As promised, here are a few pictures of my sissy slut from our previous sessions. She loves being put in her place. Soon she will be posting her drawings that she loves jerking her tiny cock to. They'll accompany my story.
My sissy didn't listen to the rules, no dressing up when I'm not home. Mistress was not happy.
Under my control
As punishment she had to clean my heels. I wore them on my date with a real man.
Sissy Katy Glossy holding her drawing she was caught jerking her pathetic cock to.
Tools needed for a Sissy to make her sad attempt at being an true woman.
I hope you all enjoyed the pictures. I know we did taking them. ;-)
I'm sorry for the delay. Below is our first story. Within the coming week we will be posting the drawings. I'd post it now but my Sissy, Katy Glossy wants to perfect them. Let us know what you think and if you have any suggestions.
He excitedly stumbled out of the car and ran up to
the door. The packages fumbled in his hands as he rushed into the house. Nathan
loosened his tie and tossed it to the ground along with his blazer coat. He
kicked off his shoes and walked over to the table to set down the boxes. After
taking a moment to select the perfect wine bottle he poured himself a glass and
walked to his precious boxes. After a big gulp of wine he quickly tore open the
boxes and gingerly held up the items. The satin lingerie was smooth beneath his
fingers and the dress was a vibrant dark red. Nathan placed the dress down on
the table and went upstairs to retrieve the perfect shoes and pantyhose from
the bedroom. The lingerie and padded body shaper firmly in his hands.
He opened the drawer where Jane kept all her
delicates along with her pantyhose. Without a second thought he reached
directly for the pair pantyhose that he has been counting down the days until
he could wear it. Jane often bought shiny, high gloss, pantyhose but she rarely
had the opportunity to wear them since they would be inappropriate in a school
setting. He always thought it was such a shame that others didn’t have the
opportunity to appreciate how magnificent her long tanned legs look in a pair
of tight, glistening, nylon and now he finally had the chance to feel the luxury
that Wolford offered in his hands. The smooth, soft, pantyhose slide between
his fingers as he laid it delicately on the bed alongside the lingerie and
padding. He headed to the bathtub and dropped the remaining of his conforming
male clothes to the ground. The tub filled with water as he grabbed the bottle
of red wine they often leave by the bathtub for spontaneous moments. Warmth
spread all through his body as the red wine took its effect on him, he smiled
to himself, satisfied with the desired effects. He slipped into the bathtub,
and allowed the warm soapy water to soften his rough skin. After a few minutes
of soaking he brought his legs up to shave what little stubble has formed on
his legs and arm pits. When Jane and him became intimate he explained to her that
he was an avid swimmer and often shaved his body hair to retain his speed.
Swimming gave him his desired body type. It offered the cardio needed for a
healthy life style and kept his slender frame from gaining too much muscle. He
also wasn’t a fan of working out next to the much bigger and taller men. Being
only 5’7” with a 30” waist, he often felt insignificant next to the other men. Men
that he knows Jane fantasies about while they are in bed together. He didn’t
blame her, sometimes he got off to fantasies of Jane fucking and sucking other
men too.
Nathan rose out of the bathtub, wrapped himself in
Jane’s plush towel. Wine bottle in hand he walked over to her vanity mirror and
grabbed her Paris Hilton shimmering body lotion that smelled like sweet candy.
It glided easily over his smooth legs and arms, giving him a slight glittering
sheen. He took another large swig from the bottle and put on the shape wear.
The padding gave him the hips and ass he lacked to look like a real woman. Over
the shape wear he put on his lingerie, using rolled up pantyhose as padding for
his breast. He sat on the bed and positioned the pantyhose at his foot,
finally, the moment he’s been dreaming of all week. The pantyhose glided over
his smooth tan legs, feeling the tightness of the nylon encapsulating his leg
brought a freedom he could never explain. He had to shimmy a little to get the
waist over his new hips. Once the pantyhose were pulled up he let the waist
band snap back against his torso. It was like he had a hit from his favorite
drug.
Nathan slipped on the tight black slip he bought a
long time ago for Jane but rarely ever sees her wear. He stopped for a moment
to study himself in the mirror.
“Not bad.” Nathan smiled at himself as he ran his
fingers over his new body and his thighs. He lingered over his crotch and
rubbed at his semi-erect cock, bringing it to full attention, or as much as
possible with all the constricting layers he had on. “The heels are gonna look
amazing and really make my ass stand out more.”
Immediately his eyes zeroed in on the red shoes when
he walked into the closet. He grabbed them, walked over to the bed, and sat
down to slide on the 5 inch heels. After buckling the ankle strap, slightly
tighter than most would allow, he set his feet down on the floor. He took a
deep breath and attempted to stand in the shoes and wobbled a bit.
