BigCloset Classic

Skirting the Law
Date: Sunday, August 22 @ 22:59:05
Topic Big Closet TG Stories

To avoid getting a pink slip, a lawyer decides to wear one.

Skirting the Law

&copr;2004 by Nom de Plume

Effective January 1, 2004, Assembly Bill 196 amended California's Fair Employment and Housing Act to prohibit discrimination based on a person's perceived identity, appearance or behavior, even if they are different from a person's sex at birth. AB 196 is primarily intended to prohibit discrimination against employees who choose to dress like the opposite sex and or portray the stereotypical characteristics of the opposite sex. Businesses cannot refuse to hire based on cross dressing, neither can they fire, lay off or refuse to give merit raises based on an employee's real or perceived gender.

Charles Bigelow threw the article down on his immaculate mahogany desk and snorted. "What a load of crap," he said as he reached for the phone. "Get whoever's in charge of the legal department these days, and Wallace in Human Resources. And see if you can find a conference room that's available for a meeting in fifteen minutes."

Bigelow's executive assistant knew when the old man was in a bad mood, and today was one of those days. As she flipped through her directory, she wondered what had set him off this time. Another round of disappointing earnings reports? The company's financial problems were no secret, and it was rumored that heads were going to roll in the executive suite if the ship of state didn't turn around soon.

The company's general counsel had quit after a blowup with Bigelow over records destruction, and two of his assistants had already tendered their resignations in the aftermath. She ran her finger down over the scratched out names until she came to Terrence Poindexter, with the words "acting general counsel" penciled in next to his name. Better call him fast before he joined the exodus.

* * *

Bigelow and Helen Wallace were waiting in the conference room when Terrence Poindexter arrived, a few minutes late, carrying a yellow legal pad and a handful of pencils. A back room boy all the way, he was much more comfortable surrounded by a pile of law books than by a room full of corporate executives, and he fidgeted nervously with one of his pencils as he waited for Charles Bigelow to start the meeting. It didn't help that Bigelow seemed to be staring right through him, dissecting him from his pony tail and bow tie to his khakis and Birkenstocks. When Bigelow finally cleared his throat to speak, Terrence almost jumped out of his skin.

"I just learned about the latest insanity from Sacramento," he said, pushing copies of the article across the table. "Does this mean what I think it means?"

Helen skimmed the article while Terrence seemed to be studying it word for word. Please God, let him speak first, she said to herself, knowing Bigelow's penchant for shooting messengers on sight. Her prayer was answered when Terrence put down the article and tried to answer the question. "I don't know what you think it means," he began in his soft lisping voice, "but I can tell you what the legislature intended. Basically, if an employee should decide one day to show up dressed as a member of the opposite sex, the company cannot discriminate against him, or her, as the case may be. The same holds true for job applicants."

"Let me see if I have this straight," Bigelow retorted. "If a three hundred pound man shows up for a job interview in a dress and high heels, are you telling me we have to hire him?"

"No, but you can't base your decision on his appearance."

"As a practical matter," Helen cut in, "we can base our hiring decisions on other criteria, so I think we can work our way around that."

"As long as the paperwork backs us up, you're right," Terrence said. "The bigger problem is with current employees."

"What do you mean?" Bigelow challenged him.

"Well, suppose one day one of our male employees decides to show up in a dress. Under the new law, we can't fire him, and we may even have to make some reasonable accommodations, such as restrooms...."

Bigelow erupted. "Are you telling me that I have to turn our business into a drag show?"

"Well, no sir," Terrence stammered. "For one thing, this may never come up...."

"Are you kidding? We're in San Francisco, for Christ sake. It's only a matter of time before one of those ballerinas in the marketing department decides to come dancing out of the closet!"

"Well, in that case, the law is clear," Terrence said. "We have to accept them and learn to deal with it."

Helen closed her eyes. She couldn't bear to watch. "If I started to run our business based on legal advice like that, we'd go straight down the tubes!" he shouted.

"Based on our latest earnings reports, I'd say we're headed there already," Terrence said, surprising himself as he said it. Helen sat and stared at him with an open mouth.

Bigelow would have loved to fire Terrence on the spot, but lawyers were tricky. The last thing he needed was to be slapped with another wrongful termination suit. His face was beet red when he got out of his chair. "Helen, I'd like to meet with you in my office. Alone."

* * *

Terrence was still shaking when he returned to his small, cluttered office in the bowels of the legal department. He had declined offers to move into the larger offices of his departed colleagues, not wanting the pressure that would come with them, and knowing that such a move would only have been temporary.

It was all academic now, of course. He was toast. Charles Bigelow was probably reviewing his personnel file with Helen right now, scheming to find a bullet-proof way to terminate him. He looked at the article which he'd brought with him from the conference room, and he was about to file it away when the idea entered his mind.

At first, he dismissed it as absurd. What he really needed was enough breathing room to hang onto his job until a new general counsel could come on board, evaluate his qualifications, and protect him from the wrath of Charles Bigelow. But the more he thought about it, the more he realized that his career had been hopelessly damaged. What new executive would want to expend valuable political capital defending an employee against his own CEO? No, he had to face reality. His career at Tyrex Industries was finished, and under the severance guidelines which he himself had drawn up for Helen Wallace, he would be entitled to a lousy three months' salary on his way out. That wouldn't keep the wolf from the door very long in a city like San Francisco.

Terrence began to think like a lawyer. If there was no hope of hanging onto his job, the best he could shoot for was some grounds for making his termination a wrongful one. If he could put the company on the defensive by trumping up grounds for a discrimination action, for example, he'd be off to the races. As a white male from an Ivy league law school, Terrence Poindexter wasn't your average plaintiff in a civil rights case. He looked at the article again and smiled to himself when he found the passage he was looking for: "AB 196 is primarily intended to prohibit discrimination against employees who choose to dress like the opposite sex." The plan of action was simplicity itself. But would he have the balls to pull it off?

* * *

After telling Human Resources that he was going home sick, Terrence left the office as quickly as possible. The key to his strategy was to strike first, by putting himself in the position to claim discrimination when his termination notice was received. Knowing Charles Bigelow, he reckoned he had very little time.

