Tess's Transformations: Life of the Party

Printer-friendly version
Synopsis:

Synopsis: Jack’s quest to find the best costume for the big company party starts a series of events that leads him to a whole new life. Establishing the primary characters of the new Tess's Transformations series.

Story:


Tess's Transformations: Life of the Party

By Julie O.

Edited by Amelia R.

Chapter 1


"So, do you have your costume picked out yet for the boss's costume party, Jack?" asked Chris Washington, a tall muscular man with short black hair. He was thirty-two and was the department head for thirty employees at Chambers Industries.

"It's still a week away," replied Jack Easton as he turned around in his chair to look at his supervisor who had just entered his cubicle.

Jack was new to the company and still didn't know many people at work. He had just been hired six weeks earlier, and many people at work called him Jake or Joe. He was twenty-three and had just graduated college the previous year. He'd taken a few months off to travel around the country after graduation before he started serious job hunting. While he wasn't pleased about working in a cubicle, he had his college loans to pay off. He figured he would work at Chambers for a few years and then move on to something he enjoyed more, once he figured out what that was. He could have easily paid off his college loans, but he didn't want to raid his trust fund quite yet; he wanted to save that for buying a home.

He liked Chris and the way he seemed to have taken a special interest in him. Chris seemed genuinely interested in helping Jack succeed in his job. It was a far cry from the cut-throat business world he had expected.

Chris cocked his head. "You've done such a great job so far that I keep forgetting that you're new here. Mr. Chambers costume party is a big deal around here - no, make that a huge deal. People have gotten promotions by showing up in a particularly good costume, and conversely some have lost their jobs by not showing up. The theme is crime and punishment this year, and you better come up with something good."

Jack nodded. "So what are you going as?"

"1930's gangster. I picked up a real nice pinstripe suit at a vintage clothing shop and a matching fedora," replied Chris. "I like the older age of crime better than today's criminals. They had more class."

The man in the next cubicle walked in on the conversation. "I've got my outfit too," he said.

"What are you going as, Tomas," asked Jack.

"A 1980's drug dealer, you know like from Miami Vice or Scarface," he replied with a suddenly heavily Spanish accented voice. "Ju want to buy some coke?"

"Tomas, just so you know, it's a costume party," replied Chris with a laugh.

Tomas flipped him the bird. "Actually, this sort of thing does run in the family as I do have a cousin who was busted for smuggling coke back in the 80's. Moron was just three weeks out of the camps, and he ends up in prison."

"Camps?" asked Jack.

"I'm Cuban-American, and was born in Miami, but I still have a lot of family in Cuba. Back in the boatlift, Castro let many Cubans go. My cousin was one of those. Castro also let many criminals go at the same time. My cousin was in the same camp with a bunch of them and ended up working for them."

"Where is he now?" asked Jack.

"Back in jail, he's serving twenty years in Folsom in California for trafficking," replied Tomas. "Still he's the only member of my family in jail, that's not too bad, all things considered." He then began to laugh.

"I was just telling Jack how important the costume party is to the boss," said Chris.

Tomas nodded. "He's not kidding, Jack. You'd better show up and be dressed in something good," he replied. 'Mr. Chambers expects everyone to show up."

"Crime and punishment, huh?" stated Jack as he rubbed his chin.

Chris and Tomas nodded together.

"Well, I'll let you get back to work," stated Chris.

Jack turned around and stared at his computer and let out a sigh. He had enough on his plate without worrying about some stupid party. He had been planning on not showing up, as he figured no one would miss him, but he didn't like the idea of pissing off the boss either. He began to brainstorm over ideas for a costume.


Chapter 2


Just before work ended, Chris walked back into Jack's cubicle.

"Since it's Friday, you want to get a few brews?' asked Chris.

Jack thought about it and decided it wouldn't hurt to have a drink or two with his immediate supervisor. "Sure, that sounds good."

They went to a bar around the corner from the office. It was one of those upscale bars that catered to the professional office crowd.

"So, tell me about yourself, Jack," asked Chris, as their beers arrived. "I know you grew up back east. Where specifically?"

Jack picked up his mug and took a long drink. "Everywhere, nowhere, basically all over, I was sort of passed around by my relatives. My parents died in a private plane crash when I was ten. They left me pretty well off, but most of the money was in a trust fund. I think the longest I lived anywhere was fifteen months. As soon as my relatives figured out that they couldn't access the money, they wanted nothing to do with me."

"Tough luck," said Chris, noting the bitterness in Jack's voice.

"Yeah, it was. I picked a college far away from them and was fortunate to get hired here," stated Jack. He hated talking about his past, but figured that since Chris was his supervisor, what was the harm. "If I never see any of them again, it'll be too soon."

"Sorry to bring up bad memories. Okay, so what do you like to do for fun?"

"I like going to see sports. Being in a city with professional sports was one of the criteria for my new home. I also like playing tennis, skiing, and traveling."

"I know what you mean about sports, I have season tickets for football, even though it's a long drive up to Seattle," said Chris. "It's one of the few things my ex didn't take from me." He then broke into a loud laugh.

Jack laughed too. "Do you ever go to see the Trailblazers play?"

"I'm not really into pro hoops. So, Jack, do you have a girlfriend?" asked Chris.

Jack shook his head. "I was seeing someone back in college, but it didn't really click. She joined the Peace Corps, and I think she's somewhere in Africa." It was a lie, but it sounded better than the truth, thought Jack. She had actually broken up with Jack because she didn't want to settle down. It was the story of his life and every relationship he had been in ended up the same way.

"So she didn't like the idea of you going to work in the corporate world?'

"Something like that," replied Jack. "Anyway, I've been too busy since I got here to even look for a date."

"I can relate. I've been looking for the right person since my breakup. My wife forgot that a marriage involves love. I wanted to romance her, and she saw our marriage as just a partnership. Actually, to be honest, we had a rather agreeable breakup. We didn't have that much at the time as we were both starting out. After we split up, she put all her energy into her own business."

"What does she do?' asked Jack as he reached for the peanuts.

"She now has a boutique near Malibu. Last year she pulled in nearly two million," replied Chris.

"Wow," replied Jack. "Any regrets?"

"No. It's okay, I'm just glad she's happy. I guess I'm old fashioned in some ways. I'd like to have a wife who will let me take care of her. I'm not exactly having luck finding her," replied Chris.

"I guess you need a less liberated woman," replied Jack. "I don't think you'll find many of those in the business world."

Chris laughed and held up his glass. "Or maybe I should invent a time machine."

Jack laughed. "Well, in many ways, I'm starting anew here. I have a new home and job. I guess I shouldn't complain, I've only been here for six weeks."

"You're off to a great start so far. I'm very impressed with your work ethic," stated Chris as he motioned for some refills.

"I didn't think anyone noticed. Hell, most of the people back in the office don't even know my name."

"Don't worry about them. I've noticed that you're a hard worker, and so has Mr. Chambers."

"I just believe in doing a good job," stated Jack, feeling a little embarrassed by Chris's compliments. He was also surprised that the boss knew who he was.

"So, have you decided what you're going to wear to the party?" asked Chris.

"No. I've been thinking about it all day. Why is this party so important?" asked Jack as he picked up his beer.

"Mr. Chambers likes to throw a couple of events a year. He used to be a general in the army, and I think he uses these events to reward the staff, and partly to observe us. I think the costume party is done to see how resourceful we are, and to also test if we're good sports. It does make it a fun place to work."

"Well, I'm sure I'll think of something," replied Jack.


Chapter 3


Jack arrived home at his loft apartment. It was the only thing available when he arrived in town. Thanks to the many new companies opening in the past few years, the city had a severe housing shortage, and Jack was lucky to get the loft. He had lived the first two weeks in town in a hotel.

He still had no idea of what he was going to wear. The theme of the party made it even harder. He was only 5-8 and had an average build, although he was thin. His reddish-brown hair was styled to meet the corporate standards, although they'd let him keep his goatee. It had taken him most of his senior year in college to grow it, and he didn't want to shave it off, even though it was rather thin.

On top of it all, he barely knew his way around town. It was spring, and it wasn't like finding a costume would be easy. Why couldn't the party be in October? he thought.

Then it hit him. "Dumb ass," he said aloud, as he reached for the phone book. He found several costume shops, including one that was nearby, according to the ad.

He looked at his watch and saw that the shop would be closing in ten minutes. So much for checking it out today, he thought. He then opened up his laptop and started to search online.

He found a few places, but nothing really caught his eye. He had a knack for finding things online, and he tried different search keywords. He played around with the search until he found a site that made him stop and think.

Jack stared at the webpage. It was definitely a wild idea for a costume, he thought.
He ran his fingers across his chin. It would mean that he'd have to shave, but it would be worth it, he thought.

He then thought of those feelings he had had when he was younger. They were vague memories of wanting to dress up in his mom's clothes. He shook his head as if to scatter these ancient thoughts. That was all in the past, just like being part of a family. Every time he'd had those thoughts he'd tried to shake them away, as they were too strongly attached to his mom, and those memories were too painful to bring up.

No, this was just a costume and nothing else, he stated to himself. He was an adult, and he could control his desires.

He picked up his phone and dialed the number. It rang three times before being picked up.

"Tess's Transformations, how can I help you?" asked a woman.

"Hi. I was wondering if you could help me. I have a big work-related costume party to go to next week, and I was hoping you could help me," said Jack. "I know this is short notice, but I really need to make a great impression."

"Sure, that's not a problem, what do you have in mind?" asked the woman.

"The party has a crime and punishment theme, so I was thinking of going as a street worker."

The woman laughed. "Do you want a total transformation?"

"Um, I'm not sure what you mean," replied Jack nervously.

"I mean do you want me to just buy you the outfit, or do you want me to do your makeup, hair, nails, things like that," stated the woman.

"Oh, yes, that sounds good," replied Jack.

"Great, look, I'm free right now. Why don't you come down to my studio? I can get an idea about your costume and measure you for sizes," stated the woman.

"I'm sorta new to town," confessed Jack.

The woman gave him directions. "My name is Tess Wellington, and I'm looking forward to meeting you."

"Nice talking to you, Tess. I'm Jack, and I'll be there shortly."


Chapter 4


Jack parked his car and walked up to the front door of what looked like an old warehouse. He rang the bell, and a buxom woman dressed in red opened the door. Her hair was jet black and styled in a pageboy cut. In some ways she reminded Jack of a young Jennifer Tilly.

"I'm Tess, are you Jack?" she asked pleasantly.

Jack smiled back. "Yes, pleased to meet you."

"Come on in, and we'll get started," stated Tess.

They walked into a well-lit main room.

"Okay, take off your coat and let me see you," stated Tess.

Jack did as she asked.

"Not bad, you're what - five-eight?" she asked.

"Very good," replied Jack as he nodded.

"Hey, it's my job. I moonlight at the state fair and guess weights too," she replied. "Now, how attached to that chin fuzz are you?"

Jack pretended that he was hurt. "Ouch!"

"Hey, I bet you look better without it anyway," replied Tess.

"Maybe, anyway I am willing to shave it off."

"Good, even a street hooker wouldn't have that much fuzz on her chin," replied Tess. "Now if it was a circus theme party, you could keep it and go as the bearded lady."

Jack smiled and told Tess about the party.

"It doesn't matter to me; I just like helping men look feminine," she replied as she picked up a tape measure. "Now, I'm going to take your measurements. It'll help me in picking out your costume and figuring out how much will need to be either squeezed or padded."

Jack wasn't sure what that meant, but didn't ask.

"Okay, now for the important stuff, how much do you want to pay?" asked Tess.

Jack thought about his answer. Chris said that the party was a big deal so the costume couldn't look cheesy.

"Just so you know, I can make you very passable," added Tess. "In fact, I can make you look really hot."

"What would it cost?' asked Jack.

"Well, there's the clothes, underwear, jewelry, shoes, wig, makeup, and then there's my services. I can't give you an exact amount, but how does four hundred sound?"

Jack was initially surprised. But then I can look on it as an investment, he thought.

"Okay, that sounds reasonable," he replied.

"Excellent. Now, you told me that the party is a week from tonight and it starts at eight, right?" she asked.

Jack nodded.

"Good, now can you be here at five?" asked Tess.

"I think so; the party is a big deal at work, and they're letting us off early," he replied.

"Good. Now on Thursday, I want you to remove the hair from your legs, chest and underarms. Before you come over here on Friday, shave your face and be careful not to cut yourself."

"Anything else?" he asked.

"Nope. Trust me, Jackie; you're going to look great. Just be careful that none of your co-workers tries to take you home!"

Jack laughed and paid her one-hundred and fifty dollars.

"Great," said Tess. "You can pay me the rest when I have the total bill."

They went over the details of his costume before he left.

On his way home, Jack smiled and thought about how awesome his costume would be.


Chapter 5


The week flew by, and soon it was Thursday and Jack was driving home. He'd kept his costume a secret from Chris and the others. He did tell them that he had a great outfit. There was still a part of him that considered backing out of the costume, but he couldn't think of anything else to wear.

There was a nagging worry about the type costume he had selected, but he tried to ignore it. It was just a costume and nothing else.

Halfway home, he remembered Tess's instructions about hair removal and stopped at a drugstore. He decided to use a cream hair remover on his legs and arms. He didn't like the idea of shaving that much of his body. As he read the products' labels, he found that none were supposed to be used on his underarms. Oh, well, he thought, how hard can it be to shave them?

After dinner, he went into his bathroom and stripped down. The product he'd bought needed to be applied for ten to fifteen minutes before removal. He sprayed in on while standing in the bathtub. It was a foam spray, and it seemed to stay in place as he covered his legs, chest, and arms.

He watched the clock that hung above his toilet tick off the minutes. It was a cheap promotional clock that he'd gotten at a baseball game, but it kept good time.

Fifteen minutes passed, and he began to wipe the foam from his body as he showered. He was amazed at how smooth he now felt. It felt very good, he thought.

Next, he had to take care of his underarms. He decided to do this while taking a bath. As he filled up the tub with hot water, he found himself rubbing his legs.

"Damn, that feels good," he stated aloud.

He carefully shaved his underarms. It wasn't that bad, once he trimmed back the long hairs. The biggest problem he had was that his razor kept getting clogged. He also decided that he would wait until he got home from work before he shaved off his goatee, as he didn't want to give away his costume.

He was about to get out of the tub, when he looked at his pubic area, and he smiled.

"Why not?" he said as he began to trim the hair around his groin. Not that anyone would see it, but it would add to the feel of the character he was about to play.

Jack had been in several plays in junior high and high school. He wasn't that good, but he'd enjoyed it. He often ended up with roles that no one else wanted, but he didn't mind; it was just fun pretending to be someone else.

He stepped out of the tub and inspected his now relatively hair-free body. It didn't look too bad, he thought.

After putting on a pair of sweats, he flopped down in front of the TV and caught the end of a basketball game before going to bed.


Chapter 6


By noon, the office was almost empty as the staff filtered out to go home and prepare for the party. Jack left right after one and headed home. He decided to take a nap first, before shaving and heading over to see Tess.

To his surprise, he was actually excited about the party. He was a little worried that he might be going too far with his costume, but he put those ideas out of his mind. It was just a party after all. Besides, he couldn't back out now, he needed to be at the party in a costume.

It was later in the afternoon when Jack shaved off his chin hair. He'd forgotten how young he looked without it. The fact that it made him look more mature was the main reason he'd grown it in the first place. He ran his fingers over his smooth chin and shook his head.

"It'll grow back," he said to himself. He looked at the clock and decided it was time to go to see Tess.

A short time later, he was inside her studio.

"Wow, you look so much better without the chin fuzz," she remarked as she escorted him to a salon chair.

"I'll probably get carded now," he bemoaned.

"I wouldn't worry about it. Okay, I'm going to have you strip down and put on his robe. I want to do your nails, makeup, and hair first. Then we'll get you in your dress," said Tess. "Now don't worry, nothing I'm going to do to you is permanent. I will need to trim your eyebrows a little, but trust me no one ever notices."

Jack just nodded and went into a changing room. He came out wearing just a cotton robe.

"Okay, Jackie, have a seat; I'm about to make you gorgeous!"

He tried to ignore the Jackie crack.

Tess started by gluing false nails to each of Jack's fingers.

"They seem a little long," noted Jack.

"Remember, you're going to be a hooker; they don't go for the subtle. To get them off, soak them in nail polish remover, and it will dissolve the glue. I don't want them to fall off at the party."

"Okay," he replied.

"Now, while the glue is drying, I need to get started on your makeup. I've got some great bright red polish for your nails."

She first trimmed and waxed Jack's brows. "Like I said, don't worry about this. Most people don't notice brows on men, but you'd be surprised how many men get their brows waxed these days."

Tess then moved to applying makeup on Jack's face. She attached false eyelashes and then thick eyeliner before doing the shadow. Next she applied lots of mascara.

"Have you ever dressed up as a woman before? I mean, you're so calm about this."

"I did it a few times in high school for parties, and once for a school play," replied Jack. He saw no reason to tell her about THOSE feelings of when he was younger.

"Oh, okay, it's just that you're calm like some of my transgendered clients. Most straight men I get are so antsy," said Tess as she applied blush to Jack's cheeks.

She then applied lipstick to Jack's lips.

"I'll give you both the lipstick and the gloss to take with you. Put the lipstick on first, and when it dries, apply the lip gloss. It'll make you look real cheap and slutty."

Jack laughed.

"Okay, let me apply the first coat of polish to your nails," said Tess. "I'll put a bottle of polish remover in with your clothes."

The color was a bright red, which looked like it was still wet even after it dried.

"This is such a great color for you. It's also perfect for your costume," said Tess.

As Tess painted his toenails, Jack looked at his hands. It was amazing how feminine they now looked.

"Now for the wig," stated Tess. "I think this will look so cool on you. Close your eyes. I want to surprise you."

Jack smiled and closed his eyes. He felt the wig come down on his head. He could tell that it was at least shoulder length.

Tess worked on styling it, before spraying on hairspray.

"When can I see?' asked Jack.

"Not yet," she replied. She styled the hair a few more minutes before turning Jack towards the mirror. "Okay, open your eyes, Jackie."

Jack opened up his eyes and was shocked by what he saw as he looked at his reflection in the mirror. He saw a sexy redheaded woman staring back at him. His hair was best described as big hair with lots of curls. The hair seemed to flow around his face. The color was a light red, and it made him look very sexy.

"I'm stunned," said Jack. "I can't believe that's me."

"Wait until I get you dressed, you might not want to go back," Tess teased. "Here, this is a gaff; it'll hide your most masculine parts. Just tuck them up between your legs. Be careful not to pinch yourself. Put on your panties over it. Then come back out, and I'll help you get the rest on," explained Tess.

Jack did as he was told. The gaff did its job, and he was stunned at how it made everything disappear. The panties that Tess had given him were bright red. He put them on over the gaff and headed back out to the studio.

"Now, this isn't a true corset, but it will slim down your waist and still allow you some movement," she stated as she held up a black garment. She slipped it around Jack's waist and zipped it up. "Thankfully, you're in pretty good shape."

Jack felt his waist tighten slightly. He looked down and saw that he had a much slimmer waist.

"Now, sit down on that stool, and we'll get your stockings on. I'll slip them on for you, because I doubt you can do it with those nails," said Tess.

The stockings were black fishnets, and he attached each to the garters on the corset. Tess corrected this mistake.

"Your garters should always be under your panties, my dear; this way you can get to work faster!" stated Tess.

Jack laughed. "Sorry, my bad, that does make sense."

"Now, I'm so pleased I was able to find these. You're very lucky that your feet are so small," stated Tess, as she showed him a pair of thigh-high boots. "They're so cool; they're so Pretty Womanish!"

"Why did you paint my toes when no one will see them?" he asked.

"Just to be fun," stated Tess, as she helped him into the boots. "Okay, stand up and be careful; those are four inch heels."

Jack stood up, and after a near fall, he began to find his new center of gravity.

"Now, this is a pushup bra that should give you a little cleavage," stated Tess. "It has built-in silicone pads that'll help push up your little boobies to make them look larger. It's even strapless."

To Jack's shock, the bra did what Tess said it would. While he wasn't huge, it did give him the impression of having breasts.

Tess then brought out a dress.

"You've got to be kidding!" he stated.

"No, it's a spandex tube dress in bright red. Trust me, it'll fit and leave enough of you showing. Remember, you wanted to be a street whore. I also have a wrap that you can wear when you're outside. That outfit isn't built for the elements."

Jack slipped the dress on and pulled it up. It just covered his breasts and was just long enough that it covered his crotch.

"Be careful when you sit down and remember to cross your legs," instructed Tess. "Okay, the last thing is some jewelry."

She attached some large hoop earrings to Jack. They were clip-ons and looked perfect for the outfit. She also had him put a half-dozen bracelets around his wrist. She gave him a cheap watch for his other wrist. She also handed him a small shoulder bag. Inside were her makeup, lipstick, lip gloss, tissues, a few condoms, and some breath mints.

"Don't forget to include your own ID and some cash," stated Tess.

Jack reached in and held up the condoms. "Are these necessary?"

"Think of them as props! Now, just let me look at you. Jackie, you look fantastic. If you don't mind, I'd love to get a photo of you."

