The Carhop
Belladonna
[Author's note: Thanks GFriday for the suggestion in one of your
reviews. I had completely forgotten about Carhops until I saw it.]
Serena Davis called her boyfriend over to her bed. Andy Iverson was not
the least bit suspicious about her motives. He had been dating her for
over a year, and he knew that he could only do himself harm if he ever
questioned her when she drew him close to a mattress or the backseat of
a car.
Serena smirked at her boyfriend as his hand began to creep up her skirt.
"Not tonight, babe," she said, prompting a look of disappointment on the
boy's face.
Andy was let down by her words, but he was not inclined to try to change
her mind. He had tried in the past when he figured she was playing hard
to get, but he had learned that her no actually meant no. While he knew
that other girls his age liked to make their men pursue and practically
beg them for sex, Serena was not one of them.
Serena was an honor roll student, and she was quite skilled at getting
what she wanted. While she was not among the most attractive girls at
the school, she was among the heaviest courted. Andy knew that every
boy, who was not among the popular crowd, wanted Serena as their own.
Andy was also well aware that he was lucky to have her. He knew the
reason that she was attracted to him as well. Serena was well known
around school for exclusively dating effeminate looking men.
While Andy often hated his appearance, he knew that it was the source of
Serena's attraction to him. Serena's love had made him no longer ashamed
of his physique.
Andy's height was below average for his gender. He stood only 5'6".
While he knew other guys that had no trouble finding girlfriends despite
their short stature, he felt that he was also handicapped by his thin
frame. He had difficulty keeping weight on, and he struggled at times to
get over 100 pounds.
Andy's other features failed to convey his masculinity as well. He had
no hair on his body beyond his underarms, legs and privates. His heart
shaped face sported a small nose and small, rounded chin. His hair had a
bright, copper red tone that failed to excite many girls. Additionally,
myths about the relationship between the size of one's feet and one's
penis did him no favors with the girls. Andy had very small feet for a
man, as well as small hands.
Serena's insistence that he grow out his hair further contributed to his
failure to sport a masculine appearance. Andy did not like the way his
hair made him look, but he kept it because of how much his long hair
seemed to turn Serena on.
Serena's attraction to him was the one thing that made Andy feel good
about himself. She was a kind hearted girl who seemed to enjoy
everything about his appearance. She gave Andy hope that a woman could
possibly love a man like him. Every time he looked down into Serena's
eyes, he felt a surge of passion that had been absent from him before he
began to date her. She seemed to love him, and that was all Andy wanted
from a girl or felt that he had a right to expect.
They were both senior's in high school as they sat together on Serena's
bed that fall afternoon. Serena's parents were both finishing up their
workdays in the city like they did practically every weekday. The hours
after school at Serena's before her parents came home were the happiest
of Andy's week. He enjoyed spending time alone with her. It was not just
the occasional sex that made him enjoy her company. Everything about her
made Andy had happy to be within her presence.
Serena took Andy's hands and smiled at him as she stared up into his
eyes. She had become experienced at asking what she was about to ask.
Her prior two boyfriend's had rejected her request, and she had learned
from the clumsiness of her prior mistakes.
She pushed her lips up to his ear and asked, "Would you like to make a
deal with me, babe?"
Andy pulled his head away from her and gazed down into her eyes.
Figuring that he could not possibly object to whatever she asked of him,
Andy replied, "I'm sure I would. Just tell me what you have in mind?"
Serena smiled and said, "You know that Claire's Diner is hiring, don't
you?"
"Claire's? Oh that chain diner two towns over?"
"Yes, that's the place."
Andy nodded and said, "I heard about them. That's where the waitresses
dress up like 50's waitresses and bring your food on skates. Kind of
like an erotic Sonic."
"Yup."
"Well, what are you telling me for? Do you want to work there? Is that
it? I'd love to see you in that uniform. I'm sure you'd look cute," Andy
responded.
"Not exactly," Serena replied.
"Well what do you have in mind?"
"I want you to work there."
"What? Are they hiring cooks?" Andy asked.
"No waitresses," Serena responded.
Andy blinked a few times as he tried to understand what Serena was
trying to ask him. Suddenly, he understood and replied, "Wait a second,
do you want me to be a waitress?"
Serena smiled and said, "I think you'd look cute in the uniform too."
Andy blushed at her response and said, "Be that as it may, I don't think
anyone would buy that I was a teenage waitress?"
"Well, you wouldn't really a waitress, you'd be a carhop," Serena
responded.
"That doesn't make it any better, Serena."
"I know you might be reluctant to do this, but I think you would look
great."
"Thanks, I guess. I can't do it though."
"Why not? You have the perfect face. It'd be so pretty if we put a
little makeup on it."
Andy froze as he looked at his girlfriend. At that moment, he was more
certain than ever that Serena was attracted to him because of his
effeminate appearance. It was more than that, he quickly surmised. He
realized that she liked men that looked like girls. He was not sure how
he should take the revelation. It made some sense to him. He knew
Serena's ex-boyfriend's were not masculine looking. However, his male
ego was telling him that her statements and request were an affront to
his very identity.
However, Andy's desire to stay with Serena overtook his concerns, so he
asked, "Well, what do you I get out of the deal?"
Serena smirked and answered, "If you can get the job, I'll make love to
you anyway you like everyday after school for a week?"
"Really?" Andy exclaimed.
"Don't be so obviously desperate, babe. We did it yesterday."
Andy nodded and asked, "Well, what if I don't get the job?"
"If you don't get the job, I won't hold it against you. You won't get
the sex, and I'll get to make you over, so that's really my reward if
you don't get the job. That's it. Hell, you can even back out if you
don't think you can do it once I get the makeup on you."
The allure of having sex with his girlfriend five days in a row was too
much for Andy to turn away from. Even though he knew that he was stupid
for agreeing to do it, he smiled and took Serena up on her offer.
Serena said, "Let's get started then."
Andy followed her into the bathroom. She showed him her razor and her
shaving foam and told him to remove all the hair from his armpits and
legs.
Andy nodded. After Serena left the bathroom, he striped down to his
underwear and turned on the shower. He entered the shower and removed
all of his body hair. He felt a little odd doing it. He felt that he was
undercutting his own masculine identity by willfully making himself look
even more feminine. He was ashamed enough about his girlish appearance.
He knew that the loss of his body hair would only make him look like
less of a man. Still, the terms of the deal made the loss of his body
hair manageable for him. Andy stepped out of the shower and toweled
himself off. He placed on his underwear and then opened up the bathroom
room door.
