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Date: Thu, 25 Dec 1997 13:16:20 EST
From: Laura2day <Laura2day@aol.com>
Subject: The Bet
I can pinpoint the day this all started. It was a chilly, Sunday
afternoon in early December. A light rain was falling outside and Carol
(my wife) and I had built a cozy fire in the fireplace. She was sitting on
one of the couch, her legs curled up beneath her reading and sipping a
glass of wine and I was sitting at the other watching the Giants begin to
give away a 21 point lead to the Eagles.
Carol stood up and stretched, heading toward the kitchen.
"Get me a beer, hon'" I called after her.
"What's the magic word?," she asked with a twinkle.
I just wasn't in the mood for this. I'd had a bad week at work,
the weather was making me miserable and the Giants weren't helping. "Just
get the beer, alright? I don't feel like playing games."
She brought the beer and gave it to me without saying a word. When
I opened it, it exploded all over me. "What the big idea?"
She giggled to herself, "You really should have asked me more
politely. I'm not your maid, you know, I'm your wife."
"Yeah, well right about now I think I'd rather have a maid. At
least a maid wouldn't go shaking up my beer."
She turned to me. "You're serious, aren't you?"
I didn't replay, but just stared at the tube.
"Look at me when I'm talking to you." I dismissed her pique with a
wave.
"OK, have it your way. I have a wager for you. Interested?"
I was, and turned around to face her. "Go ahead. What are you
suggesting?"
"You want a maid so much, here's your chance. If the Giants win
today, next week I'll be your maid for the game. I'll get a sexy little
maid's outfit and I'll serve your every need all through the game, and who
knows, maybe after. How's that sound?"
It sounded great. Carol is a beautiful woman and the thought of
her in a tight, short maid's outfit was something I'd fantasized about
many, many times. On the other hand, it sounded a little bit too good to
be true.
"And if they lose?"
"Nothing too drastic. Instead of me reading and you watching the
game, we'll rent a long, romantic movie and watch it together while we talk
like a couple of long, lost girlfriends." Her eyes twinkled.
That didn't sound too bad. The Giants were playing the Lions next
week and that didn't exactly come off as the game of the century. "That's
it?" I asked.
"That's it. You just have to dress the part."
"Dress the part?"
"Yes, dear, are you having trouble hearing?," she asked. "My
girlfriends don't wear jeans and flannel shirts when visiting." She smiled
a great, big smile.
"You want me to wear a dress?"
"A dress, or a nice skirt, or whatever you please. Just no pants."
I thought about this for a minute. The Giants were leading by 21
late in the third quarter. The upside was having an amazing fantasy come
true. The downside seemed a little silly, but how bad could it be? If
this was a bad bet, I couldn't see it.
"Honey, you got yourself a bet."
Carol leaned over and pecked me on the cheek. "That's nice dear,"
she smiled. "Let me know how the game comes out." With that, she got up
off the couch and headed for the kitchen to begin dinner.
I returned to the game and was a little surprised to see that the
Giants lead was down to 14 points during the commercial break between the
third and fourth quarters. About four minutes into the quarter, the Eagles
returned an interception 63 yards for a touchdown to bring the score to
28-21. On the kickoff, the Giants fumbled and the Eagles recovered. Two
plays later it was tied at 28. After the two teams traded unsuccessful
drives, the Eagles drove the ball to the Giants 20 where they scored a
field goal with less than two minutes left to give them a 31-28 lead. The
Giants did nothing in the remaining 90 seconds, giving the Eagles the win.
I sat there stunned. Carol won. No maid. No football next week.
And I had to wear a dress. When the news came on after the game, Carol
poked her head in the living room. "How did the game end, honey?"
"The Eagles won."
"That's wonderful, honey, we're going to have such fun next week."
She was grinning from ear to ear.
"You're serious, aren't you?"
"Absolutely, dear, absolutely. You would have been if you won."
"I guess. Where am I going to get a dress?"
"You know, sweetie, I think that's your problem." I could swear
she was smirking as she returned to the kitchen.
I couldn't imagine how I was going to get a dress and thought about
little else for the next couple of days. I finally got up my nerve to go
to the shopping mall on Wednesday evening, but when I saw one of the
neighbors in the atrium I got scared and left. When I got home, Carol
noticed that I was a little late. "Doing some shopping dear?," she asked
innocently.
I said nothing and ate my dinner in silence.
A couple of times during the week Carol mentioned how much she was
looking forward to this Sunday and asked what movie I wanted to see. I
just grumped about and refused to get pulled in, and I think that made her
even happier.
It was on Saturday that I finally got up the nerve to get my dress,
because by then I thought up a plan. I drove out to the mega-discount
store a couple of towns over, where no one was likely to recognize me.
Once there, I got a shopping cart and picked up some duct tape, some
athletic socks, a couple of big bags of potato chips, some windshield
washer fluid and one of those big ugly flowery housedresses that zip up the
front, the kind my grandmother used to wear all the time. I could play
this thing for laughs, couldn't I?
I had to push that damn cart around the store a half-dozen times
before I found them, but I did. I picked out the biggest one I could find
after I realized I had no idea about sizes, so I got the biggest they had,
which was a 28 and quickly jammed it into the cart. When I got to the
checkout, the girl rang up the housedress just like everything else, no
bells and alarms went off, and she bagged my purchases and I drove home.
On game day, I got dressed as usual, had breakfast, ran a couple of
errands and generally puttered around the house. Carol did the same thing,
but there was a real bounce in her steps, where I was dragging. She kept
looking at me and smiling and it was getting on my nerves.
About ten minutes before kickoff, she asked "Aren't you forgetting
something, dear?"
