The Hitman Wore Heels

Sal pushed impatiently at her head and she took Sal's erection between her lips and sucked on it. Michele 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 Michele's head in his hands and began to face fuck her.

Michele 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 Michele'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 Michele'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 Michele.

Michele realized what he wanted.

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

Michele took hold of Sally's cock and gently pulled him behind her towards the bedroom. Sal admired Michele'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 Michele'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 Michele'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. Michele gasped and stroked Sal's leonine head as he nuzzled her crotch. Sal pulled his face out of Michele's crotch, breathing in her perfume.

"Time to take your cherry," Sal grinned.

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

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

Michele 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 Michele's skirt up and pushed it up over her back so that her pantied ass was thrust up at him. He growled and pulled Michele's ankles apart and positioned himself between her legs. Michele felt his hard cock push against her ass as he rubbed it against her satin panties. The he slid his erect penis inside Michele'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 Michele's sphincter; the thin layer of pantyhose the only protection between her anus and Sal's throbbing cock. Sally pulled the gusset of Michele's panties to one side and took hold of the diaphanous nylon pantyhose encasing Michele's ass and tore a hole in the gusset, exposing her puckered anus.

Michele 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.

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

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

"Easy please," Michele begged.

Sal's huge gut hung over Michele's ass as he forced his way further and further inside her until his crotch came to rest against her soft buttocks. Michele felt Sal's flabby thighs against hers and her nylons whispered as he ground into her. His fat gut now rested on Michele's ass as he squirmed and wriggled his cock in her rear passage. Michele 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 Michele'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 Michele 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 swiveled her hips from side to side rubbing her ass cheeks against him.

Sal pounded himself in and out of Michele, 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 Michele'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 Michele and ground himself harder against her soft buttocks.

Michele 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 Michele's panties; the garment unable to absorb the flood of semen spewing from her cock.

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

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

"You're welcome Sal," Michele 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 Michele too much to dispose of her. He would keep Michele'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 Michele he loved to be admired, caressed, fondled, used...............he shivered in anticipation as his thoughts drifted away and he dreamt of clandestine encounters with Michele 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:

'Michele, 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 everyday this week.

Yours in anticipation, xxx

Mike

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

The End