Terrence had seen the advertisements many times on his way to and from work on the Muni, and sure enough, he found one of the ubiquitous placards on the back of a park bench. In the past, he had ignored them, but today he took out his cell phone and punched in the number below the pitch: "The House of Fabulous for boys who should have been girls. No assignment too challenging. Complete confidentiality guaranteed. Call today for your own personal makeover." The text was accompanied by a picture of a beautiful girl, evidently a guy, which some vandal had defaced with a mustache and goatee. Terrence went straight to the point when a woman answered the phone.

"I need a personal makeover. Today."

"Oh dear, I'm afraid that won't be possible. We're booked up through the end of the week."

"What do you charge for a makeover?"

"Well, it depends on what you want. We have a menu of services. For an initial transformation, for example, we charge $500. We also offer wardrobe consultation and a complementary shopping service, as well as a host of other options."

"I'll double it."

"I beg your pardon?"

"I need a complete makeover, today. Time is of the essence. I'll pay double your standard fee, and pay a percentage on the wardrobe. Please, you've got to help me. I'm desperate."

"If it were just the money, I would have to say no to you. But you do sound desperate, and we are in business to help our customers. If you can stop by at four o'clock, I'll see what we can do. What is your name?"

"Terrence. The stores are open till nine. Will that give us enough time?"

"Goodness. I suppose that depends on what we have to work with."

* * *

Terrence went home to his apartment and tried to think of what he might do to expedite his transformation. He pulled his hair out of its ponytail, and watched with approval as it fell almost to his shoulders. When he took off his clothes, he realized immediately that the first thing he had to do was remove his body hair. All of it.

It took him almost two hours, wearing out razor after razor as he tediously worked his way over his chest, back, legs and arms. There were more than a few cuts, and some places that he just couldn't reach, but by the time he finally rinsed himself off in the shower, the parts that would show were smooth and hairless. He shampooed and conditioned his hair, taking a lot more time than usual drying and brushing it out, before he put on a pair of jeans and a sweatshirt and made sure his wallet was stuffed with cash.

Terrence decided to skip lunch, and he planned to skip dinner as well, even though his stomach was growling. At 5' 9" tall and 150 pounds, he was slim for a guy, but big for a woman. He began to believe that if the House of Fabulous was as good as their advertisements, he actually had a shot at being presentable. As soon as he walked into Tyrex Industries, he would be an object of scorn, but that didn't mean he had to subject himself to ridicule when he was out on the street.

Before leaving his apartment, Terrence placed a call to Gail Chestnut, who was acting as his executive assistant pending the appointment of a new general counsel. Gail was a knockout, but most of the guys in the office had written her off as a lipstick lesbian after she turned down their advances. Terrence thought she was incredibly hot, but as a company lawyer, he knew better than to mix sex with the workplace, so he hadn't even tried. "Gail, I need to ask you a favor," he said when he got her on the phone.

"What can I do for you, Mr. Poindexter? I hope you don't have the flu."

"I'm feeling much better, thank you. I'll be in tomorrow for sure. Gail, remember how the office manager suggested that I move into the big office until we get a new general counsel?"


"Well, I've changed my mind. I wonder if you could arrange for my stuff be moved in tonight. Not all my files, just my laptop computer, diary, and personal things. "

"I'll get right on it. Mr. Poindexter, have you checked your voice mails?"

"No, I haven't."

"Mr. Bigelow wants to meet with you in his office at nine o'clock tomorrow morning."

"Please go ahead and confirm it. I'll see you first thing tomorrow."

"What made you change your mind about the office?"

"Let's just say I've decided to go out with a bang."

He caught a taxi to the House of Fabulous, which occupied a gingerbread Victorian townhouse off Castro Street, and presented himself at the lavender door a few minutes before four o'clock. After looking around nervously to see if anyone was watching him, he pressed the buzzer, and an attractive woman opened the door almost immediately. Appearing to be in her late forties, she was conservatively dressed, wearing a knee-length black dress accentuated by a single strand of pearls. Her hair was swept back in an elaborate coif, her makeup was immaculate, and the nails on the hand she extended to Terrence were beautifully manicured.

She showed him into a small foyer which was overwhelmingly feminine in dcor. Everything seemed to be done in shades of lavender, from the chintz loveseat to the frilly lace curtains adorned with festoons and jabots. "Are you the person I spoke with on the phone?" he asked hesitantly.

"Yes, I am Madam Fabulous," she replied in a pleasant voice. "You must be Terrence." She sat down on the loveseat and patted the cushion beside her. "Sit down next to me. What brings you to the House of Fabulous?"

Terrence weighed his words carefully. After all, Madam Fabulous might wind up as a witness if the company mounted an aggressive defense. "I am a lawyer for a large corporation. Recently the California legislature enacted a law protecting cross dressing in the workplace. I have always dreamed about being a girl, and now I can do it without losing my job." She nodded sympathetically as he pulled a piece of paper out of the pocket of his shirt. "I'll have to be careful to comply with the company dress code, so as not to give them grounds to retaliate against me. Here it is."

Terrence knew the Tyrex dress code for female employees by heart, having drafted it with Helen Wallace the year before, and he watched while Madam Fabulous scanned it. "'Skirts or dresses are required except on casual Fridays. Hosiery is mandatory,'" she read out loud. "Sounds like a party, Terrence. Are you sure they're going to be happy with the new you?"

"I'm sure they won't be. That's why I need your help in making myself over."

"Very well. Repeat after me: 'I dedicate myself to the discovery of my inner woman, and I pledge my allegiance to Madam Fabulous and her Mistresses in my quest to become a Fabulous Girl'". After Terrence repeated the pledge, she stood up abruptly and ordered him to take off all of his clothing. Her voice had a new edge to it.

"Right here?" he asked, startled by her sudden change in demeanor.

"Rule number one: do not question Madam Fabulous's instructions, at any time. Would you rather take off your pants out on Castro Street?" Without further protest, he stripped down to his briefs, and when she glowered at him, he removed them also. Terrence stood, naked and exposed, as she circled around him. "Good girl, you took care of your body hair. All right, let's get started." She handed him an evil looking garment that looked like an elaborate G-string. "Stuff your family jewels up into your abdomen, tuck yourself between your legs, and put this on. At once!" she shouted when he took too long to get started.

When his package was tucked away, she nodded her approval. "Good girl," she said once again, unnerving him with the words. "That contraption is called a gaff. You are only to remove it when absolutely necessary. Now that we have that taken care of, we can give you a name. Have you any preference, or shall I assign one to you?"

