Head To Toe
Players
Jack as Julie. Clair, Jack's boss. Helen, Clair's secretary
and a host of supporting cast.
Synopsis
A remark. A thoughtless comment to a secretary, and a young
man's journey begins. His beliefs needed changing, his boss
said, and sometimes it's better that the lessons don't
always come from a book. He needed to change and sometimes
those changes are head to toe.
Fact From Fiction:
Irony is something that has fascinated me a great deal.
Sort of like chance in some ways. I've experienced both,
enough times in my life, to appreciate each in my life.
Much of this story is taken from those situations I look
back on with that sense of irony, wondering if it really
was just chance.
Story
Chapter One
It was a remark right out of the fifties, Clair thought.
Something her father might say only the voice younger and
much less authoritative as his had once been. More a
condemnation, and simply because of a person's sex. One
half of an entire species subservient to the other half for
no other reason than being born female, and it sent a
shudder down her spine.
She was furious by the time she reached her door, and it
showed when she stood face to face with the young as Mr.
Cater. His smugness changed slightly to a touch of fear,
and he automatically took a half step back to regain his
space. A trick she had learned long ago when confronting
men.
Get into their zone or space, and they'll retreat
automatically. A subconscious act, but they'll grow
uncomfortable having done so. "Another great weapon in the
feminine arsenal." her mentor, once said. It was, and it
always worked, and it worked now.
"Mr. Carter, a word if you please!" She said fighting the
urge to knock him to the floor. She was an expert in kick
boxing, held a black belt in karate, earned a dozen awards
as a girl gymnast in collage, and could have done just that
without chipping a nail. It would have also brought her an
intense amount of pleasure seeing his face looking up at
her.
Although she didn't. "The one big advantage of learning
self defense isn't always the ability to defend yourself,
so much as that confidence you gain in knowing you can!"
Her teacher had once said that. How true that was now as
well, as she allowed the young man past her. She hadn't
moved enough, making sure he had to again violate his own
sense of space to enter her office.
Clair had one more advantage that few shared and it was her
anger. She'd long ago learned to channel her fury into a
way of using it. That adrenaline rush, for her, the same as
pushing the gas pedal of a car to the floor. Her mind
sharpened instantly, as did her focus, as she eased her
door closed.
"Would you like to explain that remark you just made to
Helen?" Ms. Evan's asked standing, again, too close to the
young man she stepped up to.
"Ma'am?" Jack asked slightly confused and very definitely
intimidated. Scared suddenly, as well, given that her fury
seemed directed at him for some reason.
"Are you slow Jack? Didn't you understand the question? Do
you need another moment to gather your thoughts?" Clair
asked moving her face another inch forward.
"No! I mean, no ma'am. I... She... She made me miss a fax?
I missed it because she used the last of the paper in the
printer and... She's just a secretary, and she should known
better... And she made me miss a fax. I... I was mad. I'm
sorry. I honesty didn't mean it." Jack stammered in hurried
little flows of jerky words. He was in a desperate attempt
to defuse this situation he suddenly found himself in.
His own words adding more insult to that woman's injuries,
and worse, fueling the fire Clair felt flair again over
those words "...she's just a secretary..."
She took a few seconds to work her fury into her statement,
but she kept it in her tone: "Jack, I want you to go
quietly to your desk, take whatever is yours and, if you
don't mind, on your way out, stop by personal to let them
know that I've fired you. I'll include a two week severance
check with what we owe you, and ask that you honor my
gesture of good will by also apologizing to Helen on your
way out!" Clair said.
"Fired? I'm fired?" Jack said in utter dismay and total
shock. It wasn't that bad as remarks go. He was the fair
haired boy around here. A rising star! To fire him for that
remark, and to a secretary of all things was... It was
inconceivable.
"You really are slow in some things aren't you Jack?" Clair
said allowing his show of emotions to satisfy her own in
those seconds. She got that rush often when she was
fighting her way to the top of most things to do with men.
That look of total defeat, on her opponents face, a second
before their resignation and, shock over it, set in.
"Ma'am, I didn't mean it. I honestly wasn't thinking.
Please, I want this job, and I will apologize. Immediately!
Gladly! Honestly it was said out of anger. Please! Give me
this chance!" Jack said as the realization of his dreams
began to shatter. He wasn't so high up, so critical, so
important suddenly, and that alone weighed heavily on him
in that instant. So did the prospects of walking out that
door for the last time.
Clair for her part regretted firing him. He was important,
and would someday, she had felt, sit at the large oak table
with her other stars, or would have. It was a damn shame
and she felt it deeply. Although not enough to save him.
She had less than a zero tolerance for a male chauvinist
pig. A term she used from collage for those professors that
said, in so many words back then, that a woman should focus
on home and family.
Years of that chauvinism had been both her curse, and her
blessing as she moved through the ranks. Half again as fast
as her male peers after twice the effort. Learning to
overcome that view by working harder than they did. It had
worked, and she now stood at the top, and if this young man
only understood what it meant to be a woman in a man's
world...
Chapter Two
It struck her like a bolt of lightning thundering down to a
point just before the crack and that odd smell of ozone. If
he did know what it meant to be a women? If he stood in
Helen's shoes for even an hour he'd soon appreciate that
there is no such thing as "just" as secretary.
There were two kinds of people, in an office setting, that
Clair admired most. Two unique individuals simply because
they were the truest first image of a company: That
receptionist that people first saw; and, that secretary
that always finds order in the midst of chaos. She hired
the best, and paid them accordingly. That thought came and
went and another formed.
"Jack! I don't think you meant it on a conscious level, but
I do think you believe it on a subconscious level. That's
bad! That needs to change! However, I am going to give you
another chance or at least offer it. I'm going to offer you
an alternative to this being your very last day. An option,
but only because you'll have to decide for yourself if you
can do this or not. I believe it's for your own good. You
might not agree but again that's going to be your choice.
Understood?" Clair asked.
"Anything! Yes, I understand! I'll do anything!" Jack said
as his hopes rose. A second chance from a woman that rarely
gave second chances. He almost hugged her. Almost. You
don't really want to hug a lioness that's upset with you.
However, his job was facing him again, and yes, he would do
anything.
"Fine! This weekend my staff and I are meeting for next
quarter's strategy and numbers. You're working on some of
the material, or were, as a matter of fact. Helen is
working that day, as well, mostly keeping the minutes for
my presentation to our board. I was going to bring in a
temporary to help her with meals and refreshments. For the
sake of that remark, I want you to be that temporary and
work for Helen. Do you think you can do that?" Clair asked
being cleaver not to add the rest of it. A decision in
small bites is often better than forcing them to take the
whole thing and risk choking.
It would be humiliating, embarrassing, and well beneath
what he thought his station was, but yes, he could
understanding at some level her intent. A penance of sorts.
