The Dance                    by: Jamie Lynne Williams                Jlw325@aol.com

 

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 worn her hair short for years, so that night she combed it like a guy; put on a suit and tie, and went in. She found women coming on to her almost right away. She was still fit and attractive, she just FELT ugly. She fended off all of their advances. She was too afraid to try anything. She went home and cried. She convinced herself to go back. She did, and this time she took a woman home with her. She didn’t like it.

Now she was facing a quandary. She found she liked to dress like a guy, but she didn’t especially like having sex with women. Since she was a woman of the new millennium she found some Internet sites and joined a group of women in Chicago who were into dressing as men.

She finished by saying that she didn’t need to do it all the time, but When she was dressed as Paul she didn’t feel sorry for herself. The weight training made her feel stronger and more in control. So she dressed as a guy two or three weekends a month, and it was good therapy for her. Two of the people in the club were coming to this conference, and she thought it would be good to meet more folks, and to learn a little about why other people did this.

Jill sat there in rapt attention. Paul suddenly realized that she had gone on for quite a while. She looked flustered, and said, "Can I get you another drink?" Jill said, "in a minute, but the dj is playing another slow song, would you ask me to dance again?" Paul smiled and said of course. I would love to dance with you again.

They walked to the dance floor hand in hand, and Paul took Jill into his arms and Jill danced her second dance as Jill to the strains of Turn the Page by Bob Seger. As Jill danced with Paul she felt like she was turning a page. Instinctively she put her head on his shoulder. Paul tightened his grip around her waist. Then she put here arms around his neck. She never felt so wonderful in her live. She never felt so much like Jill-ever.

Jill’s move made Paul horny for the first time in four years. He wanted to pick this woman up, take her to his room and make love to her. He wanted to have an erection!

The song ended way too soon. They didn’t break their embrace. They stood on the dance floor desperately hoping for another slow song. The dj must have seen them and fulfilled their mutual wish. The next song was a slow one. Jill didn’t know the name or the artist, but she didn’t care. It enabled them to once again justify their embrace on the dance floor. Jill never thought that she didn’t like this song. She just moved with Paul. She sighed. Paul heard her, and took his right hand, cupped her chin, and gently raised her head. Jill looked into his beautiful brown eyes as he stared into her blue eyes. It was inevitable. Paul leaned forward, and kissed her. They both felt the electricity. Paul opened his mouth and tentatively pushed his tongue forward. Jill opened her mouth to accept it. They kissed passionately for the rest of the song. Finally, they broke apart. They looked into each other’s eyes hungrily. Paul took Jill’s hand and led her back to their table. Jill squeezed it as she walked closed to him. They sat back at the table and in unison said, "Thanks for the dance." This broke the sexual tension and they were able to laugh. They talked and danced the rest of the evening. They learned about each other’s children. Paul learned the Jill was widowed. The hours passed like moments. The dj announced the last dance. Paul and Jill looked around and found not only the dance floor empty, but the ballroom was nearly deserted as well. They were so caught up in each other that they forgot all about their surroundings.

Without speaking they rose and went to the dance floor. The dj asked if they had a favorite song. Jill said please play Searching for a girl like you, by Foreigner again, it is our song. Paul took her in his arms and they danced all alone on the dance floor.

When the song ended, they once again lingered in their embrace. Jill finally kissed Paul on the cheek, and said she needed to say goodbye to her friends. Before they left. Paul smiled, and Jill blushed. She had just assumed that they would still be together even though the dance was over. Paul said he would make his goodbyes as well and they could meet back at their table.

The only one of the four girls from Cleveland still there was Mary. She was with someone who appeared to be a genetic male. Mary saw Jill coming over, and walked over to meet her. She was gushing about how handsome Paul was. Jill thanked her and for some reason she felt compelled to downplay the event. Jill asked Mary if she was okay. She said she was, and winked. Jill said she would call Mary around noon Saturday and they could make plans for the dinner Saturday night. Mary agreed, and Jill walked back to a smiling Paul.

