itsmeganprincess:

Amber’s New Toy

By Meganprincess

There is nothing quite so annoying as a precocious child.
Amber was just that. Not really a child but close enough. At least in Jimmy’s
book. She was smart. She was talkative. She had long straight blonde hair and blazing
blue eyes. It was not hard to tell that she would be a real beauty very soon.
And now she had Jimmy completely under her bratty power. Here is how it
happened:

Jimmy was spending Christmas vacation at his best friend,
Brody’s, house. Brody’s mother and father agreed to take him in while his own
parents took a vacation to England. Every night Jimmy and Brody spent their
hours playing video games, only occasionally interrupted by Brody’s stupid
little sister, Amber. School was out for a few weeks and Christmas was looming.
Life was good. Until the morning that Jimmy woke up with a sore throat. It was
the day the whole family was going to drive to the big city a couple hours away
and finish shopping for presents. All except Amber who was staying the night at
one of her friend’s houses. That morning Brody’s mother took one look at Jimmy
and threatened to cancel the whole trip. But Jimmy felt bad and told them to go
ahead. He would be alright without them and would just stay in bed. And so, a
few hours later he was alone in the house. Maybe it was the cough medicine.
Maybe it was fate. Whatever the case, something directed his first tentative
steps into the forbidden region of Amber’s bedroom. Why was he here? He didn’t
know. Didn’t even like the brat. Jimmy didn’t have a sister of his own and had
never even had a girlfriend. Maybe he was just intrigued in some strange way
with the secret life of girls. And here that life was, confronting him with all
of its strange, mysterious power as he stood in the doorway and surveyed
Amber’s sanctuary. All pink walls, and flowery pictures, fluffy pillows, and
lacy bedspreads. Makeup table. Dresser. And the doorless closet just across. A
dress hanging in the front caught his attention and he walked toward the closet
without a thought. Up close it was white with a flowery design. He reached out
and touched it. So soft. So silky. So utterly FEMININE. He stroked the fabric
absent-mindedly. It had to be the cough syrup. He felt so strange. Felt so
COMPELLED. Like he was somebody else. Down came his pajama bottoms. Off came
his pajama top. He took the dress off of the little padded hanger. A moment
later it was on him. Amber’s pretty dress. He felt a thrill of excitement he
had never felt before. Had never even imagined. And then he took some steps out
of the closet and into the bedroom. The floating touch of the hem of the dainty
dress against the skin of knees electrified him. The slight pull of the silky
light fabric across his chest and on his shoulders sent pulses of unnamed joy
straight to his innermost depths. He walked the full-length mirror on the wall
and looked at himself. Eyeing his legs first and then checking out the dress
little by little up his body past his waist. He almost didn’t even dare to look
at his own face in the mirror. Would it be changed? As his eyes lifted to face
himself, he saw another face beside and behind his own. Amber!

There she stood in the doorway. Hands on her hips smiling as
she watched her big brother’s friend standing in her dress. She watched as he
tried to speak but stopped him before he could even get the first word out:

‘Like my pretty dress, Jimmy? It looks really cute on you.
Oh, don’t even try to take it off. I already got a great picture of you in it.
Should I send it to Brody?’

‘No! Please don’t, Amber. I’m sorry.’

‘Oh, don’t be sorry. It’s fine. I think it’s adorable how
much you like my pretty dress. Want me to help you?  I’m so glad Katy got sick and I came home
early now. This will be so fun!’

‘Help me? What do you mean?’

‘I mean help make you prettier. Are you going to be a good
little girl and cooperate or do I have to send this picture to my parents and
say you were in my room and you tried to perv on me when I got home? Hmm, sissy?
Anyway, I can tell you like it. You looked so happy when I was watching you.
You like feeling like a girl. It’s okay. There’s a boy at my school like you.
Maybe you could date him later.’

At this she giggled so hard she had to cover her mouth. But
seeing how confused and sad he looked, Amber relented.

‘Oh, I’m sorry Jimmy. I was really just kidding. You’re
probably not ready to date boys. Yet. Let’s just have some fun while my family
is gone and you can see if you like it. No one has to know. Okay?’

She was right. How did she know? He DID want this. At least
to try it. So he reluctantly agreed and it began with an excited clap of
Amber’s hands as she approached him.

‘Now first things first. We can’t keep calling you Jimmy,
can we? No. Jimmy is a guy’s name and you are a girl. How about Jenny? Or Jennifer?
It kinda suits you. Yes, your new name is Jennifer. Do you like it, Jennifer?
Does it make you feel pretty?’

He softly nodded his head. Not even aware that this was the
first sign or gesture of his new subservience to Amber.

‘You are going to be such a pretty girl, Jennifer! You are
wearing the dress I wore to the Easter dance last year. But you are missing
some important things. Let me help you take it off.’

Jimmy took a step backwards in fear but then remembered that
he had his boxers on underneath. He stood stock-still while Amber lifted the
dress up and over his head. She paid no attention to his discomfort and went
straight to her dresser while Jimmy looked on in growing shock.

‘Perfect! Yes. Here we go Jennifer. You can start with
these.’

