Office Bet
By Melanie Brown
Copyright © 2004
Pulling up to yet another traffic light along Spring Creek Parkway, I still marveled at my luck. It wasn’t quite two months since I’d
made my escape from Wink, Texas home of Roy Orbison and the Wink Sink Hole. My dad
still had a t-shirt that proclaimed “I survived the Wink Sink!” I was so glad
to be out of there!
Some of my old friends thought I was nuts to actually
get an apartment in Plano, Texas where I work. The apartment is kind of pricey, but
I’m only a couple of miles from Xantek Corp. which is a fairly new technology
company rising up on Plano’s west side. I never have to get on a freeway to get
to work and I’m minutes away from five major grocery stores and two malls.
I’m really surprised they hired me, fresh out of
college and only 22. They were impressed by some of the software I’d written
on contract jobs to make some extra money at college. Still, this was my first
real job if you don’t count the time I spent working at the gas station in Wink,
changing flats and other glamorous tasks.
I drove my car through the tree lined and somewhat
picturesque parking lot of Xantek’s gleaming steel and glass building. This
was such a contrast to the dusty, wind blown streets of Wink. I wanted to tell
everyone what a great and wonderful life I was having, how perfect everything
thing was.
Well, not quite perfect. Don’t get me wrong. I enjoy
the work and they’re making it quite a challenge. The pay is good and I’m out
of west Texas. If there was a down side to all this, it was the
fact that I was incredibly lonely. I might as well be the invisible man. At
meetings, still being the new guy, I don’t feel comfortable joining in and the
times I do try to present an idea, I’m largely ignored. All the other guys in
my department have known each other for a while and go to lunch together and
meet after work for a beer or on weekends for sports.
The women ignore me as well. They certainly don’t
invite me to go to lunch with them, and make me feel like an interloper should
I attempt to join in one of their little cliques that happen to be talking
about something I’m interested in. And they have definitely made it known that
under no circumstances are they interested in a date, even if it’s just to a
movie.
I got into the elevator for the ride to the twelfth
floor where the IT offices were. The elevator was fairly crowded, with lots of
greetings between the passengers. Again, I was the invisible man.
Leaving the elevators, I walked through the glass
doors into our department’s lobby. Jennifer, the receptionist was shuffling
some papers on her desk as I approached. She looked up and said, “Good
morning, Mr. Stephens. Ms. Rogers wanted me to tell you she had to cancel your
project meeting for this morning.”
“Did she say why?” I asked. That was really annoying
because this was the second time this week the meeting was canceled. Until we
hashed out the requirements document, there was no way I could start working on
the specs.
Jennifer shrugged and said, “I’d be willing to bet
she’d rather be in your meeting than where she has to go. Mr. Thompson called
a staff meeting. All the department heads have to attend.”
“Would you mind asking her if we could reschedule some
time this week?” Jennifer nodded and jotted down a note. I mumbled a “Thanks”
and headed for my cubical.
I walked past Ms. Rogers office. Ann, Ms. Rogers
executive assistant was shuffling papers on her desk, trying to look busy. I
started to say some pleasantries, but before I could, Ann said without looking
up, “You’re late.” Nobody I knew liked Ann much. I know I didn’t. I’d heard
rumors she was a lesbian. She certainly seemed to hate men.
* * *
I looked at my watch and it was already after
eleven-thirty. I was starting to get hungry and felt that I was at a good
stopping point, having just achieved victory over an annoying bug in the
program I was working on. I looked over the wall of my cube and saw that Lew
was still at his desk.
“Hey, Lew. Wanna go grab a bite from across the
street at Whataburger?” I asked from over the wall.
“Sorry Harry. I was going to go with some of the guys
down to Spring Creek BBQ. They’re waiting for me downstairs.” He pecked at a
couple more keys and clicked his mouse on the Save button. “Maybe tomorrow,
huh?” he said as he left his cubical.
Under my breath, I said, “Gee. Thanks for asking if I
wanted to go along.”
As I started to walk through the lobby, Jennifer
called out to me, “Hey, where are going for lunch?”
I shrugged and said, “Probably just to Whataburger. I’ll
probably just get something to go and bring it back here so I can keep working
on my program. I had a breakthrough this morning.”