Okay, he could do penance. He could do that for this second
chance.
Punishment with a touch of justice to the woman scorned
Jack thought. A tough decision any other time, but not this
time. His job was on the line. Jack had a way back, and he
wasn't about to let it slip through his fingers.
"Yes ma'am. I could do that. I'd be happy to." Jack said
making it clear he was both thankful and more than willing
to work his way to her good side.
"Excellent. I had honestly hoped you'd swallow your pride,
and accept this. I still believe you are an excellent
contributor to this company, and it would have been a shame
to lose you. I'll let Helen know, and have her arrange for
your makeover. Frankly I think a day or two in her shoes,
in a figurative sort of way, will do you a world of good!"
Jack didn't miss a couple of things beginning with her
hating to lose him. He knew without a doubt that he'd of
been walked and still could be. He was also slightly
confused over that "... in her shoes, in a figurative sort
of way..." coupled with that thing about his
"...makeover..." One meant in a figurative way, that other
literal?
"Ma'am?" Jack asked and paused.
"Yes?" Clair asked.
"That thing about a makeover? I'm not clear on that?" Jack
said.
"Experience Jack! We learn by our mistakes! We gain
experience by doing things twice at times. Once to get a
feel for things, and the second time we do it better.
Always better after we've gotten that feeling for things.
Although sometimes our education can't be simply taken out
of a book Jack. You've learned some things about women.
They're wrong! Now you must relearn some things Jack! The
right things. Sometimes our education... what we learn,
actually has to be experienced to understand it. Do you
understand that?" Clair asked.
"Yes ma'am. It's just that I'm still not clear on that
makeover part?" Jack said feeling confused over what she
actually had said with a touch of dread growing down in his
gut.
"Makeover? Jack, a makeover is a makeover? Oh, I didn't
cover that very well did I? Okay, first of all don't worry
about the cost. I'll pay all of the expenses for that and,
of course, you'll be on the clock the whole time. As for
what we tell people about that? I've got it! We'll simply
say that you've lost a bet to me, and that was the deal we
made if you lost. Should be more funny than not, and while
your ego is going to be badly bruised, you should weather
the storm fairly well. Questions?" Clair said holding on to
her serious face as Jack's changed.
Chapter Three
Jack suddenly understood what she meant by all of that
mumbo jumbo she'd uttered and why he was getting a
makeover...
"You are asking me to... You want me... Are you
suggesting..." Jack was talking as his mind searched for a
way to ask what he was thinking. He was thinking the
unthinkable. The unimagined was being imagined. The
impossible was suddenly a prospect. She couldn't be
serious? It was a joke! It had to be!
"Look Jack! Let's play this out! It could be the worse
thing that has ever happened to you, and, yes, the most
humiliating experience you've ever faced. Or... Or, and
think about this for a second, or, it could be the most fun
you've ever had. Sure, you'll be teased, chided, poked fun
of and all of that, but they'll also think you've lost a
bet! You are also, most of the time, a pretty gutsy guy and
people know that. I know that! It's why I hired you in the
first place. Besides, those guys that get wind of this will
be a little jealous over the attention you're getting, and
no one, besides you, me and Helen will know otherwise.
"Look, I'll talk with Helen and explain it, and, trust me,
she's a good person. The best there is at what she does,
which is why I got so angry at you. It won't be much
different than if you did this at Halloween, and, for the
record, I can name five guys that came into this office
swishing on that day. In fact, if I remember correctly, you
were one of them.
"So come on Jack! Take this like a man, and you keep your
job. If that's not possible... Fine! Then I am truly going
to miss you. I will miss you, but I have no tolerance for
what you did and that is simply that. However, if I'm right
about you, and I think I am, you'll do this for all the
right reasons, and be the better man for it.
"If I'm wrong... If I've missed the mark completely...
Well, then I'm wrong, and you can say so right here and
now. Say so, shake my hand, and we'll still part on good
terms. I still think you are one hell of an asset, and no
doubt will continue to be where ever you go. So, what's it
going to be Jack?" Clair asked.
Jack stood there in awe that he was still standing there.
He did want this job to continue but this... This was so
odd, so impossible to consider that it was shocking that he
hadn't said no. Although he also knew, without a shred of
doubt, that he'd be out of work a second, at most, after he
did said no.
"So I would be paying off this bet with you, or something?"
Jack asked.
"Exactly! Well done Jack! You would be paying big time and,
if that's a yes, we'll walk out of here laughing, In fact,
I'll say something appropriate like 'I warned you not to
bet with me!' or something to that effect to get the rumors
started, and you can walk around and start telling those
you think need telling what just happened. I'm betting
you'll get sympathy, some small amount of empathy, and a
whole lot of kidding. The thing is this won't be during the
week, and this meeting is scheduled for off site as well.
It's just me, with staff. Staff only besides Helen, Jack.
My staff most everyone that is going to be there knows me,
and some of the offbeat things I've done.
"Plus, two of those women-want-to-be guys that showed up
Halloween are going to be in attendance as well. So,
indirectly at least, you'll have company as it were. Again,
if that is a yes and I'd like to hear it from you, then
that's that. If you do say yes then I also want you to
casually ask Helen for her forgiveness when she comes in,
and give her your best apology." Clair said smiling for the
first time.
"So what would I have to wear?" Jack asked.
"Something pretty Jack! You know, tasteful, functional,
feminine and above all pretty. Something that you think I
might like? Something you might like?" Clair said laughing
and then added: "Do I take that's a yes?"
"Yes!" Jack said dropping his eyes.
"Oh stop that! Look, I have never read that putting a man
in a dress has actually killed him. However, if this
actually does kill you then I'll promise, right here and
now, to make sure you're buried in something pretty! Okay?"
Clair said laughing again.
"Thanks!" Jack said feeling the stress pass. As bad as it
seemed, at first, it didn't seem as bad suddenly. It was a
joke, or could be and she was right... If he handled this
the right way he might even pull it off as such.
"Ready?" Clair asked.
"No! Can I have a drink first?" Jack asked.
"Sorry, that's for the clients. Don't push it either. We
don't drink on the job, remember?" Clair said as she walked
to the door and opened it.
Chapter Four
"Helen? Can I see you for a moment?" Clair said as she
leaned out.
"Yes ma'am?" Helen said coming in. Jack got a look from
her, but it was just a glance and he deserved it after what
he'd said, and he took his cue from Clair.
"Helen! That remark of mine was totally uncalled for, and I
apologize sincerely. Will you accept my apology and forgive
me?" Jack asked.
Helen smiled. She was born that way, and immediately said
yes. Jack extended his hand and said: "Thank you."
"Speaking of which! Jack dear! We've still got that bet to
deal with! How about I make Helen in charge of this so she
can get even a little?" Clair said.
