The academic
year was progressing well at the Stuyvesant Academy for Young Ladies (and one
terrified boy) and on the surface it was very much similar to most schools
catering for the offspring of the very wealthy. A well-structured academic syllabus
with an extensive and varied programme of extra- curricular activities meant
the students had a multitude of choices open to them and officially they were
greatly encouraged by the staff to participate to ensure a well-rounded education
but in reality it was to guarantee that they were kept out of trouble.
It had been
a tumultuous introduction to life at the Academy for Jack. He had been forcibly feminised for a weekend
by Rose-one of the school’s maids - after she found him in an embarrassingly
compromising position and as a result was now firmly under her thumb. If that
wasn’t bad enough his mother had arrived home early to find him wearing one of
her satin nightgowns that Rose had forced him to wear to bed. As his mother
knew nothing of what had passed between Jack and Rose (she had been away at the
time with Miss Strang the school Principal), and was under the illusion that he
had discovered a previously unknown feminine side and wanted to get in touch with it. Rose obviously
did nothing to enlighten Mrs Swanson to the true reason behind Jack’s feminine
attire and had actually planted the seed in her head regarding this new tender
persona but also suggesting it might be best if it remained their little secret to avoid needless
embarrassment to Jack. As if to further emphasise his predicament and add to
his discomfiture Jack was also manoeuvred into referring to his mother in true
girlish fashion as “Mummy”. His mother was delighted to discover that her son
had a softer side, it almost made up for not having the daughter she always
wanted. Jack however was disgusted that he had to maintain this feminine
charade but knew Rose was capable of exposing him to his mother and maybe even
the Principal. Every evening to please his mother he had to don a satin or silk
nightgown and peignoir and present himself to her before retiring for the
night. Since he was a child he was aware she had a propensity to check on him
regularly and if he removed the nightgown he knew she would confide in Rose so
he was forced to spend the night within the confines of the soft ultra-
feminine nightgown.
In the days since his mother’s return Rose
seemed to be a constant feature around the house and it was obvious that his
mother was quite taken with her and had developed a relationship more akin to
friendship rather than maid and mistress. Jack was alarmed by this new female
pairing and despite his best efforts was being drawn into its orbit. He was
constantly being asked his opinion on all things feminine, his mother’s new
dress or shoes, Rose’s new hairstyle or earrings. His football and music
magazines disappeared overnight and were replaced by girl’s and woman’s fashion
publications. His chores were now almost exclusively consisted of helping Rose.
When his mother was absent for a few hours she wasted no time in having him
capped and aproned but he was grateful that she had not the time to dress him
in full uniform. To his barely disguised annoyance she constantly tormented him
about their time together and just as he would consider rebuking her she coyly
raised the issue of a certain signed confession to a lewd act and he reverted
to his submissive role.
It was a
relief to him when his mother suggested that they take a trip into town to
purchase some kitchen utensils. A morning following his mother around a
shopping mall would undoubtedly be a boring undertaking but a far better
prospect than another Saturday with Rose. While trawling through what seemed
like the hundredth store he wondered why was it that his mother like most women
could not just go to a store get what was required and leave? Why did she have
to spend what seemed like an eternity mulling over her choices before buying a
simple item. Imagine, he thought, what it would be like if a gaggle of them got
together, they could spend hours rabbiting before deciding. It was while this
usual performance was being acted out he heard a vaguely familiar voice from
behind him.
“Gail I
haven’t had a chance to thank you properly since I got back” the voice of
Principal Strang boomed out to his mother.
“Principal
Strang I didn’t want to disturb you during your convalescence” his mother
replied.
“Gail please
call me Janet, you were so very kind in my hour of need I think we can dispense
with the formalities” and turning to Jack said
“I do hope
you realise what a kind and warm hearted person your mother is young girl”
Jack shifted
uncomfortably and wanted to correct her immediately but thought her use of the
word “girl” a slip of the tongue. The truth be known her physical stature and
her position as Principal were also quite intimidating factors. He was somewhat
annoyed that his mother had ignored this slight however he was forced to mumble
“Yes Ma’am”
The women
practically ignored him as they chatted away and he was relegated to the role
of bystander.
