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Makeup Mistake
By Charissa Michelle
Copyright 2000
John sat at his mother's vanity for the hundredth time. At 10 he had
dressed as a girl for Halloween. The love of the clothes and the look stuck with
him. He ate and kept himself in shape, making sure he did not develop muscles
and overly noticeable masculine traits. He had snuck into his parents room and
played with his mothers makeup and clothing ever since.
He didn't really want to be a girl; he just liked the feelings the clothes
gave him. This time he wanted to see if he could really pass as a girl his own
age. He had even gone to the length of making out a list of things he needed,
writing them in a curly fluid feminine style. This was going to be a special
time. His mother had just gotten some new makeup that week. She looked better
then ever with it and he wanted to try it out for himself.
He took the notes, borrowing his mother's car the evening after his
parents left for the weekend and headed to the mall. The first stop was the shoe
store where he picked up a pair of black 3-inch heels and a pair of light
gray/lavender 4-inch heels. Then he headed off to the jewelry store where he
purchased a pair of small sapphire studs. He returned the items to the car then
went to into Dillard's where he went to the ladies department. After a bit of
looking around a sales lady approached him.
"Can I help you," she asked?
"Um, yes. I don't really know what to get."
"What are you looking for?"
"My Mom gave me a list of things and the sizes. But they don't mean much
to me. She said to get help, but I'm a bit scared." He smiled a bit and
remembered in his scared state taking measurements of himself for the clothes.
He handed the slip of paper to the lady who looked it over.
"Well, you are in the wrong area, what you need is over here. You're
looking for the stuff in smaller sizes." She led him across the main path to the
smaller sizes.
"Do you know what the idea of the stuff she is looking for?"
"Mom said that the sales person, you, would know what to get. Its sort of
a special occasion."
"What occasion?"
"My sister just got a new job. The note explains it." He handed her the
note he made earlier that day. The lady read of the note and thought for a
second.
"Okay, I think I can help you then. She wants something casual, but able
to be worn in a business atmosphere. That's usual for a teen secretarial type
position. And specifically a satin or silk blouse." She took her time thinking
about what to get. "What color of hair does she have?"
"Uh, Sandy brown like mine, but down about 6 inches on her back. Almost
blonde really." His was about shoulder length tied back in a ponytail.
"Okay, what colors does she prefer?"
"I don't know. I never really paid attention to that."
"Well, I believe what would work is over here." She led him around a few
racks and then looked through the sizes of the light jackets. She handed him the
correct size and moved over and started going through matching skirts. She
picked out one of those and then a pair of matching slacks. He followed her all
the time while she was looking though silk blouses.
"Does she like lavender or blue better?"
"Uh." He thought for a second. "Probably purple, lavender that is"
"Okay, then it looks like we have what you need." She held the blouse
under the jacket and the skirt up to that. "What do you think?"
"It looks okay. I think my sister will like it. At least I hope she does.
Else all my embarrassment here was for nothing." He smiled again, becoming quite
red this time.
She just smiled and handed him the selections and guided him to the cash
register. After paying for it he looked at the sales lady, "Great, I have to use
some of my own money for this too. Mom owes me for this one."
She looked back and grinned, "At least you have enough here for what you
need now and wont have to come back. And you can bring the receipt back for free
alteration within the next 2 weeks."
He nodded and paid her. He took the clothing to the car and returned one
last time to the mall. This time he headed directly to Victoria's Secret; the
place he dreaded. He stepped in and went directly to the desk for help.
"May I help you sir."
"Yes, please." He handed the second slip of paper to the attractive young
lady. "I need to get this for my sister. This is the worst; I can't even believe
I let Mom talk me into doing this. Jessica, my sister graduated from high school
last month, she has a new job and to top it off she's going to a ball and Mom
wants to get her a present. Since Mom and Dad are going out of town for the
weekend I'm stuck with getting the stuff she needs."
"Okay. Well, we have all you need here. Do you know what color the gown
she will be wearing is?"
"Lavender I think. I'm assuming that's what she brought home last night."
"Okay, we can get matching lingerie." She proceeded to pick out a lavender
panty and bra set in the 'Desire with Dream Angle Embroidery in a Full Coverage
style'. She then proceeded to get a pair of Nude thigh-high nylons with a
lavender lace top.
"Is there anything else that you need?"
