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THE SILK SCARF
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Judge not a book by its cover.
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Ann Douglas
Ann Douglas
226 Stories2535 Followers

Michael sat at the table playing with his drink. He'd gotten his first
real paycheck today and decided he deserved a dinner in the best
restaurant he could afford. Of course with what they were paying entry
level trainees at Donaldson & Rhobes, his choices quickly narrowed to a
few. So he found himself on 11th Avenue instead of Broadway, but still
he felt like he was on top of the world. Not bad for a kid from the
sticks now living on his own in New York City.

The 21 year old was looking as to where his waiter had vanished to when
he first noticed her, sitting at a table over in the corner. Two things immediately caught his attention. First were her eyes, vivid blue pools
that seemed to sparkle even at a distance. Second were a pair of
spectacular legs, which although partially obscured by the table, seemed
to go on forever. As best he could, he followed the line of her legs
right down to the stiletto heels at the end of them.

The young man knew he was staring but couldn't bring himself to turn
away, even when he realized that he was also now sporting a first class
hard on. She was older than him, late twenties or early thirties he
would guess. Her dark hair was done up and she was wrapped in a sexy red
dress which showcased those fantastic legs at one end and full rounded
breasts on the other. All in all, Michael noted to himself, she was one
very hot woman.

At first he thought it was his imagination, but then he was certain of
it. She was looking right back at him, dangling one of those killer high
heels off her foot. Michael couldn't tear his eyes away and she knew it.
A little smirk appeared at the corner of her soft lips as if she could
read his mind and knew exactly how hard she was making his dick.

Then, unbelievably, she crooked her finger, motioning for Michael to
come over to her table. Long seconds passed as he sat petrified, then
like a zombie, he grabbed his drink and lurched across the room to her
corner.

"You look like you could use some company." she said with that same
smirk playing across her lips as she motioned for him to sit next to her
at the small table.

"I certainly could." Michael replied, feeling for the first time since
he had arrived in the city like a small town rube.

"My names Catherine." she said as she ran her gaze up and down his body.
"And it seems to me that you're getting extremely excited just by
looking at my body, hmmm?"

Michael flushed a deep red, unsure what to say. His mind was a blank as
he searched for the right phrase.

"You're legs are magnificent." he blurted out, feeling incredible stupid
the moment he'd said it.

"Oh, is it my legs that made your dick so hard? She said, gazing down at
the large lump in his pants.

Michael was now totally speechless. He'd never felt so embarrassed in
his life. He wished he could just run for the door and disappear.

"Don't worry honey, I consider that the finest compliment." she
whispered as she leaned over close enough for him to smell the scent of
her perfume.

Relieved, Michael started breathing again.

"In fact, I have a certain weakness for young men like yourself." she
went on. "In fact, I have this knack of knowing just what a young man
like yourself needs. What you fantasize about and what you really crave.
Just think how excited you're going to be when I take you home with me
and make all of those dirty dreams of yours come true."

"W-h-at do you mean?" Michael stuttered.

"What I'm offering you is a chance to live out your most secret
fantasies. A chance to let your secret self out for a night."

Michael was becoming lost in the mixture of those captivating eyes and
the music of her voice.

"What's your name?" Catherine demanded.

"Michael." he answered.

"Well, Michael, shall I tell you what it is that you want me to do to
you, my little boy." she asked, again with the little laugh.

"Yes, please."

Catherine leaned forward and looked deep into his eyes, drawing him
deeper into her spell. Then, quietly, graphically, she proceeded to
detail his most secret and powerful fantasy.

"My guess is you'd like me to take control, to take you home with me,
tie you up so you couldn't move a muscle, and then tease you for hours
until you spurt globs of cum. Make you do all those nasty little things
you would never have the courage to do on your own.

If he had been red-faced before, his hue now paled as Catherine
whispered in his ear. She had repeated things he had never spoken out
loud to anyone in his life. Desires so secret he was sometimes even
afraid to fantasize about them.

