Captivating Catwoman
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Heads You Dress.....Chapter Two free porn video
CHAPTER TWO --- PANTIES & PURSE
1
So, it started simple enough with panties, but for both Jason and Debs
there were going to be some devastating discoveries. However, in those
early days it was fun and games....at his expense, of course.
Jason wore panties to work and on his days off. The choice of underwear
was simply taken from him. He found he didn't mind, even though he didn't
quite understand why he was suddenly being told what to wear. When he
challenged his wife and asked if it was because he enjoyed wearing
panties she merely smiled sweetly. It made him so hot, and he realised he
was excited by his lack of control in the situation.
Each night he went to sleep wondering what he would be wearing the next
day, and he was never less than delighted.
In the mean time, Sabrina and Debs met with Kelly, Jason's fresh faced
secretary. They explained what they planned to do with him and after
several days deliberation, with particular encouragement from Sabrina who
had always enjoyed such games, she signed up to the idea. Literally
signed since Debs offered her a higher paying contract to become Jason's
Office Manager.
"The way I see it," Debs explained over coffee one morning, "I can watch
and control my husband a lot of the time. But work is an obvious place he
could escape our feminisation. So, you can do with him what you like, so
long as he follows whatever his dress code is that day as a minimum.
Currently, that's panties and tights or stockings."
"No bra?" Kelly asked, almost disappointed.
"Sabrina and I agreed this would be a long game. I've got a bra fitting
booked in a few days." Debs smiled. "You're a wildcard in this. Keep
things unpredictable for me."
2
Kelly embraced the notion of her new role. Even had a new nameplate made
up. OFFICE MANAGER. Nice and prominent so that Jason couldn't miss it
when he returned from a house viewing.
"Office Manager?" he asked. "Pretty fancy title."
"Did Debs not fill you in?"
"She said she was making some changes. I thought she meant to do with
what...."
"What are you waffling about, Jason?"
"Nothing."
He entered his office, convinced that Kelly knew he was made to wear
women's panties. Crazy, he thought. But if she did know, should he stop?
Could he? Would Debs even let him?
He'd enjoyed wearing panties all his life, on and off. Sometimes he could
really hate himself for doing so. Never really did get a finger on his
desires. But now he didn't have to worry. It wasn't his responsibility to
choose. He was simply doing as his wife told him and-
Kelly was standing before him. He hadn't heard her come in. Realised his
hand was on his bulging penis beneath the desk.
He smiled awkwardly. Did she know?
"Y-yes," he stammered, afraid to move his hand.
She smiled wickedly. "Stand and take your trousers off."
"Excuse me?"
"You heard me. I want to see what colour panties you have on today. And
take your hand away from your little dick. From what I hear it's not
worth playing with."
Jason blushed absolutely.
"I'm not wearing-"
"My new contract's been on the desk all day. Did you bother to look at
it?"
"No, I just thought it was standard-"
Kelly laughed. "Standard? It specifically states that during your working
hours I am in control of all aspects of your feminisation and that I am
to keep things unpredictable."
"No...." Jason whispered, shocked by the revelation.
"Show me your panties."
He unbuckled his belt and just revealed a peek at his polka dot panties.
She laughed at his shy nervousness. "Get it over with, Jasmine."
"Jasmine? Don't call me-"
"Drop your trousers, Jemma."
"My name is-"
"Jenny," she grinned, and then gasped as his erection stirred. "Yes,
Jenny. Now show me your panties."
Jason reluctantly let go of his trousers and they dropped to the floor,
revealing his polka dot briefs - the front satin panel dampening at the
tip of his erection - and matching garter belt, with lace top stockings.
She giggled and then flicked with amusement at his pantied penis. "Such a
little clitty."
She assessed him.
"Those legs won't do," she smiled, "and I think we'll make this our
regular practice. First thing every morning."
He continued to stir and the damp spot was turning positively moist with
pre-cum. Don't, he thought. But the pressure he put himself under only
excited him further. He remembered a time at college when he had attended
a lecture wearing lacey panties only to find he couldn't control himself
and-
Shit. Standing before Kelly, cum started to leak out.
She laughed. "Get dressed before you have an accident."
But it was too late. The panties were filling with cum. And now he was
stuck wearing them, his deflating penis suprisingly comfortable in the
warm, wet fluid.
"Wait," she said, and returned moments later. "If you can't control
yourself, you'll need this."
She handed him a panty-liner.
"I will not wear that."
She gestured to his panties. "Once your trousers are on, that's going to
soak right through for all to see, unless you contain it."
He put the liner inside the panties as best he could and tucked his penis
onto it.
"I'll set you on a period cycle-"
"What?"
"That way you can have a natural release when you are dressed. Now, pull
your trousers up."
