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K R I S T E N' S C O L L E C T I O N
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WARNING!
This text file contains sexually explicit
material. If you do not wish to read this
type of literature, or you are under age,
PLEASE DELETE THIS FILE NOW!!!!
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This work is copyrighted to the author © 2008. Please
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The Hitman Wore Heels
by Michele Nylons (michelenylons@msn.com)
***
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. (MM, v, tv, mast, oral, anal, cd)
***
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, chat rooms 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 nail
polish 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 nail polish, palettes of bright colored eye shadow
and blush and compacts and jars of finishing powder.
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 risquι 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 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.
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 eye shadow. She
dabbed on a little more eye shadow 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.
***
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 eye shadow. 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 breast-forms. 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 eye shadow
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 nail
polish; 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.
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
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story was written as an adult fantasy. The author
does not condone the described behavior in real life.
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
Kristen's collection - Directory 59