Off to the Races
Belladonna
[Author's Note: Based on a suggestion by Renny Renne]
"You can't really think you'd make a better woman than me?"
"Oh, I know I can," Christian teased his assistant.
"You do know I'm a really girl, right? Just so we're clear," Marissa
retorted, bemused by the subject of the conversation she was having with
her boss.
"Men are always better at being women than women are."
"Do you think you're prettier than me?" Marissa asked, placing her hands
on her waist as she did so.
Christian laughed as he shook his head and replied, "Of course, not. Look
at us..."
"So, how could you..."
"There's a lot more to being a girl than being pretty."
"I'll give you that, but not according to men!"
"Ah...but according to this man..." Christian replied with his hands held out
to the side.
"Oh, that's charitable..." Marissa rejoined with a smirk.
Christian put his hands on his hips and stared down at Marissa in silence
before she continued, "Like a man would really be having this
conversation."
"I'm just stating facts! There's nothing manlier than that."
"There's nothing manlier than stating you'd make a better girl that a real
girl?" Marissa retorted, shaking her head at the absurdity of her boss's
words.
"Well, when you put it like that, you make it seem..."
"Queer," Marissa interjected. She grinned at her boss's peeved look before
she added, "You know, not in the gay sense, but in the strange sense."
Christian laughed before he responded, "Oh, of course. Thanks for clearing
that up!"
A faint smile came upon Marissa's face as she replied, "I think you would
make a convincing little lady."
The smile fell from Christian's face while he processed his subordinate's
words. He cocked his head and asked, "Why's that?"
"Look at you. You're a little shortie with that long hair and cute button
nose..."
"And two eyes made out of coal."
"Not those baby blues," Marissa countered before continuing, "I bet you get
confused for a girl all the time."
Christian rolled his eyes before she Marissa added, "At least from behind."
"There is no way that I could ever be confused with a girl," Christian
countered.
Marissa laughed at the certainty conveyed by her boss's tone. Christian
glared at her in response before she asked, "Is there a way we could prove
that?"
"I don't see how?" Christian replied, placing his hands back on his hips.
"Unless...we get you in the right dress," Marissa responded with a laugh.
"Like that would ever happen," Christian said with a shake of his head.
"Oh, so, you don't think you could do it?"
"No..."
"Really, says the man who thinks he makes a better girl than me," Marissa
teased.
"What do you want me to do?" Christian asked with evident exasperation.
"I don't know..."
"You can't possibly think I'm going to put on a dress and..."
"I didn't say that."
"You just did!"
"I was just joking."
Christian smiled at her as he double downed, "I know, because you know I'd
make a better girl.
"Oh, really?"
"Yup," Christian answered with a grin.
"Well, in that case, why don't you prove it?"
"I would if I could."
"Oh, but you can."
"How could I do that?"
"By putting on that dress you keep talking about."
"You were talking about it," Christian countered.
"Whatever," Marissa replied before she added, "I think you could make a
passable girl."
"Now, that's crazy," Christian replied with a laugh.
"No. I'm sure of it. You got potential," Marissa responded, drawing out
the last word in the process.
"And what are you going to do with it?" Christian inquired.
Marissa grinned as she got to her feet. She stood up and stepped towards
Christian. Christian stared up to meet her green eyes.
Marissa clasped his long blonde ponytail and pulled it from behind his head
to rest it on his shoulder. She smiled as she said, "I could do a lot with
that, Blondie."
Christian squirmed at her words before he inquired, "Like what?"
"I could tease it up. Make it look real pretty, just like your pretty blue
eyes."
"Jealous?" Christian joked.
"Like a green eyed monster," Marissa replied with a laugh as she tilted her
head.
"It takes more than hair to make a girl," Christian responded.
"No doubt, but with your soft features, you could definitely pull it off."
"Are you calling me dainty?" Christian countered.
Marissa laughed while she answered, "I never said that."
"You certainly implied..."
"You started this conversation," Marissa countered.
Christian nodded in admission before he said, "It doesn't seem like a
fruitful area of discussion."
"I suppose," Marissa replied as she gripped his ponytail and pushed it back
to its familiar place behind his head.
Christian shook his head at her and added, "It's not like there would be a
way to prove it."
"Prove what?" Marissa asked.
"Nothing," Christian replied, turning away from her as he said the single
word response.
"That you'd make the better girl? No, that's a matter of opinion."
"I think I'd be the consensus choice," Christian replied, stopping and
turning to look at his assistant as he did so.
"Why don't you man up and prove you could even be considered a girl?"
Marissa replied, feeling challenged by her boss's declarations.
"And how would I do that?"
"Let me take a crack at you."
"Oh, you'd just love that."
"I do like a challenge."
"But how would it prove anything."'
"We need to get an impartial judge."
"I wouldn't want anybody to know that I'm a guy in drag."
"We wouldn't tell them."
"Then, how would they know?"
"So, you agree with me."
"Huh?"
"I told you could make a convincing girl."
"Oh, come on."
"You said, how would they know?"
"Are you talking about showing me off to strangers?" Christian inquired
with a tilt of his head.
"Seems like it could be a lot of fun," Marissa replied with wide eyes and a
smile.
"It sounds dangerous!"
"The bar by my house does a whole Derby Day celebration each year. There's
tons of people. The men are all betting and drinking and most of the girls
just drink and focus on the hats. Nobody's going to be focusing on you,"
Marissa replied, trying to jokingly reassure her boss.
"I don't know about that..."
"Oh, so, you're not so confident, now?" Marissa retorted with a laugh.
"I was never confident about looking like a girl."
"But you, somehow, think you make a better one than me?"
"I meant mentally."
"There's more to being a woman than what's up here," Marissa replied as she
tapped her temple.
"Isn't that the complete opposite of what every woman says?" Christian
rejoined.
Marissa paused before she nodded with a grin while she answered, "Most men
don't challenge us this way though."
"What's in it for me?"
"The satisfaction of proving you can make a woman, let alone one better
than me."
"Doesn't seem like something I really want."
"Then, why did you bring it up?" Marisa countered.
Her words were met by a shrug of Christian's shoulders.
Marisa sucked her lips into her mouth for a moment before she said, "Okay.
Okay. All right, how about if you are not recognized as a man, you have to
spend a month as my secretary."
"What?" Christian bellowed before letting out a nervous laugh.
"Oh, and in my heels too!"
"I still don't see what's in it for me? That seems to be all for you,"
Christian retorted, blushing at his assistant's words.
"I don't know. What do you want from me?"
Christian stared blankly at her. Marissa laughed before she added, "And
keep the request PG."
Christian blushed at her insinuation that he would ask for something
inappropriate. He knew well enough that she had no doubt that he would
never do so. Christian shrugged again before he said, "I can't think of
anything."