Jack was staring at his new look in the mirror. "I don't mind; you did a great job."

Tess had him pose in several provocative poses as she took the photos. Tess smiled to herself as she saw the real Jackie come out.

"These are great; I especially like the one with leaning up against the wall with your hands on your boobs," stated Tess as she scanned through the shots on her camera. "I'll make sure you get copies, Jackie."

Jack paid Tess the rest of the money and gave her a sizable tip.

"Thanks, this will be one of the best costumes at the party," he stated.

"I agree. If you ever want to see what you look like more mainstream, come back," said Tess.

"Thanks, but I doubt if I'll take you up on your offer," replied Jack.

"Don't be so sure, Jackie. I sense a change in you; so don't be afraid of exploring these new feelings."

"I doubt that I could ever make myself look this good," said Jack.

"Don't be so sure. I could teach you to be a very passable woman. Think about it," she said. "Oh, one more thing." She grabbed a bottle of perfume and had Jack liberally apply some on his wrists, neck, and between his breasts.

"You need to smell as sexy as you look. Have fun, Jackie."

Jack smiled and headed out. He put his male clothes in the trunk and pulled out the directions for the party. Still, as he drove Tess's words stuck in his thoughts. Was it wrong to dress like this, he thought? It wasn't hurting anyone.

Tess watched Jack walk away and smiled. Jackie was obviously transgendered, and she didn't even know it. Tess had seen it too many times, and all the signs were there. Tess also knew better than to say anything; it would be better if Jackie accepted this for herself. She hoped that Jackie would become one of her clients, as she was a nice girl and would need a mentor.


Chapter 7


Jack parked his car and stepped out carefully. He was getting better in the heels, but it was still hard walking.

He headed up to the front door of Mr. Chambers' house. He knocked on the door, and a slot opened up and he was asked for the password. Jack was temporally caught off guard, until he remembered that the instructions had listed a password. It was 'speakeasy.'

"Speakeasy," he answered softly in his best female voice.

"Come on in," stated the voice from behind the door. The door opened, and Jack walked in. He was immediately greeted by the owner of the company, Mr. Chambers, who was dressed like Marlon Brando in The Godfather. He was wearing a classic tux, and had makeup to make him look like Vito Corleone. His cheeks were puffed out, and he had a pencil thin moustache drawn on.

He even was trying to talk like Brando, mumbling his words. "Please, come in. Thank you for coming and honoring me by attending my party. Welcome to my humble home."

Jack entered, and bowed. "Thank you, Godfather." He deliberately tried to make his voice sound feminine.

"Come on in, Miss. I'm sorry, but I don't recognize you; what's your name?" asked Mr. Chambers. He prided himself with the ability to recognize all his employees. "Wait - don't tell me. Hold on... hold on, don't tell; I'll get it."

Jack cocked his head and smiled.

Suddenly, Mr. Chamber's eyes opened wide as he looked at Jack. He broke out of character and broke out in a huge smile. "Wait a second... are you Jack Easton?"

Jack nodded.

Mr. Chambers broke out in a large laugh and patted Jack on the back. "Well done! You fooled me, well done indeed! Damn fine costume!"

Jack smiled and knew that it was all worth it.

"Well, come on in and get yourself a drink," said Mr. Chambers as he chuckled. "The main bar is in the living room, but there's also a bar downstairs in the basement."

Jack walked into the living room slowly to avoid falling in the heels. The result of his careful pace was that it gave him a rather sexy gait. His hips rolled back and forth as he walked.

Jack looked around at rest of the crowd. The imagination of his co-workers amazed him. Everyone had a great costume. They were all dressed as a variety of lawbreakers, ranging from common criminals to famous people, such as Richard Nixon and Michael Jackson. One woman from his department was dressed as Martha Stewart, and she even had an ankle tracking device on.

The criminals far outnumbered the lawmen and women. Greg from Jack's office was dressed as Robocop. Another co-worker was doing a killer Dirty Harry imitation. Jack was glad that he had come. He now had a totally different view of his fellow workers.

Jack worked his way through the crowd towards the bar. No one recognized him, even people from his own department. He was getting quite a kick out of this. He then saw Tomas standing in front of him. Jackie walked over and ran his hand across the side of Tomas's face.

"You looking for a good time?" he asked in his best sexy voice.

Tomas turned around and stared at him. He had seen Jack earlier, and was now totally shocked when Jack's voice came out of the woman he had been previously leering at.

"Holy Shit! Is that you Jack? - or should I say, Jackie?" asked Tomas, who was dressed in a white suit and silk shirt. He was holding a very large toy machine gun labeled "My Little Friend."

Jack just nodded.

"You make one fine looking whore," stated Tomas, his accent becoming very heavy. "Can I get jo a drink, beetch?"

Jack laughed. "Thanks, Tomas, I'd appreciate it."

"What did old man Chambers think of you?" whispered Tomas as they walked towards the bar.

"You mean the Godfather? He loved it," replied Jack.

"Cool, if you went to all the trouble of looking like that, I'm glad you made points with him," said Tomas.

"Allow me," interrupted Chris as he handed Jack a glass of champagne.

"Hi, Chris," stated Jack.

"I saw you when you came in, otherwise I would have never known it was you," said Chris as he eyed Jack.

"It's a great costume, you should definitely win first prize tonight" concurred Tomas. "Hey, there's my wife; she's got to see you." He waved towards a woman who was also dressed like a prostitute. "Selena, come here."

"Looks like we're in the same profession," said Jackie, as she was introduced to Tomas's wife Selena.

"Yes, so who is your pimp, or are you an independent worker?" she replied with a laugh.

"Pimp? I don't need no stinkin' pimp!" replied Jackie.

"You go girl," replied Selena with a laugh.

"Honey, this is my co-worker, Jack, or should I say Jackie," introduced Tomas.

Selena's eyes opened wide. "So, you're the new guy. Great costume, did you do it all by yourself?"

Jack shook his head. "No, I went to a service."

"Well, they did a great job," commented Selena as she ran her eyes over Jack.

Jack's outfit was the hit of the party, and he fooled more than one person that night. He didn't even mind that everyone was calling him Jackie. Screw it, why not play a girl for the night? he thought.

Halfway through the evening, Mr. Chambers made the announcements concerning the best costumes. Not surprisingly, Jack won for best overall. His prize was a gift certificate for one of the better restaurants in the city.

Jack was very pleased with himself and also liked the attention he was getting. To his surprise, he actually got hit on, even after he made it clear he wasn't a woman. He shrugged this off as a result of alcohol. Still, he felt a strange feeling of satisfaction knowing that he was seen as an object of desire. In fact, as he let his thoughts come more openly, he found it all strangely arousing.

The idea that men found him sexually attractive wouldn't leave his mind, and he wondered what it would be like to be kissed by a man. He had never thought about being with a man before, but his mind began to rationalize these new feelings. He wasn't a man tonight, he was Jackie, and if a man found him attractive did that make him gay? It was no longer black and white, and these thoughts would have been hard to figure out even if he was completely sober.

When he had to go to the bathroom, he found himself staring at his reflection in the mirror. He smiled at how feminine he looked, and as he carefully reapplied his lipstick, he felt a strange warm feeling of pleasure sweep through his body. He looked at his image and shook his head, more out of disbelief than displeasure. He loved the way he looked.

"This is just a costume; there is nothing wrong with doing this," he stated aloud, as if to convince himself. He stared at his painted eyes and realized that he didn't believe himself. He let out a sigh and then remembered to apply his lip gloss before leaving the bathroom.

Jack also noticed that the women at the party treated him differently. It was weird, but they seemed to treat Jack as one of them. His attempts to hit on one woman, Lisa, who also worked in his department, were sloughed off with a laugh.

"Please, Jackie, while I've always been slightly curious about trying it, I don't go that way," she said with a giggle. She was dressed as a 1930's gun moll. "What we need to do is find you a nice boyfriend or a pimp."

As Jack got into the full mood of the party, he drank a little too much, and while he wasn't drunk, he knew he couldn't drive home. He sat down on one of the couches in the basement and tried to clear his head. He was also sad that the evening was coming to an end; in some ways he didn't want his night as Jackie to come to an end. He was so lost in his thoughts that he never noticed Chris walk up to the couch.

It was no coincidence that Chris found Jackie. Throughout the evening, Chris had discovered that he couldn't take his eyes off the now transformed Jack. He'd positioned himself to observe her undetected throughout the entire evening and was impressed by how feminine she acted.

"How're you doing, Jackie?" asked Chris, as he sat down on the couch.

Jackie looked up slightly surprised, but at the same time pleased to see Chris. "Hi, Chris, I'm tired. I'd like to go, but I don't want to risk driving home, especially dressed like this," replied Jackie with a giggle. "I was thinking of calling a cab. However, I left my cell phone at home, and the last thing I want is for Mr. Chambers to see me drunk."

"I'll give you a lift. You can always get you car tomorrow. Mr. Chambers doesn't mind; in fact, he'd rather you catch a ride. A lot of people leave their cars here at his parties."

Without giving it much thought, Jackie nodded. "Sure, Chris, that sounds good."

"Great, come on," said Chris. He stood up and gently helped Jackie stand up. He then escorted Jackie outside.

Jackie felt a shift in his persona, make that her persona. She would be Jackie for the rest of the evening and enjoy her time as a woman.

When they reached Chris's car, he opened the door for her. Jackie just smiled and got in. Why not play along? she thought. She felt a wave of excitement sweep through her, as if she was doing something naughty. What damage could come from it, she thought. Chris knew she was really a guy, so this was just harmless fun.

Chris got in the car and they headed out.


Chapter 8


"I noticed you got a lot of attention at the party," commented Chris.

"Yes, I was even hit on a few times," replied Jackie. She felt free to talk to Chris. "I was even hit on by a few men who knew I'm a guy. I guess I should take it as a compliment." She tried to sound as if she was upset by this; rather than that, she was just mildly amused.

"I can understand why they hit on you. You look sexy, but it goes beyond that; you're something exotic. For some of the men, your being a male yet looking like a very sexy woman, allows them to indulge in a sexual fantasy and rationalize that they aren't gay."

"You mean that they were serious?" asked Jackie. She was both intrigued and shocked. Did Chris sense the feelings that were bubbling up in her?

Chris glanced over and nodded. "Very serious."

There was a look in his eyes that was different. Jackie turned away and looked out the window, so that Chris wouldn't see that she was blushing.

"I see this has touched a nerve with you," said Chris, as he reached over and gently placed a hand on her shoulder. "You want to talk about it?"

Crap, she wasn't fooling him, she thought. Jackie bit her lip. "Okay."

"Good. Let's go to my place," replied Chris.

Jackie sensed that he wasn't asking her permission, and for some strange reason it really didn't bother her.

They drove to his condo and parked the car. Jackie looked outside and wondered if this was the right thing to do.

"Come on, I won't bite," said Chris as he got out of the car. He slipped his fedora back on and ran his hand across the brim; he then walked around and opened the door and helped Jackie out. "I'll treat you right, doll face."

Jackie was about to protest, but instead she just played along. She giggled at Chris calling her doll face. Still, a strange feeling ran through her body as Chris walked her up to his place. He had his arm around her waist and was obviously taking control of her, and yet she didn't mind.

She was so lost in her thoughts that she stumbled slightly and would have fallen if Chris hadn't been holding her.

"It's a good thing you didn't drive," said Chris with a chuckle.

Jackie giggled. "Thanks."

They walked inside and Chris turned on the light. It was a nicely furnished condo. The living room had a large couch facing a gas fireplace. A large flat screen TV was mounted above the fireplace.

Chris took Jackie's wrap. "Have a seat. I have a nice bottle of red, would you like some?"

Jackie nodded. "That would be nice." She continued to look around the room. There were landscape paintings on the wall. There was a sliding glass door leading out to a deck. She could see the reflection of the river in the distance. The view from her loft was of a Chinese restaurant.

She began to wonder if this was the right thing to do. Did he just want to talk, or was he coming on to her? What was even more curious was that she didn't mind if he did. It was like she was becoming a new person. She nervously ran her tongue across her lips and wondered if she should touch up her lipstick.

Damn, I shouldn't have drunk so much, she thought. This is so stupid, but deep down she knew that she had been drunk many times in the past and had never lost control. It was obvious that she wasn't being forced into anything as her repressed feelings awakened.

Still, if she was to be with a man tonight, Chris was a nice choice. He was very handsome and very masculine.

Chris walked over to her; a comforting smile was on his face. She then realized the smile was for her as he handed her a glass of wine. He set his glass down on the coffee table and turned on the fireplace. He then turned out the lights so that the only light was from the fire. Jackie noticed how smoothly Chris had done this. So, this was what it was like to be seduced, she thought.

He sat down next to Jackie and picked up his glass. "Cheers."

Jackie smiled back and touched her glass against his. She sipped the wine. It was a very good vintage. She closed her eyes and smiled in pleasure as its warmth filled her body. "That's so nice," she sighed.

"So, do you want to talk about it?" asked Chris.

Jackie took another long sip of her wine. "Is it that obvious?"

"To those of us with insight," replied Chris. "I watched you this evening, and with each passing moment I saw the real you emerge. I'm beginning to feel that Jack is the costume."

"It's rather confusing. I never had feelings like this before. I mean... I don't see myself as a hooker or anything like that, but being seen as a woman, felt... well... it feels nice."

"You've never wanted to be a woman before tonight? I find that hard to believe. Look, Jackie, you can be honest with me. I don't mind if you want to a woman."

Jackie looked into his eyes, and to the best of her ability she could see that he was being truthful.

Chris smiled. "And you liked the attention that the men gave you?"

"I guess," she replied and nervously sipped more of her wine.

"You guess?" he asked.

"Okay, okay, I'll admit it; I liked it. I've never had a homosexual thought before in my life, but I liked the fact that some of those men looked at me in a sexual way. It's very confusing."

"You still haven't had a homosexual thought, my dear. You're reacting as a woman, not as a man," interrupted Chris. "Don't try to see this in a logical manner. Yes, you've seen yourself as a man, but you now know that you have a strong female side, right?"

Jackie nodded.

"And you're finding that you like it, right?"

"Yes," replied Jackie.

"You like it more than being a man, right?"

She began to tremble slightly, more out of anticipation than fear. "Yes, you're right."

"Good, so tell me more about this evening. Tell me about how you felt around those men tonight," asked Chris.

"I liked the way they were treating me," continued Jackie. "It wasn't like they were treating me as they did back in the office...."

Chris nodded. "You mean how they tried to take control? You liked how they tried to dominate you, right?"

Jackie looked up into Chris's eyes. "How did you know that?"

"I've sensed a submissive side in you since I first met you. Deep down, you crave control; this doesn't mean that you want to be someone's slave, but you want someone in your life to make decisions for you," explained Chris. "I know this because I need to be in control."

"Really?" asked Jackie.

Chris smiled, and he leaned over closer to her. "You're a very sexy woman, Jackie."

Jackie tried to speak, but couldn't.

"No, don't say anything," said Chris as he stared into her eyes. "I've always sensed there was something different about you, but I had no idea that such a beautiful woman was inside you waiting to escape."

Jackie's mind was a whirl of thoughts. She tried to tell herself that this wasn't happening, but at the same time a stronger feeling was overriding these thoughts. She wanted to be with Chris. She had never felt this way about a man before, but now that her female side had been unleashed, she couldn't help herself.

"As I watched you this evening, I knew I had to be with you, to turn you into my loving woman. You want to be my woman, don't you?" asked Chris. "If you don't, I'll take you back to your place right now, and nothing else will ever be said about this. It will be as if it never happened. Do you understand?"

Jackie nodded.

"So, what do you want? Do you want to stay?" he asked softly. "This is a big step, and I don't want to force you into something you might regret later."

Jackie stared back at Chris. Her mind was a whirlwind of thoughts and feelings. Yes, he was trying to control her, but she had an out, all she had to do was to say no and this would end, but she didn't want it to end. She was tired of repressing her true feelings, and she so badly wanted someone to love her.

"What do you want, Jackie? Do you want to stay with me?" he asked.

Jackie nodded slightly.

"Tell me that you want to be my woman," ordered Chris. His voice was forceful but loving.

"I... I want to be your woman," said Jackie softly.

Chris smiled and nodded. "Good. Tell me your name."

"I'm Jackie," she replied. Her breathing was getting heavier.

"That's right, and you're my woman. You belong to me now."

Jackie nodded, unable to take her eyes from Chris's eyes.

"Say it, Jackie," ordered Chris.

"I belong to you; I am yours."

Chris nodded and ran his hand gently across her face. He gently eased her face up so that he could look into her eyes. "I will mold you into my woman. I will treat you as the woman you were meant to be. I know this is very new to you, but deep down you know this is the right path for you."

Jackie found this to be very appealing, and she could feel herself surrendering to Chris. She felt strangely submissive and passive next to Chris, and she desired him to take even stronger control of her. He was right; she wanted to be controlled by him.

"You won't have a thing to worry about. I will take care of you, and all your needs will be met. Do you find that appealing, my sweet?" asked Chris.

Jackie nodded and let out a long breath.

Chris leaned over and began to kiss her. He pressed his lips tightly against hers, and his tongue slipped into her mouth. Jackie offered no resistance and just kissed him back. There was a small part of her mind screaming out that this was wrong and that she was really a man, but it was drowned out by the waves of pleasure that swallowed her.

He pulled down her dress and began to rub her nipples. No one had ever done that to Jackie before, and she was shocked by the waves of pleasure that began to run through her body. As Jack, she'd had sex many times, but this was totally different. It was so overpowering.

Jackie felt Chris's strong hands guide her head down into his lap. She watched in anticipation as he unzipped his pants and pulled out his hardening cock. She instinctively licked her lips and began to kiss and lick it. Something deeply repressed came out of Jackie's mind, and she knew exactly what to do to pleasure her man. She remembered how women had given Jack oral, and she tried to duplicate their actions.

Soon his cock was filling her mouth, and she began to bob up and down on it; the sounds of pleasure coming from her lover only served to quicken her pace. Chris's hands were now gently guiding her head up and down on his cock. He wasn't forcing himself on her; rather he was guiding her, directing her into the path that he had decided for her.

"Oh, yes, Jackie, that's it; show me that you're my woman," moaned Chris. "Show you know how to pleasure a real man."

Jackie worked his cock until she could feel that he was about to climax. The idea of giving head to a man had never entered her mind before, but then again she hadn't unleashed her female side before. Instinct won out over logic, and soon Jackie was swallowing Chris's cum.

"That was fantastic," stated Chris as he pulled her close to him. "You're truly a woman now."

Jackie sat up next to Chris, and he pulled her close to him. "I think we should go to my bedroom, our bedroom, Jackie. Would you like that?"

Without hesitation, Jackie nodded.

"Are you willing to be mine, completely?" asked Chris.

"Yes," replied Jackie.

"Tell me that you want me to make love to you," ordered Chris.

"Please, Chris, I want you to make love to me. Make me your woman."


Chapter 9


Chris escorted Jackie to his bedroom. There was a large king-sized bed, and he sat down on the end and positioned Jackie in front of him. He pulled her dress down her body and had her step out of it. Next he removed her bra. He leaned over and kissed her nipples. Lastly, he had her remove her boots.

"Leave the rest on," he ordered.

He then undressed and pulled her onto the bed with him.

"Do you want to take this to the next level; do you want me to make love to you?"

Chris had taken her too far for her to stop now, and she smiled back at her lover. "Yes, I want to know what it's like to feel you in me," she replied.

Chris began to kiss her again, pulling her body close to him, his cock beginning to harden again in anticipation of entering his new girl.

Jackie responded to Chris's actions and was soon caught up in the passion. It was just supposed to be a party, and now she was about to make love to her supervisor.

She smiled to herself as she slipped her panties down, and she remembered how Tess had made sure that her garters were on the inside.

He moved her around and began to gently rub lubricant between her legs.

"I'm going to be gentle with you, my sweet," he whispered as he began to rub the lubricant against her hole.

Jackie just moaned back and offered no resistance. She could feel Chris's fingers begin to enter her. The slippery lubricant was now being worked into her body, preparing it for Chris's cock.

"I want to look at you when I enter you," whispered Chris. "So I'm going to lie on my back, and you're going to face me and take my cock in your ass-pussy."

Jackie moaned out what sounded like a yes.

Chris watched as she began to lower herself down on his fully erect cock. Her eyes opened wide as she slowly took him in. She accepted him into her body and moaned in pleasure. Chris reached up and began to rub her nipples. He couldn't wait until the hormones began to flesh her out. He caught a quick look at Jackie's small but erect clitty, he had plans for that too. He wanted her to keep it, but between the hormones and other things, she would accept it as her clit and not a cock.

Jackie began to lift up and drop down as she rode Chris's cock. She had no idea it would feel as good as it did. She was being fucked, and she loved every second of it. Her moaning got louder and more frequent, grunting and groaning with each stroke of Chris's cock into her pussy. I have a pussy, she thought as he made love to her.

Chris pulled her tight as he came into her. Shot after shot of cum went deep into her pussy. He then pulled her down next to him and began to gently kiss her. "You're now a woman for real. There is no going back."

"It was wonderful," gasped Jackie. "I came at almost the same time you did."

