A place to collect the thoughts and experiences of heterosexual male cross dressers and transvestites. I try not to be judgemental - hell I was forty-something before I liked myself. I WILL plug the page where I have books to sell - but there are 'freebies' there as well so money isn't a big deal.
I'm ancient - so have many years behind me. With any luck I've learned some sense about myself and the subject of transvestism. Have no problem in learning more. Want to, as a matter of fact.
I'm a little unsure as to how this process is supposed to work and it may be difficult for contributors to pick up on someone else's storyline/character(s) but taking my lead from Belinda's great start here's my contribution. I've taken up on Bea's idea that there are maids on campus serving the staff/pupils and this explores our hero's first encounter with one of them.
Jack’s first days at school had
not gone as well as he would have wished and as if his first encounter with the
formidable Miss Savage was not enough he now had that bossy boots Pamela and
her henchwomen to contend with. They seemed hell bent on imposing themselves on
him, why oh why couldn’t his mother have gotten a job in a school with a better
male/female ratio. If there were any other boys in this school he hadn’t seen
them yet. It was bad enough being in an all-female environment without these
girls constantly referring to him as Jackie, hopefully it was only with Miss
Savage, Pamela and her cronies. Luckily he had a free afternoon as there was
cheerleader practice and he had made sure he avoided Pamela after class despite
her best intentions to corner him. He made a quick escape and was brooding on
this as he made his way home for what would thankfully be a quiet afternoon
alone as his mother had classes and meetings well into the evening.
Opening the front door he let
himself in and headed for the lounge, there might be some sport on the TV. He
changed into basketball shorts and had
barely settled himself on the couch when he heard the distinct sound of heels
on the hardwood floors.
“Shit” he thought to himself “thought
Mom was in class there goes my afternoon TV.”
“You must be Master Jackie” he
heard a voice say from behind.
Startled by the unfamiliar voice
he jumped up and turned to see a tall well-built brunette dressed in a grey
knee length maid’s dress, a frilled white pinafore and matching cap completed
the uniform. Standing in black patent leather three inch heels she gave a small
“Sorry to have startled you
Master Jackie, I’m Rose, your maid.”
“Jack, my name is Jack” he said
annoyed that everyone in this place seemed intent on feminising his name.
“Oh, I’m also Miss Savage’s maid
and she referred to you as Jackie should I mention this to her later maybe she
got it wrong” she said sweetly.
The last thing he wanted was
another tongue lashing from Miss Savage and thought discretion the better part
“No Rose, Jackie is fine” he reluctantly
conceded “and there’s no need to call me Master Jackie.”
“I’m afraid I can’t do that
Master Jackie I would be punished or worse if I didn’t, Miss Strang the
principle is most strict in these matters, and one of my fellow maids just lost
her job for a similar offence. That’s why I’m here earlier today usually there
would be two of us for a house this size, there’s a lot to do and I’m sure Miss
Savage or one of the other staff members may do a spot inspection and I will be
in trouble if they find fault.”
This Miss Savage was well named,
the poor girl was terrified and he could empathise having himself fallen foul
of her. She really seemed anxious and she seemed friendly enough unlike the
other females he encountered so far who were either scary like Miss Savage
,authoritarian like the principal Miss Strang or upper class bullies like
Pamela and her entourage. Even though he had just met her he felt a kind of
affinity with this put upon servant girl.
“No one will find fault Rose.I can give you a hand if you like” he
“That would be wonderful, I’d be
so grateful, Miss Jackie” she said.
“Ahem, Rose ……. Miss Jackie?” he
spluttered annoyed at the addition of Miss to his already feminised name.
“Sorry Master Jackie, it’s just
that I’m so used to serving ladies it’s just force of habit, hope you’re not
angry with me” she pleaded.
“No that’s fine, I understand” he
said graciously, feeling the girl had enough of these people hassling her
without him adding to it.
“We could start with the
bedrooms” she suggested.
Start? he thought to himself, he
had only intended maybe doing the dishes or loadingthe washing machine, now he had gotten roped
into something more. Although she was pretty though and he liked the
way her breasts stretched against the fabric of her uniform. An hour or so in
some pleasant company would be a welcome change to his recent experiences with
the local female population. If he played his cards right maybe he’d have a
shot with her at some stage.
He followed her upstairs and marvelled
at the way her backside confined in its tight material gently swayed from side
to side, her panty line stretched tightly against her ample buttocks.
“We can do the guest bedrooms
first, they won’t take long as they haven’t been used, just a cursory dusting.
I keep supplies in the small bedroom I won’t be a moment” she chirped.
He entered one of the guest
bedrooms too wait for her and thought she was right this wouldn’t take long at
all. A few minutes later she joined him carrying several items.
“Right where do we start” he said
trying to sound enthusiastic.
“We’ll just do some light dusting
and polishing but you’d better wear these Master Jackie, we can’t have you
getting your clothes dirty” she replied.
She held out a similar apron and
cap to the one she wore.
“Ah I don’t think so Rose” he
blurted recoiling from the offered garments “it’s no bother if I get them a bit
“I know Master Jackie but I will
have to wash and iron them afterwards and as I said since my fellow maid was
fired I already have so much work to do. Please it would mean so much to me”
“An apron and cap I would look
ridiculous” he insisted.
“No you wouldn’t lots of men wear
them, men on food counters, doctors in theatres, men in laboratories. Please,
Master Jackie, as a favour to me … please, I’d be ever so grateful.” she
He thought this really was a
ridiculous request but there was no one was around and he might rack up a few
bonus points with her, plus she did say she would be ever so grateful.
“Well ok” he relented “but not a
word to anyone.”
“Of course” she agreed “just our
little secret. Now let’s get you into your apron, hold out your arms.”
He held out his arms allowing her
to place the garment over them and then she moved behind him.
“I’ll just tie it into a nice
bow, I must show you at some stage how to do this yourself Master Jackie.”
Turning him around she made a few
adjustments to the frilled shoulders of the apron and fluffed out the skirt
until she was satisfied it fell correctly around his shorts.
“Doesn’t look too unlike a skirt”
she said. “Now for your cap”
He was getting embarrassed and
beginning to have second thoughts when she interrupted his thoughts.
“Is that really necessary?” he
“Oh of course it is, it’s to
protect our hair from the dust and grime and you really do have lovely hair,
which reminds me I’d best tie it into a ponytail before we go any further. Make
you look more presentable.”
He resented the word presentable
but without giving him time to protest further she took a small hairbrush from
her apron pocket and quickly brushed his shoulder length hair and tied into a
ponytail at the top of his head holding it in place with a tight piece of
elastic material. He squealed as she pulled his hair tight.
“Oh don’t be such a girl” she
chided and placed the frilled cap on his head and fixing it in place with hair
Again she stood back to view the
finished article and not quite satisfied she began arranging his fringe.
“Much better” she announced, and
finally satisfied with her work tookhim
by the hand ledhim to a dresser mirror.
He was horrified. The effect of
the apron and cap combined with his new hairstyle had undoubtedly altered his
appearance highlighting feminine features which he had not noticed before. He
raised his hands to tear off the cap but she anticipated this and caught his
wrists quite firmly.
“You’re not going to go back on
our agreement now, are you Master Jackie” she challenged him and then quickly softened
her approach saying with an almost timid voice,
“I do really need your help….
He dropped his hands and
“Oh all right then but let’s get
started the sooner we finish the sooner I can get out of this.”
“That’s a good girl” she
“What was that” he said unsure of
what he thought he heard.
“I said that’s very good idea”
she smiled sweetly.