The Dance
By Jamie Lynne Williams
[email protected]
It was Wednesday morning. Jack was going to do it. He signed up; he paid his
money; now it was time to do this. "This" was attending his first cross
dresser's overnight event. He had attended a few of the monthly meetings at
his local chapter; he went dressed as Jack for the first meeting, then as
Jill for the next four. Now it was time to leave the city and spend four days
dressed.and hopefully have a good time. As Jack packed his bags he thought
about the last year and how much had changed in his life. Here he was a very
successful sales executive. He managed a national sales force. Salary and
bonus was over $200,000 per year. He lived in a huge house, and here he stood
folding panties and placing them lovingly into a suitcase. He knew that he
had always wanted to do this. He finally had the chance to do this, and he
couldn't chicken out now.
He had enough clothes for four days for both Jack and Jill. He smiled as he
folded the lingerie and placed it into the suitcase assigned to Jill's
clothes.
He hoped he wouldn't be Jack too much over the next few days. He was excited
to meet new folks, and to learn more about this passion for cross-dressing.
Jack was especially interested in getting better at makeup and hair styling.
As a guy he was never one to fuss about his looks. He always said he combed
his hair once a day whether it needed it or not. He never worried about
cosmetics. All he ever put on his face was shaving cream---except for the few
furtive times in hotel rooms when he tried to apply make up, and usually
ended up looking like Mimi from the Drew Carey Show.
He had gotten a little better as of late. The girls in the local club were
wonderful. Especially one named Jane. She had introduced Jack to the local
Mary Kay rep. She was a great middle-aged lady who happened on to the cd club
totally by accident, and she loved them. Jack packed Jill's makeup, he could
do an okay job now, but he was hoping to be able to get an appointment with a
professional at the conference to do him up right. Especially important were
the dances on Friday and Saturday night. Jack wanted Jill to look her best.
He had been dressing in secret on and off for at least thirty-eight years.
When he was twelve it was his sister's or his mother's clothes. As he got
older he bought and threw away several wigs and many outfits. He was never
able to act on his desire in his adult life. His wife would never understand.
So like so many of his 'sisters' he lived his fantasy in secret.
All that changed a year ago. His wife and son, his youngest child, were on
their way home from a college visit, and were killed by a drunk driver. His
older children, two daughters, were living away from home. Jack was now on
his own for the first time in his life. He had been coping well. The girls
were a great help, and his family was wonderful. But he had come to enjoy the
freedom to come and go as he pleased. He enjoyed setting up the gym in the
second floor master bedroom and moving his and "her" stuff downstairs into
the first floor master bedroom. He had a lock on the closet where Jill kept
her clothes--just in case one of his daughters or the rare overnight date
decided to go exploring.
Along with the support of his family, Jack found that there were any number
of women in the neighborhood and at work that were willing to "console" him.
There were two divorced women on the block who were at his doorstep within
two weeks of the funeral. Jack accepted the first woman's offer to bring food
over--just to be nice, and because he didn't know how to say no for a third
time. She arrived at 6:30 Wednesday night with the supposed dinner, and was
wearing a dress she was poured into, and had little in the way of food, but
two bottles of Merlot and a Johnny Mathis CD! Jack couldn't do it. She was
certainly good looking enough, but it was too soon. He asked for and got a
rain check. One month later she was back, and this time she wound up spending
the night. Jack couldn't believe this woman. She lived two doors away for ten
years, he knew here and her ex-husband pretty well, but when she got out of
her normal clothes, he discovered she was a rubber fetishist. She had a
suitcase full of clothes and toys. She not only wanted to be dressed in it,
she wanted the smell of it to permeate the room. It was interesting-actually
it was a lot of fun--but not what Jack was into.
The second woman was terrible. She was divorced as well, and had three kids.
Jack knew her and her ex-husband as well. She had Jack over for dinner on a
Saturday evening. The kids were at her ex-husband's apartment; Jack was kind
of "weirded"out by the whole thing. She seemed desperate to make herself
available to him. After dinner they went into the family room and she
literally threw herself at him. The night was awful. He didn't really want to
do it, and she was so strait laced and inhibited, that no matter what he did
to lighten her up, she was as tense as a board, and wouldn't try anything.
Jack left shortly before dawn promising to call her.
He had become a very eligible bachelor not only in his neighborhood but at
work as well. After four months Jack decided to keep things platonic on all
of his dates and with all of his relationships. He had already started on a
regime that would make him "all that he could be" as a she. He hired a
personal trainer at the fitness club he had joined. He started on rigorous
physical training and diet sessions. Jack determined that he wouldn't start
buying a wardrobe until he was down to the shape and fitness level he wanted.
Then he vowed he would start collecting a wardrobe in earnest. But before he
did that, he needed to get into shape.
At 6'3" and 225 pounds, he needed a lot of work. It took ten months but he
lost 50 pounds. His friends and neighbors were constantly questioning him.
The weight loss caused them concern, and they wanted to know if he was okay.
He deflected their concern by saying he was coping with his grief by working
out. Three-quarters of the way through his weight loss program, he made
another decision he couldn't have made when he was married. He actually used
his vacation to have some cosmetic surgery. He wanted to have some of the
flab around his waist that just wouldn't go away removed, so he had
liposuction. He had his eyes and his neck fixed (tightened the doctor called
it). He scheduled it for a time when he could take three weeks vacation, and
he knew that his daughters would not be coming home from college. Once he had
healed, and was sure he could keep off the weight, he started on his
wardrobe.
His sisters at his local CD club couldn't have been nicer. They helped with
make up and with hints on what to buy and where to buy it. They directed him
to all the right places. He worked up the courage to be waxed, and they
guided him to the right place for that as well. Once he had recouped from the
waxing, he wanted to wear nylons every minute. The feel of the hose on his
now hairless legs was wonderful. Even the nightgown he wore to bed felt
exponentially better.
He was still reluctant to go out dressed unless it was to a meeting or to
someone's house for a party. The occasional party at the one bar in town that
welcomed cross- dressers was his only other time to go our as Jill in public.
He just didn't have the confidence to go out dressed. He wanted to, he just
was not sure of him/herself. He was also paranoid about getting pulled over
by the police, or being spotted by someone he knew pulling in or out of his
driveway.
He decided that if he went out of town to one of the big weeklong
cross-dressing events, he would be able to get the courage to go out more
often back home. So he signed up for one of the better-known events. Now it
was time to go. As always, the road to hell is paved with good intentions.
Jane from the club, who promised to go with him, and had actually suggested
the trip in the first place, had to cancel at the last minute. She was also
in sales, and one of her key accounts was in jeopardy. While cross-dressing
is an obsession--you still gotta eat. So Jack was off to the airport by
himself.