"Of course you did. You loved it, didn't you?" he asked.

Jackie turned to him and smiled. "Yes, it was wonderful. I had no idea it would feel like that."

There was a long pause as they lay there soaking in the moment.

"Do you want to stay a woman?" he asked as he kissed her.

"Oh yes," she replied, as she cuddled next to him.

"You may have to dress as a man for a while, but with each day I will make you more and more a woman," he said.

Jackie looked at him. "I'll do as you wish."

"I know you will, my sweet. Now, you'll keep your body smooth from now on. I like how you trimmed your pussy hair. Keep it like that," he said.

"I will," replied Jackie.

"Keep the polish on your toe nails too. It looks so cute," continued Chris. "Also, I want you to only wear panties from now on. I'll buy you some more this weekend."

"Okay," replied Jackie.

"Tell me, who did your makeup for tonight?" he asked.

Jackie told him about Tess and her offer.

"Good, that's exactly what you need. I'd like you to call her tomorrow and set up a schedule to start your training. She sounds like the perfect person to help you become a total woman. Don't worry about the cost either. I'll take care of that," said Chris.

"I do have some money," replied Jackie as she stifled a yawn.

"That's nice, my dear. Now how do you feel about hormones?" continued Chris. "I want to see your body with a woman's curves and softness."

"I'd like that, but what about work?" asked Jackie.

"For now, you should go to work and do your job. When you get home, you'll change back to Jackie. We'll decide how and when you give up your job and move in with me fulltime."

Jackie nodded. It was so complicated, and there was so much to do; she was happy that Chris would be making all the decisions.

"I also want you to make some changes at your apartment. Since a woman will be living there, it should look that way," he stated. "But that can all wait until later.'

He pulled her close and kissed her. She was soon fast asleep in his arms.


Chapter 10


Chris was up early and looked at Jackie sleeping soundly in his bed. He couldn't believe his luck. He had always craved a submissive mate. He'd tried to be with someone who wasn't submissive, and it just never worked out. He needed control and craved a partner willing to submit to him.

As Chris had long stopped worrying about labels such as gay or straight, the gender of his lover wasn't totally important to him. Even though deep down he preferred female or transgendered, the attitude of obedience was more important.

He had had his eye on Jack for a while, but this was far better than he could have wished. It was obvious to him that Jack had a strong submissive streak. Still, he'd never imagined that Jack would show up at the party en femme.

Chris thought about the numerous times he had given Jack an opportunity to leave last night, and she had decided to stay. It was a key point for Chris that his partner enter the relationship of his or her own free will. The idea of forcing someone was totally repugnant to him. No, he wanted someone willing to surrender control because they wanted to, not because they were forced.

When he'd seen Jackie at the party, he knew he had to have her. Unlike some of the other men dressed as women, Jackie looked too feminine, too perfect in her looks. She'd acted as if she had been born female.

Chris had watched her the entire night and was pleased when she actually responded to the flirting of her co-workers. He knew that he had to make his move that night and hope that his instincts weren't wrong.

He smiled, thinking how feminine Jackie had acted in bed, and how she had allowed him to fuck her with no protest. He stared at her sleeping form again and smiled. Jackie, you're now my woman, he said silently to himself.

Still, he sensed that Jackie was dealing with some huge issues and as much as he wanted her, he also wanted her to be happy. He would have to be careful to nurture her and help her find her way.


Chapter 11


Jackie awoke the next morning alone in Chris's bed. She could smell the aroma of fresh coffee brewing. She felt sore over her whole body, although it was a good sense of discomfort. The events of the previous night replayed in her mind. There wasn't a single thing she'd done that she regretted. She had never known that sex could feel so good.

She stepped out of the bed and walked into the bathroom. She had to admit that she looked awful. Her wig was crooked, and her makeup was a total mess. Tess had put some makeup in her purse, and Jackie wondered if she could make herself look like a woman. She had some experience with makeup, but that was a long time ago, back in her high school theater. Still, it was a worth a try.

She opened the purse and found some foundation, eye shadow, blush, mascara, and lipstick and gloss. She found herself licking her lips, thinking how good it felt to be kissed by Chris.

Jackie took a long hot shower. She ran her hand across her face and could only feel a little stubble. She borrowed Chris's razor and returned her face to being smooth.

After drying off, she put the wig back on. There was way too much hair, but she solved this by pulling it back into a ponytail. All she needed was something to keep it in place. She opened the drawers below the counter and found a woman's scrunchie. It was just what she needed. Even with the hair pulled back, she looked pretty feminine.

She then applied her makeup. She tried to remember what Tess had done the previous night. She knew she had to tone it down a lot, and after some experimenting, she did a passable job.

It then hit her that she didn't have a daytime outfit. The dress and boots from the party were hardly something she could wear outside. She shrugged it off and figured Chris would figure something out.

She walked out of the bathroom and found several items of women's clothes laid out on the bed. There were several tops and skirts, along with a pair of jeans. Her bra, corset, and panties were lying next to the clothes.

Jackie smiled and put on her panties, bra, and corset. She put her bra on and was able to reproduce the magic that Tess had done yesterday. She looked down at her small breasts and wondered what it would be like to have much bigger ones.

She then picked up a dark brown top and tried it on. It was a little small in the chest, but that only served to show off her breasts. The jeans were way too tight, so she tried on one of the skirts. It was a short denim one. It was a close fit, and Jackie had to admit that she looked pretty good as she checked herself out in the mirror.

Chris was sitting at the counter of his kitchen, drinking coffee and reading the paper. He smiled as he saw Jackie approach. He motioned her over and gave her a long passionate kiss.

"Very nice. I think that you should always wear short skirts and dresses; you definitely have the legs for them," he commented.

"Okay, if it makes you happy," replied Jackie. "Where did the clothes come from?"

"An old girl friend left them here," replied Chris. A small smile grew on Chris's face as he saw Jackie's willingness to please and obey him. He would only build upon this foundation and make her into his perfect lover. Still, he had to let her know what he wanted. He poured her a mug of coffee and handed it to her.

"Jackie, are you sure you want to do this? Now, before you answer, I want you to consider how this is going to totally change your life."

Jackie sat down on the stool next to Chris. "I understand fully."

"I seriously doubt that, Jackie. Look, I want a loving and submissive woman. I want a woman like you."

"You mean a woman who was once male?" asked Jackie.

"Exactly. I want to make you very feminine, but I want you to keep your clitty. Now, it won't function like it does now once you start taking hormones; it will still be sensitive, but it won't be as big or as hard."

"Go on," said Jackie.

"The hormones should also give you breasts, but what nature fails to provide will be taken care of by implants. I also plan on having you get some work on your face," said Chris.

Jackie's hands went up to her face. "What will you change?"

"I'd like you to have a slightly smaller nose, and some higher, more distinct cheekbones. It will make you look very feminine and sexy," explained Chris.

"Obviously, you've been thinking about this all morning," replied Jackie.

Chris nodded. "Actually, since last night. I also want you to get pierced."

"You mean my ears?" asked Jackie.

"Along with you clitty," he replied.

"My clitty?"

Chris nodded. "A small ring through the head. It will make it very sensitive, and it will also be a reminder that you're not a man anymore. It has one other side effect; it will force you to sit down to pee, otherwise it makes it rather messy."

Jackie nodded and giggled. "Okay."

"You'll also need to get some hair removal. We'll look for a good laser removal service; I've heard it's better that electrolysis."

"This all sounds very expensive," she said.

"Don't worry about it," remarked Chris. He reached over and took her hands into his. "Money isn't the issue; I just want to make sure that you're doing this willingly."

"Thank you, but I want to do this too. Something happened last night, even before you brought me here. I felt a change as soon as I saw myself at Tess's place. I told you about my past and how I was shuffled from one family member to another, but I downplayed how harsh it was. In many ways, my life stopped when my parents died. I put all my efforts into getting a good job, so I wouldn't have to depend on other people. I blamed my partners for our failed relationships, but looking back, I know it was all my fault."

"You mean you didn't feel that you were female when you were younger?" asked Chris.

"I don't know, I just knew I was different, but I refused to allow myself to be distracted. It goes back to when I was very young. Anyway, after my parents died I repressed it. Well, I did allow myself one distraction; I was in theater in school," explained Jackie.

Chris wanted to ask more about her parents dying but decided to wait until later. "Did you ever play a woman?"

Jackie shook her head, her ponytail swinging back and forth. "No, even though I had the opportunity to do so. I did take the more outrageous roles, the ones that involved lots of makeup and dressing up, but never female. Looking back, I guess I was in full denial."

Chris laughed. "Looking at you right now, I would say that was a major understatement."

Jackie joined in the laughter. "I guess I did a pretty good job of fooling myself. You saw through me at the party, I wonder if others did too."

Chris picked up his coffee mug and took a sip as he nodded.

Jackie's eyes opened up wide. "You mean that?"

"I was talking to Tomas and Selena. They commented how naturally feminine you acted."

"Tomas knew?" asked Jackie.

"And Selena too."

"Anyone else?" asked Jackie.

"Mr. Chambers."

Jackie stared back at Chris. Her face was suddenly very serious. "What did he say?"

Chris reached over to comfort her. "It's okay. He just suggested that it looked like some day soon I would have another woman in my department. I asked him what he meant, and he pointed at you. He said that should the issue arise, you had nothing to worry about. The company has a non-discrimination code that covers the transgendered."

"It was that obvious?" Jackie was shocked that so many people, including her boss, had seen her as female.

"Honey, your female side took over last night; all those years of repressing those feelings came out. Granted, the acceleration was lubricated by many glasses of champagne, but the real you came out last night. While I love the fact that you have a masculine side, I know for a fact that I made love to a woman last night." He leaned over and kissed her again.

"So, I would be accepted at work as a woman?"

"I don't see why not; hell, most people at work barely know you anyway," remarked Chris. "You know, I like the idea of seeing you at your cubicle in a dress."

Jackie giggled. "I don't have a wardrobe yet."

"That's easy to solve," answered Chris. "We'll go pick up your car and then go shopping."

"You're serious, aren't you?" asked Jackie.

Chris shrugged his shoulders. "Sure, why not? Look, I don't expect you to go to work Monday as Jackie, but in a few months, after you've grown more comfortable as a female, why not?"

Jackie smiled at Chris.

"That woman who helped you dress for the party, what was her name, Tess? Well, I think you should call her and set up some appointments to help you change."

"I don't know, this is happening so fast," sighed Jackie.

"Like last night?" he asked with a raised eyebrow.

"Point taken," she giggled.

"For now, as far as work goes, we're just friends. However, everywhere else from now on, you're my girl."

"I like the way you say that," cooed Jackie.

Chris began to kiss her again. "You are my girl. I do want you to know something, Jackie. You can talk to me about anything at anytime, and if you don't want to do something, I want you to let me know. Promise me that."

Jackie just nodded.



Chapter 12


They arrived together at Mr. Chamber's house.

"What do I say, how do I explain the fact that I'm still dressed in women's clothes - crap, make that DIFFERENT women's clothing?" asked Jackie in a panicky tone.

"Just tell him that you're really transgendered, and that it was just easier to come back here dressed as you are. You can tell him that you'd like to eventually transition at work," stated Chris. "Remember, he kinda figured it out last night; I doubt he'll be surprised."

"I don't know," replied Jackie.

"I'll be there. I'll let him know that you came to me and told me that you're TG," said Chris, as he slipped his arm around her. "Relax, sweetie, everything will be okay."

They were soon sitting across from Mr. Chambers. To Jackie's shock, he didn't seemed that surprised that she was there. He then allowed her to explain her situation.

"I promise you, Ms. Easton, that this in no way will affect your career," said Mr. Chambers. "When you're ready to transition at work, let me know in advance, and I'll talk to the company. There are some personnel issues that will have to be worked out, but we have time to talk about those later."

"Thank you, sir," replied Jackie as she looked at Chris who was nodding. "I know this is rather sudden, and I want to thank you for being so understanding."

"There's no need for you to apologize. I saw you at the party, and there was no denying that you're female. I guess the prize should have gone to your costume as Jack while at work," he replied.

"I promise not to let you down, sir," replied Jackie. "This won't interfere with my job. I promise to work just as hard as before, and I won't slack up after the change."

"I know you won't, Ms. Easton," he said. He then leaned back. "I haven't always been this open-minded. It took my youngest daughter coming home from college with her girlfriend to cause my attitude to shift. If I could accept my daughter, then what was the big deal with my employees? It's their lives, why should I care? I do know that I want you to keep working for me, and if you feel more comfortable as a woman, then who am I to argue. I will tell you one thing, Ms. Easton; I will hold you to the same standards as I would any other employee."

"I won't let you down," replied Jackie. There was no turning back now, she thought.

Chris was thinking the same thing. This had turned out even better than he could have hoped. Jackie was now locked into her transformation. He felt his cock start to harden as he thought of her now living all the time as a woman.

"Now, not to press too deeply into your private lives, but can I deduce that you two are more than just friends?" asked Mr. Chambers.

Chris nodded and took Jackie's hand into his.

Without a show of emotion Mr. Chambers nodded. "Well, I had planned to tell you this later, but it might as while be now. Chris, I've been looking for a new department head for the new product division, and I can think of no one better than you. This will also split you two up and avoid any interdepartmental issues," he continued. "The change won't happen for a month, but I can count on you two not to do anything stupid, right?"

Chris and Jackie nodded.


Chapter 13


Chris followed Jackie to her apartment. He wasn't totally surprised by the events at Mr. Chambers' house, but he was definitely pleased. It was best that he wouldn't be directly supervising Jackie at work, as it might cause some problems with his domestic plans for her. Besides, the promotion would mean more money to use in Jackie's transformation.

Chris parked on the street and walked over to Jackie.

"I'd like to see your place, if you don't mind," stated Chris.

"Sure, but it isn't much," she replied. "It's sort of small."

"I don't mind," he replied.

Her place was quite small, he noted, which was good as it would be easier to feminize. The furniture was neutral, and it wouldn't take much to make it look as if a woman lived here. He made some mental notes on things to feminize Jackie's place.

Meanwhile, Jackie was calling Tess.

"So how did the party go?" Tess asked.

"It was great, but...."

"Let me guess, your female side took over," interrupted Tess.

"How did you know?" asked Jackie.

"I saw it in your eyes. Jackie, I've been dealing with the transgendered community for years, and I knew the moment I met you that you were TG. So how can I help?"

Jackie explained about her circumstances at work and with Chris.

"Damn, you didn't waste any time did you? Transition at work and a boyfriend out of one party - girl, I definitely need to party with you," stated Tess.

Jackie laughed. "So you'll help me?"

"I wouldn't miss out on it. Just tell me, how did you like it - I mean being with a man?" asked Tess.

"It was wonderful," stated Jackie, looking over at Chris

"Hmm, well, when we meet next I want details! So when would you like to see me next? I have openings tomorrow and Monday," said Tess.

"Both days. I need a whole new wardrobe and have to learn to do my makeup. This is happening so fast."

"I've seen it before. A guy comes in and dresses for the first time; a week later he's dressing fulltime. It just proves that repressing feelings doesn't make them go away; it only builds up and explodes like a volcano. "

"What time can I see you tomorrow?" asked Jackie.

"Well, I'd like to spend it on working on your makeup and looks. We can go shopping Monday when you get home from work, that way you won't have to deal with weekend crowds. So come over at noon tomorrow, if that's okay," replied Tess.

"How much will it cost?" asked Jackie.

"Since we'll be seeing each other quite a few times, how about two hundred a session, plus expenses," said Tess.

"That sounds fair," replied Jackie.

"Okay, see you tomorrow, Jackie."


Chapter 14


"Where are we going now?" asked Jackie. She was sitting next to Chris in his car.

"We have to get you your next wardrobe. I know you'll be shopping with Tess, but I want to select part of your new look. There are some other things we need to do," stated Chris.

"I can't believe how fast this has all happened... still, it's too late to turn back now," replied Jackie.

Chris nodded and thought to himself, and soon it will be even more difficult, if not impossible.

First, Chris wanted to expand Jackie's wardrobe, and then get rid of most of her old wardrobe. He would leave her enough to function at work, but the rest of the time he wanted her en femme. They stopped at several boutiques and shoe stores.

Chris wanted Jackie to be dressed in sexy outfits as much as possible. Items that would make her feel as feminine as possible. Yes, he allowed her to get some casual everyday outfits, suitable for going to the grocery store or things like that, but for going out she would be in revealing, ultra-feminine outfits. He also bought her several pairs of high heels, and more high-heel boots. He got aroused watching Jackie struggle to walk in four inch heels, but even as she struggled, she didn't give up, and that especially pleased Chris.

They also picked out a lot of lingerie for Jackie. Chris knew a woman who made real corsets, and he planned to call her that week and get Jackie fitted for one. The store-bought one she had for the party was fine for now, but he wanted her to have a genuine corset to wear. The corset would serve two purposes; one, it would give her a sexy figure, and two, it would be another way to control her.

They also stopped at a hardware store, and Chris had some keys copied. He gave Jackie a copy of his house key and had a copy made of her key for himself.

"So where are we going now?" asked Jackie.

"It's time to get your ears pierced," replied Chris.

Jackie nodded and smiled when Chris reached over with one hand and took her hand. "That is okay at work, right?"

"Yes, men can have pierced ears," he replied. He pulled her closer. "You okay?"

"Oh, yes. It's just happening so fast. Still, it's a little bewildering. I mean, yesterday I was just a guy working in an office, barely knowing anyone in town. Now, I'm the girlfriend of my ex-supervisor, being whisked around town, being treated like a princess. It's all pretty amazing."

"Any regrets?" he asked.

"No, no regrets."

Chris smiled.


Chapter 15


"Okay, Jackie, you'll need to keep those studs in your ears for several weeks before you can start wearing more stylish earrings," explained Mona, the woman who had just pierced her ears.

Jackie looked at her ears in the mirror. They each had one gold stud. She reached up and touched them. They were upstairs in a piercing salon. She didn't know it, but when she went fulltime, she would have multiple piercings in each ear, but those would have to wait for now. Chris was downstairs in the main store. It sold high end leather outfits and toys for the S&M crowd.

"Also take care to make sure they don't get infected. I've enclosed instructions in with the disinfectant in this bag," continued Mona. "I've also enclosed some information on body piercings; your boyfriend said you were interested in getting one."

Jackie turned and smiled. "Yes, I am."

"Does he like oral?" asked Mona with a grin.

Jackie nodded.

"Get your tongue pierced. Men love the feel of the stud against their cock," said Mona, as she stuck out her tongue, showing off her own stud.

"I'll ask him if he's interested," said Jackie.

"Is he your Master?" asked Mona. "You have the demeanor of a slave."

Jackie was taken back by this observation. "No... I'm not his slave... but he's definitely in charge."

Mona laughed. "That's pretty obvious, hon, you're very submissive - too bad you're taken, or I might have tried to get you. I love women like you." She then stared deep into Jackie's eyes.

The look scared Jackie. It was obvious to her that Mona was dangerous. She didn't know what to say and could only stare back and tremble slightly.

"Oh, you're precious. Damn, why do I always meet girls like you once you're taken? I could have so much fun with you!" stated Mona, followed by a laugh. "Oh, yes, it wouldn't take much to turn you into a sweet little slave girl. You'd make such a delicious pet." She then licked her lips slowly.

Jackie could feel Mona's power, and it frightened her deep into her soul. She eventually was able to look away.

"So, have you started hormones yet?" asked Mona.

Jackie shook her head nervously. "No, not yet. How did you know that I was going on hormones?"

"It's obvious that you were meant to be female. I'm sorry; I didn't mean to embarrass you, my emotions and desires often get the best of me. You pass very well. I doubt I would have made you on the street, but up close like this, I can tell that you were once a man. Seriously, you pass very well."

"Thanks," replied Jackie.

"You have any other questions?" asked Mona.

"Do you do all the piercings here?"

"Most of them," replied Mona. "I sometimes do them at parties and people's homes."

"So how long does it take for a piercing to heal?"

"Where?" asked Mona with a grin.

"My co.... clitty," said Jackie in a soft voice.

Mona nodded. "Usually four to six weeks. It sometimes heals faster. Does your boyfriend want you to get one?"

Jackie nodded.

"That makes sense. It's a pretty easy piercing and, while it will hurt, the pain passes pretty fast. I think it'll look nice in your clitty," replied Mona. "If you want, we can do it right now and surprise him."

Jackie debated this. Chris had done so much for her, and he did want her to get one. Still, she wondered if she should get his permission. "I don't know."

"He wants you to get one, doesn't he?" asked Mona.

Jackie nodded. "He said that it would make me feel more feminine."

"Well, I can do it in less than ten minutes if you want," offered Mona.

"I'd like him here while it's being done," said Jackie as she began to stand up.

"Sit down, I'll call downstairs and have them send him up here," said Mona.

Chris was up there in a few minutes. He was very pleased when Jackie asked him if she could get the piercing. He had laid the groundwork back in bed, and was glad she had made the decision herself.

"Yes, I'd like that very much," he stated.

Jackie followed Mona's instructions and was lying on her back on the examination table; her panties were off, exposing her clitty.

