A Professional Proposition

by Robbin Renee Wells

 

As Kelly slid across the front seat of the car, he crossed his bare legs and felt quite warm and secure. However, as he listened to the sound of the soft jazz playing, and gazed into the lights of the oncoming traffic, he began to think back across the memories of the previous months' journey to his present reality. Letting his mind drift, and his head gently rest upon Jules shoulder, a slight smile came across his face.

Kelly was twenty-five and had just graduated from law school, when it all began. His fiance, Allison, had also just graduated from the same law school, and had landed a job in a very prestigious firm in downtown Philadelphia. Although neither of them had any particular ties to that area, Allison's job mandated their moving into a suburban townhouse in the metropolitan area. In fact both Kelly and Allie, were quite excited about the move, and shortly after having taken the Pennsylvania bar exam that summer, they were on the road.

Kelly was particularly excited about the move and his newly found freedom. For the past fifteen years he had been waiting for the day that he would be done with school and out in the working world. Although he didn't have any job waiting, and his mediocre grades made finding a good job like Allison's much more difficult, he knew that he would enjoy not living in dorms or studying for periodic exams.

In fact, Kelly had been looking forward to taking some time off and experimenting with a certain, hidden part of his life. Although he had told Allie all about his particular proclivity, he had hidden it from everyone else. Only during the last year in school did he begin to start finding some time to reacquaint himself to his feminine interests.

Like so many others, ever since an early age, Kelly had been attracted to women's clothing and more so a feminine appearance. As he had explained to Allie one evening during their third year in law school, he didn't quite understand why he was totally captivated by getting dressed as a girl. However, he had learned that it didn't go away and that he still found himself staring at women, wishing that he appeared like them. In fact, he had long ago realized that it went well beyond just wearing women's clothing, and although he didn't explain that to Allie, he knew that he wanted to experiment with the total appearance and persona.

In that regard though, he was quite fortunate. As Kelly was only five feet six inches tall and had a very slight build. Despite his interests in sports growing up, he hadn't really played any, with the exception of golf. He enjoyed more scholastic interests and listening to music. Then of course, he also enjoyed being dressed so to speak. While living at home with his divorced mother, he would take any opportunity that he could to experiment with her clothing. He especially enjoyed the soft feeling of her lingerie and hose, and the look of her shoes. During high school, he had even started to experiment with the total look and became quite adept at applying makeup.

However, during the dorm living years of college and first two years of law school, he was forced to repress his desires and could only enjoy his fantasies vicariously through photos or his imagination at night in bed. He would imagine being completely dressed and had even been aroused at the thought of being totally female, in a sexual sense. But during those days he would reach a climax and it would be over for the next day or so.

In their third year of law school, Kelly and Allison, moved in together and shared a small one bedroom flat at the edge of campus. It was then that Kelly began to feel enough freedom and found enough time to again express his feminine side. Yet the new opportunity also presented a new anxiety and that was telling Allison. He had decided that he had to tell her, especially since it was her clothing that he was beginning to fantasize about wearing.

He got so worked up the day that he told her, that he was a total wreck by the time that she got home from the library. They sat down at dinner, and after some casual conversation, Kelly quietly mumbled something.

"What did you say dear..." Allsion asked.

"Allie, I have to tell you something..." Kelly answered.

"Well go ahead, Kelly. And please, relax, you're almost shaking..." Allison said, reaching out to hold Kelly's hand.

"Well, I'm not sure how to start. It all started, and I don't know why. But I do want to. I mean its all I think about sometimes..." Kelly sputtered, and started to feel the tears well up in his eyes.

"Do what, Kelly. My goodness, now you've got me shaking..." Allie replied, now also on the verge of crying.

"I. I like to. I like to dress up like a girl..." Kelly said, and there it was out in the open to another person for the first time.

It seemed like an eternity to Kelly, but suddenly Allie started to giggle, and cry at the same time.

"Is that all. I mean that's why you're so anxious. I thought that you wanted to leave me or something..." Allie exclaimed.

"No, Allie, not at all, but I've been through this before and although I've tried, I just can't stop wanting to do it. And I thought that you would want to leave me, if you knew. You're the only person that I've ever told. But I just had to tell you..." Kelly quietly expressed through his own tears.

"Oh you poor dear, come here..." Allie whispered leaning over to hold Kelly's head and kiss him on the cheek.

Then after a few more moments, Allie lifted Kelly's head.

"Would you show me, tonight, hon..." Allie asked.

"Sure, if you want me to, Allie, but really I don't mean to put this on you. Its my problem..." Kelly said.

"Hon, its not a problem, now get changed and let me see..." Was her reaction.

Kelly couldn't believe it, as he felt like a weight had been lifted from his shoulders. He quickly took a shower and went into the bedroom to change. He didn't go overboard, just some light makeup, panties, a bra stuffed with socks, a light blue turtle neck sweater, navy blue tights and a jean skirt. As Allison was only an inch shorter than Kelly, her clothes fit quite well. Although a half size too small, Kelly managed to slip Allie's, dark blue, one inch pumps onto his feet and pulled his hair back into a short pony tail.

There he was, with his femme persona looking back in the mirror. He was beginning to get a bit excited, but was also nervous about going out to greet Allie. Without hesitation, he opened the bedroom door and walked out into the living room.

"My goodness, Kelly, you look great..." Allie said as she turned from the television.

"Turn around. Let me see. I can't believe that. You have done this before. Very nice..." She continued.

Kelly was more than happy to model for her. But something held him back from really being as effiminate as he usually was, while alone. Probably the intimidation of the moment, he thought, or maybe it was the basic, fundamental appearance that he wanted to take further. In any case, that's how he began to get back into his particular interest, and over the rest of the year he dressed almost once a week. Yet it was still a solitary hobby, as although she expressed her approval, Kelly could tell that it was more of a putting up with kind of expression, on Allie's part.

As graduation, the bar exam and the move to Philadelphia each transpired, Kelly was again, getting quite excited about an opportunity that he had never experienced. Some totally free time and almost complete anonymity. As Allie could tell and Kelly explained, the need to take some time off and just experiment a bit was coming to a crescendo. So, Allie agreed that while he was looking for a job, she could put up with a bit more experimentation on his part.

After they moved into their townhouse, and Allie started her job, Kelly started looking for work. Though he quickly learned that the market was full of newly graduated lawyers, and that he was not the most marketable commodity in the job market. However during the same time, he started to accumulate a small feminine wardrobe of his own, and that was particularly exciting for him. Each morning he would send out numerous resumes and then during the afternoon, he would go out shopping or browse the internet for feminine apparel. After only two weeks, Kelly had several dresses, blouses, skirts, panty and bra sets, pantyhose and pairs of shoes. In addition, he had purchased two wigs, breast forms and a complete supply of makeup. At last he was ready to really enjoy his first day en femme in his new home, he thought. In fact he had already set up the second bedroom as his own little computer, guest room, with all of his wardrobe. It was perfect with a small walk in closet, pullout sofa bed and own bathroom.

But that was the same Friday that Allie came home with some good news, for her at least, as she explained over dinner.

"Hey, dear, I have some good news. There's a job opening in the office for a legal assistant." She started.

"What do you mean, Allie..." Kelly asked.

"Well its only temporary and just clerical assistance, but there is a very large litigation case that they need clerical help with. You know, copying, delivering and various odd jobs. And instead of overloading the secretaries, they want to hire a couple of people, part time, for a limited period..." She said.

"And you want me to apply..." Kelly inquired.

