Falling For It
Belladonna
[Author's Note: Based on a caption by Commentator]
A smile came upon Joss's face as his gaze drifted across all the
costumed characters in the convention room. He thanked his luck that
his employees had all turned down his offer to take them with him to the
convention. Joss had been going to it for years, and it remained one of
the highlights of them.
He loved looking at the costumed attendees, but, more than that, he
loved being in costume himself. While Joss had bought a male costume in
case his employees came, he was far happier to be wearing his Sailor
Venus costume.
He could barely contain himself as he dressed in the costume earlier
that day. He started by putting on his bra and stuffing it with his
smallest breast forms. As he waited for the glue on the forms set, he
set about bringing a pair of nude pantyhose up his freshly shaven legs.
Joss enjoyed the feeling that enveloped his legs while he covered them
in nylon. Once the control top reached his hips, Joss reached for the
cap sleeved, white dress that was decorated with an orange and white
collar.
Joss stared at the dress for several minutes while he stood before it
clad in his pantyhose and bra. His eyes kept drifting from it to the
accessories he had bought to make the outfit come together. While he
had owned the dress for years, he had decided to take it further than
when he sported it around his apartment.
Once he was certain the glue of his forms was set, Joss pulled the
figure hugging dress over his head and down his body. With the dress in
place, Joss walked into the bathroom to look in his vanity mirror. He
adjusted the large blue bow over his form-enhanced bust with a grin
before he affixed a golden heart shaped broach to completely cover the
knot of the bow.
Joss squealed at the way his modest faux bust looked beneath the bow and
the effect of the thin, form-fitting dress on the appearance of his
slender body. His hands ran down the white, spandex sides of the dress
until they reached the dress's attached, pleated, orange, satin
miniskirt.
"This is going to be the best day of my life," Joss said to himself with
an eagerness for it to be so. He clasped his hands for a moment before
he turned to get a look at the golden bow that rested just above where
his back met his butt.
Tearing his eyes away from his feminized form, Joss turned his attention
to his face. He reached for his blue color contact lens and placed them
into his brown eyes. Joss blinked several times before he focused his
eyes on their change of color. It still struck him how different he
felt he looked with them in his eyes, no matter how often he had worn
different color contacts over the prior few years.
With his eyes attended to, Joss began to put on his makeup. He applied
primer to his eyelids before he brushed an orange color over them. He
then added a bright neon yellow color along the top and bottom of his
lids.
Joss paused to smile at his reflection once more before he reached down
to grab more colors for his eyes. He then applied a coral red color to
the crease of his eyelids before he lined his lower lash line with a
cobalt blue color and winged it up.
After putting down the applicator, Joss's hand reached for his mascara.
He coated his top and bottom eyelashes with it before he took hold of
his pink lipstick. Joss coated his lips, watching the color make them
grow more pronounced the more it covered them. Joss's eyes focused on
his pink lips while he intermittently smacked them together and pursed
them.
Once Joss put down his final cosmetic, he went into his bedroom to
retrieve his wig and tiara headband. Joss placed the golden colored
headband on first and adjusted the V that was centered on the front of
the headband so that it came down perfectly between his eyebrows.
Joss gave his reflection a nod and toothless smile before his eyes
glanced down at the long, blonde haired wig. He checked the tightness
of the large red bow he had tied into the wig the night prior before he
placed on his wig cap and pinned the wig in place. As Joss shifted his
head the long, blonde, synthetic fibers of the wig that extended well
past the hemline of his skirt brushed against the back of his arms and
legs.
Joss grinned at the effect that the wig had on him. He saw not a trace
of masculinity on his face or body. The only hint he saw of it was his
Adam's apple. He did not linger on that for long as he concealed it
with an Orange Choker that was decorated with a centered Gold Star.
Joss felt he looked perfectly feminine in his outfit while he walked
back into his bedroom to retrieve the final two items to complete his
costume. He bent down and took hold of a pair of orange, patent leather
kitten heels with an ankle strap. He slipped his feet into each shoe
and buckled the straps before he stood up and grasped his gloves.
Joss's member swelled while he worked his hands and arms through the
elbow length white satin gloves that were decorated with ribbed orange
cuffs. He wiggled his fingers in the soft gloves, enjoying their
unusually luxurious feeling before his eyes caught site of the time.
"Shit," Joss exclaimed before he took hold of his purse and hurried into
the living room. He sat down and waited a few minutes for his friend to
come over.
With a knock on the door, Joss got to his heeled feet to let his friend
in. Conrad laughed at Joss's appearance before he said, "Dude, I don't
know if I should give you a bro hug or a kiss on the cheek."
"You'd get a knee to the balls if you tried the kiss," Joss replied
before they gave each a fleeting hug.
"You never know, that could be my sort of thing."
"Shut the fuck up, you freak."
"I'm the freak?" Conrad replied with a laugh as Joss's heels clicked on
the tiled hallway floor as he stepped out of his apartment.
"If that's your sort of thing."
"Getting kicked by the balls by a tranny is not my thing," Conrad
retorted with a shake of his head.
"Or say you," Joss replied while he locked his door before they headed
for the elevator.
"Did anyone say anything to you?" Joss asked while they entered the
elevator.
"No. I just got the typical weird looks," Conrad answered as he glanced
down at his own costume before they exited the elevator and headed out
the door to hail a cab.
While his friend continued to give him grief while the cab took them to
the convention center, Joss put the teasing out of mind. He was too
enthralled by his appearance to care.
Joss had been a fan of the Sailor Venus character since the first Manga
serial ran in the late 1990's. Despite his long time desire, he had
never found the courage to dress up as the character before. He was
always fearful that one of his all female staff would show up at the
convention looking for him. This time, however, he had sought out
confirmation that none of them would attend.
Joss was hardly surprised by their refusal. The way they rolled their
eyes when he talked about the convention over the years could not be
missed. They all snickered about his boyish enthusiasm for it, finding
it in stark contrast with his professional stature and appearance.
Their dismissive views of the convention and his invitation brought a
smile to his face while he looked down at his costume. He knew that he
would never have found the courage to put it on that morning without
their outright rejection of his offer. He was getting enough grief from
his friend Conrad about his outfit, but he was not someone he had to see
five days a week.
"Come along, Princess," Conrad said with a laugh, drawing Joss's eyes
away from the crowd.
"This isn't the silver millennium," Joss countered.
"Hey, once a princess, always a princess. It doesn't matter if V's in a
sailor suit."
Joss walked beside Conrad while they continued their way through the
convention, mingling with people as they went and exchanging compliments
about each others' costumes. As they walked away from a crossplaying
couple dressed as Princess Peach and Mario, Joss came to a sudden stop.'
"What's up?" Conrad asked as he noticed Joss's sudden pivot.
"Nothing. I just can't look that way," Joss replied. He began to sweat
as he stared in the opposite direction. His heart raced while he stood
in silent disbelief over what he had seen.