I grumbled and shuffled off to the bedroom where I got the
housedress out of my closet. I stripped off the jeans and flannel shirt
and put this monstrosity on over my T-shirt and boxers. Zipped that sucker
up and then put on a pair of white sweat socks. I glanced in the mirror
and from chest level down, I could have been my grandmother.
"Ta Da!" I shouted as leapt into the living room.
Carol just stared at me. "You're kidding."
"Uh, no. You wanted me in a dress. I'm in a dress."
"You missed the whole point," she said quietly. "I wanted a quiet,
intimate, warm, lovely, romantic day and you turned this into a joke. A
stupid pointless idiotic joke."
Now it was my turn to stare. "But..."
"I thought the clothes thing might be a little fun. Might shake you
up a bit and suggest some stuff for later, but...I can't believe you did
this. You are such a selfish prick. Take that ridiculous thing off."
I did as she asked. I really didn't know what to say to do, so I
just stood there while Carol stared at the fireplace. She abruptly got up
and stalked off. About ten minutes later I heard her start the car and
drive off. I got dressed again and turned on the game, but my heart wasn't
in it. When she came back an hour later, she glanced at me on the couch,
beer in hand, Giants on the tube, snorted and walked straight upstairs.
For the rest of the day we didn't speak and sleeping next to her
was like sleeping next to an igloo. Our conversation for the next couple
of days consisted of "Pass the salt," "Have you seen the paper?" and "Can't
you even pick up after yourself?" accompanied by a pair of dirty socks
hurled in my direction.
I was in trouble. *******************
I was in trouble and the only thing I could think of to get me out
of it was to turn the clock back a week. Some things were easy. I picked
up Dr. Zhivago at Blockbusters, some cheese and crackers at the
supermarket, a nice Chardonnay and an expensive champagne at the liquor
store and a bundle of wood at the hardware.
Now came the hard part. ***************
I thought that getting the dress would be the right place to start,
but I came up against that size thing again. I couldn't just walk into a
store and grab something because I had no idea what size a thing to grab.
I was going to have to have a salesgirl help me and I just couldn't imagine
how I was going to walk into a store and say, "I need a dress - can you
tell me what size?"
After thinking about it for a day or so, I decided to tell the
truth. I could walk in, look bashful and tell the truth. Then maybe the
salesgirl wouldn't think I was a pervert and might actually help me. What
did I have to lose except my self-respect?
I traveled to a mall about 20 miles away so that I could be a
little surer that no one would recognize me. I thought that it might be
easier at one of the big department stores than a smaller store, so I went
in to the Macy's and headed for the dress department.
It was about 7pm on a Thursday night and not very crowded but I was
a little intimidated as I walked through the women behind the cosmetic
counters and past the women browsing through the shoes (I was going to have
to get shoes, too!) and the hosiery. I didn't know how I was going to do
this, but I knew I had to.
When I came to the dress department walked around it a couple of
times and then walked in timidly, looking utterly clueless. A very pretty,
very young blonde came up to me and smiled. "Can I help you sir?," she
asked.
It was now or never. I cleared my throat. "Yes. I guess so." I
looked at her and then looked down. "My wife and I had a bet on last
week's Giants game and I lost. Now I have to watch this week's game in
drag."
The salesgirl giggled and blushed, but she wasn't blushing nearly
as deep as I was.
"I don't have a clue about sizes or anything, so I need all the
help I can get." I smiled bashfully.
"OK," she said and giggled again. She pawed through a couple of
racks and then looked at me and said, "I'm going to have to get my
supervisor, sir. I've never fitted a man before. Do you mind.?"
I blushed and nodded no and tried to make myself as inconspicuous
as I could. In a couple of moments, the girl came back with a woman in her
mid-40's with a brittle blonde hairdo and a brass nameplate that said
Mrs. Kelleher. Mrs. Kelleher smiled at me and simply said, "Yes?"
I told her about the bet and my predicament. She never stopped
smiling. "I'm afraid we can't help you, sir." She emphasized the sir.
"You need to go the women's department."
I looked confused. "Isn't this the women's department?"
"No sir," she explained, as if talking to a kindergartener. "This
is the misses' dress department. The women's department is on the second
floor. Or you might try one of the other stores in the mall that caters to
larger sizes." She smiled again and walked away. I could hear the girl
giggle again from behind a rack of cocktail dresses.
I was unbelievably embarrassed at this point. I slinked out of the
store, past the cosmetics ladies and back into the mall. I wandered around
the mall a couple of times with my eyes averted until I stopped in front of
a store called Laura Brown's - A Shop for Women. A smaller sign in the
entry way said clothes for real women in sizes for real women. I hesitated
in the door way and then walked in, again trying my best to avoid eye
contact with everyone.
After a minute or two, an attractive women in trim tan slacks,
white blouse and navy jacket smiled warmly and asked if she could help me.
Here we go again, I thought.
"Umm, yes. I know this sounds ridiculous, but I lost a bet to my
wife on last week's game and I have to watch this week's game with her in
drag." I blushed furiously and looked away.
"Oh my," she said, "you do you a problem. But who knows, you may
come to like it."
I just stared at her. I swear her eyes twinkled.
"Do you know what size you are hon'?," she asked gently.
"Umm no. I'll need your help on that."
"That's no problem at all. I'm sure I can help." Did you have any
idea of what you wanted?"
Oh my god. My brain just went completely blank My expression must
have done the same.
"Well don't worry about it, I'm sure we can pull something
together."
She pulled a tape measure out of her jacket pocket and told me to
lift my arms. I glanced around and saw that nobody else was in the store,
then lifted my arms. She measured me around the chest, then around my
waist, then around my hips.
"OK, that's done. Now, do you have any idea of what you want? A
dress, suit, skirt and blouse, or pantsuit? Sexy or simple? Color,
style?"