"Well, it would be something. And I know that its not what you want, but it would be something..." Allie responded.

"But, Allie, I'm not sure..." Kelly exclaimed.

"Well, I know that you want to relax a bit more, and its not a legal position, but I think that it would be good for you to get out. And you know, I've noticed the special purchases that you've been making...:" Allie said in between bites.

"You've noticed, huh. And I should be able to pay for them, I guess..." Kelly said.

"Yes, you should, hon..." Allie said, smiling.

"Alright then, how do I apply..." Kelly asked.

"No problem, you're already hired, and you start next week. Four hours a day, Monday thru Thursday. So you can still have time to have a bit of fun on your own. Alright..." Allie whispered, leaning over to kiss Kelly.

"Alright, Allie. You're right, I guess..." Kelly replied.

The rest of the weekend was spent with both of them continuing to put things away, still getting settled and all too soon Monday morning arrived. That morning, Kelly rode into work with Allie and started his new temporary position. After the usual paperwork was completed, he was taken down to the secretarial area of the office, where all of the word processing, copying and fax machines were located. He was introduced to his supervisor, a young paralegal, named Heather, and she gave him his first assignment, copying several boxes of depositions and delivering them to various offices of young associates throughout the office.

After only a couple of hours of copying, and delivering the copies to the various young associates who would tell him to put them right there, or turn and point while on the phone, Kelly was more than a bit put off by of his socalled contemporaries. He felt jealous and slighted by their aloof demeanor.

In fact upon returning to the secretarial area of the office, Kelly was ready to quit. But then he realized that he had made the agreement with Allie and, like it or not, he was going to follow through. Then as the morning continued, he started to notice that he was the only male in that area of the firm. Although, he felt a bit uneasy he began to enjoy momentary looks at the young female employees in their short skirts and dresses and heels. It wasn't a lusting type of look, but more of admiration for their appearance. In fact the mindless work, let him imagine also being dressed that way. He even started to imagine wearing pantyhose all day, and how it would feel, and the look of the painted toes, tucked inside of the high heels.

The silver lining, so to speak, he thought, as he left work that day at noon and took the train back out to their suburban home and a bus to the entrance of the townhouse complex.

That afternoon, Kelly also began another important part of his journey. He went to a tg chat room that he had come across in his shopping forees, and began chatting with other girls. He was surprised at the common experiences and feelings that were expressed, and most importantly attracted to a young tgirl that said she was from the same area.

"My name is Casey...And I live in the Philly area, Kelly...Been here long..." The instant message read.

"Hi, Casey...Not long at all, and looking to meet other people and maybe get out..." Kelly quickly typed.

"Do you go out, dressed, hon..." Was the reply.

"Never have before, but interested..." Kelly wrote.

"Do you pass..." Casey sent.

"I think so, but have never been out..." Kelly replied.

The conversation continued for at least an hour, and Kelly was thrilled with meeting another person locally. He was very apprehensive, but also had this burning need to get completely dressed and go out to meet other people. The two chatted about where they lived and their current situation. Casey was a few years older than Kelly, and a bit taller. She was also more expereinced, in that she said that she went out both during the day and to clubs in the city at night.

"Yes, in fact there is a great little club in the city called The Perfect Lady, where a group of us meet every Friday night...want to join us..." Casey wrote.

"I would love to, but am very nervous..." Kelly wrote back.

"I understand, but don't be...You could stop by my place and I'll drive...Your description sounds great..." Casey offered.

"Well, I'm not sure...but here's my email, please stay in touch...I have to go now..." Kelly replied, and with that shut off the computer. It was all too much and was getting late. Yet he also knew that he wanted to meet Casey and go out.

The rest of the week went by much the same as Monday. Each day, Kelly would work at the firm until noon and then come home and play on the computer. Tuesday and Wednesday, he returned to the same chat room, but didn't see Casey online.

However, on Thursday when Casey got home, he went onto the internet and found an email from Casey.

"Going out tomorrow night and meeting a couple of other girls at the Perfect Lady...Want to come...Call me at 543-740-2981...About seven or so, and I'll give you directions...Hope that you can make it...Casey..."

Kelly couldn't believe it, he was so surprised, but so thrilled that he didn't know how to respond and instead shut off the computer. For the next two hours he kept going back and forth over the pros and cons of such a meeting. Then he finally decided that it was time to get out and have some fun, as he thought about the young girls in the secretarial pool at work in their short skirts, hose and heels.

He quickly got undressed and slipped into a warm shower, where he did what he had never done before. He shaved his entire body. Although he was fair skinned and didn't have much body hair, without thinking, he took a razor and softly removed all hair from his body, his legs, under his arms, around his little nipples and even around his delicate excitement. It was something that he had always wanted to do, but never had the occassion. Now he had found the occassion.

After a half hour in the shower, he got out and felt the new feeling of a soft, completely shaven body. Next he slid moisturizer all over his legs, arms and chest. It felt so nice, he thought, and without any further thinking he went downstairs, into the living room and manicured his nails. Again, without hesitation, he applied two coats of a cherry red colored nail polish to his toes, while he sat in front of the television, wearing only Allie's white, terry cloth bathrobe, watching an afternoon talk show.

When he was done, he felt so thoroughly feminine. But he also knew that he didn't want to have Allie see this right now. So he went upstairs and slipped into a pair of jeans, shirt and socks. With that done, he started dinner.

Allie got home around seven and they had a quiet dinner together. She mentioned to Kelly that some of the young associates were going out the next evening and she wanted Kelly to meet them downtown. Kelly explained that he really didn't want to, working in the secretarial pool and all, and Allie didn't push the topic. Kelly also explained that he wanted to update his resume and that he was staying up late that night.

So around ten or so, Allie went to bed and Kelly retired to his computer room. He waited an hour or so and then dialed the number that Casey had left on the email. He was nervous that it was too late and almost hung up when he heard a somewhat male voice answer.

"Hello..."

"Hello, is Casey there..." Kelly whispered.

"This is Casey. Is that you, Kelly..." The voice answered.

"Yes, Casey. Sorry to call so late, hope that I didn't wake you up..." Kelly continued in a quiet voice.

"Well, you did, hon, but that's alright..." Casey replied.

"I do want to make it tomorrow night, Casey..." Kelly again whispered.

"Great, hon. Look, get ready, and call me tomorrow around six and I'll give you directions to my place, and we'll go from here..." Casey said.

"I will, and thanks, Casey..." Kelly said.

"Hey, take care and get some rest dear..." Casey again replied.

He was almost trembling as he hung up the phone. But it was a good kind of trembling, looking forward to a day off and a day to get ready for his first night out. So he changed into a tshirt, long flannel pajama bottoms and a pair of socks, again not wanting to let Allie know what he had done that afternoon. He had thought about sleeping in the computer/guest room, but didn't want to attract attention. Little did he realize how many nights he would thereafter spend on that pull out sofa.

The next morning took forever to arrive. Kelly hardly slept in anticipation. The thoughts of how he would look and how he would ever pull off going out, kept him awake for a good portion of the night.

So when the morning did arrive, he didn't even try to get up with Allie. Instead he slept until almost noon, and when he did finally wake up, he stayed in bed for another half hour enjoying the feeling of his soft body against his clothes and the sheets.

Eventually he got up and heated a cup of coffee leftover from the morning. He didn't do much until midafternoon, when he nervously called Allie at work. She again tried to persuade Kelly to join her and some other associates for a drink and dinner after work. When Kelly again turned down the invitation, saying that he might catch a movie instead, Allie gave up and told him that she would probably be home around eight or so.