Jennifer picked up her purse and said, “Chuck and the
other guys didn’t invite you along? That was rude. Well, some of the girls
and I are going over to La Madeleine. Catch ya later.”
Under my breath, I said, “Gee. Thanks for asking me
if I wanted to go along…”
* * *
The clock on the task bar on the computer screen
clicked over three fifteen. I rubbed my eyes a few seconds. This seemed like
a good time for a break.
I walked into the break room and stopped. Sheesh!
Looks like I wasn’t the only one who needed a break. The room was pretty
full. Even Ms. Rogers and Ann were there in the corner, chatting animatedly
with some of the other women. Some of the guys were at the table talking
loudly about some football game they had seen on television.
I wormed my way through the crowd to reach the fridge
and extract a Dr. Pepper. As I popped it open, I heard Candace say to Ms.
Rogers, “Can’t we loosen the dress code a little? I can’t believe the dress
code requires leather soled shoes and that we have to wear stockings, even with
pants!”
Another woman, Joyce chimed in with, “Yeah. And even
pants are frowned on here. I hate wearing pantyhose!”
Ms. Rogers shrugged and said, “Now, girls…I don’t have
a lot of discretion when it comes to applying the corporate dress code.”
I looked around the room at the women and in a lull in
the conversation, said, “Still, it looks like y’all get to wear a variety of
sorts. I mean, each day I get to pick from my blue suit, or my brown suit, or
my gray suit.. I get to go kinda wild with the tie, though.”
Candace looked around at me and frowned, “Harry, at
least you don’t have to wear heels, or pantyhose, or have to worry about how
your hair or make-up looks. Shoot, boy. You wouldn’t last a day if you had to
wear all the crap we have to!”
I don’t know why I didn’t just go back to my cubical
at that point, but instead, I said with a laugh, “So? How hard could it be? I
mean, women do it every day, so how tough could it be?”
Scowling at me, Ann said, “I can’t believe you said
that! Do you mean to say that wearing shoes that pinch your toes, underwear
that rides up your crack and stockings that make the back of your legs itch,
isn’t hard just because women do it?”
Sitting on the edge of a table, I said, “That’s
exactly my point. None of those things make you work up a sweat, or break your
back, put calluses on your hands, crush or break bones. And yet, you act like
it’s the end of the world because a little thing like a dress code makes you
wear high heels or a skirt or whatever. Shoot, with what most guys have to put
up with, your bellyaches about little things like wearing pantyhose seem pretty
childish.”
For several seconds after I finished talking, you
could have heard a pin drop. Some guy behind me whispered, “Oh, shit. Looks
like Harry really stuck his foot in his mouth now.”
Ann folded her arms and said, “Oh, really now! I’d
like to see a typical guy put up with what we have to put up with every day!
Hell, Harry, you couldn’t last a day if you had to follow our dress code!”
I laughed and said, “Oh, give me a break! There’s
nothing to it. I could do it for a month as easy as falling off a log!” I
couldn’t believe I just said something like that.
Ann sat up straighter and asked, “Is that so? Would
you care to make a little wager on that?” I heard Candace giggle.
“What kind of wager?” I asked.
“Nothing you couldn’t handle, it sounds like.” Ann
said with a grin. Ms. Rogers just sat there and watched with an amused
expression.
I looked around the room and saw everyone looking at
me and laughing in various ways. I started to feel very uncomfortable and I
could feel my face turning red and I was wishing I had kept my big mouth shut.
Ann fumbled around in her purse for a moment then
pulled out fifty dollars and placed it on the table. “I’m willing to put money
down that you couldn’t go one month coming to work dressed as a woman. I
really don’t think you could go a week, but a month is a sure bet. Anyone else
want to join in, put your money on the table. If Harry can go the distance, he
gets the pot, if not, Harry you have to match the bets and the money is divided
based on who paid what.”
I heard Lew behind me say, “He won’t do it. Hell,
he’d be crazy.”
Carl said, “You don’t have the legs for it, Harry!”
and laughed.
Candace sneered, “Put your money where your mouth is!”
The room began to spin as I started to drown in a sea
of cat-calls, laughing, and taunts. This was awful. What started as a stupid
joke was now a disaster. I knew my face was beet red. I started having
trouble breathing. I had wanted more people to pay attention to me, but not
like this!
