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A Sissy Boys Mother Wishes

I thought about the question for a moment before replying.

“I really don’t know.” I said.

My brother looked me up and down and smiled.
“Because it’s fun.” he told me as he jumped off the dresser and twirled around in his pink satin pyjamas, grinning from ear to ear.
“Boy’s clothes are just so…” he said, forging a frown, “…boring.” he smiled.
“But Girl’s clothes…”
Meanwhile, their mother is travelling interstate and wondering how James and John are getting on.
It’s been three years since their father passed away and ever since that fateful day, she’s been more afraid of losing her two sons than anything.
She feared that one day they’d meet a young lady and marry and as the old saying goes;
a son is a son ’til he finds a wife but a daughter’s a daughter for life.
It’s been eight months since her eldest son James was introduced to the pleasures of femininity, although for him it wasn’t very pleasurable to begin with.
At the age of sixteen, she sent James to a finishing school in New Hampshire
where he lives as a boarder and learns to be a lady,
but as far as he knew at the time, and as far as his younger brother John is currently aware,
it’s supposed to be a normal boarding school, albeit a very expensive one.
James was dropped in at the deep end;
stripped of his masculinity,
corseted and feminised… and he’s come a long way.
For John, however, he’s going to receive the softly softly approach and all being well, by the time he enrols at the same finishing school he’ll be a far more willing student from the outset.
James and John spent the whole weekend playing dress up.
James teaches John how to apply make-up,
with the expected results for a beginner and ends up doing it for him.
John finds the whole experience thrilling but can’t really fathom why his mother encouraged his brother.
The only answer he’s received as to ‘why’ is because it’s fun.
“So… when Mother returns, shall we be dressed as girls or boys?” John asks as he rolls a silk stocking up his hairless leg.
“What do you think?” James replied.
“I don’t know?” John replied as he fastened the suspender clip.
“That’s why I’m asking,” he said.
He sighed and added,
“For all I know you could be teasing me and Mother’s got nothing to do with it.”
James assured his brother that he wasn’t ‘teasing’. “Why would I do that?” he asked.
“To get me in trouble,” John replied.
“It wouldn’t be the first time.”
“But I’d be in just as much trouble.”
“Not if you made sure it was just me wearing Mother’s clothes,” John said as he looked at his reflection;
his long slim legs clad in expensive silk stockings,
held in place by a suspender belt that’s hidden by a pair of champagne French knickers.
From his shoulders hangs a matching satin camisole,
trimmed with lace and decorated with a tiny satin bow.
James assured his brother that he wasn’t plotting anything of the sort.
“It’s up to you what you’re wearing when she returns,” he said.
When their mother did return from her trip, both James and John wore their own clothes.
John made sure that they’d left her room and wardrobe exactly as she left it three days previously.
This was because part of him didn’t believe that the endeavour was his mother’s idea.
After a warm welcome, she sent James upstairs with her cases.
She then asked John if they’d been having fun and asked what they’d been doing whilst she was away.
“Er… not much really.” he guiltily replied.
“No?” she replied.
“I was hoping that James might have shown you some of the things he’s been learning at school?”
“Er… what kind of things?” John hesitantly asked.
“Oh you know.” his mother casually replied.
“Things like, shaving your legs and shaping your eyebrows…” she said. “
…wearing my makeup, my lingerie, that kind of thing.”
John gulped. “Is that what he does at school?”
“You haven’t answered my question yet.” she replied.
“…and if I’m not mistaken, it does look like you’ve at least shaped your eyebrows.”
“Oh er…” John sheepishly stammered. “…yeah… James did it.”
“And the rest?” she asked.
John gulped and nodded.
What felt like a silly, impulsive and maybe even naughty bit of fun now feels shameful and deeply humiliating in the cold light of day.
John reiterated his question about what James does at school.
“I think you’ll find that he does lots of different things at school… pampering, preening and enjoying nice clothes is just a small part of it.”
Shyly, John asked his mother if it was her idea and she said it was.
“Why?” he asked.
“Because if you can learn to enjoy it, you’ll be much happier when you start boarding school,” she told him.
“What kind of school is it?” John asked.
His mother replied and John quizzed,
“You mean like girls go to?”
“Of course… only this one accepts boys too,” she replied.
She glanced towards the door and the sound of James returning.
They waited in silence for a few seconds until he appeared.
“John’s being a bit shy about what you two got up this weekend.” she said.
James told her exactly what they’d done, from showing his brother how to shave his legs and plucking his eyebrows, to trying on her underwear, clothes and nightwear.
“And did he enjoy it?” she asked.
John gulped and felt increasingly guilty when his bother told her that he did.
“He loved your blue baby doll.” he added.
“Who wouldn’t?” their mother grinned.
“Once you’ve realised just how lovely some lady’s garments feel against the flesh, there’s no going back.” she said.
“And I think by doing it this way, John’s transition won’t be traumatic like yours was.”
A frown crossed James’ face and he hung his head a little.
“I wish I’d been a bit more willing and hadn’t tried to fight it.” he said, before wishing he’d been forewarned too.
“Well you came round eventually.” his mother said.
“If John was the eldest it would have been he who’d been dropped in at the deep end and you’d be in his position now.”
John listened intently as he tried to get his head around just what was going on.
“Er… what position?” he asked.
“Being mentored by your big brother.” his mother replied.
“By the time you start finishing school you could be halfway to being a lady…
providing you enjoyed the weekend as much as James says you did.”
John couldn’t deny anything that his brother had told his mother, but he also couldn’t allow himself to admit it either.
Yes he enjoyed playing dress-up all weekend.
However, now some of the finer details of the boarding school he’ll soon be attending have been revealed,
what seemed sweet is beginning to taste a little bit sour.
“Why do you want me to be a lady?” he hesitantly asked, glancing at his brother and correcting his question, “…or us?”
“Because boys always betray their parents and since your father passed on,
I can’t risk you betraying me.” she said.
“We won’t betray you!” John claimed.
He wanted to add “What makes you think we would?”
but his mother interjected with…
“I know you won’t.”
After a brief uncomfortable silence (at least on John’s part) she added,
“So… now I know what you two have been doing, aren’t you going to ask me about my trip?”
“Er… how was your trip?” John asked.
“It was very nice thank you.” she replied.
“And I brought you present.” she told him.
James asked if she’d brought him one too.
“You’ve already got one.” she smiled.
“What is it?” John asked.
His mother grinned and said “I’ll show you later.”
She paused to observe his reaction and although John wasn’t bursting with anticipation,
he did seem a little disappointed that he’d have to wait and see.
She decided to give him a hint and said,
“It’s something for you to wear.”
After a weird and wonderful weekend being introduced to the joys of femininity,
John laid in his bed that evening wearing the baby blue baby doll nightie and with a heart full of worry.
He also wore the gift his mother had given him and it was the very last thing he expected.
He didn’t want to touch it but he couldn’t help himself.
His brother advised him to try not to think about it,
but that’s far easier said than done.
A nervous yet inquisitive hand slid down his short satin nightie,
raised it and reached beneath the frilly elastic waistband of his baby doll panties…
its sole intention is to feel the very thing it didn’t want to feel.
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