Andy saw Serena standing in the hallway as he exited the bathroom. She
then brought him back into her bedroom. Andy walked into her room behind
her and took a seat on her bed. Serena took out a bra for Andy and a
pair of chino pants as Andy watched as she selected his clothes. She
then walked over to Andy carrying her beige bra. She wrapped it around
his body and hooked it behind his back. Andy straightened out the straps
while Serena pulled out socks to stuff the bra with. Andy felt that the
bra pinched his skin a little as it rested over his flat chest before
Serena inserted the socks. After she finished stuffing Andy's bra,
Serena gave Andy two pairs of panties to help keep his member tucked
away. She smirked at Andy and said, "Double bag your little guy to keep
him in place."
Andy smiled at her and went into her bathroom carrying the panties and
the pants. Serena shook her head at him as he walked out of her room.
She had seen him naked several times before, but she knew that Andy did
not like her seeing him naked unless sex was imminent. She found his
selective modesty peculiar and unnecessary.
As Andy finished tucking himself away and drawing up his pants, he heard
a knock on the door. He froze as he wondered if one of Serena's parents
had gotten home early. He started to shake as he knew that he would
either have to exit in their daughter's pants or nude. His anxiety faded
when he heard his girlfriend's voice. She said, "I've got the perfect
top for you, Andy. Want to take a look?"
Andy opened the door and looked at the shirt in his girlfriend's hands.
The three-quartered sleeved t-shirt had red and white horizontal
stripes. Serena handed Andy the shirt, and he placed it on over his bra.
He checked the shirt in the mirror and was happy that scoop neck did not
plunge down to where his cleavage should be.
Serena smiled as she saw that her boyfriend had a completely feminine
looking body beneath his head. She smiled as she took his hand and
brought him back into her bedroom to apply makeup to his face. As Andy
walked towards her bedroom, he felt the feeling of the primarily cotton
pants on his smooth legs as he moved. He found the feeling preferable to
any other clothing he had ever worn. His hand moved across the left
sleeve of his top as he sat down in front of Serena's vanity. He felt
the rayon fabric and felt himself starting to become aroused. Andy could
feel his member poking at the back of his pants, so he realized that he
would need to control his urges when he went into Claire's Diner.
Meanwhile, Serena made up a bag of cosmetics for Andy before she said,
"You're lucky you have an even skin tone. That really cuts down on the
amount of makeup you need. I think you only need a little mascara,
eyeliner and lip gloss to look super fem."
Serena decided not to apply Andy's makeup. She instead told Andy, "You
really should learn how to do it yourself."'
"Why?" Andy asked.
"Because I don't want to do it every time you end up wanting to put on
makeup."
Andy shook his head, "It's just this one time, and one day at Claire's,
if I get the job."
"That's what all the boys say."
"What boys?" Andy asked as he began to wonder if his girlfriend had done
this before with her ex-boyfriends.
"The pretty boys," Serena replied with a smile as she put his hair up
into a ponytail.
Andy decided to let the issue go since he knew all of Serena's former
boyfriends. He knew that neither she nor any of them had ever talked
about doing anything like what Serena was asking him to do. While he
knew that that could just be embarrassment on the guys' parts, he also
knew that if she had dressed them up, Serena had kept quiet about it.
Serena directed Andy as he applied his eyeliner. He stabbed himself in
the eye when he tried to put into around his left eye. Andy became a
little aggravated when Serena started to laugh at his clumsy attempt to
apply it. She apologized and told him to apply it slowly.
Andy complied with her recommendation and finished applying his eyeliner
without further incident. Andy then took hold of the mascara. He
carefully followed Serena's instructions while he applied it.
With his mascara finished, Andy moved on to his lip gloss. He paused
before he applied. He stared at his reflection and saw that the ponytail
and the black around his eyes had already given him a decidedly feminine
appearance.
Andy gazed at himself for a few more moments before Serena slapped his
shoulder and said, "Stop ogling yourself. Self love is a deadly sin, I
think."
Andy blushed and applied the pink lip gloss his girlfriend had given to
him. Andy slowly put the lip gloss applicator back into the bottle and
placed it into the purse that Serena leant him. He could not believe how
convincing a woman he was. He knew that he was never masculine looking,
but he never realized how effeminate his face and overall build was.
Serena smiled as she stared down at him and said, "There's the pretty
face I fell in love with."
Andy blushed at her words once more. He knew that his effeminate looks
contributed to Serena's attraction to him. Although he knew it, his male
ego never let him be comfortable with that fact. He had always felt he
should have been more masculine even though he knew that if he was, he
never would have secured Serena's love.
Serena gave him a good look and said, "Wait, I know what we need to
complete this look."
"What?" Andy asked as Serena went through her jewelry box. She pulled
out a pair of earrings and handed them to Andy.
Andy examined the earrings. They were heart shaped earrings decorated
with rhinestones. He put the earrings on. He smiled as he looked at them
in the mirror. He liked how they helped give his pierced ears a feminine
look that went with the rest of his appearance. He laughed as he looked
at his girlish looking ears and thought about his father. He had his
ears pierced simply to annoy his father when he came down to visit him.
He knew his father considered it unmanly for a male to have two pierced
ears. He could only laugh about what his father would think if he saw
him at that moment.
Serena then handed Andy a pair of opened back, black wedges. He placed
them on and stood up and walked around a bit to see if he could master
walking in them in a short time. He realized he could, and he told
Serena that he could walk with them on.
With his feminizing makeover complete, Andy took hold of the purse
Serena had made up for him. It contained her social security card in
addition to his phone, wallet and the makeup she was lending him.
Serena smiled at Andy and said, "Well, I guess you're not backing out of
the bet?"
"Hell, no, babe. I'm not backing out. With the way I look, I've got
nothing to fear."
Serena shook her head and asked, "Am I going to have to worry about you
dressing up all the time now?"
Andy froze. He wondered if she realized how much he was enjoying
himself. He thought to himself, 'Maybe she's picking up on something
about me.'
However, when he saw her smile, Andy realized that Serena was probably
just playing with his head. Andy followed Serena out to her car. While
he had a license of his own, he figured it would not do him any good
while he was en femme. Serena understood his fear of being pulled over
by the police en femme. She knew he would have to show his male license.
She was also as aware as Andy about how homophobic many police officers
were. She knew that if they found out that he was a man beneath his
girl's clothing, they would give him a hard time.
Serena drove Andy down to the Claire's Diner two towns over. They saw
the help wanted sign still in the window. Serena parked and said, "I'll
be waiting for you in the shopping center next door. If I'm not in my
car when you get out, I'll be in that Duane Reade."
Andy nodded as he got out of Serena's car. He walked towards the door
and watched her pull out of the parking lot before she pulled into the
shopping center's lot. He opened the door to the diner and inquired
about the opening.
Andy was given an application to fill out. He filled out the application
using Serena's biographical information. He smiled as he put her name,
address, sex, and social security number down on the paper. He knew that
if he got the job, he would be technically working Serena's first job.
