I
grabbed a bagel and a cup of coffee at the station and wolfed them down on the
train, absent-mindedly flipping through the Tribune. My heart stopped when I
came to this article:
PROMINENT
BROKER ARRESTED
CHICAGO – Norman Wolf, CEO of Piranha and Wolf, has been charged by federal
authorities with bilking thousands of elderly investors throughout
Chicagoland. Wolf, who was taken into custody last night at his Lakeshore Drive home, proclaimed his innocence, maintaining that a rogue employee masterminded
the scheme for his personal self-enrichment. Authorities declined to identify Wolf’s
alleged accomplice, stating only that their investigation was ongoing and
additional arrests were expected.
My
hands were shaking as I dropped the paper to the floor. When I questioned him about
some questionable activities I’d come across working late one night, Norman Wolf
had assured me that everything was on the up-and-up. He even took me out to
lunch one day and involved me in some of his dealings. Now, I was convinced
that he was setting me up, and that he would try to finger me to save his skin.
Furtively,
I glanced around the train, expecting to see policemen heading my way with guns
drawn. But there were only the other passengers, either engrossed in their
papers or asleep, as we pulled into Clybourn, the last stop before Chicago. If the cops were onto me, they’d be waiting at the end of the line. Without
thinking, I vaulted over the passenger next to me and raced for the door, just
making it out onto the platform before the train pulled away.
Shivering
in the freezing February gloom, I tried desperately to think. Going back to my
apartment was out of the question. Until I could figure out a way to clear
myself, I’d have to lay low, keeping out of sight until the heat was off. Fortunately,
I had no family or close friends in Chicago, only my girlfriend Tracy, a flight
attendant who lived with two other girls in an apartment near O’Hare. I
flipped open my cell phone and punched in her number.
“Hello?”
a groggy voice answered.
“Tracy, it’s me.”
“God,
don’t you know what time it is? I flew all night and I just got to sleep.”
“Sorry,
baby. Are your roommates there?”
“No,
you didn’t wake anyone else up. Just me, and I’m gonna hang up.”
“Tracy, I’m in trouble and I need your help.”
It
took some doing, but after a long walk to Armitage I caught the “L” downtown
and rode the Blue Line out to the Rosemont station, a few long blocks from Tracy’s apartment. I don’t know which of us was more frazzled when she finally let me in.
Standing there in her robe without any makeup, even after working all night,
she was a sight for sore eyes.
“Thanks
for taking me in,” I said after a long hug. “Are you sure you want to harbor a
fugitive?”
“Are
you sure you’re doing the right thing?” she replied as she poured us each a cup
of steaming black coffee. “Why not just turn yourself in? The FBI will
believe you if you tell them the truth.”
“You
don’t know Norman Wolf. All the way here I’ve been replaying little scenes at
the office which didn’t make sense to me before, but they do now. He was
setting me up all along, Tracy.”
“Well,
what are you going to do?”
“I
need a disguise and a place to stay until I can figure things out.”
“You
could stay here, I guess…”
“What
about your roomies?”
“Cathy
just left for training in Denver, and Ashley is on vacation till the end of the
week.”
“That
works. Now all we need is to come up with a disguise, something that will
enable me to move around until I can clear my name.”
“Hmm…”
Tracy walked around the room, surveying me with a critical eye. “Stand up and
take off your jacket,” she said, disappearing into the bedroom.” I did as I
was told, and she returned with a tape measure. “Raise your arms,” she said,
and I stood there while she drew the tape around my chest, then around my
waist, then once more a little lower. “How tall are you?”
“Five
nine.”
“How
much do you weigh?”
“One
fifty.”
“And
your shoe size?”
“Nine.”
“Perfect,”
she giggled. “Come with me.” I followed her into the large walk-in closet
that she shared with the other girls. It was crammed full of clothes, shoes
and accessories. All of a sudden it hit me, and I backed out of the closet in
a panic. “Come back here!”
“No
way!” I trembled.
“Listen,
mister, you asked me to help you come up with a disguise, and I did. You’ll
fit into my clothes, Cathy’s feet are as big as yours, and Ashley has a wig in
here somewhere that she used to wear on layovers.”
“I’m
not gonna dress up as a chick!”
“Why
not? Are you afraid of what people might think?”
“Damn
right!”
“Well,
let’s see how you look first. When I’m finished with you, I don’t think
anybody will be able to tell that you’re really a guy.”
“Yeah,
right,” I said nervously. Maybe that was what I was so afraid of, afraid that
my masculinity might be threatened. Had I only known, I’m sure I would never
have taken that first fateful step, but I was desperate, Tracy was sincerely
trying to help me, and what choice did I have?
“May
I take that as a yes?”
I
hung my head in resignation. “I guess we can try it,” said with a sigh.
“Attagirl.
Now, if this is gonna work we’ve gotta start from the skin out. Take off all
your clothes.”
“Okay,
but what do you mean ‘from the skin out’?” I asked as I unbuttoned my shirt.
“I
mean this has gotta go,” she said with a tug on my chest hair.
“Oh
no, you don’t!” I protested.
“Listen,
silly, if you expect me to make you believable as a girl, you’re gonna have to work
with me.”
“I’m
sorry, Tracy, but I’ve changed my mind.”
“Suit
yourself,” she said in a huff. “I’d just as soon go back to sleep anyway.”
She tossed my shirt at me, and I was buttoning it back up when the telephone
rang. “Hello?” She shot me a hard glance. “Uh, no, I haven’t seen him,
why?” Her eyes widened. “Really! Wow, that’s unbelievable, thanks for
letting me know.” She hung up and grabbed the TV remote.
“What
was that all about?” I asked.