Mona explained what she was doing. "Now, there will be a very sharp pain when I do this, but it will pass quickly. I'll need to lock on the device before you stand up. It's called a Prince Albert, and you won't be able to take it off by yourself. If you need to remove it, come on in and I'll take it out," explained Mona.

A few moments later she nodded to Chris, who was holding Jackie's hand.

"Okay, Jackie, now relax and it'll be over in a moment," continued Mona.

Jackie felt a severely sharp pain in her clitty and partially sat up. She moaned slightly, but just as Mona said, the pain passed quickly.

"Okay, take a look," said Mona.

Jackie sat up and saw the ring through the head of her clitty.

Mona explained the safety precautions regarding the piercing. She also talked to them about other things that could be done to Jackie's body.

"I'd like to wait on getting her nipples pierced until after she's been on hormones for a while. I think we'll also wait on the tongue too. I'm not sure it would go over well in her office," said Chris. "But I do like the idea of having it done."

"By the way, are you in the scene, Chris?" asked Mona.

"No, not presently," he replied.

"Well, we have some nice parties, and I think that you and Jackie would be a nice addition," explained Mona, as she eyed Jackie with a hungry look. "Here is my card, if you're interested give me a call, and we'll talk more."

Chris nodded and placed the card in his wallet. "Thank you, Mona. I'll get back to you in a few months. Right now, we have other things to work on."

"That sounds great," she replied as she ran her eyes over Jackie. "Call me, Jackie, if you have any problems."

"I will," replied Jackie. While she wasn't upset by being ignored in the previous conversation, she was intrigued by what they were talking about.

On their way out, Chris signed a receipt and picked up a few shopping bags.

On their way home, Chris looked over at Jackie and smiled. "I'm very proud of you. Thank you for getting the piercing."

"You're welcome. I wanted to thank you for all you've done for me," she replied. "May I ask what you and Mona were talking about?"

"She runs private S&M parties. They're very safe, and they screen all potential guests. I understand she's a very well known dominatrix," explained Chris.

"Oh," replied Jackie. "I couldn't help notice that she looked at me like a lion eyes a steak. It scared me."

"TG girls like you are exotic. I can't blame her for wanting you," replied Chris. "I know that I would have done the same thing if the roles were reversed."

Jackie laughed. "So where are we going now?"

"Home," he replied. "So what did she do that scared you?"

"When she said she would turn me into her pet. Part of me found that exciting. I'm so glad that you found me first," stated Jackie.

"It's okay, my sweet, nothing bad is going to happen to you," reassured Chris.



Chapter 16


"I like this outfit the best so far," noted Chris. He was sitting on the couch drinking a glass of wine.

"You've said that about every one I've tried on," replied Jackie with a giggle. She was presently wearing a black leather miniskirt and a red silk blouse.

"Try the boots with one, I think they'll look better than the pumps," stated Chris.

"Okay," replied Jackie. She went back in the bedroom and sat down on the edge of the bed and took off the heels. The boots were black Italian leather with three-inch stiletto heels. They were expensive, but Chris had insisted that they get them. She had to admit that they were nice.

She was still a little unsteady in the heels, but she was slowly getting used to them. She also noticed how the heels made her change the way she walked, giving her a sway to her walk.

"Well?" she asked as she returned to the living room.

"Perfect," replied Chris. He then patted the cushion next to him.

Jackie sat down next to him, and he slipped his arm around her.

"How're you feeling about all this?" he asked.

"It's very different, and I'm a little worried about how I'll be received at work, but otherwise I feel very calm," replied Jackie.

"I wouldn't worry about work. The people in the office are pretty nice. The ones that don't like it will keep their mouths closed, as they won't want to get in trouble."

"What about Tomas?" asked Jackie.

"He'll be very supportive. I was at a party at their house one time and met Selena's brother and his boyfriend. Tomas seemed totally cool with that."

"But that's different - I mean, I'm changing genders," stated Jackie.

"You also work in a cubicle for most of your workday. Trust me, after a while it won't be an issue," stated Chris, as he ran his hand over Jackie's face. "Anything else bothering you?"

"Mona seemed to think that I was your slave," she said softly.

Chris laughed. "That's because that's what she sees a lot of in there. I do like my women submissive, but I don't want a slave. That's too one sided. Jackie, you're an intelligent young woman. You have spirit, and I love that about you. But I do like that you're submissive. But don't worry, I don't want to force you to do anything, and if you have objections, I want to hear them."

"Thank you," replied Jackie. She twisted slightly as if she was in pain.

"You okay?" he asked.

"The ring was pinching a little. It's okay now," she explained.

"How do you feel about getting other piercings?" he asked.

"I'm not sure. I want to see how this one feels and then decide later," she replied. "Although, Mona said that men love her tongue piercing."

"It is pretty good," noted Chris. "We can talk about that later. The main reason I wanted you to get your clitty pierced was that as the hormones take over, the ring will help you enjoy your orgasms more."

"How do we go about getting hormones?" she asked.

"I'll call the doctor Monday and make an appointment for you. They're very powerful drugs, and I don't want to risk your health," he replied.

"I appreciate that. I have to admit that I'm excited about the changes," she replied.

Chris smiled and leaned over and kissed her gently; he was pleased at how willing she was. She was the submissive woman that he had craved his whole life. He began to undress her, and his hand began to rub her nipples. He felt her hand rubbing his hardening cock.

"Let's go to bed," he whispered into her ear.

Jackie just nodded, and Chris scooped her up into his arms and carried her into their bedroom.


Chapter 17


"How long will we live apart?" asked Jackie, as she snuggled close to him.

"For a few months, I want you to live on your own as a woman; it'll help you adapt. However, you'll be spending a lot of time here," he replied as he ran his hand through her hair. "By the way, I know that you'll be wearing a wig for a while, but I hope you stay a redhead; I think you look so sexy."

"Cool, I like being a redhead," she replied. "Won't they say something about my hair growing out at work?"

"No, just keep it neat. Tess will probably be able to help you find a stylist," he replied. He then kissed her. "How're you doing?"

"I'm so happy," she replied with a sigh. "I had no idea that sex could feel this way. I love the way you feel when you're in me, it makes me feel.... well, feel like a woman. I feel like I've been reborn."

That was what he wanted to hear. While she was obviously new to having a man have sex with her, she made up with enthusiasm for what she lacked in experience. She was already becoming proficient at giving oral sex.

"How do you feel about steak for dinner?" he asked. "I pride myself on being an excellent chef."

"Okay, but I'm not too bad in the kitchen myself," added Jackie.

"Well, we'll have to try it in there sometime," replied Chris with a leer.

Jackie giggled.


Chapter 18


"Okay, so call me when you're done," stated Chris as they drove to Tess's studio.

"I will," replied Jackie. She was wearing a short, floral pattern skirt and a white sleeveless cotton top. She was also wearing three-inch-heels. It was a warm spring day, and she looked like any of the young women walking around downtown. "So what will you be doing?"

"Oh, I have a few errands to run," he replied.

They arrived outside of Tess's salon, and after kissing her goodbye, Chris watched her walk up to the front door. A pretty woman with black hair let her in, he assumed she was Tess. Jackie waved goodbye and the door closed.

Chris headed downtown to do some shopping. He wanted to get new sheets, towels, and other things to feminize Jackie's apartment. He wanted to erase Jack's presence as quickly as possible.

Two hours later, he was carrying shopping bags into Jackie's place. He got to work quickly. First he stripped the sheets and pillow cases from the bed and replaced them with lavender ones. He had also bought her some satin sheets, but he would save those for later. The comforter was also lavender. He then set a lavender scented air freshener next to her bed.

Next he went into the bathroom and replaced all the towels with new ones. He kept the lavender theme. Additionally, he hung up a thick velour bathrobe on the hook of the door.

He then went into the living area and placed some bright colored throw pillows on the tan colored couch. He unpacked several vases and set them in different locations in the room. There was a flower stand a few blocks away, and Chris had stopped there on the way to the loft. They added a very nice feminine touch to the apartment.

He then placed several scented candles throughout Jackie's home. He made sure then there were several in her bathroom. He loved the idea of her taking a bubble bath to the light of candles.

Next, Chris began to do some cleaning up. He emptied Jackie's dresser drawers of anything masculine. Other than work clothes, he left a few t-shirts and some socks, but little else. He did the same to the closet. There was a Goodwill drop-box on the way back to his place, and he would deposit the reminders of Jack there. Jack would have to wear panties from now on.

As Jackie took over, Chris would replace Jack's work shirts with blouses and his trousers with female slacks.

He looked at his watch and nodded to himself. There was plenty of time left to go to his place and get Jackie's clothes.

On the way back to his place, he got a call from Jackie. She told him that she would be done around six. This was good news, and Chris told her that he'd see her at six.



Chapter 19


Chris stopped at a furniture shop on the way back to Jackie's place. He picked out a few lamps to replace the ones in her apartment. While the old ones weren't that bad, he wanted Jackie's place to be very feminine. He already had plans to replace her curtains and artwork.

He carefully put away Jackie's wardrobe. Next, he installed the new lamps. It was a good start, he thought. He then saw a stack of magazines and had an idea. He ripped the subscription tag off a copy of Time and put it in his wallet. In the new few weeks, Jackie Easton would start getting subscriptions to Cosmopolitan, Glamour, and other female oriented magazines. He would also log online and sign Jackie up for some catalogs.

He wasn't really worried about the changes he had made to Jackie's home, as he hadn't gotten rid of anything that he considered she would miss. True, he was rewriting her life, but so far she didn't seem to mind. He wondered how she was doing with her lessons with Tess.


Chapter 20


"No, no, Jackie, go lighter with the eyeliner; remember this is makeup for work, not barhopping," corrected Tess. She handed her a tissue. "Wipe it off and try again."

"Okay," replied Jackie.

"Actually, you're doing pretty well for someone who just started wearing makeup. I have women friends who still don't know how to correctly make themselves up," replied Tess.

"I had some experience with makeup in school," replied Jackie.

They had been working on makeup for over an hour. Tess still wanted to spend some time picking out a better wig for Jackie. She had a program on her computer that would allow her to try several styles for Jackie. All she had to do was take a photo of Jackie and load it into the computer. The wig Jackie was wearing was nice, but it was too big, in terms of hair. It was perfect for going out partying, but Jackie needed something a bit more practical for work. She did agree with Jackie that she looked fantastic as a redhead, and the curls also looked good.

A little while later, they were looking at various wig styles on Tess's computer.

"There's a great wig shop a few blocks from here. They have some real high quality wigs; we should be able to find a style close to one of these tomorrow," noted Tess. "I'll print these out so you can think about what styles you like."

"What about my own hair?" asked Jackie.

"It'll be a few months until its long enough for us to do anything with it. We can have it dyed the same color as your wig if you want. We might be able to give you a slightly feminine cut sometime in the next month, but you'll look pretty butch. Maybe we can give you more body by giving you a permanent," stated Tess. "We'll also get your eyebrows waxed more and dyed to match your hair."

"Oh. I'm not sure how well that would go over at work," she stated.

"If we go with a less dramatic red, it won't look that different from your present color, and then gradually we can lighten it as it grows out," she explained.

"Won't the hormones make it grow faster?"

"Doesn't always happen, Jackie," replied Tess. "You'll be stuck with the wig for a while. Still, you look pretty femme. I seriously doubt if anyone would make you."

"Make me?" asked Jackie.

Tess laughed. "How do I put this... how about, realize that you have a penis?"

"Oh!" replied Jackie as she started to giggle.

"This is a pretty liberal city, but be careful. For some reason, some men can find you very threatening," explained Tess. "Also be careful when you go out."

Tess then gave Jackie a lecture in personal safety.

"I had no idea," replied Jackie.

"You're a very attractive woman, and men will try to take advantage of that. They'll also see you as weaker, and some will see you as a victim. If they think you're a complete woman, and they discover your secret, they can freak out."

"I have a boyfriend," replied Jackie.

"I'm not talking about you going on a date, but what happens if someone grabs you in the parking garage of your loft?"

"I hadn't thought about that," replied Jackie.

"You need to be aware of your surroundings now more, Jackie. I would hate to see you get hurt," stated Tess.

"I'll be careful," replied Jackie.

Tess nodded. "Okay, tomorrow evening we'll go shopping. We'll focus on work and casual clothes. We'll also pick up some wigs."

"Sounds like fun," replied Jackie.

"Now, just so you know, all the places we'll be going tomorrow are T-girl friendly. They won't 'out' you, and they'll treat you like a woman, so you don't have to worry."

"Thanks, Tess," replied Jackie.

"You're welcome. Look, I know that this is business, but I like you. I'd like to be friends with you, if you don't mind."

"You mean that?" asked Jackie.

Tess nodded. "Yeah, you're nice. I'd like to see how you grow."

"Thanks," replied Jackie.

"Now, we have one more thing to do before you leave; I need to do your nails," stated Tess.

Jackie held out her hands. "I had totally forgotten."

"It might have raised a few questions tomorrow," stated Tess as she filled a bowl with nail polish remover. "Now, you need to soak in this for a while. After I remove the fake nails, I want to see what I can do with your own nails."

Like most men, Jack kept his nails short, but Tess was able to do some shaping with a file to help Jackie. She also cut back some of her cuticles and gave her nails a coat of clear polish.

"Won't someone notice?" asked Jackie looking at her nails.

"Maybe, but I doubt it. Besides, didn't you tell me that many of your co-workers think that you're 'T' anyway?" asked Tess.

Jackie just smiled and shrugged her shoulders and realized that work would be interesting from now own.

"I have something to ask you, Jackie. This weekend can't really be the first time you realized that you were a woman. You must have been struggling with this for years," stated Tess.

"That's not a question," replied Jackie.

Tess laughed. "I do that all the time. But you know what I mean!"

Jackie smiled back. "Not today. I have some thinking to do first. My feelings were repressed, but it's rather painful, and I don't know if I'm even ready to go there."

Tess nodded. "I'll be here when you're ready to talk."


Chapter 21


"You look great, honey," stated Chris as he escorted her back to the car. "Did you do your own makeup?'

"Yes, after several attempts," she replied.

He opened the car door for her and then kissed her long and passionately. His tongue pressed deep into her mouth.

"That was nice," stated Jackie with a sigh.

"I just wanted to let you know I love you," replied Chris.

Chris drove directly to Jackie's home. He wanted to see her reaction to the changes.

They walked in together, and Jackie immediately noticed that her place had changed.

Jackie walked around and absorbed the changes. Chris closed the door behind him and watched her. She ran her hands across her new bedding, and then she checked out the bathroom. She then began to open up her drawers and saw that they contained her feminine clothes. She looked over her shoulder at Chris and smiled as she opened up her closet. Inside, she saw that Chris had removed most of her male clothes.

"Thank you," she replied as she sat down on the edge of her bed.

Chris walked over and sat down next to her. He put his arm around her and pulled her close.

"You don't mind?" he asked gently.

"No, not really. It helps speed up the process and saved me from doing it myself," she replied softly. "I like that you've made decisions for me. I never thought of myself as submissive, but it feels so natural now. It also turns me on. I can't imagine ever going back."

"I don't want to totally dominate you, Jackie," he replied. "I don't want a slave."

"Even if you do, I don't mind," she replied with a smile.

Chris cocked his head. "What do you mean?"

"It's complicated. I'm reliving feelings that I haven't felt since my parents died. I haven't had anyone who wanted me. I've had to make all my own decisions since I graduated high school. I haven't had anyone to help me, or anyone who I could go to for advice. I've missed that in my life. But it goes even deeper than that," said Jackie.

"What do you mean?" asked Chris.

"Since you've taken me in, I've found that I love being submissive to you. I love how you're re-writing my life," she stated. "I'm willing to let you transform me as you please, with one provision... that is you must promise that you'll love me."

"Jackie, I do love you. You're everything that I've ever wanted in a lover," he replied.

"That's what I've wanted to hear," commented Jackie. "I trust you and love you."

"There's more isn't there?" he asked.

Jackie nodded. "But I'm not ready to even think about those thoughts yet. Please be patient with me."

"I will." Chris then pulled her into his arms and began to kiss her. They were soon rolling around on her bed in carnal lust.



Chapter 22


"So which wig do you like best?" asked Jackie. She was showing Chris the printouts of the various wig styles.

"I like this one," said Chris, pointing to one of the images. It was mid-length with large curls.

"I thought you'd pick that one," replied Jackie. She was dressed in a black lace teddy.

"I'd like to see you tomorrow evening. I should be home around six," he replied. "Call me when you get done shopping. You can model your new outfits for me."

"I'd like that," replied Jackie.

"I'll also call tomorrow to make an appointment for you with the doctor," continued Chris.

"Cool. Do you think that he'll be able to see me soon?" asked Jackie hopefully.

"I can't answer that, my love, but we'll get you on hormones as soon as possible. How's your piercing feel?" he asked.

Jackie reached down and ran her fingers across the steel ring that ran through the head of her clitty. "It doesn't hurt anymore."

"Good, but keep an eye on it and use the antibiotic on it. I don't want you to get sick," continued Chris.

"I promise," replied Jackie.

"Does the idea of having additional piercings bother you?" he asked.

"Like what?" asked Jackie.

"I'd like to have a small ring through each of your nipples and maybe a stud through your tongue," he stated.

"Really?"

Chris nodded. "We wouldn't get the nipple rings until after your breasts grow out a bit, and as for the tongue, we can wait until after you move in with me full time," stated Chris as he ran his finger around her nipples.

"Okay. Can I ask you something else?" she asked.

"Yes, my love," he replied.

"You've obviously thought a lot of this out; now you don't have to give me all the details, but what's your ultimate plan for me?" she asked.

Chris nodded. "That's a fair question. I eventually want you as a fulltime trophy wife. I really don't want you working fulltime; rather, I want you being my lovely sexy wife. I could accept you working part-time, but I'd still want you waiting for me at the door, eager to see me and please me. In return, I will take care of you and love you. Does that answer your question?"

Jackie nodded. "Yes, it does, thank you."

"And how do you feel about that?"

"I love it," replied Jackie.

"Now, how have you been paying Tess?" he asked.

"I've been using my credit card," she replied.

"Tell her that I'll write her a check at the end of the week," he stated.

"Okay. I like her a lot," said Jackie. She went on to tell Chris what Tess had said.

"Good, I think you need some female friends, someone to guide you," he replied.

"Thank you, Chris," stated Jackie.

"I'm also going to contact my lawyer about getting your name and gender legally changed," continued Chris.

"So, I would have a driver's license that says that I'm a woman?" asked Jackie.

"Of course. It seems silly that your ID would mark you a male, once you've started living fulltime as a woman," stated Chris.

Jackie snuggled up close to Chris. "I can't believe that this is happening. It's happening so fast, but then again, not fast enough."

Chris kissed Jackie. "I know. I can't wait until you're the beautiful woman you were meant to be."



Chapter 23


Jackie dressed in a suit the following morning. She was wearing silk panties under the male trousers. Instead of socks, she was wearing black pantyhose. It felt nice against her legs. She looked at herself in the mirror. Other than her pierced ears and slightly trimmed eyebrows, she didn't look that different from Jack. However, on the inside she felt totally different.

She ran her hand across her now smooth face. While Jack didn't have a thick growth of facial hair, Tess had quickly convinced Jackie that she didn't want to keep shaving. Tess told her that she would make the first of a series of laser hair removal appointments for her. Tess told her that she might still have to get some electrolysis.

Jackie also hoped that her first appointment with her doctor would be soon, as she couldn't wait until her breasts began to grow.

Jackie fidgeted in front of the mirror. She was nervous and pleased that Chris stopped by on the way to work to see her.

"Relax, honey, you'll do fine," he stated.

"I know, but I'm still nervous," she replied with a giggle.

"No matter how it goes, just remember that you'll be in my bed tonight," he said.

Jackie broke out in a full laugh. "Great, now I'm horny and nervous."

"So tell me how you see yourself right now?" asked Chris as he sat down on the edge of her bed.

"I see myself as a woman forced to dress as a guy," she replied.

These were the words Chris had wanted to hear. "That's right, Jackie; you're not a man anymore. Look me in the face and repeat that."

Jackie turned around. "I'm not a man anymore. I'm Jackie, and I'm a woman."

"Whose woman?" he demanded.

Jackie smiled. "I'm your woman."

Chris nodded and unzipped his pants and pulled out his hard cock. "Show me, Jackie."

With only a second of hesitation, Jackie was soon on her knees pressing her lips against Chris's cock. It began to slide in between her lips.

Chris reached down and placed his hands gently on her head and guided her. "No matter how you dress now, no matter how others address you, no matter what your present ID says, no matter which bathroom you use at work, you're not a man; you're Jackie, my woman, my girlfriend. You suck cock like a woman, you make love like a woman, just remember that, my love."

Jackie moaned her reply as best she could while sucking Chris's cock. Her mouth was soon full with his seed as he came, and she obediently swallowed every drop.

"That was perfect, my sweet. Go and wash up, and I'll see you at work," stated Chris. "I love you."


Chapter 24


Jackie arrived at her cubicle and got right to work. She thought about how good it had felt to suck off Chris that morning as she worked.

It was right before lunch when she heard a voice just outside her cubicle. "Hi Jackie, or are you back to being Jack," stated Lisa with a laugh as she ran her eyes over him.