Oh my god. I hadn't even though about that. Here I was in a store
full of dresses and skirts and things and I didn't have any idea. I just
thought of a dress in the abstract. Now I had to pick one out. I almost
fainted. "Ummm, no. I dress I guess. Something simple."
"Actually, hon, I'd recommend against a dress for you. The way
that most of them fit, to get something nice that fits you here," she
explained as she touched my shoulders, "it would be far too blousy for your
here" and she moved her hands down to my waist. "I think you might be
better off with a skirt and maybe a nice blouse or sweater. Does that
sound OK to you?"
I nodded.
"Alright then. And I think you probably would like something
comfortable, not too revealing and probably more smart than sexy. Am I
right?"
Again I nodded.
She leaned in to whisper to me. "You know, hon, you ought to
relax. Wearing a skirt isn't going to kill you and if you're going to go
through with this, you might as well try and have some fun doing it."
For some reason, that really loosened me up. I actually smiled
back at her. "I guess. You might be right."
"Are you going to shave?"
The question took me by surprise and I reached up to my cheek.
"No dear, your legs. If you're going to shave your legs, you could
wear pantyhose and that gives us more to choose from. If you're not,
you'll have to wear tights and while that's OK, some outfits just won't
look right if you're in tights."
Again, I blanched. "I hadn't even thought about that," I blurted.
"OK, that's not a problem. We'll assume you'll wear tights so you
can make up your mind later." She spun around and walked over to the other
side of the store, looking around her as she went. I followed slowly,
watching her every move. When she turned around again to face me, she held
up an outfit and asked brightly, "Well, what do you think?"
The skirt was long and looked soft. It was mostly a dark brown,
with a border near the hem that was sort of a paisley with swirls of gold,
maroon and dark green. Above it, she held a light tan mock turtleneck
sweater. "That looks great," I said, relieved that this process was coming
close to an end. I reached for my wallet and headed towards the cash
register.
"I think you're going to have to try it on." I just stared at her.
"I can only guess at your size, you know. We're not going to know if they
fit until you try them." She held them out towards me and nodded to the
dressing room. "Give me a shout if you need anything. I'm Catherine."
The dressing room was just a few feet away but it wasn't until I
closed the door that I noticed the door not only didn't go to the ceiling,
it didn't go to the floor. I wondered if anyone was going to notice my
heavy socks and hairy legs under the door. I took off my shoes, jeans and
shirt and let them drop on the floor. I stepped into the skirt, but it
wouldn't slide up past my butt. Then I noticed a zipper and after undoing
it, I had no problems. I pulled on the sweater and everything seemed OK.
I looked like hell in the mirror, but what did I expect?
"How are you doing in there hon?" I heard Catherine ask.
"Umm. OK, I guess. It'll work."
"Come out and let me see," she replied.
"That's OK. I'm alright.:
"Don't be silly." She opened the door to the dressing room and
looked at me critically. I was absolutely mortified, standing there in a
skirt with the door wide open for anyone to see (and by now there were
about a half-dozen customers scattered about the store in additional to
another couple of saleswomen).
"Well the first thing is that we ladies usually wear our zippers in
the back." With that, she grabbed the waist of my skirt and yanked it
around until the zipper was indeed, in the back. That a couple of her
yanks included my boxer shorts thus inducing a shocking rearrangement of
things I thought was better left unsaid.
"That's much better," she said. Although I think this skirt is a
bit big. It might look better one size smaller. What do you think?" She
didn't wait for me to answer, but left to go to the rack for another skirt,
leaving the door open. I closed it as quickly as I could but she was back
in an instant to open it back up again.
"Here, try this one. Remember, zipper in the back."
I closed the door, unzipped and dropped my skirt to the ground and
put the new one on. Zipping up the back was a bit of a contortion, but I
managed.
"All set?" Catherine asked. She opened the door just as I was
finished pulling up the zipper. "Yes, that's much better."
Then she spun me around and unzipped my skirt. "I think that this
would look nicer if you tucked in the sweater," she explained as she
smoothed the bottom of the sweater down around my boxers before zipping me
up again. "Turn around."
I did as ordered. "Hmmmm. Wait right here." I wondered where she
expected me to go, dressed like that.
She came back with a belt and a scarf. The belt was wide with a
big brass buckle and the scarf was dark brown with a pattern that was
similar to the one on my skirt. She wrapped the belt around me and
fastened it in front, then spun the scarf a couple of time around itself
and draped it around my neck and over my left shoulder.
"There! You're perfect." I turned around to look at the mirror in
the dressing room and I have to admit it wasn't all that bad. The sweater
and skirt felt soft next to my body and I liked the way everything sort of
flowed gently. At least from the calves to the neck. The legs and head
certainly gave the lie to the prettiness of the ensemble and if you looked
closely you'd notice that the sweater hung in a straight cylinder when it
would have preferred nice breasts and a waist.
I shook myself out of my reverie in time to see Catherine grinning
at me. "See, now that isn't so bad is it?"
I smiled shyly back at her. "I guess these will do."
"Not yet," she said. "You'll need some tights, shoes and
underwear, maybe some jewelry, if you want to do this right. I'll get your
tights while you get dressed." She began to walk away, but turned around.
"Unless you want to wear those home?" Again, she smiled broadly as she
walked to the hosiery racks.
I just scuttled back into the dressing room to get back into my
clothes.
When I brought everything to the counter, Catherine gave me a slim
box. "Here are your tights, hon. They're chocolate brown, so they will
complement your skirt perfectly."
"Thanks," I mumbled.