“I was just
on my way to purchase some lingerie my sister usually accompanies me but she is
indisposed and I wonder could I impose on you, I would dearly love your
opinion.” Miss Strang asked his mother.
“I would be
delighted” Mrs Swanson replied.
Jack was
thrilled, at last he could get away and cruise the mall and check out the new
games store, not to mention girls, maybe get a pizza later as they were bound
to take ages. His planning was rudely interrupted as his mother addressed him
“Come along
dear, the lingerie store is this way”
“I thought I
might visit the new sports store I need new sneakers”
Jack visibly
paled as the two women looked impatiently at him. Miss Strang shot him one of
her fierce looks and said in a stern voice
“Young lady,
I do hope you’re not going to disobey your mother and besides teenagers running
around unaccompanied are a poor reflection on our school.”
“I .. I mean…. It’s just ….” He stammered as he
reeled from her withering look and authoritarian voice which he had witnessed
reducing girls to tears on several occasions. He was far too afraid to mention
this was the second time she had referred to him as a female.
“Now come
along we haven’t all day” she continued as she positioned herself by his side
and with his mother at the other they moved off with him firmly secured between
the two women.
His heart
was racing all the way to his dreaded destination, his eyes darted about to see
if any of the girls from school were in the vicinity. None were visible much to
his relief, a small but welcome mercy.
He had seen
lingerie departments in stores before, from a close but discreet distance and
had stolen furtive glances at women examining various items of underwear. On
one such occasion some women had noticed him and smiled knowingly in his
direction which made him blush a bright red and immediately beat a hasty
retreat. However this was different he was frogmarched into the heart of an
obviously exclusive lingerie store. There was nowhere to scamper off to, no
escape, nowhere to hide, here he was in the most feminine environment imaginable
and in the company of the formidable Miss Strang and his mother. He heard the
door close behind him, there would be no escape this time - he was trapped. The
store was populated by women of various ages and sizes all browsing racks of every
imaginable type of intimate feminine garment and as they moved through the
store his nostrils were assailed by the scent of dozens of different perfumes. He felt, but more importantly looked like a
fish out of water, the only male in a woman’s world. They followed Miss Strang
as she made her first foray through various racks of delicate garments stopping at one she turned to them
and said
“I think
these slips are divine, what do you think girls?”
“Yes they
are beautiful Janet but I think you’re mistaking my son for one of the girls”
Mrs Swanson said smiling and at last correcting her.
Jack was
relieved that finally it was being pointed out to Miss Strang that he was a boy.
His recent traumatic experiences with Rose were bad enough and now his mother
thinking he had a feminine side and practically forcing him into wearing a
nightgown . Miss Strang referring to him as a girl was really the last straw
hopefully now that she realised her mistake he might be allowed to go.
Miss Strang
somewhat bemused looked at Jack as if it was for the first time.
“Oh don’t
mind me I’m just so used to seeing girls all the time I keep forgetting we have
one boy. A slip of the tongue but I’m sure you don’t mind?” she said in a soft
but firm voice and using the hated feminine version of his name added
“Do you
Jackie?” fixing him with a look that
seemed to dare him to contradict her.
“Um no I suppose not” he demurred
“How kind of
you so I’m sure you won’t mind if I occasionally forget and use a female rather
than a male pronoun after all Jackie can be used as a girl’s name as well as a
boy’s and with your long hair, well…..I’m
sure you understand.”
His mother
standing behind Miss Strang gave him a
look which left him in no doubt as to the required response.
“No Miss
Strang I understand” he lied.
“It’s not a
problem Janet, Jackie doesn’t mind, he’s not one of those macho types I’m glad
to say. In fact joining the school has made him more sensitive to the feminine
perspective” his mother volunteered causing Jack’s stomach to tighten.
“Getting in
touch with his feminine side eh? What a dear sensitive boy I wish some of our
girls had such gentile sensibilities.” Miss Strang cooed.
“Isn’t that
right, Jackie?” Mrs Swanson said proudly.
“Yes Mum”
Jack again lied as every fibre of his body squirmed with embarrassment and to
add insult to injury now even she was calling him Jackie.
“Jackie I
thought we agreed how you would address me” she admonished.