"Really? So, you're the man that has everything?"
"I have enough."
"How about a year of maid's service?"
"You're really going to clean my house?" Christian asked with a
disbelieving shake of his head.
"Oh, hell no, but I have a friend who runs a company. I'd pay her to do
yours and mine."
"That's nice, but it's still not enough to convince me..."
"Okay, how about a year of a maid's service, and I dress up as something
you think is embarrassing for a day."
"What?"
"You think you're risking being humiliated, humiliate me if I don't make
good on my promise."
"And how does a man go about humiliating a pretty, statuesque girl?"
"I'm not giving you any ideas! Surprise me," Marissa retorted.
Christian laughed before he asked, "Are you serious about this?"
Marissa gave him a nod before she inquired, "Are you?"
Christian gave her a blank stare before he answered her challenge, "I'll do
it."
"You will?"
"Called your bluff?" Christian retorted in response to his secretary's
surprised tone.
"No. I'm all in. It's a bet."
"It's a bet," Christian said, repeating her words, surprised that she did
not back down. Christian's mind raced while he turned and walked back into
his office to go back to working.
A few days passed before Marissa brought up the subject again. As he
entered the office, Marissa asked, "Are you ready for tomorrow?"
"For what?" Christian asked.
Marissa gave him a disbelieving look before she asked, "You didn't forget
our bet?"
"You're not really going to hold me to that?" Christian asked, squirming a
bit as he did so.
"Why not?"
"It's going to be humiliating when people realize..."
"No one's going to realize. Trust me."
"But, if they do..."
"You get tit for tat with me..."
"It's not the same."
"This isn't Cheers, Christian. We're going to a place where, literally, no
one knows your name."
"But they know you!"
"I'm not a regular, Christian. I only go there a handful of times a year."
"How can you be so sure that I can make a convincing girl?"
"The height is a help, short stuff."
"That's not near...ly...enough."
"The smallish feet and Donald Trump hands, your smallish nose, that soft
chin, those pretty, high cheekbones...Oh, damn it, girl! You could be
strutting down the catwalk in Louboutins right now if you were a few inches
taller," Marissa cracked.
"Oh, come on," Christian replied with blushing cheeks.
"Aren't you the least bit curious?" Marissa said.
Christian shrugged before he inquired, "Why are you?"
"I haven't done a girl's makeup since college. It was a lot of fun."
"Are you trying to relive something through me?"
"It could be fun," Marissa teased.
"You just want to tease me about getting me into a dress."
"That'll certainly be a lot of fun," Marissa admitted with a laugh.
"So, you just want to humiliate me. Let's be clear about this."
"I don't want to humiliate you. I've dealt with that too much."
"When were you ever humiliated?" Christian asked in disbelief as he gazed
up at his secretary.
"Christian, I'm 6' tall."
"That's a good thing. Me and the rest of my fellow vertically challenged
dwarfs would kill for that."
"It's nice. I'll give you that, but it attracts some looks."
"Again, most girls would like that..."
"I do, sometimes..." Marissa began to respond as she saw Christian crossing
his arms with a look of incredulity on his face about her statement.
"Okay, more times than not, but, when I was a kid, it wasn't good."
"What do you mean?"
"I was 5'6" by the time I was ten. I was the tallest kid every year until
I was in the 8th grade. Everyone used to tease me and call me a giraffe."
"Oh, come on...."
"I wasn't the most graceful girl either. I was kind of ungainly."
"Has that changed?" Christian joked.
Marissa gave him a glare before she added, "As I was saying, I know what
it's like to be humiliated."
"Try getting your head stuck in a toilet," Christian retorted.
"That happened to you?" Marissa asked with a furrowed brow.
"No, but it happened to somebody," Christian answered.
Marissa shook her head at his response before she said, "I'm just saying, I
wouldn't agree to something that would embarrass me that easily because if
you get embarrassed, I get embarrassed. That's the deal!"
"And exactly how would I embarrass you?"
"I really don't want to give you any ideas!"
Christian laughed at her before he said, "But what would everyone think if
you won?"
"Who?"
"The people in the building, the attendants..."
"You're asking how the garage attendants would feel. They never see you.
They never talk to you. I'm the only one of us who talks to any of them."
Christian nodded, aware that she was telling the truth. He knew that the
employees of his parking garages only dealt with Marissa. He did not like
having to bother with them. It was part of the reason that he hired
Marissa as he developed and leased more parking garages.
He knew that Marissa could do his job too. She had done it before when he
felt like off loading his work on her. It was a simple matter of making
sure that the amounts that came in added up with the monthly clients, which
was augmented by the non-regular users.
Payroll was limited to the handful of employees at each site. Paying
rents, mortgages, taxes and utilities were something that she already did
on his behalf as well.
"You're just stalling because you're scared," Marissa teased.
Christian shook his head as he said, "All right, I'll do it."
"You will?" Marissa replied, taken aback by his words.
"Sure, if only to make you suffer by making you wonder what I'm going to
have you wear on Monday after some closeted, jerk off clocks me in the
face."
"Won't happen," Marissa replied with a hint of certainty before she made
plans to meet with her boss at her apartment the next day.
-----------------------------------------------------------------------
The next afternoon, Christian knocked upon Marissa's door with a knot in
his stomach. While part of him was intrigued over how convincing a woman
she could make him, another part of him was sure that he would be entirely
unconvincing.
Marissa drew the door open. She smiled at her boss. She let him in and
said, "I've got everything ready for you."
"Okay."
"I put everything I want you to put on in the bathroom," Marissa responded,
her smile growing larger at the sound of the nervousness in her boss's
tone.
Christian nodded in silence as he followed her through the small apartment
and into her bathroom. Christian came to a stop as he saw the panties,
tights, bra and socks.
"What am I supposed to do with all that?"
"You're going to put it all on, and I'm going to hand you a dress."
"How am I supposed to do that?"
"Well, the panties are just like putting on briefs. Pick one leg up and
then the other," Marissa answered.
"Ha...ha..., but what about the rest?" Christian asked, surprised by his
secretary's expectation that he knew how to put on girls' undergarments.
Marissa grabbed the bra and said, "See this hook in the front. Just put
your arms through the snaps and hook it up. When you're done, shove in the
socks in the cups and, voil?, you've got big girl breasts, girlfriend."
"I don't think it's that easy, and what about the tights?"
"The tights aren't a big deal."
"Do I even need them?"
"It's too cool outside for bare legs. You'll freeze on the walk back."
"I guess," Christian replied as he picked up the tights and pulled at the
waist.
"Aren't these delicate?" Christian added, darting his eyes up to Marissa's
as he did so.
"They're the highest denier they make."
"What the hell does that mean?"
"They're the least delicate tights they make."