His mind went blank. "How about Terry?" he asked at length.

"A lovely name. Terry it shall be." One of Madam Fabulous's assistants, a pretty girl dressed in a French maid's costume, materialized. "This is Sissy, my Mistress of Fashion," Madam Fabulous said. "Sissy, meet Terry." Sissy gave Terry a shy smile, and it occurred to him that she was almost as embarrassed as he was. Then it dawned on him. Sissy was really a guy. Although she was very pretty, her square chin and large hands were dead giveaways.

Sissy handed Terry a pair of pink lace panties and instructed him to put them on. When he did, Terry felt an uncomfortable pressure against his gaff as he began to experience a strange arousal. Sissy didn't seem to notice as she handed him a new package of pantyhose. "Have you ever worn stockings?" she asked in a husky voice.


"There's nothing to it. Here, let me show you." She led Terry back to the loveseat and sat down beside him, coaching him on how to put them on without tearing the flimsy fabric. The sensation of sheer nylon against his smooth skin was unlike anything Terry had ever experienced, and his trapped manhood continued to struggle against its unfamiliar restraints.

Sissy produced several shoe boxes, but Madam Fabulous sent her away to look for more conservative styles. "Unlike most of our clients, Terry will be dressing for the business world," Madam Fabulous explained to Sissy. The Mistress of Fashion returned a few minutes later with several pairs of black pumps. The first pair was too tight, but the second fit Terry perfectly. "Stand up and try to walk in them," Madam Fabulous said.

Terry took a few wobbly steps under Madam Fabulous's watchful gaze. The three inch heels hurt his feet. "Keep your head up and your back straight!" Madam Fabulous commanded as he minced around the foyer. "All right, that's enough for now. We'll take care of deportment after she gets dressed. Let's get her into makeup next."

Madam Fabulous led Terry into an adjoining room, where the Mistress of Style was waiting for him. As she beckoned him to sit down in her chair, Terry scrutinized her, trying to discern whether she was another man. As if reading Terry's mind, she said "We are all girls here, my dear. You have such beautiful hair. I don't think we'll need to bother with a wig. Oh good, your fingernails are long enough to file and polish. This is going to be a cinch."

Madam Fabulous left them, and for the next hour, Terry surrendered to the ministrations of the Mistress of Style. His stubble was shaved, his eyebrows were plucked, his fingernails were manicured, his hair was trimmed and set, and his face was set upon by an assortment of sponges, pads and brushes. He closed his eyes as the sweet smelling cosmetics were applied to his lips, cheeks, and eyelids, trying to imagine what he was going to look like when she was finished with him. He caught himself sliding his legs together, reveling in the sensation of nylon against nylon, the stirring in his panties becoming a steady ache.

"All right, let's get a look at you," the Mistress of Style finally said. She produced a mirror, and Terry was amazed at what he saw. The girl looking back at him was beautiful. More than that, she was undeniably feminine. Whereas Sissy's manly features had given her away, there was nothing in Terry's appearance that would suggest that he was really a guy.

"Oh my," Madam Fabulous said when she walked into the room. "She won't even need a pair of boobs to pass."

"I can't take all the credit," the Mistress of Style replied. "She's a natural."

Madam Fabulous led Terry into another room, one filled with racks of clothing and boxes of foundation garments. "The Mistress of Fashion is helping another Fabulous Girl with a wardrobe crisis, so you're getting my personal attention," Madam Fabulous explained as she used a tape to measure Terry's vital statistics. He watched as she selected a pair of realistic-looking fake breasts and stuffed them into a lacy white bra. Terry stood self-consciously as she fastened it behind him.

Madam Fabulous stepped back to admire her handiwork. "Perfect," she said. "Now, we have a decision to make. Ordinarily, I fit our Fabulous Girls with padded butts and corsets, but you are not our everyday client. Correct me if I'm wrong, but you'll be wearing conservatively cut suits and dresses, and you'll need to be reasonably comfortable in your clothes for at least eight hours day, with an occasional trip to the rest room. Am I right?"

Terry nodded dumbly as she continued. "We could give you enough curves to stop traffic, and most Fabulous Girls want just that, but I don't think that would be very practical for you. And to be honest, you've got one of the nicest bodies I've ever had to work with. You look to be a perfect size 12, maybe a 14, so we'll have no trouble finding clothes that will make you look like a career woman without putting you through contortions. Agreed?"

"Yes, Madam," he said.

"Good girl. Let's get you dressed." With that, she handed Terry an A-line dress, black with silver sequins on it, and helped him drape it around his body. "This is the most conservative thing I have on hand," she sighed, "but we're running way ahead of schedule, so there should be no problem putting a nice trousseau together for you tonight. To tell you the truth, I'm looking forward to it. There," she said after she zipped him up, "take a look at yourself, Terry." She led her customer over to a full length mirror and waited for his reaction.

He must have been in a state of shock, because she finally had to prompt him. "Well, aren't you going to say something?" In fact, Terry was at a complete loss for words. He was dressed from head to toe as a woman, and for the first time in his life, he actually liked what he saw in the mirror. As a guy, Terry had always been scrawny and plain-looking, but as a girl, he was a knockout. The pounding in his panties intensified as he turned this way and that, fascinated by the woman that he had become.

His reverie was broken by a deep voice. "Are you ready for me, Madam Fabulous?"

Terry turned to face the Mistress of Poise. No question about this one. Even in women's clothes and makeup, at six feet three inches the Mistress of Poise was too masculine-looking to be an Amazon, yet he moved with remarkable grace. Terry soon became exhausted as his drill instructor in a dress took him through basic training in moving and behaving like a lady. By the time they were finished, his feet were killing him, and his feelings of arousal were long gone.

Madam Fabulous, who watched the whole thing, had a look of approval on her face. "My Mistress of Style was right. You are a natural," she beamed.

"You say that to all the girls," Terry said with a rueful smile.

"Well, we do try to reinforce a girl's self-image, but in your case that's hardly necessary. In three hours, you've made more progress than some Fabulous Girls make in an entire weekend, and most of them never end up looking as lovely. I'm very, very proud of you, Terry." He stood awkwardly as she gave him a little hug. "Now, here's a purse you can use until we get you one of your own. I've put your wallet in it. We're going to have to hurry, but if we leave right now, we can make it to Macy's and get in an hour or so of shopping. That should be plenty of time to find you a couple of outfits to get you started. Sissy will accompany us to pick out the rest of your essentials."