Tracy ignored me, flipping through
the channels until she came to a local news station. We both stared speechless
as my picture came up on the screen. “According to the FBI, Matt McCoy is
suspected of masterminding a scheme to swindle thousands of elderly investors
out of their life savings,” a reporter was saying.
I
felt sick to my stomach. “This can’t be happening.”
“Just
be thankful that you found out about it before you walked out of here,” she
said. “You knew this was coming down. Matt, are you sure you’re telling me
the truth?”
“Tracy, you’ve got to believe me!” I started to cry, and she took me into her arms.
“I’m
here for you, baby,” she whispered.
“I’m
sorry I was so stupid. Please help me. I’ll do anything you say.”
The
bathroom in Tracy’s apartment was strewn with nylons hanging out to dry. They
might be falling out of fashion, but not in an apartment shared by three flight
attendants. Tracy wore pantyhose every day as part of her uniform, and soon
I’d be wearing them too, I thought morosely as I shaved my legs in her
bathtub. My arms too, then my chest and underarms, and finally Tracy came in to finish off my back. “You look buff,” she said after I toweled myself
off.
“You
mean you like me this way?” In spite of all I’d been through, I felt myself
starting to stir.
“You’re
just like a movie star,” she purred. “Besides, I’ve always wanted to make love
to a wanted fugitive.” I chased her into the bedroom and we tumbled into bed.
The feeling of our smooth bodies touching was incredibly arousing, and we went
at with abandon. Tracy had always been a gentle lover, but today she was like
a tigress, with some newfound power. “Wow,” she sighed when we finally came up
for air.
“Let’s
do it again,” I said, even though my body was totally tapped out. I dreaded
what was about to happen to me.
She
teased my exhausted manhood. “Now that I’ve softened you up, we’re going to
turn you into a girl,” she pronounced. “Come on, get out of bed. We have some
serious work to do.” With a sigh, I got up and we put on terrycloth bathrobes
which she’d stolen from some hotels. After I shaved my face again, Tracy was all business. First she went to work with an emery board, smoothing and shaping
my longish nails. Next, she tweezed my eyebrows, and when I yelped she told me
to stop being such a baby. She helped me moisturize my tender skin, and then
it was time to get me dressed.
“What
am I going to try on?” I asked nervously.
“Let’s
start with one of my old uniforms. I used to be a little chubby before I met
you, so it should fit just fine.”
I
cringed at the thought. “Don’t you have something more casual?”
“Listen,
missy, I’m a working girl and my wardrobe is somewhat limited. Once we find
out whether you’re presentable, maybe we can do a little shopping, okay?” That
shut me up, and I reluctantly followed her back into the closet.
“Your
hips are slim enough for you to wear my panties,” she said matter-of-factly. I
cringed when she handed me a lacy white pair, and I watched her smirk as I
tugged them on. “There, that wasn’t so hard, was it? This may seem a little
strange,” she said as she handed me one of her bras. I watched sullenly as she
draped it over my chest and showed me how to fasten the clasps from behind.
After Tracy stuffed the cups with some knee-highs, she pushed me over to her
vanity and went to work on my makeup. I watched with alarm as she methodically
feminized my face, leaving me with smoky eyes and pouting pink lips.
Next
came Ashley’s wig, and the effect was shocking. One minute, I was a guy in a
bra and panties, and the next, I was totally a girl. I could only gape and
stare as Tracy gently styled my short blonde hair into a perky wedge.
Tracy seemed mesmerized by her
creation. “This is scary,” she whispered.
“Tell
me about it.” How could it be so easy to erase my gender? I followed her back
into the closet in a trance.
“Okay,
put this on first,” she said, handing me a crisp white blouse. “Oh wait, I
almost forgot.” She left me standing there, surrounded by racks of skirts and
dresses, contemplating my misfortune. When she returned she was holding a lacy
white slip. “This will help to smooth you out,” she said. “No, don’t pull it
over your head, you’ll muss your hairdo. Step into it.” Reluctantly, I did as
I was instructed, and a shiver ran down my spine as the cool, silky fabric slid
up my hairless body. “That’s better, now put on your blouse.” My hands were
shaking, and I fumbled helplessly with the buttons until I realized that they
were backwards from what I was used to. Eventually I figured them out, and
although the blouse was a little tight around my shoulders, the last button
left me with just enough room to breathe.
“Time
to put on your nylons,” Tracy said with a snicker.
“Do
I have to? You never wear them when we go out.”
“I
do when I go to work. Besides, they’ll make your legs look more feminine.
Anyway, they’re part of your uniform, so get with the program!” She handed me
a pair of navy blue pantyhose and showed me how to ease them on, one leg at a
time. After that, my blue skirt was almost an anti-climax, and I felt trapped
when she zipped it up.
There
was a full-length mirror on the back of the closet door, and I watched my
reflection in dismay as Tracy lifted up my skirt and tugged down my blouse and
slip. Then it was time to step into a pair of Cathy’s low-heeled blue pumps,
which just fit. “We’ll practice walking around in them in a minute,” Tracy said as she tied a silk scarf loosely around my neck. A blue jacket was next, and
again it was a little tight around the shoulders but it buttoned up all right.
“Almost
done,” Tracy said. I followed her over to the dresser, and stood there in her
clothes while she tried some jewelry on me. “I can’t remember who gave me these
clip-ons,” she said as she fussed with my earrings, and a simple gold necklace
and an inexpensive woman’s watch were next. Then she sat me down at her vanity
and started to apply a coat of quick-dry polish to my nails. As I sat there, I
looked down at my silken knees, peeking demurely under the hem of my slim skirt.