Paul suggested that they go somewhere to continue their conversation, and have another drink. Jill said yes, and suggested her room. She said she had a couple of bottles of wine chilling, and they wouldn’t have to try and talk over the noise in the bar downstairs. Paul agreed and they left the dance and walked to the elevator. Their trip took them through the lobby; they couldn’t resist at least looking into the hotel bar. Jill was right. It was mobbed, by not only attendees from the conference, but the curious as well. They looked knowingly at each other, and continued on to the elevator. Jill hit the button for the top floor and Paul said his room was up there as well. It turned out that they had adjacent rooms. Jill laughed and said hopefully they are adjoining. Paul said that would be asking way too much.

The door opened, and they walked to Jill’s room. She went to the bar to get glasses and to give Paul the bottle of wine to open. He was busy checking out the hotel room. He came up behind Jill and said, "Do you believe it, we do have adjoining rooms. If you open your door, I will go to my room and come through it. That will give me a chance to go to the bathroom and freshen up." Jill readily agreed, and said she would do the same. She suggested that Paul open the wine first so they could each have a glass now. He opened the wine, tasted it, nodded his approval, and smiled at Jill while he poured her a glass of the Chablis. Paul took a brief sip, and said he would be right back. Jill opened the adjoining door for Paul, and then made a beeline for the bedroom. She neatened it up the best she could. She was neat as Jill and as Jack so the room looked presentable. She went into the bathroom and took care of herself. Taking special care to make sure that she was fresh for Paul. She brushed her teeth and fixed her makeup. After a careful touchup of her hair she decided she looked presentable. She went into the sitting room in her room to find Paul waiting for her. He smiled, and said he knew that it took women longer. They both laughed. Jill walked over and sat next to him on the couch. She slipped off her shoes, and slid her legs up under her. She leaned back on the couch and took a sip of wine, and asked, "Now Paul how would you ever know such a thing?"

Paul laughed and ignored her question. Paul was looking intently into Jill’s eyes. He took a long drink of the wine, breathed deeply, and said, "Jill, tonight has been wonderful. I truly hope that this is a minimum the start of a friendship. I have spent the last four years avoiding sex. As a woman I have unable to let myself go. Tonight, for the first time in four years I have found myself wanting to make love to someone. Tonight, I would like to be Paul and make love to you, my beautiful Jill. Please don’t think me too forward. If you don’t want to, I can certainly understand. I just want you to know that I have not felt like this since before my operation."

Jill didn’t say anything. She put down her glass of wine, and slid over to Paul. She kissed him, gently at first, then she opened her mouth and their tongues met. Jill leaned into Paul and sighed softly. Paul knew his answer. He moved to take the upper position. He softly kissed Jill’s neck, her eyelids, and her ears. Jill responded by running her hands up and down Paul’s back. Jill marveled at how strong Paul really was. Jill slid further back on the sofa until she was completely supine. Paul was on top of her and they were kissing and groping as best they could through each other’s clothes. Breathlessly, Jill suggested they go to her bedroom. Paul helped her up and they walked a little unsteadily the few feet to her king-size bed. Jill turned and kissed Paul gently once again, and said, "let me help you with that tuxedo sir, it is only in the way." Paul let her undress him. She had everything off of him but a tee shirt. She started to take that off, but he stopped her. Jill realized why, and didn’t go any further. Paul then said it was his turn. There wasn’t much to remove past the dress. Jill said she wanted to leave her nylons, garter belt and bra on for now. They both knew they had emotional baggage they were taking to bed, and the underclothes helped.

They lay together on the bed, both still wanted to make love more than anything, but they needed to get their roles in order here in bed. Paul made the first move. He turned off the light in the bedroom making the room dark. Only the light from the room next door brought any illumination to Jill’s bedroom. He then removed his tee shirt, and asked Jill to take off the rest of her clothes. He said that the beauty and the passion for the rest of the night was reserved for the sense of touch, taste, feel, and for the most important thing of all, their sense of imagination. He asked that Jill truly think of herself as Jill and to think of him as Paul. True gender and identity be damned. Jill couldn’t believe her ears. This was perfect. She wanted to be in this man’s arms, she wanted him to love her.