Sensing my distress, Ms. Rogers called out above the
din, “Hey! Hey people! Settle down. Now Harry, you don’t have to accept
Ann’s rather creative bet. And if you don’t, I understand completely.
However, if you do, I don’t want this office to turn into a circus. Harry, if
you come in here Monday looking like just a guy in a dress or like some drag
queen, if productivity suffers, the bet is voided and the money wagered goes to
the Christmas party fund. If y’all can’t act professionally about this, then it
will end.”
Everyone was staring at me, waiting for me to make a
decision. If I lost and everyone plunked down fifty dollars, I could lose
quite a bit of money. Part of me just wanted to run and hide somewhere. It
was the other part that didn’t want to back down that said, “Sure. I could do
that. No problem!“
Lew slapped me on the back saying, “You’re crazy,
man! You won’t make it through the first day!” He tossed a twenty on the
table where Candace was writing down names and amounts.
Ann said with a smirk, “Hey, Harry will need a new
name. What should his new name be?”
Carl said, “Harry…Harriet?” Everybody laughed.
Lew waved as he said, “I know…Hildegard!” Everybody
roared with laughter.
“No freakin’ way!” I almost shouted.
Candace said, “We’ll have to call you something. We
can’t call you Harry. You pick, Harry.”
I thought a moment. I was too numb to do much
thinking though. After a few moments I said. “I’ve always liked the name
Heather.”
Candace wrote down another bet and said, “Heather you
shall be!”
As I started to walk away, Ann called, “Remember…full
adherence to the female dress policy! You can wait until Monday to start.”
I left the room feeling incredibly stupid. I could
still hear people laughing as sat down in my cubical.
* * *
I put in an extra hour that afternoon to get to a
better stopping place the program I was working on. And, to give the office a
chance to clear out before I left. As I walked past Ms. Rogers office, I heard
the office door open and saw a head poking through.
“Oh, good. I caught you before you left. I was
afraid you’d already gone.” said Ms. Rogers. “I wanted to talk to you before
you left.”
Stopping in my tracks and turning to face her, I said,
“Sure, Ms. Rogers. I have a feeling I know what you want to talk about.”
She sat down on the edge of a handy desk and smoothed
her skirt. “Yes, I want to talk about the little bet this afternoon.”
“I know. I was just trying to make a joke. Things sure
got carried away. And fast.” I said as I walked up to Ms. Rogers.
Arms loosely folded and looking directly at me, Ms.
Rogers said, “You know, Harry, you don’t have to do this. If you want out,
just say so. I’ll tell everyone that the bet violates some company policy and
everyone will get their money back.”
“Thanks.” I said. “But I think I’m going to stick it
out. It’s not about the money. I just want to show them I can do it. What
surprises me is why you’re allowing this in the first place.”
Ms. Rogers laughed. “Everyone has been pretty
stressed out over the current work-load and there’s no end in sight. It seemed
like a harmless way for everyone let off some steam. And, who knows, maybe
there will be some lessons learned.”
I shifted my feet and said, “Does that mean you think
I’m wrong?”
Ms. Rogers smiled and said cryptically, “I didn’t say
who was going to learn the lesson.” She chuckled, then added, “Just be glad
the restrooms in this building are unisex!”
* * *
It was finally Friday as I climbed into my car, the
interior superheated by the afternoon sun. The last couple of days had been
pure hell. I was already the butt of many jokes around the office and the bet
hadn’t even started yet!
As I drove out of the parking lot, I decided I’d
better start getting ready for Monday. Instead of heading home, I turned down Preston to head
towards the mall in Frisco. There were quite a few clothes stores there, so
hopefully I would find something suitable to wear.
After arriving at the mall, I walked around it a
couple of times, worrying myself sick at the prospect of actually buying
women’s clothes. Clothes for me! What had I gotten myself into. I fingered
my cell phone, toying with the idea of calling Ms. Rogers and telling her I’d
like to back out of the deal. But then I immediately dismissed the idea. I
squared my shoulders and walked into large department store and headed for the
women’s clothing section.
No sooner had I walked into the middle of the women’s
section than I started to panic. I had no idea what I was looking for. I
didn’t know sizes or styles or much of anything. A sales girl must have
noticed my distress and walked up to me.