The travel was not a big deal--especially since he went dressed as Jack. He
had spent most of his life on the road, and knew New York City very well. He
had been there more times than he could number. It was bigger than Chicago,
his hometown, but he loved going to New York. No city in the U.S. would
intimidate Jack, but how would Jill survive? The plane trip was uneventful,
there was a neighbor on the plane, but he was connecting to an overseas
flight, so there was nothing to worry about there. The cab ride was
uneventful too, but Jack was flush with anticipation.
The hotel was large, old and would easily accommodate the attendees. It was
not a hotel that Jack would have selected if he were traveling on business,
so that should ensure him not seeing anyone that he would know. But, Jack had
enough experience to know that Murphy's Law had an opportunity to go into
overdrive on this trip. Jack checked into the hotel, as a member of all hotel
points programs ever invented, Jack received an upgrade to a small suite. He
was pleasantly surprised by the upgrade; he had not stayed in one of these
hotels in quite a while. He thanked the clerk, handed the check-in envelope
to the bellman and headed up to his room. His head was on a swivel as he
walked through the lobby. He was looking for cross dressers, but failed to
notice any women who looked like they were men.
The bellman took Jack's bags and directed him to the elevator that would take
them up to his room for the four nights. The suite was much nicer than Jack
had expected. It was on the top floor of the hotel. It was divided into two
rooms, a bedroom with a king-size bed, and a very nice sitting room. The
bellman talked nonstop about the amenities of the hotel. He went on and on
about how the renovations would bring the property to its previous
prominence. He listed several good places to eat, drink and pick up women,
without asking whether or not Jack wanted to know about them. Jack smiled as
the bellman mentioned the bars where the action would be this weekend. Jack
over tipped the bellman and thanked him for all of the information. The
bellman acknowledged the generous tip and turned to leave, but as he reached
the door, he turned back and leaned slightly closer to Jack, and in a very
hushed tone, told Jack to be careful in the hotel this week. He said, "The
whole hotel is going to be filled with queers who dress like women. I
wouldn't spend any time in this building if I were you. They should warn guys
like you when these kind of events are being held in the hotel."
Jack pretended to act surprised. He asked what the event was, when it
started, how many people were going to be in attendance and if the bellman
would be working over the weekend. The bellman knew everything. He was more
informative than the brochure on the event. He said that it had been held
here before, and really it was worth walking through the lobby on Friday and
Saturday evening before the conference dinners. Yes, he said, he would be
working over the weekend, and with that he grimaced. Jack thanked him for the
information, and listened for the door to click shut as he bellman left.
Jack didn't know whether to laugh or be angry. He laughed at the assumption
that Jack wouldn't be one of the men in dresses this week. But he was angry
at the comment "queers who dress like guys"; it was a typical uninformed
reaction to cross-dressing. Jack thought about all the cross dressers he had
met over the years and how many were heterosexual, and how many were very
well educated and how many were far better people than the ones who were
condemning these men in skirts. Before Jack put it out of his mind he made a
mental note to find the bellman. He made sure he would remember his
name--Mike. He wanted Jill to meet him.
Now to unpack, Jack tossed the three suitcases onto the bed and naturally
unpacked Jill's bags first. He carefully hung up the dresses and the suits.
He placed the lingerie in the drawers careful not to crush anything. The wig
cases were unzipped and the light brown, almost blonde wig that Jack so loved
was put on the credenza in the sitting room he placed the champagne colored
one next to it. Jack took the cosmetics case and walked into the bathroom.
Wow! He hadn't gone in there while Mike was there. The room was huge. It had
a double sink, and a chair to sit at the counter while you did your makeup.
It had a magnifying mirror to help with makeup as well. But the highlight of
the room was a Jacuzzi! It was certainly large enough for two people Jack
thought, but he was not looking for that on this trip. He wanted to
learn--learn how to better do his makeup, learn how to better style his hair,
learn more about why he needed to do this. Jack laid out the cosmetics on one
side of the bathroom, and when he returned with his "Jack stuff" he laid that
out on the other side. It looked to the casual observer--hopefully any
maid--that there were two people staying in the room.
At 4:00 in the afternoon Jack had everything put away. He called his office
to be sure that there was nothing that needed his immediate attention--there
wasn't; everything at the office was calm. He decided that a work out would
be the best thing he could do now. He called the health center in the hotel
to find out what kind of equipment they had, and was once again pleasantly
surprised. It sounded good over the telephone. Jack went to the "Jack side"
of the dresser and donned his work out clothes. An hour and a half later Jack
returned to his room drenched in sweat, but feeling great. He went into the
bathroom and stripped down to his birthday suit. He checked his body
carefully in the mirror. The body waxing that he had last week was still
keeping him hairless from the eyebrows down. The fact that he almost fasted
for the last three days caused his already slim body to look good despite his
fifty years. Jack smiled at this newly acquired narcissistic streak. He
decided to shower, and then jump into the hot tub.
Forty-five minutes later Jack emerged from the bathroom. He had showered and
bathed. The Jacuzzi was truly an unplanned bonus on this trip. While the hot
water swirled around him, he sipped a diet coke and reread the agenda for the
rest of the week. He then worked on the crossword puzzle from the flight
magazine, and finally decided he had to shave his body. Jack was sure that
this was a pain for real women, but for him it was still a turn-on to feel
the smoothness of his newly shaved body. Jack decided he needed a sushi fix,
so he dressed--as Jack--and headed out to one of his favorite Japanese
places. Once again Jack was trying not to miss anything as he walked down the
hallway in the hotel, on the elevator, and as he slowly walked through the
hotel lobby. He didn't see anyone who looked like they were there for the
same reason that he was.
The sushi bar wasn't crowded. Jack ate, and skipped any alcohol; he wanted to
keep his wits about him for this trip. He wandered up and down the streets in
the neighborhood for a while. He thought about going to one of his favorite
Irish bars for a pint of Guinness, but thought he would check out the hotel
again first, so at about 10:30 he headed back to the hotel.
The lobby was practically deserted. Jack was starting to feel uneasy. He
wondered if he was going to be the only person in attendance for the Thursday
sessions. He quickly put that out of his head, he knew that would be
ridiculous. He asked the young girl at the front desk where the hotel bar
was, and was directed around the corner of the lobby. Jack opened the door
and walked into the dimly lit room. It was large, and to his surprise
reasonably crowded. Jack walked up to the bar and ordered a beer. As his eyes
adjusted to the darkness, he realized that this is where the conference was
unofficially starting. Jack now almost wished he had dressed as Jill. But he
did a quick calculation in his mind as to how long it would take him to
transform himself--too long. He also went through what outfits he would wear,
and decided he would just have to be Jack.