"Do I have a choice?" Jack said smiling, as much as he
could, but only doing so because Clair was. Helen was
looking on in confusion but she too was still smiling.
"What bet?" Helen said feeling the mood lighten and noting
she join in and ask.
"Well, Jack here was so cock sure of himself that he made a
little wager with me, and being the superior being that I
am I, of course, won. So my young man here has to pay up.
He's going to need some minor bit of supervision and
assistance though in paying. Anyway, I thought it would be
appropriate, since we are going to be meeting this weekend,
that he be your temporary help as part of that wager. You
game? I mean if you think he can do this sort of work that
is?" Clair said in mock seriousness.
"Jack? I guess? I mean I was going to have the temporary
agency send over a girl just to help serve and clean
mostly. Nothing really heavy duty. Yes, I suppose Jack
could do that?" Helen said with a curious look on her face,
but it changed to a smile as she added: "Sure, he'll do
just fine. Won't be as pretty I suppose, but he'll do."
"Oh? Well... Helen, on that note, and why I need your
help... Actually Helen, he could be! He should be! Helen,
listen, part of the bet is that Jack here is going to spend
some time in my shoes, or your shoes, or a new pair like
ours, and I'm not being figurative. That was part of the
wager. Think you could spend some time on Thursday or
Friday shopping with him for something 'suitable' to wear
for this weekend?" Clair asked.
Helen looked between the two, and in an instant began to
laugh. "Really?" Helen asked as she tried desperately to
compose herself.
"Really." Jack said looking down trodden and very forlorn.
"Yes! Yes I could. Oh, what fun. I'd be delighted. What's
my budget?" Helen asked.
"Well, don't put us at risk of going bankrupt, but don't
put him into something dowdy or plain either. If I'm going
to be putting this young man into a dress, then I'd prefer
it meet with our companies image. Right?" Clair said.
"Right!" Helen said between snickers.
"Helen!" Clair said, and then added when Helen turned back
to her: "Head to toe if you know what I mean?"
"Oh! Oh yes... Yes I do know. How wonderful this is going
to be!" Helen said with genuine glee in her voice. Then
suddenly it was gone slightly as she asked: "Hair? Nails?"
"Head to toe, my dear. Head, middle, front, back, hands and
toes!" Clair said and then added after her own snicker:
"Use my salon, and tell them I want the works! The works
Helen!"
"I will!" Helen said and then asked: "Is that what you
wanted to see me about?"
"No actually, but I'm glad you're in charge of this.
Anyway, I want to go over what we'll need for this meeting,
and I'm going to need some foils made." Clair said as she
started to usher Jack out.
Chapter Five
At the door she said in a voice that could be heard to the
forth of fifth desk away from her: "No backing down now
Jack! A bet is a bet. You lost, and you owe, so go find
yourself a pair of nylons and take this like a man!"
Clair laughed as she closed the door.
"What was that all about?" Stan asked looking at Jack as
Jack walked over to his desk.
"Would you believe it? I lost! I was sure I'd win this one!
I still can't believe I lost!" Jack said.
"Lost what?" Stan asked.
"That stupid bet with Ms. Evans, and she's serious about me
paying up!" Jack said.
"How much?" Stan asked.
"I wish it was money!" Jack said feeling his throat
tighten.
"What did you bet her?" Stan asked with a serous look of
curiosity on his face.
"I've got to wear a dress! I've got to wear a dress, and
serve her and her staff this weekend. Can you believe that?
A damn dress!" Jack said blurting it out.
"Not on a good day! Man, that's definitely not a bet I'd
want to make or lose." Stan said.
"Me neither, but I did. Stupid, I know so don't say it!"
Jack said walking back to his desk. He fell into his chair
dejected and exhausted. It felt like an eternity had passed
since he'd walked into Clair's office. He was still sitting
there as the rumors began spreading.
"...Hey, did you guys hear about Jack's bet... That bet
with Clair... Poor guys got to wear a dress and serve her
and staff this weekend! Can you believe that?" One guy said
to another.
"Damn! I'd hate to be in his shoes!" Another added.
Several laughed, and the guy that said it, got the joke.
"Right! I get it! His shoes!"
There were pats of sympathy after a short while. Some
teasing, as well, from both the guys and the gals, and it
was just as Clair predicted. The girls offering advice like
"he's a Spring and should stay with pastels" or "this style
of nylons is the best for the money" and etc.
The guys gave him sympathy, but a lot more of that teasing,
which included a few remarks about perhaps getting together
some night for say a movie and dinner? And, more
importantly, which bathroom was he using since he was now
Clair's new maid.
Which also led to a question on what sort of dress he would
wear? One of those maid outfits was what most of the guys
decided on. One of those little shortie black things with
the ruffled panties. Ruffled panties along with handcuffs
and a whip.
A whip and a few other things that brought tears to their
eyes. By days end it had mostly settled into "a rib poking"
kind of thing falling into the background fairly quickly as
work again took priority.
Chapter Six
Which would have been that, except for the fact that Clair
and Helen had still been meeting when Jack left.
"Helen, beside the fact that he's lost that bet, and has to
wear a dress, he insulted you. I don't like that sort of
thing. So, I thought I'd also teach our young man an
important lesson as well." Clair said.
"Like what?" Helen asked not sure exactly what her boss
meant. She did hope, but then again...
"Like don't put him into something too adult! Try and find
something a little cuter. Younger perhaps. He's small
enough, and frankly, I think I'd like him to do just a bit
more penance for that remark of his to you." Clair said and
added: "Think you can do that?"
"Oh definitely! In fact, I've got just the place! It's
adorable. They've got some really cute things there. I shop
there for my niece on occasion. He'll hate it!" Helen said.
"Excellent. Now then, we're going to need two projectors,
some flips charts and..." Clair said changing the topic as
Helen started writing.
Jack meanwhile was just sitting down at his desk after that
exchange earlier with Stan, as Helen smiled. It was a
wicked sort of smile.
There are good days, great days and days like this one!
Helen thought to herself as she left Clair's office. Her
boss, aside from this weekend to do list, had just told
her, in so many words, that she wanted that horrid little
man dressed as a little girl. How can you possibly measure
such things?
Chapter Seven
Life is good! Helen thought as she tossed her handbag on
the kitchen table and picked up the phone.
"Mary?" Helen asked at the end of the forth ring and a
hello.
"Hi Helen!" Mary said recognizing Helen's voice.
"It's my niece again! This time something's special!" Helen
said.
Mary laughed. It was always Helen's niece and it was always
something special.
"What sort of special?" Mary asked and added: "And how big
is your niece this time?"
"Very, very special! And she's off the rack! I'm guessing a
twelve, maybe even a ten plus. How is your inventory this
time of year?" Helen asked.
"For off the rack? Honey, a twelve or ten plus size gets
you a large part of the store's inventory. This isn't one
of your boys is it? I thought you retired?" Mary asked.