Great Kelly thought, as he hung up the phone and turned his interests to getting ready. Plenty of time to get ready and out, before any further explanations were necessary.

Feeling a need to relax, Kelly slipped into a warm shower. The feeling of being completely feminine returned as he washed his soft body. After a half hour or so, he turned off the water and again rubbed moisturizer all over his body. He completed his initial preperation with a very close facial shave. Although he didn't have much of a beard he wanted to make sure that his face was completely smooth and soft. Finished in the bathroom, for the moment, Kelly grabbed Allie's terry cloth robe and went downstairs to do his fingernails.

He had purchased a set of stick on, artificial nails, in a french manicure style. Although he loved the look of the nails without polish, he knew that he wanted them to match his toes and applied two coats of the same cherry red nail polish to his fingers.

After letting his nails dry for more than an hour, it was almost four o'clock. Time to start the makeup, he thought. So upstairs he returned to the computer room bathroom, with his cache of makeup items. He started with a light, water based, foundation and transluscent powder. Next he followed with black eyeliner, masscara, soft eyshadow and some blush. Kelly could hardly keep his hand from trembling as he outlined his lips with a red lip pencil and filled them in with a cherry red lip gloss, that matched his nails.

Perfect, he thought, as he finished his efforts. Maybe a bit overstated, but definitely a major difference and improvement from his early days back at school. He had always dreamed of dressing more fashionably and provocatively and it was certainly happening.

Without any further hesitation, he pulled a tight wig cap over his short, blonde hair. Since he had started looking for a job, he had been forced to get his hair cut short and couldn't keep it long enough to form a short tail, as he could in school. But that was alright, as he had been completely fascinated about what he would look like in the long, over the shoulder, curly blonde wig he had purchased. It wasn't a bright blonde color, just light enough to be considered blonde, with soft curls that caressed his face and fell just over his shoulders, with short, light bangs in front.

After the wig cap he took out a gold, broad band necklace and clasped it around his neck. He followed that piece of jewelry with two small, gold, hooped, clip on earrings, a small gold watch, with a black felt band, several small gold bracelets and three gold rings.

Then he was ready. Kelly went back into the computer room and pulled the box containing his wig from off of a shelf in the walk in closet. He removed the wig from the box and shook it out, as he quickly tiptoed back across the room to the bathroom.

He couldn't believe the look as he slipped the wig over his head and started to gently brush out the curls and bangs. Within fifteen minutes he had, what he considered, the perfect look. So much more provocative and fashionable than his former appearance. It was great, and he could feel his excitement start to overpower his nerves. Again, he started trembling, staring at the reflection of the soft, sexy girl, he saw smiling back in the mirror.

Looking into the mirror, Kelly totally changed his demeanor. He began to tilt his head and shake the soft curls from side to side, all the while giggling. He was enjoying the moment so much, but also realized that he had to complete the change.

So back into the computer/guest room he swayed and took a pair of white satin panties out of the top drawer of his dresser. He slipped them up his legs and over his little behind, pulling his testicles up into his body and his excitement between and behind his legs. Then he rolled a pair of white pantyhose up his legs, while sitting of the sofa. He absolutely loved the look of his red toes showing though the sheer stockings, as he stood to adjust the fit of the hose.

Kelly took off the robe, letting it gently slide off his shoulders and onto the floor. He followed that with a matching, white satin bra, and breast forms, which, when adjusted, provided some cleavage and a nipple effect in front. He finished the lingerie with a white waist cincher and a white camisole. He had thought about a white, half slip, but decided to be a bit risque and enjoy the look of his legs, should his dress just happen to slip up his thighs.

Almost ready, he went back over to the closet and took a red, short sleeved dress, with a soft, white floral design, out of the closet. It had sleeves that fell just above his elbows and buttons down the front, with a matching fabric belt at the waist. The dress wasn't overly short, but not long either, as the hem rested four inches or so above his knees, with a small slit up the front, created by the two lowest buttons, that Kelly left open.

He completed the outfit with a pair of three inch, red pumps with an open toe. As he softly slipped the red shoes onto his delicate feet, he could feel the electricity pulsing through his body. He gently stood and walked into the bedroom to look in the full length dressing mirror.

Oh my, was all he could mutter to himself, as he stared, turning every which way, at the soft, sexy girl in the mirror. He was completely feminine and loving every look. Kelly was totally enticed by his own reflection and couldn't believe how it made him feel.

But it was almost six o'clock and he had to call Casey. So he grabbed his black, clutch purse and light tan, rain coat for the gentle autumn air. He slowly proceeded down the staircase, feeling his hips sway from side to side and his breasts softly jiggle inside of the bra.

Nervously, he reached for the phone and dialed Casey's number. After two rings he heard the same, somewhat male voice.

"Hello, Casey..." Kelly said, not knowing whether to keep talking or hang up.

"Kelly. So glad to hear your voice, hon..." Casey replied.

"I'm, really, well..." Kelly started.

"Nervous, I know, dear, don't worry. So here are the directions and don't hesitate, hon..." Casey said, reassuringly.

A few minutes later, Kelly hung up the phone, with directions in hand. It was still twilight out and the mid autumn evening still had some sunlight left. This was intimidating to Kelly, as he slipped his arms into his rain coat and held onto his car keys and clutch purse. He started to worry about his old car and what could happen on the drive to Casey's. But then he regained his composure, thinking that it was an easy drive and decided to listen to Casey's advice.

Without any further thought, Kelly walked out the front door of the townhouse, and pulled it locked behind him. No turning back now, he thought, as he started to quickly walk out to his car, which was parked just in front of the townhouse. He felt great, as he swayed and bounced, but quickly became overwhelmed by the clicking sound of his heels on the concrete walkway. Then he felt the cool breeze upon his exposed legs and wanted to retreat back into their townhouse, before anyone else saw him. But with a quiet resolve and quick steps, he clattered his way to his car and quickly slipped into the driver's seat. No one else had come out, and he was relieved as the engine started.

He hadn't noticed, until he came to a stop at the first red light, and a truck pulled up alongside in the left hand lane, that his coat was completely open and his dress had slid halfway up his thighs. He glanced at the man in the passenger side seat of the truck and gently smiled, as he quickly smiled and looked away. Then he started to really relax and enjoy the sight and feel of his totally exposed legs.

After only fifteen minutes or so, he found himself pulling into Casey's apartment complex, and the next major hurdle. He parked in front of Casey's building and turned off his engine. After a couple of quick looks in the vanity mirror, he opened his door and made a direct walk to the front door of the building. He pushed the button next to the apartment number that Casey had given him, and heard a quick buzz.

Kelly quickly opened the door and walked into the apartment building. He just as quickly walked to Casey's front door and knocked. In just a moment the door swung open, as a couple walked by and smiled. There was Casey, dressed in black capri leggings, an oversized, offwhite, vneck sweater, with black seamed hose and five inch, black, patent leather, open toed, ankle strapped heels. She had a short, dark, reddish brown, pageboy cut wig on her head and gold jewelry. She looked so elegant, thought Kelly.

"Kelly, come in..." Casey exclaimed, with a bright smile.

"You look great, let me see dear..." Casey continued, as she led Kelly into her apartment and gently walked around her to see.

"Thanks, Casey, so nice to meet you..." Kelly replied.

"Take off your coat dear, and please sit down, before you hyperventilate..." Casey said.

"Is it that obvious, Casey..." Kelly whispered.