Jackie turned around and laughed. "Jack is fine."

"Hey, I was wondering if you had plans for lunch," she asked.

Jackie was caught off guard, as no one had ever asked her out to lunch. "Um, no, I mean, sure that would be cool."

"Great, you free now?"

Jackie looked her watch; it was a feminine version of her old electronic one. Chris had bought it for her. It read 12:15.

"I had no idea it was so late," she replied.

"Come on, I'll drive," stated Lisa.

They drove to a small bistro a few miles from the office. It was familiar for some reason to Jackie; then it hit her, Tess's office was across the street.

"I've wanted to try this place for a while, but none of the men in the office ever wanted to go," said Lisa.

Jackie wondered if Lisa was just making small talk or if she was trying to bait her.

They were shown to a seat by the window. Jackie could look over and see the front door of Tess's office.

"I had to admit that you caught me off guard at the party, Jackie, err, I mean Jack," stated Lisa as she looked over the menu. "Still, I have to admit that you make a very attractive woman."

Jackie didn't know what to say and every second she hesitated made the moment more awkward.

"I had a little too much to drink," Jackie stammered as she nervously looked at the menu.

Lisa was twenty-five and very aggressive. From what Jackie had heard, Lisa was on the fast track at Chambers. She was also very attractive.

Lisa was two inches talker than Jackie, and was trim and athletic. Her auburn hair was cut short, but still looked feminine. In some ways, she reminded Jackie of the first female security officer on Star Trek: The Next Generation.

They ordered lunch, and while Jackie tried to shift the conversation to small talk or work, Lisa wouldn't let go of the party.

"Seriously, Jackie, you seemed more natural at the party than you do now," stated Lisa. She then reached over and took Jackie by the hand and examined her nails. "Nice. I love the clear coat. None of the men will notice it, and yet it looks so feminine. I also love the women's watch on your slender wrist."

Jackie felt her face start to get warm and tried to pull her hand away.

"Oh, that's so cute, you're actually blushing!" whispered Lisa. She then leaned over and smiled. "Don't worry, Jackie. I won't give away your secret. I think it's so hot. I love a man who is willing to surrender to his feminine side. Besides, it's the only way that our office will ever get another woman in it!"

"So... you're okay with it?" asked Jackie softly.

"Okay with it? By god, Jackie, this is incredible. So are you going to go fulltime?"

Jackie looked around and saw to her relief that no one was paying her any attention. "Yes, but not for a few months."

"Well, I'll support you completely. Besides, I'll finally have a girlfriend in the office I can hang out with," stated Lisa. "Christ, I'm so bored around here."

It hit Jackie that there were only a few other women in the office. Two were married and in their fifties. The only other single woman was Stacy, a pretty blonde who was engaged to a marine.

"Do you hit the clubs?" asked Lisa with a twinkle in her eyes.

"I'm sort of new to this, in many ways," stated Jackie.

"Oh, of course, and you're also new to town. Well, I go out almost every weekend, and trust me, no one would know you're a guy," continued Lisa. She then ran her eyes over Jackie. "I'd love to take you out on the town if you'd like."

"Um, I guess that would be fun," replied Jackie.

"Jackie, I'm not looking for a lover, just someone fun to hang with," stated Lisa.

"That's nice to know," replied Jackie.

"Now, I know you like women, but do you like men?" asked Lisa bluntly.

Jackie hesitated for a moment before answering.

Lisa put her hand up and smiled. "It's okay, I like them too."

Jackie began to feel her face get warm again.

Lisa leaned over and whispered. "Did Chris take you to bed after the party?"

Jackie almost choked on her food.

"It's okay, love. I saw you two leave together, and I know how smooth he can be. Chris is really nice, but he's too demanding for me. I like to be in charge myself. Oh, don't worry, it'll be our secret. Besides, I think you two make a hot couple," continued Lisa. "I like Chris, and it was a shame that his last wife dumped him."

"Who else saw?' asked Jackie, with a slightly worried look on her face.

"No one that I know of," replied Lisa. "I think I was one of the few people left at the party who was observant. Look, I think it's cool that you're really a chick, and I'm willing to help you. I think hitting some clubs would be good for you; you need to learn all aspects of being female. Since you've got a man, you can relax and let them slobber over you at the clubs. Trust me; we won't have to buy many drinks!" Lisa began to laugh.

Jackie couldn't help but join in.

They talked some more on the way back to work. Jackie wasn't totally sure of Lisa's intentions, but she felt she could trust her. She would still tell Chris, although she doubted he would mind. She shook her head in disbelief as in less than a week Jackie had a bigger social life than Jack had ever developed.


Chapter 25


She called Chris on the way over to Tess's place. As expected, he didn't mind.

"Lisa's pretty wild. We went out once or twice, but we both wanted to be on top. I think it's great that she wants to be your friend," stated Chris.

"She says she just wants to be friends," remarked Jackie.

"If she wants to sleep with you, I don't mind. I know you love me, and I love you. Just tell me afterwards," he replied. He was pleased that Lisa had taken an interest in Jackie, and he hoped they would have sex. He knew that Lisa would totally dominate Jackie, and this would only help to reinforce Jackie's submissiveness and femininity.

"You don't mind?' asked Jackie, slightly taken back.

"Honey, I do want you all to myself, but if you have a fling with Lisa, that's fine. I don't consider you having sex with another woman as cheating, but let's be real clear; I'm the only man in your life."

Jackie sighed. "I just wanted to make sure that you really love me."

"Don't worry about that, you're my woman, and I love you," stated Chris.

"Well, I'm just about to Tess's place," stated Jackie.

"I can't wait to see you. I love you, Jackie," said Chris.

"I love you too," she replied.



Chapter 26


Tess watched as Jackie did her makeup. Jackie had arrived at Tess's place directly from work. She had a bag of female clothes in her trunk that she carried inside with her.

"Not bad, Jackie. I'm very impressed with how quickly you've picked up on it," stated Tess. "Here's a wig for you. I stopped by and picked one up for you."

Jackie held it out and saw that it was close to the style she and Chris had liked. She slipped it on and adjusted it.

"That looks fab on you!" exclaimed Tess. "Finish dressing and we'll head out."

Jackie dressed in a short skirt, heels, and t-shirt. She wore a denim jacket over the shirt.

Tess looked at Jackie and nodded. "Nice outfit, although it makes you look like you're eighteen. I know, I'll just tell everyone that you're my kid sister."

Jackie laughed and looked at herself in the mirror. "I see what you mean," said Jackie. "Should I wear something else?"

Tess shook her head. "No, sit down, I want to try something." She then removed Jackie's lipstick and replaced it with a slightly brighter color. She then adjusted the rest of Jackie's makeup and hair. She also gave her some more flamboyant jewelry to wear.

"Take off that top and put this one on," stated Tess handing Jackie a low cut pink top with sequins on it.

Jackie obeyed and Tess nodded in approval.

"Now, you really look like a teenager," stated Tess.

Jackie looked at herself in the mirror, and it was true; she looked like she was in high school.

"This will make it even easier to help you pick out stuff. It'll look like I'm helping you pick out an adult wardrobe and it'll raise less questions. Oh, your boyfriend called me today and gave me some ideas on outfits for you. He also told me to keep a tab and he'd pick up the costs."

Jackie nodded, almost unable to take her eyes off the new younger version of herself.

"You've got to go to him like that, he'll love it!" stated Tess.

"You sure?' asked Jackie.

Tess nodded. "Guys love young girls, especially when they know that they won't get in trouble."

Jackie laughed.

"Okay, little sister, come on, we've got some shopping to do."



Chapter 27


Jackie was impressed with how good a shopper Tess was. She was able to pick out things that could be interchanged with each other.

The clerks actually bought that Jackie was a teenager, although one woman made Jackie.

"So tell me, who is he?" she asked, leaning over towards Tess.

"My brother, he lost a bet with me," replied Tess with a giggle.

"Your little brother makes a cute girl. You ought to keep her in skirts," said the woman.

Tess laughed. "I agree, he's much easier to control this way too."

Jackie forced a laugh when Tess told her about the conversation. She also noticed how easily she submitted to Tess.

"Okay, little sister, we've done enough damage to Chris's budget tonight. Let's head back to my place," stated Tess.

"I can't believe we got so much stuff," replied Jackie.

"I'd like to see what else you have at your place," stated Tess. "It'll help me decide what else we need for now."

"You want to go now?" asked Jackie.

"Sure, I'd love to see your place."

They arrived a few minutes later and together they carried everything inside in only two trips.

"I like your place, Jackie, it's small, but cozy," noted Tess as they unpacked the clothes.

Jackie noticed a few new changes to her home. Obviously, Chris had been in again and had changed a few things. There were now prints of wildflowers on the walls instead of the prints of cars.

"Oh, I need to call Chris," stated Jackie as she picked up the phone. He was glad to hear from her. She explained how Tess wanted to see her place. "I like the changes."

"I knew you would," stated Chris. "Look, you can give me the full fashion show later, but I do want to see you after you drop off Tess."

"Okay," replied Jackie.


Chapter 28


Chris smiled at the same time he felt his cock hardening as Jackie walked in and posed for him.

"And you went out with Tess the whole shopping trip like this?" he asked.

Jackie nodded.

"Cute," he replied. He pulled her close and began to kiss her. "Even as a teen, you're mine."

His goal was to have sex with her often, so that she would learn to crave it. So far, he wasn't disappointed. They ended up having sex on the couch. It pleased him knowing that his seed would be dripping out of Jackie's pussy as she drove home.

He sat back and sipped some brandy. The addition of Lisa to all this was unexpected, but would definitely speed up Jackie's transformation. He liked Lisa, and he had always felt it was too bad she was also dominant. The two times that they'd had sex it had been very good.

The doctor agreed to get Jackie in early after Chris talked to him. The four hundred dollars he had been given didn't hurt matters either. He smiled at the thought of Jackie starting hormones in a few days. He had also contacted a plastic surgeon friend from college regarding breast implants and facial surgery, just to get an idea of how much it would cost and how complicated the surgery would be. He gave the doctor photos of Jackie, and his friend agreed that he could make Jackie look very feminine.

True, this was costing him a lot of money, but it was worth it, he thought. Besides, Jackie was very good in bed.


Chapter 29


Jackie dressed the next morning. She was slightly disappointed that Chris wasn't stopping by on the way to work. She smiled to herself thinking how addicted she was becoming to his cock.

Instead of her normal dress shirt, she decided to wear a woman's version. It didn't look that different from her male shirts, but it made her feel sexy knowing that she was wearing a blouse.

At work, Chris told her that he'd arranged for her to have Thursday off so she could go to the doctor.

"The doctor's even covered by our health program," stated Chris with a smile.

"Thank you," replied Jackie. "I'm going to see Tess this evening. She's taking me to a salon."

"Are you getting your hair dyed tonight?" he asked with a grin.

Jackie nodded.

"Good. Oh, don't forget to get your pubic hair dyed the same color," he whispered. "Call me when you're done."

Jackie stood there in shock and couldn't help shaking her head. I should have thought of that, she thought as she returned to her cubicle.

Lisa stopped by later. "You want to go to lunch?" she asked.

"Sure, that sounds good," replied Jackie.

They went back to the same place as before.

"I like this place, and it gives us a chance to talk more openly," stated Lisa. "But don't worry. Jackie, I won't out you."

"I appreciate that," replied Jackie.

"I like your blouse. It took me a while to notice it. Has anyone else said anything?" she asked.

Jackie shook her head. "No. I guess I should be glad that you're the only observant person in the office."

"It'll be interesting to see how long it takes before someone notices, especially when you start hormones," replied Lisa.

"Well, we'll see even sooner, as I'm getting my hair done this evening. Mostly, I'm getting it colored, along with my eyebrows. It's really too short to do anything with it right now," replied Jackie. It was nice to have someone she could talk to openly with.

"What color are you getting?"

"Close to the color of the wig I wore at the party," replied Jackie.

Lisa ran her eyes over Jackie. "That's a nice color for you. I doubt many will notice or say anything."

"I'm still sort of amazed at how calm I've been through all this. I mean, last week at this time I was just Jack, the unknown, barely-noticed new guy. At work, I'm still that, more or less, but my life is being re-written, and I love every change," said Jackie. She then told Lisa about the previous night and about how Chris had changed her apartment.

"That's pretty hot. Damn, I wish I could have seen you in your teenage mode. Maybe we can both go out some night as 'younger women.' That would be fun," replied Lisa.

"Yes, but we wouldn't get served. Tess said that I looked barely eighteen," replied Jackie.

"I'd like to meet Tess sometime; she sounds fun."

"She's nice. Maybe we can all go out sometime," replied Jackie. She then began to laugh.

"What's so funny?" asked Lisa.

"I just realized that I have more women friends than male friends in town."

Lisa laughed. "Well, why not? You're well on your way to being a woman yourself. Speaking of which, you want to go out clubbing this weekend?"

"I need to check with Chris first, but he liked the idea of me hanging out with you," replied Jackie.

"Cool. Do you have a short dress, something fun to wear?" she asked.

Jackie nodded. "Yes, I'm quickly acquiring a new wardrobe. Chris also likes me in short dresses and skirts."

"And you want to please him, of course," replied Lisa.

"Yes. I know it seems strange, but I love pleasing and obeying him," replied Jackie.

"It's not strange; you're a submissive, and it's great that you've accepted this. True feelings shouldn't be repressed," stated Lisa. She reached into her purse. "Here's my home number. Feel free to call me after work."

"Thanks," replied Jackie. She wrote down her own number and gave it to Lisa. "Here's mine."

"Cool. Well, as soon as you know if you're free for a girls' night out, let me know. Also I would like to take you shopping; it'll be fun."

"I'd like that," replied Jackie.

Lisa barely contained her smile as she sipped her water.

"Now, have you thought of wearing a camisole under your blouse?" asked Lisa.

"Wouldn't it show through?" replied Jackie.

"No, they make many that are smooth. We can stop and get some on the way back to work if you want,'" stated Lisa, knowing the offer would be too good for Jackie to resist.

"Okay," replied Jackie.

"Oh, I can't wait to take you out on the town. It'll be so much fun," stated Lisa.



Chapter 30


"Well? What do you think?" asked Maria, the stylist who had just finished working on Jackie.

Jackie stared at herself in the mirror. Her hair color was now a reddish brown, as were her eyebrows. Maria had also trimmed back Jackie's sideburns and layered the body of her hair. It was amazing how different it looked.

"Now, there's a lot of mousse in your hair right now, so don't worry; you'll pass as a guy at work. The next time I dye your hair, I'll make it redder. In a few months you'll have dark red hair, and most people won't notice the change.

"I don't know about my eyebrows," stated Jackie. "They're very thin now."

"Don't worry, Jackie. Men don't notice those sorts of things. Besides, I'm going to make them even thinner next time."

"You look great, Jackie," stated Tess. "I told you Maria was great."

"As you hair grows, I'll work it so you can go without your wig. Right now you could pass as a real butch girl."

"I'll stick with the wig for now," replied Jackie as she ran her fingers through her hair.

"Well, we're not done yet. I love the idea of dying your pubic hair. Now, lie back and let me get back to work," stated Maria.

When she was done, Jackie looked down at the magic Maria had performed. Her pubic hair was now a deep red, and was styled to look neat and feminine.

"I went darker down there as most people won't see it anyway," giggled Maria. "By the way, I love the piercing."

"Thank you," replied Jackie blushing slightly.

"It's so cute, I bet it helps to enforce your feelings of femininity," added Maria.

"It does," replied Jackie.

"I'll put you down for an appointment in a month," stated Maria. "I'm going to enjoy working on you, Jackie."


 
Chapter 31


Chris ran his fingers through Jackie's hair as they lay in his bed together. "Very nice, very nice indeed; you've made me very happy, my sweet." He was very pleased that she had followed all his commands.

Jackie trembled with excitement. She loved that Chris was pleased with her. "I love pleasing you."

"I know, my sweet. Now, when you go to the doctor on Thursday, I want you to be dressed nice. Don't worry, the doctor works with girls like you all the time."

"So, I'll be on hormones soon?"

Chris nodded. "I can't wait to see the changes." He ran his fingers across her nipples. "These are going to get very large." He leaned down and began to kiss them.

Jackie moaned. "Mmm, that feels so good."

"If you like it now, you'll love it once they start to grow," replied Chris as he leaned down to begin sucking on Jackie's nipples.


Chapter 32


"So you really don't mind that Lisa and I are going clubbing?" asked Jackie as she dressed.

"No, I think it's great. I told you that I trust you, and I think it's cool that you're developing a girly social life," replied Chris. He was pleased that Jackie was developing a social life. It would only enforce her new feminine status. "In fact, I think you should go out with your girlfriends regularly."

Jackie leaned over and kissed Chris. "Thank you so much."

Chris kissed her back. Inside, he was pleased that she was asking for permission. "Look, you're a woman now, but I understand that you may still have feelings for women. I don't mind if you have a fling with another woman, just as long as I stay the only man in your life and you tell me all about it."

"I promise that I'll never cheat on you," she replied.

"I know that," he replied and kissed her again.

As soon as Jackie got home, she called Lisa and told her the good news.

"That's great. I can't wait."

"So what night is best for you?" asked Jackie.

"Why not Friday? That way you'll have the rest of the weekend with Chris," she replied. "Oh, I went shopping this afternoon after work and saw the perfect dress for you. Are you free tomorrow to go shopping?"

"Can we go Thursday, I have a doctor's appointment that day?" replied Jackie.

"Okay. Well goodnight, girlfriend," stated Lisa.

Jackie hung up the phone and decided to have a glass of wine before going to bed. Her life had changed so drastically in the past week. She was now living two lives. At work she was Jack, but as soon as she came home she was Jackie. Actually, even at work she was barely Jack. Other than Lisa, no one had noticed that she was wearing a blouse with her suit. She wondered how far Chris would take this before she became totally Jackie at work.

She sat down on her couch and sipped her wine. She was only wearing a red silk teddy, and she loved how it felt against her smooth body.

Jackie thought about how Chris had taken control of her life. She should have fought it, but why? It felt so good to be under his control, and it wasn't like he was making her do anything against her will. Then again, it seemed unthinkable to disobey Chris, and her will to resist was almost nonexistent; besides what was the harm? A week ago she was just a nobody working on a computer in a new city; now she had a boyfriend and a social life. So what if that meant she was becoming a woman? It was better than being alone all the time, and both Jack and Jackie had had enough of that.

Jackie finished her wine and went to bed thinking about Chris and how good it felt to be in bed with him.


Chapter 33


It was Thursday, and Jackie was sitting on an examination bench across from her doctor. She had been slightly surprised that the doctor that Chris had arranged for her to see was a black woman. She was also surprised that the doctor was from another country.

"May I ask where you're from originally?" asked Jackie.

The woman smiled. "I'm originally from Haiti, but I moved to the states ten years ago," replied Dr. Bonnet.

Jackie nodded. "I detected a French accent, but I couldn't quite place it."

"I picked up my accent in Paris. My parents moved there when I was five. We sort of bounced back and forth between there and Haiti," stated Dr. Bonnet. "Now, you look like an excellent candidate for gender reassignment. Usually, I would like a letter from a therapist, but since you're living almost fulltime and seem very well adjusted, I'll bypass that."

"Thank you, Dr. Bonnet."

"Now, I can start you off on a new combination drugs of that I've been working with. I've been getting some very good results with them, and you have the right body size for them. You're in great shape, but you have sufficient body fat for redistribution."

"What sorts of results?" asked Jackie.

"Well, I've seen much faster changes than with conventional hormone treatments. You should notice changes in the next few weeks, and your breast development will be much faster," stated Dr. Bonnet. "Now, if you agree, I will need to see you weekly to monitor the changes via blood work."

"Okay," replied Jackie. "The faster the better."

"Wonderful, now the first treatment is an intravenous infusion, and will take an hour. Would you like to make an appointment or start now?" she asked

"Now, please!" replied Jackie immediately.

Dr. Bonnet smiled. "I thought that would be your answer. Okay, follow me to the treatment room. You'll get the first treatment today, and this will be supplemented orally every day. As you progress, I would like to have you get an infusion once every two weeks."

"That sounds fine. Are the other supplements pills?" asked Jackie.

Dr. Bonnet shook her head. "It's a liquid. It's an herbal treatment that I've been using, so it's all natural. It sort of tastes like a fruit smoothie, but not as sweet."

"Okay," replied Jackie.

Dr. Bonnet went on to tell Jackie what to expect. "Your skin will become softer, and your body hair will get lighter and less coarse. Of course, you'll have fat redistribution to the hips, buttocks, and breasts. Your muscle mass will decrease, and you'll find it harder to get an erection. You may also find that your emotional state is more changeable."

"Will I still have sensitivity there?" asked Jackie.

Dr. Bonnet opened a door to a small room. Inside was a bench with an IV stand next to it. "Yes, and you'll even have orgasms, but your male organ will be smaller and won't get hard. Now, lie down on the bench, and I'll get the treatment."

A few minutes later Jackie was getting her first treatment. She knew that there would be no results for a while; still, she felt different as the clear liquid entered her arm.

Dr. Bonnet monitored the treatment and smiled. "I think you'll be very pleased with the results. I'll have the liquid supplements ready for you at the front desk. My nurse will take over for now. I'll see you next week, Jackie."

