The Hitman Wore Heels
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The Hitman Wore Heels free porn video
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 where warm with sandy beaches and palm trees. Until then lived the dangerous life as a CW, 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 with his hand out 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 moldy 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 disheveled 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 determining 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's 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 twenty 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 hit's them on the way out of her apartment. They like to take their goomah to dinner on Wednesday nights? The bum in the alley hit's 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 caliber 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 quality. 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 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 favorite '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 colors. 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.
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 toweled 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 colored 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 Michele Nylons.
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.
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