Was there no
end to her attempts to embarrass me he thought but as both women waited impatiently
for his answer he swallowed hard and he duly gave the required response.
“Yes Mummy”
“How
adorable” Miss Strang gushed as her two arms enveloped Jack and drew him into
her body. The discrepancy in their height meant his face pressed directly into
her large pillow like breasts. He could smell her very femininity and to his
horror had the stirrings of an erection, he was soon released and she turned
her attention to his mother saying
“Oh Gail I
hope you don’t mind it’s just it’s so unusual to discover such a delightful and
agreeable young man, I was quite overcome.”
“Of course
not, I’m sure he doesn’t mind, isn’t that right Jackie” she said.
“No Mummy”
he replied knowing any other answer would not be acceptable.
Recovering
from her sudden attack of emotion Miss Strang and his mother turned her
attention back to the slips hanging from the rack, his mother picked one showed
it to Miss Strang and said
“I think
this one is gorgeous Janet.”
“Yes Gail, I
love pale pink, it’s such a feminine colour, Jackie would you be a darling and
hold it up to your body so we can get an idea of how it looks on.” Miss Strang
said and without waiting for an answer handed him the slip.
He had no
choice but to do as she asked and awkwardly held the silky soft slip at arms
length up to his chest.
“No, not
like that I can see you’re not used to this dear” Miss Strang said and directed
him to hold the slip to his shoulders by the straps and it fell the length of
his torso to his knees.
“Much
better” his mother said approvingly and continued “yes I love that colour and
the mocha lace is so pretty. I think we’ll have a look at some others.”
Jack knew
there was no point in protesting at this point and complied meekly as the women
gave him slip after slip in various colours and materials to hold to his body
for their inspection. To his further discomfort he noticed a number of women
observing his ordeal and his unease increased as they approached, he was
shortly surrounded by women taking more of an interest in him than the
lingerie.
“What a
pretty slip” one of them said as they engaged in a conversation about its style
and material.
“Would your
daughter mind if she held up this one?” another said “I’m hoping to convince my
own daughter to wear one but she’s such a tomboy, always in jeans”
Jack could
see what was coming and wished the floor would swallow him.
“Oh this is
not my daughter, it’s my son, I will really have to do something about his hair
I suppose it’s easy to mistake him for a girl, he’s just
helping us out as we try to decide which ones to buy” his mother said as Jack
blushed furiously.
“I wish my
daughter would accompany me lingerie shopping, she says too busy playing sports
for all that girly stuff, you’re so lucky” she said and all her friends nodded
their agreement as they smiled approvingly at Jack. He knew this ringing
endorsement would only entrench his mother’s and now apparently Miss Strang’s
views also.
“Forgive me
but I’m sure I know you” Miss Strang said to the woman “does your daughter
attend the Stuyvesant Academy”
“I thought I
recognised you also” she said “I’m Emily Quinn , Pamela’s mother, I’m visiting
my sister who lives close by for a few
weeks and thought I would drop by and bring Pamela shopping but she flatly
refused to accompany me, much prefers browsing through sports stores than
lingerie shops, as I said a bit of a tomboy. I’d love to stay but I have an
appointment and must rush.”
A shiver
went down Jack’s spine at the mention of Pamela’s name but was relieved that
Pamela wasn’t with her to witness this spectacle. That would have been
unbearable.
Then came the coup de grace as she turned to
his mother and said
“Please
don’t take this the wrong way and I do
mean this as a compliment he really would make such a darling girl. I’m so
envious I don’t get to do girly stuff with my daughter.”
Her
entourage concurred with another collective bout of head nodding and warm
smiles. Jack almost suffocated in the oestrogen laden atmosphere. He hadn’t
been so humiliated since his subjugation at Rose’s hands. Far from being
insulted his mother beamed as did Miss Strang at this notion and Jack was
grateful as the clutch of women moved away before they could add more fuel to
this particular fire.
“Oh dear I’ve
just remembered I have an appointment at the nail salon would you mind looking
after Jackie until I return, it shouldn’t be long” his mother said to Miss
Strang.
“Of course
the dear girl is no bother” she said
Before Jack
could say anything she thanked Miss Strang and was gone and he was left alone
with this intimidating woman.