"But, they're still delicate!"
"Christian, I put some thought into this. It'll be alright."
Christian gave her an inquisitive look before he countered, "Well, if you
gave it some thought, I'm sold."
Marissa rolled her head in response to Christian's sarcasm before she
explained, "I froze them so they wouldn't tear as easily."
"You can freeze tights?"
"Yes. You wet them down and freeze them in a baggie. Once they thaw out,
the fibers get tighter and stronger. It makes them harder to tear."
"This seems like a lot of work."
"It takes a lot of work to be a girl, let alone one better than me,"
Marissa retorted.
Christian nodded before Marissa closed the door to let him get dressed
after telling him to roll the tights down before he stepped into them.
Christian locked the bathroom door before he removed his clothes.
He pulled his boxers off last before he stepped into the black, cotton
panties. A grin came upon his face as he felt the softness of the panties
as he brought them up his sparsely haired legs.
The sight of an erection his panties made Christian blush. Christian shook
his head as he thought, 'Why are you blushing? No one can see you!'
After he pushed his humiliated thoughts to the back of his mind, he reached
for the matching, plain black bra and worked his arms through the straps.
While locking the front clasps, Christian's eyes veered down to the white
socks that Marissa had left for him.
His fingers left the clasps to reach for the socks before he stuffed each
cup. Once he finished, Christian cupped his bra cups to check that each
stuffed cup was roughly the same size before he took hold of the tights.
Following Marissa's instructions, Christian began to roll the black tights
down before he placed his toes into them. He grinned at the soft feeling
encasing his feet before he unrolled the tights over his ankles and calves.
Another erection followed while he brought them up his legs and over his
hips before he reached for the doorknob.
His hand jerked away from the lock as he caught a glimpse of his noticeable
arousal from the feminine undergarments he was wearing. Christian shook
his head and muttered, "I can't let her see me like this."
Christian tried to think about other things to get his mind to focus on
matters that would not excite him. Marissa grew impatient as she waited
for Christian to finish dressing. She called to him, through the bathroom
door, "Are you okay in there?"
"Just finishing up," Christian replied in a near panic.
"Well, hurry up!"
"I'm trying," Christian muttered before he noticed that his erection had
largely subsided.
Christian let out a deep breath before he poked his head out the door to
call out to Marissa. Marissa smiled as she approached him with a white,
poplin dress in her hands.
Christian's eyes widened while he examined the dress's eyelet, pinwheel
detail, as well as the scalloped trim at its cuffs and hem. The grin on
Marissa's face grew as she asked, "It's so pretty, right?"
"Sure," Christian replied while he reached his arm out the door to clasp
the three-quarter sleeved dress.
Marissa laughed at the sight of the bra strap on her boss's exposed
shoulder while he took hold of the dress. Christian blushed at her
laughter while he closed the door behind him. Marissa walked away from the
door with her hands over her mouth, as she tried to muffle her laughter.
After locking the door again, Christian put his back to the door. "What
the hell are you doing?" He asked himself.
He gazed down at the dress. As he examined it, he realized that it was the
kind of dress he liked to see on a girl.
A smile came across his face while he brought the dress over his head. He
pulled the cotton dress down over his body and stared down at the bust
line.
Christian was relieved that the dress's v-neck ceased its plunge above
where his bust should be. Noticing the fit and flare silhouette of the
dress, Christian spun in place for a moment, enjoying the feeling of his
nylon covered soles moving on the tiled floor as he did so.
Christian smiled at his reaction, feeling that the dress's silhouette gave
him a more feminine appearance as he reached for the rear zipper. He
arched his back as he struggled to zip up the dress. A few fruitless
attempts to finish bringing it up his back caused Christian to give up. He
drew the bathroom door open before he called out, "Marissa, can you come in
here?"
Not seeing or hearing her, he stepped out of the bathroom. Christian
sensed the feeling soft rug of her hallway while he approached her living
room. It felt much better to him than the cold ceramic tile that had been
beneath his tights covered feet earlier that day.
Hearing him approach, Marissa got up off the couch and grinned at his
appearance as she gazed down at him. She shook her head as she said, "You
don't think that body can pass itself off for a girls?"
"It's not my body I'm worried about," Christian replied honestly before he
asked for her help with the zipper.
"No problem," Marissa replied as she stepped behind him. Christian could
feel her towering over him. He twisted his head and took in the blue and
white, halter-top dress that she had put on while he was getting dressed.
He felt every inch of Marissa's 6 inch height advantage as she reached for
the zipper of his dress. She then asked, "Can you get your hair out of the
way?"
Christian clasped his ponytail and brought it over his shoulder. Marissa
patted his side as she said, "Thank you."
"No problem," Christian replied, flustered by being turned on by her too
familiar touch.
Marissa brought the zipper up his back and took a step away from him. With
the dress secured over his body, Marissa told Christian to follow her into
her bathroom. Christian followed behind her, struggling to keep his eyes
away from her swaying rear, before she sat him down on the toilet lid to
style his hair. Marissa reached for the curler that she had left warming
for him.
"What are you planning on doing?"
"I'm just going to give your flat hair a little life," Marissa answered as
she ran her fingers through his long blonde hair. She brushed out a few
tangles before she put down her brush.
After checking the temperature of the curler, Marissa squirted Christian's
hair with a heat protection spray before she took hold of a clip.
Christian watched her with interest as she clipped his hair into big
sections. The clips felt odd in his hair and he felt uncomfortable
sporting them, but he sensed that Marissa did not seem to pickup on his
unease.
Once the last clip was in place, Marissa started curling his hair from an
inch before its root before proceeding down with the large barrel that left
loose waves of hair in its wake. Marissa moved onto the next section of
his hair as she curled it again before she released some of the sections of
his hair down from their clips. She moved from one section to the next
before she finished curling his hair and ran her fingers through the curls
a few times to loosen and separate them.
"Can't you use a brush?" Christian asked as Marissa continued running her
fingers through his long hair, unknowingly arousing him while she did so.
Marissa responded with a shake of her head as she told him the brush would
destroy the curls and leave his hair only wavy. Christian's eyes fixed on
hers as asked, "Is that really a problem."
"It's not the look I'm going for," Marissa countered, disregarding his
complaint by continuing to run her fingers through his hair. Once she
finished, Marissa set his curls with her hairspray.
The flowery scent of the hairspray made Christian's manhood twitch. His
eyes darted away from Marissa as she continued to spray his hair. 'Get a
hold of yourself,' Christian counseled himself while he fixated his eyes on
the grouting of the floor tiles.
After finishing spraying his hair, Marissa turned her attention to doing
his makeup. Christian watched as she produced a makeup bag and began to
take out cosmetic after cosmetic.
"Is that all for me?" He asked with some alarm.