"I'd love to see you when you get everything together. I think
you'd be a doll," she said as she rang up the sale. The bill came to more
than I expected (this wasn't going to be cheap!) and I gave her my credit
card. As she was processing the credit card, she said "There's a store
about five doors down called Under It All where you can pick up your
underwear. I don't think the department stores will have what you need in
your size. And there's about a half-dozen shoe stores and I'm sure you'll
find something nice at one of them."
She bagged up my outfit. "Here's a credit card application in case
you want to open up an account and a 15% off coupon for your next
purchase."
My "next" purchase? "Ummm, thanks. You've been very helpful."
"Why thank you! Now you have a nice day, and hon - relax. You're
not the first man I've seen in here and you won't be the last." She smiled
very graciously at me and I left, not knowing if I was supposed to be
relieved or embarrassed.
I turned in the direction of Under It All and walked slowly in the
direction, stopping before I reached the door. There were a pair of
mannequins, one dressed in a very sexy burgundy bra and panty set and one
in a teddy made out of the same burgundy material with some black lace
accents. Through the glass I could racks of nightgowns, bras, panties,
teddies, slips and god knows what else. The store wasn't empty, either.
There was a woman shopping with her teenage daughter, a couple of women in
business suits, an older woman by herself and a young mother with a toddler
in hand. I also saw a tall, trim, middle-aged woman in a flowery dress who
looked to be running the place and a couple of girls in their 20s who were
probably the shop assistants.
As I was standing outside the door, losing my nerve, the woman in
the flowery dress poked her head outside the shop, glanced at the shopping
bag from Laura Brown's that dangled from my hand and said "You must be the
gentleman that Catherine just called about. Come in, come in."
I followed her as she walked to the counter at the back. The store
was tightly packed and everywhere I went I plowed through wisps of
softness. I felt like the proverbial bull in a China closet. A couple of
the customers glanced at me but I couldn't tell what they were thinking.
"Now then, how can I help you?"
I told her about the bet and that I'd already purchased a skirt and
sweater and that I needed some underwear.
"Do you know what you're looking for, sir?"
I just shook my head. "Not really, no. I guess I'll need a bra
and a pair of underwear." I just couldn't bring myself to say the word
panties.
"Well that's still alright. You probably don't know your size,
right?" I think she considered my blushing nod a sign of agreement. "I
didn't think so. Take off your jacket and raise your arms."
I did as I was told and she took a tape measure and measured around
my chest. I was glad my back was toward the store because I couldn't
imagine what anyone who saw this may have been thinking. "Looks like a
40," she said to herself. Then she raised the tape measure up a couple of
inches up and measured again, only this time she just wrinkled her nose and
grunted softly.
"Were you planning on having breasts, sir?" she asked.
"I suppose I should."
"Do you have any preferences - small, large?" Although she was
trying desperately to keep a straight face, I could see the traces of a
smile dancing at the edges of her lips. How could I possibly answer a
question like that? I felt like every time I took a breath I was falling
deeper and deeper into a hole.
"I don't really know. I hadn't thought about it. I guess I'll go
along with whatever you think is best."
"I thought you were going to say something like that," she said,
almost to herself. The hint of a smile was working it's way open now, too.
"I need to measure you again," she said as she drew the tape
measure around my hips and then again around my waist. "You're a 7 or an 8
in panties." She turned around to one of the shop assistants. "Linda,
could you see if we have either "Lace Fantasies" or "Pretty All Day" in a
white soft-cup, 40B and 40C and matching panties in 7 and 8 for this
gentleman." She turned to me and excused herself. "I'll be back with you
in a moment, after I help these ladies." I saw the woman with her teenage
daughter doing their best to stare at me without appearing to even look at
me. I looked around for a hole I could drop into.
After a couple of minutes, Linda tapped me on the shoulder and
spilled an armload of white lace on the counter, arranging it for me. "I
couldn't find a 40B in the styles Andrea asked me for, but I picked a few
other things out. These are really pretty," she said as she arranged one
of the bras over one of the panties. She was right, they were. The
panties had a delicate stretch lace V pattern in the front that was
repeated around the legs. The bra had a matching pattern on the top half
of the cups and I deliciously imagined Carol in an outfit like this. Linda
smiled sweetly and said, "I'm sure whoever you're giving these too is going
to love them and..."
At that point Andrea returned, picked up the panties and held them
in front of my pants to gauge the size. I could see Linda blush a bit and
stifle a giggle. "Hmm I still can't tell." She picked up the other pair
of the same style in a different style and held those up as well, then
shook her head. "Well, anyway, you'll need to try this on to check the
size." She handed me the bra and started to steer me to the dressing room.
Well this was going just a bit too far, I thought. It was bad
enough that I was going to wear a bra with my wife in the privacy of my own
home but in a store, in a mall? No way. I started to object, but Andrea
would have none of it. "Don't be silly, the dressing room is private. Use
that one on the right," she said as she pushed me towards it with the bra
in my hand.
I closed the door behind me and took off my shirt and undershirt.
I slipped my arms through the straps as I'd seen Carol do a thousand time
but I was darned if I could reach behind me to hook it up. As I struggled,
I heard Andrea explain to Linda what was going on.
"That's so cute!" I heard Linda squeal. "So, he's already got,
like, a skirt and stuff?" I didn't hear Andrea's reply but Linda must have
approved. "Oh wow, that's so neat!"
I decided to cheat. I took the bra off, then turned it around so
the hooks were in front of me. I hooked it up, then twisted it back the
right way and started to try to get my arms inside the straps again.
"Y'know, though, Andrea, if he's going to wear tights (how did she
know that - did the saleslady from Laura Brown's tell them what I bought?)
these, like, pretty panties are going to be wasted. And since he's a guy,
he doesn't have, like hips or a waist, right? Maybe he'd be better off
with these?"
I wish I knew what Linda was showing her, but I was having a devil
of a time on my own.