Never in my life had I felt so helpless and confined.
When
my nails were dry, we went back to the kitchen and Tracy made some more
coffee. We sat there for a while, sipping our coffee in silence, while I
gradually got used to the strange sensations of wearing women’s clothing. “I
can’t believe how cute you look,” Tracy marveled.
“Thanks,
that’s all I needed to hear.”
“Take
it as a compliment. If you looked like a guy in a dress, this disguise would
never work. Now, if we can only do something with your voice, I really think
you can pull it off.”
“My
voice?”
“Try
talking a little softer, and raise your pitch a little.” For the next half
hour, we chatted like two girls as she worked on my voice. I was beginning to
get the hang of it when the doorbell rang.
Tracy saw the panic in my eyes.
“Relax, it’s probably just the lady next door. She waters the plants when
we’re all away. Sit still, you look totally like a girl now, it will be a good
test for you.” Before I could protest, Tracy got up and opened the door.
“FBI,”
a deep voice said. “Are you Tracy Flowers? Do you mind if we come in?” Tracy tried to slam the door but it was too late, and two middle-aged special agents in
suits and ties entered the apartment. Tracy was beside herself, and I was
worried that she might give me away. Sheer instinct for self- preservation
took over. “Why don’t you go change, Tracy? Can I get you guys some coffee?”
Tracy ran into the bedroom and
slammed the door. “I’m sorry we barged in on her in her bathrobe,” one of the
agents stammered.
Keep
it short and sweet, I reminded myself before I spoke. “That’s okay, she’s a
big girl. How do you take your coffee?”
“Black
for me.”
“Nothing
for me, thanks,” the other agent said as he prowled around the apartment. “Do
you live here?”
There
was no time to think, so I just went with the flow. “Uh huh.” I reached up
into one of the cabinets for a mug, very aware that my skirt was riding up my
legs, and after I filled it with coffee I offered it to the agent, trying to
keep my gestures as feminine as possible.
“What’s
your name, sweetie?”
“Ashley.”
In her wig, I looked almost like her, not that they would know what she looked
like anyway…keep your cool, girl, I told myself.
“Do
you know Matt McCoy?”
“Tracy’s boyfriend? I’ve met him, why?”
“Let’s
wait for your roommate.” That was the opening I needed, and before they could
stop me I walked over to the bedroom and closed the door firmly behind me. Tracy was sitting on the bed, still in her bathrobe, shaking with sobs.
“Listen
carefully,” I whispered. “They think I’m Ashley.” Her eyes widened. “You’ve
got to play along. Quick, put on some clothes and when you come back, just
tell them that you haven’t seen or heard from Matt since yesterday. Got it?”
She nodded dumbly. “Come on, Tracy, get with it!”
When
she finally got up to get dressed, I returned to face the agents. “She’ll be
here in a minute,” I said breezily. “Some more coffee for you?”
“You
must be a very good flight attendant.” I ignored the sexist remark and sat
down on the sofa. It occurred to me that the men were staring at my legs. I
crossed them slowly and tugged at the hem of my skirt, waiting for them to make
the next move. Just then Tracy opened the bedroom door, dressed in jeans and a
hoodie. I gave her an encouraging wink, and she sat down beside me on the
sofa.
“I’m
sorry for the intrusion, Miss Flowers, and thank you for your time. When is
the last time you saw Matt McCoy?”
“Last
Saturday.”
“Where
was that?”
“He
took me to a movie, and then we came back here for a while.”
“Have
to spoken with him since?”
“No.”
“Is
that unusual?”
“What
do you mean?”
“Well,
doesn’t he call you on the phone sometimes?”
“It
depends. He knows I travel a lot. I just got back from a trip this morning,”
she answered, trying to keep to the truth whenever she could. I felt so
strange, sitting there in women’s clothing, watching the men ogle my legs while
Tracy described me like I wasn’t in the room. I tugged my skirt down over my
knees again and prayed that she wouldn’t give me away.
“Were
there any messages from him on your machine?”
“No.”
“Do
you know where he is right now?”
“Look,
I’ll be very honest with you,” Tracy said as I held my breath. “One of my
girlfriends called me a few hours ago and told me that Matt was wanted by the
police. I saw his picture on TV.”
“Was
that news to you?”
“Yes!
What kind of girl do you think I am?”
“Did
you try to get in touch with him after you heard about it?”
“No!
Is it true?”
“Is
what true?”
“What
they’re saying about him. Is he really a criminal?”
“We’re
really not at liberty to discuss our investigation.” They handed Tracy their cards. “Please call us immediately if you hear from him. Thank you again for
your cooperation.”
Tracy got up to let them out. “And
thank you, sweetie,” the agent who had the coffee said to me before they left.
Tracy waited until they were well
down the hall before bolting the door and collapsing next to me on the sofa in
near hysterics. I couldn’t tell whether she was laughing or crying, but the
tears were real, and she hugged me close. When I tried to comfort her, she
shushed me with a kiss, and the next thing I knew she was stroking my legs
through my nylons. It was the sexiest thing I’d ever felt, and I started to
lose control as she reached up my skirt and tugged down my pantyhose and panties…then
she had her jeans off and she was straddling me, riding up and down, panting
and yelping until we came together in an incredible rush.
Afterwards,
I lay back in a daze, trying to come to grips with what was happening to me.
I’d just had the best sex of my life, in woman’s clothing, with my girlfriend
on top. My lipstick was smeared all over her beautiful face, and our hairless
legs were tangled up in my panties and stockings. When she finally rolled off
me, I got unsteadily to me feet and began to pull myself together. “You’ve
ruined my stockings,” she pouted, pointing to a long run that ran from my toes
to my waist. “Take ‘em off, and I’ll get you a fresh pair after we fix your
makeup. You’re a total mess!” A subtle shift in our relationship was
occurring, although I was so distracted by my female trappings, I didn’t notice
it at the time.