Despite their uniform dismissive statements and mockery about it, he saw
one his employees walking around the convention. She was not wearing a
costume, which only made her stand out more.
'What the fuck?' Joss thought, trying to keep calm and not draw
attention to himself as he saw the girl walking in his peripheral
vision. As she walked behind him, Joss turned his head to face to
Conrad and away from where his employee was walking.
"Joss, are you okay?" Conrad inquired, still seeing the mortified
expression on his friend's face.
The sound of his name caused the girl to stop in her tracks. Olivia's
head jerked towards the feminine figure that stood with the same build
and height of her boss and bore the same name.
She scurried over as Joss continued to try to avoid giving her a chance
to look upon his face. As she reached him, however, Joss knew that
there was no chance of avoiding it.
"Joss?" Olivia exclaimed with a mix of amusement and shock.
"Oh, hi, Olivia," Joss replied, trying to salvage his reaction to her
presence.
Conrad put his hand over his mouth while he tried to stifle his laughter
at his friend's continued noticeable distress at being recognized en
femme.
"Look at you. Are you wearing pantyhose?" Olivia remarked as she
quickly took in his costume from head to toe before she started to
laugh.
"I wasn't too happy about it," Joss lied.
"Say what?" Conrad interjected, not wanting to give his friend any
leeway to explain away his costume.
"Conrad, can we have a moment alone?"
"Alright," Conrad replied with a shrug before he walked away to take in
a group of girls dressed like DC comic book characters.
As Conrad stepped away from them, Olivia grinned at her boss and said,
"You were right, the convention is a lot fun!"
Joss blushed as he said, "Yah, I've had better years."
"What were you then, Wonder Woman, Supergirl...," Olivia teased.
"No. Nothing like that. I was Batman..."
"You definitely don't have the build for Batman," Olivia replied,
cutting him off as she took in his svelte figure that was tightly clung
to by his dress.
"They sell padding," Joss countered, bothered that Olivia dismissed his
truthful answer. While he also had both of the Superheroine costumes
she mentioned, he had never considering wearing either of them beyond
the walls of his apartment.
Olivia gave him a disbelieving look before Joss lied, "I'm only wearing
this because it was my Secret Cosplay costume."
"What's so secret about it? It shows a lot of leg, and they're way more
shapely than I would guessed," Olivia retorted with a smirk.
"No. The secret is what you're going to wear. Somebody put the costume
idea under my apartment door. That's the way it works."
"So, someone at this convention wanted to see Joss Peck in a sailor girl
costume!"
"It's Sailor Venus," Joss corrected his subordinate.
"Oh, my mistake," Olivia replied with a laugh, wondering if Joss thought
that the distinction made any difference to her.
"No, but, yes, somebody wanted me to do this," Joss replied, leaving out
that he was the only person he was aware of at the convention that had
any desire to see him in the costume before it started.
"Did that person do your makeup?"
"No."
"Then, who did it?"
"My neighbor's a beautician," Joss lied.
Olivia shook her head before she asked, "Who wanted you to look like
this?"
"It's a secret. I assigned someone else and somebody else assigned me.
We never get to find out who assigned what character to whom. That's
part of the fun."
"Well, it's definitely a lot of fun for me!"
"I'm so sure," Joss admitted with a laugh.
"I never would have guessed that you'd look so pretty. I need a
picture."
"No pictures!"
"Oh, please. You've been in the background of like 8,000 pictures since
we've been standing here."
"Fine," Joss relented, knowing that he did not have much support for his
reluctance.
Olivia did not wait long before she wrapped her arm around him and took
a quick selfie with her short-skirted boss.
"Are you wearing color contacts?" Olivia noted with a laugh as she gave
his eyes a closer inspection before she released him.
"That's what color my character's eyes are. You have to go all out with
this sort of thing," Joss responded, trying to explain himself.
"Really?" Olivia replied as she pulled up images of the character on her
phone.
"Yes. The fun of this is not just dressing up in any old thing. It's
really going all out to make the look happen," Joss explained.
"I could see the fun in that," Olivia admitted while she gazed down at
pictures of the character.
Joss nodded before she added, "But I can see once place you cheated."
"Where?" Joss demanded to know.
"Your heels are way chunkier than these," Olivia replied as she pointed
to the image.
"She doesn't wear stilettos all the time," Joss retorted with a shake of
his head as he looked at the image Olivia had selected.
"Or so you say..."
"No, look at other pictures. They're just trying to sexualize her,"
Joss demanded.
"So, you think you're sexy enough without them?" Olivia asked with a
laugh.
"I didn't say that. I was talking about her."
"So, you think a cartoon character is sexy?" Olivia inquired with raised
eyebrows.
"Well, what about Jessica Rabbit?" Joss rejoined.
"You're not helping yourself," Olivia retorted with a laugh.
"I know," Joss admitted with a self-disgusted shake of his head.
Olivia put her phone away while she shook her head and said, "Well,
you're a smart girl for not wearing pumps. A lot of guys would have
been stupid and gone all out. At least, those guys who would actually
do it..."
Joss blushed at Olivia's teasing before he said, "If I thought I needed
stilettos, I would have gone for it."
"Oh, please if you wore thin heels, you would be falling over left and
right."
"That's not true. You think only girls could wear them?"
"No. If a guy was experienced, he could do it too. I've seen plenty of
Queens pull it off."
Joss shook his head as he said, "I could do it."
Olivia was surprised by his forceful declaration. Joss had countered
her as a point of pride. He had long mastered the art of walking in
stiletto heeled pumps and boots around his apartment for his Zatanna and
Catwoman costumes.
"You seem certain about that," Olivia replied, not hiding her intrigue.
"I know I could do it."
"Is that why you make us do it?" Olivia asked on behalf of all of her
fellow employees who were not present at that moment.
"No. That's about presenting a professional look."
"A girl doesn't have to wear heels to look professional. You know in
England, there was whole big backlash against a company for your type of
dress code."
"Flats are not professional," Joss countered.
"But for men they are?" Olivia rejoined.
"Yes!"
"Well, now, that we know you can walk in kitten heels, why not spend a
day in our heels, you know, out of solidarity, sister?"
"Oh, you'd just love that," Joss retorted.
"Yes. I would," Olivia admitted with a laugh and a few nods.
Joss laughed as well, knowing that all the girls would enjoy it. It
might even improve morale in the office if he did it. He also knew that
no one had stopped by the office unannounced in years.
As Joss mulled over the idea, Olivia added, "You know that there's a
mile walk every year where men walk in heels."
"I'm aware," Joss admitted. He also knew that Olivia's picture with him
would make its way around the office in no time no matter how he
responded to Olivia's idea. A day in heels did not seem like it would
make the teasing he was going to receive any worse.
"You know what, I'll do it," Joss added.
Olivia gave him a grin as she inquired, "And you're going to wear heels
for grown up women, not little girls?"
"These are in women's sizes," Joss countered before blushing at his
attempt at self-defense.