"I think you're right, Linda. These probably would work better. I
wonder if he's having a problem in there." I heard her muffle a giggle,
too. "Maybe I should check."
She knocked on the door and walked in without waiting for me to
answer. "Oh my, you seem to be having some difficulty. Here, let me show
you. The first thing, is that you haven't adjusted the straps properly.
You're going to need as much length here as you can get." She fiddled with
this little buckle-like thing and then pulled the cups down a bit. "That
should be easier," she said, as she helped guide my arms through the
straps. "Usually, you'd put your arms in first and then hook it up, but
I'll bet you hooked it up in front, first, right?"
I just nodded. "I thought so. You'll get better with practice"
What did that mean, I thought? She smoothed out the straps, tugged on the
cups, tugged on the back, ran her finger around the back. "This fits well
here, so I think we have the right size. We don't have this size in a
smaller cup, though. What are you going to here?" she asked as she tweaked
my empty cup.
"I'll probably just stuff it with something," I mumbled.
"Socks don't work very well," she said. "They get lumpy and they
just don't look right. We have mastectomy forms but they get very
expensive." I blanched. "What you can do, though, is to buy a pair of
knee-highs and fill them with about a cup and a half of birdseed, or you
could even do the same thing with a baggie and about the same amount of
water. Both will fill these out nicely.
"Stay right here. I'll be right back." She didn't close the door
to the dressing room behind her, so I lunged toward the doorknob, just as
that teenage girl walked past me towards her own dressing room. I could
have died. After a couple of minutes, Andrea knocked. "Are you decent,"
she said, but she didn't wait for an answer before she came in.
"This is called a waist nipper," she said. "It's a girdle with a
high waist. Wear your tights under it and they won't sag, but more
important it will give you a little definition here (and she put her hands
around my waist) and here (as she placed her hands on my butt). This is an
XL and it should fit but I think you should try it on. You'll have to
leave your underwear on. Here." She gave me the girdle and left, again
without closing the door.
I was out of my league. Not only could I not figure out which end
was the front, I couldn't imagine how I could put these on over my boxer
shorts. I just held them stupidly until Andrea knocked again and opened
the door. "I thought you might have some problems," she explained. "They
go on this way," she explained, showing me which way was the front.
"Wiggle them up your legs and when you reach the top, pull up the waist.
Then hook all these hooks and you're all set. By the way, these will never
work with the undies you're wearing now. I brought you some panties.
You'll have to buy them but they're on sale and I'll discount them when we
ring up the sale. Let me know when you're all set."
The panties were simple, white briefs, for which I was grateful.
After she left, I slipped out of my boxers and put on the panties, which
seemed to fit like a second skin. Then I slid the girdle up my legs,
pulled up the legs and hooked the hooks, just as instructed. It took some
effort to attach all those hooks, but when it was all done it didn't feel
all that uncomfortable. In fact, I was more than a little excited, and I'm
not sure that this wasn't obvious when Andrea came back into the dressing
room, this time without knocking.
"I think this is just about perfect," she exclaimed, as she tugged
a little on the legs and then ran her fingers around the top band. "Don't
you think so?" I nodded mutely. "Oh don't be such a fuddy duddy. This
will give you a nice, girlish figure and, who knows, you may enjoy it! Get
dressed and bring your things to the counter and we'll ring you up."
As soon as she left, I got out of those things as quickly as I
could, which frankly wasn't all that quick as I was still having some
problems with these hooks and having the hooks in the back of the bra was
an ingeniously torturous device. Eventually, though, I was back in my
flannels and jeans and standing in front of Linda at the cash register with
my new "treasures."
She took the bra, girdle and panties from me and elaborately folded
them while placing them back in their boxes. "Will that be all sir?" she
asked.
"Umm, yes."
"Would you like to join our bra and panty club.? Buy 10 panties or
5 bras and get one free?"
I just stared at her.
"It's a promotion we're running right now and I have to ask," she
said, with a conspiratorial air. "But it is a really cool deal if you're
interested."
"I don't think so," I replied. She rang up the sale and handed my
purchases. "Thank you very much and we hope to see you again soon, sir."
She positively beamed. I mumbled my thanks and tried to get out of the
store as quickly as I could without knocking anything over.
I left the store and took a deep breath. While I felt some relief,
I don't know whether I was more relieved that it was over or that I didn't
die from embarrassment. I didn't think I could do what I just did, but I
did and Catherine, Andrea and Linda were all nice and my essential parts
hadn't dropped off when I tried my new skirt or my bra. This may not turn
out to be as bad as I thought.
I assessed what I still needed to do. I needed shoes and I needed
to do something about my hair and makeup. I didn't remember if Catherine
recommended any shoe stores so I just started to circle the mall. The
first shoe store I saw was all athletic shoes and the next one had a clerk
who looked like Al Bundy leaning on the counter. I just couldn't see
asking him for help so I walked on. A few more stores down I saw a store
that looked promising. All the shoes in the window were women's, both
casual and dress, and both of the clerks were women in their 20s. One had
short, black hair and the other longish, brown hair pulled back in a
ponytail. There were customers in the store right then.
I went into the store and started looking around, while the two
women continued to chat with each other. After what seemed like an
eternity, the one with black hair asked "Do you need some help?"
I walked over to the counter. "I think I do. I had a bet with my
wife and I have to watch this Sunday's game in drag. Right now," and I
raised my two bags, "all I need is shoes."
"Oh really," the black-haired one said, raising an eyebrow. "This
could be fun," she remarked to her associate. "Do you know what you're
looking for?"
Why did everybody ask that question, I thought to myself. "Uh, no,
not exactly. Whatever fits and whatever goes with what I've already got, I
guess."
"Can we see?" she asked.