"Not really, but I know the feeling, hon..." Casey also whispered reaching around for Kelly's coat.

With that, the two girls sat down and started a conversation that lasted two hours, over several drinks. Kelly actually started to relax and Casey could notice the change in her demeanor.

"Well, it seems as if you're ready for the next step of the evening, dear..." Casey said setting her glass down on the cocktail table.

"You mean the Perfect Lady, Casey..." Kelly replied.

"Exactly, young lady. Now finish up and lets get going..." Casey said.

"And you are more than ready, hon. Believe me you look great..." Casey added, before Kelly could say what he was thinking.

They both got their coats and took off for the city. It was as if Casey had been through it all before, Kelly thoughtm, as they drove into the city. He felt such a freedom with Casey, and could express what he thought, without reservation, and Casey seemed to be more than happy to help out a little sister, so to speak.

When they got into the city they drove to a parking garage and got out of the car. Despite Casey's seeming confidence, Kelly again became quite apprehensive. The garage was quite dark and their heels made such a noise. But out on the street they were passed by a variety of people, without even more than an adventurous glance at two provocatively dressed young ladies.

After two blocks, they had come into sight of the lounge. A large, maroon canopy, with white lettering and a white, feminine hand holding a cigarette, designated the Perfect Lady Lounge. They walked inside, past the bouncers at the door, and into the lounge. It was softly lit and there was light techno music playing on the many speakers that they passed. Within a few more steps, Casey gave a quick jerk to Kelly's arm and led her to a large booth along the wall where three other girls were located.

"Hey, Casey. Hey girl. So who's the new girl. Is she the one you mentioned..." One girl got up to say.

"Everyone, this is Kelly. Her real name..." Casey replied giggling.

"Kelly, this is Ashley, Debbie and Michelle..." Casey introduced.

"Thanks, nice to meet you all..." Kelly mumbled.

"No need to whisper, dear. Just relax..." Ashley said, as she hugged Kelly, and the other girls did also.

They were absolutely beautiful, Kelly thought as he slid into the booth, after Casey. A variety of short dresses and beautiful legs and heels. He was so excited and started to feel that excited, trembling feeling again. In fact when he started to take a sip from his first drink at the club, he couldn't stop the feeling, until Ashley took his hand and told him that they all started out with the same feelings.

He started to relax, just like he had at Casey's apartment, and time started to slip by so quickly. He was having such a great time and was even coaxed out onto the small dance floor by Casey, Ashley and the other girls. It was great, Kelly thought, as he returned to the booth, alone.

Then, while he was seated at the booth alone, the waitress came by with a drink.

"What is this, I didn't..." Kelly asked, over the music.

"I know, hon. He wanted to buy you a drink..." The waitress replied, looking at a middle aged gentleman at the bar.

He was grey haired, but very well dressed and very handsome, Kelly first thought. But then Kelly thought again.

"But I can't accept it. I mean..." Kelly began.

"Sure you can, dear..." Casey interjected as she pushed into the booth next to Kelly, as the waitress walked back to the bar.

"Maybe you should go up and thank him, Kelly..." Casey suggested.

"Casey, get real. I mean, I'm not..." Kelly replied.

"Gay, you mean..." Casey said.

"Exactly..." Kelly exclaimed.

"Well, you don't look or act like a boy right now, hon. Go ahead, besides the admirers here are more than friendly and won't push the issue, if you don't want to..." Casey replied.

"Oh, but Casey. I don't know. I mean, have you ever..." Kelly asked.

"You mean, been with a man. Well, never kiss and tell, dear. Now go on..." Casey prodded, standing up from the side of the booth.

Then, maybe as a result of the drinks or maybe just the enticement of the evening, Kelly softly slid out of the booth and walked over to the bar, taking a seat on the stool next to the silver haired man that had bought him the drink.

"I just wanted to thank you, for the drink..." Kelly quietly said.

"My pleasure dear. You really look, well absolutely lovely..." The man replied.

"Well, thanks, really, but its my first time. And I'm really not..." Kelly again quietly responded.

"You're first time out. And I'm not gay either..." He said, turning toward Kelly.

"Yes on both counts..." Kelly said, now looking at the man.

"Interesting choice of terms. Legal background, eh...My name is Jules, and yours..." He said.

"Its Kelly. Nice to meet you..." Kelly said, offering his hand, and trying to ignore the implication.

"But I can't believe that its your first time out. You look absolutely gorgeous..." Jules replied, softly smiling and looking into Kelly's eyes.

At that moment, Kelly felt a strong attraction to the grey haired man that had introduced himself as Jules. Kelly just felt that he was addressing him as a soft, feminine young lady, and he was more than head over heels in love with that feeling.

As their conversation progressed, Kelly felt a certain relaxation that seemed to transcend the relaxation that he had felt earlier. He really started to enjoy sitting on the bar stool, touching the man's arms at times and softly, giggling at his comments. Kelly had to admit that he enjoyed Jules' company.

However, all too quickly, Casey came over to Kelly to tell him that she and the other girls were leaving for another club. Kelly felt disappointed, but knew that he had to leave.

"Well, good night, Jules. It was really nice to meet you. And thanks for the drinks..." Kelly began.

"Please stay, Kelly. I can give you a ride home..." Jules replied.

"Not a problem with me, Kelly..." Casey chimed in.

"See, you can stay..." Jules said.

"Oh, but I don't know, Casey..." Kelly replied.

"Of course you can hon. Just have Jules drive you over to my place. Here's the directions, Jules..." Casey explained.

A few minutes later, Kelly found himself, still on top of the stool at the bar, next to Jules, waving goodbye to his new friends. He tried not to get nervous, but couldn't help it, after he saw Casey waive goodbye and walk out of the lounge with the other girls.

"You're nervous, alone here with me, aren't you, Kelly..." Jules softly asked, after a few moments.

"I'm sorry, but I am..." Kelly replied.

"Not a problem, lets go, hon..." Jules said, taking a last sip of his scotch.

With that, Jules got up and helped Kelly into his coat. As Jules got up, Kelly suddenly realized that he was over six feet tall, and was still more than several inches taller than he was, even in his heels. Jules quietly led Kelly out of the bar and to his car, a jaguar, which was parked across the street.

Jules opened the passenger side door and Kelly delicately slid in, as Jules went around and got in the drivers side door. After getting in, he started the engine and they slowly drove away, into the city streets.

"You know, I find it kind of interesting. It being you're first time and all. You look and act like you've been out many times before, or maybe you're just a natural. You know..." Jules spoke, as they drove out of the city.

"Well, thanks, but you do know..." Kelly responded.

"That you're not gay. Not a problem, in fact that's good. I'm not either..." Jules said, looking into Kelly's eyes.

And, once again, Kelly felt this soft feeling that made him want to slide across the seat, but he didn't.

"You don't have to worry about me, Kelly. I just enjoy the open nature and have an interest in a bit of intrigue..." Jules said, smiling and reaching over to adjust the music.

Then it seemed all too soon, that they were at Casey's apartment complex and behind Kelly's old car.

"Hey, I had a great time, Kelly, and would love to see you again. Maybe next week at the lounge..." Jules inquired leaning over.

"Well, maybe. I did have a great time, too. Thanks..." Kelly replied.

"May I call you..." Jules asked.

"I'm not sure..." Kelly said.

"Oh come on now, just for fun..." Jules persisted.

"Well only after eleven o'clock. Please..." Kelly said, and with that gave Jules his phone number.

"Thanks, Kelly, you don't have to worry..." Jules said, smiling and leaned over and gently kissed Kelly on the cheek.

