The Hitman Wore Heels

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The Hitman Wore Heels
Michele Nylons©

The well dressed man looked with disgust and loathing at the bum rummaging in the dumpster in the dark alley. Tony 'Tough Tony' Provalono had just left Scalini's, one of the best restaurants in New Jersey, where he had tipped the waiter more money than the hobo was likely to see in his lifetime. Tony was dressed in Armani; the gorgeous woman beside him in Prada; her Jimmy Choo high heels echoed off the brick walls of the quiet streets.

"Why do we always have to leave by the back door Tony?" she whined.

"Because I said so!" Tony growled.

"Jeeze Angie; how many times have I gotta tell ya, ever since the indictments have come down; no one is one hundred percent safe," he went on, exasperated with the stupidity of his goomah.

Tony needed to worry; he had turned rat six months ago, after the FBI had shown him evidence of RICO predicates that would effectively put him in prison for twenty years. He now took very few chances with his safety, he figured that the other members of his crew would eventually figure out who was ratting them out and would one day come after him.

He was counting the days when he could disappear into the witness protection program and slip away somewhere warm, with sandy beaches and palm trees. Until then he lived the dangerous life as a CI, working with his crew and informing on them until the Feds gave him the ok to vanish into the wind.

"I don't like the way that smelly bum stares at me," Angie whined.

"Well honey; I guess he don't get to date many girls with your class," Tony quipped sarcastically.

Angie had a great ass and even better tits and she could suck a tennis ball through a garden hose but she was dumb as a stump. Tony would miss her when he eventually went on the lam; but there was plenty of great T and A out there and she would be easily replaced.

These thoughts played through his mind as he lugged Angie down the dark alley towards where he had discreetly parked his Crown Vic. He paid no attention to the bum. The bum had been in the alley for the last few weeks, and Tony saw him every time he left Scalini's. The bum turned away from the dumpster and approached Tony and his goomah begging for a handout.

The bum was dressed in reeking torn rags and his face was filthy with ingrained grime. A ripe stench of cheap liquor, rotting garbage and faeces wafted from him. His hair was matted and filthy and hung in a lank mane from under a mouldy watch-cap.

"Can you spare a dime?" the bum asked through rotten teeth; his foul breath evident even from a few feet away.

"Take a hike you facia bruta!" Tony spat at the hobo.

At the last second, when it was all too late, Tony realized he was dead. The dishevelled stinking bum looked harmless enough but his icy blue eyes gave his intentions away. As Tony pushed his goomah away and reached for his gun the bum pulled a silenced twenty two from under his coat and shot Tony twice in the head.

Before Angie could scream the bum spun on his heels and put three rounds between her eyes. He split the remaining slugs in the fifteen round magazine between Tony and Angie; emptying the pistol into their heads at point blank range. He checked Tony and Angie's pulse and, having determined that they were dead, then he pocketed his weapon. Quickly checking that the alley was still deserted he calmly walked away.

Every Wednesday for the past month, which was when Tony took his goomah to dinner eat at Scalini's, the Hitman had dressed as the bum and waited in the alley. He'd allowed his hair to grow out and kept it ungroomed. He kept the filthy rags he wore unwashed and even had a stash of filth and grime in which he covered himself before taking up his post in the alley. He didn't just impersonate a bum; he BECAME a bum.

The Hitman was a perfectionist and had successfully carried out over fifty hits for various organizations and even private citizens since he took up his profession. He didn't ask questions regarding morality or even ask why a mark had to be taken out. If a client met his price then he took the contract. Contracts were sent to him through a mailing service that could never be traced to him; he had the mail delivered to dead drops and never met his clients face to face.

If he accepted a contract he would learn everything he could about the mark. He'd follow the mark for weeks and then find an appropriate disguise that would allow get him close enough to make the hit. He'd been a doorman, a mailman, a construction worker, even a priest. There was always a way to get close to someone, no matter how tight their security might be. A mark's secrets usually led to their downfall. They go to confession? The priest hit's them in the confessional. They have a mistress? The doorman hits them on the way out of her apartment. They like to take their goomah to dinner on Wednesday nights? The bum in the alley hits them on the way to the car.

Yes the Hitman particularly liked it when his intended mark had secrets.

The next morning the Hitman was on a plane heading west; he sat in business class, the seat beside him was vacant and this allowed him to go through the dossier containing the information about his next contract that had picked up from a dead drop.

His next hit was to be a prominent member of San Francisco's underworld, Salvatore – 'Big Sally' – Catelli. The Hitman looked at the photographs and read the write up on Sally. Sally Catelli was a large man in his early fifties; he was married to a woman who looked to be as large as Sally, but he appeared to be one of the few made guys who didn't have a goomah. Sally and his wife were childless but Sally was apparently a devoted husband.

In fact, from what he read about Sally in the report in front of him, Sally didn't do anything other than work and tend to his family (both blood relatives and LCN). More importantly Sally never went anywhere without his two bodyguards. Even when Sally visited his relations he was accompanied by his two minders, who masqueraded as his driver and his personal assistant, they were at his side from the moment he left his home until he returned. If he went out for dinner, the two goons sat at the next table. The Hitman joked to himself that they probably lay side by side with him on his bed while Sal was fucking his wife.