"Relax. It's all going to look understated. I wouldn't step out the door
with you if you looked like a Drag Queen."
Christian nodded, hoping that he was in good hands. Marissa started with
his foundation before she coated his lips with lipstick.
Smacking his lips at his direction, Christian watched as Marissa reached
for her eyeliner. Christian winced at the sight.
"Don't get that in my eye," Christian whined as Marissa began to apply his
eyeliner.
"Okay, let's make like I'm Claire and you're that weird girl played by Ally
Sheedy. Just close your eyes like this and let me do what I got to do,"
Marissa countered.
Christian complied with his secretary's request as he said, "That scene
didn't work..."
"Well, it's working for you right now," Marissa replied, cutting him off as
she continued to apply his eyeliner. Once she finished with it, Marissa
applied his eye shadow. Christian kept his eyes closed as he asked, "Do
you really know what you're doing?"
"No, I just look this fabulous naturally," Marissa responded, unable to
hide her sarcasm before she added, "You can open your eyes now."
"I don't look like the weird chick from an 80's movie, do I?" Christian
inquired with a smile.
"No. That's not my style. I'm more into the make you over as a mall
princess so you get the cute jock look," Marissa answered.
Christian eyes popped open to flash an angry glare at her. She smiled at
him as she told him to keep his eyes open while she did his mascara.
Christian flinched as she approached his eyes with the applicator. Marissa
scolded him, "Stay still like a big girl."
Christian huffed before he managed to keep his eyes open while she coated
his lashes with the cosmetic. As she finished, she furrowed her brow.
Christian gave her a nervous smile before he asked, "Should I take it
you're getting nervous that this might not be as easy as you thought?"
A grin came across Marissa's face while she shook her head and replied,
"I've got the safest bet of anyone today."
"I wouldn't bet on it."
"Too late," Marissa replied before she finished with his makeup. With his
makeup complete, Christian got up to follow Marissa into her living room.
His eyes widened as he stole a glance at his reflection in her vanity and
thought, 'Holy shit!'
Marissa grinned at the conflicted look on her boss's face before she said,
"Wait right here."
"Where am I going to go like this?" Christian inquired, holding his hand
out to his sides.
"I don't want some nice, big, strong dreamboat to come in and swoop you off
your feet before I get back," Marissa replied with a wink.
Christian rolled his eyes at her as he watched her scurry off into her
bedroom. He stared at the pictures of her walls while he waited for her to
return.
Christian's eyes opened to their widest as he saw the large, pastel green
hat in Marissa's hands as she emerged through the doorway. Christian took
in the large, white flower ribbon that adorned it above its white trimmed
brim with a shake of his head.
"Where did you get that?" Christian inquired with his stomach churning
over the look of the hat.
"I wore it last year," Marissa admitted.
"There is nothing that I can dress you up in that is more embarrassing than
that," Christian countered.
"Let's hope you don't get the chance to find out," Marissa countered as she
walked up next to him and placed the hat atop his head. Christian cringed
as she yanked it over his head before he caught sight of the pair of white
wedges with a crochet lace top and faux cork, beige heel and platform she
had selected to pair with his outfit.
"Those look pretty high?" Christian replied, flashing his secretary a
worried look as he conveyed his concerns.
"Would you prefer real heels?" Marissa countered with a grin as the wedges
dangled from her fingertips.
Christian shook his head as he took the rounded toe wedges from her and
worked his contrasting black tight clad feet into them. As he finished
putting the second shoe on, Christian stood up and felt taller than he ever
had when he stood next to Marissa. The feeling did not last long, as
Marissa soon put on a pair of wedges of her own that reasserted her height
advantage.
"How do you feel?" Marissa asked while she dumped his keys and wallet into
a pocketbook that she was lending him for the day.
"A little nervous," Christian replied, unable to believe that she did not
recognize it on his face while she led him towards the door.
"You'll get over it," Marissa responded as she put on a light jacket before
she handed one to Christian.
"I hope so," Christian responded as he looked over the yellow jacket and
wondered if she was trying to make him look like a marshmallow peep.
"You better, because you need to give a real performance today."
"What's that supposed to mean?" Christian asked as he put his arms through
the sleeves of the bright yellow jacket.
"You're going to act like a girl through and through."
"Why?"
"Because we bet that you could make a believable girl. I'm not going to
stick with my part of the bet if you're going to go in and there and act
like John Wayne."
"Did John Wayne wear wedges too?" Christian joked.
"No, but he did wear big hats."
"Not this big," Christian replied as he clasped at the bright, floppy hat
upon his head.
Marissa shook her head as she replied, "Well, I'm not going to be
humiliated because you choose to act like a guy to give yourself away."
Christian shrugged before Marissa inquired, "Are we clear?"
Christian gave her a nod before she placed on a small hat and opened the
front door for him. Christian shook his head as he said, "Wait a minute!"
"What?"
"You don't want to me to give myself away, but I'm the one wearing this
hat?" Christian inquired.
"I can't wear the same thing two years in a row."
"Why not?"
"A girl needs variety. It's the spice of life."
Christian gave her a hat an inquisitive look while he stepped outside
before Marissa locked the door to her apartment and led him towards the
elevator. As they rode the elevator down, Christian asked, "Okay, what is
with the mini-hat?"
"What? You wanted to wear it and, now, that I'm wearing it, you don't like
it. Is that it?"
"No. It's weird looking. It looks undersized."
"It's stylish," Marissa rejoined as she clasped the red fascinator that
rested on top of her head, which was adorned with matching red feathers and
bows.
"If you say so...," Christian countered.
"I saw Kate Middleton wearing one just like it."
"Oh, so, it makes you feel like a princess?" Christian joked.
"Exactly. That's why I didn't give it to you. I didn't want you running
off with prince charming while I'm stuck with some seedy bettor."
Christian smiled at Marissa's kidding while they exited the elevator and
left the building. As Christian walked beside her on the sidewalk, Marissa
asked, "So, how do your feet feel?"
"Fine," Christian countered.
Marissa smiled as she said, "Those are comfortable shoes."
"Do you have a pair of them?" Christian asked.
"You're wearing them," Marissa countered.
"Really?"
"You didn't know we wear the same size?" Marissa asked.
Christian shook his head before Marissa added, "What did you think I meant
by saying you'd be wearing my heels."
"I thought you meant heels you picked out."
"No. I much prefer the literal meaning."
Christian's mind raced as he thought about the fact that he was wearing a
pair of his secretary's shoes. Marissa grinned at him as she asked, "So,
what pair do you want to wear on Monday?"
"Let's not get ahead of ourselves."
"I'm an optimist," she replied before adding, "I think you always liked
that red pair I wear sometimes."
"I wouldn't know," Christian lied.
"Really, you stare at them enough."