After
showing me how to put on a fresh coat of lipstick, Tracy handed me another pair
of pantyhose, nude this time. It was humiliating to struggle with them under
her watchful eye. When I finally got them on, she disappeared into the
bathroom to shower and change.
I
stepped back into my heels and stared at myself for a long time in the full
length mirror. Looking back at me was a pretty flight attendant with perky
blonde hair and terrific legs. I turned this way and that, practicing ways to
stand and move my hands to make myself look more feminine. The more I studied
myself, the more convinced I became that Tracy was right: my disguise was
perfect, and with a little practice there was no way anyone would detect that I
was really a guy.
That
brought me back to reality, and I was thinking of ways to get close to Norman Wolf
when Tracy returned to the closet. She had zero makeup on, her hair was pulled
back into a bun, and her bra and panties were soon covered by a thick sweater
and baggy khakis. “Are you trying to look like a guy?” I asked as she pulled
on a pair of trouser socks.
“One
of us has to wear the pants around here,” she taunted me. “I thought I’d take
you out to lunch, then maybe we can do a little shopping so you won’t have to
wear my clothes. How are you fixed for cash?”
“We
got our bonuses in January, so I’m flush…uh oh!”
“What?”
“If
the feds are looking for me, how am I going to get into my bank account?”
“Like
any working girl, use your ATM to take out as much cash as you can every day.”
“Hmm….they’ll
be watching my account, and once they see that I’m using an ATM machine in
Rosemont, they’ll be all over you.”
“This
is true…how about if you write a big check to me, only date it like a week ago,
and I’ll cash it for you?”
“I
really don’t want to get you in trouble, Tracy…say, does Ashley have any ID
around here?”
“Clever
girl! You do look an awful lot like her now. Let’s see, she may have left her
airline credential when she went on vacation, let me check.” Sure enough,
Ashley’s photo ID was in a drawer of her nightstand, and it bore an uncanny
resemblance to me in her wig.
“Okay,
only I’ll have to go downtown to one of the big branches of my bank.” I
retrieved my wallet from the pile of guy clothes on the closet floor and found
the blank check I always carried with me. After I made it out to Ashley in the
amount of $5,000, I was about to stuff it into the pocket of my little blue
jacket when Tracy started to laugh. “Girls don’t carry their money like that,
dear,” she explained. She went into the closet and came back with a navy blue
purse and one of her old wallets. “Here, let’s set you up like a proper
woman.” Soon my purse was chock full female essentials like lipstick, a compact,
a brush, tissues, and a nail file in addition to the wallet.
After
Tracy put on a pair of sturdy shoes, a wool cap and a pea coat, she loaned me
one of her uniform topcoats and a pair of women’s gloves, and we were off. I
was very self-conscious at first, and Tracy had to tell me to smile and act
natural. “Stand up straight…stop staring at your feet!” she scolded me. When
we stepped outside, the winter wind whipped my skirt and coat around my knees,
and the frigid air cut through my stockings like a knife. “Now I know why
you’re wearing pants!” I groaned.
“Better
get used to it, sweetheart. You look like a girl dressed like that, but I
don’t know how convincing you’d be in pants.”
“Whatever,”
I sighed. My girlish voice was becoming a little more natural to me, and we
bantered back and forth to take our minds off my troubles.
“Hungry?”
she asked me.
“Starving.”
“Okay,
let’s find someplace where I can teach you how to eat like a girl.”
It
dawned on me that Tracy was acting more and more in charge, almost like she was
the guy. “You’re digging this, aren’t you?” I asked.
“If
you’re asking me whether I’m happy that my boyfriend is on the ten most wanted
list, the answer is no.”
“But
you are digging the fact that I have to act like a chick.”
“I
have to admit, it’s been a blast so far. Watching you try to pretend you’re a
girl is a hoot, and you gotta admit, the sex was amazing.”
Just
thinking about it made me stir again, which was a very uncomfortable feeling.
I closed my eyes and tried to forget about my manhood, trapped and throbbing in
its silken prison. At least my tight skirt and heels made it impossible for me
to walk like a man, and it was a struggle to keep up with Tracy.
We
arrived at the Rosemont station, and I fished awkwardly through my purse for
money to pay for our tickets to Chicago on the Blue Line. Fortunately, the
station was almost deserted at that hour, and a train came along in a few
minutes. As soon as we found our seats, I kicked off my heels and flexed my
aching toes, which were cold under my stockings. Tracy smiled sympathetically
before she closed her eyes to catch some sleep.
Instead
of looking out for cops, I studied the faces of other passengers for any
indication that they saw through my disguise, but once again everyone else was
either reading or sleeping. As we rolled through the Chicago suburbs, I
actually closed my eyes and nodded off for a few minutes. Without realizing
it, I was getting more and more used to myself as a woman.
We
woke up with a start when the train went underground for the final run into
downtown Chicago, and soon we were making our way through the crowded
concourse, looking for a place to eat. Nothing appealed to us, then Tracy had an inspiration and we rode up the escalator to State Street. Once again, I
cursed my fate as the winter weather knifed through my nylons, and as we made
our way towards Macy’s, it occurred to me that I was the only person on the
sidewalk, man or woman, showing any leg. “Look at me! I’m the only dumb-dumb
in a dress!”
“Poor
baby! We’ll get you some tights and boots after lunch.”