"No. I mean high heels. At least three inches and not chunky."
"I let you wear chunky heels," Joss rejoined.
"But we can't do it every day. A girl needs some variety. You know how
girls get about girls who wear the same thing everyday."
"Okay fine."
"I'll pick out your pair."
"You will?" Joss countered.
"Yes. They'll have three inch stiletto heel, nothing more."
"I can do that with ease."
"You want to make a bet on that?" Olivia retorted with a smirk.
"So, now, you want to make it interesting?" Joss inquired with a laugh.
"Well, only for you. It was already pretty interesting for me!"
"So, I get nothing if I win?"
"Just the satisfaction of proving me wrong and that your dress code is
not all that bad."
"What are you thinking?" Joss inquired.
"If you don't make it through the day without falling, you have to do it
all over again, and we get to add one more thing to make the next day
harder."
"Like what?"
"Just something else that all the girls have to deal with. You know
that walking in heels doesn't exist in a vacuum."
"I don't know."
"Oh, so, NOW...you're not so confident about making it through ONE
FREAKING DAY!"
"Freaking?"
"A little too public for me to curse loudly," Olivia explained herself
with a smile.
"It wouldn't be lady like," Joss teased.
"You're subject to those rules today too, toots," Olivia kidded her boss
in response.
Joss nodded, thinking it was an innocuous bet under the circumstances as
he responded, "We'll take a vote on Monday. If the girls are onboard
with this, I'll do it."
"Oh, they're going to be onboard, so, are you sure?" Olivia inquired
with haste.
Joss nodded before he motioned for Conrad to come back over to them.
Joss introduced Conrad to Olivia before Olivia joined them while they
continued to make their way through the convention hall.
Conrad and Olivia began to tease Joss in tandem while they walked around
the convention. Olivia smiled as she asked Conrad, "What's his
character's name again?"
"Sailor Venus."
"Sailor Venus?"
"She's one of the Sailor Soldiers along with Sailor Moon, Sailor
Mercury, Sailor Mars, Sailor Jupiter, Chibi Moon, Sailor Pluto...
"How do you remember which one he is?" Olivia replied, cutting off
Conrad's ongoing answer of names he was counting off on his fingers.
"His rhymes with penis," Conrad responded with a smile.
"How appropriate!"
"Har, har," Joss interjected with a shake of his head.
"And from the looks that some of these guys are giving him, I bet they
want to give him a little of their...," Olivia started to tease.
"Alright," Joss responded, cutting her statement off.
"The only one I ever heard of those names was Sailor Moon," Olivia then
noted.
"Well, that's the name of the show."
"I think Joss looks like her."
"Yah, IN HIS D R E A M S, but Sailor Venus looks like Sailor Moon. It's
part of her shtick."
"Joss, do you dream about being Sailor Moon?" Olivia inquired.
"No," Joss lied.
"But, yet, here you're dressed like her," Olivia retorted.
"No. I'm dressed like Sailor Venus," Joss corrected his subordinate.
"What is the distinction?" Olivia inquired.
"Sailor Moon is the Solider of Love and Justice, Sailor Venus is the
Soldier of Love and Beauty," Conrad added.
"You two take cartoons way too seriously," Olivia responded with a shake
of her head, amazed by the details of Conrad's response.
"It's not serious, but it's fun," Conrad retorted.
"Are you a big fan of it?" Olivia asked.
"Not of Sailor Moon. It's a little too teenage girl for me. That's
more Joss's speed."
"He's a teenage girl at heart," Olivia replied while they both shared a
laugh at her boss's expense.
"No doubt. You know the one about the five Sailor Soldiers that walk
into a bar?" Conrad responded.
"No," Olivia said.
"They're immediately escorted out for being underage like our little
girl here," Conrad teased.
Olivia shook her head before she asked, "Has this Sailor Soldier ever
showed up in uniform before?"
Conrad shook his head as he said, "No. He's never gone the whole Jimmy
Olsen route before."
"The what?" Olivia responded with a confused look.
"Jimmy Olsen from Superman! The Silver Age."
"Is that like the Bronze Age?" Olivia inquired.
"The Bronze Age of Comics came after," Conrad explained.
"Dork," Olivia said with a laugh as Conrad tried to change the subject
back to teasing Joss instead of him.
Joss shook his head at them as they continued to tease him. After the
15th comment from Olivia about his outfit that Conrad added to, Joss
said, "I'm so glad I introduced you two."
Conrad and Olivia shared a laugh over his words while they continued to
walk through the convention. As the evening grew near, Conrad asked
Olivia, "We're grabbing dinner, you want to join us?"
"Are you going like that?" Olivia asked as she pointed at his Flash
costume.
"No, we're stopping to get changed at Joss's place," Conrad replied with
blushing cheeks that nearly matched the hue of his costume.
"Yah, if it's okay with Joss, I'm happy to tag along," Olivia said.
"It's fine with me," Joss replied, knowing that any other answer would
be offensive.
With that decision made, the three made their way to the streets where
Conrad hailed a cab. They each got in with Joss stuck in the middle of
Conrad and Olivia. As he had on the way to the convention, Joss
collected the long hair of his wig and brought it over his shoulders to
make sure that no one sat on it. Olivia smiled at his endeavor, while
Joss sucked his lips into his mouth, knowing that he was going to get in
both ears the entire ride.
The two that were sandwiching Joss did not let up on their teasing
before they got out in front of his building. As Joss reached into his
purse for money, Conrad said, "I've got it, ladies."
"Such a gentleman," Olivia said with a laugh as she locked arms with
Joss.
Once Conrad finished paying, Joss walked up the steps to the front door
and unlocked it. He let Conrad and Olivia into the building before they
went to the elevator and rode it up to his floor.
While Olivia knew the building that Joss lived in, she had never stepped
inside it before. The building was less impressive than she expected,
but she still found it nice.
As they entered Joss's place, Olivia looked around at the nicely
decorated place and said, "This place has a woman's touch."
Conrad broke out laughing before Joss blushed and said, "No. I did it
all myself."
Olivia shook her head as she replied, "This must have been the work of
an ex-girlfriend."
Joss decided to let her keep thinking that. Joss had never had a
girlfriend since he moved into the place. His vast of array of feminine
costumes he enjoyed cycling through each night were not accommodating to
the prospect of having a girlfriend spending much time in his apartment.
As Conrad went to change in Joss's bathroom, Joss went into his bedroom
and disrobed. He changed into a pair of pants and collared shirt before
he put on a pair of shoes.
Once Conrad was out of the bathroom, Joss used his makeup remover to
take care of his face before he walked back over to Olivia.
Olivia grinned as she saw the telltale makeup traces on his face. She
decided not to say anything about them before they headed towards Joss's
front door.
As they exited, Olivia paused before turning to ask her boss, "Aren't
you going to take your bag?"
Conrad laughed before Joss retorted, "No. I've got pockets this time."
"Lucky, girl," Olivia teased before they went out the door to walk to a
local restaurant together.