"Sure, I suppose." I gave her the bag from Laura Brown's. She
pulled out the skirt and held it up against my waist. I wasn't expecting
this. There were no racks to hide me, just a big, wide glass store front
that was open to the entire mall. I quickly backed away but she reached
out and put her hand on my shoulder.
"I'm sorry, I didn't want to embarrass you. I just wanted to see
what we have to work with. OK?"
I nodded.
"That's a pretty skirt and we've got lots of things that will go
well with it. What else are you wearing.?"
I pulled out the sweater and the brown tights.
"Oh that's very smart. You're gonna look great honey. Don't you
think he'll look cute, Suzy?" She asked her partner.
"Absolutely." They were talking to each other as if I weren't even
there.
"What do you think - penny loafers might work, or faux alligator
loafer, maybe." Suzy picked up a couple of shoes from the display and held
them up for my approval. They both looked fine to me, but what did I know?
"They're a little plain, Suzy" the black-haired woman said. "I
think an outfit like that needs something with a little more character."
She turned to me. "Why don't you have a seat, sir."
As I was doing what I was told, she reached into a little box on
the counter. "Take off your socks and these on or we'll never get a proper
size." She handed me a couple of little balls of nylon that I found out
later were called peds. It took me a second, but I got them on. I felt
like an idiot.
By this time, Suzy had gone off to help another customer (who was
looking warily at me). My saleswoman squatted down with that contraption
they use for measuring foot sizes and after fiddling around a bit told me I
was a 9 and that she would be right back and that I should relax (how many
times had I heard that today!).
Just as promised, she came back with an armload of shoeboxes. As
she tried on shoe after shoe on my feet, she kept chattering away at me and
I didn't hear a word. I was frozen with fear that someone I knew would see
me trying on women's shoes over ped-covered feet in this glass enclosed
shoe store in the middle of a popular mall. She tried on big heels and
little heels and shoes with straps and shoes that covered my toes and shoes
that didn't cover my toes and some of them fit and some of them didn't but
at this point I was dazed.
"So, what do you think?" She was expecting me to make a decision
and my mind was absolutely blank. I looked down at my feet and for reasons
I'll never understand, like a bolt out of the blue, what I saw made sense.
I was wearing (left foot only) a 2" clunky heel with a big brass buckle and
an open toe and I liked the way it looked and I liked the way my foot felt
in it.
"I think those will be fine, " I squeaked.
"I thought so. These will look really nice with your outfit. They
really do go together." She put the other shoe on and told me to stand up.
I did, and shook a little when I got upright, but then felt fine. I
thought the shoes looked great and my feeling of weirdness completely
disappeared, until I saw one of Suzy's customer's grinning at me. I sat
down in a hurry and my black-haired saleswoman smiled and said, "Don't
worry about anything. You'll never see her again, and besides, you've
chosen a really great pair of shoes."
She took off the shoes and put them back in the box and headed back
towards the register. I couldn't figure out what to do with the peds, so I
put my socks on over them and followed her. After she rang up the sale,
she asked "Will there be anything else - ooops - sorry - force of habit,"
took my credit card and finished up.
I thanked her and as I was leaving, she gave me a wide smile and
told me to "have a real good time, OK? By the way, we'd love to have a
picture if you're OK with that." I must have blushed a dozen shades of
crimson as I walked out, but to tell the truth, I wasn't sure if I was
blushing because I was embarrassed or because I was beginning to realize
that I starting to like the idea of what I was doing.
The last thing on my list was hair and makeup. I knew that if I
went into the local drugstore and bought a bunch of stuff and did it myself
that I'd look more like Bozo the Clown than anything else, but I had no
idea of what else to do. I knew I needed help but a beauty salon? The
idea seemed ridiculous but having already tried on a skirt, a bra and 3"
heels how much more ridiculous could I get?
On the ground floor of the mall near the offices and near the
parking garage (thus on the way out) was a shop called Rita's, written with
big, curly script across the windows. Underneath, in smaller, but equally
florid type it said hair - cosmetics - nails. I figured that this was the
kind of place I needed, so I went in. Fortunately, there was nobody in the
place except for a tall, big-haired redhead sitting in one of the customer
chairs and a forty-ish woman with short, black hair sitting behind the cash
register sipping coffee and reading Vogue.
I paused in front of the register. "Melpyu?," she said, without
looking up. After a second, it dawned on me that this was a contraction of
"May I help you?"
"Yes, I hope so." I launched into my sad story. "I've lost a bet
with my wife and I have to spend this Sunday with her in drag. I've got
the clothes (and I waved my bags at her) but I'm going to need help with my
makeup and hair, I guess, but not today, first thing on Sunday. Or right
after you open, because you probably don't open until noon. Can you help
me out?" I was babbling and she was staring at me but at this point my
mouth stopped.
After a couple of seconds, she reached out and took hold of my chin
and moved it to the left and then to the right. Then she stood up and ran
her fingers through my hair (which is fairly long for a man's but not real
long) a couple of times. Then she sat back down and exhaled loudly.
"Lemme see what's in the bags." I gave her the bags and she poked around a
little, then stared into space for a couple of seconds and turned back to
me.
"Y'know, the girls I usually have working Sunday would probably get
you arrested but for something like this, I'll come in myself."
Then I exhaled.
"What I want you to do is this," she said to me. "I want you to
shave real close as late as you can Sunday morning. And I want you to wear
something that ain't too male or too female. Jeans and a T-shirt would be
OK, but you ain't gonna look like a girl coming in and you ain't gonna look
like a boy going out, so you gotta straddle. And you prob'ly oughta wear a
baseball cap or something with a bill that you can pull down over your face
when you leave, 'less you think you can be comfortable being seen in
eyeshadow 'n shit. You think you can do that?"
