Dress Punishment Stories
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Dress Punishment Stories
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The Crossdresser
Table of contents
Chapter 2: The Punishment/Enjoyment
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by JazzJennings
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your bestfriend is Jayla, you have been friends since 2 years. You get along very well with her and her family..except one of them.
name: bella
age: 14
Siblings: 2/broth...
Life 2.0: mostly sweet short M2F TG stories
The 30+ stories in this collection are short sweet vignettes with a transgender theme.
Mostly happy stories you can read in one sitting. Some feel like true stories whi...
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Welcome to The Crossdresser! A magnificent book filled with crossdressing short stories! If you PM me and tell me your Trans-story, it could be featured in this part!
# crossdressing
# dresses
# girlyboy
# secrets
# transgenders
Fred was paralyzed with fear. The one time he decided to go with his gut and wear a dress. It was like he was being punished for doing what he likes.
+
Fred's mother tried not to smile at first, but then she realized this was no joke. When Fred used to wear female clothing, he would take it from his mother's closet, or sister's. And that caused a few problems, and Fred's mother didn't want any more problems.
+
"Fred? You know that Christmas dress thing was a joke, right?" asks Fred's mom.
+
Fred nodded then said, "Yeah... I know. But I just wanted to wear this. I feel like I was supposed to wear dresses and other female clothing. I feel lik -" starts Fred, but his mother cuts him off with a mad tone to her voice.
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"Fred, I can't have my son wearing dresses and skipping around like a princess. But you have to have some punishment. I was meaning to ask you if you wanted to go mini golfing with me and your sister, but you have no choice no. I'm getting you a wig, and you're wearing my shoes. You're going to golfing like that" says Fred's mom.
1
Two hours later, I come out of my room with a wig that matched my hair. My mom also added lipstick, and other makeup. I kept the dress on and my mother made me wear her flats. My sister that was one year younger than me, (So 12), said, "I always wanted a bigger sister"
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"Shut up, brat. I had to shave my legs and arms because of this" I say.
+
"Ha, good thing your voice sounds like a girl," says my younger sister, Tessa.
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"Come on," says my mother, and we walk outside. I was so nervous, im not sure if I can do this. I walk out and the wind blows my dress to the side. The dress is really comfortable, though. I try to hurry to the car. I get in and then twenty minutes later we arrive at the place. "Can we not do this?" I ask, but my mom gets out. People are going to realize that there are no bumps on my chest and im going to get into some trouble. I get out of the car. We get our clubs and we start golfing. They enjoy it, but I dont. But being in the dress and finally getting to act like a girl was amazing. Maybe its not so bad. I need to talk about my mother sbout this before i hit puberty. I want to go on hormone blockers.
1
The subject of petticoat punishment, when naughty boys are dressed as
girls as a punishment, strikes a chord with me, because it brings back to me
what I can only describe as the petticoat punishment I had to endure when I
was at primary school in England during the 1950's. From time to time I have
heard this form of punishment referred to as 'cruel and unusual' in the
United States, and is, I believe, illegal there today. What a pity. The term
'cruel and unusual punishment' is a concept that only seems to exist in the
United States, and frankly, one that we in England regard as oversensitive.
Yet another difference between our two cultures I suppose.
Humiliation amongst one's peers as a robust form of punishment was widely
used and approved of in the United Kingdom when I was at primary school, as
a salutary (and in my case) most effective method of bringing naughty
children into line with no deleterious side effects whatsoever. And
certainly less physically painful than the cane on the backside for boys, or
a tawse (a Scottish strap) smartly applied on the outstretched hand for
girls.
However, my school's headmistress, Miss Wareham, was vehemently opposed
to corporal punishment, and forbade its use. That may sound lenient, but her
alternative was to any boy far worse than a short sharp application of the
cane on his backside. Miss Wareham preferred humiliation as a punishment,
and a list of her inventive penalties for misbehaviour were pinned up on
every notice board so that there could be no plea of ignorance if you were
caught committing some misdemeanour or other. As I recollect, the list of
penalties went something like this:
Talking or being disruptive in class : The culprit had a baby's dummy
stuck in their mouth, and had to keep it there for the rest of the lesson.
Bullying or impertinence to a teacher : Girls had to wear a baby's
bonnet for a day. Boys had two bows of hair ribbon tied in their hair for a
day.
Swearing : Being a fairly strict Catholic school, swearing was
regarded as blasphemy, and the ultimate sin. It therefore earned you the
severest of punishments, and one that we dreaded. If we swore, the
headmistress used to contact our parents to obtain their approval to apply
it. Unfortunately for us, our parents (including my mother) almost always
approved.
And the punishment? Girls had to spent an entire day wearing a baby frock
and bonnet with appropriately babyish white ankle socks and a pair of black
patent strap shoes. A range of various made to measure size baby dresses
were kept for the purpose. Boys had to spend the day wearing the girl's
school uniform with ribbons tied in their hair.
What made it even worse was that the humiliating outfit was delivered to
our home the day before, so that our mothers would dress us in our
punishment dress first thing in the morning, make us go to school in it, and
ensure that we kept it on until bedtime at the end of the day. The outfit
was then collected the following morning.