With that Kelly quickly opened the door and got out. Although he actually enjoyed the kiss, Kelly knew that he had to go, and did so, without any hesitation.

After he got in his car, Kelly noticed that Jules waited until after he had started the engine and saw the headlights on, before he pulled out. The entire ride home, Kelly kept thinking about the kiss, and wondering if he had made a mistake, giving Jules his phone number.

Then, as he pulled into the complex and drove in front of their townhouse a new problem arose. Allie's car was parked in front and he knew that she was home. Kelly didn't know what to do, but decided that he would have to explain, if she was still awake. Luckily, as he opened the front door only the kitchen lights were on and he heard no sounds. It was well past midnight, and he quickly went upstairs and got changed and into the shower.

Only after he had changed into his newly found sleepwear and had put away his clothing and other accessories did Allie wake up to go to the bathroom, as Kelly slid into bed.

"Have a good night, hon..." She asked.

"Yes, just a movie and a couple of drinks, dear..." Kelly replied.

"That's good, as I had a bit too much to drink and way too much fun..." Allie said.

"I know the feeling..." Kelly whispered, as Allie got back into bed, and softly kissed Kelly goodnight.

The following weekend was a whirlwind for Kelly, as he stayed in constant contact with Casey over the internet and continually worried if Allie had noticed any residue of makeup or had any suspicion as to where he had been Friday night. But much to Kelly's surprise, there was no notice or inquiry.

During that weekend he also agonized over the feeling that he had to tell Allie, where he had actually gone and that he had gone out, completely dressed. In a sense he wanted to tell Allie, but in another sense he feared her reaction. Yet by Sunday morning he couldn't keep it in any longer. So while the two sipped on a cup of coffee in the small dining room of the townhouse, Kelly got up the nerve to explain.

"You did what..." Allie asked in disbelief.

"I even met some really nice people and the bar was totally safe. I'll even show you where..." Kelly said, trying to ease Allie's obvious apprehensions.

"I can't believe, totally dressed, Kelly..." Allie kept saying.

"Really it was alright. No problems. And it was a great time. In fact, I'm going back next Friday night..." Kelly replied.

"Oh but Kelly...Please, I'm scared of what could happen..." Allie said, finally seeming to calm down a bit.

"But, Allie, really its completely safe and I'm with other people that are totally safe. And no one, not even anyone in the complex really knows who I am. Besides I have kept that less than prestigious job, for you,

Allie..." Kelly added.

"Well you do have a point, and you are working, but where is this leading, Kelly..." Allie asked.

"Its not leading anywhere, Allie. I'm just having a good time and experimenting, doing things that I always thought about doing. You know that the other people that I met are also professionals, a successful salesman, a computer systems analyst and even, a lawyer..." Kelly replied.

"Really, and who would that be..." Allie quickly inquired.

"That's just it, Allie, I don't know. And better now than when I do land a job and can't be so free..." Kelly stated, having added that last profession, thinking of himself, for effect.

"But Kelly, I don't know. However, I guess that you do, again, have a point about the timing. Let me think about it a while before I respond any further..." Allie said.

Kelly was pleased with that response and didn't push the issue. Most importantly he didn't want to fully describe his more complete change and provocative look or having met Jules. He just wanted to try to make it alright with Allie, and reasoned that maybe less description would make things less intimidating for Allie to accept. So the rest of the day they spent together at home and not another word was said on the topic.

As usual, Kelly rode to work with Allie on Monday morning, and soon found himself down in the secretarial pool doing copying and delivering the copies to the young associates of the firm. But he seemed a bit more at ease, and ever more enjoying the look of the young women around him. He even seemed more free to fantasize about being dressed as they were, and maybe just a bit closer to being one of them, he thought.

The week progressed just like the week before, without another word on the topic and Kelly getting nervous about his plans for Friday night. Casey had again suggested meeting and going to the Perfect Lady. Kelly quickly agreed and soon Friday arrived. Much like the week before, Allie was going out with the other associates from the firm for happy hour and a late dinner. Kelly again declined Allie's invitation to join them. Although he knew that she anticipated his going out, she didn't say a word, and instead just said, be careful.

The one further thing, that week, that both bothered and relaxed Kelly, was the lack of any calls from Jules. Each evening he stayed up late in the computer room to make sure that he intercepted any calls. But none came, which made Kelly wonder why, but also made him relax as he thought that Jules really wasn't interested.

Friday afternoon and evening, Kelly kept to the same schedule and prepared in a similar way, just a new dress and shoes. Again, he went over to Casey's to start the evening, left his car, and rode with Casey to the Perfect Lady to meet Ashley, Debbie and Michelle. He wasn't even thinking about Jules, as the night progressed.

However, about half way through his evening at the Perfect Lady, Kelly felt a gentle hand on his shoulder and looked up to see Jules, who asked to join Kelly and the other girls at their booth. Again, much like the week before, following a short conversation and some chiding of Kelly, the other girls left and Kelly went with Jules, back to Casey's apartment complex. On the drive, Jules explained that he had a busy week at work and had to work late every night. He apologized for not calling and promised to meet Kelly the following week, with a soft kiss on the cheek.

Again, when Kelly got home it was late and Allie was asleep. He got changed and slipped into bed, without the need for any explanations.

The next several weeks went about the same, with the exception that Kelly was really starting to enjoy being around Jules and often found himself wondering about what it would be like to let things go a bit further. Although he knew that he couldn't, he felt such a warm feeling when Jules would gently kiss him on the cheek, goodnight, at the end of each night.

Each Friday night on his ride home, after being dropped off at Casey's, by Jules, and then when he quietly slipped into bed next to Allie who was always, fast asleep, Kelly couldn't get the thought of the soft kiss out of his mind.

After those first few Friday nights, he was completely consumed by his anticipation of what Jules meant, and the anxiety over his possible call and their next meeting.

It was Tuesday and Kelly was still anxiously daydreaming at work, which seemed to take an eternity to pass by, that day.

Then, just before he was to leave for the day, Heather, told him to take a copy of an old deposition to a conference room, where they were doing a deposition. It had nothing to do with the litigation project that Kelly was hired to work on, but apparently someone needed it to refresh the recollection of a witness being deposed. Without any thought, Kelly, took the copy up to the conference room, knocked and walked in, only to see Jules sitting there next to several other attorneys, and his client.

He didn't know what to say, and could only hope that Jules didn't recognize him. So he nervously took the copy of the transcript over to the stenographer and started to leave the room, when he heard a voice whisper back in his direction.

"Do I know you..." Kelly heard, as he looked over and saw Jules leaning back from his chair.

"I don't think so..." Kelly quietly replied, and just as quickly he left the conference room.

Kelly's mind was absolutely racing, as he didn't know what to think. He could only insist on denial, and was glad that he was finally done for the day.

When he punched out for the day, he got the train and bus home and decided that it was time to distant himself from the people that he had met and the places that he had gone. Despite several emails from Casey, he decided that he needed to take a break for a while as things were getting too close. Again, he agonized over whether he had been recognized that morning.

Then he began to wonder about who Jules really was, and whether that was really the man that he had met and had wanted to call him. So he decided to do some inquiries of his own that night, over dinner.

"So, Allie, who was that attorney doing the deposition in the conference room on the forty-fourth floor today. I had to deliver a copy of an old deposition and he seemed familiar..." Kelly asked.