"No, no! No, it's not for one of my boys and yes I did
retire. Actually this is for a young man I work with. Seems
he's lost a bet although I don't think that's the exact
case! Anyway, I get to dress him up as a little girl, or
something close, for this weekend, and thought I'd check
with you first for his outfit." Helen said, and then added:
"It's a head to toe outfit! Shoes, dress, undies, the
works."
Her flashbacks began with Mary's question and her own
statement. How wonderful those days were. She was a teacher
back then. A damn good one, and the school private.
Private, and stepped in tradition. It had been seven years
ago, and as clear today as if only yesterday.
Chapter Eight
She bought her first dress from Mary in nineteen fifty
seven. She'd said it was for her niece then as well. Mary
had just opened her little boutique. Of course that niece
was Mr. Rice and she smiled.
Mr. Rice had been very rude to her. Mr. Rice learned very
quickly, but not too quickly, what being rude to Helen
meant. It was so wonderful that face on him as he stepped
into his first pair of panties.
By the time Mr. Rice went on to his next grade level, he
was knitting his own little booties and sewing like an
expert on his own little dresses. That was her first
"niece". Her second came along almost at the same time,
then a third, and before long too many to count.
All of her nieces, became the most well behaved of little
boys. Perfect if one could imagine such a thing. It was
also difficult, looking at those pictures she still had, to
even imagine those were little boys.
A few, and poor Mr. Rice was one of those, wore diapers.
That was her ultimate discipline back then. Nice thick
cloth diapers, pretty little ruffled baby pants and
something very cute and very little girlish, that didn't
cover either.
How wonderful life can be she thought again. When the
school closed, and she found herself out of work, she
discovered another career. It was so ironic that it would
be Mr. Rice again as one of her first clients.
Same sort of dress she now knew he favored, and always with
his little diaper and cute little baby pants under it. He
might me Mr. Macho to his fellow officers, but he was
hardly that when she tugged his arm towards the nursery.
Of course, for a hundred dollars an hour, she tugged gently
but firmly. Little Ms. Macho, like many of her special
boys, liked it when she tugged gently and firmly and she
laughed. She laughed, stopped and closed her album.
She laughed a short laugh, shook those images from her
mind, and cleared her throat before asking Mary: "So where
were we? Ah yes, so no problem with finding something
suitable then?"
Chapter Nine
Helen, if you were casting a movie, was your classic image
of a mom, schoolteacher or favorite aunt. That woman who
immediately made you feel like a kid again smelling of
lilacs, and you could imagine, fresh baked bread.
She even had that ever present beaded link around her neck
to hold her glasses. Glasses that often sat above an ample
bosom she covered with a sweater. She was the perfect role
and it was, a role.
It was one of many images that Helen had perfected over the
years. She had an excellent schoolteacher look, a very
stern nurse image, and a few others that she found that
boys liked. However, at work she was your classic image of
stability and efficiently.
Mom, many called her at work, including Clair when she was
feeling slightly vulnerable. Mommy to those young men she
took time to discipline still but only part time now. Nanny
also, when it was diapers, or even ma'am when those that
deserved it, got to their little pats with her spanking
stick.
She wasn't sure yet about young Carter. She wasn't sure
which sort he'd be. How he'd see her. She was sure it would
at least be a "ma'am". She was positive of that. She was
also wondering how long it might take for her to train him
into those adorable diapers and ruffled panties. She'd like
that. He wouldn't, but she would.
She suspected not long. He was too small as men go. He was
no doubt too small as a child as well. She was sure his
mother had also taken advantage of that blond hair when he
was younger. She would have.
Then there was Halloween. Guys that wear dresses on
Halloween will wear them other times as well. Guys that
wear dresses at other times will wear dresses any time
Helen thought. They just needed good enough reasons. Helen
was always great at finding good enough reasons.
Besides, she thought, Mr. Carter was a bit too prissy for a
boy anyway. A bit too high strung as well. All perfect
traits for that young man about to step into his first
dress. It wouldn't be nearly as much frills as she'd like,
because that would take him past this joke, or bet, or
whatever it was forcing him into it.
It would however, be pretty, and most definitely sweet. The
rest could come later she thought. If she thought she'd
like him that way. She suspected she would, but then again
she always liked boys "that way".
Chapter Ten
Her brother was first, and a big part of how she learned
both trades. Her mother was a teacher as well. Also a good
one, and petticoat discipline back then was more than a
respectable form of punishment. Although not the diapers,
or those rubber panties her mother insisted her brother
wear for his bed wetting.
Helen always enjoyed those moments. Her brother's diapering
at night. It made her feel superior. So to those times
watching him being dragged into her bedroom, and even more
so when he emerged so sweetly dressed. She was younger, but
heavier than he was, so her stuff fit him quite nicely.
Helen was also the boss of her brother, next to mom of
course. Some ways more so because of that ever present
threat of "telling". Of her telling his friends what he
wore at night. Or what he wore when he was "bad". Helen's
brother always did as she said.
She had also thought he hated it. Only he didn't.
It wasn't until later that he confessed to his naughty
little thoughts in her pretty little things, and before
long he was doing what she wanted without any threats. If
you consider withholding some things as a sort of threat.
She did that, at times, if he wasn't a good little girl or
sweet little baby for her. Most of the time he was. When he
wasn't, he didn't get his reward. That became true of her
older boys, as time went on. It was those experiences she
took with her when school closed for the last time, which
was just before Madam Helen began.
Chapter Eleven
How silly to give birth to a baby, she would say. All that
work so unnecessary, when you could have almost all of the
babies you desired. Babies, she would point out, that are
so much more well behaved than real babies. She would note
this often, to those who also practiced in this art but
hadn't yet discovered diapers as a tool.
Mary didn't practice those arts although Mary knew of them.
Mary was Mary and her dress shop had been there forever. So
Mary had become something of an ally back then. A resource
like none other when Helen walked into that shop for her
next "niece".
Mary and she hugged for the first time in a long time
before Helen introduced her to young Mr. Carter. Of course
Mary took the hints, and treated him like the poor soul he
was. That poor man having lost that bet, but she knew
better, as did Helen.
Mary also knew that it didn't much matter the reason for
his girlish things, because all that often mattered was
simply getting them into them. Once that was accomplished
the rest, as they say, is simply nurturing. Nurturing is
natural and men adapt quickly to it Helen knew. So did
Mary.
You nurture a young man while he's wearing his pretty
things, Helen said, and before long he's forgotten he's a
young man. You nurture him carefully enough, and long
enough, Helen would add, and he'll never want to be a young
man again.
"Spare the rod, but not the dresses!" Helen's mother often
said as she sat her brother down in the living room in her
best Easter dress. Helen had learned that as well, as a
young girl, but carried it with her all of these years.