"Thank you, doctor," replied Jackie. She had to think as she waited for the treatment to end. Just as Lisa had said, no one had commented on her new hair color. It was amazing how some people paid so little attention to others. She had confidence that as her hair grew out she would be able to transition the style from more unisex to feminine. All her work shirts were now blouses. They weren't that different from her male shirts, but it meant a lot to her knowing she was now wearing some women's clothes at work. Chris suggested that she start wearing women's slacks to work soon, and she was looking for some that would go with her male jackets.

An hour later Jackie departed Dr. Bonnet's office with a large bag of sealed bottles. She was sort of surprised that she wasn't given a prescription for pills, but whatever worked, she thought.


Chapter 34


Jackie looked at her watch again and nervously sipped her drink. Lisa was supposed to meet her for lunch, and she was ten minutes late. She was sitting in a bistro a block away from their regular place, and while she felt confident in her appearance and ability to pass, she was still nervous about sitting alone.

Lisa walked inside a few minutes later and scanned the room. She then noticed Jackie and smiled and walked over to join her.

"Jackie, you look great," commented Lisa.

Jackie was dressed in a short skirt, white blouse, and heels.

"Thank you," replied Jackie.

"So how did the exam go? Are you on hormones now?" asked Lisa.

"Yes," replied Jackie, and she told Lisa about Dr. Bonnet.

"I've been doing some online research about hormones the last few days, and I read about the process you're on. I can't wait to see if you bloom as well as the women in the photos," commented Lisa.

"Dr. Bonnet said that I should start seeing results in the next few weeks," replied Jackie.

"Well, since no one noticed your new hair color, I doubt they'll notice when you start growing breasts," stated Lisa.

"As soon as it becomes noticeable, I want to switch over and become Jackie all the time," stated Jackie.

"I don't know; I find it really cool that you're in between and pushing the boundaries. It's a bit of a turn-on knowing that every day you're becoming more and more feminine and that almost no one knows!"

"Maybe they're all just being polite," stated Jackie.

Lisa shook her head. "No, they're all too wrapped up in their own little worlds. I bet you could wear heels to work and none of them would notice."

"They might notice heels," replied Jackie with a laugh.

"Yeah, but they wouldn't notice flats. Eat fast; after I show you the dress, we'll go to the shoe store. I have a great idea!"

They stopped at a shoe store a few blocks up the street. Lisa led Jackie inside. It was a self-service discount store.

"Look at these shoes, Jackie," stated Lisa.

She was pointing to a pair of black flats.

"You could wear those at work, and no one would notice," continued Lisa.

"You really think so?" asked Jackie as she examined the shoes. They were functional, but not overly attractive.

"Absolutely. Look, you spend most of your time in your own cubicle writing reports and doing research. Who would see them?"

Jackie nodded and began to look for her size in the stacks of shoes.

"You could even wear stockings with them," said Lisa.

Jackie grinned. "I've already been wearing pantyhose every day - and even you didn't notice."

Jackie tried on a pair of black flats. They were comfortable and not that expensive. The idea of adding shoes to her feminized work attire was very arousing. She ended up picking out four pairs of shoes, two brown, and two black. The styles were all similar, and barring close inspection, few would suspect that Jackie was wearing women's shoes.

"This is so cool," stated Lisa as they walked out of the shop. "I have to admit that it's a big turn on knowing that Jack will be mainly dressed in women's clothes, and no one will know."

"I still have to pick out some slacks that will pass as male," stated Jackie.

"I'll keep an eye out for anything that looks good," said Lisa. "Now, let's go look at the dress I want to see you in for Friday night.

The dress was a jet black strapless dress. It had a lace-up corset-style back, and the hem was very short. There was boning built in to help with support.

"It's so hot; you'll look great in it," stated Lisa. "The built-in support will allow you to use pads to push up your boobies."

"I don't know," stated Jackie, as she looked at the dress.

"Don't make any decision until you try it on," interrupted Lisa. "Come on, let's find a changing room and see what you look like in it." She grabbed Jackie by the arm and pulled her towards the back of the shop.

Lisa helped Jackie into the dress. Jackie found that Lisa was right, and the lace up aspect of the dress helped give Jackie the illusion of having breasts as well as narrowing her waist a bit. Combined with the silicone pads, Jackie even had some cleavage.

"You have to buy this dress, Jackie. It looks great on you," stated Lisa. "I know Chris will love taking it off you." She then began to giggle.

Jackie laughed too. She had to admit that the dress looked great on her. "Okay, okay, I'll buy it. So what are you wearing?"

"I'll be wearing my red satin number; I'm not about to have you show me up!" she replied with a laugh.

"I doubt that I'll upstage you, Lisa," replied Jackie.

"Don't sell yourself short, Jackie; you're very attractive," replied Lisa. She glanced at her watch. "I need to get back to the salt mine. I'll see you tomorrow." She then gave Jackie a hug.


Chapter 35


Jackie was slightly nervous as she drove towards Lisa's address. Work had been a breeze. It was amazing that while a good part of her wardrobe was feminine, no one noticed other than Chris and Lisa.

She had to admit that the feel of stockings under her pants was a big turn on all day. She wore black stockings and a garter belt. Thankfully, they didn't show through her pants.

Jackie had gone home and changed into full femme before heading over to Lisa's. She would change into her new dress at Lisa's

She was nervous about going out to the clubs and what would happen if someone made her. Chris had told her that it was very unlikely, as she was so feminine, but Jackie wasn't totally sure. The last thing she needed was to get in trouble.

Lisa was wearing a silk kimono when she greeted Jackie at the door.

"Hey, right on time. Good to see you, girlfriend," stated Lisa. "Come on in."

Jackie walked in carrying her clothes.

"I like your makeup and hair, but I'd like to make a few changes, it you don't mind," stated Lisa. "I want you to look really hot tonight."

"I don't mind," replied Jackie. She noticed that Lisa's makeup was much heavier and sexier than hers.

"We're going to paint the town red tonight."

Lisa's condo was very nice. Jackie wondered how much a place like this cost, as it looked new. She followed Lisa back to her bedroom. Lisa motioned for Jackie to sit down at the makeup table.

"Now, just relax; I'm going to make you so hot," stated Lisa.

Jackie sat back and let Lisa go to work. She applied more eye shadow and eyeliner. She also used a lot of mascara.

"I want your eyes to be very dramatic," explained Lisa. She then went to work on Jackie's lips. She applied bright red lipstick, followed by gloss. "Oh, that looks so sexy."

Jackie had to agree. Unlike the previous week, she now looked not just sexy, but erotic.

"Okay, we need to get dressed; we can't keep the boys waiting," stated Lisa.

Chapter 36

They took Lisa's coupe downtown. Lisa had loaned Jackie a wrap to cover her shoulders as it was still a little cool at night.

She was carrying a small bag with her lipstick, money, and ID inside. Lisa had jokingly handed her several condoms.

"I promised Chris that I wouldn't have sex with other men," replied Jackie as she handed the condoms back.

"Keep them in your purse anyway. It someone sees them, they'll be sure that you're a woman," stated Lisa. "Oh, you should also carry a few tampons in there too. I'll give you a few later."

Jackie shrugged her shoulders and put the condoms back in her purse.

Lisa pulled the car in front of a large club and waited for the valet to come and park her car. The name of it was "Anything Goes."

"This is a great club," stated Lisa. "It's only open on the weekends, and it has a high cover charge, but it's worth it. They have four floors, two are dance floors, and the other two are lounges. The one on the top floor usually has a jazz or blues band playing. We'll work our way up there," stated Lisa.

"How high is the cover charge?" asked Jackie.

"Fifty, but it keeps out the cave dwellers. Trust me, in another hour they'll be turning people away," explained Lisa.

"So you come here often?" asked Jackie.

Just then a valet walked up and took Lisa's keys. "Hey, good to see you, Lisa," stated the valet.

Lisa laughed as she glanced over at Jackie. "Does that answer your question? I picked this place as I wanted you to feel safe. They know me here, and that will help you."

They walked up to the front, and after paying their cover charge, they were waved inside. Jackie had expected to be carded and was a little surprised when they weren't. She asked Lisa about it.

"They card you over there. That's where we'll get our hands stamped for alcohol. Don't worry, hon, they don't care about your real gender here; remember the name of the club," explained Lisa.

Just as she said, the man checking IDs barely raised an eyebrow when Jackie showed him her driver's license. He did run his eyes over her and then leered at her as she walked away.

He leaned over to his partner and smiled. "She's a guy," he whispered.

The other man smiled back. "I'd still hit it."

The first man laughed. "Me too."

Jackie and Lisa headed inside.

"I'm impressed at how easily you move around, Jackie. You act as if you've been wearing heels your whole life."

"I've been practicing," replied Jackie. "Oh, which restroom do I use?"

"You're choice. However, they have men's, women's, and unisex rooms on each floor. Use the one you feel most comfortable using. If you want, I'll go into the ladies with you."

Jackie nodded.

Lisa led them to the bar and ordered cosmopolitans for both of them. The drinks arrived and Lisa made a short toast.

"To your rebirth," she stated and sipped her drink.

Jackie laughed and followed suit. The drink was very good, and Jackie felt a warm glow throughout her body. "Wow, this is strong," she stated.

"I know, that's why you have to take it slow," replied Lisa.

They worked their way through the different levels as Lisa gave Jackie the grand tour.

"I don't think I'm ready to go out on the dance floor," whispered Jackie, as they watched the people dancing.

"You don't dance?" asked Lisa.

Jackie shook her head. "I was the typical bad white guy dancer as Jack."

"I've taken lessons," replied Lisa. "Hey, you should do that. It would definitely help you. I'm going to start taking salsa classes next month; you should join me."

"Salsa?" asked Jackie.

"Oh, it's lots of fun, and great exercise. What do you say?" asked Lisa.

"Okay, but only if we're in the same class."

"Deal!" replied Lisa.

They noticed a table open up and quickly grabbed it. It didn't take long for them to catch the attention of the men hovering around the dance area.

"It looks like we're outnumbered three to one," said Jackie, as she sipped her drink.

"More like five to one - typical Friday night," replied Lisa with a wink. "Do you mind if I dance?"

"No, not at all," stated Jackie.

"Cool, I need to dance. Watch my drink, okay?" asked Lisa.

Jackie nodded. Lisa had warned Jackie about men who would try to slip things into drinks.

Lisa was back after twenty minutes on the dance floor and smiled at Jackie. "I can't wait until you can dance. It'll be so fun being out there with you."

Within a few minutes, two men walked over to their table and asked them to dance. Lisa, nodded, got up and went out on the dance floor with one of them. Jackie politely declined the other man's offer. He was persistent and tried his best to get Jackie to dance with him.

"I'm not a good dancer," explained Jackie.

Just then the DJ switched to a slow dance number. "How about this one?" he asked as he extended his hand. "Come on."

Lisa had just returned and motioned for Jackie to accept.

"Okay," replied Jackie reluctantly.

The man was much taller than Jackie, and his muscular arms easily surrounded her as they danced close together. Jackie imagined what it would be like to dance with Chris to keep her mind off the fact the man was whispering in her ear. He was telling her how sexy she was and he wanted to be with her. She had to admit that it was a bit of a rush to be the object of his affections, even if it was only for a dance. However, she didn't appreciate his hands groping her ass.

She thanked him for the dance and quickly returned to Lisa.

"You dance better than you give yourself credit for, Jackie," stated Lisa.

"I wasn't dancing, I was just carried around by him," she replied as she finished her drink. "I need another... now."

Lisa laughed. "Let's head up to the top floor; it's more relaxed up there."

Jackie agreed. "I feel like a small fish in a shark pool."

Lisa laughed. "Welcome to the club!"

Chapter 37


They found seats at the bar on the top floor. A man was playing piano and another was playing a sax. The music was soft jazz.

Lisa ordered two more cosmopolitans.

"This is more like it," remarked Jackie. "Are the men always like that down there?"

Lisa nodded. "Did you go to clubs when you were...Jack?"

Jackie nodded. "I wasn't that bad."

Lisa cocked her head. "Really? You never copped a feel with a woman you were dancing with?"

"You saw that?"

Lisa laughed. "It was hard not to. So, answer my question."

"Okay, I might have gone too far. I had no idea how obnoxious it was."

Lisa laughed. "You know, when I'm ready to settle down, I may insist my boyfriend undergo something like what you're doing. It'll give him a better insight into what women go through. "

"I'm just glad Chris is nice," stated Jackie as she took a sip.

"He is controlling," stated Lisa.

"I don't mind that. He hasn't forced me to do anything I didn't want to," she replied.

"Are you sure?"

Jackie nodded. "Absolutely. I admit that I'm submissive, but he's not forcing me into anything. I love what I'm becoming. I haven't had someone care about me since my parents died. I've longed for a relationship like this for so long."

Lisa smiled back. "I just don't want to see you get hurt. While I have to admit that you're better off as a woman, I just want you to be sure that you're doing the right thing. This is a pretty drastic change."

"I appreciate your concern and friendship. It means a lot to me. No, I'm so happy about the changes. I don't feel like I'm dressing up, this is who I am now."

Lisa reached over and placed her hand on Jackie's. "You can count on me to help you."

Jackie sighed. "Thanks."

"I want to confess something to you. I lied at the party last week," confessed Lisa.

Jackie looked confused. "What do you mean?"

"When you hit on me, I said I don't like women. I lied," commented Lisa.

Jackie cocked her head.

"I think you're very sexy, and while I know you're seeing Chris, I wouldn't mind taking you to bed myself," continued Lisa.

"You mean that?" asked Jackie.

Lisa nodded. "I also love the fact that you're submissive. Like Chris, I need to be in control in bed."

"I don't know how good I am in bed these days; I don't know if I can mentally do it as a male," replied Jackie.

"So? I'm not looking for a man tonight, and besides... I'll be the one making love to you."

Chapter 38

For the second time in her life, Jackie found herself being led to bed by a more dominant lover. And as with Chris, Jackie was willingly submitting.

Even though Lisa was dominant, she was very soft and caring in how she undressed Jackie. They were back at Lisa's condo, lying together on her bed. Lisa was on top of Jackie, kissing and caressing her.

"Oh, my god, you got your clitty pierced, that is so hot," exclaimed Lisa. She licked her lips. "Yes, you're definitely doing the right thing, Jackie; you really are a woman."

They kissed and cuddled for a while. Lisa was in charge and dictated the action. She reached into her nightstand and pulled out a double ended dildo, attached to a leather harness. "I want to fuck you, Jackie," she stated as she strapped on the sex toy. "I want this bad, and have been thinking about it all week."

"Please, Lisa, fuck me," moaned Jackie, who had been worked into a full state of sexual arousal by Lisa.

Lisa positioned Jackie on all fours, facing the mirror on her dresser.

"I want you to see me behind you, my love," stated Lisa. She gently began to massage in lubricant, opening up Jackie's ass-pussy. With a seductive smile on her face, she began to press the dildo against Jackie.

Jackie gasped as she felt the toy enter her. Lisa eased it in slowly. She pressed her hips against Jackie, and soon her cock was deep inside her lover. The other end was deep in Lisa as she began to move in and out of Jackie. The sensation was everything she had hoped it would be, and she slowly increased her pace. Jackie was moaning and begging for more, which Lisa gladly obliged.

Their lovemaking increased as did their sense of urgency. Lisa reached around and stroked Jackie's clit, matching the pace and rhythm of their lovemaking. She wanted to make Jackie cum at the same time, and she just about achieved this, with her orgasm arriving moments before Jackie's.

Lisa pulled out of Jackie and withdrew the dildo from her own vagina. She had just enough energy to set it on the nightstand.

After a while, Jackie managed to moan out. "That... was... incredible."

"I... know," replied Lisa, as she pulled Jackie close to her.

They ended up falling asleep in each other's arms.

Chapter 39

The next morning, they were eating breakfast together.

"Thank you, Jackie. I really needed that," stated Lisa, as she spread some jam on her English muffin.

"I should be the one thanking you," replied Jackie.

"Well, I can tell you one thing, you're definitely a woman," added Lisa. "I tried that once with a guy, and he just couldn't handle it. You took it like a real woman."

"Thank you," replied Jackie.

As they ate, they talked about the previous night.

"Jackie, you told me that your parents died when you young; what happened?"

"My dad was an engineer and a pilot. He and Mom were flying back from a construction site in Alaska, and their plane crashed. It was a company jet, and it turned out that the maintenance had been neglected. I was ten at the time. They were great parents, and my only regret about them was that I never had a chance to say goodbye. They were here, and then they were gone," she replied sadly.

"What happened to you?"

"I was passed around from one relative to another. I was never really mistreated, but I was always the outsider. I never felt accepted by any of them."

"What do you mean?" asked Lisa.

"Well, I was taken care of. My parent's estate left me well off. Between their insurance and the settlement from the crash, I had a lot of money. My parent's lawyers put most into a trust fund, which pissed off the various relatives I lived with. They were given monthly checks that more than covered my expenses, but they wanted it all. One uncle wanted it to start his own business; a cousin wanted it to add a pool to their yard. It was pretty sick."

"When did you realize that they wanted the money more than you?" asked Lisa.

"I think it was when I was twelve. I would have given them the money, if they had treated me like one of the family. I bounced around until I graduated high school. I attended four in three years, and then went away to college. That was the last time I talked to anyone in my family."

"How awful," stated Lisa. "So do you still have the money?"

Jackie nodded. "Most is still untouchable until I turn twenty-five. I used some for college, but I still took out loans to pay tuition."

"It must have been a horrible upbringing. With moving around so much, it must have been hard to keep friends," stated Lisa.

"It was. I grew up seeking someone who loved me. In college, I went through a series of girlfriends. Looking back, I guess I was way too possessive and eager for a long term relationship. I guess that freaked some of them out. I mean, I was desperate to find someone. I guess I was lucky that no one took advantage of me."

"I can't imagine what that would have been like," replied Lisa.

"The last time I actually celebrated a birthday was when I was ten. Most holidays sucked too, as I always felt alone and not belonging."

"You mentioned that you were fortunate that no one took advantage of you...."

Jackie interrupted. "I know what you're about to say. But Chris loves me. I can feel it," she stated, pointing at her chest. "Is he the one that I'm going to spend my life with? I don't know, but he's the first person that I've been with in a long time who cares for me, and I need that... I need it badly."

Lisa nodded.

"I also consider you as someone who cares about me," added Jackie.

"Thank you. I wish you all the best with Chris. He is a nice guy, and I also feel that he means the best for you," she stated.

"Thank you. I did enjoy last night and hope we can go out to the clubs again," said Jackie. "I'll even learn to dance."

Lisa laughed and then kissed Jackie. "That's the spirit!"

Jackie laughed.

"Hey, go back to the girls you dated in college. You said that they didn't want to get in a long term relationship with you, right?"

"Yes," replied Jackie.

"But did you stay friends with them?" she asked.

Jackie nodded. "Yes, we didn't have bad breakups. They said that they wanted to stay friends, which we did."

"I bet they sensed that you were different. I had a transgendered friend in college, and I always felt different around him, even before I knew his secret."

"You think so?" asked Jackie.

"Yes, you kiss and make love like a woman. I bet they sensed your feminine side," stated Lisa. "In fact, I bet that if you were to call them and tell them that you're now Jackie, I imagine they wouldn't be surprised."

"That would make sense," replied Jackie.

"I think the reason you didn't see this in yourself sooner was that you were too busy looking for someone to love you. You repressed anything that might make you less desirable."

"Anything else, Doctor?' asked Jackie with a grin.

"No, but think about it. You just didn't turn into a girl last week. Obviously, this is something that was deeply repressed, and now it's out like a volcano erupting," continued Lisa. "I just want you to know that I'll be there anytime you need help."

Jackie smiled back. "That means a lot to me, thank you."

"And if Chris breaks up with you, I have dibs!"

Chapter 40

Chris wasn't all that surprised that Lisa had bedded Jackie. In fact, he had hoped she would. He was pleased to hear how Lisa had used a strap-on to fuck Jackie. This would only serve to enforce Jackie's feminine persona.

They were currently driving across town for dinner. He was dressed in a new Armani suit, and Jackie was in a sexy black dress he had bought for her.

"How are you handling the hormones?" he asked.

"Everything seems to be going well. The liquid doesn't taste bad," replied Jackie.

"Don't be disappointed if you don't see any changes for a few weeks," stated Chris.

"I know, I wish I could just take a pill, and poof, be feminized," she stated.

"Where's the fun in that?" he asked and started laughing.

"True," replied Jackie. "I'll start wearing those slacks at work starting Monday. The only masculine clothes I'll be wearing are my jackets. I mean I'm wearing a blouse, a camisole, panties, pantyhose, sometimes stockings, women's slacks, and shoes. The tie and jacket are the only things male in my wardrobe, and still no one has noticed, other than Lisa."

"It'll get a little trickier when your body starts changing. You'll need to start wearing a bra; we can find styles that won't be so obvious, but we'll have to address the fact that Jackie will be replacing Jack. How strongly do you feel about your current job?"

Jackie thought about it before answering. "To be honest, I could take it or leave it. The work's not exactly exciting. I took the job to pay off my loans."