Christian blushed in response, prompting a smirk to come across the face of
his secretary. He was embarrassed that she noticed the looks he gave her
shoes. 'God, I hope she doesn't think I have a shoe fetish,' Christian
thought.
As they continued down the sidewalk, a man walked past them and turned his
head to look them over. A smile came across the man's face as Christian
looked over his shoulder and caught the man's glance.
"That guy just checked us out," Christian whispered.
"Did you think we were going to be inconspicuous with the hats?" Marissa
replied, amused by Christian's surprised tone. She smiled as she added,
"And that's one for one for me, girlfriend."
Christian shook his head before he saw the bar a block a head of them. He
could hear a crowd cheering at an outside television that was carrying the
broadcast of a late afternoon race.
Christian's heart started to race as they approached bar. Marissa clasped
his arm and led him through the crowd. Christian sucked his lips into his
mouth, tasting his lipstick. He was afraid that one of the bettors would
see him for what he was as he passed through them.
They made it through the bar doors and looked around the crowded room.
Marissa led him towards an open two-seat table and sat down before a
waitress came over and took their drink orders.
She gave them short compliments about their hats and outfits before she
scurried off to place the order with the bartender. Christian's eyes
fixated on the waitress's shapely rear that was hugged tight by a pair of
skintight, black jeans.
The feeling of Marissa's long fingernails digging into his right hand
caused Christian's head to jerk towards his secretary. He flinched as he
pulled his hand off the table and covered his right hand with his left.
Marissa shook her head at him while she leaned over the table to quietly
remind him, "Remember, act like a girl! Step one, don't ogle other girls!"
"I wasn't..."
"I saw you looking at her ass and looking at her tits. Stop it!"
"I thought that women looked at other women."
"To see what they're wearing, and how they look..."
"To judge them," Christian corrected.
"Maybe, but not eye hump them," Marissa rejoined as she pointed her finger
in his face.
"Fine," Christian replied while continuing to rub his hand.
The waitress returned a few minutes later with their cocktails and placed
them on the table before Christian paid for the drinks. He struggled to
keep his eyes away from her cleavage that was spilling out of her snug,
black tank top while he waited for his change. After giving her a tip, the
waitress walked away and left them to talk.
"That's two for two, and one of each sex," Marissa reminded Christian.
"Okay. Maybe you'll win," Christian admitted.
"I've already won."
"How do you know?"
"Nobody's said boo. The only way they'll know is if you let them."
"I wouldn't be so sure."
"I like my coffee with a little cream, no sugar," Marissa replied as she
took a sip of her drink, ignoring her boss' alleged doubts.
"Don't get ahead of yourself."
"You're the one who's out in front of her skis," Marissa retorted.
The two continued to talk while the bar grew even more crowded. They
watched as more men and women placed bets throughout the place. Their eyes
focused more on the dresses and hats of the other girls in the
establishment.
Marissa would stop girls as they walked by to compliment them. Christian
found himself doing the same, struggling to keep up a raspy, higher voice
that seemed to throw the girls. Marissa smirked at his voice. It almost
seemed like he had practiced a girl's voice to keep up the act.
With each girl that walked away from the table without giving any hint of
knowing that Christian was a man, Marissa grinned as she whispered another
hint of Christian's future.
"I expect my secretary's heels to be three inches or higher."
"Always give me drafts unstapled."
"No starch on my dry cleaning or else."
"I expect my secretary to wear hosiery everyday, you know, just for that
professional look."
Each reminder sent a quiver through Christian's body. While Marissa
finished saying another, a man walked over and gave them a compliment.
Marissa responded with a thank you that Christian seconded before the man
made a clumsy attempt at a joke. Christian laughed in response prompting
the man to focus his attention on him.
Marissa smirked at the attention the man was giving Christian while they
each sipped on their second flirtini of the evening. Her eyes widened as
she saw Christian blush and laugh at another comment as the man's body grew
closer to Christian's.
As she watched her blushing boss, playfully brush his hair to his side
while he flirted with the guy, she realized that she had been duped. His
hesitation to accept had been act. She knew that there was no two ways
about it. The more she thought about it, the more obvious it was that he
never would have accepted her bet unless he wanted it all along. She shook
her head as she thought back to how the whole thing started. He had
started the conversation and led it to the point where she felt challenged
enough to make him put up or shut up.
'He fucking played me,' she thought as she stared at him and crossed her
arms.
Christian's smile left his face while he looked at his secretary and
realized that she suspected something was wrong. He separated himself from
the man and asked, "What's going on?"
"I think I won," Marissa replied, not wishing to state what she felt was
obvious in the presence of Christian's would be suitor.
"You were right," Christian admitted.
"So, a full month of heels for you," Marissa leaned across the table to
whisper in his ear.
"Uh...Don't remind me," Christian responded, trying his best to feign being
upset.
"I'm sure I don't have to, girlfriend," Marissa replied with a shake of her
head.
-----------------------------------------------------------------------
Marissa got to work early on Monday morning. She walked into her boss's
office and placed her purse down on Christian's desk. She turned on his
computer and logged onto it. She was eager to see what her boss could make
of himself with the makeup, outfits and heels she had sent him home with
after they returned to her apartment from the bar as she waited.
She shook her head, wondering what level of skill he would demonstrate with
his self-feminization. She figured that he was probably an expert, but he
was likely going to try to make amateurish mistakes in an effort to make
her think otherwise.
The sound of the door of the office opening brought Marissa's eyes away
from the screen and towards the doorway to her new office. She rolled her
chair towards the edge of the executive's desk to peer through the doorway,
unobstructed.
Her eyes widened as she saw her boss standing in a pair of nude colored,
three-inch high heels and a pink, faux wrap dress. She got out of her
chair and approached him as he took off his jacket that exposed the
surplice neckline of the peace palm patterned dress. She never noticed how
thin his upper arms were until she saw how they looked as the emerged from
beneath the dress's short sleeves. His nude pantyhose covered legs
shimmered in the morning light that bathed into the office as he adjusted
his feet in his pumps that were adorned with matching grosgrain bows at the
vamp. His long hair was styled with waves and his makeup was nearly
flawless. She smiled at him as she stood up and said, "Let me take a look
at you."
Christian stopped at her old desk and let her look him over. He squirmed a
little, wondering if she could tell that he was practiced with makeup. He
cast a glance up at her eyes before she said, "You look great."
Christian shook his head and lied, "I feel like an idiot."
'No, you don't,' Marissa thought before she feigned sympathy for him and
gave him a brief hug.
Christian thanked her for her kind words while he put his black purse down
on the desktop. Marissa realized that the purse was not the same one that
she had given him on Saturday. It was a similar design, but the buckles
were slightly different.