"Uh, yeah, I need to get some white satin panties also."
"Okay. Same size?" She headed off to the satin selection.
"Yes."
"They are on sale, 3 for $21. What style, High Cut Briefs, Bikini, String
Bikini?"
"One of each."
"Would you like a matching bra with that?"
"I guess, I wasn't told to but who knows."
"Okay. Full coverage, in the 36C as well?"
"Yeah."
"Is that all then?"
"Yeah," he said again waiting to get out of there.
She took the items to the counter.
"Look, don't be too embarrassed, a lot of guys come in here to get
lingerie for their wives or girlfriends and once in a while for their sisters or
another family member, even for themselves. Its not that bad is it?"
He looked at her nearly straight-faced. "I guess not, it's just really
different."
"I understand..." She paused for a minute. "The panties are for you aren't
they?"
He bowed his head and nodded.
"That's okay. Tell you what why don't we take back the sting bikini since
you won't be able to wear that comfortably and get something else."
He nodded and followed her. "So, are the other items for your sister or
you?"
"They are for my sister, I told you the truth, but it's just they are so
nice."
She grinned and continued to pick out items for him. "Do you want the bra
then also?"
He shrugged and looked around. No one was looking at them in the near
empty store. "I don't really have the figure for it; I'm not really a cross
dresser."
She smiled again. "Well tell you what, let's get you two other styles to
match the panties," she lowered her voice to a whisper, "on the house."
He looked at her quizzically and shrugged again.
After about five minutes she helped him pick out 3 other colors, black,
lavender and pink, all in satin and returned to the counter. She rang up the
items separately on two different tickets. She acted as if ringing up three of
the four bras, seamless full coverage, seamless demi, and full coverage racer
back styles, though the register never rang up the items. She had also convinced
him to get a satin chemise in white.
"If you want to come back I work evenings Thursday through Sunday, and
afternoons on Wednesdays. Ill help you with whatever you need." She handed him
the bag and smiled again.
He looked at her directly in the eye and smiled again. "Thanks... For
everything."
"No problem," she smiled with a twinkle in her eye and watched him leave
the store.
He took those out to the car and left the mall heading to a premier dress
shop. He wanted to get a nice dress also for his occasion. When he stopped in
the parking lot he opened the glove compartment again and got out more money. He
thought it was a good time to spend part of his inheritance, just for him. At
least use it to have a little fun.
He walked up to the dress shop and stood at the door for a while. He knew
what dress he wanted and what size. He just hoped he had enough money and they
had it in his size. After a few seconds he got up enough nerve and walked in. He
looked around for the dress that was in the window the week before. It was a
halter top, mid calf, lavender satin dress with a slit to mid thigh. He didn't
see it off hand and a lady came up to him.
"Sir, may I help you find something."
"Uh, yes. My girlfriend has been dying for a dress you had in the window
last week I think. I just got paid, and I have tickets to the Daily Charity Ball
next week. I wanted to get her something to wear for it. She loved the dress so
much I figured I would come here to get it for her."
"Which dress was that?"
"Lavender one that is held up by the neck." He played innocent so she
wouldn't get a clue.
"Oh yes, we have that one. What size?"
"A ten. And let me tell you that was not easy to find out."
The lady chuckled a little and guided him toward the dress. She picked up
a size 10 and held it up. "Is this the one?"
"Yes it is. Thank you."
"Well, we also have another in the same color and general style that would
be a little better for the ball if you would like to look at it."
"Sure, why not? But is it much more expensive?"
"About $15."
"In that case lead the way."
She held up the same dress but had a little lace and glitter on it, not
much, but it looked sexier.
He gazed at it a minute and nodded. "Yeah, your right, that would be a
little better. I'll take it. And if she doesn't like it she can come in with me
and we can exchange it for the other dress. Can you hold that for a couple of
days just in case, so it's not sold?"
"Yes we can, and I'd be happy to do that."
"Great, you sure made my day."
"Your welcome sir." She paused as she rang up the damages. "That will be
$212.52 sir."
He handed her $220 and received the change. He took the dress out to the
car and proceeded to make his way home.
As he was driving past the K-Mart he decided to stop in and pick up a few
things. Before he got out of the car he realized that he had just spent over
$650 on women's clothing. 'I am a cross-dresser.' he thought and shook his head
in shame.
