The House of Fabulous

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"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."

"You have a dinner date already? It's only your first day as a woman! I'm beginning to believe my own advertisements," Madam Fabulous said into the speakerphone while she sifted through some paperwork on her Queen Anne desk.

"It's with one of our senior executives," Terry Poindexter explained. "We'll be discussing business, but he's taking me to the Carnelian Room."

"How elegant! That white and blue dress I picked out for you last night would be perfect."

"Are you sure it's fancy enough?"

"Of course. It looks lovely on you. You can dress it up with the matching pashmina Sissy got you."

"Do you mean the blue shawl?"

"Um hmm. You have nothing to worry about, my dear. It's winter, so go with the blue shoes and purse. Have a wonderful time, and please call me tomorrow and tell me all about it."

Terry hung up the phone and swiveled his plush leather chair around to glance at the diary on his credenza. He had no engagements that evening, as usual. With a girlish hand, he wrote "Dinner with Doyle" at the bottom of the page, and then he turned to his computer and began sifting through the day's email messages. He tried to take his mind off the fact that he was dressed as a woman, but every time he saw his polished fingers flying over the keyboard, his predicament was brought home. With a sigh of resignation, he kicked off his heels, tucked his stockinged feet under his skirt, and turned his attention to the legal problems of Tyrex Industries.

He spent most of the afternoon researching the ins and outs of hostile takeovers, and did some online digging into Great White, LLC, the company which had launched a tender offer that morning. What he saw wasn't good: fueled by buckets of cash from a New York investment bank, Great White was on a buying binge for undervalued companies, and they looked unstoppable. It was hard for Terry not to think about his personal situation as he scrolled through the SEC filings on his screen. Once Great White acquired a controlling interest in Tyrex Industries, they would be perfectly within their rights to replace all of the company's officers, and of course he would be the first to go when they discovered that he wore women's clothing to work. Unless he could find a way to stop this takeover, his career and his reputation were on the road to ruin.

He thought about returning to work the next day in his male persona, and abandoning his scheme to get Tyrex Industries to pay him off. But after a quick glance at the canons of legal ethics, he abandoned that idea as even more risky. As a company lawyer, he had fiduciary obligations to his employer, and if it were revealed that he tried to goad them into giving him a severance package under false pretenses, his license to practice law would be in jeopardy.

Utterly absorbed by his legal and personal misfortunes, Terry lost complete track of time, and he sat up with a start when Gail Chestnut, his gorgeous executive assistant, came into the office. "It's almost five o'clock," she said. "Is there anything else I can do for you before I leave?"

He debated about asking her for another blow job, but thought the better of it. "Not that I can think of," he said.

"Did you see the announcement about Mr. Bigelow?"

"No, I was too caught up with Lexis/Nexis."

"He's in intensive care at Saint Francis, but it looks like he's going to pull through. Doyle Rogers has been named interim CEO."

"That's nice."

"Well, have fun with Doyle tonight," she said with a wink. "I can't wait to hear all about it tomorrow. Or even better, call me when you get home, if you feel like a little girl talk." She spun on her heel and left before he could think of a response.

* * *

Terry left the office a few minutes later. He ignored the gapes and stares of employees who had heard about his transformation but had to see him to believe it. It wasn't until he stepped out onto Montgomery Street that it occurred to him that he was wearing a disguise. The people at Tyrex Industries might have regarded him as an oddity, but the strangers on the street regarded him as a woman. To his relief, there were no strange looks or double-takes, only an occasional leer from a man sizing him up as a potential score. He rode the Muni back to his neighborhood without incident, and it was almost six o'clock when he let himself into his apartment.

Two hours to get ready for his first date! Well, not really his first date – he'd had his share of one night stands and disastrous blind dates as a man, but never a serious relationship. Maybe his luck as a woman would be better, he thought ruefully as he peeled off his lingerie and stockings and drew a hot bath. After the stresses of the day, and the spectacular sex with Gail under his desk, the raging erections which had plagued him since his transformation the previous day were strangely absent, he noticed as he sank with relief into the hot suds. Even though it meant he would have to dry and style his hair, he dunked his head and held his breath for as long as he could, as if that might suspend time and forestall his date with another man.