A slight grin came upon Marissa's face as she thought back to the thoughts
about Christian that had consumed her since Saturday night. Originally,
she had been planning to just to tease him with being a secretary for a
month, but, now, she knew that she was going to hold him to his bet. She
knew that he wanted it. She also decided that she was going to be a far
more demanding boss than he was to see just how much he wanted it.
As Christian pulled out his chair, Marissa said, "Chrissie, before you sit
down, can you get me a cup of coffee?"
"Chrissie?" Christian asked, raising his eyebrows as he did so.
"You don't look like a Christian."
"What do I look like, an Anti-Christian," he rejoined with a smirk.
Marissa gave him a shake of the head, as she replied, "No, but definitely
more of a Chrissie."
"There are girls named Christian."
"Yes, but I don't want anyone confusing you for that old tyrant."
"I was a tyrant?" Christian asked with his hands pressing his dress onto
his hips.
"Chrissie, you were never a boss, how could you be a tyrant?" Marissa
countered with a smile.
"So, you're just going to pretend I'm two different people?" Christian
inquired.
"I don't know what you're babbling on about, Chrissie. Can you please just
get me my coffee?"
"Sure," Christian replied with a resigned sigh before he asked, "How do you
like your coffee?"
Marissa reminded him before she went back into her new office and waited
for him to bring her the cup. Christian hurried towards the kitchenette to
make her coffee. Once he was sure that he was out of her view, Christian
let a smile come to his face.
He reached for Marissa's cup that was on the drying rack and stuck into the
coffee maker. He laughed to himself about how ridiculous it was to feel so
excited to be doing something as trivial as making Marissa a cup of coffee.
The request to do so, however, was making him feel excited that she was
really treating him like her secretary.
He struggled to force the grin off his face as he approached Marissa's
temporary office with her cup in his hands, not wanting to give away that
he was in a trap of his own design. Christian walked into his office,
holding his head low as he placed the cup on the coaster on the desktop.
"Thank you, Chrissie," Marissa replied before she took a sip and said,
"Superb work."
"Thank you," Christian responded meekly, struggling not to smile at her
praise.
Receiving the response she desired, Marissa pressed further, "Chrissie,
what are you planning on wearing tomorrow?"
Christian was confused by the inquiry. He asked, "I'm not quite sure yet."
"Have you purchased anything to wear? You can't just keep wearing those
same old outfits I sent you home with. Most of them aren't going to be a
good fit anyway," Marissa replied before taking another sip of her drink.
"I have bought some stuff," Christian replied with an understatement.
"And you're choosing to wear what?"
Christian shrugged before Marissa continued, "I need to approve your
outfits."
"What?" Christian replied, horrified and aroused by having to get his
clothing choices pre-approved by his boss.
"Chrissie, I'm running a professional office here. I know your shoes will
be appropriate, but the rest, well, that's an open question."
Christian squirmed, feeling his manhood pushing his gusset away from his
body before Marissa continued, "I want to be sure that you understand what
appropriate attire is for a girl in your position."
"I think I got it," Christian replied, humiliated and excited about being
talked down to by his former subordinate.
"Okay, so what are you going to wear?"
"I've got a couple of options."
"Name them," Marissa demanded.
Christian paused before he said, "I was planning to start with a skirt."
"Good choice. You know that I insist that my secretary only wear skirts or
dresses."
"Why?" Christian asked, delighted by the requirement he was planning to
comply with in the absence of any such rule.
"It gives a secretary a more proper appearance. Pants should be reserved
for management types."
"You wore pants..."
"I was always a management type, even if I was only an assistant," Marissa
replied, cutting Christian off.
"Okay."
"Now, what are you going to pair your skirt with?"
"Probably a blouse."
"Nothing too low cut."
Christian blushed at the statement before he admitted, "I couldn't really
pull that off."
"No, you're too flat," Marissa said with a smirk as her eyes darted to his
faux bust.
"I think I'm pretty big," Christian replied, peeking down at his chest
before he patted his padding through his dress.
"Big enough. A secretary shouldn't be distracting," Marissa chided.
"I'll keep away from the low cut tops," Christian replied.
Marissa nodded before she said, "And your legs."
"I was going to wear a pair of pantyhose or tights."
"Good. I don't have to remind you that a girl must always wear pantyhose
or tights with a skirt or dress. Bare legs are simply not professional. I
don't care if it's a hot day. Men have to wear pants when it's a 100,
secretaries have to wear hosiery. Understood?"
"Yes, Marissa," Christian replied, aroused by the order he would have no
qualms about complying with.
"Now, you know hosiery is a difficult animal."
Christian gave her a curious look before Marissa explained herself, "They
run! They tear! They're a complete and utter bitch! That's why you
always have to carry two things with you."
"What's that?"
"Clear nail polish to stop runs in their tracks and a change of hosiery in
case it's not salvageable," Marissa answered as she counted off each on a
finger.
Christian nodded before Marissa continued, "I will not tolerate a shabby
appearance. I will be giving you a pantyhose inspection everyday to make
sure that your hosiery is presentable."
Christian's member throbbed at the demand and thin threat his boss was
leveling on him. Christian nodded to convey he understood her.
Marissa nodded back at him before she told him to ensure that his hair and
makeup was done in a neat professional manner as well. Christian asked,
"Is what I did today okay?"
After a long pause, Marissa answered, "It's acceptable. Just don't let me
catch you in pigtails."
"I promise that won't be a problem," Christian replied with a laugh.
"Good, now, I need you to update the spreadsheets regarding our accounts
receivables."
"Okay," Christian replied.
Marissa stared at Christian's motionless action and asked, "Can you do it
now?"
Christian nodded in response to her stern tone. He turned and walked away
from her office, aroused by the order.
He walked over to his new secretarial desk and sat down on the seat. He
pulled it away from her desk and observed the plastic, padded arms that
were in just as sharp of contrast to the wood and leather arms of his
executive chair as the low back was to the high back of the chair that
Marissa was now sitting in.
Christian sat down in the seat and felt the height difference between
himself and Marissa. His feet dangled off the floor as he sat back in the
chair, like a child's. Christian reached for the lever but found that the
seat would not adjust an inch lower.
"What the hell?" Christian wondered aloud as he bounced his rear against
the chair hoping that it would lower so that his feet could touch the
floor.
Marissa stifled her laughter at the sound of Christian's attempts to fix
the broken chair before he gave up his futile efforts. Christian pulled
the chair under the desk and slid his rear towards the front of the seat
until his feet rested on the ground.
He began to update the spreadsheet as Marissa had done each morning since
she started working for him. He spent most of his morning doing it,
pausing only to answer the phone.
The first few phone calls were frightening for Christian. He recognized
some voices on the phone, even though he had not spoken with most since he
hired Marissa. Despite his efforts to throw his voice, he was sure that
someone would recognize his. It was only a matter of time in his mind.