This could be his toughest hit yet; but he bet Sally had at least one secret. Everybody did!

The Hitman leased a small apartment in Alameda and spent a month shadowing Sally Catelli. The report rang true; during the week Big Sally went to work at his tow truck company, which fronted for his mob activities, occasionally had dinner with his wife at a restaurant, and on the weekends he ate with his family at his mother's house. Most weekday nights Sally stayed at home. Through the lens of a high powered scope the Hitman watched Sally sitting at his computer in his den until the early hours of the morning.

The Hitman could try and take him out with a long shot using a rifle and scope but that would not be a certain hit and if he missed he wouldn't get another chance. Besides which he would start to lose credibility and that meant losing business. No; he would stick with his tradecraft; a close-up hit with a small calibre pistol.

Everybody had secrets, even Sally; all he had to do was find them.

Two days later Sal left home for dinner with his wife; his two bodyguards in tow. The Hitman broke into Sal's house. He rang Sal's home number and let the phone keep ringing just in case there was somebody inside that he didn't know about. He bypassed the alarm system and opened the door.

"Hallo, hallo?" he called out; his silenced pistol ready in case Sal had a guard dog in the house.

The Hitman walked over to the phone and picked up and dropped the receiver in its cradle; silencing the phone. The house was silent.

"Hallo, hallo?" he called again.

Nobody home! He searched the house room by room looking through every drawer, cupboard and closet, taking photographs with a small digital camera. 'These Mustachio Pete's sat on a pile of money but lived in pokey little houses with cheap furniture' the Hitman thought to himself, 'they probably clip coupons to use at the stores'. He went to the den and went through all of Sal's documents and mail. Nothing! He booted up the computer and took a zip drive out of his carry bag. Attached to the zip drive was a device that had been made for him by a computer whiz studying at Rutgers University. It had cost him five thousand dollars but the device bypassed passwords and all known encryption. He plugged it into the USB slot on Sal's computer and ripped every bit of data from Sal's PC onto the zip drive in a little less than three minutes.

He checked to make sure everything was as he found it and left; resetting the locks and the alarm system.

Back in his apartment the Hitman worked his way through the stolen files from Sal's computer. He had to find something soon; he'd been shadowing Sal for over a month now and his client would soon want know why he hadn't carried out the hit. There was nothing in any of the document files that helped him; they were mainly business and personal documents and of no consequence. He opened up Outlook and went through Sally's emails; the same; nothing he could use.

Then he found a hidden file that was password protected. He plugged his device into his laptop, bypassing the password and encryption. As he perused the contents of the hidden file a smile spread across the Hitman's face. He'd found Sally's secret; and it was a beauty.

The first thing he found was hundreds of images of heavily made-up, sexy dressed women, fondling, fellating and fucking men or sometimes each other. The pictures were obviously amateur and ranged from poor quality to almost professional. Pictures of the men and women having sex would not be particularly interesting to the Hitman; but there was one thing that made these pictures fascinating. The women in the pictures weren't women; they were men.

Some of them were very attractive and except for their appendages, you wouldn't know they were men. Some of them were obviously just men wearing women's clothes and makeup; their hairy heavy bodies were a dead giveaway. What really piqued the Hitman's interest was series of images where Salvatore – 'Big Sally' – Catelli was having sex with an attractive mature transvestite. So Sally did have a secret!

Next he found a found a folder that contained the details of a Hotmail and msn Messenger account. Sally's 'Window's Live' ID was 'lovesstockinggurls' and his pseudonym was 'TV Lover' and as the Hitman waded through the emails the outline of a plan began to form in his mind.

Sally had been conversing online with a number of transvestites and occasionally set up clandestine meetings with them. He didn't meet them very often; but obviously he had an obsession that had to be sated every now and then; a big risk for crime boss.

Sal's MO was to enter into an online relationship with a transvestite that took his fancy. He would exchange online correspondence and pictures. It also appeared that he would persuade the transvestite to perform on webcam for him. Once Sal was happy that he could trust the trannie to be discrete, he would set up a meeting. It was obvious from the images in the secret file what went on at these secret rendezvous. The Hitman bet his life that Salvatore – 'Big Sally' – Catelli did not take his bodyguards along to these meetings.

The Hitman now had his hook! He now knew Sally's secret and he could use it to set up the hit.

He worked late into the night thinking about how he could use Sally's penchant for transvestites to lure him to a place where he could make the hit. By the time the Hitman went to bed in the early hours of the morning he thought he had a plan that would work.

Using files and links from the stolen computer files the Hitman spent all of the next day online visiting transvestite websites, chatrooms and resource sites. He took extensive notes and joined a number of the websites to gain access to email addresses, blogs and chats.

A master of disguise, the Hitman often masqueraded in order to get close enough to a mark carry out a hit; this would be no different. What was different though was that the Hitman had never disguised himself as a woman before! Actually, he reminded himself, he was disguising himself as a transvestite.

The following day the Hitman went shopping with an extensive shopping list. Amongst the reams of data he had downloaded from the internet was a conversion table of men's clothing sizes to women's sizes. The Hitman at age forty five had kept himself fit and was reasonably slim. He took Route 4 out to Martinez to a business called Leah's Closet; a second-hand women's clothing retail store.