He knew that his girlfriend had no work experience. Her well-to-do
parents did not want her to cut back on her studies to work a low wage
job. They provided everything she wanted, so she saw no reason to have
one. Andy could relate as his mother had kept him from having a job for
the same reasons. She too gave him almost everything he wanted. He
smirked at the fact that even though he was technically working before
Serena ever had, she was going to be getting the credit for his work.
Andy was taken into the manager's office after he finished with the
application. Andy was seated across from the manager. She was a woman in
her mid-thirties with long blonde hair.
She introduced herself as Lauren before she looked at Andy's resume. She
nodded to herself a few times before she looked over Andy and asked him
a few questions. Satisfied with his answers and his physical appearance,
she said, "Welcome aboard, Serena."
"I got the job?" Andy exclaimed.
"Yes, you did," Lauren replied as she extended her hand.
Andy shook her hand and said, "When do I start?"
"How about tomorrow at 4?"
Andy nodded and said, "Great, I will see you then."
Lauren nodded and said, "See Keri upfront about getting a uniform."
Andy nodded as he got up and headed out of Lauren's office. He went over
to Keri and asked about a uniform. Keri took him into the backroom of
the diner and gave him two uniforms in his size and a hat. She then
fitted him for a pair of white roller-skates to make sure that they had
enough ones in his size for his shift. Keri told him that he had to get
his own white socks and could wear nude pantyhose if he wanted to for
added warmth.
Andy nodded and thanked her as he walked out of the diner carrying his
new uniform and hat. He walked over into the adjacent parking lot, and
he found Serena waiting in her car for him. He told her he got the job
and showed her the red and white vertically striped dress with the white
apron that he would be required to wear the next day.
Serena smiled at him and looked at the hat. She said, "You're going to
look precious in that."
"Oh, thanks," Andy replied, blushing yet again at his girlfriend's
words.
Serena then told him that she had picked up socks and nude pantyhose for
him. He asked why she was so certain he would get the job. She answered
that Claire's would jump to hire a girl that looked like him. He smiled
at her statement, although he was a little uncomfortable being called an
attractive girl by his girlfriend even though she did not say that
directly.
As Andy took hold of the bag she had gotten from Duane Reade, Serena
started the car. She drove back to her house. Andy changed out of
Serena's clothes, removed his makeup and left before her mother came
home.
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Andy went to Serena's after school the next day. She let him and helped
him change into his uniform. Andy put on his panties in the bathroom
before he went to Serena's room and listened as she told him how to put
on his pantyhose without running them.
Andy followed her directions closely and rolled down the pantyhose like
she said before he stepped into them and slowly brought the pantyhose up
his legs. Andy smiled as he brought the pantyhose up his leg. They felt
sensual and like nothing else that he had ever worn. He felt turned on
by their soft, silky feeling and wondered why men did not wear them.
After he finished putting on his pantyhose, Andy placed on his socks
before Serena helped him put a bra on. He stuffed the bra with Serena's
socks while she took out the purse she was lending him again. She
started taking out the cosmetics while he put on his uniform.
Serena smirked at him as she saw him standing in her bedroom in a
carhop's uniform. Andy pulled at the mid thigh length dress, but he
quickly realized that that would not make it any longer.
"Love the apron, babe," Serena said about the white apron that Andy
wrapped around his dress to complete the uniform.
Andy rolled his eyes and put on the pair of cheap girls' sneakers that
Serena had bought for him. He then went to Serena's vanity and applied
his makeup. When he finished, he felt that there was no one outside of
Serena's bedroom who could possibly know that he was really a man in a
dress. He then placed on his waitress hat and asked, "How do I look?"
"Super cute," Serena replied as she hugged him. She kissed him on the
cheek. Andy hoped it would go further then, but Serena got up and said,
"Come on, girl. You've got to get moving. You don't want to be late for
your first day of work, do you?"
Andy shook his head as he replied with a smile, "No, I wouldn't want
that."
Serena then drove Andy back to Claire's. She let him out and wished him
good luck. He thanked her and went inside after pausing to let a Carhop
pass him on her way to a customer's car.
Keri was working again and told Andy to get ready in the backroom. He
did so and put on the white roller-skates after he took of his shoes and
put them on the side alongside the other waitresses' shoes and
pocketbooks.
Andy skated out of the backroom and out the diner's front door. He
waited by the pickup window for the first meal he was to deliver.
When he saw the order come to the window, Andy picked it up and skated
to the waiting car. Andy felt the slight breeze going up the skirt of
his dress as he rolled to the car. It made him feel a little cold as he
rolled up to the car. He was happy to be wearing pantyhose, which he
felt were at least keeping him a little warmer than he would have
otherwise been.
The older man in the car smiled at Andy as he took the bag from Andy's
hand. Andy smiled back and said, "Here you are, sir."
"Thank you, miss," the man replied. As Andy rolled back to the pickup
window, he turned back towards the man and caught him checking out his
legs.
While Andy was a little disturbed by the fact that he was being ogled by
a man, he could not help but be a little turned on by the fact. Andy
liked feeling desirable, even if he had no interest in the person that
desired him.
The feeling of desirability that Andy felt was not the only source of
his pleasure during his shift. Even though Andy's legs got a little
tired as the shift when on, he could not help but continually be aroused
by the feeling of his pantyhose on his smooth legs. It embarrassed Andy
to some extent. Even though he was tucked away, Andy was not sure if his
member might end up poking out at the back of his dress. That fear did
little to calm him down. Andy did not know why, but the potential of
that exposure excited him as well.
However, Andy was confident that no one would be able to discover his
true sex. As he went from car to car delivering orders, he never got a
suspicious look. The patrons just smiled at him and took their food. A
few gave him some suggestive looks, but Andy continued to revel in that
as continued proof that he had an unambiguously feminine appearance.
Andy's certainty came to an end when he recognized a patron he was
handing an order to. The patron was a fellow student at his high school.
The classmate was there with his girlfriend. Andy pretended to not
recognize them as he started to shake. He skated away from them, looked
back and realized that they had not realized who he really was.
Andy felt at ease as they pulled out of the lot, not bothering to even
give him a look as they left. He was aroused by the fact that he had
passed as a girl with people he knew, but he was also aware that he
could not risk bringing a meal to another familiar face. Andy knew that
he would have to be on the look out for those people. He decided that he
would have to pretend tie his roller-skate or fake an injury to make
sure that he did not bring food to those he knew.
As his shift went on, Andy heard his first come-on as a girl. Andy
peered into the car stuffed with five teenage boys as the driver told
Andy that he had pretty legs.
Andy blushed at the complement and thanked him.
"Oh, she's got a smoky voice," a boy in the back seat said.
The driver's eyebrows rose for a second as he nodded to the boy with a
smile. The driver then asked, "Are you a parking ticket, because you've
got fine written all over you?"
