Dresses Galore for Sissy’s// Timothy’s Room: Part 4

At school on Monday, James discreetly tells Timothy about having to wear a dress in front of his grandparents.
“I wouldn’t mind but… they all think it’s normal!” he says.
“The only people that don’t think it’s normal are me, you, Paul and…”
“Yeah I know.
Grown-ups are like that.”Timothy replies.
“Try telling anyone here and see what they think.” he sarcastically suggests, before warning James to be careful about what he says at school.
“Anyone could be listening,” he states.
“I know… but not here,” James claimed since they’re in the middle of the school playing field with no one in earshot.
“My granddad said that he knew some boys like us when he was young,” James said, adding that they had to wear dresses for school too.
“He said we’re lucky that we don’t.”
“Antony and Nicholas do,” claimed as James’s face adopted a look of horror.
“But they go to a petticoating school so all the boys dress like girls.”
“Oh… that doesn’t sound too bad.” James supposed.
“I thought you meant at a school like this.”
“Nah… my Mum wanted to but the headmistress wouldn’t allow it.”
“Crikey!” James exclaimed. “It’s bad enough just having to wear my knickers at school… let alone the whole kit and caboodle,” he said.
After a moment’s silence, James asked where Antony and Nicholas go to school.
“Oh it’s miles away… near Covenworth,” he said. “They get the bus there and it takes about an hour.”
“Yikes!” I retorted, imagining then having to use public transport.
“Oh, that’s OK,” I said when told that they’re collected by a school bus.
“Mum wants to send me there.” tells James, “…but she can’t afford it.
Thank God!” he adds.
“Hey… do you want to come round to my house after school one day?” James asks.
says he’ll have to ask his Mum first, but would like to.
“Any excuse for a few more hours not having to wear a dress.”
“Yeah… thankfully my Mum doesn’t make me wear them all the time… just on the weekend really.”
When James gets home from school, he tells his mother that he’s invited around one afternoon, “If that’s OK?” he adds.
“Of course it is.” his mother replied, before asking if he’s wanting to show off all his new things.
“No!” James insisted. “Just to hang out… you know.” he shrugged.
His mother suggested Wednesday would be ideal, and unbeknown to James, she telephones’ Timothy’s mother to check it’s OK with her.
“Yes, that’s fine.” Timothy’s mother replied.
“In fact, he’s just asked himself but wasn’t sure when…
I’ll come and collect him at about ‘five’ shall I?”
Tuesday is one of two days each week when James doesn’t have to wear his knickers for school, thanks to having PE.
But with all his underwear hidden somewhere in his mother’s room.
James has to ask for a pair of knickers when he gets home from school.
“Can have a pair of knickers please Mummy.” is something he’ll never get used to saying.
He doesn’t know what’s worse, having to ask for a pair of knickers or having to say ‘Mummy’.
But today it’s different as his mother tells him that there’s some in his drawer.
He goes to his room expecting to find his usual frilly ‘heart’ knickers with his name embroidered on the front but is surprised to find a small pile of normal knickers instead.
There are lots of different colors, mostly pastel shades, and all have a bit of lace around the hems and a little bow stitched on the waistband.
“Thanks Mum!” James says when he returns to the ground floor.
“I mean… Mummy,” he adds.
She tells him he’s welcome and asks which pair he’s wearing.
“I just grabbed the top pair.” he replied before lifting his school shirt to show her. “Spotty green ones,” he said.
“Nice.” his mother replied. “Is Timothy looking forward to coming round tomorrow?”
“Yeah, I think so,” James replied.
“His Mum said it’s OK.”
On Wednesday, James and Timothy walked back to Timothy’s house after school.
Timothy was looking forward to having a couple of extra hours wearing his school uniform as normally, he has to put a dress on as soon as he gets home from school.
Jame’s mother has no such rule, but when they arrive, Jame’s mother tells her son that she’s put his sailor dress out, and tells him to go and change.
“Oh but Mum!” James whines.
“OK,” he says when she gives him one of those looks.
“I’ll bet you’re more obedient at home aren’t you Timothy?” she says as John goes to his room.
She asks Timothy about school and once again tells him how nice he looked on his birthday, then after five or ten minutes, she says “I’ll just pop upstairs, he’s probably waiting for me to do his zip.”