“Good afternoon, sir!” she said brightly. “How can I
help you?”
At first, I was going to lie about my true mission
here and say something about that I was looking for something for my wife,
girlfriend, or whatever. But then on second thought, I decided, what the
hell? Why not just try being honest? What was she going to do, throw me out?
I laughed a little nervous laugh and said, “I really
hope you can help me out. This sounds stupid…” I saw her expression changed
slightly towards the ‘oh, God, now what?’ expression. I continued, “…but I
made this crazy bet at the office. I need to dress like a woman for the next
week or so or I lose the bet.”
She smiled and said without skipping a beat, “Well,
sir, I’m sure we can help you find just the right outfits. Is your office
casual or professional attire?”
I thought I could see the dollar signs rolling in her
head from her potential commission. I said, “Oh, very professional. Quite
strict, actually.”
With a small gesture, the sales girl said, “Let’s see
what we can find for you. Come this way?”
She led me over to where there were racks and racks of
skirts and dresses. First she took a tape measure and made some quick
measurements of me. Then she pulled a few outfits off the racks and asked me
what I thought of them. I said I liked the dark blue one.
“Why don’t you go back there and try it on?”
“Here? L…like right now? I can’t do that!” I
exclaimed as I felt my cheeks start to turn red again.
She handed me the outfit and said, “Go ahead. Try it
on. It’s OK. I get men in here all the time to try on dresses.” I couldn’t
tell if she was kidding or not.
I went back to one of the little dressing rooms and
closed the door. The door didn’t go all the way to the bottom, so it would be
obvious that the room was occupied by a man. I quickly stripped down and
picked up the soft, white blouse. I started shaking as I contemplated actually
putting this stuff on. I gritted my teeth and slipped on the blouse. At
first, I couldn’t figure out why I couldn’t button it, then realized the
buttons were on the wrong side. Why the hell did they do that?
Next I slid on the skirt and tucked in the blouse. I
couldn’t get it to button together until I realized I was trying to wear the
waist at my normal place. I pulled it up higher and it fit almost perfect.
The sales girl knew her stuff.
I put on the jacket. The sleeves seemed a little
short, but otherwise a good fit. I looked at myself in the mirror and was
absolutely mortified. I looked like a complete dork standing there. This was
never going to work.
“Come out and let’s take a look.” called the sales
girl. “There’s no one out here. It’s OK.”
You’ve got to be kidding me, I thought. I’m not going
out there looking like this. I said, “No. I don’t think so.”
“Please sir. I need to see if the clothes fit you
OK. If you’re going to be dressing this way for a week or more, you’re going
to need more than one suit.”
Hesitantly, I slowly opened the door and stepped out.
I could tell she wanted to laugh. She controlled
herself though and said, “That’s a good fit. With the right wig, some make-up,
shoes and hose, I think you’ll do fine. Go change back and let’s select some
more outfits.”
Finally, we’d managed to pick around four different
outfits that could be mixed and matched to give me almost two weeks worth of
feminine attire. We then spent (what I felt) an inordinate amount of time
selecting underwear – bras, panties, slips, pantyhose, camisoles – then on to
several pairs of shoes to match the outfits. I was getting dizzy and a
headache.
As I was piling all this stuff on the counter and
wondering just how in hell I was going to get this out to my car, the sales
girl said, “I think you’ll be very happy with these clothes.” As she started
totaling up the purchases, she continued, “I would have taken you over to our
complete make-up counter, but I think you’re going to need the help of a
professional who is used to handling clients such as…um…er…yourself.” She
handed me a card and explained, “You need to give her a call as soon as you can
to see if she can get to you tomorrow. She normally just does make-overs, but
she’ll also do consulting and, well, training for crossdressers, drag queens,
and you know, people like you.”
As I took the card, I said, “Well, you know, I’m not a
crossdresser or a drag queen, transvestite, whatever. I’m just an idiot who
accepted a stupid bet.”
She finished ringing up the total as she said, “Yeaaahhh…”
She took my check and said, “Have fun. I know I always feel great after buying
some new outfits. Have a great week next week!” She slammed the cash register
closed and gave me that ‘I’m done with you now so leave’ smile.