Jill rolled over and started kissing Paul from his head, to his eyes, and was working her way down to his torso. Paul started to stop her, but she took his hand, sensuously sucked his fingers, and then proceeded to rain kisses all over his chest. She found some very sensitive spots, and lingered there nipping and sucking. Paul again tried to stop her, but she said, "you’ll get your chance lover, right now I want to show my man how much I love him. Lay back and enjoy it." She continued her downward trek on his body. She purposely avoided his most sensitive spot. She worked down one leg, lingered on his foot, sucked his toes; and reveled in Paul’s moaning and squirming. She attacked his other foot, and then worked her way up his other leg. She knew Paul was anticipating her going between his legs at that moment. She didn’t. She quickly popped up and kissed him on his lips, and rolled over on to her back. "Come up here," she said, "I can do a much better job of licking you if you sit up here. Grab on to the headboard, and let me make you feel good."

Paul protested for a moment and then gave in, just as Jill expected. Paul positioned himself above Jill’s mouth and lowered himself down. Jill was true to her word. She grabbed hold of Paul’s hips and had her tongue, her lips her whole mouth loving his most private parts. Paul was wracked with orgasm after orgasm. After twenty minutes Paul couldn’t stand any more pleasure. He raised himself off of Jill to Jill’s protestations that she was only getting started, and collapsed next to her on the bed. Paul was coated in sweat. He had never had so many orgasms in one night and knew he wasn’t anywhere near done. Jill wiped the sweat from his forehead. She had a huge smile on her face. She was so happy to please him. Paul said he needed a moment, but only a moment and he would be ready again. Jill teased him about being a typical guy. With that, Paul reached down and started stroking Jill’s male clitoris. Jill sighed again, and Paul knew what he wanted to do.

He rolled on top of her and let her slide into him. God, she felt good he thought. I have missed this for too long. He looked down at Jill. She was looking up at him, and Paul had never seen a look like that before, not in the fifty years he had been on the planet. Jill was totally in love with him. He could see it in her face. He could feel it in how her hands caressed his body. Paul wanted to return that love. He could feel it emanating from the joining of their bodies.

Jill pulled a pillow under her butt and Paul found that they fit better. She said, "Paul make love to me. Make me your woman. I want to feel you in me. I want to feel you explode into me. Oh, god Paul, I love you, please, please make love to me." As Jill talked to Paul as if he was really a man, he found it a terrific turn on. He started to pump up and down on her. "Jill I want to make love to you. I want to fill you with my seed. Oh, god, baby, you feel so good. I can’t wait to cum inside you!"

Paul and Jill made love for as long as they could. They went slowly, they sped up. They kissed, they caressed, and talked dirty to each other, finally Jill could stand it no more. She was going to come. She raked her nails down Paul’s back and clenched her legs around Paul. She screamed, for the first time ever, "Oh Paul, come with me, fill me up, oh Paul this is the best, I need you to come with me now." And he did. They came together each with earth shattering orgasms. Paul fell onto Jill. She held him tight. She wouldn’t let him off of her until her penis slid out of him.

Jill didn’t want him to move. He felt so good on top of her. She had never had anything this good. Suddenly she started to cry. She was embarrassed, but couldn’t stop. Paul looked down on her and asked what was the matter. Jill gave the most feminine answer of her life, "I am so happy." Paul slid off of her, and pulled Jill close. He put his arm around her, and literally kissed away her tears. Jill hugged him, and said, "thanks, that was the greatest. You are amazing." Paul said, "no, I think WE are amazing. This has been the best love making of my life too."

Jill snuggled up next to Paul, and suddenly they were both realized how exhausted they were. Jill, looked at the soft dark outline of her lover, and asked, "You are going to be here in the morning aren’t you? I don’t want to wake up and find you gone. I would be too afraid you were just a dream." Paul promised to be there in the morning. They both fell sound asleep, wrapped blissfully in each other’s arms, without a thought about the realities that daylight would bring.

Jill woke up first. She looked over at Paul, and couldn’t believe how cute he was. She really did think she could love this very special man. She then panicked. She thought that she had look terrible. She quietly slipped out of the bed, and went into the bathroom. Her fears, at least in her mind, were well founded. She quickly shaved, redid her make up, fixed her wig, and brushed her teeth. She also donned her dark blue baby doll pajama top, and slid back into bed. She lay there for a while just trying to memorize Paul’s face, when suddenly he woke up. He instantly tried to cover himself up. Jill saw what he was trying to do, and stopped him by getting up and sitting on him. Paul asked Jill to please let him put his tee shirt on. Jill said no. She loved him just the way he was. "Besides," she said, I like my men to look rugged!" With that she planted a deep kiss on him, and said, "I know what I want for breakfast, I want to give you the best blow job of your life."