"I'll keep an eye out for other positions for you once you transition. I'm not talking about you becoming a secretary or anything like that - not unless you want to be mine," he replied with a laugh.

"Even if you were serious, I doubt if Mr. Chambers would go for that," replied Jackie. "Still, it would be fun."

Chris nodded. "It would definitely hurt my work production. Is there anything else you'd like to do? What was your major in college again?'

"I was a business major, but I took some classes in library science. I worked summers at the university in the library."

"How many classes are you from finishing a library degree?" he asked.

"I could do it in a year, if I went back to school fulltime, why?"

"Mr. Chambers is on the board of the city library. I bet he could get you a job if you wanted. It's a far better job for you anyway."

"You mean that?" she asked.

"Sure. You could enroll in the fall semester as Jackie. I'm willing to bet that you could start working for them now part time as you finish your degree."

Jackie nodded. "That's a very appealing idea. I must admit that I really don't like working in a cube."

"I know. I'm so glad that I'm a manager now. Well, we can look into getting you enrolled in the fall semester. By then, I doubt you'll look masculine enough to pass as Jack."

"I'd like that," she replied. The idea was very pleasing to her.

"But I thought you didn't want me to work fulltime?" she asked.

"I don't, but if you're working as a woman in a job like a librarian, I don't mind, just as long as you remember that you're my woman."

Jackie smiled. "I'll never forget that."

"Well, here we are. You'll love this place, they have the best seafood in town," stated Chris.

They walked in together and were taken to their table. Jackie couldn't help but notice the looks she got from some of the men as they walked to their table.

After ordering drinks, Chris turned to Jackie. "Are you seeing Tess tomorrow?"

"Yes. She's scheduled me for every Sunday afternoon for the next few weeks."

"Good. She's done a great job with you so far."

"Lisa suggested that I take dance lessons," said Jackie.

Chris thought about it. "That's a great idea."

"She said that it would help me with my demeanor."

"It will," he replied. "I wish I had thought of it."

"Do you dance?" she asked.

"I'm not too bad," he stated.

They both had the fresh halibut, and the dinner was excellent.

After dinner they went for a walk through the main downtown drag. He had his arm around her waist, and she cuddled close to him. To the rest of the world, they looked like a couple deeply in love, which was what they were.

Chapter 41


It was two weeks later that Jackie began to notice that she was changing physically. Her nipples were noticeably larger and definitely more sensitive. She stood in front of her mirror and ran her fingers over her nipples. She then turned slightly and noticed that it wasn't just her nipples that had grown, but that her breasts were growing. Granted, they weren't huge, but there was definitely some growth there.

She let out a long sigh of satisfaction in seeing that her body was changing.

Dr. Bonnet had told her that the changes would happen sooner than she had expected and she was right.

Jackie slipped on a pair of panties, followed by a pair of pantyhose. She adjusted her clitty to ensure it was tucked between her legs. Next came her camisole, which she slipped over her head. Jackie put on her blouse and then tied her tie. Her slacks came next flowed by her flats. She examined her image in the mirror and couldn't help but smile. Other than Chris and Lisa, no one had noticed her shift in wardrobe. She ran her fingers through her hair, it was still short, but it was growing out. She had an appointment to get it dyed and styled in two weeks. Chris eventually wanted her hair to be auburn.

She smiled thinking about Chris. They had made love the previous night, and she closed her eyes and sighed thinking about how wonderful it had been. She was so in love with Chris.

Jackie appreciated the fact that he didn't press her about her past feminine feelings. She wanted to tell him everything, but she wasn't quite ready to delve that deeply into her past.

Lisa picked her up, and they drove to work together. They'd started doing this a few days a week, and it gave them more time to talk.

Work was the only environment where Jackie was seen as male, as she changed as soon as she got home. This change happened even sooner on some days, as it wasn't that difficult to be seen as female.

This had been Lisa's idea, and Chris loved it and encouraged Jackie to do it. After she left work, Jackie would stop at a discrete place on the way home and remove her tie and jacket, put on makeup, her wig, jewelry, and a woman's jacket. It only took a few minutes, and Jackie could pass as a woman.

Lisa commented that once Jackie's hair grew out longer, she wouldn't even need the wig to transform.

Chris and Lisa had met several times to discuss Jackie's transition into womanhood. Lisa admitted that she loved the way Jackie was pushing the boundaries with her appearance and wardrobe. She even suggested that Jackie start wearing a slight touch of makeup at work, maybe a little eyeliner or some light colored lipstick. Chris liked the idea and suggested that Lisa be the one to start this phase of Jackie's change.

Jackie knew all about Chris and Lisa's plans for her. She didn't mind, in fact she loved the idea of being assisted in her conversion to female.

Jackie looked at the clock and saw that it was almost time to go home. It was Friday, and that mean she would be going out with Lisa that night. Tess would be joining them that night. Jackie had introduced Tess to Lisa the previous week, and they had hit it right off. They would meet at Lisa's before heading out to the clubs. Jackie couldn't wait.

Work had been the usual standard boring toiling on in her cubicle. While she still did her best, she had already started counting the days until she returned to college in the fall. While she wasn't officially accepted yet into the library program, it was looking good. It would be so enjoyable to be a librarian and not work in a corporate world, she thought, especially when she had Chris to come home to.

To Jackie's surprise, the fact that she was in transition didn't seem to faze the woman at the admission's office. She was more interested in Jackie's academic record and her ability to pay.

"Hey, daydreamer, you ready to have some fun tonight?" asked Lisa, as she stepped into Jackie's cubicle.

"I can't wait," she replied.

"You seem a little preoccupied today, what's up?" asked Lisa.

Jackie turned around and waved Lisa closer. She then leaned towards her and whispered. "I'm starting to see growth!"

Lisa smiled. "Cool. Those must be some seriously powerful hormones you're doing to see changes so quickly."

Jackie cringed. "Not so loud, please."

Lisa nodded. "Sorry, not that it'll make any difference in a few months."

"That's true, but until then I don't want to cause a fuss here."

Lisa smiled. "Well, we might as well leave. Everyone else has pretty much left already."

Jackie nodded, and after shutting down her computer, she got up and followed Lisa towards the exit. Lisa was carrying a large gym bag over her shoulder, in addition to her purse.

They walked past the ladies room and Lisa stopped. "Hang on." She then stepped inside.

Jackie waited outside for her friend. The office was pretty much deserted just as Lisa said.

Lisa stepped out of the restroom and grabbed Jackie by the arm and pulled her inside. It happened so fast that Jackie offered no resistance.

"What are you doing?" whispered Jackie.

Lisa pulled Jackie into one of the stalls and shut the door. "Sit down," she ordered.

Jackie obeyed and sat down on the toilet.

Lisa licked her lips and then set the bag down on Jackie's lap. She opened it up and began to apply makeup to Jackie's face.

"What're you doing?" asked Jackie.

"Trust me, sweetie," replied Lisa.

When she was done with the makeup, she had Jackie stand up and take off her coat and tie.

"I'm glad you wore this blouse today; it'll go with the scarf and jacket I brought in for you to wear," stated Lisa. "Oh, take off your slacks; I have a skirt that goes with this outfit."

Jackie just nodded and obeyed. She was slightly scared by Lisa's actions, but at the same time aroused.

Lisa pulled the clothes out of her bag, and in a few moments Jackie was dressed completely in women's clothes.

"What about my hair?" asked Jackie. "My wig is in the trunk."

"No problem. I have one for you to wear. It's a bit sexier than your usual one," replied Lisa.

Jackie didn't reply as Lisa pulled out the wig and styled it. "This has more curls than the one you usually wear."

Jackie was just glad that no one had come into the room.

Lisa finished Jackie's look with a few pieces of jewelry and a touch of perfume. "There, that's better. Jack is gone for the weekend; not that he was all here to begin with. Go out and see how great you look, I'll pack up this stuff."

Jackie obeyed and was amazed at her transformation. She looked like just another woman who worked at Chambers.

Lisa stepped out of the stall and handed Jackie a shoulder bag. "Here, you forgot your purse."

"I can't believe you did this," stated Jackie.

"You love it; you didn't even try to stop me," replied Lisa with a grin. "You know, I've been offered Chris's old job. If you decide that you don't want to be a librarian, you can come be my personal assistant."

Jackie laughed. "Chris already offered that I could be his secretary."

"Too bad. Well, we'd better get going."

"Um, what do we do if we run into someone?" asked Jackie.

"I'll just say that you're an old friend in from out of town. Trust me, no one will recognize you."

They walked out together, and Lisa started a conversation as if they were just two women leaving work together, which was in fact the truth.

"I still can't believe you did this," whispered Jackie as they approached Lisa's BMW.

Just then a man called out to Lisa.

"Hi, Lisa," he said.

It was Jim Harris from marketing. Jackie only knew him from a meeting she had once attended. He was a handsome, slightly stocky man, just starting to put on a little weight. He was thirty-eight and had once played college football at Brown. His brown hair was still thick, but starting to turn gray.

"Hi, Jim, have a nice weekend," replied Lisa.

"You too," he replied he then ran his eyes over Jackie. "So, are you going to introduce me to your friend?"

Without skipping a beat, Lisa nodded and turned to Jackie. "This is Jackie; she's an old friend of mine from college. Jackie, this is Jim."

Jackie smiled and shook hands with Jim. He smiled and stared directly into her eyes. Thankfully, before the conversation could get started, Lisa jumped back in.

"Jim, Jackie's been in town for a meeting and we're heading out to see some old friends, so I don't want to be rude, but we've got to go."

Jim smiled back. "Sure, I understand. Nice meeting you." As he walked away, he cursed his luck, as he was about to ask the redhead out to dinner.

Lisa and Jackie got into the car and drove off.

"Did you see how he looked at me? What a pig!" exclaimed Jackie.

"He's one of the biggest pigs in the company. I have heard that he's good in bed."

Jackie shook her head. "You've got to be kidding? Who would sleep with him?"

"I've known a few women who have," replied Lisa.

"He was practically undressing me with his eyes," continued Jackie with a disgusted tone.

"I would have liked to see the look on his face when he finished," stated Lisa who began to laugh.

Jackie started laughing too.

"Who knows, maybe he would want you even more?" continued Lisa.

Chapter 42


Chris watched Jackie and Lisa depart the parking lot from his office window. He was pleased that Jackie had gone along with Lisa's plan, although he was slightly irked that he hadn't thought of it himself. It was a deliciously dominant idea.

Lisa had cleared the idea with Chris the day before. She had talked to Chris in his office about her plan. She told him that she was happy to help Jackie expand her safe zone and boundaries.

"Jackie is so sweet; I can understand why you're so in love with her. I appreciate that you trust me to help you," stated Lisa.

"I should be thanking you, Lisa. I can only take her so far; she needs women in her life," replied Chris.

"She's very fortunate that she has you; a less caring person could really take advantage of her," replied Lisa.

Chris nodded. People like Jackie could be abused very easily if they fell into the hands of the wrong person.

"Like you, I need a submissive lover," replied Chris. "However, I don't want a slave, and I don't want to force her to do anything against her will."

"I know that, Chris," answered Lisa. "I talked to Tess and told her that if she gets another customer like Jackie that I'd like to meet her. There's something so delicious about a sweet submissive t-girl."

Chris smiled and nodded. "I'll drink to that."

"You really don't mind the fact that I've had sex with her?" asked Lisa.

"No, not at all. It only reinforces her femininity. I also like the idea of her having women friends to go out with. I also trust you to look after her."

"You can count on me, Chris. I'll make sure that she doesn't get hurt," said Lisa.

"I know that, Lisa," answered Chris.

Chapter 43


It was later in the evening, and Tess and Lisa were working on Jackie's makeup and hair. They were determined to make her look extra-seductive that night. The women were wearing silk kimono robes, a gift from Tess.

Under her robe, Jackie was wearing a body shaper. It had built in silicone pads that served to push up her small breasts.

"I just want to see the men drool over you," explained Tess, as she put eyeliner on Jackie. "The men at Anything Goes can be such macho pigs sometimes, and I love it when they unknowingly fall for a girl like you, Jackie."

"You go there often, Tess?" asked Lisa.

"Yes," replied Tess. "I like to take some of my clients there for a night on the town."

"Really?" asked Jackie.

"Have you ever had any problems there?" asked Lisa.

Tess laughed. "The owner of the club is one of my oldest clients."

The three women started to giggle.

"So, tell me, Tess, have you ever had one of your clients made?" asked Lisa.

Tess's face sprouted a look of indignation. "Please! I'm an artist. When I take one of my girls out, she's ready."

"Like me?" asked Jackie.

"Honey, I wish I could claim credit for you, but I can't," replied Tess. "As soon as I saw you dressed, I knew you were a real woman."

"Without being too nosey, how much do you make, Tess?" asked Lisa.

Tess smiled a wicked smile. "I made six figures last year. I have several very rich clients who tip very well. I could make more, but there's just so much I can do."

Lisa cocked her head. "You need a partner?"

"You mean it?" asked Tess, as she began to apply lipstick on Jackie.

Lisa nodded. "It would be fun. I've loved helping Jackie, and I've always had a soft spot in my heart for t-girls."

"It is a lot of fun. I screen all my clients so that I only help people that I like. That way, I don't have to deal with those who are just looking for a sexual thrill. Many of my clients just want to dress. It helps them relax. You'd be amazed at some of the people that I've helped. I have clients ranging from professional athletes to politicians," replied Tess. "If you're serious, we can get together and discuss it. I really could use the help. I need someone I can trust. Who knows, you might even quit your present job!"

"I wouldn't mind that," stated Lisa. "Okay, let's get this young lady properly dressed." She got up and walked to the closet to get Jackie's dress.

The dress they had bought for Jackie was a black spandex mini dress with a long-sleeved sequined jacket. It looked like it was painted on her. Her shoes were three inch pumps.

Jackie stood in front of a full-length mirror and checked herself out.

"Damn, you definitely have the legs for a dress like that," stated Tess. "How many pounds have you lost since you first saw me?"

"Ten," replied Jackie. She was admiring herself in the mirror and wished that Chris could see her right now.

"How have you lost ten pounds in just two weeks?" asked an astonished Tess.

"I've done it mainly by eating less," replied Jackie.

"Shit, that's so unfair!" replied Tess. "I've spent six months trying to drop five pounds!"

"Sorry," replied Jackie.

"Don't apologize, Jackie. I think you look great," said Lisa. "But now that you're a woman, weight loss will be a much bigger concern for you from now on, among other things."

"Well, now that Jackie's ready, we'd better get dressed," noted Tess, as she looked at her watch.

Tess was wearing a red halter-top mini dress, and Lisa was wearing a similarly styled coral colored dress.

"We're going to turn some heads tonight," stated Lisa, as she applied some gloss on her lips.

"You know, we should go to Vegas sometime. I have some great connections there, and we'd have a blast," said Tess.

"Oooh, I haven't been to Vegas in a while. I had a really great time there the last time," stated Lisa.

"Has the statute of limitations expired?" asked Jackie with a wink.

Tess giggled.

"Very funny. Maybe I should put you over my knee for that, but you'd probably like it - come to think of it, I'd like it too," replied Lisa with a wink.

"Okay, do we have everything?" asked Tess.

"Who's driving?" asked Jackie.

"No one, I got us a limo for tonight," replied Tess.

"Another client?" asked Lisa.

Tess nodded.

"Hmm, now I'm really interested in talking to you," stated Lisa.

"What about you, Jackie? I could use you too," stated Tess.

"How? I mean I'm just learning a lot of this myself," replied Jackie.

"We'll talk about it later," said Tess, as she looked out the window. "The limo is here."

Chapter 44


Limos pulling up in front of the club were a common sight, yet more than a few heads turned when Tess, Lisa, and Jackie stepped out of the Hummer limousine. They were immediately allowed in, even though there was now a line halfway around the block.

"That's so cool, they let us in without waiting in line," said Jackie.

"They think we're somebodies," stated Lisa.

"That's because we are!" added Tess.

They found a booth on the third floor, and a waiter brought over a bottle of chilled champagne.

"Will that be all for now, Ms. Wellington?" asked the waiter, as he filled the flutes.

"Yes, thank you," she replied. "Please put this on my tab." She then handed the young man some money as a tip.

The waiter bowed and left.

"Wow, now I'm really impressed," stated Lisa.

"It's not like this everywhere; still it is a lot of fun to be wined and dined," replied Tess.

Jackie sipped her champagne. She smiled as she thought how dramatically her life had changed in the past few weeks. She had gone from being a lonely young man to having a boyfriend and an active social life with several good friends.

As the night progressed, the three friends laughed and talked. They were very popular, and they all ended up on the dance floor. Jackie was still a bit uncomfortable dancing, more because she knew she wasn't very good, and she didn't want to draw any undue attention to herself.

By one, they had made their way up to the top floor. A jazz quartet was playing softly in the background.

"I have to agree with you, Jackie; you're a really bad dancer. The cool thing is that most men don't care," stated Tess.

"Did you ever dance when you were Jack?" asked Lisa.

"Only when I was well lubricated," replied Jackie.

"We're planning on taking some dance lessons," stated Lisa.

"That's a great idea, what kind?" asked Tess.

"I want to start with salsa. There's a dance club that has salsa nights, and I've always wanted to go," replied Lisa.

"I want in on that," said Tess.

"The next class cycle starts in two weeks," replied Lisa.

Tess turned to Jackie. "How're you doing?"

"Tired, but I've had a wonderful time tonight."

"I know the feeling. Honey, I just want to tell you that I've never seen someone transition so quickly. It must be hard for you to go to work as a man," said Tess.

"She's barely a guy at work," interjected Lisa, who then went on to tell Tess how Jackie dressed.

"That's cool, but it's still a charade that you have to play. I bet you can't wait until you're a woman all the time," remarked Tess.

"I can't wait. Thankfully, I have Lisa at work, and that makes it tolerable, along with Chris," replied Jackie.

"You want a different job?" asked Tess.

"Doing what?" asked Jackie.

"I need a personal assistant," she replied. "I need someone to run the administrative side of my business, my schedule and things like that. You wouldn't be stuck behind a desk either. I need someone to also run errands for me."

"Like what?" asked Jackie.

"I need people to pick up clothes and makeup for me. I have some great connections around town with many boutiques and suppliers, and it just takes up too much of my time dealing with them. I think you'd be perfect for the job. You'd have to dress professionally and feminine, and I think it would be a great experience for you," stated Tess. "Now, you don't have to make up your mind right now, but think about it."

Jackie nodded. This was very intriguing, she thought. She also wondered what Chris would think of this idea.

"It wouldn't be a fulltime position, but you'd get a good salary, and it would be a lot more fun that sitting in a cubicle," continued Tess.

"It does sound appealing."

"You'd love it, and everyone I deal with is very cool," added Tess. "Now, what about you, Lisa?"

"I'm listening," replied Lisa as she sipped her drink.

Tess smiled. "I could use you fulltime. My studio is large enough for both of us to work on clients at the same time. I run the gauntlet from men just coming in to dress for the first time to regulars who want to go out shopping, or to dinner, or clubbing. Unfortunately I don't have the time to schedule them all. You have the right attitude, and I'd love to bring you in."

Lisa nodded and they began to talk details.

"Look, why don't I bring you in part-time, and we'll see if you like it, how does that sound?" asked Tess.

"It sounds great," replied Lisa. "So how did you get into this line of work?"

Tess laughed and motioned for the bartender for a refill. "I went to beauty school after high school. I was working in a salon and was making just enough money to pay off my bills. I quickly acquired a loyal following of customers and began to think about opening my own place. The trouble was I was broke. I was twenty-two and still living at home. I came home early one day and caught my sixteen-year-old brother in my room dressed in my clothes. He looked ridiculous and was terrified about being caught. He fell to my feet and began bawling. I calmed him down and we talked. He told me that he had these urges to dress in women's clothes. I told him that I still loved him and wouldn't tell anyone. I then dressed him up, and she became a very hot looking girl."

"What happened next?" asked Jackie.

"I started doing some research and found there was a huge market for transformation services. I was able to get enough money together to start a small service, and five years later I bought my studio. I now have a house and a car. Not bad for someone who was once living paycheck to paycheck."

"What about your brother?" asked Jackie.

Tess smiled. "He's not like you and has no intention of going fulltime. He still dresses, and we're still great friends. He found himself a girlfriend who accepts that he occasionally likes to be women's clothes."

"Does he live around here?" asked Lisa.

"No, he moved down to LA and tends bar in a club in West Hollywood," replied Tess.

"Wow, that's a pretty incredible story," stated Lisa.

"I'm still amazed that you never dressed before we met, Jackie," stated Jackie

Jackie's eyes dropped down and she bit her lip.

"You ready to talk about it?" asked Lisa.

Jackie nodded. "But not here."

"I'll call for the limo," said Tess.

Chapter 45


Back at Tess's place, the three friends had changed back into the robes and were sitting on the couch drinking wine.

Jackie took a deep breath. "First off, I want to say that I loved both my parents. They were wonderful and treated me great; the problem was that we moved around a lot. My dad was an engineering troubleshooter. He often had to go off to some remote part of the world for months at a time. Mom and I sometimes lived in hotels as we waited to see if this was the place where were would live permanently."