The bartender gave Jack his beer, and Jack had him put the charge on his
room. Jack turned around, and faced the crowd. There were at least fifty or
sixty people in the room, and they all appeared to be cross dressers, or
their friends. Jack's eyes panned the room. He wasn't sure what he was
looking for, but he scanned the room, and as he got about three-quarters of
the way around the room, his gaze was met by a smile and a wave. Jack didn't
recognize who it was, but she was motioning him to come over and sit with her
group. Confident as Jack, he didn't hesitate to walk over to the group. There
were four "girls" sitting there. They stopped talking and the girl who
motioned for him, pointed at the empty chair, and said, "how come you're not
dressed? You must be a newbie. My name is, Regina, this is Mary, Joan and
Rae. And who are you?"
Jack smiled, and said, "Well, right now my name is Jack, but hopefully for
the next time you see me and for the next four days I will be answering to
Jill." Jack sat down at the table with the girls. He found out that they were
from another large mid-western town. He learned that Regina, Rae and Joan
were veterans of this conference. Mary, who appeared to be the youngest and
by far the prettiest, was a first timer like him. Jack offered to buy a round
of drinks as a way of joining in with them. His offer was quickly accepted,
and within just a few minutes they had accepted him as a friend.
Jack asked how they could be so sure that he was here for the convention.
Regina laughingly said she was psychic. She could spot a closet cross-dresser
at a convention better than anyone. She said no matter how hard he tried to
look disinterested and cool, she could read his eyes. She said she could read
eyes like the Sunday funnies.
They discussed the upcoming week. Jack asked about the sessions on Thursday
and Friday. Joan said forget the sessions. She was planning on going to some
after hour's place tonight, and partying until dawn. She said that Jill would
only see her when it was dark! Regina suggested that the make-up session and
the wig styling session Thursday afternoon would be worthwhile. Mary chimed
in that she wanted to attend the session in the morning that had a
psychologist discussing the whole phenomenon. Jack looked over at Rae, who
was absolutely elegant. She said that she was sleeping in, and then she would
be off to shop. She said that she already had appointments at two very trendy
clothiers, but she said it was great that they had met Jill, because they
didn't want Mary to be alone. Regina agreed. She said she wasn't going to get
up early either, but wanted Mary to have someone to go to the sessions with,
and Jill would be the person.
So they agreed that Jill and Mary would meet for breakfast and go to the
morning session. Regina would join them for lunch and the afternoon sessions.
They all agreed to meet in the bar Thursday night and go to dinner together.
Joan said she knew just the place. The girls laughed. They all said not that
S&M club again. The food is terrible there. "Who goes for the food!" laughed
Joan. At one in the morning the lights came up in the bar. The girls got up
in unison, and headed up to their respective rooms. Jack found out that Rae
and Mary were rooming together and Joan and Regina were sharing a room. When
they got to the elevator Joan said, "see you old timers! I am off to find
trouble!" They all told her to be careful, and Joan said she had never been
careful in her life and headed out to find a taxi, laughing all the way to
the doorway.
Jack thanked the girls profusely as they exited the elevator. He invited Mary
to have breakfast upstairs on the concierge level with him. She accepted, and
they agreed to meet at 8:30 Thursday morning. Jack felt elated as he walked
to his room. The girls seemed genuinely nice. He now had someone to attend
the sessions with and to sit with at the dinners. He took off his Jack
clothes. He hung them in the closet, and as he walked to the dresser he had
the distinct feeling that he had worn his Jack clothes for the last time this
week.
Jack took out the dark green, satin baby doll pajamas. He looked at them, and
thought, "you know Jill, you are too old for these--but they feel great!" He
slipped the short top on, and pulled the satin panties up his legs. He went
into the bathroom and removed his contact lenses. He looked into the mirror
at the incongruous looking image staring back at him. There was a flat
chested hairless guy wearing a young girl's nightie staring back at him. He
also noted that this figure had a rather serious hard on as well. Jack
grabbed a washcloth and headed back to the bedroom. He would have to take
care of the hard on before he would ever get any sleep.
Thursday morning the alarm clock jolted Jack awake. He sat up in the bed and
was instantly totally alert. He was nervous, excited and aroused all at the
same time. He grabbed the remote control and turned on the television. After
twenty-five years on the road he had some serious habits. One was to always
have the television on while he was in the hotel room. The Today Show was
droning on about something he didn't listen to as he removed his nightie, and
padded into the bathroom. He turned on the shower and proceeded to sit on the
toilet as he pondered the upcoming day. He smiled as he thought of being
Jill. He finished his morning constitutional, and as he stepped into the
shower, he made the mental decision that he was stepping out of Jack and into
Jill at the same time.
The hot shower felt great. Jack, now thinking of himself only as Jill, washed
carefully, feeling for any stubble on her body. She was pleased to find none,
except on her face. She washed her hair, even though it would be covered the
rest of the day. She stepped out of the shower after drying herself off once
again looking for any hair that shouldn't be where it should be. She
shaved-twice, and once she was satisfied with her skin, she began with her
make-up. Jill had plenty of time before she would meet Mary, so she worked
very slowly. Her nails and toes were now dry, so she went to work on her
face. She was pleased with the make-up the Mary Kay lady had sold her. She
laughed when she "did" his/her colors, but now she was sure she had been
right about the hues she was carefully and painstakingly applying to his
face.
Next came the wig. Jill had become rather adept at this she thought. She
scrunched it onto her head, and did the few flips and twirls it needed to
look good in her eyes. She stood up and looked at her face. She was pleased.
She definitely looked younger. Her eyes were wide, her skin smooth, her lips
were too thin, but there was not much--short of collagen shots she could do
about that, and collagen wasn't an option. She smiled at the mirror image of
herself, and headed into the bedroom. She had already laid out her daytime
outfit. She picked up her bra, white and very lacy. She then inserted the
breast forms. These were a luxury. She had splurged on them when she first
started buying her wardrobe. They were heavy, but they made her feel much
more feminine having the right amount of weight on her chest. She then put on
her panty hose and her panties. Jill never got over how wonderful the sheer
hose felt on her hairless legs. She read for years about cross-dressers
luxuriating in this feeling, but it wasn't until she had experienced this for
herself that she could truly empathize with those other girls.
Jill checked her foundations, she debated wearing her girdle, she decided
against it. She was certain that she would be wearing it and the corset
enough over the next few days. Today would be a long day and she opted for
comfort over the couple of inches off of her waist. Jill then picked up the
light gray silk shell and put it on. It felt wonderful against her skin--she
even got goose bumps. She then donned the dark gray skirt. It was knee
length, and has a slight slit on the side. She picked up the tailored jacket
that matched the skirt. She went back to the full-length mirror and adjusted
the skirt and the jacket. She was very excited about how she looked. She
padded back to the bedroom, and slipped into the 2" gray suede heels. She
felt wonderful. She then added silver clip on earrings, a silver bracelet, a
silver watch and two silver rings. She once again headed back to the mirror.