At the thought of going outside, Terry suddenly experienced a panic attack. Madam Fabulous had evidently seen this look in her clients' faces before, and she tried to calm him down. "There's a word which describes the ability to go out in public and pass for a woman. It's called 'passing.' We always take Fabulous Girls out in public to give them a chance to try out their femininity, because they have to learn how to deal with getting 'read' as a man. I'll be very surprised if you get read tonight, unless you give yourself away by calling attention to yourself."

With that, they left the studio and walked a few blocks to a taxi stand, Sissy having changed out of her maid's costume into a smart pants suit. The cool night air swirled around Terry's legs as he tried to get accustomed to walking in a dress, and Madam Fabulous had to remind him to stand up straight when he hunched self-consciously while they waited for a cab. One came along in a few minutes, and Terry tried to remember what he'd learned as he slid onto the seat and tugged his dress down over his knees.

They pulled up at Macy's on Union Square at half past seven. Madam Fabulous had given Terry's measurements to Sissy, who split off from them to purchase lingerie, stockings and accessories while Madam Fabulous and Terry made a beeline for Career Essentials. In no time, Madam Fabulous selected two suits, one blue and one gray, each with a short jacket and a slim knee-length skirt. She handed them to Terry and pointed him towards the dressing room. Terry panicked when a sales associate intercepted him, stammering when she asked him if he wanted her to set up a room for him. She seemed not to notice his embarrassment, and Terry heaved a sigh of relief when she closed the door behind him.

Get a grip girl, he told himself as he tried to get out of his dress. He struggled desperately, twisting and turning until he was able to grasp the zipper and yank it down. Finally he had the dress over his head, messing up his new hairdo in the process. He paused to take a few deep breaths, looking forlornly at his reflection in the dressing room mirror. Standing there in his bra, panties, stockings and high heels, he felt overwhelmed by the predicament he'd gotten himself into. What was I thinking, he asked himself as he fumbled in his purse for a hairbrush. Being a woman was like trying to talk in a foreign language while walking on stilts.

One thing was for sure. He was way too far into this to turn back now. With a sigh of resignation, he started brushing his hair, consoling himself with thoughts of the fat settlement check he was sure to get after he finished shaking down Tyrex Industries. He removed the blue skirt from its hanger and gingerly stepped into it. After he zipped it up, he removed the matching jacket from its hanger and pulled it on. When it was buttoned, he surveyed himself in the mirror. Once again, he felt a strange stirring below the waist as he admired the smartly dressed young woman staring back at him.

"How are we doing in there," he heard Madam Fabulous ask from the next dressing room. She had evidently entered the dressing area under the pretense of trying on an outfit for herself.

"Fine," Terry said, trying out the new voice drilled into him by the Mistress of Poise. "The blue suit fits."

"Then there's no need to try on the gray one. Here, try on this dress," Madam Fabulous said as she handed it over the transom. Terry looked up and reached for a white dress with blue polka dots. After he put the skirt and jacket back on the hanger, he stepped into the dress and pulled it over his shoulders. He heard a tap on his door, and he opened it to admit Madam Fabulous, who quickly straightened out the shoulder pads and zipped him up.

"Oh my, that looks precious on you!" Madam Fabulous said. Terry turned to look at himself in the mirror, and the glow in his panties heated up as his dress swirled around his knees.

"I love it," he heard himself say in his new voice.

"Why don't you wear it home?" Before he could respond, Madam Fabulous opened the door and handed the suits to the startled attendant. "My niece wants both suits and the dress, and she'd like to keep the dress on to pick out shoes and accessories."

"Of course," the girl replied. "Let me cut off the tags for you, and ring her up at the register. I'll put her old dress in a shopping bag."

While Terry was paying with the cash from his wallet, he heard Madam Fabulous call Sissy on her cell phone. "Meet us in the shoe department in five minutes. If you get there first, we need pumps with 2" heels in black, blue and white, size 9 wide. See you there."

It was almost closing time when they met up with Sissy. She had three pairs of high heels lined up for Terry to try on, and all fit him perfectly. As he was paying for the shoes, Madam Fabulous examined Sissy's other purchases, nodding in approval. "How much in total?" she asked. Terry overheard them, and he reimbursed her without being prompted. "Almost done," Madam Fabulous said as she sprinted for the escalator. Terry's feet were on fire but he managed to keep up with them.

He caught up with Madam Fabulous in the handbag department. He was about to tell her that he probably would only need one day's worth of clothing when he caught himself, and he grimaced as he handed over another fistful of bills to pay for three new purses. At least Madam Fabulous found them on sale.

"Only one more thing," Madam Fabulous said as they struggled with their shopping bags. She led Terry to the fashion jewelry department and found a salesgirl who was just closing up for the night. "Is it too late for my niece to get her ears pierced?"

The girl looked over the counter, expecting to find a ten year old, and she was startled when she came face to face with a bewildered Terry. "About ten seconds," she said, and before Terry could protest, he was cringing in a chair as the needle went into his ears.

"That was on me," Madam Fabulous said as they headed for the door.

By the time he got back to his apartment, laden down with shopping bags, Terry was utterly exhausted. Madam Fabulous had made him promise to hang up his new outfits so they wouldn't wrinkle, and she barked a few final instructions to him before their taxi dropped him off. "There's enough makeup in this bag to last you for at least a month," she said, handing him a cosmetics kit. "Sissy got you all the lingerie, jewelry and accessories you'll need for your first few days. Next time you go shopping, you'll be on your own, but if you have any questions, promise that you'll call me, any time. You have my number," she said, tucking a lavender business card into his purse.

He was almost too shell-shocked to speak when the cab pulled up to his apartment building. "Thank you for everything," he managed to say.

"It's been a marvelous evening. And remember, you are a Fabulous Girl now!"

* * *

Terrence Poindexter used to get up at five o'clock every morning to jog ten kilometers before breakfast. That was how he managed to maintain the slim physique so admired by Madam Fabulous.

But when Terry awoke at his usual time, it took him several seconds to realize that things were going to be different this morning. For starters, he was wearing a blue satin nightgown and panties, which he found in one of the shopping bags given to him by Sissy the night before. At first he wasn't going to bother with them, but for some reason he put them on before he went to bed.