“Maybe I had a little too much wine.” Once he was
balanced he took a few steps around the room and settled at her vanity mirror, ready
to apply makeup.
His breath caught in his throat and for a moment he
forgot how to breathe. The car ignition turned off and the sound of Jane
arriving early echoed through the house. He was frozen in place. It was his
quick thinking and action that averted an untimely coming out in the past, but
this time he didn’t respond, at all. This time he was too engrossed in his new
items to hear her car pulling into the driveway.
From his frozen position he saw Jane stroll quickly
up the drive way to the door. She had on a light blue blouse, her cleavage exposed, and a black pencil skirt that stopped just before her knees. Considering she is a
high school teacher her look was more revealing than expected. She had on heel shoes and her
long dark brown hair was pulled into a low lying bun. Surprisingly, she was wearing shiny black
pantyhose instead of her boring nude matte pantyhose.
He heard the front door
slam from the bedroom and at that moment he remembered the dress he laid out on
the kitchen table downstairs. Forgetting
what he was currently wearing he finally sprang into action. Nathan stumbled up
wearing the 5 inch high heels, sloppily teetering towards the door in a vain
attempt to run downstairs fast enough before Jane could see the dress. He heard
the sound of the alarm being turned off, she was at the bottom of the stairs
tossing her purse to the side.
She looked over to the
table and saw Nathan’s clothes tossed to the side, wine glass on the table, and
a dress.
“What the fuck?” Jane
said softly but in a harsh tone.
Nathan quickly turned to
leave realizing the horror that each satisfyingly constricting item of clothing
has been put on display for Jane’s eyes to see. His quick movement to the
bedroom cause him to trip and fall to his knees near the door way. “NATHAN! WHAT THE FUCK
IS GOING ON?” Jane yelled as she quickly walked up stairs.
The sound of her voice
and how close she was sent a chill and thrill down his spine, Nathan’s heart
pounding fast in his chest. This was it; he was going to be caught wearing her
brand new pantyhose, lingerie, and high heels. Knowing how close she was to finding
him caused his cock to grow hard under the layer of pantyhose and tight
panties. His nightmare and dream where about to come true.
“What the fuck!” When
she reached the top of the staircase she saw a sight that nearly left her
speechless. But she forced a few choice words. “Who the fuck are you – who the
fuck do you think you are coming into my home with MY FIANCE! Turn around right
now you fucking bitch!”
Nathan slowly turned
his body to face her. He was still on his knees, dressed like slut and wearing
feminine shape wear with an illusion of fake breasts and hips with her new and
expensive pantyhose. Complete and utter shame on his emasculated face as he
looked at her. His face blushed with humiliation, flushed bright red. Yet his
cock stiffened from under the constricting shape wear. It barely made an appearance
but there was no doubt in Jane’s mind that he had an erection. ‘Pathetic’, she
thought to herself.
“What the fuck are you
doing?! What are you wearing?! Where the fuck did you get that thing, are those
tits on your chest?! What are you fucking gay? Are you a faggot? No, forget it
I don’t wanna know I’m leaving.”With
that Jane turned towards the door.
Nathan called for her
wait. “Please lemme explain! I’m not gay please hold on!”
Jane stopped and took a
deep breath. A million thoughts ran through her head but the one that stood out
was that she could use this to her advantage. She turned around and stepped
closer to Nathan, walked around him and studied everything he had on.
“Please, Jane, say
something. I can’t handle how quiet you are.” Nathan peaked at look at her from
under his eye lashes, his eyes lingering at her long legs, her strong but
smooth calves.
“Stand up.” Her tone of
voice proved she was not to be questioned, carefully honed over many years of
teaching teenagers.
Nathan reached for the
heels to take them off so that he could stand easier.
“Did I say you can take
them off? I said stand up, I did not give any other instruction.” Jane took a
step back from him and tapped her shoe against the hardwood floor.
He struggled to stand
up while wearing the 5 inch heels. After a few near stumbles he shakily stood
before her. She walked around Nathan, inspecting his body in the slutty outfit
he picked out. Even with 5 inch heels he was barely taller than Jane’s 5’10”
statuesque body. She recognized her slip that he bought her, the whore shoes
she refuses to wear, and her expensive pantyhose that she works hard to buy.
For a moment she almost forgot her plan and unleashed all her anger but she
composed herself.
“Well, it looks like
you like to steal my things. Those are my new pantyhose!” Jane said as she lifted up the slip.
“Jane please lets –“
Jane held her hand up
to him and shushed him. “I don’t believe I said you can talk yet. Considering
that I’m the one who is in the right, we’re gonna do things as I say. Is that
understood?”
Nathan nodded his head,
his gaze still glued to her legs.
“I can’t hear you.”
“Yes, Jane.” Nathan
said softly, his hand gravitating to his crotch, in a vain attempt to hide his
growing erection.