They were seated shortly after arriving and talked while they ate. Joss
noticed the strange the looks the waitress shot him as she looked him
over while he ordered. Olivia grinned at them, knowing that the
waitress saw the same things on his face she did.
Once the meal was over, Conrad said goodbye to the two of them before
Olivia asked, "Joss, can I get your shoes?"
"Why?" Joss asked he looked down at his feet.
"No. Your little kitten heels."
"Why do you want them?" Joss asked as he started down the street towards
his apartment.
"To make sure I get you the right size," Olivia answered.
Joss shrugged before he agreed to lend them to her. After they got back
up to Joss's office, he handed the shoes to her. As Olivia took them,
she asked, "Do you really want them back?"
"Of course," Joss responded without thinking.
"Why?" Olivia inquired with raised eyebrows.
"I want to give them to charity."
"These are costume shoes. No real girl is going to wear these out,"
Olivia countered.
"They might," Joss replied.
Olivia responded with a shake of her head before she said, "I'll give
them back to you on Monday."
"Thanks," Joss responded with a small smile before he saw her out.
-----------------------------------------------------------------------
On Monday morning, Joss walked into work dressed as he normally was each
workday. Olivia grinned while she entered the office not long after him
before she inquired, "You remember our bet, right?"
"Clear it with the girls," Joss responded with a dismissive wave, half-
expecting the girls to want no part of the bet.
Olivia nodded as she turned and went over to A.J. and Tanya and told
them about the bet. The girls laughed as Olivia explained what Joss had
agreed to do that day and how his time in heels would be extended with
punishments to make the challenge harder each day he fell.
Joss could hear their snickering from beyond his door. Sensing that
they were going to hold him to the bet, Joss got to his feet and walked
out to see the girls.
The amused looks on their faces made Joss come to a conclusion as he
said, "She showed you the pictures from Saturday, didn't she?"
"What pictures?" Tanya asked as Joss's stomach sank.
"Of his costume," Olivia answered.
"THERE WAS A COSTUME?" Tanya inquired with evident excitement.
Olivia gave her a nod before she responded, "I wasn't planning to show
you, but since Joss was nice enough to let that cat out of the bag."
Joss blushed as Olivia showed the rest of his employees the picture of
him dressed as Sailor Venus. The girls burst into laughing before A.J.
asked, "Are you supposed to be a School Girl?"
"It's not a school girl outfit!"
"It looks like a Japanese one," A.J. countered.
"Well, Sailor Venus is Japanese," Joss responded with a shrug.
The girls broke out into further laughter as Olivia pointed to the
orange kitten heels he had worn before she explained their central
relationship to the genesis of the bet. Tanya wiped a tear away from
her eye as she exclaimed, "I'm so sorry I didn't go with you!"
"Olivia's presence was more than enough," Joss responded.
The girls laughed again before Olivia asked, "So, we're all onboard with
the bet?"
"Is he going to wear the sailor girl suit if we get onboard?" Tanya
inquired.
Joss responded with a shake of his head as he struggled not to blush.
Olivia said, 'Well, if he falls enough, just maybe."
The girls laughed before they agreed to accept the bet as they had
nothing to lose by it and wanted to see Joss struggle to comply with his
dress code. Joss was somewhat surprised that they were fine with him
wearing high heels around the office.
'Something to keep in the back of my head,' Joss thought before he saw
Olivia produce a pair of heels from her oversized pocketbook.
"What do you think of these?" Olivia asked while she held the three inch
heeled, stiletto pumps up in the air.
"Those are cute," A.J. answered for Joss as they all looked over the
black suede pumps with a pointy toe and low vamp.
"Are you ready?" Olivia asked as her eyes veered to her boss.
Joss nodded as he sat on the edge of the desk and took off each of his
oxfords. He went to put his socked foot into the right pump and noticed
that it was a little tight.
"It doesn't fit," Joss said with a shrug as he began to remove the pump.
"Take off your socks, O.J. They're not meant to be worn with something
so thick," Olivia responded to Joss's struggles that were causing the
girls to snicker.
Joss complied with her request and removed one sock. As he slipped his
foot back into the heel, the girls start to laugh anew at the image of
Joss's heeled shoes beneath his pants legs. He was surprised by how
well the shoe fit his right foot before he did the same with his left
foot.
Joss pushed himself off the edge of the desk and said, "Now, it's on,
girls."
"Bring it," A.J. replied with a smile prompting Joss and the girls to
laugh.
"Strut your stuff, girlfriend," Tanya added with a snap of her fingers.
Joss decided to be a little playful and tried to imitate a model's strut
on the catwalk. As he took the third step, his eyes widened as his
right ankle turned and he fell towards a filing cabinet. Joss's heart
raced as he braced himself against it.
"That's another day, right there," Olivia exclaimed with a laugh.
"Wow, he didn't even make it a minute into it," Tanya added while all
the girls laughed.
Joss pushed himself up as he realized that the bet may not have been as
easy as he thought it would be. The girls noticed the concern on his
face before A.J. asked, "Are you okay?"
"I'm fine," Joss answered with a racing heart before he started to walk
into his office, with one hand on the top of the row of the filing
cabinets as he did so.
"Remember you have to walk in those the rest of the day," Olivia
reminded him, while Joss continued to use the filing cabinets for
balance.
"Why? I'm already back in them tomorrow?" Joss retorted as he came to a
stop in front of his door.
"To give you the full picture."
Joss shook his head before Olivia reminded him, "You were the one who
was so sure that you could do this. And I'm wearing the same pair."
Joss looked at her shoes that looked identical to the ones he was
wearing. She took one off and showed it to him. Joss took it and
looked over the shoe before he handed it back to her.
Joss hung his head for a moment before he nodded, acknowledging that she
was right. As he made his way into his office, Joss stumbled again.
"What the hell?" Joss thought as he caught himself, reminding himself,
'It's heel, toe. Just like at home.'
Joss could not understand what was wrong as he got behind his desk. He
slipped a shoe off and looked at it. Nothing seemed terribly off about
it. The heel was a little narrower than most he wore, but it was no
more so than the heels of the boots he wore with his Catwoman outfit.
Slipping the other shoe off, Joss got to work. As he worked at his
desk, his mind kept drifting to why he kept falling throughout the rest
of the day whenever he walked around in his heels.
While he ate his lunch, he had a sudden epiphany. He understood what
was different from the conditions at home. While his office was
entirely carpeted, save for the vinyl, wood like flooring of the
kitchenette and the tile in the bathroom, the flooring of his apartment
was only wood or ceramic.
As Joss threw away the bag he brought his lunch in, he was certain that
the difference flooring had to be the reason he was falling. He had no
practice of walking on carpet. The more he thought about it, the more
obvious it was to him that his heels must be getting caught in the
fibers of the carpet.
'No wonder the girls complain,' Joss thought, deciding to eliminate the
shoe requirement from his office dress code.