He originally stopped to get some socks and stuff but instead bought 2
pair of women's jeans in his size, three blouses, a summer dress, a package of
cotton panties and some jewelry. But the time he left he spent almost $200.
He got home and took all his purchases inside. He didn't have a clue what
he was going to do with all the stuff he had bought. The more he though the less
he cared. It was his weekend.
He carried all his purchases to his bed and unpacked them. He took a
shower, shaving his legs and scented himself in his Mom's new body powder, then
put on the lavender bra and panty Desire set, inserting breast forms. He went
over to his mother's vanity and sat down.
It took John a few minutes to go over everything that had happened that
afternoon. He looked in the mirror and began to brush out his hair. He picked up
the sapphire studs from his first purchases and pierced both his ears, cleaning
them with alcohol and applying Neosporin to each ear before he did it. He then
took his time applying foundation, eyeliner, shadow, blush, mascara and lipstick
almost expertly. He didn't really look at himself then.
He got up from the vanity and undid the plastic covered suit set. He
carefully put on a pair of his mothers black nylons, then the blouse, skirt and
jacket. He looked at the mirror and was definitely astounded. He looked good,
but his bust needed padding and his hair a little work.
He went into the bathroom and plugged in his mothers curling iron, and
began to unroll toilet paper, stuffing it into his bra. His nipples itched a
little after he put the padding in but he paid no attention to it. He also
didn't notice the slight change in his facial features. After the curling iron
was warm he put the ends of his hair in it and curled the bottom up in feminine
style that he had done many times before, using hairspray to keep it in place.
When he finally checked the full-length mirror, he definitely liked what
he saw. After a few minutes of prancing around he put on the black heels and
walked a bit. He had practiced in his sisters many times before when he was
younger. This time he liked what he saw.
He scratched at his chest again still thinking nothing of it. He decided
to try on the dress he so much wanted. After about 5 minutes to carefully change
he had the dress on and the 4-inch heels. He noticed the dress fit quite well.
Checking his hips and waist, he looked quite decent in the dress.
Again he scratched his chest but felt a little hard knob on his nipple and
a tingling sensation through the toilet paper. He admired himself in the mirror.
As he watched his hips seemed to widen, his waist shrank and his general body
began soften. His nipples then began to itch again, this time worse than before
and he started to feel a tingle in his genitalia.
He watched more intently at the changes happening. He couldn't believe it.
His face had become a bit younger, and feminine. His whole body seemed to be
conforming to his mental version of his female self. It was gradual, and barely
noticeable, however if you checked every minute or so you could see changes.
He started to get scared when he felt his bra get tight from the expansion
of his chest. He quickly pulled off the dress, panties and bra, staring at
himself in the mirror. He was changing for sure. He had small budding breasts,
his penis had shrunk to what it was when he was 8, his hips had grown and waist
became smaller. There was nothing he could do. He sat down on the bed and cried.
After nearly half hour of crying and watching himself change he finally
went to bed in his own room after putting on the chemise he had purchased that
day. He slipped into bed rolled over and cried himself to sleep.
Over night his body matured from the attractive young girl, to a beautiful
young woman. John, now Jessica woke up with a need to use the restroom. At first
she didn't noticed anything, thinking the night before was only a dream. It only
took her a few seconds to realize it wasn't. He got up and ran for the bathroom,
his breasts jiggling as he ran, his first feeling of what it was like to have
breasts.
She reached the bathroom and quickly lifted the lid and realized that she
had to sit. Taking a time to lift the chemise off she sat down and relieved
herself for the first time as a girl.
She decided to take a shower in hopes she would feel better. The warm
water ran over her sensitive body relieving tension that had built up over the
last hours since her change. She washed all over her body, taking great care of
feel everything.
After 30 minutes and 2 orgasms later she washed her hair and dried off.
Taking her time she actually enjoyed the experiences and ecstasy aftermath.
She went to her bedroom and opened up the bag from Victoria's Secret,
pulling out a black satin full coverage bra and bikini panty set. She took her
time to comfortably fit her breasts into the cups of the bra and to slide the
silky panty up her legs; pulling up the black nylons she had worn the night
before.
After admiring herself in the mirror for what could have been ages, though
it was only ten minutes, Jessica picked up the skirt he had bought and pulled it
up to his waist. He picked up the lavender blouse admired it some and put it on.