He figured that he was a woman's size 14 and shoe size 10; that would be a good start. He had looked at the pictures of Sal's favourite 'girls' and had a good idea of how Sal liked his girls to dress. Inside Leah's Closet he worked his way through the racks of skirts and blouses and selected a couple of skirts in navy and black and three satin blouses; in mauve, red and white. He went to the fitting room and tried them on. All of the blouses fitted him but he struggled with the buttons as they were on the opposite side to what he was used to. The cuffs were tight at his wrist but he would be able to move the buttons so that they fit ok. One of the skirts was a perfect fit but he had to exchange the black skirt for a size 16. Both skirts came to mid thigh; a navy blue pencil skirt with a kick pleat in the rear and a black A-line skirt with a split pleat in the side.

He made his way over to the shoe section and selected a pair of red pumps and a pair of black sandals; both had five inch heels. He tried on both pairs and was pleased that they both fitted him. He wandered around the store and bought some accessories to match his purchases; a nice handbag and some jewellery. He paid for his purchases with cash; the cashier didn't even raise an eyebrow at his purchases.

He got back into his car and drove back down route 4 to the K-Mart Super-centre in Concord, not far from his rented apartment. He bought a beard trimmer and good quality safety razor and ten packages of replacement razor blades and then went to the electronics section and bought a good quality webcam. He went into the lingerie department and bought two pairs of satin full-cut panties and a pair of nylon boy-leg panties. He bought two Playtex brassieres and half dozen packets of George, sheer-to-the-waist pantyhose in various colours. Most of the girls in Sal's photo collection wore stockings and suspenders but the Hitman didn't think that Sal was ever going to close enough to notice. He also bought two nylon half-slips, one black and one white.

The Hitman thought to himself that he probably didn't need to actually wear the lingerie for the purposes of the hit but he was a perfectionist and once he decided on his ruse he got totally into character; he didn't just act, he actually BECAME the character.

He went to the cosmetics department and bought a cosmetics case fully stocked with makeup, then two tubes of hair removal cream, moisturizer and nailpolish remover and a bottle of 'Poison' perfume. After paying for purchases he hit the road for his last stop and drove to business called Peggy Knight Solutions on the Bridgeway at Sausalito. He explained frankly to one of the assistants that he was a crossdresser and asked for assistance in selecting a wig. She helped him select a shoulder-length brunette bob with dark red highlights. She took him to a private room and showed him how to fit the wig and advised him how to care for it. He paid for the wig in cash and drove back to his apartment.

The Hitman opened up his packages and put away his purchases and started preparing himself to learn how to become a transvestite. He had reams of printouts that he had downloaded from various websites that provided advice for beginner transvestites. He read through them again and then got to work.

He used the beard trimmer to shave his legs, chest, belly and arms down to fine stubble. He trimmed away most of his pubic hair and was able to get to the small of his back and remove the small patch of back hair there. The Hitman was lucky that he wasn't particularly hirsute. He then painstakingly shaved his feet, legs, chest and belly with the safety razor. This took quite some time and he had to change the blades quite regularly. He shaved the fine hairs off the back of his fingers and hands, shaving up past his wrists all the way up his arms.

Then he opened the hair removal cream and after reading the instructions he applied a thick coat of the smelly cream over the hairs in his crotch and buttocks making sure that he got into all of the crevasses. The cream smelt quite vile and he was glad when he finally got into the shower and rinsed it all off. He watched with amusement as small clumps of his body hair disappeared down the drain. He was amazed at how smooth his body felt as he washed himself under the shower. It felt quite sensual having no body and leg hair and he thought seriously of keeping his body hairless permanently from now on.

He shaved his face carefully and towelled it off. Now would come the difficult part; learning how to apply makeup. He sat down at the dresser where he had arranged the contents of the cosmetics case. He had never noticed before how fascinating and attractive cosmetics containers would be. Long tubes of mascara, eyeliner and lipstick, bottles and pots of foundation and nailpolish, palettes of bright coloured eyeshadow and blush and compacts and jars of finishing powder.

He looked at a printout that he had downloaded from a TG resource site that was titled 'Makeup for First-Timers and Closet Crossdressers.' He read it over and over quite carefully and then made his first attempt applying makeup. The foundation, finishing powder, blush and lipstick were not too hard to get right but the eye makeup was a pisser. It took hours before he mastered the skill of getting his eyeliner right and then about the same amount of time experimenting with different shades of eyeshadow. Appling mascara was not quite as difficult, but it still took time to master.

The Hitman had to clean off the makeup a number of times during his apprenticeship in makeup 101. He went to bed in the early hours, with his face stinging slightly from the constant cleansing, but happy that he could use the cosmetics effectively. Tomorrow he would dress as a woman for the first time.

The Hitman arose late the next day and showered and shaved his face closely. He reread one of TG resource tips about how to make home-made breastforms. He opened a package of pantyhose and cut the legs from the gusset of the hosiery. He filled the feet of the pantyhose with rice until he had the desired size and then doubled the legs over and tied them off, cutting the nylon at the knot. He smiled to himself; he'd just made his first pair of false tits.