He buckled his trousers and she watched. No stains came through. He
couldn't figure out why, but in his mind her reasoning actually made
sense.
"Good. Now, take a pen and write this shopping list down."
3
At the door, Kelly called him back.
"Don't forget your purse."
"I've got my wallet."
She grinned without humour. "This is your new clutch purse. It's bigger
than average so that you can't hide it in your hands or pockets. Now,
switch everything from your wallet."
He looked at it. "But it.....sparkles."
"It's fashionable, you diva. Don't worry, one day you can choose one you
like. For now, though, this is what you'll use."
Jason switched his cards and cash. Put his loose change in the zip
compartment. He grunted with satisfaction.
"Anything wrong?" Kelly asked.
"No, it's just....Well, it's actually quite sensible. It holds
everything."
"I'm glad you like it. Now, run along."
4
After he left Kelly placed a call to Debs and explained what she had
done.
"That sounds great," Debs said. "But isn't it a little quick. Some of the
things you're doing to him sound severe."
"Sabrina told me to get tough with her. Let her know-"
"Her?" Debs asked, wondering when Kelly and Sabrina had seen each other.
"Yes. Let's get her in that feminine mindset right away."
"You're enjoying this," Debs noted.
Kelly giggled. "Can I tell you something? It actually got me hot. I can't
wait to see..."
"To see?" Debs prompted, wondering why she had left the sentence hanging.
"Oh, just my boyfriend."
For a while they exchanged pleasantries, traded ideas about what they
each might do, but Debs, without appearing obvious, kept circling back to
more personal information. It concerned her slightly that Kelly and
Sabrina had made plans without her knowledge.
Eventually she dismissed any suspicions she had. The bottom line was her
husband had cheated on her, so this was her way of getting payback. If
things moved quicker than she expected, so be it.
5
Jason - he refused to think of himself as Jenny - considered the shopping
list. It wasn't too bad, he thought, even though it did seem a little
extreme:
Tights
Stockings no higher than 10 denier
Women's shaving cream
Pink razors
Work diary something girlie
Always Infinity panty-liners
Always maxi-pads
Tampons scented super with applicator
He baulked at the last one. The way it was written didn't make sense to
him, and it sounded quite daunting. What the heck was an applicator? Even
though he had never worn a panty-liner before, it was actually quite
comfortable. But a tampon....It didn't dare thinking about. Nor, now he
was coming off his high, did having a period cycle. Surely he could
control himself.
At least he could get most of the shopping in one place.
He headed to WHSmiths first. A book shop that sold other bits and pieces
of stationary. He found himself going through several diaries until he
found one that he thought would pass Kelly's inspection. It was cream
colored with a pretty flower motif; lots of splashes of soft colors. He
kidded himself by believing it could be for either gender.
But it could be, he thought, approaching the check-out. Why not? Why does
a guy have to fall into certain categories? Why can't he enjoy the
softer, more feminine things in life?
The woman at the till ran his purchase through.
"I might have the right change," Jason said helpfully, and began to
fumble through the zipped compartment of the purse. He couldn't even hide
it because it was too big to fit in his pockets.
The woman smiled. "Nice purse, Sir."
He quickly left and found a big department store called Boots for the
rest of his items. He picked up a basket and found the hosiery section.
He chose several pairs of tights and stockings, mostly natural but some
barely black. He noted the denier number on each pack, not even sure what
that meant. Something to do with the fineness of the material, he
believed. He chuckled: a fleeting image of his hairy legs through the
tights, but the smile was quickly wiped from his face when he realised
that was what the razors and shaving cream would be for.
He found the shaving cream and girlie razors and then walked hesitantly
into the feminine hygiene aisle. Kelly had been specific. Always Infinity
panty-liners, Always maxipads and the.....He saw the boxes and now
realised what the note meant. He swallowed deeply: super-sized, scented
with applicator.
He quickly picked the appropriate box up and then took his time with the
panty-liners, despite the occasional glance from passing women. If he
purchased the wrong ones he was sure Kelly would send him back which
would be more embarrassing than what he was going through now.
He finally chose and was about to head for the check-out when a text came
through.
TREAT YOURSELF TO A PRETTY LIPSTICK. IT BEST SUIT YOU, OR I'LL SEND YOU
BACK FOR A MAKEOVER.
He sighed deeply, considering the contents of his basket, and then
nervously made his way to the make-up counters. There were several brands
and hundreds of lipstick shades. How the hell was he supposed to know
which colour would suit him?
The answer was right nearby. Each counter had a representative; some busy
with clients, some not. He took a step, but then chickened out.
He nervously watched a woman testing lipsticks on the top of her wrist.
Okay, okay, he thought. You can do this. He discreetly tried a few on the
inside of his wrist, where it could not be seen.
So far, so good. He studied the colours. But how would he know which-?
"The pink one."