She was very excited, but the panty hose and her careful "tuck job" kept
anyone from noticing how excited she was. All that was left was a spritz of
perfume. She grabbed the Ysatsis and sprayed herself in all the appropriate
places.
Jill picked up the matching purse, dropped in her lipstick and the other
feminine essentials, she added her room key and her wallet, then snapped the
purse shut. She headed for the door, but stopped. She needed to make one last
inspection. She was as good as she was going to get. She turned, took a deep
breath, and walked out the door. She walked the hundred or so feet to the
concierge lounge, hesitated at the door, mustered up her courage, and walked
into the lounge.
The only person in the lounge was the lady who ran the facility. She was
watching television, and turned to see who entered. She smiled, looked a
little surprised, and then smiled again. She walked over to Jill, and asked
her to please sign the guest book. Jill signed J. Fitzgerald with a flourish.
In a moment of craziness, she put a heart symbol over the "i". She smiled,
and informed the lady that she was expecting a guest. The female concierge
nodded. Jill thanked her and walked over to get a cup of coffee. Jill took
her coffee, a paper, and sat at one of the tables to wait for Mary. A few
minutes later as Jill finished reading the sports section, Mary walked into
the lounge.
Jill did an instant analysis of Mary's look. She noted her hair--very nice,
dark brown, maybe just a little too long for her tastes, but nice. Her make
up--again very nice. She had a good daytime look. Her dress--Jill thought the
dress, while a nice red was too tight and too short. But she quickly put it
out of her head. Her shoes--Jill always checked the shoes--were 3" and black.
Jill knew that this didn't work too well, but she didn't care, she was very
glad to see Mary. All in all, Mary could walk down any street and blend into
the crowd with no problem at all. Jill wasn't sure if Mary would recognize
her dressed. So she stood up and waved--in her most feminine manner to her
new friend. Mary smiled when she saw Jill. Jill gave her a welcoming smiled
back. Mary grabbed a cup of coffee and sat with Jill. The concierge lady went
back to the desk at the entrance. Jill noticed this, and quietly, but
laughingly told Mary. She said that the concierge got a better look at them
from this angle. Both girls laughed.
Mary took out the itinerary from her notebook. Jill was impressed. Mary was
planning on taking notes. Jill had a pen in her purse, and figured that there
would be notepaper at the table in the sessions. Mary had the day very well
planned. They covered what they needed to go over in a few minutes, and then
their discussion changed. Mary asked Jill what she thought of "the group".
Jill honestly told her that she was thrilled to have met all of them. She
explained how her traveling partner had to cancel at the last moment. She
said that while the four of them were extremely different, they were fun. She
was especially glad that Mary was a "newbie" like herself, so she'd have
someone to go to the sessions with her. They chatted about the conference,
why Jill was attending, and why Mary was as well. Finally, Mary looked at her
watch, and said, "Time to go downstairs. The first session begins in ten
minutes."
The girls put their coffee cups on the tray near the door, and both said
good-bye to the concierge. They got on the elevator, and Mary bet Jill a
drink that they would make at least four stops on the 20 or so floors that
had to travel. Jill took the bet, and won. They made five stops. Every stop
had businessmen getting on and politely nodding. Jill expected Mary to pass
well, but amazingly enough nobody looked at Jill twice! This was great. The
girls exited the elevator on the second floor and wound around some hallways
to the registration table. They signed in and were directed to the first
session--skin care and makeup.
The session room was fairly small. It had tables set up, and in the front was
a chair with a mirror and a whole counter full of makeup. About 20 "women"
attended the session. A very attractive woman walked to the front of the room
and introduced herself and welcomed everyone to the first session of the
week. She went over some housekeeping points, and then introduced the first
speaker--more appropriately the first demonstrator. What followed was three
fascinating hours of makeovers. Jill and Mary were transfixed. They watched
some very ordinary "women" from the audience go up and sit in the chair in
the front of the room. When they got up to walk back to their seat, they were
exponentially better looking. Mary wrote furiously, while Jill never felt
more alert as she watched almost without blinking. She was afraid to look
away for fear she might miss something. Suddenly it was noon. Jill couldn't
believe it. She never had three hours pass so quickly. The young man who was
doing the makeovers thanked everyone for attending. He said that he would be
available for private sessions on Friday and Saturday afternoons. There was a
signup sheet on the front table for each day. He explained the costs, and
while not cheap, Jill was ready to race to the front. She absolutely had to
have this young man "do" her on Friday and Saturday.
The session ended, and Mary and Jill walked to the front of the room. Jill
put her name down for 5:00 on Friday and Saturday. Mary said she'd love to do
it, but it was too expensive for her. Jill thought about it for a second, and
said, "my treat. I can afford it and what the hell. Pick a day!" Mary said
no, she couldn't but she didn't mean it. She protested once more, and then
hugged Jill, said thanks, and signed up for 4:00 on Friday.
They chatted briefly with a few of the other girls, and then decided they had
better get moving, they had a luncheon meeting with Reggie at 12:30 in the
main dining room. They filed out of the meeting room and headed to the wide
staircase that led down to the lobby. Jill and Mary blended in with the
twenty or so other "women" who headed that way. They made quite a scene as
they descended the stairway. Heads were turning all over the lobby. Jill
smiled as she thought about safety in numbers.
Reggie was sitting in the lobby with Rae. They rose together and walked over
to meet Jill and Mary. Reggie and Rae gushed over Jill and Mary. They were
all hugs and smiles, and then the four of them headed to the dining room. The
hostess seated them without so much as a raised eyebrow. She seemed so world
weary that Jill thought nothing could get her excited. Jill thoroughly
enjoyed herself at lunch. Mary gushed about the makeover session, and how she
and Jill had signed up for tomorrow. Reggie said that Joan had rolled in at
dawn. She must have had a good time 'cause she was smiling in her sleep. Rae,
who was obviously impressed with the quality of the clothes that Jill was
wearing, invited her to go shopping with her this afternoon. Jill declined.
She said she really wanted to attend the afternoon sessions. Actually she had
seen the momentary look of disappointment on Mary's face. The rest of lunch
was talk of dinner-- where should they go? They decided they wouldn't let
Joan pick the place, and they decided to meet in the concierge lounge at 7:30
to make their plans.
The afternoon sessions were very interesting as well. The psychologist was
wonderful. The lady from the wig company did a marvelous job and Jill and
Mary both learned a great deal--especially from the psychologist. Jill talked
to him at length after the meeting. At five o'clock the meetings were over.