Paul protested, "You have already done too much for me. Besides, I already had that last night. If you do it again, I may spontaneously combust!!" Jill laughed and dove beneath the blankets and started to lick Paul again. She could taste the juices that the mingled the night before, and they was a sweet reminder to her of the love they had shared. Paul came at least three times, then pulled Jill up to him. As he did her penis slid into him. Jill started to pump in and out of Paul. She kissed him on the lips. She kissed him on his chest, and then looked into his eyes and began furiously pumping in and out of him. She was consumed with lust. She wanted to come. Paul was right with her. He was pushing up as hard as she was pushing down. He pulled her nightie off; he wanted to kiss her breasts. Neither could even talk. When they came is was as all encompassing as the night before. This time Jill collapsed on top of Paul. He held her tight. There were no words to say. Their bodies, glistening with perspiration, were testament to the love each had made with the other. Jill slid out of Paul. She lay there for a few more minutes, and then rolled off of him. She went to take him into her arms, but he was still Paul, and she was still Jill, he pulled her into his muscular arms; she once again snuggled up as close to him as she could, and knew she wanted to have these arms around her forever.

Paul held Jill while the after shocks of his multiple orgasms washed over him. He felt whole again for the first time in over four years. He was holding a beautiful human being who loved him. He was holding someone who loved him/her for who he/she was. Paul started to cry. For the first time in four years, it was his turn to cry and say it was because he was-so happy. They held each other, each completely happy. They drifted back to sleep.

Jill woke to find herself alone in bed. She rolled over to find Paul walking back into her room. Paul had on a black Gold’s Gym tee shirt and a pair of gray shorts. Jill noticed for the first time how great Paul’s legs were. Paul said, "hey sleepy head, it is a great day here in New York, are you going to sleep all day?" Then he asked if she wanted breakfast. Jill said coffee would be great. Paul said he had already ordered breakfast. It would be up in about twenty minutes. Jill asked Paul if she had time for a shower? Paul said, "If you are going to come out as Jack, yes, if you are coming out as Jill no. Why don’t you just come out neutral? Don’t worry about being Jack or Jill just come out."

Jill went into her bathroom and removed her wig and her make up. She spent ten minutes in the shower wondering what to wear. Finally she decided to just put on the terry cloth robe that was in her room. She left her nail polish and her toe nail polish on, shaved and headed over to Paul’s sitting room where he was just paying the room service bill. Jill walked up to him and kissed him lightly on the lips. Paul returned it by wrapping his arms around Jill and kissing her passionately. Jill poured the coffees while Paul set the plates on the table. He had ordered omelets for both of them. Jill hadn’t planned on eating much, but the aroma of the omelets made her mouth water. She suddenly was extremely hungry.

They talked as they ate. Both found that they were very much at ease with each other. There was no morning after remorse or second thoughts. They genuinely enjoyed each other’s company. Paul regaled Jill with humorous tales from his law practice, and Jill recounted some of her funniest travel stories.

As they finished breakfast Paul asked Jill what she had planned for the day. Jill said she had kept Saturday open. There weren’t any sessions that interested her, and she had planned on doing some sight seeing or some shopping. She asked Paul what his plans were. He said pretty much the same thing. Then he asked Jill if she would like to go window-shopping with him. They could just wander around the city and spend some more time together. It was already 10:30, and Paul said he wanted to work out around 4:00, so they couldn’t do too much. Jill said that would be great with her, but she had an appointment at 5:00 for her make up, so she would like to start her work out at 3:30 at the latest, preferably at 3:00. Then she asked did Paul have gender in mind for this shopping trip? Paul asked Jill if she did. She said she would love to go as Jill, but was afraid to go outside of the conference dressed. Paul replied that her answer made it imperative that she go out as Jill. He said, "You are absolutely passable, tall but passable. Plus every merchant in the area is being inundated with cross dressers. And last, but certainly not least, you will be traveling with your lawyer!" Jill laughed and said, "then how can I go wrong! Give me a couple of minutes and I will be ready to go."