"Yes" I replied with more confidence than I really thought.
"Alright, then. We open at noon, but if you came a few minutes
early I'd let you in. And honey, one more thing. You forgot jewelry."
I put my purchases in the trunk and drove right home. I was so
relieved to find that Carol's car wasn't in the driveway. I hauled the
bags upstairs and hid them in the corner of my closet, underneath the
luggage. I then poured myself a stiff drink and sat on the back steps,
watching the late afternoon sun while ruminating on the day's experiences.
I couldn't quite reconcile the embarrassment I felt with the image of my in
my new skirt, sweater and shoes, with curves in all the right places. In a
way, I couldn't wait for this Sunday to come.
I didn't get any work done on Friday because all I could do was
think about those bags lurking in my closet. I left the office as early as
I could and headed back to the mall, where I picked up a pair of clip-on
earrings, gold colored with an imitation opal in the center and some
gold-colored bangles. I marched right into the store, right over to what I
wanted, made my selections and brought them right over to the counter. I
was so proud of myself.
Carol was in the kitchen when I got home so I had to sneak the bag
past her, but she still wasn't talking to me or paying any attention to me,
so I didn't have to sneak too hard.
Saturday was awful. I still couldn't quite figure out whether I
was terrified of getting all dressed up on Sunday or I couldn't wait to put
on my new skirt. I couldn't concentrate on anything else and all day I
kept bumping into things and dropping things. I was a mess. The only
thing I did successfully all day was make my breasts out of baggies and
water, the way the woman at Under It All instructed. I was amazingly
precise when doing that. ***************
Finally, Sunday morning arrived. Although I hardly slept a wink, I
stayed in bed until Carol went downstairs around 9:30. I went into the
bathroom and took a long look in the mirror.
"Here goes," I said to myself and began to shave. I usually use an
electric razor but I bought a safety razor for the occasion to get a closer
shave. I was extra careful and took a long time and hoped that Rita would
approve. As I stood there washing my face, I decided in an impulsive
moment to do my legs as well and put the razor and shaving cream in the
shower. After wetting down under the hot spray, I foamed my legs, took a
deep breath and did it! There were a couple of moments when I felt like a
pretzel (ever try to shave the tops of your feet?) but I did it. As I
toweled off, I couldn't begin to describe the feelings I got as I rubbed my
smooth, now hairless legs.
Back in the bedroom, I got my bags out of the closet and found the
tights. I'd watched Carol putting on pantyhose before, so I bundled up
each leg in a ball and then sort of rolled them up my legs, then tugged the
top up to my waist making sure that it was snug where it ought to be snug.
So far, so good.
The girdle was next and I pulled it on over the tights and then
spent an agonizing couple of minutes hooking all those damn hooks, but when
I was done I glanced in the mirror and to my surprise, I had a waist, I had
a butt and I didn't have much in the front. Now it wasn't much of a waist
and it wasn't much of a butt, but it was a whole lot more that I had about
three minutes ago. The bra was next and I put it on just like Andrea at
Under It All had showed me. I didn't put in my baggie/falsies yet. That
would come later.
Then I put on my new sweater and a pair of jeans. A big, gray
sweatshirt over the sweater, a pair of dingy "white" sweatsocks over the
tights, my sneakers, a light jacket and my Giants cap and I fairly streaked
out the house to the car. I told Carol as I was leaving that I had a
couple of errands but I don't know if she heard me or if she cared.
As I pulled out of the driveway, I realized that I had at least an
hour to kill before Rita's opened so I just sort of drove around aimlessly
once I got out of my neighborhood. At first, the tightness of the girdle
and the bra and the feeling of material hugging the length of my legs was a
little disconcerting but not unpleasant. But the more I drove around, the
more pleasant it became. I don't know if I could ever get used to having a
bra stretching across my chest and over my shoulders, but this rest of this
wasn't turning out to be too bad at all. Realizing that made me more
confused than ever.
I pulled into the mall parking lot around 11:30 and just sat in my
car gathering courage. After a few minutes of deep breathing, I opened the
door and marched out towards Rene's. I went straight up to the door and
Rene was there to meet me. She grinned a bit and said "I wasn't sure you'd
come." She beckoned me towards one of the chairs towards the back.
"Have a seat, hon. My name's Adelle and you're...?" She looked at
me expectantly. I looked at her with confusion and then looked at the sign
on the window. "I bought this place a couple of years ago and it seemed
stupid to replace a perfectly good sign. You still haven't told me your
name."
I did and then she tied a bib around my neck and adjusted my head
to and fro until she was satisfied. "I want to start with your hair
because I want to try something and I won't know if it'll work until you're
ready to leave."
I mumbled an "OK."
"I think I might be able to use your own hair so you won't need to
wear a wig," and she grabbed a couple of brushes and a comb and started
attacking my hair. Attacking was the only work to use. She brushed it
this way and that, pulled it up and brushed it down and just did all kinds
of things to it. When she was finished, instead of sweeping across my
forehead my hair fell in bangs. Instead of being parted on the left and
swept back, it fell evenly from a part in the center. She picked up a
brush that looked like a vicious drain cleaner and curled the hair that now
dropped below my ears around it and then sprayed some stuff on it. When
she unwrapped the hair from the brush, it held a little of the curl
inwards. She did this all around the bottom.
When she picked up the scissors, I almost panicked. "Don't worry
hon, I'm not going to do anything that anyone will see when you comb it
back into your boy style." What she wound up doing was evening my bangs
and trimming some rebelliously uneven strands from above my collar.
"There," and she showed me her handiwork in the mirror. It was
definitely a woman's style and I thought it was fine but that I looked
silly in it.
"Great," I said, but I don't think I sounded real enthusiastic.