She wasn't a psychologist, by a long shot, but she knew
what boys sometimes dreamed. She also knew that all boys
dreamed those dreams at times. Some only once or twice.
Others more often. A few all the time.
She wondered if Jack had those dreams? She was sure he did.
She was also sure he would.
Chapter Twelve
"Now what are we up to?" Mary asked after Helen introduced
Jack to her. His face flushed when he entered, had remained
flush right up to that point. Helen had asked to bring him
in after hours. She was sure it was the only way Jack would
have agreed.
"He's going to need an outfit! Something suitable to help
me with a conference this weekend. Something pretty, but
not too fancy. Cute and functional. Has to be functional.
Do you have anything that can match those qualifiers?"
Helen asked.
"Of course! What's your chest size my lucky young man?"
Mary said teasing a bit. Mary, like Helen, always
considered this as hardly punishment, as much as a process
of discovery for males. That this was nothing more than a
little breach in their facades when they stepped into their
first bits of finery.
As Mary had once put it to a mother watching another
fitting her son with a dress: "If every man wore panties,
and those panties were truly panties, then we'd have little
need for armies or sedatives." A statement she also made
one day when she helped two aunts and with a struggling
young man into his first panties.
A unique situation for him, thanks to his aunts, and for
Helen there as a consultant as she watched his struggles
subside till they diminished. Diminishing was almost always
proportional to the number of layers that covered him. By
the time that young man had left he was a demure as any
little girl in her own new dress.
Jack gave his chest size and Mary nodded and a slight wink
passed between them as she moved off towards the racks
saying: "There are dresses, and then there are dresses. My
Daisy Kingdom dresses all come with pinafores so we can mix
'pretty' with 'functional' quite nicely."
Jack was in front of Helen and didn't see the smile on her
face. He did note the dresses he was nearing and turned
around still walking and said: "I'm thinking of something
older. Adult kind of. You know what I mean, don't you
Helen?"
"Actually I do. That's why I think these will be more than
suitable. The others far too juvenile. Besides, you risk
spilling or mussing your little dress without that apron or
penny on. Right?" Helen said in as cheerful a voice as she
could muster. She waited only a brief moment before adding:
"Of course if you'd rather not do this..."
"No! I mean no, anything is just fine with me." Jack said
in a sudden panic. He'd fully expected to be in one of the
major department stores rather than in a little girl's
boutique. Although, he wasn't really clear on what to
expect, since he didn't know a thing about girl's clothes.
Then again he'd seen that style dress on girls and none of
them older than pre-teen and why he needed that sort of
dress wasn't clear at all as he said: "Don't you have
something... You know, less... Without that lace stuff?"
"Honey, these ARE the dresses with the least lace stuff.
Are you talking about the ruffles? Or the flounce? These?"
Mary said holding the dress up to show him the flounced
hem. Lifting the skirt also showed off the self slip
attached and he almost stepped back, except Helen was
there.
Mary always loved this part when Helen brought in a niece
or two. It wasn't often, but when she did she loved that
look on their faces. Girls adored lace, ribbons, bows,
flounces and ruffles. For boys the opposite was true.
The more lace, bows, ribbons and ruffles the more scared
they got. The more scared they got the more delighted the
two women became. As Helen once said to one of the boys
she'd walked in for his little dress: "Honey, if it's not
pretty, then what's the point?" Helen almost said it again
but didn't.
Jack was having second, third and forth thoughts as the
women picked out a couple of dresses they liked. Not what
he liked, but what they liked. It seemed, to Jack, that
what he didn't like or disliked didn't much matter.
It also seemed that they liked what he didn't like more.
Although Helen, off to the side of them did lift one up
that made Jack want to faint. It was a dress girls wear for
the ultimate like pageants and such.
So Mary was right as far as these being least frilly, as
Helen lifted that one, she said, was something to die for.
To die over Jack thought. He was almost happy when Helen
hung it back on the rack. He was almost willing to wear the
one Mary settled on. Almost.
Chapter Thirteen
His first try on dress was a mauve, almost pink and very
classic Daisy Kingdom. Large flowers from the bottom of the
skirt up to that flouncy thing, to the ruffled things on
the shoulders. And that was without that apron or pina...
coat thing or whatever it was.
His dress zipped up the back and was made snug with a sash
but neither was touched. Mostly the ladies wanted to get a
"feel" for the style. Jack would happily be willing to give
both a feel if they liked. He thought this as they moved
around him like mothers around a little girl picking at the
ruffles and deciding.
What the hell was the weekend going to be like he thought
as he moved a hand away from the skirt, till he thought
better of it given how that looked. He didn't want to touch
the skirt, nor did he want to look like he was posing so he
folded his arms. "That's not very lady like!" Helen said.
Jack bit his tongue to keep from saying what he wanted to
say. It would have been a lot worse than what had gotten
him there. He was in his third dress, and this one just
slightly frillier than the second, which was slightly
frillier than the first.
Start them in muted tones, less frills and a nice cotton
broadcloth and work them up to taffetas and lace if they
are new to this. That's was Helen's advise to a wife who
had caught her husband cheating on her. Which in his case
meant he would start in satin's and lace, only wearing
cottons when he cleaned.
"It's the slips and panties that gets them hooked!" Helen
also said during a seminar on dominating men. "They have no
parallels to those fabrics in most cases." She'd noted that
then as she was noting it now.
Jack's third dress wasn't a Daisy Kingdom, but styled like
one and the slip wasn't cotton. It was a bridal slip of
sorts with a layer of taffeta nylon before a layer of tulle
before another of taffeta. Very pretty, very noisy and very
little girlish.
A wonderful dress Helen thought before letting Jack know
she'd actually decided on the first. Jack's relief was
obvious, although Helen had seen his legs moving ever so
slightly under that second slip.
She so loved boys, and those little movements they often
made while they protested. Of course that was the dress he
was going to wear, but why spoil it for him. He had settled
on the plain one and he'd sleep better thinking that.
He also didn't get panties or his "underslip". A girl
wouldn't need one with that sort of dress, but a necessity
for a boy and his first girl lessons. Girl lessons are much
better taught with girl clothes she thought.
So too those panties she'd bring with her. "First panties"
were rarely store bought! First panties simply had to be
special. Special panties Helen like making for her special
boys.
Special panties were always two layers, with one silky
layer out, and the other one facing in. Panties like those
always capture their imagination, she noted more than once,
and their fantasies she added. She really did know a lot
about young men, and smiled at what she already knew about
this one.
Chapter Fourteen
"I think we're just about done. He'll need shoes, of
course, and socks so lets get the shoes next, and I'll come
back tomorrow for everything else." Helen said before
turning back to Jack and asking: "Unless you'd like to come
back with me?"
Jack nearly hurt himself shaking his head no. Her coming
back alone was fine with Jack. Getting out of there was his
goal, and if it took a pair of shoes then so be it.