“Come along
Jackie , I need some other items” she said as she headed for another part of
the store and added “ and bring the pink, ivory and powder blue slips with you”
Hanging his
head in shame and trying to make himself look as inconspicuous as possible he
followed her carrying the satin and silk slips, any hope that they were headed
for a quiet corner were soon dispelled as Miss Strang sought out the manager.
“Ms Strang
how nice to see you again” the store manager said eyeing Jack who stood
slightly behind her as she noticed him
holding the feminine garments “we have that new range you were inquiring about.
Please follow me.”
“Thank you
Michelle” Miss Strang replied with an easy familiarity.
Jack
dutifully followed the two women to an area with mannequin displays of various
styles of foundation wear.
“Would the
young lady like to try on the slips in the dressing rooms?” the manager said
“Oh no the
slips are for me this is my friend’s son, he’s being such a darling helping me
out while his mother attends an appointment.” Miss Strang said
“Son? Oh
please forgive me, I’m such an idiot” she said to Jack “I forgot to put in my
contacts this morning we don’t get too many males in here. It must be your
longish hair and wonderfully long eye lashes.”
“That’s ok”
Jack mumbled knowing there was nothing else to say.
Jack stood
there feeling like a fool as the manager showed Miss Strang various types of
girdles and bras whilst discussing the merits of each item. Eventually after
what seemed an age they seemed to settle on several items.
“I know you usually
like assistance but all my assistants are tied up at the moment if you would
like to wait for fifteen minutes or so I can have a girl attend to you.” the
manager said.
“No that’s
quite all right” Miss Strang said and laughed “I brought my own, now come along
my dear, leave those slips on the chair and bring those bras and girdles” she
ordered pointing to the various items of satin and lace on the counter.
He gingerly picked
up the items of underwear and followed her into the spacious dressing room.
“Maybe I
should wait outside” he said
“Not at all,
I’m sure you’ve seen your mother in her underwear before and it’s not like
you’re one of those horrible macho boys” she said as she unbuttoned her blouse revealing
her ample bosom encased in a formidable bra under a black satin slip. Turning
her back to him she said
“Unbutton
and unzip my skirt, there’s a good girl.”
As she
stepped out of the skirt she took off her blouse and handed it to him. He
bristled at being referred to as “a good girl” but nevertheless said nothing
and laid the skirt and blouse on the chair as she slipped off the straps of the
slip and let it fall to the ground and stepped out of it. He instinctively bent
down and picked it up place it with the skirt and blouse. Noticing he did this
without instruction she said
“Your mother
certainly has you well trained now hand me that new bra before you unhook me
then turn your back until I call you again.”
After she
remove her bra and slipped her arms into the new one she again called for him.
“You may
hook me up now” she commanded and he obeyed silently delicately fastening the
seven tiny hooks into their matching eye tabs.
“Excellent”
she said “you would make a wonderful lady’s maid, but I think I may have the
wrong size. Run along to Michelle and ask her for a white long line bra size
38D, oh ask her for a flesh coloured open bottom corselettte and make sure it’s the one with satin panels.”
He baulked
at the mention of lady’s maid as it brought back the humiliation he suffered in
that very role at Rose’s hands. There seemed to be no end to her demands but he
reckoned the sooner he got this over with the better and he made his way to the
counter to get the requested items.
The few
customers at the counter gave him quizzical looks and he felt even more
uncomfortable than previously if that was possible as he waited for Michelle.
“And what
can I do you young man” she said, loudly enough for the customers to stop what
they were doing and take notice of this male interloper.
Jack
whispered the instructions he had been given by Miss Strang but Michelle
apparently had difficulty in hearing them and said in a loud voice
“I’m sorry
dear boy I can barely hear you, is that a 38B or 38D long line bra you want?”
Jack went
bright red instantly and barely managed to stammer
“38D”
The women at
the counter began to giggle and one of them said
“I thought
he was more a 36A”
Michelle
noticed Jack’s discomfort, smiled at him and gently admonished the customers
“Ladies,
this young man is being very gallant in assisting one of my customers, now what
else can I get for you”
“A flesh
coloured corsellette with satin panels” he mumbled
“A flesh coloured
corsellette with satin panels” she repeated again in a loud voice “is that a
panty corsellette or open bottomed?”