Jill was true to her word. She put on some make up and redid her wig (she was glad she brought two wigs, her formal wig was being worked on even as she was having a great time this afternoon.) She ran into the bedroom and selected two-inch black pumps, tan hose, a black skirt and a white turtle neck sweater. She accented the sweater with some gold chains, grabbed her purse and walked over to Paul’s room. He looked great in gray slacks, black shirt and black sport coat. Jill envied him his penny loafers, but she wasn’t about to wear flats this weekend if she could help it. Paul whistled his appreciation, and took her by the arm to escort her out. As they rode down the elevator they decided to shop for Paul first and then Jill.

Walking through the lobby Jill spotted Mike, the bellman, who had helped her with her luggage on Wednesday working the front door to the hotel. She asked Paul to humor her a minute, she walked over to Mike and asked him some basic New York City directions, explaining that she and her husband were from some remote Midwestern city. Mike was very courteous in explaining how to find the store in question. Jill thanked him profusely, and then asked what the conference in the hotel was all about. He pulled Jill and Paul over to the side and whispered that they picked a bad weekend to stay at this hotel. It was full of fruits that dressed up like women. Jill and Paul feigned surprise and shock. Mike told them it was true. And he was sorry if this ruined their stay. Paul said thanks for letting us know. It will be fine, and it will give us something to tell everyone at the Rotary Club meeting next week. As they walked away giggling, Mike mumbled something about ‘hicks from the sticks’.

Jill felt the cool air on her legs, and the realization that she was on the streets of New York hit her psyche much harder. She momentarily froze in front of the hotel. Paul stopped, and took her by the arm. "Jill, you are a beautiful woman, I am very proud to be with you, now just relax." Paul’s touch seemed to make everything seem better. Jill took a deep breath and started walking down the street with her new boyfriend.

They were true to their word. They did shop for Paul. He bought a pair of shoes, some workout clothes, and three shirts. Then he steered Jill towards an expensive woman’s store. She had never shopped in a real woman’s store before. All of her clothes were purchased at shops that were advertised in cross dresser magazines. Jill could feel her heart pounding as they entered the store. "Paul, I can’t do this. I’ll get us arrested. We can’t do this." She whispered. Paul said that was nonsense, they people would be fine.

Paul seemed to know his way around the store and lead Jill to a section that specialized in taller sizes. Within in minutes Jill was trying on dresses and being fussed over by a sales lady, who if she suspected anything, was not about to let on and jeopardize her sales commission. Two dresses and a peignoir later they left the shop. Paul said they had time for a quick bite before working out. Jill asked if he like sushi. He did, and they laughed about their first excursion out together as they sampled each other’s selections of uncooked fish.

When they exited the sushi bar Jill realized that her feet were starting to bother her. She didn’t want to push it, so she suggested they cab it back to the hotel. Paul readily agreed, and within minutes Mike the bellman was helping them out of their cab. Jill couldn’t resist letting her skirt ride way too high on her thigh as she exited the cab. She looked up to see Mike staring. She smiled at him. It was a smiled that said too bad, this is all you are ever going to see. Mike blushed, assisted them with their bags as far as the hotel lobby. Jill toyed with the idea of having Mike bring her bags up to her room to see if he would remember that it was Jack he first helped, but then thought better of it. She didn’t have time to fool around with him today. Paul tipped him, and they each took their purchases up to what was now their suite of rooms.

Each went to put away their respective purchases. Paul wandered back into Jill’s room. He had a devilish smile on his face. Jill asked what he was thinking. Paul said, "Since we are having so much fun as Paul and Jill, why stop for the hour we are working out? Why don’t you wear my work out clothes, and I’ll wear yours?" Jill smiled and said, "what a great idea. Paul, you are a genius!" Minutes later they got on the elevator Jill in pink spandex, accented by her breast forms. She had a pink sweatband for her hair and she was wearing Paula’s pink and blue Nike’s, and for the first time in her life she would be working out wearing lipstick and makeup. On the other hand, Paul was not wearing makeup. He had his hair combed like a guy, and Paul was wearing a black White Sox shirt and some ragged gray shorts. She had droopy white sweat sox and Jack’s scuffed up Brooks training shoes. They held hands as they rode down the elevator to the workout room. They didn’t let go until they were actually ready to start working out.