"Oh, on the forty-fourth floor conference room, that would have been Jules, oh whats his last name, I can't think of it right now. He's one of the most successful PI attorneys in the area...I'm not sure what he was doing there, but he has several cases that we are defending..." Allie said.

"It doesn't have anything to do with the litigation project that I'm working on, does it..." Kelly asked.

"No, not at all, Kelly, why..." Allie replied.

"I'm not sure, just that he looked familiar. And I don't want any conflicts arising..." Kelly said.

"I don't think so. And I doubt if you have ever met him, hon..." Allie casually replied, with a soft laughter.

Kelly disliked that soft laughter, as if to say that he was not good enough. But he let it roll by and the rest of the week went as per norm, until Thursday afternoon, when Kelly got home.

There was a message on their answering machine. Kelly stood frozen, thinking that it might be Jules. Almost afraid to push the button, he finally pushed the button and listened.

"Kelly, this is Jules. So now I know why the person that delivered the copy of the deposition seemed so familiar. I've done some research and have found that you are a recent law school graduate, unemployed and looking for a job. Yet I still find you very attractive. I guess that I'm exposing as much about myself in leaving this message, but I would love to take you out to dinner tommorrow night, and maybe offer you a proposition, based upon an interesting thought that I had after making the connection. Please let me know, if you would go, and please don't be intimidated, as I'm probably just as intimidated. Although I usually don't let other people's small minds get in the way. So let me know. Here's my cell phone number, call anytime..."

Kelly was frozen by the message and didn't know how to respond or what to say. Even the message left hidden inferences in his mind and made him uncertain. Although he slowly realized, that, as Jules had said, he was exposing as much about his own self, as Kelly might be exposing. In fact, just before Allie got home, Kelly started to realize that his present situation, didn't leave a lot to loose.

By early evening Kelly had drank more than a few beers, and started to relax a bit fantasizing about what the proposition might be. Allie had again explained that she was going out for her Friday night happy hour and dinner. Kelly quickly declined the ever open invitation, and Allie simply smiled and said that she understood with a small smile.

"Well, Kelly, I don't care what you are up to tomorrow night, and that you would rather do whatever you do with your friends, but I'm going out again for drinks and dinner..." Allie said, as she got up from the dinner table.

"That's alright, Allie. And I promise that after I get a job, things will change..." Kelly responded, kissing Allie on the cheek, while clearing the table.

With that Kelly continued clearing the table and loading the dishwasher, as Allie did her usual nightly reading and was soon asleep.

Then Kelly, once again, found himself pressed against the Thursday night response requirement. Silence meant not knowing, and responding meant further exposure. But yet possible discreet exposure, which is what he was really in search of, he thought. So knowing that Allie was asleep and knowing that he wanted to explore this new opportunity, or at least find out, he dialed Jules' number.

"Hello..." Jules said.

"Hi, Jules, this is Kelly..." He said in his softest voice.

"Oh, Kelly, so nice of you to call..." Jules said.

And then, Kelly heard the muffled sound of Jules voice shout, he thought. "Its a possible new..."

"Jules, is this a bad time..." Kelly said.

"Not at all, Kelly. I'm really glad that you called. So dinner tommorrow night. I'll pick you up. Just let me know where..." Jules replied.

"Well, I'm not sure, it sounds as if..." Kelly started to respond.

"It sounds as if I'm talking to my wife. I know, Kelly. I was, but now I'm in the bathroom. And as I said, I'm not gay, just like you. But I do want to take you dinner and I do have a proposition for you..." He responded.

"I really don't mean to interrupt. I'm sorry..." Kelly muttered.

"Don't be. And don't be intimidated. I think that you will like what I have to offer..." Jules said.

"Well, if you're sure..." Kelly said.

"I think that I am, hon..." Jules replied, as Kelly gave him the directions to their townhouse.

As he hung up the phone, Kelly didn't quite realize what he had just agreed to, but knew that he was completely fascinated about the possibilities.

So just like the weeks before, and the days in between, Kelly got dressed in his tshirt, flannel pajamas and socks and went to bed. Again, he didn't get to sleep until well after two or three, tossing and turning and then finally falling to sleep in a sweet dream.

In the morning, after the usual half hour or so of lounging in bed, Kelly got up and out of bed. As Jules had said that he would pick Kelly up at seven, he waited until late that afternoon to start getting ready. Around four o'clock Kelly took his usual warm shower and did a complete body shave. He again followed with moisturizer and a close shave of his face.

Over the next hour or so, Kelly did his nails and makeup. He applied two coats of a soft, plum colored nail polish to both his toes and the artificial nails that he had secured in place on each finger. When his nails were dry he applied a light coat of the same foundation and powder. Following the foundation with a liquid eyeliner and very thick masscara. He didn't know why, but he just felt that he wanted to be just a bit more provocative that evening. A little light eyeshadow, blush and lip pencil and gloss that matched the plum color nail polish on his toes and fingernails, completed his makeup.

After the makeup, he pulled the same wig cap over his hair and put on the same accessories, the small gold hooped, clip on earrings, bracelets, broad band gold necklace and gold watch with the black felt strap on his left wrist, that he had worn the weeks before. Then the moment that he had been waiting for, the long, soft curly, blonde wig, that fell just onto his shoulders and beyond and had the nice little bangs across his face. He looked lovely once again.

However, this time, he had a much more provocative idea in mind from the preceding weeks, as far as his complete outfit went. He pulled a pair of black, opaque, nylon panties from his dresser and slid them up his legs. Pushing his testicles up inside of his body and pulling his excitement back, between his legs, he made a smooth appearance, as he pulled the panties up over his little behind. Then he selected a pair of nude, sheer to the waist, pantyhose, and gently slid them up his legs, readjusting the fit as he stood up, staring at his plum colored toes.

Kelly was so thrilled as he put the matching black, opaque, nylon bra on and inserted the breast forms, which again gave a sheer hint of cleavage and pointed nipples. Next was a black waist cincher, which pulled him so much more closer, but nothing else, he decided.

Then he went to his closet and pulled out the short, black, cocktail dress, that he knew clung so tightly to his body It had open shoulders, a scoop neckline and long sleeves, with a hem that rested tightly against his thighs more than nine inches above his knees. It was made of a soft, stretch type material, and came in only three sizes. Kelly had chosen small. Oh, he felt so good, he thought as he sat back down on the sofa and slid his delicate feet into the four inch, black felt, open toed, ankle strapped, heels that he had selected.

Standing up he went into the bedroom and looked at himself from all angles. He was once again, thrilled, just like the first night. However this time a much sexier girl was staring back, dressed in a tight, form fitting dress, that barely, but snugly, covered his shapely figure and little behind. Then looking at the clock he noticed that it was almost seven, so he went back into the guest/computer room and got his light tan rain coat and black clutch purse and went downstairs to wait. Holding the railing as he descended the stairs, he felt every movement of his trim, shapely figure inside the snug dress.

No more than Kelly had sat on the living room couch, then he heard the doorbell ring.

He got up, without hesitation and went to the front door. Opening the door he found Jules, smiling, as he gazed at his appearance. Kelly noticed Jules gazing at his legs and smiled, as he helped Kelly into the tan rain coat. Then Kelly walked out the front door holding his arm. It was the middle of November and Kelly felt the cool breeze of the early evening air on his exposed legs. He loved that feeling, and the fact that it was completely dark outside by seven at that time of year.

On this occassion, Kelly decided to make it totally like they were a couple on a dinner date and after getting in the car, slid across the front seat next to Jules. After a few minutes they were approaching downtown, but Kelly felt so relaxed this time. Like it was a real dinner date.