What she held out to the frightened boy was a baby blue pair
of little satin panties with white lacy edges and matching ribbon at the center
of the top.

‘Don’t just gawk, Jennifer. It’s just underwear. Every girl
wears panties, so you will too. Now be a good girl and put them on. Now!’

And she stamped her foot for emphasis. Remembering the
incriminating pictures, Jimmy turned away from her and lowered his boxers
before easing the soft panties up his thighs.

‘Now turn around, Jennifer, and show me your pretty panties.
Aww! So perfect for you. It’s so funny making a high school boy obey me and
turning him into a little girl. Don’t look so embarrassed Jennifer. I’m not
THAT much younger than you. I will be in high school next year. I won’t tell
anyone about this as long as you obey me like a good girl. Understand,
princess? Say ‘yes maam’. Say it or I send the picture right now of you in my
pretty dress.’

Defeated and trying not to notice the satisfied smirk flit
across Amber’s face, Jimmy softly said:

‘Yes maam’

‘Good girl! Now put on this pretty little bra, Jennifer.
Hold your arms out.’

And he did. Then Amber had a good time at her victim’s
expense as he struggled to reach behind him and hook his bra for the first
time. She thought about coaching him and teaching him about how little girls
usually first learn by spinning their bra and hooking it in front but his sheer
nervousness was too delicious to forego. In a few minutes he stood before Amber
in matching bra and panties. And then she presented him with a pair of white
cotton pantyhose. Which were soon snuggly pulled up over his waist, trapping
him in his little girly panties.

‘Oh my God, Jennifer! You look prettier already. I am going
to dress you EXACTLY how I dressed for the dance. Here is your dress. Put it
on. That’s my good girl. Don’t worry about those pictures I just took of you in
your bra and panties. They are only for insurance in case you are a bad girl.’

As he stood in the white flowered dress once more, Amber
fussed and tugged at it until it sat just right on Jimmy. Once satisfied, she
went back into her closet and came out with a couple more things. First, she
had him step into a pair of black high heels. Three inches high only but tall
enough to cause Jimmy to wobble a little even in a standing position. Then she
handed him a matching black purse in shiny patent leather.

‘That’s for all of your makeup. Dresses don’t have pockets.
Just something a girl like you will have to get used to. You will wear it on
your shoulder for now. Now start walking, Jennifer. Good girl. Walk across the
room in your high heels with your purse. Small steps. Hold your shoulders back.
Yes, good girl. You want boys to notice your little boobs. Should I stuff your
bra? Do you want boobs? Good Jennifer! Just like that. Now wiggle your butt a
little as you walk. Maybe a cute boy will ask you to dance. Would you like
that? Pressing himself against you. Rubbing his hands up and down your girly
little body as you dance. Touching your ass through your dress. Maybe kissing
your neck?’

None of these teasing questions required an answer. They
were just designed to humiliate and insinuate. She felt her power over this
wimp growing by the minute.

Then she sat him down at her little makeup table. And turned
him into a pretty little girl. Teaching him how to dab on his foundation and
then blend it. Patting on a light layer of powder. Doing his eyeliner. Making
him match his eyeshadow with the flowers on his dress. Even making the
frightened boy apply his own mascara. As Jimmy looked at his transformed face
in the mirror, he saw Amber devilishly smiling at him over his shoulder and he
lowered his eyes in shame and confusion.

‘Aww! That is soooo cute, Jennifer. The way you bat your
eyelashes and act shy just like a little girl. Boys are going to love you. And
you’re blushing too!! So sweet. Maybe we don’t even need to put blush on your
cheeks? No. Bad idea. You need to learn to do your makeup. Here brush it on
your cheeks. Not too much. Perfect! Ready to do your hair, Jennifer? Since it’s
kinda long it should be fun and easy. I think you should wear it up. Let’s
see…’

After a few minutes and some light, carefree, mocking
humming from Amber, Jimmy’s hair was pulled up into a high ponytail and tied
off with a dangling length of white ribbon. Little strands were pulled in wisps
down at the sides to frame his face.

‘Now take off your heels, Jennifer. Time for you to put on
your polish. Toes and fingers, Jennifer. And look! I have the absolute perfect
color for you: it’s called ‘prissy pink sparkle’. Go ahead, Jennifer, coat it
softly on your little toenails. Soft, feminine strokes. So pretty. So girly. So
you.’

After his toenails and fingernails were prettily painted,
Amber had him apply a clear topcoat and then taught him to wave his fingers
around to help dry them quicker after taking pictures of him blowing on them
like a complete sissy first.

‘Okay Jennifer. Almost done. You have to finish your pretty
makeup now. Sit back down in front of your vanity mirror at your makeup table.
Here you go, princess. Your lipstick. Pretty frosty pink. Stroke it across your
lips. Good girl. So sweet. Here. Press your lips against this tissue. Make a
little kiss mark. This sets your lipstick. Now roll this shiny clear lip gloss
over your lipstick, Jennifer. It makes boys want to kiss you. And I know you
want that. Now, stand up, Jennifer. Time for your photoshoot….

End of part one

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Amber’s New Toy
sissy fiction by Meganprincess