One hour and twenty minutes later they were both drenched in sweat but once again holding hands on the elevator. This time on the way back to their rooms. They stopped at the concierge lounge and grabbed a couple of diet colas, and went to the rooms. Jill loved the way Paula’s outfit felt. She hated the idea of going back to wearing "drab" clothes again. She hung up the spandex outfit and carefully placed the other items she wore in the closet to dry. She showered in her room while Paul was in his. Jill had told him in no uncertain terms that he couldn’t see her until six-thirty. She had a five o’clock appointment for her makeover, and then she needed thirty minutes to finish getting dressed. At six-thirty he could come over and they would have a glass of wine before going down stairs for the big gala in the ballroom. Paul smiled, kissed her, and said he was going to take a ninety-minute nap, and then get ready for the event. He said he knew only too well how long this could take. Then he added, that if it was up to him, they could skip the entire event and get room service! Jill kissed him back, and said, "what a typical guy. You better take that nap, ‘cause if I get my way, you’ll need all the rest you can get."

The makeover artists were right on time. Jill was glad that she had started her workout at three o’clock. She needed the extra half hour to cool down despite the cold shower. Jill let them in, noting that they were the same girls as the day before. They were very nice. They were chattier than the day before. They asked Jill how the dance was the night before and what she did today. Jill told them-in broad generalities, skipping the best parts of what she did. The girls delighted in the story, and asked where this "Paul" was now. When Jill told them that he was right next store, they almost fainted. Despite the chatter, they were extremely proficient. Within the hour Jill had newly painted nails, on her toes and fingers, her makeup impeccably done, and her formal wig perfectly fitted on her head. Before the girls left they asked if they could do anything else for Jill. She said no, they had done enough, and then she added, "The rest is up to me!" The girls laughed, and once generously tipped by Jill, left.

Jill now had to finish getting ready by herself. She went to her drawer and selected the baby blue lingerie set she had bought for this dress. She put on her sheer silk stockings and affixed them to the garter belt. She strapped on the three inch barely there baby blue shoes. She went to the closet and took out her ball gown. She loved this dress it was floor length with a slit up the left side that went almost to her hip. It was strapless and backless. She fitted the breast forms into their positions and carefully stepped into the dress. She zipped I up what there was of the back of the dress, adjusted it slightly, and went to the mirror. Wow! She was sure this dress would make Paul horny. Then she thought how interesting, she was already thinking about dressing for Paul. Hmmm, oh well, it would. Absentmindedly she touched her champagne blond wig, moving just one or two hairs. Perfect, she smiled and went to her jewelry case and added the silver and blue earrings, and the beautiful silver and blue necklace she bought especially for this dress. Jill added rings, a watch and a bracelet and then applied her perfume. She was done, she looked at her watch, and it was six-thirty, right on time.

Jill strode confidently over to the door that connected the two suites and knocked on the door. In just a few seconds Paul opened the door. Paul gasped. Jill was absolutely gorgeous. Paul was wearing a black tuxedo, but felt terribly underdressed. Jill knew she had him, she smiled sweetly and held out her hand and asked, "may I come in?" Paul quickly took her hand and escorted her to a chair in the sitting room. Once he had her seated he poured her a glass of wine, and said, "to the most beautiful woman at the party tonight. Thank you for letting me be your escort." Then they each took a drink, and Paul said with all the honesty in his heart, "My god Jill, you are more beautiful than last night. I can’t believe it!" Jill blushed, and simply said, "it is the least I can do, and after all I am with the most handsome man here."

After a few minutes they mutually decided that they needed to go downstairs before they ripped each other’s clothes off. Jill went back to her room to check on her make up and her hair. Paul put the wine away, and said he would come around to Jill’s door to get her.

Within minutes they were once again holding hands on the elevator on their way down to the ballroom. The room was already fairly crowded. The twosome made their way to through the room and found Reggie and Mary. They were sitting with four other cross dressers. There was just enough room for Jill and Paul. Mary motioned for Jill to sit next to her. She whispered that she had lots to tell Jill. Paul introduced himself to the table, and soon they were eating. The first part of the evening passed quickly. Dinner, announcements, and then entertainment were all on the agenda and went on with a minimum of notice by the people at the table.