Joss decided, however, that he was not going to do that until he made it
through a single day in heels without falling. If the girls did it for
years, he figured that he could do it for a day. While he had his
doubts, he felt that he could not give the girls the satisfaction of
welshing on a bet after one day.
Once the workday ended, Joss was relieved to trade in his heels for his
oxfords. The look of relief was undeniable to his subordinates and
brought renewed laughter from them.
"So, what's his punishment going to be?" A.J. asked Olivia.
Olivia nodded as she said, "I picked out the heels. I'll let you girls
pick out the next item."
"It's got to be nylons," Tanya responded.
"Nylons?" Joss asked with raised eyebrows.
"Not like the one's you seemed to be wearing on Saturday. You don't
need those with pants. I'm just talking about ankle nylons," Tanya said
with a nod.
"That would make it more real for this time of year," A.J. added with a
nod.
"Then, it's settled. Who's going to pick him up a pair?" Olivia
inquired.
"This one's on me," Tanya answered.
With the decision made, Joss and the girls said goodbye to one another.
Joss went home feeling as if he might have taken on more than he could
handle. Still, he was certain that he would make it through the next
day.
-----------------------------------------------------------------------
The following day, Joss walked into the office and saw the pair of ankle
length, black sheer nylons sitting on Tanya's desk next to his heels.
Joss gave her a smirk as he asked, "Shall I take it that those are for
me?"
Tanya responded with a smile and a nod before Joss took hold of them.
He sat down in A.J.'s chair and sighed as he removed his socks and
shoes.
'So transparent,' Tanya thought before she watched him roll down the
nylons without prompting.
Tanya watched as he put them on. Joss's expression did not change at
all. Joss felt that the nylons were little different from the thin
socks he wore during the summertime. They did not have much of a
different feel to them as wiggled his toes in them.
After taking the heels from Tanya's hands, the girls congregated to
watch him get of the chair in heels. Joss pushed himself up on the
arms, nearly stumbling in the process.
'Easy,' Joss thought while he righted his body.
Joss took a step, careful to land more on the balls of his feet rather
the heel. He felt that doing would be the trick to get through the day.
Joss took another step and felt the increasing pressure on his toes with
each unnatural step he took. The girls watched him grimace before
Olivia inquired, "Are you okay?"
"I'm fine," Joss lied as he pivoted on his heels before he felt his left
foot go out from under him. Joss's rear smashed into the carpet as the
girls began to laugh at the shocked look on his face.
"Oh, now, I know you just want to keep this going," Tanya exclaimed, as
she collected herself first amongst the girls.
"What?" Joss inquired.
"There's no way you fell both days within a minute. You just want us to
come up with something else for you to wear," Tanya teased.
"That's not it," Joss protested in truth.
"She's right," A.J. added.
"I don't want to keep doing this."
"Well, we know what you do on the weekend," Tanya countered with her
palms raised up towards the ceiling.
"That was a secret Cosplay," Joss lied while he struggled to get to his
feet.
After the girls made him explain himself, Joss added, "So, it wasn't
like I wanted to dress up like Sailor Venus."
"But, yet, you still did," Tanya rejoined as she shrugged her shoulders
from side to side.
Joss blushed before he put his weight back on the balls of his feet and
made his way into his office. Joss worked the rest of the day and
continued to struggle to keep off his heels while he walked.
As the workday ended, Joss inquired, "So, what's tomorrow's add on?"
Olivia smiled as she looked to A.J. and said, "It's your turn."
"My turn?"
"Me and Tanya already picked one thing out of him," Olivia explained.
A.J. nodded before she said, "I want to think about it."
"So, you're going to surprise me?" Joss asked.
"Sounds like fun to me," Olivia interjected.
"Keeping me on pins and needles, I see how it is," Joss said as he
finished tying his shoes back on.
"I'll make it a good one," A.J. countered.
The girls laughed as Joss squirmed and said, "I'm sure you will."
Shortly thereafter, Joss and the girls left for the day. Joss went home
and thought about what the girl was going to get for him. He hoped that
it would not be over the top, but A.J. was the quietest of his
employees. From his experience, it was the quiet ones that he had to
watch out for.
After returning to work the following morning, Joss noticed that he was
the first one to arrive. Joss unlocked the door and went into his
office to await the girls.
As Joss worked, Olivia and Tanya said good morning to him before A.J.
walked into the office. Joss could tell that A.J.'s decision to enter
the office last was deliberate.
She wanted to make an entrance as she unveiled the item she had chosen
to make his tasks his harder. From the laughter of the girls he knew
that she had certainly lived up to his fears.
Joss got to his feet and walked out of his office to see what she had
selected for him. His face fell as she held the pink satin skirt up to
his waist and said, "I'll think it'll fit."
"Isn't this too much?" Joss half-pleaded, hoping for a reprieve.
The girls responded in unison with a shake of their heads. Joss hung
his for a moment. Given the picture of him from the weekend, none of
the girls believed his disappointment for a second.
Joss took the skirt and walked into his office. He felt a little out of
his realm as he took off his pants and pulled the knee length pencil
skirt up his legs. Given the recent shaving over the weekend, they were
not very hairy, however, some stubble was visible. Joss cringed at the
sight. It was not something he was used to seeing paired with a skirt.
Normally, he shaved his legs or concealed them beneath opaque tights,
latex or a long skirt when he was en femme.
Knowing that he could not do anything about it, Joss sighed and reached
for his skirt. After adjusting the pink and black striped elastic
waistband of the skirt, Joss went to open the door. He felt the tight
restriction on his legs as he moved towards the door before he drew it
open.
Joss blushed while they laughed and clapped their hands at the sight of
their boss wearing a skirt above his black socks. The girls made a few
jokes before Olivia handed him the heels and the pair of nylon socks.
Joss shook his head at the socks and said, "These aren't what I wore
yesterday."
"You need some variety," A.J. countered.
"But they're not the same."
"They're close. They're still nylon ankle socks."
"These look like little girls socks," Joss responded as he touched the
ruffled, white lace trim of the nylon ankle socks.
"But they're made for a big girl," Olivia rejoined.
Joss winced at the idea of wearing them. They were not unlike things he
saw on girls at the cosplay conventions.
Relenting, Joss reached for the socks. He pulled off his black socks
and worked his feet into the girls' socks. The girls laughed at the
sight of Joss's ankles in the socks before the heels followed onto his
feet.
"I hope you girls enjoy this because this is the last day," Joss said as
he stood up and put his hands on his hips.
"How long until you pratfall this time?" A.J. asked.
"I'm not pratfalling," Joss retorted as he focused his gaze on his
shoes.
He knew that the tight pull of the hem added a new level to the
challenge, but it was something he had dealt with at home without issue.
Joss took a few steps before Olivia turned to the girls to say, "You
know he's going to fall because he knows I get to pick the next item."
"And what's that going to be?" Joss asked as he braced himself on the
doorway of his office.
"You're going to have to shave your legs each day you stay in that
skirt."