I took a quick look at the card before I began
grappling with my new wardrobe. The card read “Thelma’s Glamour Emporium.” I
decided to give Thelma a call when I got back to my car. I put the card in my
pocket, and grabbed my load and then tried to remember which direction I needed
to go to find my car.
* * *
It was two
o’clock Saturday afternoon as I wheeled
my car into the parking lot of Thelma’s Glamour Emporium. I had tried on most
of my new clothes earlier in the day. The clothes all fit, but I just looked
like a geek in drag.
Thelma’s was a small unit in a small shopping center.
I was mortified to see at the bottom of her sign the words, “Crossdressers
Welcome”. I really didn’t want to walk in there. But, if I wanted to pull
this off, I was going to need some really major help.
As requested, I brought an outfit in a small suitcase
which included a navy blue skirt and jacket, light blue blouse, slip, panties,
bra, pantyhose and black pumps with three inch heels. I’d tried the heels on
this morning and almost fell through the sliding glass door at the rear of my
apartment.
Also as requested, I’d shaved real close before coming
over. I was also requested to shave my armpits and legs if I wanted the full
effect. I’d bought a women’s razor for the occasion. I hadn’t really even
gotten started and ‘being a woman’ was already being a lot more trouble than I
would have thought.
Finally, I took a deep breath, stepped out of my car
and boldly walked through the door. I’m not sure why, but I expected to see
leather outfits, chains and bullwhips hanging on the walls. What I did see
though, was a brightly lit, clean little shop, looking pretty much the way I’d
expect a regular beauty shop would look like. I was alone in the front room.
As the door shut behind me, a voice from a back room
called out, “Just a minute!” and a moment later, a middle-aged, but still
attractive woman emerged from a hallway. “Good afternoon“, she said
pleasantly. “I’m Thelma. You must be Mr. Stephens. Please, sit down and tell
me again exactly what it is you need.”
I rotated the chair around so that the back was to the
mirrored wall and counter with a dizzying array of cosmetics and assorted tools
and devices. I set the suitcase on the floor as I sat down I the chair. I
cleared my throat and said, “Excuse me, I’m a little nervous.”
Thelma nodded with understanding and said, “That’s
quite alright. Would you like some coffee? A soda?”
I shook my head and said, “No thanks, I’m fine. I…I
guess the reason I’m here is because I…well…I…” my voice trailed away and I
felt my cheeks burning hot. Thelma just stood there, leaning patiently against
a wall. Finally I managed to say, “I would like for you to show me how to put
on make-up properly. And hopefully, maybe you can show me a few things about
how to walk, and carry myself as a…a…w…woman would.”
Thelma looked me up and down and nodded as she stood
up straight and began walking over to the door. As she picked up a sign that
read ‘Private Session’, she said, “I don’t think that’s going to be much of a
problem.” She paused as she put up the sign I the store front window. Then
she added, “Now, go in that little room over there and change into your panties
and bra and we’ll get started.”
Nervously, I got up from the chair, picked up my
suitcase and walked into the changing room. I removed the suit and hung it on
the convenient hook and ran my hand down it to try to smooth it back out. Then
I quickly stripped down and slipped into the smooth nylon briefs. They were
just plain, white nylon panties, but I have to admit they felt very exotic.
The bra was just uncomfortable. I don’t know how you’re supposed to put it on,
but I hooked it from the front and then rotated it until the hooks where in the
back.
Looking at myself in the full length mirror, I said to
myself, “This is never going to work.” I opened the door and walked back to
the chair. Thelma motioned for me to sit.
“Is this your first time to dress?” Thelma asked.
“Most of the guys who come here either want a glamour make-over for a photo
shoot or a special date. Sometimes they want make-up tips.”
“Yes.” I said. “Until this weekend, I’d never even
thought about putting on any articles of women’s clothing.”
Thelma started examining my face as she said, “That’s
odd. Most guys figure out they like women’s clothes either in their early
teens or even earlier.”
Sheepishly, I said, “Oh, I’m doing this because of a
really stupid office bet.” Thelma stopped what she was doing and looked at me
funny. I continued, “That’s why I need to know how to put on make-up and
stuff. I need to dress like a woman for at least a month.”
“What kind of bet was it that you lost?” Thelma asked.
“Oh, I didn’t lose it. At least not yet. The bet is
to see if I can stand to do what women have to do at work for a month.” I said.