Andy rolled his eyes at the driver as he handed him his bags of food.
Andy then turned and went to roll away, but the driver cried out, "Don't
be like that, baby. It's just that you're so fine you make me stutter,
wha-wha-what's your name?"
Andy shook his head with a smile and said, "Are the patron saint of bad
pick up lines or something?"
"No, baby. My lines are rock solid just like me," the driver answered.
Andy skated back to the window and did not leave it until the boy drove
his car out of the parking lot. Another carhop smirked at Andy as she
saw the boys leave and said, "You handled that better than me. I
would've thrown that dick's drink in his face."
Andy smirked and went back to work. He delivered a few more meals
without issue.
Midway through his shift, Andy went on break. He had ordered food from
the diner and took it into the backroom to eat. After he finished, he
came back out and started the second half of his shift.
Not long after that, Serena pulled into the parking lot. Andy smirked at
her as he saw her pull up. She placed an order and waited for one of the
carhops to bring it. Andy pretended his skate had become untied so that
he could time it to make sure that he took her order over.
Andy picked up Serena's order and skated over to Serena's car. She
smirked at him and said, "Looking good, doll."
"I bet you say that to all the girls," Andy replied as smile came upon
his face.
"I think you're the prettiest girl out here," Serena responded.
"Well, there's only two other carhops on duty. It's a small field of
competition," Andy countered.
"Just take the complement, bitch," Serena retorted with a smirk.
"I'm the bitch, now, Serena?" Andy asked as he leaned in towards her car
as she took the meal from his hand.
"You're my bitch," Serena answered in a coo.
Andy stared down at his carhop uniform and felt that he could not deny
that at that moment. He nodded in response and said, "Well, remember,
babe, you're mine everyday for a week because of this."
Serena grinned and said, "I'm looking forward to it."
They talked a little longer before Serena pulled out of the diner's
parking lot. Andy then skated back to the pickup window.
Unknown to Andy, Lauren was standing within earshot of Serena's car
while she was smoking a cigarette. She heard Andy call her Serena and
noticed his apparent rapport with the girl. She realized that they were
exchanging loving looks. Serena began to realize that something about
Andy's claimed identity was not adding up.
She walked inside wondering what was going on. That's when she saw a
girl say to another girl, "Isn't that Serena Davis over there?"
"Where?" The other patron responded.
"Over there? I think that's her car."
Lauren realized that they were talking about the girl Andy was talking
to in the car and not her carhop. She walked over to the table and asked
how the girls knew Serena. They explained that they used to be friends
with her when they danced together at a dance studio when they were
younger and occasionally saw each other through a mutual friend. Lauren
gave the girls the address Andy had given her on his application. The
girls said that was where Serena lived. Lauren asked, "Do you recognize
the carhop out there with her?"
They shook their heads and one girl answered, "She looks like she might
be another girl from our dance class, but I'm not sure."
Lauren grinned and told the girls to enjoy their meals. She then walked
towards her office with an ear to ear grin upon her face. She could not
wait to talk to Andy when she got a chance.
As Andy's shift ended, Lauren called him into her office. Andy wondered
if he had done anything wrong. He did not really care if he did because
he planned to quit after he picked up his stuff from the backroom.
Lauren told Andy to take a seat. She smiled and said, "Serena, I've
discovered something about you, I find most intriguing."
"What's that?" Andy asked as he started to wonder if his disguise was
not as convincing as he thought.
"Well, I overheard you talking with this girl a few hours ago."
"Oh?" Andy replied as he began to sweat.
"Yes, apparently, she's known as Serena too."
"Lot's of girls are," Andy responded.
"That's true, but when I heard a patron point to her and say "There's
Serena Davis". That's the same name as you so I kind of got suspicious
about why you were so chummy with her as you brought her meal."
Andy started to shake. Lauren leaned towards and said, "I went and
looked up the address you gave, and then I went over and asked the girl
if the Serena Davis she had seen lived where you said you did. And do
you know what she said?"
Andy shook his head.
Lauren replied, "She said she was. So let's cut the crap. You're not
Serena Davis are you, dear?"
"No, I'm not," Andy admitted.
"You're Andy Iverson, aren't you?"
"How did you know that?" Andy shrieked.
"I went through your pocketbook dear. I found your ID."
"That's got to be illegal."
"Maybe it is, but you know what is illegal, my dear boy? Giving a false
name on an application. You stole Serena Davis's identity."
"No. I had her permission. I didn't steal it."
"Maybe you didn't, but you still passed yourself as someone you're not.
That's a crime in this state. We take this stuff very seriously here,
boy."
"It's not like that."
"Well, you can tell it to the police when they arrive. Oh, by the way, I
think your cellmates in lockup are going to love you having a boy with
legs like yours overnight."
"Please don't call the cops," Andy begged.
Lauren smirked and said, "Maybe we can work something out."
"You name it. I'll do it," Andy said in haste.
"Good. I want you to keep working here."
"Like this," Andy said as he pointed to his dress.
"Of course, we can't have a carhop looking any different from the
others. We have a regional brand to maintain."
"Why?" Andy asked.
"I know how spoiled kids from your neighborhood are, Andy. I think a
little hard work in a dress will do you some good. It might teach you
something about the real world."
"That's why you want me to do this?"
"Well, that and I was toyed with by a rich boy from your town not unlike
you. He treated me like trash because I wasn't rich; I guess I just want
to get my revenge on one of you."
"I'm not like that."
"All of you up there are like that. You like to toy with us poor people
and throw us out when you've used up."
Andy knew there was no point in fighting her. He figured he could just
leave and never come back and get away with it. It would be just be he
said she said if she did not call the cops then, he figured.
Andy replied, "Okay, you got me. I'll do it."
"Wonderful," Lauren replied before she pulled out a camera and took a
few pictures.
"What are you doing?" Andy asked.
"Getting evidence, Andy. I've learned you can't pin anything on a guy
like you unless you've got concrete evidence."
"You think that's enough to get the cops to prosecute me with?"
"Oh, no, Andy. I think it's enough to send them to your parents,
anonymously pointing out how you worked as a carhop."
Andy froze as he thought about his mother finding out what he had done.
He would be embarrassed if she saw him dressed as a female. He looked at
Lauren and asked, "When's my next shift?"
"Tomorrow at four again. Don't be late, or I'll send the pictures."
Andy nodded and headed out her door. He went into the backroom and took
off his roller-skates. He put his sneakers back on and picked up his
purse. He checked its contents to make sure Lauren had not stolen
anything. After that, he headed out into the parking lot to wait for
Serena to pick him up.
She came by a few minutes later and saw his dejected appearance. As she
pulled out of the parking lot, Serena asked, "What happened?"