Although
we were both famished, I saw a branch office of my bank across the street, and
I told Tracy to wait outside. She gave me a little kiss on the cheek for good
luck after I instructed her to melt away in the crowd if I was apprehended.
There was a long line waiting for tellers, but it moved quickly, and soon I was
face to face with a young woman who scrutinized my check, then my ID, then me.
“Do you have an account with us?” she inquired.
“No.”
“It
should be all right, since the check is drawn on one of our accounts. It’s
just that the amount is so large, I’ll have to get an assistant vice president
to approve it.” My knees were shaking while we waited for an unctuous man to
appear, but after he looked me over and glanced at my ID he scribbled his
initials and the teller began counting out hundred dollar bills. As soon as
she was through counting it all twice, I stuffed the wad into my purse and beat
a hasty retreat.
Tracy had a relieved smile on her
face when I joined her outside. “Can we add forgery to your list of firsts
today?” she asked.
I
stuck out my tongue at her. “Better be nice to me if you want me to pay for
lunch.”
We
crossed the street again and continued on our way towards Macy’s, still thought
of by Chicagoans as Marshall Fields. After we went through the revolving door
into the vast department store, I gratefully unbuttoned my topcoat and peeled
off my gloves. It was unnerving to see my manicured fingers again, just
another reminder of my newfound femininity, and I got zapped with cologne by a
girl in a white smock as we fought our way past the cosmetics counters.
The
restaurant upstairs was a Chicago institution, and most of the lunch crowd was
gone by then, so we were seated immediately. Tracy taught me how to drape my
coat over the back of my chair, and she suggested that I visit the ladies room
to repair what the wind had done to my wig. “Does it look funny?” I asked.
“No,
you just look like a girl who’s been through a force ten gale. Now you know
why I wore this hat.”
I
had so much to learn about being a woman!
Fifteen
minutes later, I rejoined a very impatient Tracy at the table. “Where have you
been?” she steamed.
“Well,
let’s see…first I had to wait for a stall…”
“You
needed a stall to comb your hair?”
“Please…nature
called, and after I scored a stall, it took me a while to figure out how to get
my panties and pantyhose down far enough to sit down, while holding up my slip
and skirt of course…what a hassle!”
“I
hope everything came out all right,” she said sarcastically.
“Yes,
darling. It did take me forever to put everything back together, and then I
went to work on my hair…it looked like a fright wig! I almost pulled it clear off
my head, which would have been a little embarrassing, considering the crowd
that was in there, although none of them had a clue. I think I’m beginning to
get the hang of this. How do I look?”
Tracy backed off. “You look like
you’ve been a woman all your life,” she said. “Believe me, I know girls who
would kill to have your figure, and who knew that your face would paint up so
pretty?”
I
must have blushed, and once again I had the nagging feeling that I was getting
way too good at this…what kind of a man was I? A waitress materialized before
I could think of what to say, and we busied ourselves with the menus. I
followed Tracy’s lead and ordered a salad and iced tea, something a girl would
have for lunch. When we were alone again, Tracy launched into her lesson.
“Cut your food into little pieces…always ask for the dressing on the side…leave
something on your plate…” On and on she went, schooling me on the ways of
being a woman, from etiquette to fashion, even hygiene and how to watch my
weight. It was so strange, sitting there with her like another girl, feeling
more and more like I was becoming one.
When
we were through with our ladies’ lunch, Tracy insisted on picking up the check,
then she steered me back to State Street for the short walk to Filene’s
Basement. There, I was overwhelmed by the endless racks of skirts, tops and
dresses, as well as accessories, lingerie and outerwear. We must have spent
two hours trying outfits out on me, after I overcame a panic attack waiting for
the sentry in the fitting room to give me a plastic number indicating the
number of items I was carrying. Soon I was the proud owner of a complete
woman’s wardrobe: panties, bras, skirts and dresses, tights and tops, coats
and sweaters, even a nightgown with a matching robe to sleep in. Just when I
thought we were finished, Tracy dragged me to a Payless shoe store where I
tried on and bought several pair of flats, heels and boots.
Our
final stop was Walgreen’s, where Tracy helped me stock up on foundation,
powder, eyeliner, nail polish, shadow, blush, lipstick and mascara, as well as
an array of brushes of sponges and a cosmetics bag to put them in.
I
was totally exhausted by the time we made our way to the underground concourse
to catch the Blue Line back to Rosemont. The train was crowded with commuters
this time, but we were able to find two seats together, and once again I dozed
off as we streaked through the gathering dusk. When we got to our stop, we
buttoned up our coats and slogged our way back to back to Tracy’s apartment, laden
down with shopping bags, feeling exhausted, exhilarated, and slightly silly. Tracy uncorked a bottle of wine while I tried to find space for my new things in her
crowded closet and dresser.
“We
forgot to get me some bling,” I said when I joined her in the kitchen.
“What
would you like, a diamond tiara?”
“No,
it’s just that you know, I hate to take your stuff….”
“Girlfriend,
I’m just happy that you’re not wearing my clothes. If you want to keep those
trinkets you’ve got on, be my guest, although I do think you should have your
ears pierced.” I ignored the suggestion, not wanting to go there…it seemed so
permanent! “We should put a ring on your finger, so the guys don’t hit on
you….”
“Sh’yea,
right!”
“I’m
serious, missy,” Tracy said as she poured us each a glass of wine. “In case
you don’t know it, you are seriously hot, and I’m surprised you haven’t been
hit on already.”
Tracy fixed us a salad, and then
some pasta, while we gabbed through the night about girl stuff. After two
bottles of wine, and some Ben and Jerry’s ice cream, we were ready for bed. It
felt great to take off my girl’s clothes and cream off my makeup, and even
better to slip into my nightgown and crawl into bed beside Tracy…that night we
had the most glorious sex of our lives, taking turns pleasing each other, crying
out in ecstasy as we each went to places we’d never been before.