They parked along the street and Jules got out to open Kelly's door. As Kelly slid out, he could feel the hem of his dress slide up and expose his thighs. He noticed Jules' little smile.

Then as they walked along the street, Jules gently led Kelly into the front door of a very exclusive resteraurant, and asked the maitre dee for their table. Kelly was quite intimidated, as he thought that they were going to the lounge.

"Jules, what are you doing..." Kelly asked.

"Just relax. I wanted to take you out to dinner..." Jules replied.

"But I'm not sure about..." Kelly replied.

"If you'll pass, don't worry, hon. You are gorgeous...They'll all be looking and admiring..." Jules said.

It was the Mediterranean House, a very special and upscale resteraurant. Completely straight, and Kelly was quite unnerved.

"Just relax..." Jules said and smiled, as he slipped the waiter some money, and Kelly slid into a nearby booth.

"But Jules, I thought that we were going to the Perfect Lady. And I wore this dress..." Kelly said.

"To impress me, I hope. And please don't be worried, you look absolutely great. I love it. And just perfect for my proposition, Kelly..." Jules replied.

Although he wanted to, Kelly didn't ask about the proposition, until after the meal, a prime rib for Jules and several drinks and a salad for Kelly. But during the dinner Kelly's almost bare legs bumped more than once upon Jules legs, and more than once his hands landed on Jules's arms, and each time it sent unexpected shivers up Kelly's spine.

"So, Jules, I have to ask..." Kelly started.

"About the proposition, you mean, Kelly..." Jules replied.

"Well, yes, Jules..." Kelly said, smiling.

"Well then, here it is. Do you ever imagine yourself going full time. I mean do you ever find yourself in that part time job of yours, around all the women, just wanting to be dressed like them or to be one of them..." Jules asked.

"I'm not sure that I understand what you mean, Jules..." Kelly said.

"Well I think that maybe you do, but just aren't ready to admit it. You see, despite the amount of work that I can generate, I have always worked on my own. I dislike the big firms, but I have also known for quite some time that I have more work than I can handle. Besides I want to relax a bit more. So I'm thinking about hiring an associate..." Jules softly said.

"Well, I'm not sure where I come into this picture. Especially the way that we know each other..." Kelly replied.

"Oh hon, I think that you do and I know that I do. You see, after discovering your real situation and background, instead of dwelling on the obvious implications, it just struck me that maybe we could make this arrangement quite interesting for both of our interests. I mean you know that I'm quite an admirer and I know that you need a job, but still want to explore more. That's why the job is only open to Kelly as you are now hon..." Jules said smiling and taking a sip of his scotch.

"You mean, full time. I mean dressed. I don't think so Jules, how would I ever..." Kelly said.

"Well, than maybe you ought to take a few days and think about it, Kelly. Maybe you really aren't interested, but I know that you could be very persuasive in your arguments, the way you look right now, you know..." Jules softly whispered into Kelly's ear.

Then they both slowly got up out of the booth and Jules helped Kelly into her rain coat and out of the resteraurant.

There wasn't too much further conversation that night, as they walked back to the car or on the drive home, until they got to Kelly's townhouse. Then when Kelly was about to get out of the car, Jules leaned over and gently touched Kelly's right thigh, pulling it closer and then kissed Kelly on the lips. Without thinking, Kelly, ran his hands up, behind, Jules' neck and responded to his kiss and the feel of his hand on his thigh.

Suddenly Kelly realized what he had done and pulled back.

"I'm sorry, Jules. I just need some time, alright..." He said, as he stared back at the loving man's eyes.

"Not a problem, Kelly. Let me know..." Jules replied, staring into Kelly's eyes.

Then Kelly slid out of the car and closed the car door. He walked to the frong door of the townhouse, noticing that Allie's car was parked there next to his. He wasn't sure, but hoped that, as usual Allie would be asleep. He really didn't want to have to talk about anything, and was feeling too many confused thoughts, the kiss, the proposition, he just didn't know, and was quite anxious. As he opened the front door and watched Jules pull away, he only saw the kitchen lights on and felt relieved that he could relax a bit. So he took off his coat, sat on the living room sofa and unstrapped his heels and slid them off his delicate feet.

However as he got up, in his tight dress and walked into the kitchen in only his hose, he heard a familiar voice coming down the stairs

"Kelly, is that you.." He heard, Allie ask.

"Yes, Allie...Its me..." Kelly replied, slowly turning to face Allie.

"Oh Kelly, is that really you..." Allie quietly exclaimed.

"Allie, relax, its me..." Kelly said.

"Oh Kelly, I mean, I didn't know that you had gone this far, or shaved your legs. I mean you even paint your toes..." Allie said, again, in disbelief, looking at her feminine fiance.

Kelly didn't know what to say, as Allie came closer and ran her hands along Kelly's soft, nylon clad legs and up the sides of his dress. He felt so embarressed, but so feminine, as she looked him over completely, standing there in her oversized shirt that she wore to bed.

"Allie, just relax, please..." Kelly started, as he leaned over to kiss Allie, and she suddenly pulled away.

"I'm sorry, Kelly. And please don't try to kiss me..." Allie replied, holding Kelly back.

"What do you mean, Allie..." Kelly asked.

"I mean, even your voice sounds different. And if you weren't here inside of our house, I wouldn't know who you were. And I'm not into being kissed by another woman. You know that, Kelly..." Then Allie seemed to get a bit angry.

"Please, Allie, don't get angry..." Kelly persisted.

"Angry, I'm not angry, Kelly. In fact you do have a nice little ass and I just love those toes. Is that what you want to hear or maybe you want to spend more time in the secretarial pool, dressed like the other girls. Is that what you want, Kelly..." Allie quickly snapped.

"Please, Allie, just listen..." Kelly kept quietly saying.

"No, you listen, Kelly. I have to get some sleep and think about this. Its not like it was in school and I mean I just can't believe this, my fiance looks better in a dress than I do. And please don't expect to slide those shaved legs or painted toes into bed next to me. I have to go to bed..." And with that Allie started to cry and quickly ran up the stairs and slammed the door shut.

Needless to say, that was the first of many nights for Kelly on the sofa bed in the computer room. Despite his initial inability to sleep, the intrigue of the earlier proposition took control and he fell asleep, dreaming of his decision. Maybe Allie was right, Kelly thought, as he fell asleep, maybe he did want to take things further, fanasizing about being full time. It was then, despite the chaos of the night, that he quietly made his decision about the proposition.

The next morning was more of the same, as Allie couldn't get over the change in Kelly's appearance that she had experienced. And several times throughout the day the mood changed from a gentle inquiry to sheer anger over the provocative nature of his appearance, and what he was really doing, behind her back. However, Kellly kept his distance and silence.

Finally by Sunday afternoon, things seemed to calm down a bit, to where Kelly took the chance to describe his new job opportunity, to Allie. As they sat in the living room watching television, Kelly began, but knew that he couldn't explain it completely.

"I've even found a job, Allie..." Kelly started.

"Well, I do find that hard to believe, Kelly. Really..." Allie smirked.

"No, really. Its at a small boutique downtown. One of the girls that I met owns the shop and has asked me to work their..." Kelly said.

"What do you mean work there..." Allie inquired.

"Well its a small shop that sells womens clothing, but caters to a transgendered clientele. And I would be on commission. From what she describes, I could almost make as much as you do, Allie..." Kelly described.

"Oh come on now, Kelly, you don't believe her, do you..." Allie replied in disbelief.