"There's no need to be embarrassed." Catherine whispered into his idea.
"No one else can hear us."

Michael felt like she had read his mind, his dick had gown so hard he
thought it would burst from his pants. It felt like all the blood in his
body was rushing from his head to his groin. Catherine didn't help
matters any by slowly rubbing her leg up against his thigh under the table.

Color slowly returned to Michael's face as he composed himself. He still
felt more than a little lightheaded with the revelation of his darkest
desires. It was as if he was wearing a sign on his forehead that
screamed pervert.

"So what do you think my little man?" the older woman asked. "And I do
hope I'm only using that phrase figuratively. Do you have the courage to
live those desires?"

Michael's heart was beating rapidly, his palms were sweaty. Part of him
feared answering yes but another part feared ever more never having this
chance again. The word seemed stuck in his dry throat.

"Y..Ye..ss." he finally managed to utter.

"Excellent." Catherine smiled broadly, overwhelming him with a wave of
desire. "Let's get out of here then. I'm suddenly ravenous, but what I
crave isn't on the menu."

Without waiting for his reply she rose and started for the door. As she
rose Michael noticed how tall she was, almost 2 inches over his 5 '8".
Dropping some money on the table to cover the bill, he followed her out
into the street.

"My car is in the lot next door." Catherine said as she turned to the left.

Michael quickly followed, admiring the sway of her tight little ass as
she walked. It was almost a crime, he thought, for any woman to have
such a perfect ass. "One minute please." the garage attendant said as he
took the parking ticket from Catherine and called on the intercom for
one of his drivers to bring down her car.

Less than a minute later, an ebony black Porche two seater zipped down
the long circular ramp and came to a stop in front of them. Mentally,
Michael calculated the cost of the car as being more than he could save
over the next ten years. He also noticed as Catherine slipped the driver
a twenty dollar bill. It was obvious that money really wasn't a concern
for her. It took a few moments for Michael to realize that Catherine was waiting for him to open the door for her. He quickly rushed over and
opened the driver's side.

As Catherine settled into the plush leather seat, Michael got a
beautiful view of her rounded breasts as they strained against the top
of her dress.

Closing the door, he ran to the other side and climbed in next to her.
Without a word, Catherine started the ignition and the car roared out
into the night.

They'd traveled about five blocks when Catherine pulled the car over to
the curb. She put the car in neutral and turned to her passenger.
Michael in the meantime was looking up and around him. All of the
buildings on this block were stores and offices. All were dark and
closed at this time of night.

"Take off your tie and jacket." Catherine instructed him.

"Okay." Michael said as he pulled at the knot of his red tie and stuffed
it into his jacket pocket. Then he draped his jacket over his bucket
seat. The white shirt he wore underneath was short sleeved.

"Nice." she said as she ran her fingers up his lightly tanned arm.

Michael could feel the movement of every hair in his arm as her
fingernails sailed across them.

"Open the glove compartment." Catherine quietly said.

Michael did so. Inside the small box was totally empty except for a
beautiful multi-colored silk scarf. Following her instructions, he took
it out.

"What do I do with it?" he asked.

"Put your hands behind your back." she said.

Holding the scarf in one hand, he did so. It was immediately apparent
that she intended to tie him up with it. A burst of fear flashed in his
mind. It was one thing to fantasize about being tied up, but to actually
be helpless was another thing.

"Wrap each end around your wrist as far as you can." she continued.
"Then pull it tight."

Michael did so. His hands were now tightly bound. If he simply let go of
the scarf, he would be free.

"You don't get it, do you?" Catherine asked.

Michael didn't have to answer. His facial expression told it all.

"You control the game." she said. "You have the power to end it anytime
you wish. All you have to do is relax your hands and let go of the
scarf. Do you understand now?"

Michael nodded his head to say yes. It was an exciting concept. To
surrender control, yet to hold the key to your captivity in your hands
all the time.

Catherine leaned over and pressed her lips against Michael's. Her
lipstick tasted of cinnamon and as she pressed her tongue into his
mouth, that sweet taste spread throughout it as well.