He sat at the dresser and applied foundation and finishing powder. He worked on the eyeliner next, concentrating on getting it just right from the inner corner of his eyes to the outer corners, gradually thickening the line. He went to work on the eyeshadow using a combination of light blue and pink that had worked well when he was practicing last night. He rouged his cheeks and applied a coat of 'skin glow' finishing powder. He painstakingly mascaraed his eyelashes and reached for the two coat lipstick.

He painted his toe and fingernails with plum red nailpolish; painting his toenails and the fingernails of his left hand was relatively easy, but it was awkward using his left hand to paint the nails on the fingers of right hand. When he was happy with that he had his makeup right he reached for the wig. The shoulder-length brunette bob with dark red highlights sat perfectly on his head, the fringe level with his eyebrows.

He was amazed at the transformation; he looked quite attractive. He looked similar to many of the transvestites in Sal's illicit picture collection. It was important that he be attractive to Sal but he admitted to himself that he liked the feminine way he looked and that the taste and smell of the makeup was quite appealing.

The Hitman took his homemade breast forms and fitted them inside the cups of a bright red brassiere. It took him a little while fiddling with the straps to get the bra to sit right on his chest. Then he opened a packet of the George sheer to the waist pantyhose and reviewed the printed instructions describing how to put the pantyhose on.

The Hitman was taken aback at the sheer sensuality of the feel of the silken nylons on his shaved legs. He liked to stroke the stockinged legs of the women that he fucked, but actually wearing the luxurious hosiery was far more exciting. He carefully arranged the toes of the pantyhose around his painted toes and admired the sheen of the nylon on his legs and the silhouettes of his painted toenails through the reinforced stocking toe.

The translucent pantyhose gusset caressed his buttocks and genitals with stark sensuality, and caused him, dare he think it, to become aroused sexually. He smoothed the Nylons up his legs and then stepped into a pair of red full cut satin panties. The panties hissed as they slid up his nylon sheathed thighs and as he adjusted them to sit snugly on his buttocks, he was entranced at the sumptuous feel of the satin and nylon on his body. He tucked his penis under his crotch where it was held in place by the pantyhose gusset and the tight satin panties. He was further enraptured with the sumptuous feel of the satin half-slip against his legs and ass when he stepped into it and adjusted the hem high up his thighs.

Next he stepped into the blue pencil skirt and then he buttoned himself into the mauve, long-sleeved, satin blouse and tucked it into the waistband of the skirt and closed the zipper. He adjusted the waistband of the skirt, and adjusted the hem so it covered the hem of the slip. The skirt was tight around his buttocks and thighs; the hem sat high on his thighs.

He looked at himself in the mirror and saw exactly what he had hoped for; a mature, slutty looking, transvestite. He stepped into the red pumps, and struggled initially with the difficulty of walking in the high heels. He sat at the dresser and accessorized himself with the jewellery. Although it was not essential to the task at hand, he sprayed himself liberally with perfume and then stood in front of the mirror.

He was now fully in character. He was quite happy this was the character that he had chosen to lure Sal to his fate; it was going to be a lot more appealing than the month he had spent dressed in the reeking rags of the bum.

The Hitman thought that he looked like the type of transvestite that would be attractive to Sal. The heavy makeup, the subtly-streaked shoulder-length hair, the tight skirt, long sexy legs and high heels were the trademark looks of the transvestites in Sal's picture collection.

The Hitman stripped out of the female attire and removed his makeup and went through the same procedure three more times, getting better at it each time he dressed. He enjoyed the feel of the lingerie on his body and found his female persona quite attractive but he remained focused and professional. He was dressing like this because he had an important job to do; it was just an ends to a means; although he was honest enough to admit to himself that dressing this way was quite thrilling.

After he dressed for the forth time he set up his digital camera and using the timer he took a series of photographs of himself in provocative poses; each picture progressively raunchy. He downloaded them onto his laptop and Photoshopped until he had a series of images suitable for posting online and resized one of them so that it could be used for his online profile picture.

During his research online he discovered that transvestites liked to give themselves risqué feminine non de plumes. Some where downright silly such as 'Sally Sucks' and 'Wendy Wantsit'; he wanted something that would be tantalizing but not overtly sexual. He played with a few different variations and settled on Linda Sleek.

It took him about three hours online to set up a hotmail account and join a number of transvestite resource and meeting sites; he also joined a number of personal and 'friend finder' sites. He posted his picture and wrote in his profiles that he was relatively new to crossdressing but was extremely discrete and trustworthy and keen to meet an admirer for very discrete meetings.

Using his Windows Messenger tools menu he added 'lovesstockinggurls', Sal's hotmail handle, to his online contacts and then sent him an email. It read:

'Dear TV Lover, I saw your profile at TVChix and thought that we may share a common interest. I am a mature TV who lives in the Bay area who is interested in having a very discrete meeting with someone who I can trust. I have taken the liberty of adding you to my Messenger contacts and will be online after 9:00pm each evening this week

xxx Linda'

Sal took the bait that evening. After retiring to the privacy of his den, his wife in bed snoring over the drone of TV soaps, he fired up his PC and logged into his encrypted files. As soon as he went online he got a pop up on Messenger asking if he wanted to add Linda Sleek to his contact list. This was intriguing as he seldom gave out his email address. He didn't click yes or no just yet; instead he opened his Hotmail account. Sure enough there was an email from Linda Sleek.

