sort like Pierce Brosnan at his prime. She smiled at him and he smiled back.

'Dozy cow! Too young! Give her another twenty years and I'll bend her over the counter and stick it in her hard!' the radio voiced.

"Thank you very much, please keep the change," his accent was refined with a deep timbre.

"Thank you sir," the cashier grinned back at him.

The Stalker exited the coffee shop and searched the street; the woman was striding purposely towards a small BMW. 'That's the sort of car that that stuck up bitches drive! Bitch cars! Cunt cars!' the radio played in his head.

He picked up the pace and caught another glimpse of her elegant, sheer-stockinged clad legs as she folded them into the small coupe. 'See! She's showing it off again! She wants it! She deserves it!'

Michele drove home carefully through the evening traffic, thinking about what she was going to wear tonight when she went out to one of the local bars. Something sexy, something exciting! She was in the mood to trap an eligible admirer and lure him home for some 'slap and tickle' as she liked to call it. She didn't notice the late model Audi following her.

Parking the car in the driveway she let herself into her modest but tidy house. She lit a cigarette and poured herself a glass of Shiraz kicking off her heels, relaxing before she would shower, redo her makeup and change before going out for the evening. She was in no rush; she had no intention of arriving at any of the tranny-friendly venues in Chelmsford until ten, maybe eleven o'clock.

The Chelmsford Stalker drove past her door as she parked.

"Stuck up cunt in a stuck up house - we'll see how stuck up she is when I stick this up her," the Stalker said to himself, his handsome face lit by the dashboard lights.

His radio did not disagree and began playing Helter Skelter as a theme in tune with his diseased thoughts.

He parked a street away under a blown out streetlight providing the gloom and darkness he needed to succeed in his evening's endeavours. He walked confidently back down the street until he was two doors away for the bitch's house. A handsome refined man dressed in a good suit did not draw undue attention; most people thought of potential rapists as being furtive young men in hoodies.

The man ducked into the shadows and furtively made his way to the woman's side gate and lifted the latch and ducked into her side yard. 'Bitches just didn't know they needed to lock up! They just thought that being attractive and sexy would protect them! Bitches didn't value security! Of course they didn't - bitches wanted to be fucked!' the radio reassured him.

Michele had replaced her heels and was leaning over sink rinsing out her wineglass when the Chelmsford Stalker snuck up behind her. He'd quietly and easily picked the lock on her back door, slid out of his expensive crocodile skin loafers and snuck up behind her.

He put his hand over mouth and pressed himself against her, putting the other hand under her chin, pressing the stiletto knife into her delicate throat.

'Interesting,' Michele thought as she felt the knife at her throat and the intruder's hard penis pressing against her buttocks.

"If you scream I'll cut you! If you struggle I'll cut you!" the Stalker hissed in her ear, grinding his crotch against her firm buttocks.

Michele looked at the reflection of the man in her kitchen window. It was the handsome man from the coffee shop. She'd figured him for a businessman stopping for coffee on the way home, who was getting a buzz out of checking out her legs and knickers before going home and screwing his vanilla suburban wife, checking Michele out to get himself aroused. 'But there you go; we live in a strange world,' she thought.

Michele froze, saying nothing.

"Good," the man said.

Michele was still dressed in the same outfit she had worn to the coffee shop but had removed her jacket.

The man removed his hand from her mouth and squeezed her breasts through the satin blouse. Michele felt his cock distend against her buttocks as he became more aroused. He slid his hand inside her blouse and massaged her breasts through her satin and lace brassiere.

"Great tits slut!" the man grunted.

Michele knew that at this stage the best thing she could do was remain silent but then he slid his hand inside her bra.

"You're going to be disappointed love," she said.

"Shut up cunt!" the man hissed.

Her tits felt full and luscious through her bra and they did at first when his hand slid inside the lacy garment but it was soon evident that something was wrong. They were false tits! Not just those stupid 'chicken fillets' that some of his bitches had used to enhance their pathetic paps, these were prosthetic tits! Fake tits!

"I told you!" Michele said.

"Shut up cunt!" the man punched Michele in the side.

'Sly cunt! Sneaky cunt! There's something wrong here! Bitch is fucking with you!' the Stalkers radio said and then began to play Girl's Talk by Dave Edmunds 'There are some things you can't cover up with lipstick and powder' the song progressed as his mind swam.

The Stalker slid his hand under her skirt and stroked her thighs. As he had presumed she was indeed wearing stockings, 'slut stockings', and he stroked her soft creamy thighs; his fingers slowly working their way up her garter straps.

Michele felt the intruder reach under her skirt and stroke her stocking tops and thighs. This was not new to her and ordinarily it was pleasant introductory foreplay before the admirer stroked her cock through her panties.

Michele hated terms like 'clitty pole, man-pussy and ass-pussy' that some transvestites used; usually in-the-closet, never-met-anyone, cock-strokers-on-a-webcam transvestites. What Michele had taped between her legs was a penis, a cock, a dick, call it what you will but not some fanciful named pseudo-clitoris. Neither was her anus a pseudo-vagina.

The caller's hand slid across Michele's satin panties and his cock throbbed at the sensation of the sleek, satiny material. There was a satisfying smooth V and he rubbed her there, mystified when he couldn't find a nice sticky slit to explore.

"You're going to be even more disappointed," Michele said sarcastically.

"Shut the fuck up BITCH!" he screamed in her ear and Michele winced as he punched her in the side again.

Michele gasped and struggled to breathe.

"I, I, I, don't have a c, c, c, cunt you dickhead; I have a penis. I'm a guy you fuckwit! I'm a tranny!" Michele wheezed, bent over.