While the people he spoke with gave no hint that they knew who he was,
Christian could tell that some of the people were unsure of his gender.
They avoided referring to him in gender pronouns, making him realize that
his voice was androgynous at best. Under the circumstances, he was happy
with the confusion since it was better than being constantly referred to as
a man, which would have been shattered the feminine illusion he was trying
to exist within for the month.
Shortly before he finished updating the spreadsheet, Marissa stepped out of
her new office and smirked at Christian's perched position on the chair.
She said, "How are you doing?"
"It's going good. I'm almost done."
"Good."
"Marissa, is your chair broken?" Christian asked.
"Well, no, but YOUR chair's been broken for a while," Marissa answered,
taking care to correct her boss in the process.
"Why didn't you ask for another one?"
"It worked for me. It was comfortable."
"Well, it's too high for me."
"Chrissie, you're only going to be here for a month, so we're not going to
replace it. You'll get used to it."
"It's uncomfortable," Christian replied as he reached for his lower back
that was starting to ache from the lack of support, just like his feet were
aching from the arch caused by his shoes.
"Being a secretary often means being uncomfortable, besides I like that
you're sitting like that."
"Why?" Christian asked, upset about having to spend a month with the same
ache in his back, even as he was aroused at her executive dismissal of his
reasonable request.
"You're not sitting back in the chair. If I need to call you, you can snap
right up and get into my office quicker."
Christian blushed, humiliated to be turned on by her claim. Marissa could
sense his arousal as she said, "I need you to place a lunch order for me."
Christian nodded as he took down her order before Marissa stepped out of
the office to head for the ladies room. Christian reached for his phone
and called in the order at a nearby eatery before he placed one for himself
as well. He wrote down when he could pick it up before he went back to
finishing his spreadsheet.
After Marissa walked back into the office, she asked Christian if he had
placed her order. After confirming that he had and when it would be ready
for pickup, she told Christian to drop off her dry-cleaning on his way to
the luncheonette.
Christian was surprised by the order, since he never assigned Marissa
personal tasks. He knew that she was deliberately pushing him harder than
he did with her. He tried to act passively upset about it, but his efforts
did not fool Marissa.
Marissa gave Christian the money for her lunch and dry cleaning before she
sent him out the door with her dirty clothing in hand. Christian walked
through the hallway and road the elevator down to the underground parking
garage before he remembered that he had given up his reserved spot to
Marissa for the month.
"Shit," Christian muttered as the doors opened. Christian pressed the
button for the ground floor and road the elevator back up a floor. After
the doors opened again, Christian headed for the front door of the building
and pulled it open.
Christian walked out of the building and felt the warm sun on his skin.
The breeze up the skirt of his dress was different from anything he had
experienced before. Still, he hurried towards his car that was parked not
far from the building, not wanting to dawdle with tasks at hand.
Christian opened his car with his key fob and got behind the wheel. He
slipped his heels off and put on a pair of flats before he started the
engine and pulled out of the parking spot.
After exiting the parking lot, Christian drove down the street to the dry
cleaner that was located a few blocks from the eatery he had placed the
lunch order with that afternoon. Christian parked in the shopping center
and started towards the dry cleaner with Marissa's clothing in hand and his
pocketbook pressed tightly against his side.
Christian greeted the old Asian woman behind the counter with a smile as he
placed Marissa's clothing down on the counter. The woman examined the
clothes as she rang them up before she said with a heavy Korean accent,
"These aren't for you?"
"Oh, no," Christian admitted, knowing that the woman knew that he was
dropping them off for another person.
"Who they for?" She asked.
"My boss," Christian answered, struggling not to smile at the way his
admission sounded.
The old woman paid his answer no mind as she told him the amount that was
due. Christian paid it from the money that Marissa had sent out the door
with before he took the dry cleaning ticket.
Christian walked out of the dry cleaner and went back to his car. He then
drove over to the luncheonette. Christian got out of the car and walked
into the crowded building. Christian looked around, hoping that he would
not recognize anyone in the crowd. He was relieved not to before he went
to the cashier and waited on line.
As he waited, a young woman walked over behind him to stand on the line
with her purchases. Christian could see her looking him over. He felt
nervous for a second before the girl realized that he had noticed her
looking at him.
The girl smiled as she said, "I love those shoes. They're so cute."
"These. Oh, thanks," Christian replied before he complimented her bag.
The girl smiled as she asked where Christian got his shoulder bag.
Christian admitted the discount retailer he had placed his online order
with to the girl's surprise.
The girl shook her head as she said, "I haven't shopped there since I
became a CPA."
'Well, aren't you the lucky one,' Christian thought to himself before he
responded, "Well, I've got to economize."
"What do you do?" The girl inquired.
"I'm a secretary," Christian answered.
"Oh, that's nice," the girl replied, adopting more than a hint of an air of
superiority over him based on their respective job titles.
While Christian was slightly upset about the cute girl's attitude, he was
also aroused by it. He was also happy enough to be able to turn away from
her since the cashier called him forward.
Once he stepped up to the cashier, Christian told the woman his order. She
called it in from the back as he paid the bill before he stood off to the
side waiting for the staff to drop it off for him. Christian thanked the
man who dropped it off. The non-English speaking man gave Christian a
smile in return before Christian stepped out of the building and went back
to his car.
Christian drove back to his office and pulled into the parking lot. He
drove past the spot he had left and frowned as he saw that the spot had
been taken. Christian drove down the next aisle and found no spots.
He sighed as he pulled a few rows further away from the building and found
a spot. He parked his car in one of the last rows of the parking lot. He
then slipped his heels back on before he began the long walk back to the
building.
Christian was careful to watch for cracks and grates as he walked around
the parking lot. He was not used to it in flat shoes, let alone heels. He
examined the uneven pavement as he endeavored to maintain his balance
before he reached the sidewalk that surrounded the building.
Christian used Marissa's key card to enter the building and made his way to
the elevator. After entering the office suite, Christian gave Marissa her
dry cleaning receipt and lunch. Marissa gave Christian a perfunctory
thanks before she told him to eat at his desk.
"Why?" Christian asked.
"I don't want to miss any calls," Marissa replied.
Christian nodded, understanding her request while he went back to his new
desk and sat down. He sat towards the front of the seat and hunched over
his desk while he ate. He handled three calls while he ate before he
cleaned up his desk.
As Christian walked back towards his desk, Marissa called out to him.
Christian went into his former office and asked, "Yes?"
"I need you to clean up this stuff," Marissa said as she stared at the
computer monitor and waved her hand in the general direction of what
remained of her lunch.