While the announcements and the speeches were going on Jill found out that Mary had spent the night with a real man. Mary blushed as she told Jill. Jill asked if she knew him from before and if she used some protection. Mary said no and yes, and that she would see him at the dance later. She didn’t say it, but her eyes told Jill she thoroughly enjoyed herself.

Soon the tables were cleaned of dinner dishes and the entertainment ended, and the dj started playing. Paul and Jill sipped on their wine as they watched couples get up and dance. They talked about the evening, and watched Mary dance with the guy she introduced to them as Billy. He was thin and slightly taller than Mary. He never took his eyes off of her as they talked and danced. When the dj played Misty they danced. Paul held Jill tight, and when she lifted her head off of his shoulder and looked into his eyes, he asked her if she wanted to go upstairs. She smiled broadly, and said, "I thought you’d never ask."

They quickly said their goodbyes to the folks at the table. Jill made sure she had Regina’s and Mary’s e-mail addresses. She kissed Mary goodbye, and whispered "be careful". Mary smiled and said she would be. Then Paul took Jill’s hand and they wended their way through the ballroom and up to Jill’s room.

Jill opened the door and asked if Paul would get her a glass of wine and wait for her in his room. He readily agreed, and headed over to his room. He knew that Jill would be changing clothes. She was out of her dress by the time he made it to his doorway. She was into the new peignoir she purchased that afternoon by the time he had the wine poured. She was ready to go to him, but she waited. She wanted to let the excitement build-good grief, she thought, I am acting like a woman!

Paul used the time to change out of his tuxedo. He left on his boxers and put on the hotel terry clothe robe that was hanging in the closet. He was seated on the couch when Jill walked into his suite.

They never drank any wine. Within moments they were we on Paul’s bed. Within moments after that they were both naked. They spent an hour exploring each other’s bodies. They took turns kissing virtually every part of each other’s bodies. They gave each other massages. They spent some time in the ‘69’ position. Finally, with no plan and without words Paul found himself on top of Jill. He slid onto her penis and they each gasped. Paul leaned down and kissed her softly.

Jill put her arms around his neck and whispered, "I love you". She meant it with all her heart. She pulled Paul down on top of her. Paul felt Jill’s penis all of the way inside him. They made love slowly. They talked of how wonderful this weekend had been. They discussed how they would go to the airport together, and how they would make plans to meet for dinner on Wednesday night. They smiled and laughed and still stayed together. Paul started to speed up and Jill squirmed under him. He didn’t want this to end, so he lifted Paul onto his face. He sensuously caressed Paul’s vagina and licked him to several orgasms.

When Paul couldn’t take it anymore he slid back down onto Jill. As he did he slid back onto her penis. Jill was beaming. She loved to please her "men" like that. She wanted to come now. She pulled a pillow under her butt and started to rock up and down. Paul joined her and they slowly picked up speed-until they were bouncing off the sheets. Then they came. It was wonderful, it was earth shattering, but it was sad too. Jill knew this orgasm signaled the end of the best weekend of her life. She pulled Paul to her and hugged him with all her might. She felt the tears flowing down her cheeks. Paul lifted his head to see Jill crying. Instinctively he knew, he as she had been there. He put his head back down on Jill’s shoulder and held her.

That’s how they fell asleep. Neither remembered saying good night, neither remembered ever moving. They simply fell asleep with Paul lying on Jill, their arms wrapped tightly around each other. It was the most wonderful sleep either could have asked for.

Paul awoke first, and decided to do something for Jill. He tucked under the blankets and kissed Jill’s dormant penis. The second kiss caused quite a stir; the third brought it to attention. Before Jill had even started to wake up Paul was bobbing up and down on her staining erection. Jill stirred and started to remove Paul from her swollen appendage. Paul simply brushed her hand and halfhearted protests away. She merely adjusted Jill in the bed and worked merrily away at pleasing this most wonderful person that had entered his/her life. Within in minutes Jill erupted into Paul’s mouth. Paul hungrily sucked and swallowed all of it. She wanted to have Jill in him. She wanted to taste, no savor, this sweet ejaculate. When Paul had taken all of it, he positioned himself above Jill and gently kissed her. Jill tasted the semen along with the now familiar taste of Paul. Jill tried to return the favor, but Paul said that they didn’t have enough time. They needed to pack and get to the airport.