"Those are definitely for little girls!" Jack said as Mary
brought over a pair of shiny black patent Mary Janes.
"They're perfect with that dress!" Helen said making it
sound as if that was that. Jack's tongue hurt from biting
it again.
They left an hour and a half after they arrived. Helen
would be back first thing. He would wear that light pink
one with the pretty slip at the meeting. Another full slip
under that. A soft chiffon petticoat over that, nylons of
silk, his training bra, shoes and the ruffled lace socks he
hadn't seen. And those panties... A bit much for a girl and
just enough for a boy.
The two women hugged. It had been a delightful evening as
Helen noted, while Jack waited out front, I've still got to
put his little panties together. Mary understood, made her
promise a lunch soon and smiled over her sale. Another
Little Miss Priss in the making she thought as she closed
the lights.
Chapter Fifteen
"You'll have to remove those!" The large woman said as Jack
hung his pants on another hanger next to his shirt.
"Excuse me?" Jack asked getting ready for his waxing.
"Those shorts. You can leave them on if you really need to,
but you'll have to role them down. I wax for bikini's!" The
woman said as she moved a stick in a cup of goo just
starting to smoke a little.
"I don't wear bikinis!" Jack said feeling slightly miffed
that the women might think that he did.
"Okay! But I still wax for one, so roll those or remove
them, or go tell the lady at the desk you've cancelled your
appointment?" The large woman said. Jack rolled his shorts
down till he was wearing a bikini of sorts.
That first application of, the almost too hot, wax scared
him the most. His ouch came quickly but the wax cooled just
as quickly. Although another "ouch" came with a "damn"
added, a second later, when the woman laid down a strip f
gauze before ranking it off his leg.
An hour of "ouch's" and damns' went by, but you could drag
a piece of pure silk across Jack's body and not get a snag.
Which was exactly what that woman was going as she worked
at touching up this spot or that. It wasn't exactly torture
that silk part, and Jack might have spent more time letting
her doing that but he had other things to do.
He'd been given a complementary silk robe in pink with the
Beauty Boutique logo on it as "all the woman got" for his
makeover. A head to toe, for a woman, was a luxury, and an
event. It was just as luxurious for a man, but they didn't
admit it, and it definitely was an event, but not as it was
for the woman.
Jack had rolled his shorts down and back up again when his
waxing was finished, and wore the robe for the first time
to his mud bath and spa. There are words to describe what
silk feels like on skin made smooth, but Jack avoided
thinking those, and simply gasped a little. A couple of
times, silently, and he was thankful for that robe and the
fact he still had his shorts on.
Chapter Sixteen
Clair had called her most favorite beautician leaving
strict orders that her young man would get the works.
Whatever else, she said, she wanted him walking out dizzy,
confused and as pretty as was possible. Not just pretty but
knock down, drop dead gorgeous. And, as young looking as
Mildred could achieve.
Mildred had laughed. Sometimes, that wasn't possible, she'd
said, but when Jack walked in that opinion changed. So did
the wig she was thinking of after talking with Helen about
his dress. If he looked older than ten she said, she'd quit
doing this for a living. She didn't say that to Jack,
obviously, and there was still two hours before they had to
be at the conference site.
He was waxed, soaked, rubbed, buttered, basted, pampered
and whatever else he thought of as he went though the
process of being feminized. He actually was slightly dizzy
by the time they began working on him in a chair. There was
a woman at his feet, another on his left hand, and Mildred
breathing in his face as she began his transformation.
The guy, and clearly that could be a discussion worthy of
note, was behind him adding sprays of pink ribbon into a
wig Shirley Temple would have loved. Jack hadn't seen the
wig, nor did he connect it to him when he did. There were a
lot of wigs on that large shelf that were being worked on.
His only one of them and none of them he'd wear he thought.
He hadn't seen his outfit either, because that was in a
bag. A very large bag, and another, smaller, Helen said
held everything. His new purse was filled by Mildred with
some of the colors she was using or would be. His new
panties, slip and that little dress waited as Jack slipped
slowly into a different world.
"We blend, color and cover!" Mildred said as she moved
about his face with this thing and that. One of those
things was mascara and she waited as he blinked, another
she said was blush, then liners for his eyes, lips and some
stuff for highlights that he forgot what it was called.
His hands were softened, his fingernails lengthened, and
his toes were a very pretty pink when he looked down. Why
he had to have his toes painted since he'd be wearing socks
and shoes was a question he would have like to ask. He
didn't. He did panic when that guy moved in too close, but
he'd always had a bit of a phobia about guys like that.
He also panicked over his new hair that guy was holding.
There were ringlets. Curls and ringlets woven with tiny
bits of ribbon that fell right and left of those curls.
Long curls, short curls, and those images of girls in the
South came to him. The image of Shirley Temple came to him
and he almost cried.
He could use the back room to dress in Mildred had said,
and said it again, as the group began backing off. There
was five of them waiting for him to stand and admire their
handiwork. Five of them, and that guy smiling at him made
it worse.
Actually it was his wink that mostly scared him. Guys don't
wink at guys like that Jack thought.
Chapter Seventeen
A thought, which went suddenly away when Jack turned. Guys
do wink at girls like that Jack thought before closing that
path. He actually looked back to see "her" in real life
before that second it took to realize she was he. Or in
this case he was now most definitely a she.
There was nothing of Jack left that Jack recognized. Not
the eyes that fluttered at him or those soft puffy lips
that glistened in the light. Nothing. He was stunning or
she was and that confused him some as he kept bouncing back
between those definitions.
Clothes do make the man! Jack thought and sadly, he noted,
they can undo the man just as fast.
How can "you" turn "you" on he thought with a touch of
dismay. It was like looking at this cute little fox,
getting all hot over her, registering all of that and on
the one hand, while your brain kept telling you don't go
there. Don't bother. She's not available you idiot, because
she's you. That little fox is you!
Little fox Jack thought.
He felt that twinge of panic again if that was possible,
since that first twinge was still there. He was a little
fox. Jail bait! He looked like jail bait. Heaven help me!
He thought. What would everyone think? What would those
guys think?
It's one thing to spoof a woman, and dress like one, but a
whole different thing to actually look like one. And he was
a step or two past that. Guys don't look like that even on
Halloween unless they are guys like that damn guy still
smiling at him.
"Ready?" Helen said holding back some of what she wanted to
say.
"NO!" Jack said.
"Good. Your stuff is all set!" Helen said completely
ignoring Jack's "no" and the tone he'd used.
Chapter Eighteen
"That's not the dress you said I was going to wear that's
the one with the... I mean that's the other one!" Jack said
fighting back that comment about the silky slip on that
one. It was a slipper satin Helen had said. Jack didn't
know what slipper satin was, but he knew the difference
between that one and the cotton ones. He'd felt them both.
