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Why I'm Not A Cross-Dresser
    I
couldn't believe
that
the Captain had
asked me to go undercover as a transvestite.
I figured if I had to dress up as a dame, my
best bet was to enlist the aid of Maggie, my
sweetie.
After supper, I saw my opening.
“So what exciting things did you do
today?” she asked.
“I’ve got something to talk to you about
and I don’t want you to interrupt me or ask any
questions until I’m completely finished, OK?”
Her
look
of
bewilderment
turned
to
astonishment and finally to amusement as I laid
the whole story on the table.
I could tell she was doing her best to keep
from laughing.
“You think this is funny, don’t you?”
“Well, yea!”
Not exactly the reaction I was expecting.
“I’ve always wanted a girlfriend I could
shop with and share make-up secrets. This is going
to be fun.”
Yeah, a real hoot!
For reasons I’ll never understand, Maggie
attacked her role with a vengeance. She composed
a list of all the accoutrements we would need for
my transformation and then started checking off
items she had on hand.
Apparently, women are
loath to throw
away make-up, even if it’s stuff they haven’t used
for ages and Maggie produced a plastic tub full of
jars and tubes that she pronounced as perfect.
Evidently
the
same
rules
apply
with
selected articles of clothing. Maggie is a svelte
120 pounds now, but sometime in the distant past,
she must have been a few pounds heavier. A box
from the spare room closet labeled ‘save’
contained frilly relics from her heftier days.
After comparing items on hand with her
inventory list, Maggie was satisfied that the only
articles we were lacking were a dress, shoes and a
wig.
Tomorrow, we would shop.
Just to be
sure
everything
was right,
Maggie
insisted
on
a
trial
fitting
of
the
undergarments and proceeded to pull a pair of
lacey panties, a bra and pantyhose from her stash.
“OK, Buster, strip.”
On more than one occasion, those very
words from Maggie were music to my ears.
Not this time.
I’m definitely not a prude, especially when
it comes to Maggie, but I’m more accustomed to
us getting nekkid together.
“I’ll just do this in here,” I
said as I
grabbed the panties and bra and headed for the
bathroom.
As I slipped off my BVD’s and picked up
the panties, I encountered my first dilemma.
Is there a front and a back to these things?
How can you tell without a fly? Then I saw the
little tag and assumed that was the backside.
So far, so good.
Next came the bra.
My previous experience with this garment
had focused on removal rather than installation
and I nearly dislocated my shoulders trying to
hook the damn thing behind my back.
I concluded that one had to be either a
contortionist or double-jointed to master this, and
I, being neither of those, gave up and retreated to
the bedroom.
I explained my problem to Maggie and she
gave me a quick lesson on ‘hook in front and
rotate to the back’. A valuable lesson.
Since my chest wasn’t exactly designed to
fill the size ‘C’ cups, Maggie augmented my
bosom with wadded up pantyhose.
While in the pantyhose pile, she selected a
dark pair she described as ‘smoke’.
“Try these on. I think they’re dark enough
you won’t have to shave your legs.”
“You damn right I won’t. That’s where I
draw the line. I’ll just tell people I’m from
Sweden.”
She handed me the pantyhose and I looked
at the tiny ball of material.
“That’s not big enough for one leg. How
am I going to get two, plus my butt in there?”
“Just put them on. Trust me. They
expand.”
So I sat on the bed and started pulling them
up one leg at a time and sure enough, they did
expand.
But as I stood, I was beginning to get
signals from Mr. Winkie and the boys.
“Kind of crowded in here,” I complained.
“Yea,” she quipped. “Pantyhose are a lot
like cheap hotels --no ballroom.”
She was having way too much fun