Jill told Mary she was going to work out, and make some telephone calls for
work. Mary said that was great with her, she needed to get out of her corset.
Jill laughed and said she was really glad that she didn't wear hers--she was
saving it for tonight.
Jill rode up the elevator with an elderly gentleman who stared at her breasts
the entire ride. Jill couldn't believe it. This guy was looking at her like
she was a real woman. It was wonderful. Jill walked to her room, kicked off
her shoes--which felt good, and made six quick telephone calls that were work
related. She called her daughters, or more aptly, left voice mails with both
of her daughters. Then she stripped off her clothes. She carefully hung up
the suit. She put the nylons and underwear in the dirty clothes bag. She went
into the bathroom and removed her makeup and her fingernail polish.
Ten minutes later she was Jack again. He was pumping on a Stairmaster
listening to ZZ Tops Greatest Hits, and semi-watching the news. He finished
his hour on the "stairs to nowhere" as he called them, and was heading over
to do some sit-ups on the board in the corner. On his way over a woman at the
bench press area asked if he would spot her for her last reps. Jack said
sure, he'd be glad to do it. The woman on the bench had a very nice build.
She looked to be about forty. She had short brown hair, brown eyes that
seemed to be smiling through the strain of her workout. Jack checked out her
body, and was impressed with how fit she appeared to be. She looked to be
relatively tall, with great looking legs. What really drew his attention were
her arms. She looked to be a body builder with the biceps that she had. Jack
knew he would be able to do the number of reps she did with the amount of
weight she was lifting, but it would be a strain to do it. The woman did her
fifteen reps and didn't need Jack's help. She thanked him and he said no
problem. They each wished each other a nice day and went back to their
workouts.
Jack hurried back to his room. He knew he had just enough time to get ready
for dinner with the girls. He shed his work out clothes, checked his voice
mail while he cooled down, and then took a quick shower. He once again
checked himself for any unwanted hair. He was glad that he found none--except
for his face. He dried himself off while half listening to the news in the
other room. Nothing of note he thought as he shaved his face a second time.
Jack walked into the bedroom and began laying out his clothes for dinner. He
was glad that he had planned each outfit carefully before he left for the
conference. He didn't want to have to be making decisions--he just wanted to
turn back into Jill.
He donned the red panties--after carefully tucking himself "up and under". He
checked his profile in the mirror--no bulge. He then picked up the red custom
made bustier. He smiled at the sexiness of it. He placed it around his waist
and snapped it into place. Jill, Jack was now gone, slid the sheer nude
stockings up her legs. She just loved how nylons felt on her smooth legs. The
red bra was next; she expertly put it on and inserted the breast forms. Jill
checked and double checked herself in the mirror, decided she was okay, and
went into the bathroom to apply her makeup. Twenty minutes later she emerged
from the bathroom fully made up. She even decided to go a little crazy and
switched contact lenses. Instead of her usual blue eyes, she now had green.
The wig was prefect, at least in her mind. She picked up the red cocktail
dress, held it against her body. She really liked this dress. Jill unzipped
the back and stepped into it. It hugged her every curve. It came to slightly
above her knees, had long sleeves, and a scooped neckline that showed off her
artificial cleavage. There was a slit up the back of the dress that allowed
her to walk with some ease. Jill accented the dress with a red and gold
choker; it seemed that every outfit she owned came with a choker. She had two
bracelets, a watch and two rings--all gold to finish her accessorizing. She
walked back to the closet and slipped on the three inch red pumps. Jill was
totally pleased with her look. She smiled at her reflection and patted the
dress down along her slim hips. She went to the bathroom and once again
spritzed herself with the Yatsis. She felt ready. She checked herself over
for the fiftieth time, decided this was as good as it would get. She picked
up her purse and headed for the door. Jill didn't see anyone in the hallway
or the elevator as she rode down to the lobby.
She exited the elevator and strode boldly across the lobby and into the bar.
Regina and Mary were already seated and each had a glass of wine. Jill sat
with them and ordered a Pinot Grigio. Mary was gushing about the day and how
it was only Thursday. They had two and a half days left. Regina said that
Joan and Rae would be down shortly. The girls had decided on a nice
restaurant that was only a block from the hotel. It was on a list provided by
the conference staff. This restaurant was anticipating a large contingent of
ladies, and there was sure to be no problem. Regina had made reservations for
the five of them. Jill thanked Regina for taking care of the dinner. Soon
enough Joan and Rae entered the hotel bar. Rae was absolutely elegant. She
oozed class and charm. Joan on the other hand had opted for the cheap whore
look. She didn't care. She was out for a good time and from what Jill had
heard, she was rarely disappointed.
The five of them had one more drink and then walked to the restaurant. It was
crowded. The place was filled with conference attendees. Jill's brain was
going into overload. She was trying to do an instant assessment on every
"woman" in the place. She was trying to determine if she looked better or
worse than everyone she saw. The maitre 'd seated them, and Rae leaned over
and said, "honey you look better than everyone we walked by, but you are only
the third best looking woman at this table!" She laughed and so did Jill.
Jill also knew that Rae was right. Rae was absolutely stunning and Mary was
so cute. Regina looked good while Joan looked trashy. Jill looked very good;
her main drawback was her height. She was elegantly dressed, and dressed
appropriately for her age. She said thanks to Rae for the compliment. Dinner
was tasty and the conversation was a riot. Joan had them laughing at her
escapades from the night before. She had major plans for tonight as well. She
invited the girls to come with her, but once she described where she was
going she scared them, and none of them had the courage to go with her.
Rae announced that she had plans as well. She had made arrangements to meet a
"date" at the bar of the restaurant. All the girls oohed and aahed as Rae
told them it was a professional football player, and he had a desire to date
very attractive "women". She winked as she said "women". The girls discussed
Friday, Jill and Mary had made plans to attend the morning sessions together.
Joan and Rae were going to sleep late again. Mary asked if Jill was going to
the meetings again tomorrow. Jill said yes, she would be attending the
morning sessions for sure, but she didn't think she would be attending the
afternoon meetings. She needed to do some work, workout and the most
important thing was she needed to be on time for her makeover. They continued
talking and comparing notes until nine-thirty. Rae said her date had just
walked in, and was heading towards the bar. The other four girls couldn't
move their heads around fast enough. Jill audibly gasped. She recognized him
as a very famous running back. Rae stood, and said; "see you girls tomorrow
night--maybe." She smiled broadly, and headed to meet her date. He hugged her
and kissed her when she approached him. They talked quietly for a minute and
left.