"How does that make it harder?" Joss inquired.
"It'll make it more real. Besides, who wants to look at stubble beneath
a skirt," Olivia countered with a shake of her head.
"Is that part of the bet?" Joss inquired.
"Is there any reason you want to make it harder?" Olivia rejoined.
Joss sucked his lips into his mouth while his employees laughed. Joss
shook his head before Olivia joked, "And you don't even have to buy a
razor, we already know you've got a Venus."
"Thanks," Joss replied with sarcasm while he gingerly made his way
towards his desk.
Joss was relieved to have made it. As he sat down, Tanya peered inside
his office and said, "You made it!"
Joss nodded as he held his arms up in triumph and tried to get to work.
Tanya called over to the girls, "It looks like Olivia finally found the
motivation to make him stop tripping himself."
"I wasn't tripping myself," Joss groused, angered by the continued
insinuation that he was deliberately forcing more feminine clothing and
accessories onto himself.
"I'm so sure," Tanya replied with a laugh.
Joss kept his walking to a minimum. The girls noticed that he was using
them to get his coffee more than had ever done so before. A.J. and
Tanya thought that he might be trying to ensure that he did not spend
another day in heels. Still, they whispered to each other that it might
all be a setup to make his next stumble appear legitimate.
As Joss stumbled on his hasty walk to the bathroom after a long phone
call, they knew they were right. The girls shook their heads at one
another before Olivia called out, "Good, I was sick of seeing the little
sprouts of hair on those legs."
"It doesn't go with a skirt," Tanya seconded while Joss stared at the
ceiling, dumbfounded that he had doomed himself to skirts in the office
for another day.
'When will the novelty wear off?' Joss wondered as he got up and
struggled to get to the bathroom.
He hoped that the girls would let him out of the bet soon since he was
concerned that he would never be able to walk on the office carpet. He
was sure that there was something defective about the slightly worn
carpet. Still, he wondered how the girls were seemingly able to
navigate it with ease, despite their complaints about his policy.
After Joss finished in the bathroom, he stumbled on his way back to the
office. Tanya shook her head with a smile at him as she said, "Now,
you're just playing it for laughs."
"I'm really not," Joss retorted, upset about his inability to walk on
the carpet.
Joss walked back into his office and only got up again to get lunch. As
he worked throughout the afternoon, Joss examined the carpeting around
his desk. He bent down and touched, trying to take in every detail to
it that he could.
Once the workday came to an end, Joss changed back into his pants, socks
and shoes and headed to the store. He was determined to make sure that
the next day was his last in his heels. He bought a cheap area rug that
seemed to have a similar consistency as the rug at his office and
brought it to his apartment.
After stepping into the shower and shaving his legs as he had on many
occasions prior, Joss walked into his bedroom to get dressed to practice
walking on carpet. He opened up the second closet of his bedroom that
he used to store his costumes. He looked in his closet for the skirt or
dress with the most similar hem to the one he was going to be stuck
wearing at work until he proved that he could make it a day in heels
without stumbling.
Joss settled on the tight skirt of his Agent Carter costume before he
went to put on a pair of nylons to recreate how his feet would feel.
While he did not have a pair of ankle socks, he figured that a pair of
black sheer pantyhose was similar enough to work.
With that decision made, Joss rolled the pantyhose down before he
brought them up his legs. While he had little excitement from the nylon
socks he wore at work, Joss loved the feeling of the nylon that was
covering his smooth legs. Joss wiggled his toes in his pantyhose before
he stood up and shimmed from side to side to get the pantyhose over his
hips.
Once it was in place, Joss reached for the pencil skirt of his costume.
Joss fastened the rear zipper of the skirt before he walked back to his
closet to look for his shoes. Joss felt that the pair of black heels he
wore with his Zatanna costume was close enough to give him a similar
experience.
Joss slipped his feet into each of the heels, balancing himself against
the door of the closet before he did so. Joss strolled into his kitchen
and ate a quick meal of the leftover chicken he had from the night prior
before he walked into his living room and looked at the cheap area rug
he bought.
Joss felt that the area rug was the cheapest looking thing that ever
touched his floors. He unrolled the rug and started to walk across it.
Joss paced back and forth, hearing his heels click on the wood floor
every time he made it across it without incident. Joss's mind raced as
he continued to walk across the area carpet without stumbling. There
was no uneasiness to any of his steps. He even landed his heels easily
towards the edges of the rug that were curling up.
Joss shook his head. He could not understand what was wrong.
'Is the carpet that bad?' Joss speculated. The more he thought about,
the less likely it seemed that it was the carpet that was at issue.
Sitting down on the couch, he clutched the sides of his head as he
wondered aloud, "Maybe, it's all in my head."
-----------------------------------------------------------------------
The following morning, Joss returned to work. After he said hello to
the girls, he walked into his office and saw the skirt, socks and heels
waiting for him on his chair.
"Just great," Joss mumbled before he closed the door and changed into
them.
Joss decided to avoid walking as much as he could. He worked at his
desk for the remainder of the morning, refusing the girls inquires about
if he wanted coffee. His refusal prompted questions about his health,
but he dismissed them.
Joss was determined to avoid needing to go to the bathroom to prevent
any unnecessary walking. He knew that avoiding coffee was the first
step to achieving that.
After having lunch brought to him under the guise of having an excessive
workload, Joss felt a headache coming on. He felt a bit disoriented as
he asked the girls to get him a cup of coffee to try to get rid of the
headache.
Shortly after he finished the cup, Joss felt the urge to go. He fought
it as he crossed his legs and bit his lip.
Once he could not take it anymore, Joss slipped his feet into his heels
and rushed to the door. He did not make it two steps before he tripped
forward and landed on his palms.
"Fuck," he screamed.
"Are you okay?" Olivia asked as she rushed towards him.
"No. I can't do this," Joss shouted as he took off his shoes. He
tossed them against the wall before he rushed into the bathroom.
The girls gave each other nervous looks while he relieved himself. As
Joss went, he felt bad about yelling over his failings. He cringed as
he was growing more certain that it was all in his head. He was choking
under the pressure and, now, he knew that he had cracked under it.
"You can't quit," Joss thought while he closed his eyes. He propped
himself against the wall with an outstretched arm while he continued to
go. He wanted to quit, but it was not in his nature to quit. He always
pushed himself to excel at everything, and he eventually became
serviceable at everything he ever put his mind to accomplishing. He was
sure that he could make it through one day in heels if he took a
measured approach.
Joss was happy to finish washing his hands and get his feet off the cold
tile flooring. The carpet, however, felt rough beneath his thin socks
while he walked on it. He almost wanted to put the heels back on.
As Joss came around the corner from the bathroom, the girls gave him
inquisitive looks as they tried to see if he was okay. Joss closed his
eyes before he apologized about yelling. As A.J. was about to ask if he
wanted to be let out of the bet, he inquired, "So, what do I have to do
tomorrow?"