"Well, I know its not what I was looking for, but it might be worth a try. Only one thing, though..." Kelly muttered.

"What's that..." Allie asked.

"I have to dress as a woman every day for work..." Kelly replied.

"Kelly, you can't be serious. You can't do that. I mean, I was only angry the other night, when I suggested that. You just can't be serious..." Allie said, getting up off the sofa and walking into the kitchen, again getting very upset.

"I am serious, Allie. I mean, I want to try it, and see what happens..." Kelly responded.

"What if anyone finds out. I mean you leaving each day as a woman..." Allie said.

"And so what, returning each night the same way. At least its a job and I get to get out of that secretarial pool and maybe something else will come up in the meantime..." Kelly quietly added.

"Well what about your appearance and the continual changing, and again, if anyone finds out. Oh Kelly, this is way too much for me..." Allie said, staring at Kelly who had followed her into the kitchen.

"Its a lot for me too, Allie, but I think that I want to try it and see. In fact, I'll promise you that, if I am not making more than three times what I am making right now, within two weeks from the time that I start, I'll quit, and that will be the end of me even suggesting such a thing again, or even getting dressed again..." Kelly bargained.

At first, Allie just continued to stare at Kelly and then grabbed a soda out of the fridge and frimly walked back into the living room.

"You would really make that agreement, Kelly..." Allie asked, seeming to relax and starting to think.

"I would, Allie, really, and I don't want to go all the way, but would really like to experiment a bit more and get out of that secretarial pool that I'm in now..." Kelly said, thinking in the back of his mind that he could more than triple his present minimum wage pay, if he accepted the proposition.

After a few minutes, Allie replied.

"Alright then, we have a deal. In fact, I think that it just might get this out of your system for good. When do you start..." Allie asked, now smiling, taking a sip of soda.

Then Kelly went on to explain that it would take several weeks to accumulate the necessary wardrobe and give his notice to the firm, and with the holidays and all, he anticipated after the first of the year. He assured Allie that he would pay for the clothing and any other necessary purchases. It was quite strange, but Kelly sensed that Allie actually was looking forward to his newly suggested challenge.

Now, Kelly had to let Jules know that he would accept his proposition. So late that Sunday evening, after Allie was sound asleep, Kelly dialed Jules' number and nervously awaited his answer.

"Hello..." Kelly heard.

"Hello, Jules. This is Kelly. And I've decided to try it..." Kelly said.

"Great hon. But I'm trying to get some sleep, so call me at the office tomorrow afternoon..." Jules quietly replied.

"Alright, sorry to wake you, dear..." Kelly whispered, and hung up the phone.

Kelly couldn't believe what he had just agreed to with either Jules or Allie, but knew that he wanted to take things a bit further. He also didn't quite know what made him refer to Jules as dear. Again, his sleep that night was limited and difficult, but his anticipations great.

The next day, Kelly went to work with Allie who wore a soft smile on her face that morning. After work, which seemed to drag by, Kelly went home and called Jules, as instructed. Jules explained that the transition would probably take a month or so, and that Kelly's suggestion of the second week of January was perfect. He told Kelly, though that he would expect him to start getting ready right away. He had already made an appointment with a doctor and told Kelly to let his hair grow out, as much as he could. He also had Kelly make an appointment with a clinic that specialized in laser hair removal and an appointment with a woman who counseled transgendered individuals in both voice and comportment training.

Over the following weeks, Kelly quit his job at Allie's firm and followed Jules' instructions completely. Each day he had a new assignment. He saw a doctor who prescribed certain hormones and visited a laser hair clinic at which he had all signs of his light facial hair removed. He attended his voice and comportment lessons. He went shopping each day for new clothing, lingerie, shoes and hose, and even had his ears pierced. However, over that period he was not permitted, nor did he get dressed or see Jules.

During that month and a half, Kelly and Allie got along great. Atlhough Allie saw the new purchases that Kelly made each day, she was most pleased at his not going out and just being home. As Allie wasn't aware of what real changes were taking place, she even permitted Kelly to sleep in her bed a couple of nights after she came home following a few drinks. No sex, just Kelly's long flannel pajamas, tshirt and socks. Normally, though, Kelly was still getting used to the sofa bed in the computer room. Which was fine for Kelly, as he was usually up late letting Casey and the other girls in on what was going on.

By the Thursday of the first week of January, Kelly completed his last session of voice and comportment training and went home to take his usual afternoon shower. But this time he was excited, as he was finally permitted to get dressed that evening and go out to a parlor to have his hair done. Jules had called, as he did every day, and told Kelly that he wanted to meet him after his salon appointment. At last being permitted to think about his feminine appearance again, while taking his long warm shower and shaving his entire body, he realized some interesting developments, that he had subtley started to notice during the past month. As he stepped out of the shower, he felt his arms brush against his full breasts, and expanding nipples. Although only small cones they were definitely getting larger. Then he noticed how his hips were getting rounder and his waist smaller. Most of all he loved the softer feel of his skin and the lack of any need to shave his face.

It must have been the inability to get changed in the past month that made him not completely realize the changes that were taking place. But this day, as he smoothed the moisturizer around his body, he could not only see, but also sense the changes that had taken place.

In fact he also noticed that his hair was just about the same length as he had in school, permitting a short pony tail look.

Once out of the shower, Kelly, quickly got dressed into a matching set of beige nylon panties and bra. However, as he slid the smaller breast forms, that Jules suggested he buy, into the cups of his bra, he noticed how they seemed to shove his own breasts up and seem so very natural, with more than a hint of cleavage and a nipple in front. Then he slipped a pair of dark brown pantyhose up over his soft legs. He felt so great as he slipped into a pair of tight fitting jeans and pulled a light brown, vneck sweater over his head. Kelly then went back into the bathroom and did his makeup in a light tone, light massacara, pink lip gloss and a bit of blush. He finished by pulling his hair back into a short ponytail.

Not thrilled with the look, but continuing, he slid a pair of gold studded, diamond earring into each of his ears, and followed with a gold necklace, bracelets, rings and a newly purchased gold watch. They were wonderful he thought as he quickly pranced across the computer room and into the walk in closet to pick out his two inch, brown felt pumps, that he quickly slipped onto his feet.

Knowing that he had to be at the salon by five, he grabbed another new purchase, a brown leather, waist lenght jacket and threw it on. He finished the look with his brown leather, shoulder strapped purse and rushed down the stairs and out the door to his car.

As he quickly left the townhouse and walked out to the car, Kelly suddenly started to feel an excitement, that he had never before experienced. His own breasts were actually bouncing and his nipples were starting to get excited, sending tingling sensations throughout his body. That sensation intensified, as he started the car and felt his arms brush against his nipples, with every turn of the car.

He couldn't believe that this was happening, but had to continue, as he pulled into the little strip mall, where the salon was located. Again, without hesitation, he got out of the car and walked into the shop in full confidence, despite his nervous feelings.

"Hello, I'm Kelly..." He said to the girl at the front counter, for the first time using his new voice. It was a bit higher, but softer, with more expression and a much more feminine tone.

"Oh, Kelly...Come right back here, and lets get you out of those clothes..." He heard a low, feminine voice say.

"I'm Constance, and I'll be you're technician, dear. You are right on time, now get changed..." Constance said, leading Kelly back to a changing room in the back of the salon.

"Here's a robe, hon, now out of your clothes. And I mean everything, except you bra and panties, and come out when you're ready..." Constance said.

 

(continued)

  

  

  

*********************************************
© 2004 by Robbin Renee Wells. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.