He turned, blushing.
The woman was pleasant. Attractive in the summer. Low cut blouse and
skirt. It was a good look on her. Smooth legs, he thought dismally, aware
that his would look the same tonight.
"I'm just pick-choosing-" he stammered, and then muttered quietly: "For
my wife."
"Would you like some help, Honey?"
He looked down and nodded. She knew. She had to know. And what would she
be thinking about the contents of his basket?
"So, who is the lipstick really for?" she asked sweetly. "Just so I can
give you some real help."
Jason swallowed deeply. "Me. It's for me."
He tried to move the tights so they covered the tampons and panty-liners
without her noticing. It just drew her attention to the basket.
She grinned pleasantly. "That time of month?"
"Please-"
"Awful, isn't it? In this heat?"
"I..."
She relented. "I'm just teasing you. My name's Ellie."
She offered her hand. He took it.
"Jason."
"Jason?" she asked. "Do you have another name?"
He didn't want to admit it, but the word came out quite easily. In this
environment it almost sounded natural and he actually didn't mind it.
"Jenny."
"Nice to meet you, Jenny. The pink one," she said quickly, before he
could get hung up on the name.
"But it's girly."
She laughed. "What were you expecting to find in this department, Honey?"
"I guess," he whispered, shuffling on his feet.
"Look, it's soft enough to match your skin tone, with just enough energy
to bring your lips alive. Hold on."
She reached for another product.
"This should do it."
He looked at what she was holding.
"Lip gloss?" he cried out.
"It will really set your lips off. They'll look great in the sun. Here,
let me show you."
Ellie broke the seals and unwrapped the products. He thought she was
going to demonstrate on herself, but froze in fear when he realised what
she was doing. She ran the lipstick over his lips several times,
encouraging him to pout and smack them together. Then she ran the gloss
over his pink lips.
"You look great," she smiled, handing him the products. "Just tell the
cashier you couldn't wait to try them out."
He finally made eye contact with her. Despite circumstance, she had
genuinely helped him out.
"Thank you," he said sincerely.
"Good luck, Honey," she waved pleasantly, and left him in the aisle.
He took a second to gather himself, feeling a little euphoric at the
uninvited acceptance, and headed to the check-out feeling more confident,
despite his lips and what he was purchasing.
The woman behind the counter gave him the look he was expecting, and he
started to crash back down to earth.
"They're for my wife," he said as she began scanning.
She considered his lips, then his purse. "I suppose the purse is hers,
too."
6
Jason returned to the office, aware now - as most women and even some men
stared at his hot lips - that it was pointless trying to hide the purse.
It didn't occur to him to drop it in the bag. It felt natural in his
hand. It was his.
"That's such a cute look on you," Kelly exploded enthusiastically.
He sneered a little.
"Loosen up, Bub," she grinned. "If we're playing these games for your
wife, we might as well have fun."
He tried to relax. "Okay. Where do you want your shopping?"
"My shopping?"
"Yeah, you sent me out and-"
"Jenny, you know where this is going, don't you? That list was made in
your writing. You purchased the items with your cards and cash. Your
first period started this morning, Missy, and-"
"Please just give me a break," Jason protested.
"Look, your wife knows all about what you've been buying, and how excited
you are about what we've done today. So while you're in your office just
think about how quickly we are moving, and what else might happen to
you."
7
Debs arrived later that day, trying not to be suspicious of Kelly. How
eagerly she had jumped into the games they were playing with
Jason.....Jenny, she corrected. What she was talking about with Sabrina,
who certainly seemed to be taking a backseat to the feminisation of her
husband, something she had openly encouraged.
Debs shook her head. She was probably being paranoid because of the
unusual circumstances of what they were doing. But what if....She
couldn't put her finger on it, but somewhere in the back of her mind, she
felt troubled.
"Closing up time," Debs said, entering the office of the real estate
business she had founded.
Kelly looked up with a pleasant smile. "She hasn't come out of her office
all afternoon."
"Well, we can't have that," Debs said. "Tomorrow I promise she'll make a
better effort. Otherwise we'll make more changes in here."
Debs entered her husband's office. "Are you ready, Jenny?"
Jason looked up, ashamed, and Debs got a hot flush. His lips were
gorgeous. She immediately, instinctively kissed him. And somewhere, deep
inside, Jason began for the first time to accept what might be happening,
how comfortable he could be. It had been weeks in panties and now this
sudden advance. It had frightened him. And the mix of emotions.......from
confusion at his own inner acceptance to outright terror at what might be
next.
To, in Debs warm, loving embrace, a comfort he had never experienced
before. An ease with who he was becoming. He felt safe.
"Ready for what?" he asked.
"We need to switch up your clothes a little," she said. "And I think it's
time for your first bra."
Kierra
- 03.08.2022
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