Jane noticed this and
realized that he must have a thing for being controlled. “Actually, from now on
you’ll refer to me as Mistress Jane or Madam. Is that understood?”
“Yes, Mistress Jane.”
His hand finally reached his cock and tried to apply a little pressure to
relieve the strain.
“Obviously you enjoy
being told what to do. A real man doesn’t allow himself to be controlled by a
woman, he controls the situation. But here you are, dressed like a slut and
allowing your woman to command you. You’re not a man, you’re a sissy. That’s
what you’ll be called from now on. You will respond to Sissy, Nathan is no
longer your name. Is that understood?” Jane placed her hand under his chin and
lifted it to look at her.
“Yes.” He couldn’t look
her in the eye, instead he focused on red lips.
“Excuse me? Yes, what?”
“Yes, Mistress Jane.”
Jane grabbed his hand
away from his crotch. “I didn’t say you can touch yourself!” His hard cock was
evident, even under all his layers. She smiled and realized he was going to be
easy to control. “Gosh, you are such a pathetic sissy. You are loving this
aren’t you? You like having me control you and tell you what to do. You are
such a loser.” She walked over to the vanity and pulled out her make up kits.
“Sit.” Jane commanded
Nathan.
He sat down, scared and
excited for what was about to happen.
“I have very exciting
plans for you in this outfit for tonight. But we need to finish the look.” Jane
whispered in his ear. Her breath warmed his ear and sent a tingle down his
spine. He took a deep breath and savored her warm body near his and the scent
of her perfume, Channel no5.
She pulled out the
foundation, eye shadow, liner, lipstick, and blush and proceeded to apply
makeup on her sissy. Her touch on Nathan’s body electrified him. When their
pantyhose covered knees slid against each other he nearly convulsed. When she
placed her hand on his thigh and ran her fingers over his pantyhose he knew
that he would do whatever she asked of him.
“Okay, all done. I must
say, you don’t look half bad. You almost look passable. Especially with your
longer hair. Hmmmm… I have something that would really make you look perfect
for tonight.” Jane walked away into the closet and left Nathan to his own
thoughts.
He studied his face and
couldn’t believe how much he looked like a woman. Jane created perfect contours
and made his green eyes pop with the smoky eye shadow. His lips were plumped
with a lip plumper and they looked amazing with the pink shimmery lipstick. The
blush highlighted his high cheekbones and gave him a sexy flushed look.
Jane walked back
holding a blonde wig with long wavy strands. “I knew this would come in handy
someday.”
“When did you buy a
wig, Mistress?” Nathan asked as he watched her put the wig on him from the
mirror.
“I wore it as a
Halloween costume before I met you. I was a slutty Barbie. How appropriate that
I’m now using it for you.” Jane smiled when she saw Nathan blushed at being
called a slut. She situated the wig properly and positioned the bangs. She told
him to stand up and took a step back to take in his whole look. It was amazing
how much he could pass as a woman. This was going to work perfectly.
“Come on, you need to
look at yourself in the full length mirror. It’s so depressing how much you
look like a fucking loser, sissy.”
Jane positioned Nathan
in front of the mirror and he nearly came in his panties. He has never looked
this amazing. If he saw a girl that looked like him at a bar he would have a
long maturation session to thoughts of her. And now before his eyes he is the
hot girl he will be masturbating to.
“Time for the final
piece. Come downstairs.” Jane’s hips swayed as she walked down stairs. Nathan
obediently followed behind her, though at a slower pace because of the heels.
As he walked he noticed his hips fell into a natural swing.
When he reached the bottom
of the stairs he saw Jane holding out the dress to him.
“Put it on.”
“Okay, why are we doing
all of this? I’m really confused here Jane. And why are you home in the middle
of the day? We should stop and talk about this.” Nathan realized how ridiculous
his speech was as he stood before her dressed like a whore.
Jane’s eyes were fierce
as she walked up to him, dress firmly in her fist. “You might want to rethink
the way you are talking back to me. For reasons I’ll explain later, I have
cameras set up in the bedroom, the feed is sent to my laptop. It’s set to turn
on everyday around this time. Everything you’ve done since just before I
arrived home has been recorded. Need I explain what will happen if you disobey
me?”
Nathan’s stomach turned
into knots. ‘What is she recording? Why does she keep saying that he will look
perfect for tonight?’ He thought to himself. His weak arm reached out for the
dress and pulled it over his head. While he was adjusting his dress he felt
Jane fumbling around his ankles.
*Click* *Click*
He looked down and saw
the luggage locks locking his 5 inch heels in place.
“Just in case you get
any ideas about taking everything off when I’m not looking.” She smirked at him
and place the key in her bra.
Nathans mind raced with
frantic thoughts of what was to become of him…
Feedback is of course welcomed and enjoyed. ;-) We're looking forward to it.
