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.