So when he woke up, he found himself with a raging hard-on. Why is this turning me on, he asked himself as he looked down at his new body, so sleek and smooth in its silky lingerie. If I were a guy, I'd want to fuck this body, he said to himself. Wait a minute. I am a guy, aren't I?

One thing was for sure. There was no way Terry would be able to get his gaff back on if he remained in this condition. He tugged his panties down, and his erect penis sprang to attention. He grasped it in his manicured fingers, and after a few swift strokes, a rope of semen shot clear over his head, narrowly missing his new hairdo.

It was the most pleasurable orgasm of Terry's life. In fact, most of his sexual experiences had been self-administered, his successes with women sadly lacking over his twenty-eight years. As he lay there now, reveling in ecstasy, he was torn by feelings of lust and loathing. Although he loved the way he looked and felt, he was ashamed of himself for feeling that way.

Finally his gratification subsided, and Terry got out of bed. Think like a lawyer, he told himself, mentally organizing the tasks at hand. Remember your training, and think of the payoff. You know what you have to do. A glance at the clock told him it was time to get moving.

Terry brushed his teeth and gave himself a close shave while drawing a hot bath. After pinning up his hair, he lowered himself carefully into the tub and luxuriated for a few minutes in the hot suds, which he'd salted with bubble beads found in the cosmetics kit from the House of Fabulous. Then he picked up a new bic razor and carefully went over his arms and legs, removing the traces of stubble which had begun to grow back. With his manhood submerged below the bubbles, Terry could have been a girl as he shaved his legs.

After he finished scrubbing himself off with a loofa, he patted down his tender skin and applied a soothing coat of moisturizing crme to his arms and legs. Women know how to pamper themselves, he thought idly as he stood before his mirror and began applying his makeup. It almost makes up for the hassles they have to deal with, like trying to put on eyeliner. He took his time, remembering his lessons from the Mistress of Style, and after a few false starts and some trial and error, his face looked almost as good as it did the night before. He finished with a spritz of cologne behind each ear, finding his scent strangely intoxicating.

He felt his penis stirring, so once again he took decisive action, stroking himself while he gazed at his pretty face in the bathroom mirror. He reached up with his other hand and loosened his hair, which fell sexily down around his neck as he pulled and jerked on himself. Once again, he came in a rush, spewing jism onto the vanity as his knees buckled from the pleasure of his release, although it was tinged with feelings of shame.

With his penis limp at last, he tucked himself up into the gaff and headed back into the bedroom. "What to wear today?" he said out loud in his new voice, knowing that he needed all the practice he could get. "I'll think I'll wear my gray suit with black stockings." He opened up one of his drawers, and found the pile of lingerie which he'd stuffed there. Selecting a black bra and panties, he strapped on the bra, inserted his breast forms into the cups, and watched them jiggle as he shimmied into his panties. Then he opened a new pair of sheer black pantyhose and sat down on the edge of his bed to put them on. As he eased the delicate nylon up his legs, he thought he could feel the beginnings of another erection being stifled by his gaff. Terry was aware of a dull ache in his groin when he did a deep knee bend to pull his stockings up to his waist.

He lingered for a moment in front of his closet, relishing the caress of nylon against his freshly shaved legs. He wondered if it felt this good for real girls? After a moment's indecision, he took a thin black sweater off its hanger and tugged it over his head. Then he stepped into his gray skirt and zipped it up behind his back. It was fully lined, Madam Fabulous told him, so a slip would not be required. He lifted it up and smoothed his sweater before lowering it again, watching in fascination as his skirt settled a few inches above his knees. Then he remembered the fashion jewelry that Sissy had picked out for him, and he took a few moments selecting a simple gold necklace and a matching bracelet that looked good with the gold studs on his ears. After he buttoned up his jacket, he rummaged around the closet floor for his new black pumps. They were a bit tight, but his stockinged feet slid right into them, and he spent a few minutes practicing the deportment lessons that the Mistress of Poise had drilled into him.

Terry remembered his new women's wristwatch, and he was alarmed to see that it was after seven o'clock when he put it on. Let's see, what else is there? My purse! He took his black one into the bathroom to fill it up, and realized that he hadn't done anything with his hair. He found his brush and began working on his new shag hairdo, which the Mistress of Style assured him would be a snap to take care of. After a few minutes he had it as good as it was going to get, so he dropped the brush into his new purse, along with a compact and lipstick, and tried to think what else he should put in there. Soon it was bulging with keys, his new women's wallet, tissues, breath mints, a small mirror, cell phone, sunglasses, emery board, and miscellaneous junk. Anything else? He must have forgotten something!

Terry realized that he was prolonging the inevitable. His heart was racing when he slung his purse over his shoulder and headed for the door.

* * *

The receptionist at Tyrex Industries did not come on duty until eight o'clock. A key part of Terry's plan was to arrive before she got there and let himself in with his coded entry pass. Then he could wait behind closed doors in his new private office until his confrontation with Mr. Bigelow.

For that reason, and to spare himself the anxiety of trying to pass on the crowded Muni, he decided to take a taxi to work. He was dismayed to find a man waiting in line ahead of him at the taxi stand. He was about thirty, immaculately dressed in an expensive suit, crisp white shirt and subdued tie, and he smiled as Terry approached. "Morning. Beautiful day," the man said. He was very good-looking, and he had a gleam in his eye as he admired Terry's long legs.

"It sure is," Terry replied with a shy smile.

A cab pulled up to the curb. "Would you like to share it?" he asked.

Terry froze. He needed to get downtown, and there might not be another cab for a long time.

"My office is on Sansome Street," the man added.

Tyrex was on Montgomery Street, a block away. "Sure, that would be nice," Terry said. The man opened the back door of the cab, and it took Terry a moment to realize that he was waiting for him to get in. He climbed awkwardly into the back seat, his skirt riding all the way up to his ass, and tugged it down furiously as he slid across the seat.

His companion sat down next to him and held out his hand. "My name's John Stone."

"I'm Terry," he said, offering a limp wrist.

"What great weather for January," John said. "How long have you lived in the City?"

"Six years," Terry replied. No point in lying to every question.

"Almost as long as me. What do you do, Terry?"

"I'm a paralegal." Best to stay within striking distance of the truth.