I then explained the bet further.
When I had finished telling her about the bet, Thelma
said, with a tinge of anger in her voice, “I should toss you out on your ass
right now, you little chauvinist jerk. You think doing things as a woman is
easy, eh? You’ve got quite a surprise coming.”
“Hey, I didn’t say I really believed that. I was just
trying to stir up the conversation!” OK, so I did believe it, but just from
what I’d had to do so far, I was beginning to feel I was wrong about it being
easy.
Frowning, Thelma said, “Well, you might actually learn
something out of this. From the looks of things, I’d say you’ve probably
already spent more than you’ll make on your bet.”
Nodding in agreement, I said, “I think you’re probably
right.”
Thelma suddenly took on a professional demeanor and
said, “Well, let’s get this show on the road. Sit back down.”
As I sat down, Thelma busied herself arranging an
array of brushes and cosmetics. As she turned to face me, she was holding a
small jar of make-up. She said, “Now, I’m not going to do a glamour make-over
or anything like that. I’m going to instruct you on how to wear make-up the
way most women do for a day at the office. First, I’ll just make you up so you
can see how it feels and we can get an idea of what you’re going to look like
and find your problem areas.”
As she put a daub of make-up on her finger she said,
“Most of the guys who come to me have been wearing make-up for years and love
being pampered during a make-over. The few guys I get, like you, who have
never worn make-up before usually don’t like the way it feels at first, or the
way it smells, and so on.” She then streaked the daub along my cheek and
started smoothing it in.
She was right. I flinched at the first touch as it
was cold and I didn’t like the smell. I didn’t like the way lipstick felt
going on, or it’s smell either, nor did I much care for when she applied the
mascara. I thought, my God, how the hell was I going to be able to do this
every day for a month? I hadn’t had make-up on for five minutes before I
wanted to wash it all off.
After using several brushes on my face, Thelma backed
away and looked at me. She went over to a shelf with a wide variety of wigs,
picked a couple with shoulder length hair. She said, “Hmmm. Now we did this
rather quickly, but still, I think we got fairly good results.” She then
picked up one of the wigs she’d selected, and placed it on my head and did a
quick brushing. “Now, don’t look I the mirror yet and go put on the rest of the
outfit you brought, then go take a look at yourself in the full length mirror.
Be sure to put your heels on too.”
I wanted very much to look at the mirror, but I did
what she asked and went back to the little room to put on the blouse and skirt.
It bothered me that the wig hairs tickled my neck and shoulders. I didn’t
bother with the pantyhose for now.
I hobbled over to the mirror again. At first I was
afraid to look, expecting a complete monstrosity to stare back at me. What I saw,
surprised me. Staring back at me was a fairly attractive woman. Thelma
appeared in the mirror next to me and said, “Pretty amazing, huh?” I nodded and
she continued, “Make-up is a wonderful thing. Go sit back down and we’ll clean
you up and we’ll start the make-up lesson.”
I just stood there for a moment in complete
disbelieve. I was certainly no Miss America, but I thought I looked just as
good as most of the women in the office. I thought I looked better than Ann at
least, and I really hoped she would be very pissed off about that.
For the rest of the afternoon, Thelma went over the
finer points of putting on makeup, showed me how to use something called a
‘gaff’ to hide my privates, care and feeding of my wig, and proper female
mannerisms. Pretending to be a woman was going to be tougher than I thought.
When I left to return to my apartment, I was wearing
the suit, hose, heels, make-up, wig and all. Climbing into the car, meant
sitting down carefully, then swinging my legs inside. The heels put my feet at
an awkward angle to the pedals.
I looked at myself in the rearview mirror. I couldn’t
believe what I was seeing. I studied my hands with the polished nails for a few
moments. I thought that maybe, just maybe, I was going to pull this off after
all. One part of me was dreading Monday morning. The other part was oddly
excited.
Most of the drive home was uneventful, not counting
when my foot slipped off the brake pedal and landed on the accelerator sending
me blasting through a red light. That’s all I needed now was to get stopped by
a cop or be in wreck.
I spent the rest of the evening and most of Sunday,
practicing walking in heels, and trying on all my outfits and playing with my
make-up. I was beginning to think Monday was going to be a walk in the park.
* * *
End of part 1
since 10/26/04