After thinking about it a minute, she picked up the jacket and swung it
across her shoulders and again looked at herself in the mirror. She liked the
look, and liked herself. She didn't really know why, but she liked being a girl
even though he never really wanted to be a she, at least that's what she
thought.
A half hour later she left the house and headed to a strip mall a couple
miles down the road. Before she left she called her mothers hairdresser for an
appointment, requesting Michelle's services. He got an appointment for an hour
later. He made a stop at the ATM and took out $400 from his account. The balance
now read $1810.80.
She stepped out of his mother's car completely at ease and walked over to
a nice store he had been by a thousand times but never entered. By the time she
left she had purchased over $150 worth of clothing, which didn't end up being
much. She looked at the watch she borrowed from her mother; she had 5 minutes to
get to Michelle's.
He went inside the small salon going up to the receptionist's desk,
announcing her name. The lady nodded and said Michelle was just about done.
After about 10 minutes Michelle came over and got Jessica.
"So, what can I do for you today miss?"
"I need a new style. Something that looks good. I can never decide so I
will let you do what you think is best."
"Okay, if that's what you want, are you sure?"
"Yes, I'm definitely sure."
"Okay." Michelle looked over the attractive features of Jessica and then
turned the chair and leaned her over the washing bin. As she began to wash she
started up a conversation. "Are you any relation to Rebecca Donnalls, you look
much like her and her daughter Denise.
"Yes, I'm her other daughter," Jessica replied quietly.
Michelle looked at her curiously and then with a bit of surprise as what
happened dawned on her. "You're John aren't you?"
"I was until last night ma'am."
"Oh my, you got into your mothers makeup and bath items didn't you."
"Yes ma'am. Is that what did this to me?"
"That would be correct. Didn't she leave you a note not to use her new
stuff? I told her to do that. And yes, I knew you liked to dress up once in a
while." Then right into Jessica's ear, "I hear everything. It's the burden of
being a hairdresser but it's interesting."
Jessica grinned yet again with a bit embarrassed.
"Well, your stuck like this now. But you'll love it."
The conversation went on for over an hour while Michelle did Jessica's
hair. When she was finished Jessica's hair was a bit lighter with even more
blonde highlights, a 3/4 curl at the bottom around the neck and jaw line all
with a slight wave and parted in multiple places. She was beautiful, to say the
least. Michelle didn't charge her for the cut this time, being on the house
since she was a new girl.
Jessica took her time going back home, and decided to go to the mall to
get some more clothes. When she finally did make it back she had spent $200 more
at Victoria's Secret, and another $50 for 2 more pair of shoes.
She got home, bringing her packages to her room, returning to her mother's
bedroom to gaze at herself in the mirror again. She looked up and down at
herself and started crying again. She made her way to the chair at the vanity
and sat down, the makeup tears dripping from her face.
She picked up the foundation and read the label. 'Women's Beauty. For
magical beauty for you that will keep you young and vibrant for years.' He
dropped his head and shook it crying yet again. The emotions were definitely new
to her.
She noticed a piece of paper on the floor. She picked up the note left for
him by his mother that he hadn't noticed before. She opened and read it. 'Hon,
don't use this new makeup of mine. The other stuff is fine and is in the side
drawer. I really don't think you will like the results of my new stuff. And yes,
I know of your playing with my makeup. But please, don't use the new stuff. -
Love Mom.'
Jessica stood up, tears still dripping from her eyes though coming slower.
'Well, at least I won't have to hide my new clothes now.' she thought. 'And I
get to use makeup and wear all the nice clothes from now on. Maybe it's not so
bad.'
That was the last time she cried over his mistake, making him a her.
If only he had known to take off the makeup and wash the bath powder off
the changes would have quit.
Epilog
Jessica called her mother before she left about 3:00 in the afternoon on
Sunday. She told her mother what had happened and about the note. Later her
parents and little brother, soon to be mother, aunt, and sister walked in the
door to be met by Jessica in the lavender ball gown. Her mother hugged her and
took her upstairs. After an hour Jessica finally convinced her mother that she
liked who she was even if she was a bit emotional.
Life went on after getting all the paperwork finished for a new identity.
When summer came around, the next surprise arrival in the family occurred. By
the end of the year, there were only women living in the house. Each enjoyed
being a woman, but those are other stories.
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