Double Trouble

Neither myself nor my brother could believe this was happening as our mother opened the double doors of our wardrobe to reveal a resplendent display of skirts, blouses and dresses. “You honestly don't expect us to wear those do you?” Peter asked.

Half Term

At first, the idea of going to a boarding school filled me with as much dread as it did excitement... now, eight weeks in, I'm preparing to go home for the half term break. Unlike those who attend daily, us borders have to wear our school uniform in the evenings and on the weekends too. Whilst this may seem unfair at first... it's a common rule in many boarding schools. However there are some rules at St Ursula's which aren't very common...



It's Saturday morning and I can't wait to return home, see my mum, meet up with my friends and wear my own clothes for a change! On my bed is a small suitcase, inside which is the jeans, t-shirt and jumper, along with the shoes and socks I'd arrived wearing some eight weeks ago. It felt strange wearing 'civilian' clothes after two months in uniform.

I packed the books I’d need, closed the case and clicked the latches shut, before going to the school's office to collect my train ticket. The 55 mile journey home should take around 90 minutes. I made sure my room was all in order; bedding straight, floor swept, en-suite bathroom spotless and my uniform items all neatly folded on my shelf, or hung from my clothes rail... ready and waiting for my return in a week's time. I looked forward to a whole week away from the rules, the routine and the academia of boarding school. Saying that, I do have a number of homework assignments to do during the week long break, hence my small case being half full of both text and exercise books.

I made my way from the dorm, down the long corridor towards the stairs and ultimately to the school's reception desk. “Where do you think you're going?” a stern voice called as I descended the wide wooden staircase.

Home Miss.” I replied.

Not dressed like that your not... you know the rules.” Miss Holbeck said in the same stern tone.

But I'm going home Miss... to Beckford.” I said, lifting my small suitcase a little as if its mere presence validated my claim. “...on the train.” I added.

Nevertheless, the rules state that you should be in uniform at all times. And that includes travelling to and from the school.” she replied.


But nothing child.” she interrupted, “Your own clothes were in your case so that you could take them home, not for you to wear on the way home.” she stated, before telling me in no uncertain terms to return to my room and “...make yourself presentable!” as she put it.

My Sister's Birthday

“Oh that's not fair!” I sulked. “She came to my birthday party.”

“Yes and your sister knows how to behave herself... unlike you David.” mum replied. “Close your eyes.” she said.

I closed my eyes tight shut as mum rinsed the shampoo from my hair. Jug after jug of water ran off my head and over my face, splashing off my shoulders and into the bath. Once rinsed, I opened my eyes.

“Now I want you to be a good boy and stay in your room until the girls have gone. Do you understand?”

“But I don't want to stay in my room when Janet's having a party. I want to join in.”

“You want to tease her friends, make fun of their dresses, pull their hair and be the centre of attention David.” my mother stated. “And for that reason, you shall stay in your room... out if sight, and out of mind.”

Ready for Bed

Mother and I had driven up the M1 to spend the week with my cousins and aunt in Nottinghamshire. Since my mother began petticoating me a few months ago, this was a rare opportunity to spend some time wearing my boy clothes. As the car pulled up outside their house, my mother reminded me to be a good boy, otherwise she'd pull my pants down and spank my bottom in front of everyone.

“Yes mum.” I promised.

Being a petticoated boy, my mother insisted that I’d be wearing my knickers beneath my boy clothes everyday... so if she did pull my pants down in front of everyone, they'd all see my frilly knickers and the cat would be out of the bag.

The Salon Solution

Peter’s mother visited Margo's Hair Salon every fortnight and as a result, knew the proprietor, Margo very well. As well as the usual soap operas, holidays, celebrity gossip and current affairs conversations, Peter himself is often the subject of their biweekly chats. Like many sixteen year old boys, he gets up to mischief once in a while, but since he got in with a certain 'crowd', his mother fears he's headed down the wrong path.

“When he was little I'd threaten him with a dress... which always did the trick.” she reminisces. “But he's too old for petticoating.”

“Petticoating?” Margo asks.

“You know... a naughty boy plus a pretty dress equals a good boy.” Peter’s mother replies.

“You put him in a dress when he was naughty?” Margo quizzes, clearly taken aback at the revelation.

“Yes, occasionally... more often than not just the threat of a dress would curb his behaviour.” she replied. “You must have heard of petticoating?”

“Well... I'm familiar with the concept, but haven't heard it called 'petticoating' before.” Margo replies, “...and I had no idea people actually did it.”

“Only when he was really naughty. He used to look quite sweet in a dress... obviously he hated it but...”

The door opened and a customer entered. Margo welcomed the lady and asked her to take a seat. Margo changed the conversation to one more 'mainstream' as finished Peter’s mother's hair. Before long she was finished. Peter’s mother paid, booked her next appointment and left.

Petticoating for Schoolboys

I thought this Proactive Parenting guide was one of a kind...

But then I found this...

...a handy booklet by somebody who really knows what they're talking about.


After three fantastic days camping with old friends, I faced the most miserable journey home. Yesterday evening the fine weather broke and having rained throughout the night and throughout today, I'm soaked, muddy and desperate for a lift. A good hitching place doesn't often have any shelter and this is no exception. I know I look a state and don't really blame those who'd rather not have me dripping in their car. But it's mid afternoon; I’ve had my thumb out for almost four hours and have travelled a measly 20 miles. 

The weather is getting worse and the chances of being seen, let alone getting a lift are becoming increasingly slim. Then, just as I’d given up hope, a pick-up truck begins to slow down and pull in. Even if he'd only take me a few miles I’d be happy to get out of the rain, but the miserable git put me in the back of his pick-up. Ten miles later he dropped me off at a remote roundabout. I wished I’d declined the lift when I realised the passing traffic at this location was near zero. 