He read the email and his interest piqued; he looked up Linda Sleek Windows Live ID profile. He was impressed by what he saw. Her profile picture was quite provocative; mature, attractive, heavily made up, holding up the hem of her pencil skirt displaying silky nyloned thighs. Yummy!

He went back to the Messenger window and clicked yes. When he opened his Messenger window she was listed in his contact list as online. He double-clicked on her name and entered into a Messenger conversation. Sal was careful not to reveal too much about himself and was very direct in his questioning of where she had got his Live Messenger ID.

Linda played it equally coy and managed to convince Sal that she was legit and not some online loony or scam-artist. They chatted about common interests regarding the secretive world of closet transvestites and admirers. Linda soon picked up on the vernacular peculiar to the world of crossdressers and was able to convince Sal that she was who she presented herself as. Sal asked if she would set up her webcam for their next online meeting and Linda agreed. They set up a Messenger meeting for the next evening; at 11:00pm. Sal had taken the bait!

The next evening the Hitman dressed as Linda and set up his webcam so that it showed a video stream of her sitting at the laptop but did not show too much background detail. At 11:00pm Linda logged into Live Messenger and was immediately rewarded with a Messenger window from Sal.

Sal wasted no time and an IM popped up on Linda's computer screen.

TV Lover: 'let me c’ Linda: 'ok'

Linda activated her webcam and Sally accepted the video stream. Linda was sitting at her PC dressed in her pencil skirt, mauve satin blouse, sheer hose, high heels and heavy makeup. She waved at the camera and blew Sal a kiss.

TV Lover: 'lovely, wanna c more'

Linda turned so that she was facing directly at the camera and hiked up her skirt to the top of her thighs.

TV Lover: ' stockings?' Linda: 'u don't like my pantyhose?' TV Lover: 'sure but prefer stockings' Linda: 'what about if i do this?'

Linda stood up and let the hem of her skirt drop back down her thighs; then she turned her back to the camera and slowly hiked the back of her skirt up until her red satin panties were exposed. She wiggled her buttocks.

TV Lover: 'nice me the front'

Linda complied and spun on her heels and slowly raised her skirt until the front panel of her panties was exposed. She pouted and made air-kisses at the camera.

Despite the fact that Linda was doing Sal's bidding only so that she could entice him into a lethal trap she still found herself getting aroused. She felt feminine and sexy, but most of all she felt empowered; Sal was giving the orders but she was in control. She allowed the hem of her slip to fall back down her thighs and then began to stroke the satin material up and down her legs and over the front of her panties.

In his darkened den; with the door locked and his wife fast asleep, Sal unzipped his flies and freed his thickening erection; his eyes glistening in the glow of his computer screen.

TV Lover: 'sit'

Linda complied and sat back down, adjusting the hem of her skirt.

TV Lover: 'open legs'

Linda opened her legs and let Sal look up her skirt to see her panties. A few minutes later:

TV Lover: 'take off skirt'

Linda stood and unbuttoned the waistband of her skirt, unzipped it and let it fall to her feet. She kicked it away.

TV Lover: 'lose the slip'

Linda slid her slip slowly and sensuously down her legs until it pooled around her high heels. She stepped out of it and sat back down.

Sal was salivating with lust in his study; slowly stroking his erect penis.

TV Lover: 'open legs'

Linda opened her legs again and made a show of fluttering her fingers up and down her nylon encased thighs; occasionally letting her fingers stroke the front of her panties.

Sal orgasmed; shooting his spend into a silk handkerchief. He groaned and sweated and lusted after the sexy transvestite performing before him on his computer screen.

TV Lover: 'just came' Linda: 'hope u like what u saw?' TV Lover: 'very much.....same time 2morrow?' Linda: 'u bet.....maybe i get 2 c u?' TV Lover: 'maybe'

Linda's Messenger window indicated that Sal had signed out. She looked down and saw that her penis was stiff, the gusset of her hose was stretched tight around her erection and a small patch of pre-seminal fluid stained the front of her panties. She didn't realize how aroused she had become during the webcam show. She freed her erection and masturbated, soaking up the semen with her slip. She didn't need this distraction. She couldn't control her own body's pleasure centres but she could remain focused on the job.

The Hitman undressed and dropped the pantyhose, panties and slip into the washing machine and put it on the delicate cycle. He wondered how long he would have to play these online games with Sal before he could entice him into a meeting. He would have to be careful not to appear too eager.

Linda and Sal met online every night for the next week except for the night that Sally took his wife to dinner. Linda was becoming more absorbed in her role as a transvestite whore. She found herself increasingly enjoying the role-play and had to remind herself that it was only a means to an end. Sal's requests got bolder and bolder. The last time that Linda was on her webcam Sal asked her to masturbate for him and she came over her thighs. Then he asked:

TV Lover: '2morrow can u use a dildo?' Linda: 'maybe? but if i do i want 2 c u 2' TV Lover: 'ok'

TV Lover signed off and as the Hitman took off his semen soaked hosiery he wondered how long he was going to have to play online with Sal before he could set up the hit. Time was running out.