Andy explained what had occurred. Serena was rendered silent by the
news. She pulled into an empty parking lot where Andy could change and
take off his makeup. As she stopped the car, she looked at Andy and
said, "I'm so sorry, Andy. I wouldn't have made this bet, if I knew this
would happen."
"I know. I'm not mad at you. I know you didn't know it was against the
law. It is what is though. I'll just have to get through this."
Serena nodded and said, "Don't worry, Andy. I'll be here to help you.
Whatever you need, just tell me."
Andy thanked her as he entered her backseat and took off his dress and
bra. He slipped on his male clothes over his pantyhose because he did
not want to strip naked in a parking lot. Serena joined him in the
backseat and removed the makeup from his face. They then put Andy's
uniform into a bag in the trunk and drove back to Serena's home.
Andy picked up his car, which was parked down the road, and he drove
home. His mother asked how Serena was. He said she was fine before he
told her that he would be spending the next night with her as well.
Andy's mother was not happy about him being out again with Serena during
the school week, but she decided not to prevent him from doing it.
-----------------------------------------------------------------------
Andy continued working four days a week at Claire's Diner for the
following two weeks. The shifts were all like his first one. The work
never really varied. He spent his time rolling around the parking lot
trying to make sure that his cover was not blown.
More than a few times, he had to fake injuries so that other waitresses
would bring meals to his friends and schoolmates' cars. None of them
ever noticed that he was among the waitresses, and Andy believed that
was because they had not gotten close to him.
Andy also did not like the fact that his employment had cut into his
time with Serena. While they maintained a sexual relationship, he knew
that Serena was more than willing to give herself to him more if he had
the time. Andy knew how much seeing him dressed turned her on, but he
was only able to have relations with her three days a week at most
because of his work restrictions.
Andy, however, found reasons to enjoy his job. He liked the constant
fear of exposure. The fact that he was not found out aroused him as
well. He was turned on by the fact that he was so passable. He also
loved the feeling of his clothing. Every time he put on his pantyhose,
Andy felt turned on by the sensations he felt on his legs. Andy also
enjoyed his paychecks. While they came in his girlfriend's name, Serena
cashed them for him and gave him the money. Andy liked having his own
source of money for the first time in his life, even though he failed to
spend a dime of it.
Andy also found himself growing increasingly comfortable working as a
carhop. He did not see any problem living part-time as a girl. Lauren
noticed this and decided to push him a little further. She called him
into her office to talk during a break on his shift.
Lauren smiled at Andy as he took a seat across from her desk. "Do you
know why I called you in here, Serena?" Lauren asked.
Andy shook his head before Lauren responded, "I have a new job for you
to do."
"What's that?" Andy asked, afraid of her answer.
"I need you to go to a school dance with my nephew."
"What? You can't be serious. You're taking this too far."
"Oh, I'm very serious, Serena. You will be going to his dance or else
I'll be calling the cops. It's entirely your choice though."
Andy pouted and asked, "When and where?"
"He goes to school in Springfield. You can meet him at my house there on
Friday."
"What do I have to do with him?"
"Nothing but show up looking pretty. I know you're good at that, dear.
The boy is dateless for the dance; I just want him to have a girl on his
arm for once to alleviate some abuse. He knows all about you, so don't
worry about him trying to score."
Andy felt a little relieved by her statement. He knew that while Lauren
was asking a lot from him, it was not as bad as getting arrested. He
nodded and said, "I'll be there. Just give me the address."
Lauren gave Andy her address. As he turned to walk out of the office,
she added, "Oh, and go get yourself a nice dress. I don't want my nephew
showing up to a school dance with some cheap looking like tart."
Andy nodded to her and walked out her office, sulking. He finished up
his shift and called Serena to tell her what had happened. She tried to
make him feel better about what he was going to do, but she knew it was
fruitless. They then made plans to go shopping the next day for heels
and possibly a dress.
-----------------------------------------------------------------------
Andy went to Serena's house the next day. It was one of Andy's days off
from work, so there were few time restrictions on their activities.
Serena let him into her house and opened up her closet doors. He tried
on all of Serena's dresses, but not one of them fit him correctly. She
only had a couple of dresses, and she wore them tighter than she wore
the rest of her clothing. Andy realized that he would have to buy a
dress as well as heels to go with them because he did not fit into any
of Serena's heeled shoes.
After realizing that Andy needed to buy a dress, Serena shrugged and
asked him where he wanted to shop for one. He told her to surprise him
as she began to get dressed in the clothes he had interviewed for his
carhop position in. Serena then drove him to the mall.
They entered the mall and headed into a boutique to find a dress for the
informal school dance. Serena looked through the racks with Andy. They
both knew their choices were limited because their selection had to be
one that did not show cleavage.
Andy selected a dress and showed it to Serena. It was a white long
sleeved dress. Serena shook her head and said, "You're too sloppy a
drinking and eater to wear white."
Andy asked, "What would you wear?"
Serena looked through the racks and selected a bright red, sweater
dress. Andy looked it over and thought about how he would look in it. It
had three-quarter sleeves, with a scoop neckline and a rouched,
drawstring bottom.
Andy thought the dress was very pretty, and it was with his price range.
He stepped into the changing room and slipped the dress on over his
head. He came out and showed the body hugging dress off to Serena.
Serena marveled at Andy's appearance. She loved how the dress showed off
his frame. Andy stared at Serena as he waited for her to say something.
Serena then broke her silence and said, "You look really hot in that."
"Thanks," Andy mumbled.
Serena shook her head and continued, "I really can't believe how good
that looks on you."
Andy blushed and said, "I guess I should pick out another dress then. I
don't want to give the boy the wrong idea."
"No. You have to get that dress," Serena exclaimed. Andy shrugged and
replied, "Fine."
Serena grinned at his acquiescence. She planned on him wearing that
dress many times in the future.
They then walked over to the shoe department. Andy and Serena searched
for the perfect pair of shoes to go with the dress. Andy settled on a
pair of closed toe, sling back, red heels. The shoes had a four inch
heel and a one inch platform. Serena shook her head as she looked at
them and said, "Those! They're cute, but they are going to kill you as
the night goes on."
Andy brushed aside her concern and decided to buy the shoes. He walked
up to the register with his purchases. He then paid the large amount in
cash as Serena looked on.
Andy felt a little bothered by the fact that he was spending virtually
all of his two paychecks on a dress and heels that he thought he would
never wear again. Serena laughed at his complaint and said, "A lot of
girls pay a fortune for dresses they only wear once."
"I'm not really like them," Andy reminded Serena.
Serena nodded slowly as the cashier gave Andy his receipt. Andy then
followed Serena out of the mall and to her car.
-----------------------------------------------------------------------
On the day of the dance, Andy prepared himself in Serena's house. Andy
first placed on a pair of black tights that Serena had bought for him.