When
we were both sated, Tracy lit up a Benson & Hedges and we shared puffs
contentedly. “That was amazing,” she said. “Can I ask you a question?”
“Anything.”
“Do
you think I could pass as a guy?” That totally threw me. What kind of weird
hang-up was this? Then again, who was I to talk? “I don’t mean that I want to
be a guy,” she went on, “but seeing you like you were today makes me wonder
whether I could pull it off like you.”
Something
told me there was more going on beneath the surface. “I don’t know…I think
you’re too pretty.”
“Thanks,
but what if I had a fake mustache or something.”
“Then
you’d look like a fairy with a mustache. Is that what you want?”
“No!”
she punched me in the arm. “I guess I’ll have to content myself with being
your lesbian lover.” For some reason that turned us both on again, and we made
slow, sweet love until our bodies were utterly spent.
The
next morning, Tracy fixed breakfast while I shaved, bathed and dressed in one
of my new outfits. I decided on my plaid kilt, turtleneck and tights,
accessorized by a gold chain around my waist. After I pulled on my
calf-length boots, I studied my reflection in the mirror. If anything, I
looked more like a girl than yesterday. What in the world was happening to me?
“Let
me see you,” Tracy said when I sat down to breakfast. “Hmm…your makeup isn’t
bad, and your hair looks nice…wow, I love your kilt, it looks so cute with that
sweater. You really should have been a girl, you know.”
Once
again, that nagging suggestion that I was getting way too good at this…I
dismissed the thought and focused on the matters at hand. “When’s your next
flight?”
“I
have to leave for the airport at six, why?”
“Because
my plan is to lure Norman Wolf back here tonight to get the truth out of him.
According to the paper, he just made bail, and if I know Norman, he’ll be on Rush Street getting drunk.”
“Lure
him? What, are you gonna put on a cocktail dress and come on to him at a
singles bar?”
“You
got it…he’s divorced, and he hangs out at Gibson’s most nights when he’s in Chicago.”
“You
go, girl…only what are you gonna do if he tries to get into your pants?”
Tracy
and I spent the day shopping for a dress for me. It wasn’t easy to find a
slinky dress that looked good on my body, but eventually we found a little
black number with spaghetti straps that made me look like I’d been poured into
it. I splurged on some sexy lingerie, a clutch purse, strappy heels and some
fashion jewelry, and we even found a fake fur at a thrift shop that looked like
a million on me.
Tracy surprised me with a trip to a
nail salon, which left me with sharp red talons to use on Norman Wolf. Our
last stop was a store which catered to mastectomy patients, where she helped me
buy the most amazing set of silicone breast forms. I tried them on as soon as
we got back to her place. I couldn’t believe how they made me look so hot and
feel so girly.
Tracy liked them too, and before
she got ready for work, she coaxed one last orgasm out of my bewildered body. By
the time she was in her uniform, ready to leave for her flight, I was
luxuriating in a bubble bath, psyching myself up for the night ahead.
“Good
luck, girlfriend,” she said with genuine concern. “Wish I could be there with
you.”
“You’re
the best, baby,” I said from behind a wall of bubbles. “I couldn’t have done
this without you.”
She
reached down and kissed me gently on the lips. “Please be careful! Remember,
you’re only a girl.” Then she was gone, and I wallowed in the tub for a long
time, missing her as well as the man I used to be.
It
was with real foreboding that I climbed out of the tub to prepare myself for
the night head. After drying off and moisturizing, I took a long time with my
makeup, adding a few flourishes for evening that Tracy had taught me. Before
she left, she shampooed my wig, and I was freaked out by how ratty it looked
before she brushed it out. Now, it looked better than ever, and in no time I’d
styled it into a perky wedge.
My
new dress called for a strapless bra, and I felt forlorn as I tucked myself
into my matching black panties. Sheer nude pantyhose were next, then a lacy
black half slip, and finally my dress, which looked sensational on me. I was
shaking with anticipation as I sat down on the bed to strap on my heels, then
it was time for some bling and a shot of Tracy’s expensive cologne. I stuffed
my little purse with female essentials, and when I wrapped my fur around my
shoulders, the look was complete. God, I looked hot in the full length mirror!
There
was no way I was taking the subway in this outfit. I called for a cab, and
soon I was sitting in the back of an overheated taxi, very aware of the sly
glances from the driver in the rear view mirror. By now, my self-confidence
was such that I knew he was looking at me as a woman, and my feelings of
vulnerability intensified.
I
tipped him handsomely when we pulled up to Gibson’s. Although it was a
bitterly cold night, Rush Street was full of life, and I caused quite a scene
when I stepped out of the cab in my skimpy little dress. The crowd outside
Gibson’s parted and a guy opened the door for me, I handed my fur to the coat
check girl, and after a quick trip to the ladies’ room to check on my hair and
makeup I was fighting for a place at the bar.
There
he was, right where I expected to find him, holding down a barstool with a Jack
Daniels in one hand and a cigarette in the other. Norman Wolf looked a bit
more disheveled than usual, and I watched with amusement as he hit on a cougar
with zero success. Meanwhile I was having problems of my own, trying as nicely
as I could to brush off lame pickup lines from two losers.
Then
the barstool next to Norman opened up, and I was on it in a flash, making an
elaborate show of tugging at the hem of my dress after I climbed onto it. I
totally ignored Norman at first, even though he was obviously staring at me.
The moment of truth: even in his inebriated state in the dim light, would he make
me as Matt McCoy? I wanted to have plenty of people around if that happened.