Her fingers pressed down on the crotch of his pants, closing around his
still hard cock, giving it a playful squeeze. She pumped it a few times,
just enough to send tiny sparks to his brain.

Suddenly she laughed and moved her hand to the stick shift. Catherine
pushed the car into gear and pressed down on the accelerator. The engine
roared and the tires screeched as the Porche swung away from the curb
and down the street. They turned onto 12th Ave. and drove for a little
while along the Hudson River.

Traffic soon grew heavier as they came to a complete stop behind a
tractor trailer. There was a second large truck to Catherine's left. On
the right was a row of long empty warehouses.

Even with his limited time in Manhattan, Michael knew that 12th Ave. was
the worse route you could take at this time of night. All the truckers
came this way causing traffic jam after traffic jam. The night was not
turning out like he expected. He turned to say something but a long
slender finger pressed against his lips kept him silent.

Her fingers then went to right back to his cloth covered hard on.
Michael figured she was just going to rub him a little more. He was
shocked when she pulled down his zipper and reached in and pulled his
cock free.

"Fuck!" the young man exclaimed as his cock sprung upward. He quickly
looked right and left to see if anyone was looking. From the high
vantage point of the truck cab next to them, you could look right down
into the much lower sportscar. Thankfully, the rider in the passenger
seat seemed involved in deep conversation with the driver next to him.

Catherine gently scratched her long red nails along the length of his
rod, making Michael moan.

"I'm going to keep you so hard for so long and make you come so hard,
you're never going to want another woman. After all, I'm the girl of
your dreams, aren't I?"

Michael didn't have a chance to answer as Catherine bent over and took
his cock in her mouth. The wetness and warmth of the older woman's mouth engulfed him expertly. She continued to run her long fingers up and down
the length of his stiff cock, causing it to grow even harder,

Catherine tongued the tip of his cock, licking the small drop of pre-cum
that had formed there. Then she ran her tongue down the length of his
shaft and swirled it around his balls. Up one side and down the other, following the trace she had left with her fingers a few moments before.

Reaching the base, the red garbed woman sucked on his balls, taking
first one then the other into her mouth. Then she let them both slide
free and moved back up his now wet shaft.

In a sudden fluid motion, Catherine engulfed the full length of his
shaft, sliding it all the way down her throat. She let it slide out
slowly, then swallowed it once again. A fire filled her as all her pent
up desires centered on the taste, the touch, the scent of the young man
before her.

Michael was in heaven as every touch of her tongue sent delightful
sensations across his helpless body. He could feel the rising eruption
building in his balls, knowing that it was going to be impossible for
him to hold out for long. Part of him wanted to delay the inevitable, to
make it last as long as possible. Another part screamed to unleash all
the power of his young manhood in one explosive salvo.

Opening his eyes for a moment, Michael looked up and saw that the empty
window of the truck cab was now filled with both the driver and his
shotgun rider. Evidently they were enjoying the show. Shutting them out
of his mind, he concentrated instead on the incredibly talented mouth
gliding up and down his cock.

Moments later, Catherine felt the first drops of warm cum splash against
the back of her throat. She deep throated Michael's cock and swallowed
the steady stream as fast as it came. It was obvious that she loved the
taste of a man in her mouth. Not a drop was wasted.

She let his now empty cock slip from her mouth. Savoring the tangy
taste, she ran her tongue across her lips. She lifted herself up and
noticed the two truckers looking down at them. She smiled back at them
and again gunned the engine as she cut in front of them, across the
other lane and then up the block. "That was fun." Catherine said as they finally slowed down.

"Yeah...fun." Michael said as he wondered how they had avoided plowing
into oncoming traffic. "Could you possible zip me up?" he asked as they
came to a red light.

"I guess so, if you really want me to." came her reply as she looked
down at his cum covered but still hard cock.

With one hand on the wheel they moved forward as the light turned green.
As she drove, Catherine slid his cock back in his pants and pulled up
his zipper.