He then placed on his bra before he slipped the dress over his head.
Serena watched Andy intently as he applied his makeup. She stared
longingly at the picture of femininity she saw emerging before her eyes.
As he finished, Serena walked towards him and began to style his hair.
She brushed out his hair and gave him a side ponytail. She pulled all of
his hair to one side and tied the hair up in a low ponytail with a small
elastic band. She then secured the other half of his hair with pins. As
she finished with his hair, Serena went and took a pair of earrings from
her jewelry box. She secured the dangling, gold, wire, tear drop
earrings into his ears as he watched her in the mirror.
Serena smiled down at him as she finished. She wanted him then for
herself. She was pained by the fact that he was going to be on someone
else's arm that night. Before he stood up, she whispered in Andy's ear,
"You look really hot, babe. My parents are out of town tonight, so be
prepared for me to tear that dress off of you when you come back later."
Andy smirked at her and picked up his heels and the small, black purse
Serena had filled for Andy while he was getting dressed. He carried the
heels towards her front door and put them on before he stepped outside.
Not wanting Serena to see him going on a date with a boy, he told her
that he would drive himself to Lauren's. Serena asked if he was sure,
and he replied that he was.
Andy took care to make sure that he followed every rule of the road he
was aware of as he drove to Lauren's home. He felt a surge of relief as
he pulled up in front of it without being pulled over by the police. He
stared at her house for a few moments before he got up the nerve to get
out of the car and walk up to her door.
Lauren opened the door as she saw Andy approaching the house. She stared
at him with a look of mild surprise before she let him in.
"You look good, Serena," Lauren said as she looked him over. Her sister,
Eve, seconded the opinion. Andy looked around for Eve's son, but Andy
did not see him. Lauren informed him that the boy was in the bathroom.
Vern came out of the bathroom a minute later. Andy glanced at the 5'9"
boy with pimples covering his face. Vern looked back at Andy and asked,
"This is the sissy you got me, Aunt Lauren?"
'This will be a long night', Andy thought to himself as he shook his
head at Vern's words.
"Yes, Vern. This is him. Quite pretty for a sissy, don't you think?"
"Whatever you say," Vern replied, not wanting to admit that he found
another boy attractive.
"Are you both ready to go?" Eve asked.
Vern and Andy responded with nods. Andy then followed Eve and Vern to
Eve's car. Vern got into the passenger's seat, and Andy sat in the
backseat of Eve's car. Eve drove them to the school, and she let them
out and told him that she would be back at 9 to pick them up.
Vern looked at the school door before he turned towards Andy and asked,
"Ready, pansy."
Andy sneered at him, prompting Vern to smile. He took Andy by the hand
and led him into the gymnasium that was being utilized for the dance.
Andy tried to look happy as Vern dragged him around the dance and
introduced him as his girlfriend from out of town. The boys and girls
that Vern talked to seemed surprised the girl actually existed. Andy was
happy that Vern never tried to demonstrate affection with him, but Andy
felt increasingly uncomfortable as he stood beside him. As he followed
Vern around the gym, Andy's feet began to bother him as the first hour
of the dance had past. He began to realize that he had made a terrible
mistake not listening to his girlfriend's advice on footwear.
He got a brief reprieve from standing when the food was brought out.
Vern and Andy went over and made themselves plates and sat at a table
with Vern's friends. Vern's friends asked Andy a number of questions
about himself. Andy made up lies to satisfy them. Vern smiled as his
friend's girlfriends complemented his date's appearance. That smile left
his face when one of Vern's male friends asked Andy, "What is a pretty
girl like you doing with him?"
Andy was silent as he tried to think of a reason given that Vern was not
rich and was not well endowed as far as he knew. Vern answered for Andy,
"It's because I'm charming, asshole!"
Andy nodded slowly and looked away from Vern's friends. Vern then put
his arm around Andy to advertise their relationship to onlookers. Andy
felt uncomfortable with Vern's arm around him, but he knew he was in no
position to say anything.
After they finished eating, Vern decided it was time to drag Andy onto
the dance floor to show off his moves to impress the ladies. They danced
together to some fast, dance songs. Their mutual lack of natural rhythm
made some people snicker around them. Andy was well aware that he was a
poor dancer, Vern was under the belief that his poorly timed, thrusting
dance motions were trendy. Andy struggled to keep a straight face as he
watched Vern dance. His amusement was the only source of pleasure for
him as his feet began to ache even more.
By the time a slow song came on, Andy's feet and ankles felt like they
were having pins shoved into them. Vern moved close to Andy as the song
began. Andy felt uncomfortable as he put his head on Vern's shoulder as
Vern's hand went around Andy's back.
"What do you think of the music?" Vern asked as they danced.
"Hang the DJ," Andy answered.
Vern smiled as his hand slid down to Andy's rear.
"A little higher," Andy responded with a sneer.
Vern's smirked and moved his hands up Andy's back. As the dance
continued, Andy felt something unusual grinding against him. He realized
what it was and glanced up at Vern appalled.
Vern blushed and frantically whispered, "It's the softness of your
dress, I swear. Please don't tell my mom."
Why Andy was prepared at that moment to announce that he was really a
man and that Vern was a sissy lover just to spite the boy, he decided
that he could use Vern's ill-timed erection to make the rest of the
night more palatable for him. Andy smirked at him when the song ended
and led him off the floor. Andy pulled him over to a corner and said,
"You don't touch me for the rest of the night, and I'll keep your little
boner problem to myself. Got it."
Vern nodded and said, "I promise, I won't touch you again. Just don't
tell my mother. She already thinks I'm weird. I'll never live this
down."
Andy nodded and excused himself to go to the bathroom. He headed for the
girl's room. He looked around as he waited on the line to use the
stalls. He never had been in a girl's bathroom in school before. He
looked at its pink colored walls and stalls, and he realized that it was
cleaner then the boys' bathrooms at his school.
After he finished in the bathroom, Andy returned to the dance. Vern kept
his promise as the dance continued. Andy watched the clock from the
table while he sat beside Vern as the minutes clicked away. The minute 9
o'clock came, Andy jumped to his aching feet and rushed for the exit
with Vern.
He got into Eve's waiting car, and he felt relieved the night had ended.
Eve asked how the dance was, and Vern gave the response as Andy took off
his heels and massaged his feet in the back of Eve's car.
Eve dropped Andy off at Lauren's. She was waiting for him when they
arrived. She smirked at him through the window as Eve and Vern left.
Andy put his head down and got into his car. He drove to Serena's home
slowly. He figured the last thing he needed was to be pulled over after
the night he had had.
He pulled up in front of Serena's house and walked up to her door.