Christian was shocked by the order. It was almost as if Marissa knew the
role he wanted her to play. Christian nodded while he approached the desk
and scooped up the empty wrapper as his manhood swelled. He clustered the
garbage with Marissa's empty glass of water and dirtied utensils and
carried them out of the room.
He never turned to see Marissa's smile as he struggled to hide his until he
reached the office's kitchenette and placed the glass and utensils in the
sink. After throwing out the wrapper and Marissa's used napkins, Christian
turned on the sink and began to wash the glasses and utensils. With each
turn and wring of the sponge, Christian felt more like a secretary than
ever.
Once he finished, Christian started back to his desk. To his surprise,
Marissa was waiting for him.
Christian looked at her, waiting for her to say something before Marissa
decided to see how far she could push him. She furrowed her brow as she
said, "Chrissie, my tag in my underwear is chaffing me, I need you to cut
it out."
Christian's eyes widened at the very personal request that went well beyond
professional boundaries. Marissa reached for the pair of scissors on his
new desk and handed them over to Christian.
Christian took the scissors by the handles and watched as Marissa lowered
her pants a little. She pulled the tag out of her panties, which had the
effect of drawing her panties away from her body. Christian was unsure if
she was trying to turn him on as he clutched the tag and caught sight of
the crack that ran between her shapely butt cheeks.
His eyes darted away from it, feeling it was inappropriate to gawk as he
concentrated on cutting off the tag. Once it was clipped, he let it go and
watched the waistband of Marissa's panties cling back to her hips.
Marissa smiled at his willingness to lower himself to fixing her underwear
while she brought her pants back to her hips. She then assigned him some
documents to copy and file, knowing that it would take him until the end of
the day.
Christian went to the filing cabinet and retrieved some documents that
Marissa wanted before he took another file from her and began to make
copies. Christian listened to the machine hum as it took in the papers and
churned out the copies.
His feet ached as he moved around the copier, collecting each bundle and
fastening them together to save time. Once he fed through another copy
job, Christian scurried over to the file cabinets to make room for the
files that Marissa wanted put away.
Christian moved files from one drawer to another to make room for the large
file set. His back ached as he hunched over the drawers, helping to
maintain his balance with one hand on the top of the three drawer high
cabinets.
After hearing the copier beep to alert that the job was complete, Christian
hurried back across the office to feed the next job. Marissa caught sight
of Christian's hurried steps and grinned at his eager efforts. On his
face, she also recognized the pain in his feet that was being caused by his
feet being unaccustomed to her shoes.
"At least he's getting the full experience," Marissa chuckled to herself.
Christian ran the last set of documents through the copier before he moved
back over to the filing cabinets. He then went back to reorganizing them.
As the workday ended, Christian said goodbye to Marissa and headed out the
door of the building. The warm spring air of the evening felt good on his
skin as he walked to his car. The sensations still felt strange to him as
his pained feet pressed against the sidewalk.
After he drove home, he made the short walk to his apartment building that
he had deliberately kept a low profile in since moving there a few weeks
earlier. He used his keycard to enter the building before he used it to
get the elevator to take him up to his floor.
A smile came across his face as he thought about getting out of his heels
and into a pair of flats. As he approached his door, the door to his
neighbor's apartment swung open. Christian reached for his door and turned
his head away from the open door.
"Miss?" The girl asked, confused to see a woman trying to enter
Christian's apartment.
Christian stayed silent, trying to play off that he thought she was
speaking to someone else in the empty hallway as he pushed his door open.
"Miss," the girl repeated.
"Yes," Christian replied with a smile, unable to ignore her any longer.
The girl's eyes widened as she recognized Christian's face.
"Holy Shit!"
"I can explain."
"You look great," Sadie said as she looked him over.
"Uh...thanks," Christian replied, confused by the praise and the interest
that the woman was taking in him. She had never showed any interest in him
prior despite his initial attempts to draw her attention after he moved in.
"Why are you dressed like that?"
"It's a long story."
"I have time."
"You look like you're going out?" Christian countered."
"Oh, I'll make time for this. Why don't you come inside?"
Sadie's invitation was one he had been hoping to receive from the moment he
meet her. He had not expected to receive it in a dress, however. Still,
Christian decided he could not pass up the opportunity to spend a few
minutes with the pretty girl.
Christian closed his door, followed Sadie into her apartment and looked
around. The apartment had the same dimensions as his, but the furnishings
and decorations were far more feminine.
"This place looks great," Christian said.
Sadie accepted his compliment before she asked if he would like something
to drink.
"Water would be great," he answered.
"Trying to purify yourself?"
"No."
"Trying to stay thin?" Sadie then inquired.
Christian responded with a shake of his head before she returned with a
glass of water and told him to take a seat. Christian sat down on the
couch before Sadie sat down a few inches away to his side. Sadie crossed
her legs and asked, "So, are you going to tell me?"
Christian nodded his head as he explained the bet that he had lost and the
consequences that he faced for losing it. Sadie laughed as she said,
"That's an odd bet for a man to make."
Christian blushed at her words before he said, "Marissa's convincing."
"I'm sure you didn't need a lot of convincing."
"No. She talked me into it."
Sadie shook her head as she said, "No man gets talked into a bet like
that."
"What are you talking about?"
"The only man who would agree to do something like this wants it."
Christian shook his head, trying to defend his masculinity, before Sadie
added, "You wanted to lose."
Christian shook his head again before Sadie said, "Do you want some wine?"
"No. I don't want to be a bother," Christian stammered as his nervous
fingers fumbled against one another.
"It's no bother, and I insist."
"Okay," Christian replied as Sadie got up. He heard her open a bottle
before she returned with two glasses. She handed one to him before she sat
down and said, "Now, are you ready to stop lying to me?"
"I wasn't..."
"You still are," Sadie interjected.
"I'm not...," Christian started to reply before Sadie brought her hand down
upon his nylon-covered knee. She began to stroke it before she raised her
eyes to catch Christian's.
A smile came across her face as she said, "I like you, but I won't tolerate
you lying to me."
Christian nodded as a fluttery feeling was stirred up in his stomach.
Sadie leaned closer to him and asked, "What's your name?"
"You know my name..."
"No. What's your name?"
"Chrissie," Christian admitted.
"Pretty name. So familiar and easy too," Sadie said with a smile before
she took a sip of her wine.
"You don't think it's strange," Christian replied, dropping back into his
practiced feminine voice.
Sadie's eyes widened at the sound of it before she said, "We're all a
little strange. That's why I stopped going to my shrink."
"Why did you go to shr...a psychiatrist," Christian asked.
"My father was a cross-dresser and my parents divorced...largely because of
it, or so my mom says."
"Oh."
"That's why I can spot one and tell the difference from a boy in a costume
and a boy who knows his way around a makeup bag."
Christian's manhood hardened