"Thank you." he said.

Catherine drove more conservatively as they crossed midtown and finally
pulled up in front of a pre-war apartment building that just reeked of
money. Catherine opened the door for Michael this time as his hands were obviously occupied. She draped his jacket over his shoulders and guided
him toward the large carved and oversized doors. As she passed the
doorman, she tossed him the keys to the Porche.

Michael noticed that the doorman didn't seem surprised to see Catherine
leading a young man at least ten years younger than her. He guessed that
money turned a blind eyes to a lot of things.

On the elevator ride up to the penthouse apartment, Catherine kept his
hard on stiff with her teasing fingers and equally teasing voice.
Ignoring two couples that stood at the front of the elevator with their
backs to them, she whispered obscene suggestions into his ear.

Once at her apartment, she led him still tied into the bedroom. There,
instead of turning on the lights, she lit a number of scented candles.

Walking up to him, she undid the buttons of his shirt and pulled it down
his arms. With his hands still tied, she couldn't take it all the way off.

Unbuckling his belt, Catherine let his pants drop to the floor. His
underwear followed. Michael stepped out of them and she kicked the pile
of clothes across the room.

"If you'd like to get rid of this as well," she said as she pulled on
his undershirt. "I'll let you undo your hands for exactly fifteen
seconds..." she paused for a beat and added. "Starting now!"

As fast as he could, Michael did as he was told. He barely got the scarf wrapped back around his hands as the second hand of the wall cock ended
his precious few moments of freedom.

As the last of his clothes hit the floor, Catherine walked up to his
smooth, lightly haired body and ran her nails across his chest.

"I guess they grow them good on the farm". She laughed.

Then with a sudden motion, she grabbed his cock and pulled him over to a
small wooden chair in the center of the room.

"Sit!" She commanded.

Reacting instantly, the former Indiana farm boy landed his ass on the
hard wooden chair with a bang. He had reacted without thinking, a fact
with made Catherine very happy.

Taking a few steps back, Catherine reached behind her and unzipped her
red dress. Leaning over, she gave Michael an unrestricted view of her
round firm breasts. Then she let the front of the dress fall free,
giving him an even better look.

"Do you like these?" she asked as she squeezed each mound and rubbed her fingers over the already hard nipples.

"Yes, Ma'am." Michael replied as the watched the candle light bounce off
her creamy skin.

Clad only in a pair of red silk panties, Catherine moved closer until
she straddled Michael in the chair. Dancing to an unheard music she
swayed back and forth, continuing to play with her breasts just inches
from the young man's face. Her nipples were close enough that Michael
could've just reached out and touched them with his tongue. That is if
he had the nerve to try.

Catherine continued her dance, lowering herself onto his lap, inch by
inch. Her satin covered ass pressed hard against his erection, causing
Michael to moan softly. She slid back and forth, stroking his cock with
her soft cheeks.

Her long nails ran across the soft hair of his chest, stroking his own
tiny nipples. Pressing her face against his pecs, she tickled his
nipples with her tongue, drawing circles around them.

Lifting her left breast in her hand, she guided it to Michael's mouth.
There was no mistaking the invitation. He opened wide to accept her
offering as she pressed her flesh into his mouth. The scent of her
perfume filled his nostrils as he sucked on her breast. Catherine
stroked the back of his head and whispered words of encouragement as she switched breasts, urging him to feast on her other mound.

"Mmmm...very good." she purred as she arched backward and enjoyed his attentions.

While Michael enjoyed his repast, Catherine continued to rub her ass
against his cock. The friction of silk against flesh gave him a euphoric sensation. She knew if she kept this up for long her expansive panties
would soon be covered with cum.

The tall woman climbed off her young lover and gave his now totally
erect cock a playful tug. She bent over and gave it a tiny kiss as well, licking a small pearl of white that had formed at its head.

"Are you enjoying yourself?" She grinned as she gave him another kiss,
this time on his lips.