Eventually, he dried himself off, wrapped a towel around his wet head like a turban, and dusted his body with fragrant powder from the House of Fabulous. Once again, he pampered himself with moisturizing crème before applying his makeup, which went on quicker and easier this time. A learned trait, he mused while running a blow dryer over his hair. Would styling his new shag hairdo come to him as easily? It did, although it took longer than he anticipated getting it just so. It was well past seven when he gaffed himself and returned to his closet to get dressed for the evening.

Let's see, what lingerie and stockings went with his dress and shoes? Terry selected a white bra and panties and the full white slip that Sissy told him to wear under his new dress. He opened a package of sheer nude pantyhose, savoring their caress as he smoothed them on. His exhausted penis came momentarily to life despite its restraints, and Terry tried to ignore it, carefully lowering his dress over his head and pulling it up to his shoulders. As he reached back to zip it up, the lacy hem of his slip peeked out from under his dress, and another spark of arousal was stifled by the unforgiving gaff. Terry's cheeks were blushing through his makeup as he stepped into his navy blue pumps and surveyed himself in the mirror. Holy shit, he said to himself. I'm a knockout.

A dazed Terry took his pashmina out of his dresser and experimented with how to wrap it around his back and shoulders. Somehow it added grace and femininity to his already stunning reflection, and by the time he finished himself off with some jewelry and cologne, Terry was actually shaking. Not with fear and dread over the prospect of going out on a date with a man, but with shock and awe over the enormity of his transformation.

It was almost eight o'clock by the time he picked up his blue purse and headed for the door.

* * *

Doyle Rogers sat anxiously at a table for two overlooking the lights of the Golden Gate Bridge. What was I thinking, he asked himself for the hundredth time, suggesting that Terry Poindexter meet me for dinner? Here of all places, at a restaurant widely acknowledged as the most romantic in San Francisco. The little table was covered with crystal and flowers, and Doyle fidgeted nervously with his thick linen napkin, wondering if it was too late for him to call Terry and make up some excuse.

Who was he trying to kid? The moment Doyle saw Terry Poindexter dressed as a woman in Charles Bigelow's office, he felt a rush of envy and excitement. For years, he had kept his secret hidden during his relentless climb up the corporate ladder. Now that he was on the brink of success, his long-repressed urges threatened to boil over.

Doyle Rogers had yearned to be a girl from the moment he became aware that there were two sexes. His earliest childhood memory was when he was three years old and his older sisters dressed him up as a princess for Halloween. During his adolescence, he dreamed of sneaking into their bedroom and trying on their clothes, but the risk of exposure was too great a deterrent. He threw his energies instead into amateur theater, winning roles in student productions and community playhouses that enabled him at least to wear makeup and don the occasional female costume. Strikingly handsome, he had become sought-after as a leading man in regional theatrical circles, but when it came time for college his uptight parents steered him away from Broadway or Hollywood and into a career in business and finance. There he had labored, mechanically climbing rung after rung while his secret lay deep beneath the surface.

Until this morning, when he saw Terry Poindexter dressed as a woman. If a dweeb like Terry had the courage to come out of the closet, why couldn't he? For Doyle, the prospect of transforming himself into a woman was not sexually arousing. Unlike Terry, he was a true transsexual, although he had married and divorced twice in vain attempts to achieve respectability. Now that the brass ring at Tyrex Industries was within his grasp, Doyle Rogers instinctively started reaching for his ultimate objective, even if achieving it would mean his downfall.

His thoughts were interrupted by the sight of a striking woman in a blue and white dress coming towards his table. Doyle could only stare as the maitre'd pulled back the opposing chair and Terry sat down gracefully, taking off his shawl and spreading it across the back of his chair before he turned to face Doyle. "Sorry I'm late," he said. "It takes so much longer getting ready these days."

"You look...marvelous," Doyle stammered.

"Thanks," Terry said with the casual assurance of a woman who is used to being told that she is beautiful. "I still have a hard time believing it's really me when I look in the mirror."

