The Silk Scarf – Shemale Erotic Story
Sunday, April 8th, 2007Michael sat at the table playing with his
drink. Heâd gotten his first real paycheck today
and decided he deserved a dinner in the best
restaurant he could afford. Of course which 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 which 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
couldnât 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 couldnât 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 youâre 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.
”Youâre legs are magnificent.” he blurted
out, feeling incredible stupid the moment heâd 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. Heâd
never felt so embarrassed in his life. He wished he
could just run for the door and disappear.
”Donât 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 youâre going to be when I take you home
with me and make all of those dirty dreams of
your’s come true.”
”W-h-at do you mean?” Michael
stuttered.
”What Iâm 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.
”Whatâs 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 drivers 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 Michaelâs 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
it’s 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.
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