"How about that? I'm a lawyer for Earp and Crosby." Terry knew the firm well, in fact they did some work for Tyrex. "Who do you work for?" John asked.

Terry thought fast. "Actually, I'm looking for a job. I have an interview this morning with Tyrex Industries."

"Hey, I know some of the people in the legal department there. Or at least I did. The guys I knew left or got canned, not sure which. So you know they have openings."

"Sounds like a rough place," Terry said, curious to know how the world viewed Tyrex.

"I don't want to discourage you, Terry, but you should look around a bit. Maybe talk to our firm. I'm sure we'd be interested in you."


"On second thought, that might not be such a good idea."

"Why not?"

"We have a firm policy against lawyers dating staff. That would be a real bummer."

Terry felt himself blushing. "I guess I'll have to decide between love or money."

"A girl like you can have it all." Terry was trying to figure out how to respond when the cab pulled up beside his building. He started to reach into his purse for his wallet when he felt John's hand on his knee. "It's on me, Terry. Here's my card. I'd love to see you sometime."

Terry put the card in his purse and opened the door. "Thanks, John. Maybe I'll call you, okay?"

"Any time," he said through the open window as the cab pulled away.

His confidence soaring, Terry smoothed down his skirt, slung his purse back over his shoulder, and walked through the revolving door to his office building. The crowd in the lobby brought him back down to earth. He waited nervously for an elevator, wondering if anybody would recognize him. But only a few people got onto the elevator with him, and he was alone by the time he arrived at Tyrex's floor. A quick glance at his watch told him that it was ten minutes to eight. He had his entry card in his hand, and after he let himself in he turned down the carpeted hall towards the general counsel's office. As he hoped, nobody saw him before he entered the large corner office and closed the door behind him.

Terry surveyed his new surroundings, pleasantly surprised. The office was as he remembered it from frequent visits, beautifully furnished with a large oak desk, a throne-like chair behind it, a matching credenza and bookcase, and a furniture grouping consisting of a sofa, two chairs and a coffee table. What surprised him were the diplomas on the wall and the knick knacks on the desk, taken from his old office and tastefully arrayed. His laptop computer was hooked into a docking station on the clean desk, and his personal diary lay open on the credenza.

I could get used to this, he said to himself as he sat down in the soft leather chair behind the desk. A glance down at his skirt and stockings brought him back to reality. Did a guy really hit on him a few minutes ago? If he could pass that kind of inspection, he could fool anybody.

He was looking at John Stone's business card when he heard a knock on the door. "Mr. Poindexter? May I come in?" It was Gail Chestnut.

Why not? She was going to find out anyway. "Yes," he said in his old voice. After she opened the door and came inside, he said, in his new voice, "Please close the door."

He watched with interest as Gail Chestnut displayed a kaleidoscope of reactions. Confusion, recognition, and shock all registered on her beautiful face as she stood rooted to the carpet. Finally Terry got up from his desk and walked over to the door, closing it while Gail continued to stare at him, open-mouthed. "Sit down, Gail, and I'll explain," he said, pointing to the sofa. Gail followed him and watched as he sat down in one of the facing chairs, carefully crossing his legs after smoothing his skirt beneath him. She collapsed onto the sofa, finally composing herself enough to speak.

"Mr. Poindexter, is that really you?"

"Yes, and please call me Terry," he replied.

"Why are you dressed like that?"

"It's a long story. Why don't you get us each a cup of coffee and I'll tell you all about it." Gail got up to leave, and when she got to the door, he said, "Gail, please close the door behind you, and promise that you won't tell anybody about me. Not until I have a chance to put out an announcement. Okay?"

"Sure," she said, still dazed. Gail returned a few minutes later with a tray of coffee, cups and utensils, and he waited until she sat back down and poured them each a cup before he spoke again.

"I appreciate everything you did yesterday to make my office so homey," he began.

"Don't mention it, uh, Terry. I'm sorry about the name plate on the door."

"I didn't even notice it."

"It says Mr. Poindexter."

Terry laughed, a girlish giggle that seemed to put Gail at ease. "I doubt if I'm going to be around long enough for them to make up a new one."

"Then why are you doing this? I mean, so you have a secret life. Why put your job at risk?"

"Some day I'll explain it to you, Gail. Right now, I just have to make it through my nine o'clock meeting with Mr. Bigelow. Do you have any idea what it's about?"

"The scuttlebutt isn't good. What did you say to him yesterday?"

"I just gave him some legal advice."

"Well, evidently it didn't agree with him. The rumor is that you're going to be let go today."

Terry wanted to take her into his confidence, but he didn't know if he could trust her. "I was afraid of that. Maybe I can talk him out of it."

"In that getup? You've got to be kidding. He'll fire you on the spot when he sees you like this. Are you sure you can't tell me why you came to work this way?"

"It's a long story."

"We have time. It's only eight o'clock," she said as she poured him another cup of coffee. "How long have you known you were gay?"

"I'm not gay," he said defensively.

"Sh'yea, right."

"I mean it! I don't like guys."

"So what are you, a transsexual? Are you going to have an operation?"

"No!" He realized that her questions were logical and natural, and she seemed startled by his reaction. "I don't want to have sex change surgery," Terry added before draining another cup of coffee. As he did so, he felt a twinge in his bladder.

"Then what do you want?"

"Millions of dollars from Tyrex Industries to go away quietly," he would have liked to tell her. Of course, he could never admit that to anyone. So instead, he said, "I just want to look, and live, like a woman. Consider it a complement, Gail. I've always thought girls got all the breaks."

"Dream on," she said. "You wanna trade places sometime, Mister, you can have my life. Get real."

He was genuinely puzzled by her response. After all, Gail Chestnut was one of the most beautiful women he had ever met, and she seemed to have so much going for her. They found themselves becoming fascinated with each other as they sat there, chatting away like two girls. He found her incredibly attractive, and this time she was the reason for the uncomfortable stirring in his panties, spiced by his confinement to silk and lace. "Aren't you happy?" he asked.

"Give me a break. Half the guys in San Francisco are gay, and the rest think they're God's gift to women. I've been hit on so many times, I can't even look at a guy any more without putting my left up." Terry remembered how he himself had already been propositioned during his one excursion as a woman, but it hadn't bothered him particularly, and he was a guy. Something else was happening here.

"Don't you like guys?" Terry asked.