A waiter interrupted them with menus and a wine list. After Doyle ordered a very expensive bottle of chardonnay, he began to pepper Terry with questions. "How long have you known that you wanted to become a woman?"

Terry weighed his words carefully. "It's hard to say." The less said about himself, the better. Doyle was his boss now, and if he even suspected that Terry's masquerade was a scam, he would be out on his ear.

"Have you been dressing up like this for a long time?"

Better be careful here. Once caught in a lie, everything could unravel. "Not really."

"I find that hard to believe."

How to turn the conversation to business? Terry saw his opportunity when the waiter returned with their wine. After Doyle went through the tasting ritual, Terry raised his glass and offered a toast. "To the new CEO of Tyrex Industries. Congratulations, Doyle."

When they sipped their glasses, the wine ricocheted off Terry's empty stomach and went straight to his head. Feeling slightly woozy, he grabbed a breadstick and began to nibble on it, trying to act ladylike while maintaining control of the conversation. "We're in a tough spot, Doyle. I did some research on Great White today."

Reluctantly, Doyle shifted gears. After all, he was supposed to be having dinner with his general counsel, at company expense, not indulging in secret fantasies. "Tell me what you learned."

"For starters, we can't just blow them off. The letter from Great White is what is known as a 'bear hug'. Because our stock is so low, thanks to the bumbling of Charles Bigelow, Great White's offer is reasonably attractive to our shareholders, and the board will have to give it serious consideration."

"The board has agreed to meet with representatives of Great White in two days to formally consider the offer."

"Do you know who's coming?"

"Yes. Their Chairman, Darwin DeVour, and the head of a New York investment bank."

"Probably Lance Raptor of Carnivore Capital."

"That's right." The waiter returned to take their orders. Although he hadn't had a square meal in almost two days, Terry resisted the temptation to order the biggest steak on the menu, reluctantly selecting a pasta dish. Doyle ordered sea bass, then asked him, "How did you know about Carnivore?"

"I pulled up the history of Great White's recent acquisitions on Lexis this afternoon. DeVour has been cutting a swath through corporate America funded by Carnivore. They're probably in San Francisco tonight plotting our demise."

"Right again. When the board asked me to confirm the meeting, I called DeVour's secretary in New York, and she gave me the number of his suite at the Mark Hopkins. When I called, Raptor answered the phone."

"They're the world's last authentic playboys."

"I beg your pardon?"

"According to an article I read on Lexis, DeVour and Raptor have a history of carousing together the night before they go in for the kill. No woman in San Francisco will be safe tomorrow night." As he said it, the germ of an idea began to grow in Terry's mind. It was crazy, but no more so than his current situation. Maybe the wine was starting to go to his head.

"Too bad we can't get close to them," Doyle said. "If we could find out what their strategy was, we might be able to outmaneuver them in front of the board."

You just read my mind, Terry said to himself. He surveyed Doyle's handsome face as he took another sip of wine. With his sculptured features, high cheekbones and fair skin, he might make a better-looking woman than Terry. Give Madam Fabulous a few hours with him, and....

The waiter presented their salads. Terry took a few dainty bites before he floated the thought across the table. "There might be a way, Doyle, but it would be highly unorthodox."

"We have nothing to lose at this point. Unless we do something dramatic, we're going to be hitting the bricks by the end of the week. I don't think that will be much fun in high heels. Come on, counselor," Doyle smiled. "If you have an idea in that pretty little head of yours, let's hear it."

"You spent some time in the theatre, didn't you?" Terry asked, already knowing the answer from Doyle's company bio.

"My first love," Doyle said. "Underneath this button-down façade beats the heart of a frustrated thespian."

"Have you ever played a woman's part?"

The question was so unexpected that Doyle laughed out loud, drawing stares from the nearby tables. "What makes you ask that?" he countered with forced nonchalance.

"Because my idea would entail an undercover operation on our part. Tell me, Doyle, have you ever heard of the House of Fabulous?"