I
reached into my purse for one of Tracy’s cigarettes. When I started fumbling for
my lighter, Norman whipped out his, and I gave him a sideways glance while he
lit me up. “Thanks,” I said, feeling a little buzz after I drew the sweet
smoke into my lungs.
“Can
I buy you a drink?”
“Sure,
that would be nice.”
Norman snapped his fingers at the
bartender. “What will it be?” he asked me.
“A
Cosmopolitan, please.”
“A
Cosmo for the little lady, and another Jack on the rocks for me,” Norman ordered. I gave him a shy smile and waited for him to make the next move.
“Are
you from Chicago?” he asked.
“Yes.”
“I
haven’t seen you here before.”
“I
live in Rosemont. I was supposed to meet a friend for dinner tonight, but he
had a last-minute conflict, and here I was, all dressed up with no place to
go. So I decided to console myself with a drink before I went back to the
burbs.” My female voice was working for me, and the lies rolled easily off my
tongue.
“That’s
a shame,” Norman said. “Why don’t you have dinner with me?”
“I
don’t even know your name.”
“It’s
Norman….and you are?”
“Ashley.”
“Well
then, now that we’ve been properly introduced, let’s find ourselves a table.”
He pushed back his barstool and took my hand. It wasn’t easy hopping down in
my dress, and I’m sure Norman enjoyed the spectacle. He bulled his way through
the crowd without waiting for me. Grudgingly, I had to admire his
self-confidence as I tottered after him in my heels. By the time I caught up
with him, he was bribing the maitre’d for the next table, and soon we were
seated side-by-side in a cozy booth.
When
a waiter arrived with our drinks from the bar, Norman ordered two more before
he turned his attention to the wine list. I’d been out with him once before,
for lunch as a guy, and I remembered how he’d splurged on a ridiculously
expensive bottle of wine. I couldn’t wait to see how much he was going to
spend on me.
I
wasn’t disappointed. “They have an exceptional Bordeaux if you feel like red
meat tonight,” he said.
“A
filet would be nice.”
“Done.”
I crossed my legs with a swish of nylon and gazed around the restaurant while Norman dealt with the sommelier and the waiter. It seemed that half the tables were occupied
by middle-aged men with hot chicks. The waiter lit a candle on our table, but
the light was still low, and I was sure that Norman had no idea that his
chippie was really me.
I
reached into my purse for another cigarette. I waited expectantly for Norman to light it, and this time I touched his hand when he offered his lighter.
“Thanks,” I said. “Do you come here a lot?”
“I’m
one of their best customers. How do you think we got this table?”
Such
an ass, I said to myself. “You must be important,” I purred.
“And
how about you, Ashley? What do you do?”
“I’m
just a flight attendant.”
“How
nice,” he said condescendingly. “You must meet some fascinating people.”
“Oh
sure, you meet a lot of nice cattle on the cattle car.” I was beginning to
feel more at ease, and I needed to loosen him up. He took another pull at his
Jack Daniels and leaned closer to me. I felt his hand brush against my leg.
Another long draw on my cigarette while I waited for his next move.
“You’re
much too intelligent and attractive to be stuck in a job you don’t like,” he slurred.
God, you really must be drunk, I thought to myself, considering that the girl
you’re hitting on is really a guy trying to act like a total bimbo. The whole
scene would have been comical if my situation weren’t so desperate. Our wine
and salads arrived, and while we engaged in small talk, I tried to remember Tracy’s lessons on how to be ladylike.
Our
steaks were presented with a flourish on sizzling platters, and my filet was so
delicious I almost forgot who I was. Tiny bites! I had to remind myself, while
Norman attacked his 16 oz. sirloin like a Rwandan refugee. Suddenly his face
turned blue, and before I realized what was happening he started to pound on
the table, gasping and clawing at his throat. He was choking on a piece of
meat! Without thinking, I jumped up, ran around the booth and dragged him onto
the floor. Then I reached down around his massive chest and grabbed him in the
Heimlich maneuver. One sharp tug…another sharp tug…and then a piece of sirloin
shot out of his mouth and he was able to breathe.
I
sat next to him on the floor, my dress up to my thighs, panting with exertion.
Several waiters ran over to us offering to help, and one of them took my hand
and lifted me back on my feet while Norman brushed them off. “I’m fine,” he
said with embarrassment.
“Thanks
to your lady friend,” a man at the next table said, and the whole restaurant
burst into spontaneous applause. I did a little curtsey and resumed my seat.
Our table top was a shambles, and the waiters swiftly replaced our tablecloth
and salvaged what remained of our dinners. A new bottle of wine was produced
compliments of the management, and we both sat there sipping in silence. I
stole a glance at the compact in my purse to make sure my wig was still on
straight, wondering if this episode had ruined my chances for tonight.
To
the contrary, when Norman finally spoke, he sounded almost sincere. “Ashley,
you just saved my life. I am totally indebted to you. How can I ever repay
you?”
Half
an hour later, we were cruising up Lakeshore Drive in Norman’s Jaguar.
Although my scheme had been to lure him to Tracy’s apartment, when he suggested
that we adjourn to his place for a nightcap, I jumped at the chance, although I
was becoming more and more worried as we drove towards his building. If I’d
gotten him alone at Tracy’s place, I intended to knock him out with booze laced
with sleeping pills, tie him up, and force a confession out of him when he came
to.
Now
I had no plan, and in my little dress and heels I would be defenseless if he
tried to take advantage of me. As if to confirm my worst fears, Norman’s arm strayed over the console and squeezed one of my silky knees. “Thanks again
for saving my life tonight, baby,” he whispered. I fought my revulsion and
allowed his hand to slide up my dress until it got dangerously close to my
secret.