"Hey, how did this go from being about you to being about me? You're the one who has some explaining to do."

He topped off her coffee and poured himself another cup. When he sat back and crossed his legs again, she said, "How did you get so good at this?"

"Good at what?"

"Talking the talk, and walking the walk. I swear to God, if I didn't know who you were, there's no way I'd believe you were a guy."

How to explain it to her, let alone himself? What had the Mistress of Style called him? "A natural", she said. All Terry started out to do was put on a dress and get himself fired, but the more he was getting into it, the more he was getting into it.

Once again Terry tried to change the subject. "You didn't answer my question."

"What question?"

"Do you like guys?"

For some reason, she felt like opening up to him, maybe because he seemed so unthreatening, sitting next to her in a skirt and high heels. "I don't know, Terry. I mean, I've loved guys in the past, but it's been a long time. Most of them I think are gross."

"Do you like girls?"

"No! I mean, not in that way. Dammit, here we go again, talking about my problems. You're the one who's about to get canned. How you gonna keep yourself in pantyhose then?"

He was about to answer when his telephone rang. He picked up the extension on the coffee table. "Hello," he said, remembering at the last second to use his old voice while Gail looked on in amusement.

"Hello Terrence, it's Helen. Mr. Bigelow asked me to sit in on his nine o'clock meeting with you."

Terrence Poindexter and Helen Wallace went back a long way, and he knew she would be honest with him. "Give it to me straight, Helen."

"Do you mind if I stop by?"

"I'm in the middle of something right now. Can't you tell me anything?"

"It doesn't look good, Terrence, that's all I can say. I'll do my best for you."

"I know you will, Helen. Chin up. It won't be a dull morning."

Gail was laughing as he hung up the phone. "I'll say this for you, Terry. Although you'd never know it, you've got balls. I mean, I always thought you were kind of a wimp, sitting back there in your little office, watching the alpha dogs fight it out. Aren't I pathetic?"


"Now that you look like a woman, all of I sudden I find you attractive. What does that say about me?"

Terry was speechless. How could she possible see anything in him now? He was trying to think of a response when the calendar program on his computer beeped at him. It was the ten minute warning for his meeting with Mr. Bigelow! Where had the time gone? When he got up from his chair, he realized that three cups of coffee had been a big mistake. He had to go to the bathroom. Bad.

"Gail, I need to ask you one more favor."


"I have to go to the ladies room. Can you check and make sure the coast is clear?"

"Sure, but I don't think you need to worry. Nobody is going to recognize you."


"Terry, when I first walked into this office, I thought you were a complete stranger. Come one, let's go. Nobody is going to know who you are. If anyone asks, I'll tell them you're a new hire."

Terry picked his purse up off the desk and together they walked down the hall to the restroom. Without hesitation, he followed her in, relieved to find that there was nobody inside. He went into a stall and closed the door.

"Don't forget to sit down," Gail whispered.

"Be quiet!" he hissed. She was laughing as she left him alone. He lifted up his skirt, pulled down his panties and hose, and gently eased his gaff away from his aching privates. He was alarmed to find himself semi-erect, and he had to wait impatiently until his body was able to relieve itself. When he was finally done, he tucked himself back between his legs, pulled his panties and pantyhose back up, and tugged his skirt back down to his knees. He was about to leave the stall when he heard someone coming in the door.

Damn it! Should he wait here until she was gone, or take his chances? He glanced at his watch. Three minutes to nine! Before he could stop himself, he opened the door and walked over to the full length mirror. One of the secretaries was just going into another stall.

Terry noticed that his sweater had gotten tangled and his lipstick looked washed out. As if he had been doing it all his life, he lifted up his skirt and smoothed down his sweater before dropping his skirt back into place. After washing his hands, he took his lipstick out of his purse and applied just a touch to his lower lip before puckering up the way the Mistress of Poise taught him. He brushed away a few stray hairs, and he was on his way out before the secretary left her stall.

Gail was waiting for him outside his office. "You better run, it's time for your meeting," she said.

"Wish me luck," he said as he hurried down the hall.

* * *

Charles Bigelow had asked Helen Wallace to join him a few minutes before nine, and she sat quietly in one of the two chairs provided for supplicants before his massive desk. She had mixed feelings as Bigelow read through the resignation letter she prepared for Terrence Poindexter's signature. Terrence was one of her few remaining friends in the legal department, and they had worked well together. She was sorry to see him go, but business was business, and she hadn't become a corporate survivor by being soft.

Bigelow grunted when he finished reading the letter. "Three months severance. Do we have to give him that?"

"Yes sir, it's company policy and Terrence will be well aware of that."

"Do you think he'll sign this?"

"I think so. I wasn't able to talk to him this morning to feel him out, but I suspect he knows this is coming, and I don't think he'll put up much of a fight."

A grim smile came over Bigelow's face. "Since this is set up as a resignation, he isn't entitled to any severance at all, is he?"

Sometimes Helen hated her job. "Sir, technically that's correct, but we really are forcing him out, and he'll be much more likely to go quietly if we give it to him. If he balks, we can always take it off the table. He'll be much more likely to sign if he has some incentive to do so."

"All right, let's get this over with. Where is he, anyway?"

Bigelow's executive assistant stuck her head in the office. There was a strange look on her face. "Mr. Bigelow, uh, Mr. Poindexter is here."

"Well, send him in," he said impatiently. She stepped aside and watched Terry waltz into the office. Both Helen Wallace and Charles Bigelow were frozen in shock as Terry pulled back the empty chair and seated himself, curling one of his legs around the other. His skirt rode several inches up his thigh, and he let it ride while he waited for one of them to speak.

Helen's instinct for self-preservation saved her from blurting out her initial reaction. Overweight and unattractive, all she could say to herself was: "I'm a woman, and he's better-looking than I am. It's so unfair!"

Charles Bigelow had no such inhibitions. "What the hell is this?"

"A Halston. They're on sale at Macy's, although I doubt if they come in your size."

Bigelow's face bulged over the collar of his white shirt. "I knew you were a homo from day one!"

"A common misconception. Not that there's anything wrong with that."

"I want you out of here!"

"Then why did you ask me to come to your office?"

"You're f...."

Helen found her voice before it was too late. "We think the time has come for us to separate," she cut in, trying to get the meeting back on script despite the incredibly bizarre circumstances. She slid the resignation letter across the desk to Terry, who studied it while Bigelow looked on in fury, his face turning bright crimson.