“Open
bottomed” he blurted wondering how long would this torture continue.
“Same bra
size?” the seemingly unending questions continued as the women customers could
now barely contain their laughter.
Jack was on the verge of tears when Michelle
again intervened.
“Ladies…..
Please. Leave the poor boy alone”
The women
gather around Jack and hugged him.
“We’re
sorry, we didn’t mean to hurt you, please forgive us”
He recovered
his composure enough to nod his acceptance and as he took the garments from
Michelle and was about to walk away he
heard a voice behind him saying
“I’d love to
see him in a tight corsellette with or without satin panels.”
He
recognised the voice immediately.
Pamela.
“When Mother
told me there was a nice young man in the lingerie store helping his mummy and
Miss Strang I knew it could only be you.”
“I’ve got to
get back to Miss Strang” he said cursing his bad luck and briskly walking away
from her but she fell in beside him.
“I see
you’re acting as Strang’s lady’s maid, I wonder what she’d say if she knew you
had previous experience” Pamela said, smiling.
Reaching the
dressing room he knocked on the door and waited for Miss Strang to bid him
enter.
“About time
too” Miss Strang said impatiently “now unclasp me and hand me the new bra.”
He went
through the same ritual time and again until she had settled on what she wanted
and after going through the indignation of helping her dress again they emerged
from the dressing room to be greeted by his mother, Pamela and her mother.
“I ran into
Pamela and her mother and Pamela said she’d love to meet Jackie when she found
out he was here. I do hope Jackie was of assistance” his mother asked Miss
Strang
“He was
wonderful, quiet, dutiful and biddable, unobtrusive but always at hand” she
said
“You’re just
described my former lady’s maid” Pamela’s mother said “ she left last month and
I’m lost without her, so hard to find one these days
with the qualities you’ve described.”
Pamela
grinned at Jack as he squirmed at Miss Strang’s description.
“Now run
along with these to Michelle like a good girl and tell her I’ll need four bras
and five corsellettes as well as half a dozen slips in the various colours.”
Miss Strang said as she handed him the various items.
He stood
rooted to the spot and briefly thought of throwing them back at her but one
look from his mother dissuaded him of that particular notion, he meekly took
the items from her and made his way to Michelle for what promised to be another
embarrassing encounter.
It took him
several minutes to return with her purchases and the women were in deep
conversation when he arrived back.
“Of course
it will take several weeks and a lot of hard work” his mother was saying as he
re-joined the group “but it is a great idea.”
He was
relieved that at least they weren’t still talking about him and lady’s maids in
the one breath but wondered what the hell were they discussing?
“Well thank
you so much Mrs Swanson but I would only do it if Jackie took part also” Pamela
said with her fake sweet smile.
Jack was
totally lost, just what are these people talking about now? he said to himself.
His mother enlightened him
“Pamela has
written a one act play as part of her drama course, she’s auditioned her
classmates for the other role and none are suitable but she feels you
would be perfect for it. You’ve done plays before, what do you say?” his mother
said beaming at him as if he’d been asked to play opposite Meryl Streep.
“I… I’m not
sure, I… I have a lot on” he struggled
for words but his mother was having none of it.
“Nonsense
you have a lot of free time and you have no tests coming up, you don’t want to
disappoint your friend now do you?”
“Oh please
Jackie” Mrs Quinn said “it would mean so much to Pamela and I”
All four
women looked at him expectantly. He had no excuses left and now no options
either.
“Ok I
suppose so” he said reluctantly.
“Oh thank
you so much Jackie” Mrs Quinn said, a sentiment echoed by the other two women.
Pamela just smiled and Jack had a sudden familiar queasy feeling.
“What’s the
name of the play?” he asked, now with some trepidation.
“Oh didn’t I
mention that Jackie?” Pamela said still smiling.
He shook his
head.
“The
Mistress and Maid”
Jack groaned
audibly and tried to argue but the women were already all talking together at
fever pitch and no one heard his anguish or protest. When they finally stopped
they again thanked him profusely and Pamela kissed him. A Judas kiss he
thought.
“See you at
rehearsals” she said and walked away grinning.
To be
continued.