"Oh yes." he replied ecstatically as her lips left his.

"Do you want to stop?" she asked.

"Oh no." the young man said even more excited tone. "Definitely not!"

"We shall see..." Catherine said, her statement hanging in the quiet air.

Catherine raised her left leg and brought it to rest on the edge of his
chair. She again ran her fingers through his short brown hair. Her hand continued along the side of his face, gently stroking it.

"You are a very handsome young man." She said as she removed her hand
from his face and ran it down the valley between her breasts.

Catherine continued downward and gripped the thin elastic of her
panties, her crotch only a few inches from Michael's face. As she began
to pull the material down to expose her sexuality, Michael hoped he
remembered everything he'd learned from his limited experience trying cunnilingus with the girls back home. The thin red panties fell to the
floor as Michael's mouth fell open. No sound issued from his lips. The expression on his face could only be described as one of shock. Hanging
between her legs was a cock that was larger than Michael's own. Totally hairless, it hung semi-erect less than an inch from Michael's mouth. The
image was so out of place with that of the exquisite woman in front of
him. The young man's eyes darted back and forth between Catherine's
beautiful face and the inexplicable secret between her legs.

------------------

"Yo... you're a guy..." he finally gasped. Catherine smiled down at him.
"Do you really believe that?" she asked.

The expression on the bewildered young man showed that he didn't know
what to think. Time stood silent as he tried to understand.

"Think about what you've been feeling." she continued. "Think about your fantasies and desires."

It was obvious that was exactly what he was thinking.

"Remember, you're in control here." she reminded him. "If you want to
end it here, all you have to do is relax your hands and let that scarf
fall to the floor."

It was that simple. Michael knew it. A simple relaxing of his hands and
he was on the way out the door. Why couldn't he bring himself to do it.

Staring at the cock hanging just before his eyes, Michael thought of the
times he and Jimmy Craig had jerked off together back home. A few times
they'd even jerked each other off. He remembered that it had felt pretty
good. Just as good as when Sally Hayden, his first real girlfriend, had
done it later on. There were nights that he had wondered that if he
hadn't become involved with Sally, would he and Jimmy have gone any further.

"Decision time." Catherine said, breaking a prolonged silence.

Michael knew he should let go of the scarf. Just relax his fingers and
stand up. That was the right thing to do. Instead he found himself
leaning forward and taking Catherine's cock into his mouth.

Surprised at his own actions, Michael couldn't really put words to the
thrill that ripped through his body as he felt her hardness fill his
mouth. A tangy taste so much like his own, which he had tasted many
times, covered his tongue. The fact that it wasn't his own brought a
special excitement to it.

Catherine stood motionless, letting her young lover adjust to the new experience. Michael could feel her cock growing to a new hardness as he
let it slip between his lips and ran his tongue around the bulb like
head. He drew in a breath of air through his nostrils, reveling in the
thick scent of cock and balls.

The now fully erect cock jerked to life, hitting the back of his throat. Michael worked his vibrating tongue across the length of his prize,
nuzzling her naked balls. Once he started, Michael knew he couldn't
stop. Confident now that Michael had made his decision, Catherine began
to slide her cock in and out of his mouth, taking control of the
experience. Her action seemed to add to his excitement.

Faster and faster she began to pump his virgin mouth, offering
suggestions to him as he eagerly followed every one.

The young man's technique was crude, but no more than Sally Hayden's had
been the first time she had sucked Michael off. As with Sally, he more
than made up for lack of experience with enthusiasm.

A few hours ago, Michael would've never believed he would enjoyed the
feel of a hard cock sliding in and out of his mouth. His own cock was
harder than he could've imagined. This was a fantasy that he never
would've even admitted to himself.

Catherine held the back of his head tightly as she felt the familiar
pressure building inside of her. Seconds later Michael's mouth filled
with a creamy whiteness.

"Oh God yes!" Catherine exclaimed as she felt her energy drain into the
young man.