I earned a dose of this most unpalatable experience one morning as a
result of taking the Lord's name in vain. It was silly of me really, and in
a way I more or less deserved it, if only because of my sheer stupidity. I'd
been giggling as I read a comic under my desk during class. Suddenly our
teacher Miss Markham stopped in mid sentence, and strode up to me. She told
me to hand over the comic, and as I did so, she said 'Very well Jimmy, it's
the dummy for you.' That's when I made my fatal mistake. I unthinkingly
swore, and at that she became furious. She looked at me and said 'How
dare you swear at me! It seems that something considerably more salutary
is required I think. I'm reporting this to Miss Wareham with the
recommendation that she applies the severest of punishments. And I think you
know what that is. She will inform your mother of her decision
tomorrow. That is all for now.'
She walked briskly back to the front of the class and continued with the
lesson, while I trembled in trepidation at the thought of having to undergo
what any boy would regard as the ultimate humiliation. Several of the girls
looked at me and tittered, as they relished the thought of me being dressed
as one of them for the day, and I blushed crimson.
True to her word, Miss Markham reported me to the headmistress Miss
Wareham, and I was duly summoned to her office at lunchtime the next day. I
stood before her, dreading what I knew was to be my fate, and I was right.
'Now then young man' she said grimly, 'It seems that you've committed not
one, but three offences. All at the same time. One, you were misbehaving in
class. Two, you were grossly impertinent to Miss Markham, and three, most
importantly, you swore at her in the process. You know what the punishment
for that is, don't you?'
'Yes Miss Wareham' I said quietly, trying to look as contrite as
possible. Didn't do me any good though.
'To…to have to wear the girl's school uniform for a day.'
'That's right' she said with a grim smile, 'I've already telephoned your
mother, and she's in full agreement that you should be punished. Miss
Markham will therefore deliver a girl's uniform in your size to your mother
this evening, and she will dress you tomorrow morning in accordance with our
instructions. Do you have anything further to say?' I could think of
nothing, and simply nodded my head in the negative.
'Very well' she said, 'You may go. In the morning you are to report to me
before assembly for inspection. Is that understood?'
'Yes Miss Wareham' I said miserably, and she told me I could go.
That afternoon I was continuously stared at by the other children, and
felt utterly wretched as I contemplated the next day. It was impossible for
me to concentrate on my lessons, and I passed the afternoon almost in a
trance.
When school ended that afternoon, one of the girls giggled and said to me
'See you tomorrow, little girl !' and the others burst out laughing. I
blushed and ran nearly all the way home, eager to get away from their
merciless teasing.
My reception when I reached home was icy. Mum was obviously very angry at
being let down by my behaviour, and showed no sympathy as she told me that
she would ensure that I would be immaculately dressed in my girl's school
uniform the next day.
Shortly after tea, Miss Markham delivered the uniform and explained
exactly what was required with Mum. Unfortunately, my mother seemed to be in
full agreement with her, and I dreaded what the next day would bring. Miss
Markham added that she would take me to school, and Mum would collect me
after school to ensure that I didn't get lost. There was to be no escape
from my fate.
That evening I couldn't think of anything else as I sat in the lounge
miserably watching television, and decided to go to bed instead. Mum told me
that she was going to get me up earlier than usual the next morning, so that
I could take a bath before she turned me into a sweet little schoolgirl.
With that hideous prospect dominating my thoughts, I went to bed. Mum had
already hung the all to familiar girl's school uniform dress on the door of
my wardrobe and laid out the other items on a chair ready for the morning. I
lay there in bed trying to read a book, but couldn't concentrate as I
frequently glanced at the dress hanging there as if it was lying in wait to
envelop me I its humiliating grasp. Eventually, and Mum came in to say
goodnight and put my light out, and I lay there in the dark, tossing and
turning as I tried to drive all thoughts of the next day out of my mind. It
took me a long time to get to sleep.
True to her word, my mother woke me up earlier than usual the next
morning, and after I'd taken a bath I padded back down the landing to my
bedroom where she was waiting to dress me. She'd laid everything out on the
bed in readiness, and I recoiled as I looked at the familiar uniform worn by
every girl in my school. I shuddered to think of the teasing I was going to
have to suffer when I arrived at school dressed as one of them.
'Right' said Mum briskly, your vest first.' She picked up a white
winceyette vest, not unlike my own, and helped me into it. But the next item
definitely wasn't like anything I'd ever worn. Mum held out a pair of navy
blue girls school knickers and said 'In you get.' I stepped into them, and
she drew them up my legs until they were round my waist. Then she tucked the
vest into the waistband of the knickers. They were slightly baggy, and the
elastic around my upper thighs and waist felt restrictive.
Next came the summer dress that I was used to seeing the girls in my
school wearing every day, and now it was my turn. It was a typical girl's
primary school summer dress made of blue and white check gingham, with a row
of white buttons up the front to the neck. It had short sleeves with white
cuffs, and a white pointed collar, and there was a breast pocket with a
white strip along the opening. The belt was fitted with a white plastic
buckle, and was threaded through two keepers attached to the dress at the
sides of the waist. On the end of the belt was a buttonhole to stop the belt
slipping open.
Mum held the dress up and put it over my head while I put my arms into
the sleeves. Then she pulled it down over me and fastened the buttons up to
the neck and secured the belt in place. On my feet went a pair of white
ankle socks which she turned down neatly, and on top of those, a pair of
black T bar strap shoes with buckles at the side of the foot. She made sure
that the strap buckles were tightly fastened so that they could not come
off.
Taking down a royal blue school blazer from its hanger, she held it out
and I obediently put my hands into the sleeves. Then she pulled it up onto
my shoulders and arranged it neatly. She stood back to examine me, grinned
slightly, and said 'I always wondered what you would of looked like if you'd
been a girl. Well you'll certainly look like one after I put some ribbons in
your hair. Sit down at the dressing table.'
I did as I was told, and blu
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