The Hitman Wore Heels

by Michele Nylons

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Ma, Coercion, CrossDressing, Fiction, Oral Sex, Anal Sex, Masturbation, Exhibitionism, Voyeurism, Leg Fetish, Violent, Transformation, .

Desc: Erotica Sex Story: The Hitman is a professional assassin and master of disguise. To carry out his next hit he has to dress as a woman to get close to his mark who has a proclivity for transvestites. Feedback and comments are always welcome.

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.

.... There is more of this story ...

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