A moment later, Jame’s mother returns and tells Timothy that he can go up to Jame’s room.
He finds a very sheepish James sitting on his bed wearing his navy blue sailor dress and a pair of white pelerine knee socks.
“It’s not fair that I have to wear this when I’ve got a friend around.” James sulked.
“I don’t mind,” Timothy said. “I won’t say owt,” he added.
“Yeah, I know.” James gulped.
Timothy cast his eyes around the books shelves and walls.
“At least your room isn’t all girlie like mine is,” he said.
“Yeah but she’s taken away all my model tanks and fighter planes, and Escape from Colditz,” James replied.
He suggested a game of Connect 4 or maybe Jenga, and they spent an hour or so playing both.
James’s mother interrupted them with a pile of laundry, on top of which is several pairs of Jame’s embroidered ‘heart’ knickers.
He quickly stuffs them in his drawer and feels himself blush as he does so.
“I guess you’re used to having stuff like that,” James asked.
“Yeah.” Timothy groaned. “I’ve got one pair of underpants which I can wear on PE days and that’s it.”
“Don’t you have any boy’s clothes?” James asked,
“Apart from your school uniform,” he added.
“Yeah I’ve got jeans and jumpers and trainers that aren’t girlie,” Timothy replied.
“Mum lets me wear those if I go out with my mates,” he tells James.
James is a little surprised to hear this as he assumed he was petticoated all of the time.
“Only at home,” Timothy replied.
“I do go places other than the school you know,” he informed him; places such as the town, the cinema, the nearby woods, fishing on the canal, ten pin bowling, visiting friends and family, the list goes on…
At 5 p m sharp, Jame’s mother shouts up to them as Timothy’s mother has arrived.
James feels completely out of place as they descend the stairs wearing his dress whilst Timothy’s dressed as a boy.
Timothy’s mother tells John how pretty he looks and John politely says thank you.
“You’ve got one a bit like that haven’t you Timothy.”
“Yes,” Timothy replied, glancing at his friend. “Only mine’s pink.”
“Oh, that sounds nice.” James’s mother said.
“You haven’t got a pink dress yet have you?” she says to her son.
He shakes his head and gulps, dreading the prospect of having one.
But the way his mother said ‘yet’ means that it’s only a matter of time.
Timothy and his mother left and James had a little whine about having to wear his dress.
“I’m sure Timothy doesn’t mind.” his mother replied, before suggesting that he apologize for moaning,
“Unless you want to wear your knickers for school tomorrow.”
Knowing that he’s got PE tomorrow, which means having to change in front of the other boys, James said “Sorry Mummy.”
“Well I hope you mean it.” his mother replied.
“I’m sure Timothy doesn’t whine and complain all the time.
I’m sure he’s a good boy and does as he’s told.” she supposed.
James apologized again and hoped that was enough to ensure he wouldn’t have to wear his knickers for school on a PE day.
Although he did start thinking of ways he could get himself excused from PE should that happen; a leg injury maybe, earache or asthma… that always works.
But then again, that probably only works for the kids who actually have asthma.
Thankfully he was allowed to wear his underpants at school the next day, but he did spend the evening wearing his dusty pink skirt and cream lacy blouse.
Over the next few weeks, the regularity that James wore his boy clothes at home decreased considerably.
His mother kept putting new charity shop finds in his drawers and wardrobe and to make space for them, his boy clothes were gradually removed.
She even bought him a few pairs of tights and even girl’s shoes including a pair of girl’s trainers with sparkly purple trim, some jelly sandals, and a pair of black ballet-style shoes that seemingly all the girls wear for school.
James wanted to protest but he knew that would only result in the last of his boy clothes (and footwear) being removed altogether.
As things stand, he can still leave the house dressed as a boy and he’s wise enough not to jeopardize that.
One lunchtime at school, James spots Timothy and Paul chatting and saunters over.
“We’re thinking of going fishing on Saturday afternoon if you fancy?” Paul said.
“Er… maybe,” James replied.
“But I haven’t got a rod or owt,” he added.
Paul said he’s got a spare which he can use and encouraged him to join them.
