The Hitman Wore Heels

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.

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 Michele'

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 Michele Nylons 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 Michele Nylons.

He read the email and his interest piqued; he looked up Michele Nylons' 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.

Michele 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. Michele 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 Michele 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 Michele 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 Michele logged into Live Messenger and was immediately rewarded with a Messenger window from Sal.

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

TV Lover: 'let me c' Michele: 'ok'

Michele activated her webcam and Sally accepted the video stream. Michele 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'

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

TV Lover: 'nice.....no stockings?' Michele: 'u don't like my pantyhose?' TV Lover: 'sure but prefer stockings' Michele: 'what about if i do this?'

Michele 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 ass......show me the front'

Michele 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 Michele 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'

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

TV Lover: 'open legs'

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

TV Lover: 'take off skirt'

Michele 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'

Michele 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'

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

Michele'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 centers but she could remained 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.

Michele and Sal met online every night for the next week except for the night that Sally took his wife to dinner. Michele 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 Michele 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?' Michele: '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 Michele 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' Michele: 'not unless i c u 2' TV Lover: 'tease' Michele: 'yep'

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

Michele: '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 Michele's computer.

Michele: 'nice cock' TV Lover: 'ty, now put it in please' Michele: '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 Michele and wanted her so much. He panned back with his webcam until his whole body came into view. Michele 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.

Michele: 'imagine this is u'

Michele 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' Michele: 'ok'

Michele 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' Michele: 'ok honey....wish this was your cock'

Michele 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. Michele 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.

Michele 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. Michele pulled up her pantyhose and panties and sat back at the keyboard.

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

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

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

Michele 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.

"Michele," 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. Michele gave Sal her address and apartment number and told him to ring her cell when he arrived and she would buzz him in.

Michele 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. Michele 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 center 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 Michele 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 Michele 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 Michele roughly into his arms. His mouth fell on hers with ravenous hunger; his tongue thrusting into her mouth. Michele 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. Michele 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.

Michele 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. Michele 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.

Michele 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.