The next evening Linda sat in front of the webcam her skirt and slip around her ankles, her lipsticked lips sucking on an eight inch fake rubber cock. The Messenger window flashed:

TV Lover: 'i wanna 2 c u put it in u' Linda: 'not unless i c u 2' TV Lover: 'tease' Linda: 'yep'

Linda ran her tongue along the pink rubber cock and then slowly encircled it with her plum red lipsticked lips.

Linda: 'wish this was u' TV Lover: 'you r hot.......sending webcam vid now'

Sal had double locked the door to his den and firmly closed the curtains before going online. He dropped his pants and improved his erection. He clicked on the send button and his own webcam video began to stream across the internet into Linda's computer.

Linda: 'nice cock' TV Lover: 'ty, now put it in please' Linda: 'not until i c ur face......wanna watch u while I fuck myself'

Sal debated with himself for only a few seconds; he was infatuated with Linda and wanted her so much. He panned back with his webcam until his whole body came into view. Linda looked at her monitor and smiled; there he was; TV Lover was definitely Sal Catelli. She would have to play along now to spring the trap.

Linda: 'imagine this is u'

Linda took the dildo from her lips and reached for the tube of K-Y jelly next to the computer keyboard and liberally coated the rubber cock with the clear viscous lubricant. She stood up and kicked away her skirt and slip and knelt on the chair with her back to the webcam. She eased down her panties and pantyhose, bunching them around the top of her thighs. She looked at the screen and saw that Sal was sweating and stroking himself.

TV Lover: 'put it in u slut' Linda: 'ok'

Linda put the tip of the dildo against her tight anal bud and slowly pushed it inside her. She had never done this before and was quite surprised that the well greased dildo didn't cause as much discomfort as she thought it would. As she slid it further inside herself she forced her sphincter to relax. When it was fully imbedded inside her anus she stopped and rested, allowing her back passage to accommodate the rubber cock.

TV Lover: 'fuck yourself' Linda: 'ok honey....wish this was your cock'

Linda slowly eased the dildo in and out of her anus and was quite astounded at how pleasurable it felt. The dildo stimulated the sensitive nerves around her sphincter but the most intense sensations came when the cock rubbed against her prostate. She had heard about this form of stimulation before but she never dreamed it would be so gratifying.

She rammed the rubber phallus in and out, faster and faster, whilst watching the computer screen. Sal was wanking his engorged prick ferociously, his fat face puffed up and red with exertion. Linda felt a delightful sensation pulse through her anus and realized that she was about to orgasm. She couldn't believe that she could climax without touching her penis; but her cock hardened only slightly before spewing forth stream after stream of hot semen. On the screen Sal was shooting his load all over his fat belly.

Linda gasped and leaned over the back of the chair ramming the dildo deep inside her back passage as her orgasm shook her. Sal's eyes were locked on the screen watching her intently as his own orgasm racked his body. He had to have her! He really wanted to get his hands on this hot bitch. They both panted as they came down from their respective climaxes. Linda pulled up her pantyhose and panties and sat back at the keyboard.

Linda: 'u like?' TV Lover: 'u bet!....u?' Linda: 'mmmm wish it was a real cock tho' TV Lover: 'maybe i can arrange that' Linda: '???????????' TV Lover: 'wanna meet IRL' Linda: 'would luv 2......where? have 2 b discrete' TV Lover: 'can we use your place?'

Linda smiled at Sally and nodded at the webcam; the trap was sprung.

Linda: 'ok honey......but must b very discrete' Linda: 'call 555 2865 after 8pm 2morrow ok?' TV Lover: 'ok where r u?' Linda: 'Alameda' TV Lover: 'not 2 far then' Linda: '2morrow then......look forward to it' TV Lover: 'can't wait'

Linda closed the Messenger window and turned off the webcam. The Hitman had planned on taking out Sal as soon as he entered his apartment but after that little performance he decided that he might let Sal at least go away with a smile on his face; no reason he couldn't mix a little pleasure with business.

At precisely 8:05pm the next evening the Hitman's cell phone rang.

"Linda," she said into the phone.

"Hello; where are you?" Sally's gruff voice barked out of the earpiece.

This was the dangerous part; the Hitman was ninety nine percent sure that Sal would lose his bodyguards for his secret assignation with the transvestite but there was always that one percent. Linda gave Sal her address and apartment number and told him to ring her cell when he arrived and she would buzz him in.

Linda went to the mirror and checked herself out and made some final touches to her makeup. She wore the white satin blouse; a gold necklace glimmered at her throat; matching clip-on earrings glistened through the hair of her shoulder-length brunette bob. Linda had selected her black A-line skirt with the side pleat which exposed a lot of leg; the hem came to mid-thigh and she decided that a half slip would spoil the effect of the split skirt so she didn't wear one. Sheer taupe nylons shimmered on her legs; black patent leather high-heel sandals completed the outfit, a glimmer of red toenail polish visible through the reinforced toes of her nylons.