"This is a resignation letter," Terry said at length. He looked up at Mr. Bigelow. "Why would I want to resign? I like it here."

Bigelow finally erupted. "You're fired, fagolito!"

"On what grounds?"

"Give me a fucking break! You show up in my office in a fucking dress and you ask me why you're fired? Get out!" he shouted. Helen looked on helplessly, sensing impending disaster.

"Thank you for clearing that up, Mr. Bigelow. I'm sorry you don't like my outfit, but it conforms to the Tyrex dress code, and under AB 196, I have a legal right to wear it. Why, we discussed that just yesterday."

Helen tried desperately to control the damage while Bigelow went from red to purple. "Terrence, those really wouldn't be the grounds for your separation from the company...."

Terry cut her off. "Come off it, Helen. You heard what I just heard. And if you're called as a witness, you'll have to tell the truth. Any jury in San Francisco would find Tyrex Industries in willful violation of my civil rights."

Charles Bigelow looked like he was about to have a seizure. At that moment, there was a rap on the door and Doyle Rogers, the Executive Vice President and Chief Financial Officer, stuck his head in the office. "I'm sorry to interrupt, Mr. Bigelow, but it's urgent." He glanced at Terry and did a double-take before continuing. "We just received a letter from Great White, LLC. They've launched a tender offer." He stared at Terry as he reached across the desk and handed a letter to Bigelow.

Bigelow read the letter with shaking hands. "My God, it's a hostile takeover!" he gasped. Suddenly his face became contorted, and he clutched at his chest. The morning's twin shocks were too much for Charles Bigelow. Thirty years of red meat, cigars and martinis had finally taken their toll.

Helen looked on in horror as Bigelow's face went from purple to gray, like some kind of grotesque chameleon. "Call 911" she cried. "He's in cardiac arrest!"

* * *

Terry walked back to his office in a trance. While they were waiting for the ambulance to take Bigelow away, Doyle Rogers had taken him aside. "What's going on?" he'd asked.

"I just got fired."

"No you didn't. It looks like I'm in charge now, and I'm going to need you to help fight this takeover." He looked on disbelief as Doyle tore up his resignation letter.

Terry tried to protest, but what could he say? That the whole thing was a scam? Word of his transformation spread throughout the office like wildfire, and he felt like a carnival attraction as he passed the desks of gaping secretaries on the way down the hall.

Gail was waiting for him, and she closed the door behind them after he sank into his leather chair. "What happened?" she asked.

Terry shook his head. "I'm screwed."

"Terry, I'm so sorry. I'll help you pack up your things."

"That's not what I mean, Gail."


Terry unloaded on her. "The whole thing was a con, Gail. I knew Bigelow was out to get me, so I came up with the idea of dressing like a woman so I could nail the company for discrimination. I didn't figure on Bigelow having a heart attack."

"A heart attack?"

"He's on his way to the hospital. Now I'm stuck like this."

She moved over to his chair and looked down at him. "Let me get this straight. You're really not a cross dresser?"

"I never even tried it before yesterday."

She sat down on his lap. "My God, you have balls. Putting on a skirt to stick it to the man. What a turn on." Before he could say anything, she leaned over and kissed him, gently at first, then with animal passion. Terry responded immediately, and he nearly bent over double over as his penis strained against the gaff.

"What's wrong?" she asked.

"I'm all tucked in down there," he said, grimacing in agony.

"This I've got to see," she said, sliding off his lap. While he looked on in disbelief, she reached up his skirt and pulled down his hose and panties. Then she found the strings on his gaff, and he moaned as she released him. When her head went up his skirt, he rolled back in his chair in ecstasy as she took him into her mouth. He came almost instantly, losing himself to waves of exquisite pleasure. When it was over, he sat back, utterly spent, while she ran her fingernails over his stockings.

At first he didn't hear the tapping on his door. When he did, he sat up with a start just before Doyle Rogers stuck his head in the office. "Terrence, do you mind if I come in?"

Terry pulled up his chair and tried to act nonchalant while Gail huddled beneath his desk. Fortunately, he remembered the Mistress of Poise admonishing him that 'a lady remains seated when a man enters the room.' "Hello, Doyle," he said in a strangled voice.

Doyle Rogers eyed him with curiosity. A fastidious man in his late thirties, he maintained a respectful distance while he weighed his words. "I must say, Terrence, I was surprised to see you this way. But I want you to know that I respect you for having the courage of your convictions."

"Why thank you, Doyle. And please call me Terry."

A toothy smile filled Doyle's handsome face. "We're going to be working very closely together on this takeover battle, Terry. I think it would be a good idea if we got to know each other better. That's why I was hoping you could join me for dinner tonight."

Terry started to hem and haw until he felt Gail pinch him on his thigh. "That would be lovely," he said with a shy smile.

"Wonderful. I'll meet you at the Carnelian Room at eight o'clock." Doyle turned and left before Terry could say anything else.

Gail got up from under his desk and helped him pull himself together. "Thanks," was all he could say.

"Don't mention it. That was a blast."

"It was amazing. You're amazing."

"Just looking out for my department head," she said as she straightened out his skirt. "It looks like the girls are right about Mr. Rogers."

"What do you mean?"

"His secretary thinks he's a closet queen. Maybe he wants to follow in your footsteps."

"That's all I need."

"I couldn't believe it when you almost blew him off for dinner. Stick with me, Ms. Poindexter, and you'll learn the secrets to executive success. I already gave you lesson number one."

"What's that?"

"How to suck up to the boss." She kissed him on the lips and headed back to her desk.

After she was gone, Terry sat back in his plush chair and crossed his silky legs. I could get used to this, he said to himself. Having a great office, getting close to Gail, even wearing women's clothing every day....

He rummaged through his purse for a lavender business card. After a moment's hesitation, he dialed the number. A familiar voice answered the phone on the second ring. "House of Fabulous."

"Hello, Madam. It's Terry."

"Terry, how nice to hear from you. How was your first day?"

"Fine, but I need your help."

"What is it, dear?"

"I'm going out to dinner tonight, and I haven't a thing to wear."

By the author of Skylord, coming soon from PublishAmerica
TG crossdress rated-M
This article comes from BigCloset Classic

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