"I know. It's just that this one was so much prettier!"
Helen said. Mildred, meanwhile, was gathering up Jack's
clothes and placing them in a bag as Clair walked in.
Jack, according to what he remembered, thought he was
riding with Helen to the conference and in a way he was.
Only Helen wasn't driving. She would be riding with her
little girl in Clair's company car.
Jack also saw the panties and that was the last straw. "Not
now, not ever, and that's that!" He said folding his arms
over the pink apron. He looked like a little girl pouting
and Helen smiled.
"Hey! You guys ready? We haven't got all day?" Clair said
on the other side of the curtain.
Jack's panic was evident, and Helen held a finger to her
lips as she said: "Almost, he's just starting to dress!"
Helen took that second to hand Jack his new panties, and
Jack didn't say another word as he dropped his and put that
pair on. He'd gone this far and it was too far but that job
loomed over him still. His job.
He did moan or thought he did, and worried over that, and
was thankful he'd left his robe on as he stepped into the
panties and brought them up under the rustle of his tunic.
Or kind of thankful since the robe moved over the back of
those panties enough to notice.
The rest he did by the numbers as Helen made him leave the
safety of his robe for his bra. A little girl's bra and a
"B" cup if those little bits of foam meant anything. Which
seemed so as she helped him into it.
His full slip followed. It fell to his legs touching them
as it settled. It moved across his stomach a bit then again
over the front and back of his legs. He understood the
advantages of smooth skin in an instant. Smooth skin and
something silky.
His socks followed and sitting had a whole different
meaning in those panties and that slip. His shoes next and
Helen helped with his straps. The full slip to his calves
as he sat, teased them when he stood again, and the
bellowing petticoat was next. Helen cinched it before
gathering his dress in her hands.
She would have preferred longer time for these things but
there wasn't much time. "Getting there can be far more fun
than being there!" she liked saying. She did toy with his
last slip a bit but that was for her benefit rather than
his. Finally she showed him how to hold his arms up so she
could guide those layers over his hair and a second later
they too fell around him.
Around him he thought, and this time Helen did close the
zipper. It was that lining of the bodice over the slip that
teased the bra against him and he had no idea how sensuous
fabrics could be.
The dress, once on, had caught his attention which, till
then, had been focused on the slip touching his legs, which
drifted from his thoughts on his panties. He felt like one
of those steel balls in a pinball game and Helen was using
those flappers on his thoughts. She was in a way and had
racked a lot of points in her favor when the zipper closed
The sash again making it more intense as Helen fashioned
the bow. There were noises coming from all over him as
well. Swishing no matter how slight he moved and a couple
of times he did try moving a leg a bit.
The pinafore was last and Helen almost cried as she moved
back around the front. He was so cute, and she said as much
as she lightly pinched a cheek then spent a second
smoothing his foundation back.
Chapter Nineteen
"Hey!" Clair asked.
"Ready or not!" Helen said.
"Oh my heaven's!" Clair said stepping back while a hand
clutched her breast as she added: "This can't be! That is
not Jack! That is some pretty little girl you've brought in
to pose as Jack! Isn't it?"
Those, to Jack, were not complements, but he smiled in
spite of himself. There was a wall that jetted out a few
feet in front of him. That wall was covered in mirror tiles
and Jack was filling them. Or that little girl that had
been Jack was filling them.
He could, on one level, understand Clair's surprise,
because he was just as surprised. So too everyone else who
had formed with Clair waiting, and that damn guy again.
Like mothers and aunts admiring a girls first time all
dressed up and wearing nylons of all things.
Did they feel like this? Jack wondered.
"Jack! Jack! Jack!" Clair said and then added: "If you'll
agree to a sex change, I'll pay for it and then adopt you!"
Jack looked at her in panic.
"Hey, just kidding!" Clair said but then added: "NOT!"
"I'll get his purse!" Helen said looking at Mildred who
stood frozen with her mouth open.
Mildred didn't get the cue but said: "Damn! I'm good!"
Helen was looking at her and suddenly she caught on. "Oh,
right!" Mildred added.
She had put lipstick, blush and a tiny bottle of Lov's Baby
Soft spritz in it along with a hanky, and on Helen's
suggestion, a small feminine product still wrapped.
When Mildred had looked at Helen in that odd way Helen
said: "For later, when he opens his little purse to freshen
his lipstick. Scares the hell out of them."
Mildred laughed and nodded and said: "Scared the hell out
of me the first time I saw one of those!"
"Come on or we really are going to be late!" Clair said as
she took the little pink purse from Mildred and handed it
to Jack. Jack took it and blinked as a camera went off.
Helen had been taking pictures all through the process. She
promised they'd be safe with her, and he would have his own
set. Jack didn't want pictures.
Chapter Twenty
Barny stood outside in his black suit and cap and
immediately moved to the curb side door of the car to
opened it. "Ladies!" Barnie said that without a thought.
Barnie didn't know Jack, nor that it even was a Jack and
added: "Hello sweets!"
Jack didn't answer as he followed Clair into the large open
area of the back seat. He did have enough forethought to
lift his dress up before taking that step. A gesture Helen
noted as he did so. "Gather your skirts my dear!" Clair
said as Jack turned to sit. Clair took his purse so he
could do so.
Jack sat between the two women as the large black car eased
into traffic like a large ship leaving port. The group from
the beauty parlor waving as they pulled away and that guy
blew him a kiss. Jack hated guys like that as he moved his
legs just a tiny bit to the right and left.
The large sedan moved away from the curb and everyone was
waving. A half dozen bi-standers stopping over the crowed
that had gathered. A couple waved. One woman said to
another that she wished she'd gotten an autograph.
Chapter Twenty One
"Hi everyone! Listen, I said it was okay for Helen's niece
to join us. She's going to be helping Helen. Sort of a
Bring-Your-Daughter-To-Work kind of thing. Hope you don't
mind. Julie honey, this is my staff!" Clair said as she
came into the large rented conference room.
Jack was taken back by the introduction and not sure what
to do, or say, and as he was thinking about it Clair
laughed. There were six in the room when they joined them.
Four women and two men and the women immediately moved
towards Jack
"What an adorable little dress! Daisy? Right?" The first
said.
"Actually it's like a Daisy Kingdom but not!" Helen said as
Jack was still trying to figure out what Clair was up to or
what to say. He did nod yes to her question.
"Okay! Folks, I lied!" Clair said. The small group growing
curious over it.
"Folks, this is Jack! You remember Jack? My young assistant
covering our Europe accounts? He's paying off a bet we
made. He's learning what it's like to walk in my shoes as
it were. That was the bet. Of course I haven't worn those
kind of shoes for a while now. Anyway, we've got a lot of
work to do, so just try and ignore the fact he's a guy, and
let's get started."