A.J. gave the girls an expectant look; however, it was not her turn to
pick the item. Tanya answered, "I'm going with a pair of pantyhose."
"Really?" A.J. asked.
"He's already got the shaved legs," Tanya replied as Joss rubbed his
head. Although he enjoyed wearing them, he was concerned about showing
that to the girls by accident.
A.J. nodded before she said, "I think that's a good choice."
"Then, it's settled," Olivia said with a clap of her hands before her
eyes trained on her boss.
"Hurrah," Joss said, unable to hide his sarcasm.
'Like you don't love it,' Olivia thought with a shake of her head and a
smirk.
Joss retreated to his office with careful steps. He walked behind his
desk and slipped off his shoes. He picked them up again and gave them
another cursory inspection.
"What the fuck is wrong with me?" Joss said, after seeing nothing
glaring unusual about the shoes. The grooved, rubber under sole was not
like his normal heels, but it was reminiscent of what was on his
oxfords. It was also identical to what he remembered seeing on the
bottom of Olivia's shoes when she wore a matching pair.
Joss tossed the shoes under his desk in frustration as he clasped at the
sides of his hair. He shook his head, surer than ever that he was
chocking under pressure.
The next day, Joss found an unopened package of white cream-colored
pantyhose waiting for him with the rest of his outfit. With none of the
girls around, he did not bother to wipe the smile from his face while he
closed his office door. After opening the package and stepping out of
his pants, Joss rolled the pantyhose down and brought the control top
over his briefs. The silky feelings surrounding his legs kept the smile
on his face while his manhood swelled.
Joss hoped that the girls would be unable to tell. Figuring that it
might show in the tight skirt, Joss groaned before he reached between
his legs and tucked his manhood between his legs.
"Just terrific," Joss said while he saw looked at his smoothened front,
knowing that he was going to be sitting on his member the entire day.
"This should make for a comfortable day," Joss muttered before he
covered his legs with the skirt and put on the shoes.
After dressing in it, Joss drew the door open.
The girls soon swarmed on his office to see Joss model his new
pantyhose. The girls shook their heads at how shapely his thin legs
looked in person in them.
As they walked out of the room, A.J. whispered to Olivia and Tanya, "I
can't believe he didn't tear them."
"Why would he?" Olivia asked.
"Any girl who doesn't know what she's doing would tear them," she
countered.
"She's a skilled girl in there," Olivia replied with a shrug.
"I knew it," A.J. said in a forceful whisper with a smirk.
Tanya nodded along, as they all knew that they had the final
confirmation that his secret cosplay excuse was just that. They figured
that he had spent many days in pantyhose before.
"What else do you think we can get him to wear?" A.J. asked, as any
sympathy she had for Joss was drained from her. The lack of runs in his
pantyhose had reconfirmed her earlier suspicions that each fall was on
purpose.
"You're up next, you tell us," Olivia countered.
"He's wearing a bra on Monday."
"Interesting choice," Tanya said with a slight laugh.
"He's going to like it," A.J. said with a nod of her head to the other
girls' amusement.
As the girls talked, Joss stole glances at his legs. He enjoyed the
feeling and loved the way they looked on him. He worked at his desk for
most of the morning before he got up and stumbled into the credenza that
was next to his desk.
"Did you fall?" Olivia asked as she got to her feet.
"I...uh...yes," Joss admitted before Olivia came over to his office.
"I'm putting you in a bra on Monday for that one," A.J. called in.
"Looking forward to it," Joss replied with a shake of his head and
blushing cheeks.
-----------------------------------------------------------------------
After leaving work on Friday, Joss could not stop thinking about what
was awaiting him on Monday. He knew it had to stop, but he was getting
turned on by the idea of openly wearing pantyhose around the office.
While he had occasionally worn them beneath his pants, this was a
different sort of high.
"You can't let that influence you," Joss reminded himself as he drove to
the office on Saturday, while rubbing his pantyhose through his pants
legs. He was hoping to get his feet into the heels to practice over the
weekend.
Once he got to the office, however, he noticed that the girls had not
left his outfit out in the open. There was not a trace of it anywhere
as he searched every inch of his office suite.
"You got to be kidding me," Joss whined to himself as he looked around
the office, realizing that one of the girls had to have taken the outfit
home with them for the weekend.
He kicked at the carpet with his shoes before he walked out of the
office to go food shopping. It was a place that Joss often wore
pantyhose to beneath his clothing. He enjoyed the thrill of it and the
risk of exposure to someone he knew was minimal.
As he made his way through the store, Joss felt one of his bra straps
slipping down his arm beneath his boxy sweater. Joss grimaced as he
looked around the store and muttered, "Crap."
Once he was sure that no one was looking, Joss shimmed his shoulders as
he adjusted the strap through his sweater before he went back to
shopping. Joss then continued through the store and made his way to the
cashier.
The familiar looking cashier gave him a smile and wished him a good day.
It was nothing more than he normally experienced with her before he went
to his car and put away his groceries.
He drove them to his apartment building before he parked in the
underground garage and made his way to the elevator. A woman he
recognized, but never exchanged more than pleasantries exited. She gave
him a knowing smile while she walked passed him.
"I got to talk to her one day," Joss said to himself while he road the
elevator up before he realized that the large collection of feminine
costumes in his bedroom precluded any probability of a serious
relationship.
After going out with some friends on Saturday night, Joss's focus
returned to the week ahead on Sunday. He fantasized about what would
happen and how far it would go. He knew that it could go off the rails
at anytime, but that was what made it so alluring now that he was
finally going to be wearing what he enjoyed.
As Monday came, Joss returned to the office. He tried to hide his
excitement as he walked into his office suite.
Nearing his office door, Joss saw the padded white bra hanging from the
door handle. Joss gave A.J. a glance and a shake of her head.
"Is that the chick version of a tie on the doorknob?" Joss inquired with
a grin.
"No. It's the chick sign for you need to put on a bra!" A.J. answered.
"Yah, you can't just let them keep flapping around," Tanya added with a
laugh.
"Let what flap around?" Joss asked as he clasped his flat chest, playing
along with his employees' teasing.
"Your girls," Tanya said.
"They must have never budded," Joss countered before he took hold of the
bra and walked into his office.
Joss closed the door behind him. Joss locked the door and tossed the
bra on a chair. After he removed his clothes, Joss brought the
pantyhose back up his legs. Joss savored the feeling of the soft nylon
ascending his legs while he listened to voicemails.
After getting the pantyhose up to his hips, Joss reached for the skirt
and stepped into it. He then reached for the bra. He hooked it before
he brought it down over his head and took hold of his shirt.
As Joss finished buttoning up his shirt over his bra, he looked down and
thought, 'I might be able to get away with this going forward.'
While Joss often had worn bras out under his tops, he never did it at
work because he thought his business shirts were too thin to conceal the
bra. Now, his whole opinion had changed as he could not even recognize
the straps beneath his shirt while he looked down at himself.