“I’ll have to ask my mum,” James says.
Jame’s mother checks with Timothy’s mother before allowing him to go fishing.
She also checks if he should wear one of his dresses since she’s almost as new to this petticoating malarkey as her son is.
“Oh no… not for fishing.” Timothy’s mother replied. “We let them be boys often enough.”
James has a great time on the canal bank with his friends.
Paul seems to know all sorts of things such as the names of the birds, tree species, and the types of fish they manage to catch.
They chat and laugh and joke.
They discuss their teachers and classmates and the lessons they either like or loathe.
They talk about TV shows; current and old and all sorts of other things.
There’s only one subject that’s out of bounds and that’s anything to do with petticoating.
The reason, according to Paul is that they spend enough time being petticoated and don’t want to spend the little time they’re not either thinking or talking about it.
When James arrives home, his mother asks him if he’s had a nice time and James begins to tell her all about it.
She stops him short and says,
“Why don’t you go and put something nice on, then you can tell me all about it.”
He reluctantly leaves and returns wearing the outfit he found laid on his bed.
“Why is there a new poster on my wall?” he asked.
“Because I put it there.” his mother tells him. “Do you like it?”
“Not really,” he replied. “I don’t like ballet.”
“You enjoyed Billy Elliot.” she reminded him before her eyes slowly dropped from his head to his feet.
She wonders why boys don’t normally wear scoop-necked T-shirts as it looks delightful on her son, especially with its white bow print on a pale blue fabric.
A pair of short baby pink denim shorts with polka-dot turn-ups make a nice transition to his patterned cream tights and on his feet a pair of black ballet shoes.
“Do you prefer tights to stockings?” she asked.
“They’re a lot easier,” he replied.
“They are aren’t they.” his mother smiled.
“Now… why don’t you tell me all about your day out.”
He tells her that he’s learned how to tie a fishing hook, bait the line, and cast off, as well as learned the names of some of the birds and trees.
He admits that they only caught minnows but a bloke down the bank caught an eel which they had a good look at.
He also tells her that the one rule they have is they don’t talk about petticoating.
“Well I suppose it’s nice to have a break from the routine.” his mother smiled.
James spent an hour or so in his room until supper was ready.
He flicked through his books and magazines, but couldn’t help but glance at the new poster on his wall.
It hangs in a place of his World War II Bombers poster, and couldn’t be any more different.
It features a ballerina wearing a pink leotard and tutu, white tights and pink shoes standing on tip-toe with her arms outstretched, and the word Ballet in big ornate pink lettering across the top.
“A girl might like that but I don’t,” he said to himself.
He returns to flicking through his SportStar comic annual and wonders how long before it’s replaced with a Barbie annual or something similar.
He sits upon his bed and stretches his feet out in front of him and wonders if he’d like these clothes if he was a girl.
He visualizes his other outfits and says to himself, “At least they’re better than my dresses… or that blouse Mum likes.”
At school, James glumly told Timothy that his mother had removed his world war two Bombers poster and replaced it with one of the ballerinas.
Timothy said that such things were inevitable and said he was surprised at how ‘boyish’ Jame’s room was the last time he visited.
“When I started my mum had my room decorated within a week… it was awful!” he exclaimed.
“It is pretty bad,” James added as he visualized Timothy’s very girlie bedroom.
“It’s better now, believe me!” Timothy said.
He glanced around to make sure no one else was in listening distance, before describing his first girlie bedroom; all pink with Hello Kitty wallpaper, curtains, bedding, and a deep fluffy Hello Kitty rug.
He described the toys and accessories that filled it; the girlie bedside lamp, the toy crib and a shelf full of dolls, the flower fairy mobile where his model aircraft used to hang, the pink plastic fairy castle on his chest of drawers… the list went on.
“Blimey! Just having that Tinker Bell mural doesn’t seem so bad.” James said.
“I hope my Mum doesn’t do anything like that to my room,” he adds.
“Well don’t be surprised if she does,” Timothy replied.
“Just because you’re twelve doesn’t mean they won’t treat you like a five or six-year-old.”
“I hope not.” James gulped.
If it’s just clothing then it’s not so bad, but if he ends up having to play with dolls and stuff like that, it’ll be unbearable.