'Slut is a man! Slut is a tranny! Fucking sneaky bitch! Fucking tranny slut!' the radio played.

'You can still fuck her! You've fucked those bitches in the arse before! She can still suck your cock! She's still pretty and she's still sexy! Fuck her! FUCK HER!' The commentator instructed and began playing Dude Look's Like A Lady by Aerosmith.

The Stalker pushed the bent over tranny onto the kitchen floor and kicked her in the ribs, winding her further.

Michele thought she felt a rib crack but that was the least of her worries; if this guy became really pissed he might kill her; she was gambling with her life. She had figured out who he was. He was the Chelmsford Stalker and who knew what he would do now that he had found out that the sexy middle-aged woman he had followed home was in fact a sexy middle-aged transvestite.

She decided she needed to keep this guy suitably occupied. She forced herself to her knees and looked up into his handsome but evil face.

"Can I suck your cock?" Michele made a sad beseeching face and fluttered her eyelashes.

The Stalker grinned and unzipped his fly.

Michele reached out and freed his long thick cock from his trousers and began to fellate him on her knees on the kitchen floor. The Stalker smiled.

She looked up and saw the insanity in his eyes, she knew she had to satisfy him so she slowly sucked on his erection. The took it all the way into her mouth and then eased it out, slurping her tongue on his glans, licking the shaft and then sucking it again.

'See, the fucking slut vixen is a natural cocksucker; you knew that when she flashed her stockings at you in the coffeshop. She might be a tranny but she's still just like the other bitches; a SLUT!' the radio played in his head.

Michele's fingers circled the base of his shaft and he tensed. He tapped her on the head with the knife.

"Don't do anything stupid bitch!" he growled.

Michele nodded obediently and lowered her face to his member holding it still as she slowly sucked it, using her tongue to encircle the glans. She felt him groan and sucked harder and faster, building the tempo.

The Stalker smiled and groaned with pleasure, watching the pretty transvestite's head bob up and down as she sucked him. He put the knife down on the counter, within easy reach, and took her head in his hands and began to fuck her face.

"Suck it baby! Suck my hard cock you slut! Take my load you tranny slut!" He howled and jackhammered his cock in and out Michele's mouth.

Michele controlled her breathing and gag reflex, she'd had plenty of practice, and sucked on the throbbing member as she lashed it with her tongue. It began to throb and she could feel the rock-hard phallus begin to palpitate.

She sucked harder and swallowed his issue as it exploded from his pulsating cock. He pulled it out of her mouth after the first few spurts and sprayed the remainder on his hot seed on her face and in her hair. He loved humiliating the bitches like this.

Michele felt him rip his cock from her mouth and knew what to expect. She shut her eyes as the scalding semen splashed over her face to ensure the semen did not get into her eyes which would have effectively blinded her for quite a while. 'Once bitten; twice shy' she thought, having experienced just such a thing in her early crossdressing days.

He slammed his cock back in her mouth and Michele dutifully drained the last of his spend.

Having finished with her for now, the Stalker shoved Michele off him and pushed her to the floor. She lay panting on the floor, her hair wild and come-sodden, wiping semen off her face with the sleeve of her blouse.

'Pathetic! What did I tell you? Pathetic? She needs a good fucking! Bitches in short skirts and stocking need to be fucked!' the radio was relentless.

"That wasn't bad but now comes the fun part, girly," the Stalker hissed.

"I thought so," Michele whimpered.

She'd read the story in the newspapers, all the gory details, the guy was insatiable by all accounts.

"What did you say cunt!" he kicked her with the toe of his boot.

Michele grunted and said nothing. She heard the ominous sound of metal clinking and sure enough when she looked up she saw he had pulled a set of handcuffs from his inside suit pocket.

He jangled them before her and Michele scrambled on the floor and tried to get up and run.

The Stalker pounced on her when she was halfway across the room. He used his weight and strength to propel her towards the kitchen table. Michele was a big woman and he was taking no chances; as she crashed into the table he pushed her shoulders down and pulled her hands up behind her back and clamped the handcuffs on her wrists. He lifted his knee and slammed it into her well proportioned behind to hold her against the table and pulled up on her cuffed wrists.

The Stalker pushed down on her shoulders so that she was bent over the kitchen table. He kicked her heels apart so that her legs were spread as far as the tight skirt would allow and he released one of his hands from her cuffed wrists and began to improve his returning erection.

Michele felt him reach under her skirt with his free hand and grasp the waistband of her panties and yank them down. She heard him panting as he stepped in close between her splayed high-heeled feet; his crotch close to her buttocks, one hand gripping her handcuffed wrists and pushing her body down hard on the kitchen table. He bought his free hand out from under her skirt and spat in the palm of it; then he spread the glistening spit over his tumescent penis, ensuring his glans was completely lubricated.

'Come on, fuck the bitch!' the radio announcer said, 'She wants it! All the bitches want it! Even bitches with cocks want it!'

The Stalker lifted the back of Michele's skirt out of the way and thrust forward. He pushed harder still and felt his glans nestled into the woman's anal bud, the sensitive glans stimulated him, bringing forth a globule of pre-seminal fluid; the clear liquid combining with his spittle further lubricated his member. He grunted and pushed forward with all his bodyweight and actually felt the heavy table move an inch or two as he thrusted.

The Stalker felt his iron hard cock tear through her tight sphincter with the assistance of the pre-seminal lubricant his shaft slid slowly and steadily inside the tranny's tight back passage until his crotch slammed hard up against her soft round buttocks. He ground his crotch in a circular motion against the her lovely soft globes and pulled her back hard against him and unloaded stream after stream of hot semen inside her tight channel.

MicheleNylons
MicheleNylons
3,912 Followers
12