The few cars that did pass weren't stopping, and if i knew the area I'd have walked to a better location. Unlike the traffic, the time slowly passed by and the rain lashed down rapidly.  I must have sat for a good two of three hours when a car not only appeared, but stopped.

A pretty woman a few years older than myself, possibly in her early twenties wound down the window and asked where I was going. I replied and not surprisingly, she wasn't going that far, but could take me up to junction 6; about 30 miles. “Well, if you're sure?” I replied half-heartedly, “I am in a bit of a state.” I added looking down at myself.

“Hop in... it's a bit of banger anyway.” she smiled, “Put your backpack in the boot.” she said, opening it remotely.

“Thanks for this.” I said as I climbed in the passenger seat. “I'm sorry about the state of me...” I added, drawing her attention my filthy clothing. “ last lift was in the back of a builder's pick up.”

Growing up is hard to do

This story is Inspired by Jamie Vesta's 'Genderquake' over at Eves Rib, and in particular,
the post titled "You'll Wear What You're Told To Young Man"

Peter’s childhood was relatively normal; he played army with his friends, climbed trees, had a train set and loads of action figures and liked nothing more than his trusty old jeans with a hole in the knee, a zip up hoodie and his thoroughly worn in trainers.

His mother, Helen is an architect and his father worked part time in a biscuit factory. Helen often told her husband that he could give up work as her wage alone could easily support their family, but he was proud to work and wished he could get more hours and maybe even a promotion. But with more women in the boardroom, more women get promoted and as such, Peter's dad had been stuck on the shop floor for years whilst his mother's career went from strength to strength. When Peter was seven years old his father became permanently stuck to the shop floor when a section of racking collapsed, tragically killing him on the spot. Ever since that day, Peter has been raised solely by his mother.

With the support of his family and teachers, Peter faired relatively well with the loss of his father. The nearest thing Peter had to a father figure in his junior years was Ron Blakely; a widower in his fifties. Mum called him the handyman but mostly he Hoovers and irons, dusts and washes up. He used to be a proper handyman but as the work dried up for him, he diversified into a more domestic realm as that was one area which the women weren’t taking over. Even then, Ron found it hard to earn enough to support himself as more and more men were being laid off, leaving them plenty of time to tend to such chores. “In my day they used to call 'em kept men … if a bloke didn't have a job he was a sponger, too lazy to work ... these days they call 'em stay-at-home-husbands and it's supposed to be a good thing... times change lad... times change.” Ron said to an eight year old Peter.

Ron had to give up working altogether due to ill health and since then the ironing and laundry has been done by an agency; run by women, worked by men. Between the two of them, Peter and his mother kept on top of the hoovering and dusting.

Peter's mother gave him the freedom to strive to be all he could be and encouraged him to try his best, “Even if you're not very good at something, your best is good enough.” she used to tell him.


Eleven year old Peter watches his older sister Sally practising her tap dancing in the back garden, and noticing he's intrigued, offers to teach him some steps. “Now the basic steps are...” his sister demonstrates, and Peter tries his best to do them. “That's really good Peter.” she says after ten minutes.

“No it isn't... I'm rubbish.” he replies. “I just went thump thump thump... but when you do it, it's tap tap tap.”

“That's because you're not wearing tap shoes.” she says, showing him the soles of her shoes. “But you can do the steps quite well for a beginner.”
She gets him to try something a little more difficult, and again he gets the hang of it after a few minutes.

She's really impressed but he's less keen because when she does it, it sounds like tap dancing and when he does it it's just thump thump thump. Sally tells him to wait and disappears inside the house. Peter practises until she returns. “These are my old ones so they might fit you.” she says.

Peter sits down and removes his trainers, before squeezing his foot inside the black tap shoe. “I think they're too small.”

Jenny's Room

There is a prologue to this story, which isn't essential reading, set a few
months prior to these events as Peter's curiosity gets the better of him.
If you'd like to read why Peter began cross dressing, click here

 Image by Kimberley Wilder, used without permission but is the sole inspiration for this story.

“You shall remain dressed exactly as you are until I’ve decided what to do about this” my mother stated as her eye's dropped to see the semen dripping on to the floor. She turned to my sister and told her to go to the kitchen, before tuning back to me. “Right young man... come with me!”

Jenny's Room: prologue

I never understood my sister... or girls in general. It seemed as long as something was pink, they liked it. Growing up, my toys were trains and tanks, aircraft and spaceships. Action man, Batman, Spiderman, guns and skateboards and remote control cars. My sister however had dolls, a dolls house, and yet more dolls. She had a huge My Little Pony collection and a host of cute teddy bears. Her toys were all the same, all pink with flowers and love hearts whereas mine were all different, interesting and exciting. As we grew older, I stopped playing with toys and began building model kits and playing video games. My sister stopped playing with her dolls and began to spend all her pocket money on clothes, hair accessories, make-up and fashion magazines... but everything was still pink and frilly

Her bedroom made me feel sick, with its pink walls, princess bed and matching curtains. An ornate dressing table littered with lip-sticks and pungent perfume. Her bookshelves are home to the last of her dolls and teddy bears, books about clothes, hair and make-up along with stories of princesses and girls in boarding school having lame adventures. In one corner is a large pink framed mirror which she spends ages in front of, admiring her latest item of clothing or hairstyle. On the floor is a fluffy heart shaped rug... in pink of course. And perched on her chest of drawers is her TV & DVD player... in pink!