Stepping out of his office with his weight on the balls of his feet,
Joss asked A.J., "Can you even tell I'm wearing your bra?"
"Well, it's your bra, now. I don't want it back," A.J. answered with a
shake of her head.
"But you can't even see it?"
"Are you kidding?" Olivia asked as the girls laughed.
"What?"
"We can see the whole outline," A.J. responded.
"Honey, a girl can't miss those straps beneath anything," Tanya added.
"Really?" Joss asked, growing nervous that the cute girl who gave him a
look as he got off the elevator over the weekend had been really
smirking at his sagging bra straps. He wondered if the checkout girl
had noticed it as well.
'That makes me rethink things,' Joss thought with a shake of his head.
"Those straps are telltale. They can't be anything else," Olivia
seconded.
"Maybe I just have a back problem," Joss said.
"Because your breasts are so big?" Tanya inquired with a laugh.
"No. A guy could have a brace on."
"It wouldn't anything like that," Olivia responded as the girls seconded
her opinion.
"Oh," Joss said, fearing that he had unknowingly outed himself to many
women over the years when he went out wearing a bra under his tops.
With that fear preoccupying mind, he turned and landed his heel first.
Joss tumbled into the doorway, catching himself against the frame before
Olivia, "And now, you're wearing a blouse with that bra."
Joss clenched his eyes. He could not believe that he had let his guard
down. He banged once on his door while he replanted his feet beneath
him.
The girls shook their head, not believing his act. They were each sure
that he had done it intentionally again.
'Does he really think we're falling for this?' Tanya thought, while
A.J. had a similar sentiment in her mind.
Joss walked back into his office. He worked and fell twice more
throughout the day. He wanted to scream as he turned in his shoes for
the day, even though he was intrigued by how he would look in the full
feminine guise they had planned for him the next day. While he had
dressed like Manga and Comic Book Superheroines and Supervillainesses
since he was a teen, he had never dressed as a regular woman in full.
He wondered what kind of image he would cut in the outfit throughout the
rest of the day.
Knowing what he was going to be in full femme mode at work from the neck
down, Joss decided to play with the situation. While he had been able
to hide himself from the waist down from people looking through the
office's few blind less windows due to the location of the office
furniture, he knew that, depending on the look of the blouse, there was
going to be a good chance that people could see that he was a man
dressed as a woman from the neck down going forward.
Seeing no reason not to do it, Joss reached for one of his wigs. He
placed it in a shopping bag and went down to his car with it.
Joss carried it into his office after he pulled up in front of the
building. The girls inquired about what was in the bag as Joss walked
into the office. He told them it was a secret as he saw the three-
quarter sleeved, white blouse that was hanging with a bra off the knob
on his office door.
Joss placed the bag down in his office before he took hold of the bra
and blouse that was decorated with bejeweled buttons and closed the door
behind him. After stripping out of his clothes and shoes, Joss placed
on the bra and reached for his pantyhose.
Stepping into the pantyhose, Joss brought them up his legs, eager to
feel their embrace once again. He wiggled his toes in them as he
adjusted them to fix the bunching and even out creases.
Reaching for the skirt, Joss brought it up to his waist before he took
hold of the stretch cotton blouse. Joss slipped his arms through the
soft sleeves of the blouse before he buttoned it.
Joss glanced down and looked over his body. From the head down, it
appeared that he had breasts given the blouse's tight fit and the bras
slight padding.
Joss's member swelled as he processed what he was seeing. 'Shit,' Joss
thought, upset about his reaction that was little different from when he
dressed up as a character at home.
Trying to shake the thoughts away from his head, Joss walked towards his
door and took hold of his wig. He slipped it onto his head and decided
not to secure it in place for fear of giving himself away any further.
He thought about taking off the wig, but he decided he needed to wear it
to not draw any unwanted attention that his silhouette through the
window might attract otherwise without it.
The heels were the last thing he put on, knowing how much of a struggle
they had been for him. Joss slipped his feet into the shoes while he
braced himself on the door. His heels sunk into the carpet slightly
before he drew the door open to reveal himself to the girls.
The sound of Joss's opening door caused the girls' heads to snap towards
it. Joss braced himself for the girls' laughter. It came the instant
he opened the door and emerged en femme from his wigs to his heels.
Joss's voluntary wearing of the wig only further confirmed A.J.'s
conclusions that he had no intention of staying on his feet a whole day.
She shook her head at him before Tanya said, "You're looking sharp
today, Joss!"
"Feeling sharp," Joss replied as he placed his weight on his right leg
and pushed his hip out. The girls laughed at the S-curve stance that
Joss struck and shook their heads at it.
"Why are you wearing a wig?" Olivia asked as she ceased her laughter.
"It seemed appropriate under the circumstance."
"But I was going to make you wear one," Tanya replied.
"Well, I beat you to the punch."
"So, you're making it harder on yourself," A.J. interjected.
"I wouldn't say this makes it any harder," Joss countered in truth.
"But you're adding things now too," Olivia retorted with raised
eyebrows.
"Just this. I'm not adding anything else," Joss replied before he
explained his reasoning to the girls' uniformly incredulous stares.
After he finished his justification of his wig, Tanya noted, "Your wig
shifted a little while you were talking."
"It just sitting on my head," Joss replied as he adjusted it.
Olivia grinned as she said, "Let's see how far it moves. Think fast."
"What?" Joss replied before he jerked to catch the stress ball that
Olivia had tossed side arm at him.
As Joss sensed his body's knee jerk reaction to the movement of the
ball, he realized his mistake. Joss's right leg gave out. He landed on
his rear as his wig shifted on his head, causing more of the hair to
fall over his eyes. He gazed up at the laughing girls and shook his
head, unable to believe that he had fallen yet again.
As Joss pushed himself up, Joss wondered, 'Where else can this go?'
As Tanya walked over to him and helped him up with Olivia, she said with
a laugh, "What should I put on him now? He did the long hair on his
own."
Olivia shrugged as she said, "Your call."
"Please have mercy," Joss whined, half in jest.
The girls laughed before Tanya said, "Okay, I'll just go with a pair of
SPANX."
"Why?" Joss asked as the girl's laughed at the idea.
"Because I want one guy on Planet Earth to understand what it feels like
to wear them," Tanya countered.
"I'm down with that," A.J. chimed in as Olivia nodded along.
"Sounds like fun," Joss said with a shake of his head.
"It's not the end of the world!"
"Can I get out of these shoes? Please! I'm begging you!"
Olivia looked at Tanya and A.J.. The two shrugged before Tanya said,
"He's already in them tomorrow, so why not?"
Joss thanked the girls as he took the shoes off before he asked Olivia
to get him a cup of coffee. Olivia took the shoes from her boss and
started towards the kitchen.
Tanya followed her into the kitchen and said, "That was nice of you."
"Nice of us," Olivia replied.
"Well, I think the old girl can stand to have a few hours without doing
his whole I can't walk in heels thing."
O