"That's going to be easy enough!" One of the guys said.
"Careful Brad! If I remember correctly you came to work in
a dress not too long ago, and I'm betting you've still got
it hidden at home somewhere? What was it? Oh, that's right!
You were Dorothy weren't you?" Clair said laughing lightly.
Brad's mouth closed hard enough that you could almost here
his teeth click. "Right!" He said after a second. The rest,
if they had comments left them to themselves as they moved
to find chairs.
Helen touched Jack's elbow, a moment later, causing Jack to
turn in her direction, and motioned him to follow. The
conference room had a small serving area to the side filled
with a continental buffet and Helen whispered for him to go
ahead and start making plates for the table.
Jack with the deftness of someone with long painted nails
took up a pair of tongs and began picking out iced fruit to
a large dish as Helen did the hot roles. Clair stood at the
head of the room and began writing on a wipe board her
goals for the next quarter. The guys took turns glancing
over at Jack until Clair cleared her throat.
It was just a tad past eleven. There would be a brunch at
two, and if the meeting went past five, Clair promised
dinner. Helen and Jack continued moving about the room with
coffee, sodas when asked, and snacks as the meeting fell
into the agenda.
Jack was almost forgotten by then - almost. There was still
that stolen glance on occasion and a smile, without
meaning, from the girls as the day unfolded. Those guys
didn't smile. Jack wondered about the one that had been
Dorothy. He was sneaking glances at the lace below the hem
of Jack's dress. Jack was guessing he'd like that guy at
the beauty parlor.
Chapter Twenty Two
It was a working lunch and Jack, along with Helen, helped
the two from the hotel serve the salads and sandwiches that
had been ordered. It was the first time Jack had a chance
to sit when Clair insisted they both eat.
Helen didn't miss the way Jack sat, nor had she missed how
he handled long painted nails. He would have done his
mother proud were he a girl, Helen thought, then smiled as
Jack moved a bite of something past his lipstick. He would
be so easy to train. She also thought.
By dinner the trauma, Jack had faced in all of this, had
faded some. Not completely as they filed towards the
reserved table, but some. There was some fresh panic when
Clair insisted he and Helen join them at dinner. A bit more
walking between all of those tables, but by this time Jack
understood how he looked how he looked was exactly as he
looked.
He was a little girl among adults and almost felt that way
as the waiter did the honors of bringing his chair back
before pushing it in again. Jack played his part hoping
that by doing so he'd go unnoticed.
That worked for most, but not for Helen. Most men, when
caught looking like this get more masculine acting. Jack,
on the other hand, got more feminine. Delightfully so.
Helen was already convinced that Jack would make a cute,
and very well behaved submissive. He was doing so well as a
little girl, and those subtle moves he made when he thought
no one was looking thrilled her as much as it had be
thrilling him.
Dinner, for the most part was uneventful and Jack had
almost fully adapted before nature called. There was that
renewed panic at being so public in such a private need but
he wasn't about to go the little girl's room by himself. It
was Helen who stood before Jack did.
Chapter Twenty Three
"Need help?" Helen asked.
"NO!" Jack whispered loudly as he locked the door to his
stall. They were alone, and Jack did his duty as quickly as
possible. He spent a few minutes making sure his layers
were down and a couple of those moments making sure his
panties were up.
"Freshen up honey!" Helen said nodding at his purse.
"What?" Jack asked.
"Lipstick my dear! Needs a new coat." Helen said.
"Oh!" Jack said understanding suddenly, as he opened the
small clutch he carried. It was right at the top, that
feminine product Mildred had slipped in. Jack felt total
panic seeing that particular item and not expecting it. He
didn't even want to touch it, but had to for the lipstick.
"Just in case!" Helen said.
"Just in case of what?" Jack asked just as a woman walked
in. A stranger. She nodded, but didn't go to a stall,
instead, joining them at the counter. She too was
freshening up. She smiled at Jack, and Jack smiled back but
frightened and panicked over her seeing the applicator in
his purse.
"Go ahead honey and just do like I showed you!" Helen said
urging Jack on to finish his lipstick.
"I was so thrilled when my mother allowed me to wear
makeup. Isn't it fun?" The woman said before moving her
lips together. Jack nodded, smiled lightly, but felt faint
and quickly found the lipstick. He twisted it up after
taking the top off and did the same thing she did.
They all left together but the woman told Jack he was very
pretty as she spun off in a different direction outside the
door than Jack and Helen. Desert was on the table when they
returned and Jack performed a perfect combination of moves
to gather his skirts and sit. It was fluid and Helen's
heart fluttered.
Chapter Twenty Four
"Drop these guys off first then take me home James!" Clair
said to her driver Barnie as he opened the door. It was
almost ten. Jack let out a sigh that left the women
wondering if it was relief or the things he wore.
"Jack! You're the man!" Clair said giving him a high five
before she ducked into the car. It left Barnie watching
with a curious look as Jack returned her gesture. Helen
almost patted his bottom when he bent to join Clair in the
car.
"Jack, you're off the hook! I've got a good start on the
numbers anyway, so I'm canceling tomorrows meeting. You did
as promised and I'm proud of you. You may also keep that
outfit, and if you don't mind I wouldn't mind seeing it on
Halloween again. I'll also pay for your makeover again.
Anyway, that took a lot of guts and you've got my respect
for doing this!" Clair said as Helen and he left the car.
It was the look on Barnie's face that made Clair add: "Long
story! I'll give it to you on the way home. If you don't
mind turning around, and taking me there!"
Jack stood with Helen in front of the closed beauty shop
and a thought struck, as he remembered not gathering his
clothes before leaving. "My stuff is in there?" He said to
Helen. Helen looked concerned.
"Okay, don't panic! They'll keep it for you till tomorrow.
Look, come home with me and you can use my guest room.
You've got to get out of those things anyway and I'll fetch
your stuff first thing. I can drive you home after you're
dressed." Helen said.
"Thanks!" Jack said letting another moment of panic pass.
He didn't know that Helen already had his "stuff" in her
car. She'd put it there as he was getting his wig on. She'd
do just that in the morning but she wanted this time left
of the night as they walked to her car.
Chapter Twenty Five
Jack stepped into the silk bottoms of Helen's pajamas. They
were pink and satiny but after that day almost masculine
compared to what he'd been wearing. There was even a twinge
of regret as that little girl ebbed away with Helen's
makeup remover. His wig still sat on her bed along with his
dress, slips and those dainties. He wouldn't mind keep
those either, he thought, as he slipped Helen's light nylon
robe over his borrowed pajamas.
Helen was careful of the process she was working through,
choosing those pajamas as part of it. The kiss when it came
was almost motherly before she said: "You really were a
trouper! I mean it. And as cute as I've ever seen. So be
honest with me - please. Was it horrifying or a little
fun?"
"Both!"