Finally
I grasped his hand and gently but firmly guided it back onto the wheel.
“Better watch your driving, you don’t want the cops to stop you after all we’ve
had to drink.”
“Yes,
dear,” he teased me. “You really are my guardian angel tonight.” Talk about
clueless, I thought to myself. Norman deliberately jumped a light just to
spook me, then he started pawing my legs again. Before I could protest, he
pulled into a driveway and parked in his reserved spot in an underground
garage. I lifted the visor and peeked at myself in the vanity mirror while he
was walking around the car to open my door. The girl looking back at me in the
mirror seemed very nervous. Then my door was open, and Norman was treated to a
spectacular leg show as I scrambled out of my bucket seat.
He
put his arm around me and guided me towards the elevators. We rode in silence
to one of the upper floors of an exclusive high-rise. Nobody saw us enter the
building, and when the elevator doors opened the hallway was deserted. I took
his arm as we walked, unnerved by the clickety-clack of my high heels echoing
down the marble corridor. His unit was at the very end, and after he unlocked
the door he held it open for me without turning on the lights.
At
first I thought that he was going to jump on me then and there, until I
realized that he wanted the full impact of the view to hit me in the darkness.
It was spectacular, a blaze of lights reflecting off the glistening shore of Lake Michigan. How many women had he used the same technique on, I wondered?
While I was standing at the floor-to-ceiling windows, he turned on some music
and soft lights. “How about a glass of champagne?” he asked, nuzzling me from
behind as he slipped off my fur.
“Okay,
after I powder my nose.” He pointed towards a hall bathroom, and I made a
beeline for it, locked the door behind me and grasped the vanity with both
hands, shaking uncontrollably. What the hell was I doing here, in women’s
clothing, with a man who had already ruined my life? I looked up at myself in
the mirror and saw a scared little girl who was in way over her head. The best
I could hope for was to make my way back to the street without humiliating
myself…then all I’d have to do was hail a cab, in a dress and heels, in
downtown Chicago in the dark of night.
Maybe
there was another way…I desperately tried to come up with a plan as I went
through the motions of straightening my dress and stockings, brushing my hair,
freshening my lipstick. The only thing I had going for me was the way I
looked: the woman in the mirror was undeniably pretty, and Norman Wolf was
already impaired from way too much alcohol. If I could keep up the façade long
enough to find a weakness, maybe I could save myself. “You’re a woman,” I told
my reflection in the mirror. “I’m a woman,” she said back to me.
Norman was waiting for me on a cream
leather sofa, two glasses of champagne bubbling on the glass coffee table. I
leaned against the wall and unstrapped my heels, gratefully feeling the relief
from walking across the plush carpet in my stocking feet. I sat down next to
him and tucked my legs under my dress. He handed me a fluted glass of
champagne, picked up his, and we clinked them together in a silent toast. “To
Ashley,” he said as an after-thought, “the woman who saved my life.”
To
Norman, the shit who wrecked mine, I thought to myself as I sipped my
champagne. I got up from the sofa and retrieved a cigarette from my purse. Norman lit it for me, and I sat down demurely in a facing chair, playing hard to get. He
drained his champagne in two gulps and topped me off before he poured himself
another glass. How much more alcohol could he take before he passed out, I
wondered?
As
if to answer my question, Norman asked me if I’d like a tour of his condo.
God, what a nightmare! I drained my glass and reluctantly got to my feet,
pretending to be a little drunk to lower his guard. When we got to his study,
I spied a heavy-duty safe behind an open closet door. An inspiration came to
me. “What’s my reward for saving your life?” I asked.
“Your
reward?”
“The
keys to your jag? Or maybe I’ll just move in here with you….”
Being
a guy, I figured that would throw him, and sure enough he responded the way I
expected. “Sweetie, I owe you big time. Let me show you how generous I can
be.” I held my breath while he dialed the combination to his safe…there was a
large brass paperweight on his desk, and I deftly picked it up and hid it
behind my back. When he bent down to reach into the safe, I came up behind him
and brought it down as hard as I could on the back of his ugly head.
Norman collapsed into a heap on the
floor. I stepped over him and started unloading the contents of his safe,
looking for anything that might incriminate him and clear me. To my
astonishment, all I found were thick envelopes stuffed with wads of cash, in
large bills…hundreds of thousands of dollars, more like millions, which Norman must have stashed away over the years.
I
looked down at him, and for the first time I realized that something was
wrong. Not only wasn’t he moving, he didn’t appear to be breathing, and his
face had turned a deadly white. A quick check of his pulse confirmed the
worst. I can honestly say that I felt no remorse, considering what he’d done
to me. Instead, I felt sick to my stomach over what would happen to me when I
was arrested for his murder. When word got out that I’d killed a man while
dressed as a woman, I’d be fair game for the boys in prison. One way or
another, my life as a man was over.
Or
maybe not. Nobody had seen us enter his apartment. I glanced at my watch. It
was well past midnight. Coolly, I looked around the study for something to
hold the cash. An attaché case on the floor caught my eye, and I went to work
stuffing it with thousands upon thousands of dollars. When it was full, I was
barely able to snap it shut, and it weighed a ton.
Okay,
now for fingerprints…I used a towel from the powder room to methodically wipe
down the paperweight, my champagne glass, and anything else I might have
touched. While I was doing this, I was already planning my escape. I returned
to Norman’s corpse and fished his keys out of his trouser pocket. After a last
look around, I strapped my heels back on, put on my fur, picked up my purse and
the briefcase full of cash, and quietly let myself out.