She looked at her heavily mascaraed eyes framed by the black eyeliner and pink and green eyeshadow. She dabbed on a little more eyeshadow and dabbed a little more blush on her cheeks and then gave her face a quick all over dusting with her 'skin glow' finishing powder. She put on another coat of the plum red lipstick and smacked her lips. She gave herself a liberal spray of Poison perfume, finishing with a quick spray under her skirt.

Her cell phone buzzed and she went to the wall mounted call box and buzzed open the building's entrance door. She opened the front door to her apartment and left it ajar and then stood in the centre of the room striking a sexy pose. She was trembling with anticipation and excitement.

Sally burst through the front door, panting and wheezing at the exertion of climbing the three flights of stairs. He slammed the door shut and threw his topcoat on the sofa.

"Fuck doll; you great," Sal growled as he looked Linda up and down.

Sally Catelli was an alpha male and never let manners or etiquette get in the way of taking what he wanted; and he wanted Linda right now. He unbuttoned his coat and tore off his shirt and trousers. He stood there in his boxers and sox, his fat gut hanging over a growing erection.

He stepped forward and pulled Linda roughly into his arms. His mouth fell on hers with ravenous hunger; his tongue thrusting into her mouth. Linda could taste the pasta that Sal had eaten at dinner but she still became aroused knowing that she was turning Sal on. She was crushed against his fat body and she could feel his cock pushing against her belly. She knew what he wanted and she encircled his thick cock in her fingers and slowly squeezed.

Sal shuddered and kissed her passionately and groaning with lust he slid his hand under her skirt and pawed at her nyloned thighs. He squeezed her buttocks through her panties and pushed himself harder against her. Linda began to stroke his ever hardening cock as Sal squished her ass and stroked her thighs. He pushed her away, gasping for breath.

"Gotta stop or I'm gonna come," he panted.

"Get your ass over here," he ordered and he sat down on the couch.

Linda walked seductively over to the couch and stood before him. He reached out and lifted the hem of her skirt and stroked the front of her satin panties.

"You're wet you slut," Sal mumbled.

He put his hands on her hips and pushed down. Linda bent her knees and then realized what he wanted and dropped to her knees in front of him. Sal pulled her toward him and kissed her, driving his tongue deep into her mouth, tasting her lipstick and enraptured by her perfume.

Linda felt Sal place his hands on her head and push down again. She complied and lowered her face to his groin. His crotch smelt musty with arousal; she looked at his thick penis and then tentatively licked at it. A clear globule of pre seminal fluid glistened on the tip and she licked it off. It was almost tasteless but her first taste of cock was very stimulating.

Sal pushed impatiently at her head and she took Sal's erection between her lips and sucked on it. Linda opened her mouth and swallowed the fat throbbing cock and bobbed up and down, licking and slavering at the purple glans and thick trunk. Sal was moaning with ecstasy as he held Linda's head in his hands and began to face fuck her.

Linda struggled for breath as Sal thrust his cock in and out of her mouth but she soon developed a rhythm and was able to time her breathing between his thrusts. Sal was grunting like a pig in a trough as he fucked Linda's face; he loved the view he was getting of her kneeling before him on the floor with her head bobbing up and down in his lap and her ass pushed high in the air.

He felt his orgasm approaching but he didn't want to come yet so he pulled Linda's face from his groin.

"You give good head girl; you take a guy's cop like a pro," Sally chuckled.

"But now let's see how you fuck!" he stood up and looked questioningly at Linda.

Linda realized what he wanted.

"In the bedroom; let's fuck on the bed," she smiled.

Linda took hold of Sally's cock and gently pulled him behind her towards the bedroom. Sal admired Linda's ass and long nylon encased legs; he couldn't wait to fuck this bitch. She sat Sally down on her bed and stood in front of him and bent down and kissed him passionately and then drew her face away from his and looked down at him.

"So you like what you see?" she giggled; amazed at the control she had over this powerful man.

"Lift your skirt up!" he asked.

"You do it," she whispered.

Sal took Linda's skirt in his hands and slowly raised it up her thighs. His stroked her legs and then leaned forward and licked her gossamer nylons. His rough face rasped against Linda's pantyhose and satin panties as he snuffled at her thighs and crotch, then his mouth encircled her hardening cock through the layers of satin and nylon. Linda gasped and stroked Sal's leonine head as he nuzzled her crotch. Sal pulled his face out of Linda's crotch, breathing in her perfume.

"Time to take your cherry," Sal grinned.

"Be gentle hun," Linda winked down at Sal.

"Yeah right," Sal laughed, "now get yer ass on the bed!"

Linda climbed up on the bed and knelt down with her head near the pillows; she felt the bed shift as Sal moved behind her. Sal rucked Linda's skirt up and pushed it up over her back so that her pantied ass was thrust up at him. He growled and pulled Linda's ankles apart and positioned himself between her legs. Linda felt his hard cock push against her ass as he rubbed it against her satin panties. The he slid his erect penis inside Linda's panties and placed in between her buttocks.

Sal thrust his hard cock against the gossamer pantyhose and pushed the silky material into the crevice of Linda's sphincter; the thin layer of pantyhose the only protection between her anus and Sal's throbbing cock. Sally pulled the gusset of Linda's panties to one side and took hold of the diaphanous nylon pantyhose encasing Linda's ass and tore a hole in the gusset, exposing her puckered anus.