The excitement of a virgin mouth added to her climax as she pumped every
last drop of her orgasm into Michael. The young man gagged a little
until he opened his mouth wider to let some of her seed splash down his
chin. It felt strange, it felt forbidden...it felt wonderful.

Drained, Catherine let her now softening cock slip from Michael's mouth.
She wiped the sticky residue from his chin with her fingers and then
licked them clean as well. Pressing her lips again against his, she
reached into his mouth with her tongue and sampled her own fruits. "Now
it's your turn." she whispered into his ear in her sexiest voice. "I'll
be right back."

The tall woman moved over to a night table and removed a small jar. She
coated her fingers with the clear greasy gel from the container and then smeared another generous helping of in on Michael's rock hard cock. With
all the excitement of the last hour, just her touch was almost enough to
cause him to explode.

"Not yet lover." Catherine said as she squeezed the base of his cock in
a way as to stem a rising tide.

Once more Catherine straddled her young captive and lowered her ass
against his rising cock. She placed a soft hand alongside his hardness
and guided it to her tight hole. Michael felt a great tightness press
against the head of his cock as she pressed down against his manhood.

The pressure increased dramatically as Catherine took more of him within
her. Michael couldn't believe the tightness of her ass, or how good it
felt around his cock. No girl had ever felt this great - not even Sally
that first time in his father's pickup.

Catherine's pace began to increase as she rode his cock faster and
faster. With it grew Michael's pleasure. She slammed her ass against his
balls again and again, driving him deeper and deeper inside of her.

"Fuck me lover!" she called out. "Fuck your woman!"

In every aspect of his mind, that was exactly what she was to Michael.
She might have a slightly different anatomy than he had expected, but
she truly was the girl of his dreams.

The tension in his cock could be felt all the way down to his toes as
the rising tide Catherine had paused a few minutes before returned with
double the intensity. His lover recognized the tightness in his groin as
she pressed against it once more.

Catherine pulled Michael's face against her breasts as she slammed down
once final time. An action that burst the dam within him, sending a
raging torrid into the tight confines of her ass.

The sudden release caused Michael's entire body to relax. Like a rag
doll he lost all strength in his extremities as it was replaced by a
crashing wave of euphoria. He opened his mouth to speak but didn't have
any energy to do even that.

The young man collapsed against the back of the chair, his head resting
in the bosom of her breasts. She wrapped her arms around him and held
him close, even as she felt him grow soft inside of her.

He had been fun, as the smile on her face attested, the best she'd had
in a very long time. Michael had genuinely believed in their little
game, something very rare in her conquests. He might very well be the one.

Normally, Catherine preferred virgins, only playing the game once with
each new lover. This time however, she was sure there would be a second act.

END

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Ann Douglas
Ann Douglas
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COMMENTS (11)
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11 COMMENTS
paulthewetcdpaulthewetcdover 1 year ago
Wow!
The intense passion of these characters is palpable....

Although I knew from the start that this was a transgender story, I was captivated by Catherine and her femininity...

There is no doubt that I would have made the exact same choices as Michael...start to finish!

And, oh, what a finish!!!

Your writing is clearly emotional, sensuous, and sexual....erotically fulfilling.

And I impressed that you made it so wonderfully compact ....

Thank you for giving me this...beautiful feeling!

Anonymousabout 2 years ago
Beautifully erotic
A really lovely, well written and erotic story. Your ability to
empathise with the male experience is impressive. This is an exciting
fantasy for me, and reading it brought me a lot of pleasure. Thank you x

oldpantythiefoldpantythiefover 2 years ago
Over the top!
So much feeling and passion in such a short story. Well written, as
always, and so hot! Thanks again.

Anonymousalmost 3 years ago
Revisiting
I first read this story a very long time ago on a different platform and
it has popped into my mind every once in a while since then, although i
have not read it again until now. Thank you.

Anonymousalmost 3 years ago
Lovely story
What a lovely erotic, even romantic, story. It captivated my attention
and got me more than a little excited!

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