"I want to see how this holds up while I do everything else. If
it's still there when I'm done, I'll show you how to brush it to keep it
fresh and you'll be all set. Then, if you want to, you can comb it back to
your boy style. Now let's do your nails."
She reached into a small tray and dabbed something on the index
finger of my left hand. "This is an adhesive that will hold your nails in
place. Your wife will know how to take them off," she explained as she
finished with the glue and then placed a long, sculpted piece of plastic
over my own nail. It looked to me to stick out about six inches from my
fingertip but subconsciously I knew I was exaggerating.
She finished the rest of hands, then spent a few minutes with a
nail file sanding, poking and pushing things around until she was
satisfied. Then Adelle sat back and took out some nail polish and began to
paint. The color was a deep, rich reddish/brown that reminded me of
mahogany. When she was finished, I couldn't describe how amazed I was at
how they looked or how strange they felt.
"Now keep your hands still so they'll dry properly and I'll get to
work on your face. You've already shaved, I hope?" I nodded. "Good."
With that, she started to work. By this time, another couple of
her assistants had come in and glanced at us, stifling giggles but not
saying anything. I began to wonder how I was going to get out of here
since the mall was going to be open.
She applied a creamy kind of thing all over my face, smoothing it
out first with her fingers and then with a cotton ball. When she lifted my
bangs to cover my forehead and they fall back into place, she smiled.
Some powdery things followed. First one that was applied all over
the creamy stuff she just applied, then a couple of different ones just to
my cheeks. I just stared off into space. I was afraid to glance at a
mirror.
"Now I want you to hold perfectly still," she said as she pulled
out the mascara (I knew what this was, because I'd heard Carol call it that
when she used it). She leaned in real close and began brushing my
eyelashes, upper and lower. Then she reached for a couple more different
things and began to brush my eyelids and the area under my eyebrows.
"Your brows are a little thicker than I'd like. You want me to
thin them out? They'll probably grow back." My eyes must have registered
major alarm, because she shook her head and said "I didn't think so. I'll
just try to shape them a little." She took a tiny comb and began to comb
my eyebrows.
Then, after she was done with that, she stepped back and looked at
me. I was so self-conscious I was sure I was blushing furiously. She
touched my chin and moved my head a little this way and that and then spent
the next few minutes dabbing and poking at my with various things.
"Blink." I did. "Shake your head." I did.
"Well, I think I did a pretty good job - how 'bout you hon?" She
made me look into the mirror and what I saw shocked me. I looked good. I
looked very good. Staring back at me was the face that could have belonged
to a successful businesswoman. Short, no-nonsense haircut, dark eyes
touched with shades of gold and brown and flawless skin with a touch of
color on the cheeks. The only thing missing was lipstick (even I knew
enough to know that lipstick was missing.
"I didn't put the lipstick on hon, because it would show up too
much when you leave. If you pull your cap down low, most of your face will
be hidden and folks will probably not notice that you're wearing makeup.
Put on the lipstick now and they're gonna know." I silently blessed her.
"So what I want you to do is to pay real close attention when I show you
what to do and you can put it on yourself when you get home."
She showed me what to do and then gave me the tube. She also
showed me what to do with my hair. "After sticking it under that cap and
driving home, it's going to need a touch up."
When it came time to pay her, I had the hardest time trying to get
my wallet out of my pants with those nails. When I finally succeeded, I
realized I didn't know what the tipping conventions were in a place like
this. I gave her a big tip anyway.
"You're usually not supposed to tip the owner," she said. "But in
this case, I think it's appropriate." She smiled. Have a good time today,
hon."
As I opened the door to leave, I heard Adelle call after me. "Hey
hon?" I turned around. "Hands in the pockets until you get to your car"
I drove home as fast as I could, making sure to keep my hands on
the bottom of the steering wheel. When I got home, I headed straight
upstairs, catching a glimpse of Carol sitting on the couch reading a book.
I took one of her brushes and brushed my hair back into condition. Then I
took out my lipstick and carefully applied it to my lips exactly as Adelle
had instructed.
Off came the sweatsocks, the jeans and the sweatshirt (I should
have waited to fix my hair, I said to myself). I took my skirt out of the
closet and put it on, pulling the belt tight to emphasize my waist. I
knotted my scarf and draped it around my neck and over my left shoulder.
Next came the earrings and the bracelets.
I started to bend over to get my shoes, but about half way down I
thought that bending over wouldn't be very ladylike so I squatted down and
then sat on the bed to put them on. As I stood up I didn't know what to
expect, but when I straightened up and looked in the mirror, I felt and
looked simply wonderful and I was amazed at myself.
A quick check in the mirror made me remember that I forget a couple
of very important items and I got my "breasts" from the drawer and put them
in place. Readjusted the sweater and the skirt. Rebrushed my hair,
squirted on a little of Carol's favorite perfume and then walked down the
stairs as quietly as I could.
In the kitchen, I placed the video, two glasses and the bottle of
wine on a basket. One last glimpse in the downstairs bathroom mirror and I
was ready.
I peeked into the living room and said "Ta da," in as quiet,
breathy and romantic a voice as I could muster. Then I swirled into the
room, placed the tray gently on the coffee table and spun around in front
of Carol.
The expression on her face was priceless. Surprise gave way to
shock which gave way to a couple of lonely tears running down her face and
then the widest smile I'd seen on her in years. All the money, time and
embarrassment of the last few days was worth it just to see the smile on
her beautiful face.
"Honey, I love you so much," she said as she stood up and hugged
me. Our breasts pushed together and as we kissed and hugged with a deep,
loving passion.
"I love you too Carol and I'm so sorry for the way I've acted."
I'd tell you the rest of this story, but there are some things
between a husband and a wife that must remain private.