"Well there goes one lucky guy," said Joan. Mary asked which "guy" she meant
and they all laughed. After they finished their coffees they paid the tab and
headed back to the hotel. All four headed to the bar. If it was crowded last
night, it was mobbed tonight. They wedged themselves into a corner of the
bar, and found a waitress and ordered some drinks. Regina picked up the tab
for these drinks since Jill was gracious enough to buy the night before. The
hotel was smart enough to have a DJ tonight, and he started right as the
girls walked into the bar. There was no shortage of dancers. Folks just
wandered out and danced. No one seemed to be interested in being with a
partner. They just went out onto the dance floor and did their own thing.
There were "ladies of all shapes, size and ages. There were even some "guys"
out there who were dancing. Jill was intrigued as she watched them. They did
seem more inhibited, more like guys. Too bad thought Jill, they probably were
less inhibited when they were dressed like the women they were.
One of the "guys' came over and asked Mary to dance. She said yes, and the
girls never saw her again that evening. At eleven-thirty Joan said good-bye.
She asked one more time if Jill or Regina would be interested in coming with
her, they both said no, and almost in unison told her to be careful. Regina
and Jill talked for about another hour. Finally, they decided to call it a
night. As they walked out of the bar, Jill noticed one of the "guys", and
thought he looked a slightly familiar. She couldn't place him, so she kept
walking. She rode up the elevator with Regina and wished her a good night as
Reggie got off on her floor. Jill went to her room, removed her makeup and
got ready for bed. She took put on a pair of green baby-doll pajamas, and
crawled into bed. She thought about Mary, and dancing with one of the guys
here at the conference, she smiled as she thought of being held in someone's
arms. She dreamt of looking up at her own prince charming.
Friday morning dawned cloudy, but Jill's disposition was anything but cloudy.
She was euphoric; the conference was turning out to be great fun. She was
learning about why she did this, what colors looked good on her, how to
better apply make-up and she had made some good friends. Jill showered and
shaved. She checked her whole body for stray hair, and found one or two that
were quickly shaved off. She dried her hair, applied her makeup, being
careful to utilize two of the tricks she had learned the day before. She then
went into the bedroom and while watching the Today Show got dressed. She put
on her panties, her pantyhose (a garter belt and stockings tonight she
thought), and then went to the closet and selected the pink suit. The skirt
was knee length with a slit up the back, the top was a pink satin shell, and
the jacket was wonderful. Jill slid the jacket on and loved the feel of the
satin lining against her bare arms. She stepped into the two and half-inch
pink heels. Finally she picked up a pin, two rings and a pearl necklace.
Properly accessorized Jill spritzed some perfume on, grabbed her purse and
headed down the hall to the concierge lounge. Jill met Mary on the concierge
level for a light breakfast and they headed down to the meeting rooms. They
were entering a session on the psychology of cross-dressing when Jill noticed
that the room next door was the same class except it was for female to male
cross-dressers. They intrigued her. She thought it would be very interesting
to meet some of them, there appeared to be about twenty-five in the session.
Just like the meeting Jill was going into she noticed they were all ages and
all sizes. The session lasted all morning. The mid-morning break did not
correspond to the female to male break, so Jill put seeing them out of her
mind. Jill and Mary met Regina for lunch. Rae had called and said she was in
love and would not be back until who knew when. Joan was just missing in
action. Jill expressed concerns for Joan, but Regina said don't worry, she'll
show up; this happens at every conference. As they finished lunch, Jill said
she had to skip the afternoon meetings. She had to check in at work, get in
her workout and then get to her makeover appointment. They agreed to meet in
the ballroom at seven o'clock. The agenda for the evening was cocktails at
seven, dinner at eight, entertainment at nine, and dancing from ten to
midnight. Mary headed back to the meetings; Regina said she was going
shopping and then take a nap. Jill wished them well and headed up to her
room.
Jill took off her skirt and blouse, and then carefully removed her hose and
underwear. She put on her work out shorts and tee shirt--they were decidedly
male--and sat at the hotel room desk. She checked her voice mail first. She
called back everyone who had left a message. She didn't reach too many folks
since it was Friday afternoon. She left voice mails for each of them saying
she (or he) would be back in the office on Monday. Jack looked at his painted
toenails as he said that and sighed wistfully. He would be Jack on Monday for
sure; there was no way out of that. After finishing the twelfth telephone
call, Jack checked his emails on his PC. There were fourteen messages, but
only four needed his attention. He finished at two-thirty. He put on a pair
of sweat sox and his shoes, and headed back down to the workout room in the
lower level of the hotel.
Jill entered the room and was surprised to see that the room was crowded at
this time of day. The machine she wanted to use was open so she hopped up
onto the Stairmaster. She turned on her headphones and began listening to
George Thurogood and the Destroyers. The music would keep her moving at a
fast pace. She set the machine and started climbing to nowhere; she looked
around for the first time and was surprised to see that the room had about
ten guys lifting weights, but they weren't guys. They were the "guys" from
last night and the same "guys" from the meeting this morning. Jill couldn't
help herself she was blatantly gawking. She was astounded at the physiques on
some of them. Jill did an evaluation on everyone in the room. She was
generally impressed. On the whole they were very fit, the only thing that she
noticed was that they were generally shorter than most guys were. This made
Jill a little sad; she was too tall for all of them. She stopped gawking
after a while and got into her workout. She pushed the machine to the next
level and really worked up a sweat. She was about ten minutes from finishing
when she noticed that the room was emptying out.
There were only two guys left when the door opened and the woman from
Thursday entered the room. Jill somehow remembered her. She immediately
started talking to the other "guys" in the room. Damn, Jill thought, she's
here for the conference. Without knowing it, Jill smiled. The woman looked
over to the StairMachine at that very moment and smiled back. Jill mouthed
"hello", and kept pumping the machine. The woman waved back and started on
her exercises.
After one hour, the StairMachine blessedly stopped. Jill got off the machine
and stretched out so she wouldn't get leg cramps later that night. She was
dripping wet as she walked by the weight lifters. The woman sat up and asked
if Jill would mind spotting her while she did her bench presses. Jill said
she would be happy to, and positioned herself by the weights. Once again Jill
wasn't needed. The woman sat up and thanked Jill. As Jill was about to say no
problem, the woman added, "Are you here for the conference?" Jill almost said
"which conference?" but she said, yes she was. Jill said, "then I assume you
are too?" She said yes, she held her hand out and said, "My name is Paula,
although if you see me later tonight, I will probably introduce myself to you
as Paul. What's your name?" Jill said, my name is Jack, but like you I have a
nom de plum as well, tonight I will be Jill." Jill added, "Will you be at the
dinner?" Paula said yes, she was going to be sitting with some new friends,
but she would try and look for Jill after the dinner. Jill said that would be
great; she then said she didn't want to be rude, but she had to get
going--she needed a lot of time to get ready for tonight! Paula laughed and
said she understood only too well, she used to have to do that! They both
laughed. Paul asked Jill to save a dance for her. Jill blushed, but she
assured Paula she would. Jill turned, and headed up to her room, while Paula
went back to her workout.