Serena met him at the door dressed in lingerie. Andy felt slightly
better about the night as he followed Serena to her room. Serena was
then true to her word. She pulled off his dress, pulled down his tights
and made love to him.
-----------------------------------------------------------------------
The next day, Andy went back to work at Claire's Diner. As he worked, he
thought about the night before. As much as he hated how attractive he
was to men, he was happy about how it made his girlfriend feel. She had
given him the best sex of his life the night before. As he thought about
how much he loved the feeling of his feminine clothes and how they
seemed to increase Serena's sex drive, he figured that living as a girl
part-time was worth the occasional pain of heels and the looks he got
from men.
As Andy brought a meal out to a car with those distracting thoughts in
his brain, he heard a familiar voice. "Andy," he heard his mother shriek
from the car he was standing next to.
He quickly looked around to make sure that no one had heard his mother's
voice. When he realized that no one seemed to, he turned back towards
his seething mother.
"Mom, I can explain," Andy said.
"Explain what? How you kept that you got job from me? How you must have
been lying about where you've been going? Or about why you're dressed up
like male eye candy?" Isabelle asked her son.
"Yes, mom. I can explain it all. Just listen...."
"I'll listen when you get home," Isabelle interjected as she ripped the
bag out of Andy's hands and pulled out of her parking spot as fast as
she could.
Andy skated back towards the building that slow workday with a slack
jaw. He then saw Lauren smiling at him as he skated towards her. She
walked towards him and put up her hand. She smiled and said, "I see
mommy found about you."
"Yes," Andy replied as he hung his head.
"Well, I think you've been punished enough."
"What do you mean?"
"I mean, you're fired without cause. We just don't have enough shifts
for everyone we hired, and you're the most logical choice to let go
given your initial deceit, Serena. Give back the skates, you can keep
the uniforms."
Andy nodded as he went inside and took off his skates. He put on his
sneakers and collected his belongings. He then called his girlfriend to
pick him up. Serena came down right away and brought him back to her
place so he could pick up his car. Serena offered to let him change back
into his male clothes inside, but he explained to her that how he was
dressed no longer mattered.
As Andy walked towards his car, he began to feel uneasy about what
awaited him at home. He figured that his mother was going to kill him.
The only thing that helped ease his nerves was the fact that Serena had
promised to follow him home to be there when he talked with his mother.
Andy was also unsure of how he felt about losing his job. He enjoyed
working there, even though he constantly feared exposure. That was part
of the thrill of the job for him though. He liked the forbidden aspect
of what he was doing almost as much as he enjoyed the feeling of his
feminine clothes and staring at his girlish appearance in the mirror.
Serena followed Andy out the door as he left to go home. She followed a
car length behind him as he drove towards his house. She parked in front
of his house as he came to a stop in the driveway.
Andy waited for her to reach him before he took a step towards the
house. He did not care that he was standing in his driveway in a dress.
The significance of his cross-dressing seemed to be gone for him. He
took Serena's hand and walked up to the door and went inside. He found
his mother waiting for him in the living room.
Isabelle looked at her son and Serena and said, "Come in here and
explain yourself, young man."
Serena put her hand on Andy's shoulder as he walked over towards his
mother. He took a seat beside her and told her everything. When he
finished, his mother shook her head and told him, "You're an idiot!
Blackmail is just as illegal as fraud. You didn't have to go on that
date."
Andy was a little surprised that she did not seem upset about his cross-
dressing. He asked, "You're not upset about the fact that I was working
in a dress?"
Isabelle shrieked, "I'm very upset with you, Andrew. I'm upset that you
lied to me. I always felt we had an open relationship. I never
discouraged you about anything. I never said cut your hair. I never told
you to try to bulk up. All I ever did was encourage you to come to me
with anything."
"I know, mom, sorry," Andy responded as he realized how angry she was at
him given her use of his given name.
"You should be. You could have come to me with this. I could have gotten
you out of Claire's in a second if you had come to me. I can't believe
that you kept it from me. We've always had an open relationship with
each other. I can't fathom why you felt that this had to be the time to
end that."
Andy sat silently. Isabelle eyes then drifted to Serena. She was sure
that Serena was the reason that her son had become more secretive. As
nice as she thought Serena was, Isabelle did not want to look at her at
the moment. Serena realized this and told Andy that she had to go and
would talk to him later.
Serena kissed Andy on the cheek as she went to leave the house. With
Serena gone, Andy clasped his mother's hands and apologized for keeping
his job and cross-dressing a secret from her.
Isabelle smiled down at her son and put her arm around him. She then
whispered, "I forgive you, Andy."
Andy was relieved to hear her not refer to him by his given name. He
wondered if she would not hold it against him, but Isabelle then added,
"Now, go get yourself ready for a day of shopping with mom."
"What?" Andy asked as his mother pointed to a bag in the kitchen that
was visible from the couch.
Andy looked at his mother and asked, "What's in the bag?"
"Your punishment clothes dear."
"Punishment?" Andy asked.
"Oh, yes. I can't have you thinking that you can sneak around and not
have any consequences for your actions."
"What do you have in mind?" Andy asked as he walked towards the kitchen
and saw that the bag was from Guess.
Isabelle answered, "Well, I always wanted a daughter, and after seeing
you in your carhop uniform, I just couldn't help myself."
"What did you do?" Andy inquired as he began to breathe faster.
"I just got you a few little things that will enable you to give me the
part-time daughter I want."
"Part-time daughter?"
"Oh, yes, dear. I think you're going to better than the real thing too.
I can shop with you and dress you up, and I won't have to deal with you
PMSing or getting pregnant. You can give me all the benefits of having a
daughter with none of the burdens."
Andy started to shake as he wondered if his male life as he knew it was
coming to end. He knew that he would still be dressing around his
girlfriend. It now seemed to him that his mother intended to make him
her doll as well for entirely different reasons.
Andy hesitantly walked over to the bag that rested on the kitchen
counter. He put his right hand into the bag and looked inside. He
started to sweat a little as he saw the miniskirt with a sheer, three
layered, ruffle bottom. The primarily black skirt was decorated with a
floral print of pink, white and yellow flowers. As Andy picked it up and
looked at it, his mother remarked, "I knew that was perfect for you
after I saw your legs in your pantyhose, sweetie. You've got legs that
practically require a skirt like that."
Although his mother's complement made him feel slightly better about
himself, the hemline was shorter than his carhop dress's. As he gauged
its length, he realized that its hemline would fall only midway down his
thighs. He knew that he would feel exposed wearing it. Andy knew,
however, that airing out his objections would not make his life any
easier. Thus, he kept his mouth shut as he placed the skirt down on the
counter and put his hand back into the bag to pull out the top that was
resting on a shoe box.
Andy looked over the grey, graphic t-shirt in his hand. It contained a
picture of a woman in a red corset who was surrounded by black stars.