Linda felt a pang of trepidation as she reached out to the nightstand and took hold of the tube of K-Y jelly.

"Ok, let's get me lubed," Sal wheezed, impatient to fuck the soft white ass offered up before him.

Linda squeezed a big dollop of the cool slippery liquid into her hand and reached awkwardly behind herself and liberally coated Sal's cock with the lubricant. Sal took the tube out of her hand and squeezed another generous blob onto Linda's anal bud.

Sal tightly gripped Linda by the hips and pressed his lubricated glans against Linda's sphincter. He thrust forward slowly and his greased cock slowly slid into Linda's tight ass. Linda felt a dull pain as Sal's cock invaded her virgin ass.

"Easy please," Linda begged.

Sal's huge gut hung over Linda's ass as he forced his way further and further inside her until his crotch came to rest against her soft buttocks. Linda felt Sal's flabby thighs against hers and her nylons whispered as he ground into her. His fat gut now rested on Linda's ass as he squirmed and wriggled his cock in her rear passage. Linda relaxed her sphincter to accommodate the invading member. She was starting to experience the same pleasure that she had got from fucking herself with the dildo and she pushed back against Sal.

Sal took hold of Linda's silken thighs and thrust slowly in and out of her, his hands stroking her legs and ass. One of his hands snaked around to the front of her panties as he slowly fucked her. Sal began to fuck her harder and faster, and Linda pushed back against him and fell into the rhythm.

She felt the spongy hard mass of Sal's glans push against her prostate; and ripples of sexual pleasure flowed up and down her anus. She pushed back against Sal with her buttocks and swivelled her hips from side to side rubbing her ass cheeks against him.

Sal pounded himself in and out of Linda, fucking her harder and harder, grunting and panting. He gripped her hips and pulled her back, hard against him, as he thrust forward pushing his cock into her and grinding his balls against Linda's nylon encased buttocks. His cock began to convulse deep inside her, pulsing and spiting as it spewed out streams of hot semen. Sal shot torrents of come deep inside Linda and ground himself harder against her soft buttocks.

Linda pushed back hard forcing her ass back against him and wriggled her hips as her own orgasm ripped through her. She flooded her panties and hose and moaned in ecstasy; her cock spasming as her climax shook her. She wriggled her hips again and reached around and grabbed Sal's thighs and pulled him hard up against her, forcing the last of his seed to wash over her prostate. A puddle of come oozed from the front of Linda's panties; the garment unable to absorb the flood of semen spewing from her cock.

Eventually both Sal and Linda were sated and Sal pulled his cock out of Linda's ass with an audible plop. Viscous white semen leaked from her puckered anus and soaked into her torn nylons.

"Thanks for the fuck Linda," Sal chuckled, and smacked her playfully on the ass.

"You're welcome Sal," Linda replied and reached under the pillow and pulled out a silenced twenty two pistol.

She rolled over and shot Sally twice in the right eye.

The Hitman relaxed in his business class seat on the fight back to Newark Liberty and ordered a drink from the airline hostess admiring her long legs encased in sheer hose. He smiled to himself as he thought about his own hosiery, lingerie, cosmetics, wig and other female attire packed away in his checked luggage. He decided that he liked being Linda too much to dispose of her. He would keep Linda's identity and set up discrete meetings with other transvestites and admirers and have hot sexy fun.

The fascination, power and out-and-out sexiness of crossdressing was quite addictive; he was no fanook but when he was dressed as Linda he loved to be admired, caressed, fondled, used...............he shivered in anticipation as his thoughts drifted away and he dreamt of clandestine encounters with Linda being kissed and caressed by anonymous handsome admirers.

Three months after Salvatore – 'Big Sally' – Catelli was given his Moe Green Special, the west coast crime bosses awarded a contract to the Specialist to find the man who had taken out Sally Catelli. They didn't much care that Sally had been put to rest; but it was a matter of pride that they send a message to their compatriots on the east coast that they would take care of their own dirty laundry.

It took the Specialist only a few days to find the secret files in Sal's computer and then to get them decrypted. Once he had access to the files he was very surprised at their content but impressed with the ingenuity that the Hitman had used to lure Sal to his death. But the Specialist was also no amateur when it came to disguises and role play.

A week later the Specialist looked at the screen of his PC and read the email that he'd drafted. It read:

'Linda, After reading your Messenger profile and seeing your picture I find myself immensely attracted to you. I am a forty something admirer who is very interested in getting to know you better. Perhaps, once we get acquainted online we might even consider a discrete rendezvous?

I'll be online at 9:00pm every day this week.

Yours in anticipation, xxx


The Specialist clicked the 'send' button and smiled to himself.

The End

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joannebarbarella's picture

Will the Hitman take the bait? Is Linda now in control? Fascinating conjecture.

Nice twist

I guess we can' t feel sorry for the Hitman if he got what was coming to him.

My money's on the Hitman

Who's more clever? The Hitman, or the Specialist?

Great ending

Will the Hitman be smart enough to see through the Specialist, or will his lust for sex blunt his sense of caution? Great that you leave us to work out the possible ending for ourselves