Jill looked at her watch. She would have just enough time to cool down and
take her shower before the makeover crew arrived at her room. She was very
glad she paid extra to have them come to her room. She didn't want to go
downstairs and then get back to her room half done. She wanted the calmness
of her room to get ready for the evening. As she exited the elevator and
walked to her room she smiled and thought "Paul was tall".
It was 3:45 when Jill got to her room. She had stopped at the concierge
lounge and grabbed a couple of diet cokes. She stripped off her sweat clothes
and donned the hotel's terry cloth robe; she didn't want to ruin her satin
robe. She poured a coke for herself and awaited Mary and the makeover crew.
Mary arrived within a minute of Jill getting back to her room. She was
wearing a pink and white jogging suit with darling matching shoes. Jamie let
her in and gave her the other coke. Mary was excited and she was babbling
about the afternoon session. Jill nodded, but really didn't pay too much
attention. Right at four o'clock there was a knock on the door. Jill opened
the door to find three women ready to "gussy them up". She let them into her
room, and explained that she had two appointments; the first was for Mary and
then her. That was all the ladies needed to know. They told Jill to take her
shower while they began to lay out all of their "stuff". They turned to Mary
and asked her to disrobe and put on the smock they had in their bag. Jill
disappeared into the shower, and the trio started on Mary.
Jill headed into the bathroom, and the makeover trio moved toward Mary. Jill
took her time in the shower, and when she emerged from the steaming room, she
headed out to the living room to find the three women hovering around Mary.
They were oohing and aahing. They stepped back to admire their work as Jill
entered the room. They had worked magic. Mary was absolutely gorgeous, and
she could feel it. She was beaming. She saw Jill and her smile grew even
larger.
The girls said they were finished, and that Mary could head back to her room
to get dressed. She tried to tip them, but they refused. The one who was the
leader said that Jill had already taken care of them-very well. Mary thanked
them and then hugged Jill tightly. She thanked her profusely, and said she
would see her at the party.
Once Mary left Jill turned to the woman, and they said Jill should disrobe
and lay down on the bed. She would get a massage before they did her makeup.
Jill laid down on her stomach and suddenly felt six hands on her body. She
never felt so good. She hoped they would never stop. But eventually they did,
and she had to get up, put her robe back on, and go into the living room for
her makeover.
The women were extremely professional. The leader started on her face, one
took her hand for the manicure, and the third started on her feet for her
pedicure. They worked without speaking, and they worked wonders. An hour
later they announced they were done. Jill now had beautifully painted
toenails and fingernails. They were bright red and she loved them. She had
her makeup professionally done and it was flawless. She couldn't believe how
great her eyes were. They were larger, softer and had a dreamy wet look that
made her look sexy and sultry. The woman had also fixed her wig. They
expertly placed it on her head and affixed it to her own hair. Her hair
looked better than ever. She tipped them fifty dollars apiece. They each
protested briefly, and then gratefully accepted the tip. Jill reminded them
she had an appointment for the same time tomorrow. The woman brightened at
the realization that they would be back. They reassured her that they would
be on time, and left Jill to finish dressing.
Jill decided she needed a glass of wine before she started to get dressed. It
was a few minutes after six, and the dinner didn't start until seven. There
would be cocktails until about eight, and then dinner. Jill didn't want to be
the first one there. She opened the bottle of pinot grigio that she had
chilled, and sat down to get her wits about her. She couldn't believe how
excited she felt. She knew she looked better than ever before. She was
excited about the idea of going down to dinner as Jill. She decided she would
be going to more of these events. This weekend had already been a success.
At six-thirty Jill got up and started to get dressed. She put on her skimpy
bikini cut black satin panties. Next she added the black garter belt, she
always smiled when she donned this item, she thought of the movie Bull
Durham, and thought, "the rose goes in the front big guy." She opened the
package of black sheer nylons. She carefully ran one up her leg, and then the
other leg. She loved the soft sensuous feel of the nylons as they slid up her
hairless legs. She admired them once she had them adjusted on her legs. She
then went and took the black dress out of her closet. It was the most daring
thing that she would ever wear. It had a high collar, and had thin straps
coming down the back. It was almost backless. The front was cut out and would
show cleavage. Jamie inserted the breast forms into the built in cups. She
stepped into the dress, pulled it up, and almost fainted. She was so turned
on she couldn't stand it. She zipped up the side of the dress, and padded
over to the mirror. She adjusted the dress and simply gazed at the reflection
in the mirror. She couldn't believe it was her looking back.
Jill poured herself another glass of wine, and took a long drink. She went
back into the bedroom and put on the black three inch matching black shoes.
Jill then added her earrings, chain, bracelet and watch, all in silver. She
took two rings, one for each hand and put them on as well. She finished by
putting on her perfume. She went back to the mirror, and said, "Well Ms.
Fitzgerald, you look ravishing this evening. How many hearts are you going to
break tonight?" Jill started to smile and to raise her glass of wined to the
reflection, when she thought about what she had just said. She was really
thinking about herself as a "her". What trouble would that be getting her
into. She wondered what would happen if someone, some guy, really asked her
to dance.or more. What would she do? She didn't know. She answered herself
with an honest answer that scared her-it would depend on what he looked like!
Frightened or not, she decided it was not time to head to the party. She
grabbed her purse, put her essentials into the small black clutch bag and
went down to the ballroom where she was surprised to see was already crowded.
Well, she thought, free drinks will always draw a crowd.
Regina found Jill. Regina hugged Jill, and gushed over how lovely she looked.
Jill returned the compliment, and asked where the girls were sitting. She
added that she hoped they saved a place for her. Regina said not to worry;
Mary insisted that Jill sit next to her. Regina said that Mary hadn't even
touched the ground since she had her make over. Regina thanked Jill for
making this event such a pleasure for Mary. Jill said it was nothing, she was
happy to help, and besides the four of them had been so nice to her it was
the least she could do.
Mary came up; she was a vision of loveliness. She was wearing a red dress
that made every curve, real or not, look accentuated. Jill then noticed
Regina's dress. She was wearing a black dress as well. Jill decided that
Regina looked very good, but she rated herself as looking better. Mary led
Jill to their table. Jill almost audibly gasped when she saw Joan. Once again
Joan had opted for the cheap hooker look. She was wearing an off the shoulder
blouse with a micro mini skirt and fishnet stockings. The whole look was
highlighted by too much makeup. Joan was talking to another cd who was
obviously very interested in what Joan was saying. Jill looked around for
Rae. She asked Regina if Rae was coming, and Regina said, "Rae called around
three o'clock this afternoon. She said she was on her way to Atlantic City
with her date. She would see us tomorrow night."