The word 'guess' was written in big gold letters above the girl. The
shirt had cuffed sleeves, a scoop neckline and rhinestone and glitter
details. Andy was unhappy about the eye catching colors on the shirt,
but he knew that if his mother had taken it as far as she had, he might
end up wearing a red corset for a top himself if he complained about the
shirt.
He placed the shirt down on top of his skirt in silence before he pulled
out the shoe box. Andy opened the box up with trepidation. He feared
that his mother had purchased him sky high heels. He remembered the pain
he felt at the dance and figured he was going to experience it again.
Andy felt a wave of relief pour over him as he looked at its contents.
The box contained a pair of brown, flat sandals with faceted crystal
detail on the braided, black thong straps. He was relieved that she had
purchased him footwear that he would have no trouble walking in.
Andy also noticed that box also contained a smaller box that had stuck
in between the sandals. He took out the small box and opened it. He
found a pair of rhinestone covered hoop earrings. He knew that they
would attract unwanted attention, but he figured that at least it was
the last of his mother's surprise clothing and accessories for him.
That was until she said, "I hope you like all my gifts for you."
"I do," Andy lied.
"Great because I've got two more for you."
"Oh, wonderful," Andy managed to say through a forced smile.
His mother walked past him and pulled another bag out from the dinning
room hutch. She reached in and handed Andy another small box. He
hesitantly took it from her. He wondered what other eye catching thing
she had bought for him to go out in public with.
He opened the box and saw the triple layer necklace in the box. He found
the silver toned chained necklace to be pretty, but he knew that its
three charms would attract further attention. The first charm was a
silver toned Guess logo, while the second was a large denim heart
surrounded by silver. It was the third charm that he knew would attract
the most attention though. It was a rhinestone decorated charm reading
'love.'
Andy thanked her as convincingly as he could. Isabelle laughed at his
attempt. She knew that he was not happy about having to wear anything
she had bought for him in public. She smiled though at the fact that he
had not resisted anything she had gotten him yet. It told her that he
truly wanted to make amends with her.
Isabelle then handed Andy his bag. Andy looked over the grey, crocodile
print, box handbag. It had silver tone hardware with a rhinestone
decorated charm and logo. Andy thanked her and went and emptied the bag
he borrowed from Serena into the bag his mother had bought for him.
Andy then looked silently over his new feminine possessions for a
minute. Isabelle broke his stupor and said, "Well, go get dressed,
Faith."
"Faith?"
"Well, yes, Faith. I don't think you want me calling you Andy when were
in the mall, do you? I will if you'd like. I mean, Andy's girly sounding
enough, but I figured you wouldn't want to risk bystanders attaching the
name to your pretty face."
"That's okay. Faith's good, mom," Andy responded in haste.
"That's my girl. Now, go get dressed."
Andy nodded slowly and collected his new belongings. He carried them
into his room, took off Serena's earrings and stripped out of his carhop
uniform. He then placed on another pair of panties he got from Serena to
give himself extra support in the hope that his member would remain
tucked despite the absence of his control top pantyhose.
Andy then put on his skirt and top. He then took hold of the makeup and
went into the bathroom. He freshened up his makeup there and tied his
hair back in a to the side ponytail. After that, he went back into his
bedroom to put on his new earrings and necklace. He then paused and
looked at himself in his full length mirror.
Andy looked at the teenage girl looking back at him. He looked like many
of his female classmates. He was not among the best looking ones, but he
would surely not be among the worst looking either.
Having seen himself dressed as a girl before, he was not that surprised.
He knew that he was passable the moment that he first saw himself after
Serena made him over. However, he had never worn anything as flattering
yet casual as the clothes his mother had bought. Andy realized that he
might be better looking than he initially thought. When he saw himself
in his carhop uniform, a dress or in women's jeans, he thought he looked
average. However, with the short skirt showing off his legs and the
tight shirt showing off his slender upper body, he felt that he looked
better than the average girl.
He smiled and said to himself, "I hope Serena's not at the mall or else
she might get jealous."
Andy caught himself and shook his head as he thought, 'I can't keep
thinking things like that. I might fall in love with myself if I do.'
A sudden thought then entered Andy's mind. He wondered if his mother
planned to expose him as a cross-dresser at the mall.
Andy shook his head as he continued to think about his mother's possible
plans. As he checked his makeup and his hair, Andy continued to wonder
if going shopping with her was simply her punishment or whether she was
going to do something else to him. He went over to his bed and picked up
the handbag his mother had left there for him. He placed the makeup she
gave him into it. He ran his tongue over his lip gloss and brushed his
fingers through his ponytail a little before he took hold of his
sandals. Andy then slid his feet into his sandals before he turned and
exited his bedroom.
Isabelle watched as her son walked towards her dressed in the clothes
she had purchased him. She smirked at how feminine he looked. She was
certain that he made a better looking girl than he did a boy.
Immediately after she reached that conclusion, she tried to pretend to
herself that she had not thought it. However, she quickly realized that
as long as she saw her son wearing female clothes, she would not be able
to forget it.
As he came to stop in front of her, Isabelle said, "You look wonderful,
Faith."
"Thanks, Mom," Andy replied in a low voice.
"I really mean it. Look at you. If I didn't know, I wouldn't be able to
tell. Wow. I bet Serena would die to look..."
"Serena would what mom?" Andy asked with raised eyebrows.
"Nothing, dear. Are you ready to go?"
Andy shrugged and said, "Ready as I'll ever be, I guess."
Isabelle grinned at her son as she grabbed his hand and led him out to
her car. Isabelle drove them to a nearby mall. After she parked the car,
she led him inside. Andy followed his mother as she walked into a Neiman
Marcus.
Isabelle led Andy over to the trousers. He watched as she perused the
racks for something that caught her interest. Suddenly she stopped and
took out a pair of Italian, white wide-leg trousers.
Andy caught sight of the price tag, and his eyes nearly bugged out. 'No
wonder, dad used to complain about your shopping trips', Andy thought.
His mother asked, "What do you think, Faith?"
Feeling that there was no risk of embarrassment given his appearance,
Andy responded, "They're nice looking. What are they linen?"
Isabelle nodded before Andy continued, "They've got some nice detailing
around the waist."
"Yes, they're pleated dear."
"They look nice and look like they'll be comfortable on you."
"I think so too, dear. I'm definitely going to try these on later."
Andy smiled at his mother's response. While he felt a little strange
giving his opinion on a pair of pants for his mother, he was also elated
to see that his mother actually was listening to his opinion on them. He
realized that he was enjoying grading the pants in a way that he had
never experienced when he selected his own male clothing.
Isabelle decided she would try on the pants and headed over towards a
rack of blouses to find a top to go with the pants. Andy watched as his
mother thumbed through the rack before she pulled out an