"How often did you move?" asked Lisa.

"I remember moving seven times," replied Jackie. "Anyway, I had a great upbringing, but it was lonely for both my mom and I. It was hard for both of us to make friends." Jackie then looked away as if she was looking off into the distance.

"You okay?' asked Tess.

Jackie nodded. "It just hit me how much I miss her. Anyway, one day, I think I was five, I was alone in our suite and a strange urge overcame me. I went into my mom's room and began to look in her dresser drawers. The touch of the clothes sent a strange feeling through me, and before I knew it I was putting her clothes on. Of course, everything was too big, but it felt so good." Jackie had a big smile on her face.

"Did she catch you?" asked Lisa.

"Not for a while. I only did it when she was out, and I thought I was very careful to put everything back exactly where I took it," replied Jackie.

"How'd she catch you?" asked Tess.

"Looking back, she was really sweet about it. She came into my room and sat down on the edge of bed. I think I was seven at the time. She asked me if I had been in her room. At first I denied it, but she put her arm around me and told me it was okay to talk about it. I broke down and began to cry, she just pulled me close and hugged me."

"She sounds like she was a wonderful woman," stated Lisa.

Jackie wiped away a tear. "Thanks, she was. Well, after I was able to talk, we discussed my feelings. I told her that I wanted to be a girl. Instead of being upset, she just smiled and hugged me. The next day she brought me into her room, and there was a whole wardrobe of girl's clothes on her bed."

"Really?" asked Lisa.

Jackie nodded. "She told me that it would be our secret and that she would help me discover who I really was."

"Did she ever tell your dad?" asked Lisa.

"Yes. He was confused at first, but he didn't stop her from allowing me to dress," replied Jackie.

"Did he ever see you dressed?" asked Lisa.

Jackie nodded and wiped away another tear. "He just smiled and told me that I was a pretty little girl." Her voice cracked as she spoke.

"That's so sweet," stated Lisa, who was starting to tear up.

"Did you ever go out dressed?" asked Tess, as she handed Jackie another tissue.

Jackie shook her head. "No, we kept it in the house. I only dressed when Mom said it was okay. I think she suspected that I was transgendered; we talked about taking it to the next level... but then it all came to an end."

"What happened?" asked Lisa.

"Dad took a job up in Alaska. He worked up there on and off for two years. He was finally offered a fulltime position. He took mom up there to see what it was like. I was staying with my aunt in New Jersey. My girl clothes were in storage along with most of our stuff," said Jackie. She took a deep breath and let it out. She had to wipe the tears from her eyes before she could speak. "They never came back." She then began to sob.

Tess and Lisa held onto Jackie as she cried and let out the years of grief. Eventually, Jackie regained her composure and wiped her eyes.

"Thank you. Anyway, I blamed my wanting to be a girl for what happened to them. They were punished because of me. At their funeral I decided that I would never submit to those feelings again. I pushed them all away. It was surprisingly easy to do, as I had other problems to deal with. I was passed around by my family until I left for college. By then, I had been so successful in my denial that I convinced myself that I had never dressed," continued Jackie.

"So you were in denial all these years?" asked Tess.

Jackie nodded. "Anyway, my memories have been coming back with a vengeance."

"Have you told Chris this?" asked Lisa.

Jackie shook her head.

"You need to," replied Lisa.

"I know. You two are the first people I've felt comfortable talking to about it," stated Jackie. "I'm just feeling comfortable thinking about it.'

"You need to see a therapist, Jackie. You should be seeing one anyway concerning your transition, but these are some heavy issues you're dealing with. I think it's wonderful that you trust us, but this is something serious," commented Tess. "I have the name of a very good therapist who specializes in gender issues."

Jackie nodded. "Can I have her number?"

Tess leaned over and hugged Jackie and was joined by Lisa.

Chapter 46


The next day, Jackie drove over to Chris's place. She was wearing a short denim skirt and a sleeveless t-shirt. She knew she needed to tell her lover her past.

Chris sat and listened as Jackie sat across from him and told him her past.

When she finished talking, she again broke down and cried. Chris didn't say a word and pulled her close and hugged her. He rocked her gently in his arms and let her sob.

"So, do you still love me?' asked Jackie softly in a voice barely above a whisper.

"More than ever, my dear," he replied. "It explains so much about you. I promise that I will take care of you and that you'll never be alone again."

Jackie smiled and wiped her tears with a tissue. "I just want you to know the truth about me and that I'm dedicated to the transition. I have no regrets, and I love you with all my heart."

"I appreciate you telling me that," replied Chris. He still suspected that she was repressing some feelings, but he was willing for her to let these out on her own.

"I also want you to know that I trust you, and I want to continue on the path that we started on," continued Jackie. "I want to submit to you. I love how you control me in a loving way."

Chris smiled. "You have no idea how happy it makes me feel to hear you say that."

Jackie cuddled up close to Chris, and he began to softly stroke the back of her head. He then gently positioned her and began to kiss. They were both soon aroused and in a sexual frenzy. He guided her head down between his legs and let her begin to suck his cock. He held her head as she bobbed up and down on his cock. His touch served to increase Jackie's pace, and it didn't take long before he came.

Chapter 47


Over dinner, Jackie told Chris about Tess's offer.

"Does that interest you?" he asked.

"It does. I like the idea of working for Tess and helping others who are dealing with gender issues," said Jackie.

"So do I. I think it would be great for you to interact with other women besides Tess and Lisa. I can also see you as a librarian. What I like about both jobs is that you'll have to interact with other people," said Chris.

"So I could do either job?" asked Jackie.

"How about you work for Tess and take one class a semester? That way you could do both," suggested Chris.

Jackie smiled and wrapped her arms around him and kissed him. "Thank you so much!"

Chris kissed her back. He was very pleased with the job offer from Tess; it was better than anything he could have imagined. Both Tess and Lisa were dominant women, and they would nurture Jackie's submissiveness.

"How soon did Tess say you could start?" he asked.

"She didn't say, but I suspect she would take me as soon as I was available," replied Jackie.

"I think you should call her and ask her right now. That way, you can put in your two weeks notice to Chambers," he stated. This would also mean that Jackie would have no reason to portray Jack at all.

"You don't mind?" asked Jackie.

Chris shook his head. "No, it means that you would be Jackie all the time from now on."

Tess was excited that Jackie accepted her offer and said that two weeks would be perfect.

"I'll expect you to dress in a certain manner, and I'll be happy to help you shop for your new wardrobe," said Tess. "This is going to be great; I'm so happy that you'll soon be my assistant."

"Great. Now all I have to do is tell my boss," replied Tess. "I promise I'll do a great job."

"I have no doubt you will, Jackie, otherwise I would have never offered you the job," replied Tess. "We'll get together this week to discuss the details."

"What about Lisa?" asked Jackie.

"She called me a few minutes ago, and she's agreed to initially start working for me part-time. She wants to ease out her job at Chambers," replied Tess.

"I feel a little bad that they're losing two employees to you," stated Jackie.

"It only makes sense. I've had several of their employees as clients," replied Tess with a giggle.

Jackie laughed and then set a time to get together with her future boss.

She hung up the phone and turned to Chris. "I got the job."

Chris smiled back. "Was there ever a doubt? I'm so proud of you, my sweet."

Chapter 48


Jackie sat nervously in the waiting area outside Mr. Chamber's office. Her letter of resignation had been accepted the previous day by Chris and passed up the chain of command.

She was dressed in her mainly female outfit. She was wearing navy slacks, a light blue blouse, a tie, and a jacket. She kept her feet together on the ground, afraid that if she crossed her legs her stockings would show.

Lisa had compared her outfit to the Emperor with No Clothes. All it would take would be for one person to notice her outfit and to say something.

There was a buzz at the intercom of Mrs. Boisvert, Mr. Chambers' secretary.

"You can go in now, Mr. Easton," she said. There was a slight French accent to her voice. Chris had said that she had been born in Quebec.

"Thank you," she said as she got up and entered her boss's office.

"Please site down, Jack," stated Mr. Chambers.

Jackie obeyed and sat down in the plush leather chair across from Mr. Chambers.

"I received your letter this morning, and while I can't say I'm surprised, I'm sad to see that you're leaving. Still, considering what you're going through, I'm not all that shocked. Besides the obvious, what are your plans?" he asked.

"I've accepted a job as a personal assistant for a woman who runs her own business. She needs someone to run the administrative side of her business," stated Jackie.

"Good. I was worried that you be forced to take a lesser job. If you change your mind and want to come back, I can always find a position for a hard worker like you."

"Even if it's Jackie who applies?" she asked.

"Of course," he replied. He then looked carefully at Jackie. 'I'll be damned, are you wearing a blouse?"

Jackie nodded. "Land's End."

"And, of course, no one has noticed," he stated.

Jackie smiled as she nodded. "Only two others."

"I guess we accept what we see at face value. Now that I look at you, I can see other changes. I can't blame you; it must be awful to deal with that sort of conflict. Well, I wish you all the best, Ms. Easton, and thank you for your short, but productive time here."

He stood up and shook Jackie's hand.

"Oh, by the way, don't hesitate to call me, if you need anything," he added.

Jackie wasn't sure if he meant it or was just being polite at first, but the look in his eyes told her that he was serious.

"Thank you, sir. I appreciate your understanding," she replied.

She turned and started to walk away, and then she turned around and held out one leg, showing her pantyhose and woman's shoe.

Mr. Chambers laughed. "I'll be damned. It's just like in the Shawshank Redemption - how often do you look at a person's shoes?"

Jackie smiled and left his office. In a way she felt sad about leaving, but she was also excited about her new job.


Chapter 49


"I always knew Mr. Chambers was cool," stated Lisa over lunch.

"He reminds me of my dad in some ways," replied Jackie. "So when do you start working for Tess?"

"She's showing me the ropes this Wednesday night. I'm going to assist her for a few weeks until I go solo. She says that it's just not the makeup and dressing, but there's a way of easing their fears and making them feel at ease."

"I know you'll be great. It's going to be so cool working together with Tess," stated Jackie.

"Yes, it should be both fun and very profitable," said Lisa.

"That's true," replied Jackie. "I'm just happy to have a job where I can be myself and don't have to work in a box."

"I know. I'm not going to miss the office myself. The only thing that has made it tolerable the past few weeks has been you," said Lisa. "So, are you up to going out this Friday?"

Jackie nodded. "I wouldn't miss it for the world."

Chapter 50


Tess nodded with approval as Jackie modeled a linen suit.

"That looks great on you," Tess commented. "I know it's a bit more formal than you like, but you're going to need a variety of wardrobes as my assistant."

"I like it, it's very classy looking," replied Jackie.

"Some of my clients go for the very high end styles, and what's more important, they're willing to pay for their outfits," continued Tess.

"Do you pick out the outfits for them?" asked Jackie.

"Depends on the client, some have no idea what they want, others know the exact style; it can be pretty interesting. Part of my business is as wardrobe consultant, and it's pretty lucrative. My rate changes depending on the client and the style of clothes they want," explained Tess. "Eventually, you'll get to meet all my connections, and you'll need to be dressed appropriately."

"Sounds like fun," replied Jackie.

"It can be. You mentioned that you were interested in being fitted for a corset; I have a really good friend who makes them. I send her a lot of business, and I think it would be great if you met her and also became her client."

"I'd like that. Do you wear a corset?" asked Jackie.

"Sometimes. It depends on my mood."

Jackie changed out of her outfit, and after paying for it they stopped for lunch.

"So what do you do for fun?" asked Jackie.

"Well, since you're going to working with me, I guess there's no harm in you knowing. I'm into the B&D scene. I have a few friends that I like to play with; it helps me relax. I'm not looking to get into a serious relationship with anyone or anything like that. I go to the occasional party, and sometimes all I do is watch others play."

"Do you know someone named Mona?" asked Jackie.

Tess nodded her head. "She's pretty extreme. How do you know her about her?"

"She did my piercing," replied Jackie.

"Of course. I bet she drooled over you," said Tess.

"She's a little scary."

"True, but she's also level headed. If you ever decide to go to one of her parties, you have to be screened. You also need a safe word."

"Safe word?" asked Jackie.

"Yes. The best bondage scenes press your comfort zone, but you also have to remember that it's not real, meaning that it's still just play. There are people who really live the lifestyle, but they're the exception. A safe word lets your partner know when they've gone far enough. I won't do a scene without one, and neither should you."

"Chris has mentioned that he'd like to try some things like that, but he says he wants to make sure that I'm ready," replied Jackie.

"That's smart."

"Without getting too personal, what do you like to do?' asked Jackie.

Tess smiled. "I can go both ways, sub or dom, depending on the other person. I can also do it with men or women, although I prefer other women."

"I guess I'm strictly submissive now; I can't imagine being in charge with someone now," stated Jackie.

"That's cool, and you're lucky to have someone like Chris. He seems very intelligent and safe. I think what really turns him on about you is that he doesn't have to force you into anything. That's a wonderful relationship to be in; I'm very happy for you."

Jackie smiled back. "Thanks. So what else do you like to do for fun?"

Tess laughed. "I love going to see plays and opera. I go to New York City once a year to see a few plays on Broadway."

"That sounds like fun," replied Jackie.

"I also go to Vegas a few times a year. Sometimes it's on business, as I have a few clients there, but I love seeing the shows and I'm also a pretty savvy blackjack player. We should do a girls-only weekend down there sometime, you, me, and Lisa. It would be epic."

"I'd like that."

"I'm so pleased that you're going to work for me. I want to help you fulfill your true self. I see so many men who cannot become the woman they were meant to be, and it gives me a good feeling to see you reborn."

 
Chapter 51


It was two weeks later, and Jackie was completing her first week as Tess's personal assistant. Part of her job was office administration and organization, not that different from her old job. The other part was far more interesting.

In between seeing her clients, Tess took Jackie around town and introduced her to a variety of people. Many were women and men who ran boutiques and shoe stores. Most were mainstream, but there were those who ran fetish clothing shops.

What struck Jackie was how nice and normal they all seemed, much more pleasant that many of her old co-workers at Chambers. The first thing that struck Jackie was that they all remembered her name.

While Tess was Jackie's friend, she was also her boss, and Tess was a very demanding boss. While others might rebel against her strict standards, Jackie reveled in them. Her submissive nature was perfect for her position.

Chris was also pleased with Jackie's new job. He had talked to Tess several times and knew that she was the perfect boss for his lady.

It was late Friday afternoon, and Jackie was reviewing Tess's weekend schedule before printing it out.

"Lisa is going to be helping me tomorrow; I can't wait until she comes on fulltime," stated Tess.

"There, it's done. You have two appointments tomorrow, one at two and the other at six," stated Jackie as she handed Tess the schedule.

Tess looked at the schedule and nodded. "I like both of these guys. The man at two comes in every month. He lives up in Seattle."

"What about the other one?" asked Jackie.

"He's also a regular. He sees me every month too. I'll help him dress and do his makeup before he goes out to his support meeting. The poor guy, it's his only chance to dress. Next week, I'll start you on reviewing my client files, so you can anticipate my schedule. There are some clients that I think Lisa would be great with too."

Jackie nodded. The clients' files were currently locked in a safe in Tess's office. One of Jackie's tasks in the next few weeks would be to transfer them all onto a secure computer drive.

"I'm sorry that Lisa and I won't be able to go out with you tonight," stated Tess.

"It's okay. Chris is going to take me out to dinner. He wants to celebrate my new job," stated Jackie.

"So have you disposed of the last of your old wardrobe?" asked Tess.

"All but one outfit. I'm going to have a little ceremony with it when my name change comes through. I plan on burning it along with my old driver's license."

Tess laughed. "Well, give Chris my love and have a wonderful time tonight."

"I will."

Chapter 52


Chris took her out to a nice little bistro for a candlelight dinner. During dessert he leaned over the table and kissed Jackie.

"I just wanted to say how proud of you I am. You've totally changed your life, and I'm so lucky that you're part of my life," stated Chris.

Jackie smiled back. "I can't believe how everything has worked out. I'm so happy being a woman and especially being your woman."

Chris reached over and gently took her hand and slipped a diamond engagement ring on her finger. "This is to show you how much you mean to me."

Jackie stared down at her hand and the stunning ring on her finger. She could feel tears welling up in her eyes, and her lips began to quiver.

"Well?" asked Chris with a smile. "Do you like it?"

"I love it," replied Jackie.

"I know our relationship is different, but I want you to know that you mean the world to me. I also want you to know that this isn't a fling to me; I want you in my life. I need you in my life."

Jackie stared into his eyes and smiled back. "I love you so much."

"I think we should head home," stated Chris.

They made love on the couch in front of the fire. The sound of the rain outside only made it more romantic as Jackie cuddled close to her lover.

"I have something that I want tell you," stated Jackie.

Chris slipped his arm around her and pulled her close. He had expected this. "Go on, my dear."

"I told you how my parents let me dress and that I stopped after they died. I didn't tell you everything," stated Jackie. "I did dress a few more times."

Chris nodded. "I'm not surprised; it must have been difficult to stop."

"It didn't turn out well. After my parents died, I moved in with my aunt and uncle. Uncle Ron was my dad's brother. Aunt Joan wasn't that happy that I was living with them. They had two girls, one was older than me. After living with them for six months, the feelings got too strong, and I snuck into my older cousin's room and swiped some clothes."

Chris gently ran his hand through her hair.

"I did this a few times... until I was caught by Aunt Joan." Jackie's voice tailed off.

"Go on, my sweet, you need to let this out."

Jackie took a deep breath. "I came home from school, and she came into my room and told me she knew I was a sick little sissy pervert, and then she whipped me with a belt. She beat me until I was sobbing. She then told me that I was going to hell and that unless I stopped my parents would also be thrown into hell. She told me that if I ever did it again, she would tell everyone in town and some real boys would beat me senseless. I begged her and promised that I would never do it again."

Chris reached over and wiped the tear running down her cheek away. "Is that it?"

Jackie shook her head. "She beat me regularly and told me it was my punishment for sins. Two months later, I was sent to live with another relative. Aunt Joan told me that she would keep an eye on me and that if I strayed she would expose me."

"And you were what, ten?" asked Chris.

Jackie nodded.

"You poor girl," he stated as he kissed her.

"I guess the abuse and fear that she put me through helped me repress my feelings. I made myself believe that none of it had ever happened," continued Jackie.

"Is she still alive?" asked Chris.

"Yes, although I haven't talked to her in years," stated Jackie. "I can't believe she was so mean to me."

"Mean doesn't even start to describe her; she sounds like a first rate bitch," stated Chris.

Jackie smiled and then began to giggle. "Maybe I should send her a photo of what I look like now. I bet she'd throw a fit."

"That sounds like a plan," stated Chris. "But for now, I think we should just make wild love until we pass out."

"I love that idea," replied Jackie.

The End — for now
Notes:

 

Readers, Please Remember to Leave a Comment

Feel free to submit ideas on potential clients for Tess, Lisa, and Jackie in the further adventures at Tess's Transformations.

 

up
86 users have voted.
If you liked this post, you can leave a comment and/or a kudos! Click the "Thumbs Up!" button above to leave a Kudos

Comments

Another Great Story From Julie

Breanna Ramsey's picture

First I will say that this type of story is not what would usually appeal to me. That's just a matter of personal tastes. And I confess if it had been under a different author I would have passed it by, but I am always on the lookout for something new from Julie.
Well, Julie made it work for me. It was touching and compassionate and it made me again long for the world as Julie creates it. There's nothing wrong with being outside the norm...normal is overrated anyway. In the end, all most of us really want is to love someone and have someone to love us. Jackie and her friends have that and they are so much the better for it.
Great work Julie, thanks for passing the love to all of us.
Sincerely,
Scott

Bree

The difference between fiction and reality? Fiction has to make sense.
-- Tom Clancy

http://genomorph.tglibrary.com/ (Currently broken)
http://bree-ramsey314.livejournal.com/
Twitter: @genomorph

D/s stories are not my usual

D/s stories are not my usual reading but Julie made this one work pretty well. I enjoyed it, and hope to see more. Good job.

A Standing "O"vation

Julie,
I just wanted to say that I enjoyed this story a lot. I really like your Allie Burns stories the most, but this was well-written and nicely plotted. Maybe Jackie exploded out of Jack a little faster than I was expecting; but that's not bad, just interesting.
I noticed that a couple posters had commented on the D/s aspect in your story, and that got me thinking. There's a lot of that, implicitly or explicitly, in most (but not all) of your stories. The sexual predators that Allie Burns tracks down. The way that Hallie becomes female. Iona and Keir. The things that have happened to Beth. And some much more explicit D/s and S&M in a couple of your more recent stories. So this seems to me like a natural extension of your writings.

Love,
Diane

Love,
Diane

Tess -

As usual, Julie, you have written an engaging story.

I freely admit that the D/S aspect is well outside my usual area of interest, but you've made the concept flow seamlessly into the story.

I tend to agree that the Jack to Jackie transition was more rapid than I'd expect; on the other hand, given Jack's background, when the wall began to crack it could reasonably collapse quickly. The Willing-Suspension-Of-Disbelief is minimal.

Good work!

Itinerant

Nicole (a.k.a. Itinerant)

--
Veni, Vidi, Velcro:
I came, I saw, I stuck around.