Wow, thought Jill. Rae must be having a great time. Regina, Mary and Jill sat
down, and this caused Joan to see them. She flamboyantly waved to each of
them and blew them kisses. She introduced her friend, Louise, to them. She
explained that met Louise the night before at a local club and they were both
very glad that Rae was not coming back to the room tonight. The five were
joined by three more ladies who Jill was embarrassed to say never learned
their names.
Dinner was pleasant enough. Jill, Regina and Mary talked, the other three
ladies talked, and Jill seemed to think that Joan and Louise were fondly each
other under the table. While the soup, salad, chicken, dessert and coffee
made its way to the table, Jill tried to discretely find Paula/Paul. She
found two tables of female to male cross dressers, but was unable to detect
her acquaintance from the workout room. Finally the speeches were over, the
dinner was over, and the bar was reopened. The dj had set up in the corner
and the drinking and dancing part of the evening had started. Jill was about
to ask if anyone wanted a drink when Joan announced she and Louise announced
that they were leaving the party to start their own.
Everyone at the table looked a little uncomfortable, but smiled, and wished
them well. Jill took six drink orders, and left for the bar. When she
returned she found someone sitting her chair talking to Mary. It was a real
guy asking her to dance. Mary was saying no, but Regina was urging her to do
it. Jill cast the deciding vote, and Mary found herself dancing. Regina and
Jill spent the next forty-five minutes watching the dance floor. Mary didn't
return. She was either dancing or talking to her new conquest. She looked to
be having a great time. Jill wistfully thought it must be wonderful to be
only 5'8' and under forty, and look to be under thirty. She had started her
third glass of wine and was beginning to get a little melancholy. Her mood
wasn't helped when another girl asked Regina to dance. Jill thought this must
be how girls feel when they wind up being wallflowers. She smiled in spite of
herself. She took another drink of her wine and wondered what had happened to
Paul.
As she wondered she felt a soft hand with an even softer touch on her bare
shoulder. She turned to look up into the beautiful brown eyes of a tall man
wearing a great tuxedo. A soft voice said, "Did you save me a dance?"
"Paul, is it you? I can't believe it."
"Jill, I could certainly say the same thing. I spent almost an hour trying to
find you. Can we dance?"
Jill stood up and moved as if in a trance. Paul was so handsome. He was
wearing a wonderful tuxedo and black patent leather shoes. His hair was short
and slicked down to look like a guy's. He didn't appear to be wearing any
makeup, but his face looked almost rugged. Jill was smitten. Paul lead Jill
out onto the dance floor, then turned to face her. The dj was playing
Searching for a girl like you, by Foreigner. Jill momentarily forgot what to
do with her hands. Paul took them and started dancing. Jill, as Jack, was a
terrible dancer, but she found herself following Paul very easily. Paul spoke
first, "Jill, you are beautiful. I can't believe you are the same person I
saw leaving the gym today. I have been, like the song says, searching for you
all evening." Jill smiled and thanked him. She said, "I can say the same
thing. You don't look anything like the person I saw today in the pink
workout suit."
They each smiled, and Jill felt Paul pull her slightly closer. Despite the
fact that Jill was a little taller than Paul she felt wonderful in his arms.
She asked how tall he was, Paul said he was 6'0" in his stocking feet. Jill
said he seemed taller. Paul said he bought lifts for his shoes that afternoon
after meeting Jill. Jill blushed, and said that was a waste of money. Paul
said he didn't think so at the time, but now he was sure it wasn't, it was
money well spent to look her in the eyes.
The song ended, and they just stood there for a moment, each looking into the
eyes of the other. Paul broke the silence by asking Jill if she would like a
drink. Jill nodded her acceptance and was embarrassed by acting like a
schoolgirl. Paul smiled at her and reached out to take her hand. Jill
instinctively took Paul's hand, and he led her to a small table in the corner
of the ballroom. Paul gallantly took the chair out for Jill, and asked her
what she would like to drink. Jill said a white wine would be nice. Paul
quickly headed over to the bar, and was back in a few seconds. Jill used
those few seconds to compose herself. She noticed that Paul almost sprinted
to the bar. He was as nervous as she was. She smiled as she pondered the
thoughts that just ran through her head. She thought of herself as "her" and
she thought of the woman in the tuxedo at the bar as a "he". It seemed
absolutely normal, and she was very glad it was.
Paul set the glass of wine in front of Jill, and took the seat opposite her.
He raised his glass, and said, "Here's to my favorite bench press spotter!"
Jill clinked her glass with Paul's, and drank. She then proposed her own
toast, "thank you for my first dance." She clinked her glass with Paul's
again. Paul never took his eyes off of Jill as he drank. "If I was fortunate
enough to have your first dance, maybe I can establish a monopoly!"
Jill smiled coyly, and said, "you never know." They each drank once more and
Jill sensed an air of relaxation overtake her, and she sensed the same with
Paul. She was about to ask him why he was at this function, but he beat her
to the question. He asked where she was from and why she was there. Jill said
that her story was like every other cross dresser. She briefly reiterated her
story and finished by saying that she was from the Chicago area. Paul looked
surprised. He said that he was from the Chicago area as well. He said he was
from the north shore, and now lived downtown. Jill said she was raised on the
south side, in the city, and now lived in the western suburbs. Jill then
asked Paul why he was at the conference.
Jill said she had a slightly different twist to her story. She was a tomboy
as a kid. She was always tall, and was a good athlete. But she never wanted
to be a boy; she just wanted to be shorter. She excelled in basketball and
volleyball in high school, and won a scholarship to Michigan State. There she
met her husband. He was a basketball player at MSU as well. They married
right out of college, just like Jill. They had three children, just like
Jill. Her husband was an extremely successful commercial real estate broker,
and Paul had spent six years getting her law degree. She now had a successful
law practice in the city. She said her career and her life were idyllic.
Then four years ago she found a lump in her left breast. She went to the
doctor immediately, but to no avail. The cancer had infected both breasts.
She had a radical mastectomy on both breasts. The doctors said they had
gotten all the cancer, and her prognosis for a full recovery was excellent.
That was the good news. The bad news was that for two years she was
miserable. She felt ugly. She felt disfigured. She was a bad mother and a
worse wife. During this time her husband completely distanced himself from
her, which certainly didn't help her recovery. He took a mistress, and then
two years ago filed for divorce. Now she truly was devastated. Her children,
two boys and a girl, just the opposite of Jill, were out of the house. She
was living alone and feeling sorry for herself with every breath she took.
She sold the house, and moved downtown. Then one night on her way home she
went into a lesbian bar. She had