Jill suggested that they take a shower together, but she knew that Paul was right. They had just enough time to get organized and get to their flight. Jill pretended to pout and she stuck out her lower lip. Paul laughed and suggested that they join the mile high club on the way home. Jill, although not sure if Paul was joking or not, readily agreed to become a member with him. Paul saw that Jill was in earnest, and thought what a wild woman. He was kidding, but when he saw that Jill would do it, he almost thought that he would.

Neither wanted to get out of bed, but they had to do it. Jill walked into her suite and went straight into the bathroom. She looked in the mirror and saw that she looked awful. She removed the remnants of her makeup, and then stripped her finger and toenails of their polish. She then went into the shower. It was Jill who entered into the steaming water. It was Jill who as she started washing was near tears. But it was Jack who exited the shower. As he wrapped the towel around his waist in preparation to shave he wistfully looked at the cosmetics bag that was now packed and ready for the suitcase. His process for getting ready to leave was now simple. He was already planning their trip.

In the next room the situation was reversed. Paul went into his bathroom quickly took care of his morning ablutions and stepped into the shower. Five minutes later it was Paula that stepped into the steam filled bathroom. She started to put on her "face" and began to worry about meeting Jack. She worried again about her surgery. She couldn’t believe the insecurity she felt.

They both packed in silence. Jack finished about one minute ahead of Paula and wandered into her suite to see her finish her last bag. Jack saw a tall woman with short black hair. She was wearing a pretty red skirt with a white silk blouse, nude stockings and Jack was happy to see heels that must have been at least two and a half inches. Jack smiled without thinking about it. She was very attractive. As he stared, Paula turned to see him. She smiled too. She saw a six foot three inch man who was very fit and very handsome. Jack was wearing a nice combination of browns. Paula thought, "Hmm he dresses well as a guy too." Jack walked up to her and took her hands. He said, "Paula, you are lovely." He kissed her. He kissed her passionately. Neither seemed to notice the change in roles, they just seemed to be comfortable with each other.

"I called for a bellman to take our stuff to the lobby," said Jack. Paula nodded and started to take her bags to Jack’s room. He stopped her and said with a smile, "Now it’s my turn for this."

Within minutes the handsome, and tall couple (Paula was Jack’s height in her heels) were walking through the lobby. They were holding hands and smiling. Each was looking to see if they would spot anyone from the conference. They didn’t. Jack was mildly disappointed that he didn’t see Mike the doorman. He wanted to thank him for warning him about the weekend!

Paula sat close to Jack in the cab. She said she couldn’t believe how fast the weekend had passed. She looked deeply into Jack’s eyes and said she truly wanted to see him again. Jack squeezed her hand and said that there was no chance of her getting away from him-as Paula or Paul. Paula laughed and said that they would need to discuss the fact that they seemed to be a foursome.

Jack took care of checking their bags, and they walked to the gate. Within minutes they were on their way to Chicago. Jack had used upgrades and they were flying home first class. The flight attendant asked it they wanted drinks and Jack suggested champagne. When each had a glass, he toasted her and she him. They each thanked their lucky stars for meeting. Two hours later as they stood to leave and waiting for the door to open at O’Hare (they had decided not to join the mile high club on this flight, but decided they would eventually), the flight attendant asked them if they were on their honeymoon. They laughed, and Paula, said, "yes, it is that obvious?" The flight attendant said, "Yes, I don’t think I have ever seen a couple so much in love." They both blushed, and thanked her.

As they walked through the airport to the baggage claim they held hands. They didn’t just hold hands, it was if they clung to each other. Neither wanted their weekend to end. Jack got a skycap to help with their bags as each called for their respective limos on their cell phones. Paula’s limo arrived first. Jack helped load her bags into the trunk. He kissed her passionately there at the curb and she returned his kiss with equal passion. They each vowed to talk later Sunday night. Paula got into the limo and as it pulled away she cried. She had never been so happy in her life.

Within minutes Jack’s limo arrived. He helped the driver load the trunk, and then sat alone in the back. He didn’t need to give the driver directions because he had used this gentleman before. Jack buried his face in the newspaper. He didn’t want the driver to see that he was crying. He had never been so happy in his life.

 

Hopefully to be continued.

 

© 2000
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