Doyle could barely conceal his excitement. How many times had he seen those advertisements and dreamed! From park benches and passing busses, the House of Fabulous beckoned to "boys who should have been girls." Now he was being presented with the perfect cover! When he responded by saying, "I don't think so," the lie was so transparent that Terry began to wonder about Doyle's acting ability.

Their entrees arrived, and Terry weighed his next words while he twirled capellini pomodoro onto his fork. He was certain now that Gail Chestnut was right about Doyle Rogers. The man was obviously yearning to explore his feminine side, but afraid or ashamed to do so. Terry also felt sure that Madam Fabulous would have no trouble transforming Doyle into an attractive woman. All he needed to do was get him in the door. "The House of Fabulous made me the woman I am today," he said, staring at Doyle above his wine glass.

"Is it some kind of beauty salon?" Doyle asked with feigned ignorance. He had visited the House of Fabulous web site countless times, and a dog-eared copy of "Boys Who Should Have Been Girls" by Madam Fabulous was kept in a drawer in his nightstand.

Terry played along. "Sort of. Maybe it takes one to know one, but I can tell that you would make a spectacular woman." He drained his glass and drummed his manicured fingers on the tablecloth. "Wouldn't you like to try it, just once?"

"What makes you think I'd want to?"

"Because it's such a rush! Look at me, Doyle. It feels so good to dress up like this." Terry crossed his legs with a rustle of nylon, poking one of his high heels out from under the tablecloth. "Do you know what I like about it the most?"

"What?" Doyle whispered.

"Paying back Mother Nature for the trick she played on me. When I was a little kid, people used to tease me by saying, 'You should have been born a girl.' Maybe they were right. Now, when I get dressed up like this, nobody can tell that I'm really a guy."

After years of frustration and denial, the repressed feelings finally poured out of Doyle's tortured soul. "Do you really think I could pass for a woman?" he asked in a quaking voice.

"Take it from me. You'll be a Fabulous Girl."

* * *

They agreed to meet in Doyle's office the next morning to plot their strategy. After he got back to his apartment, Terry found Madam Fabulous's lavender card in his black purse and glanced at his slim wristwatch. It was after ten, but he took a chance and called the number on the card. He waited while it was routed to another extension. "House of Fabulous," the familiar voice answered.

"Madam, it's Terry. I'm sorry to call you so late."

"Nonsense, dear! I'm dying to hear about your dinner date. Tell me everything!"

"Oh, it was wonderful. Madam Fabulous, I have another emergency for you."

"What is it?"

"Can you perform another miracle tomorrow morning? Not for me, for somebody else."

"Bless your heart. Let me consult my palm pilot." A pause. "Tomorrow morning is booked solid, but the afternoon is wide open. Tell me about the project."

"He's a natural. About my height and weight, a lot better-looking, and a trained actor to boot."

"Oh my. You are becoming my favorite customer, Terry. Tell your friend to come at one o'clock, when the Mistresses get back from lunch. What's his name?"

"Doyle. I'll be with him. I need you to give me some of those curves that can stop traffic."

"We'll be waiting for you."

Terry hung up and started to get ready for bed. After hanging up his dress and peeling off his lingerie and stockings, he removed his makeup with cold cream and freed himself from the hated gaff. Dressed in his blue satin nightgown and panties, he crawled under the covers and was about to switch off the light on his nightstand when the telephone rang. It was Gail Chestnut.

"How was your big date?" she giggled.

"I do believe you're jealous," Terry bantered back in a girlish voice.

"You bet I am! Did you give him a goodnight kiss?"

"No! It was strictly business, Gail."

"Hmmm...sounds like Mr. Rogers' secretary was right about him. No straight guy could have resisted a girl as hot as you." Her voice was incredibly sultry, and Terry felt himself stirring. He looked under the covers to see a tent forming in his nightgown as his penis strained against his satin panties.

"Do you really think I'm hot?" he asked.

"I'm getting hot right now just thinking about you."

"That makes two of us."

"What did you wear tonight?"

"Just a dress."

"What's it like?"

Terry felt himself starting to lose control. He tugged the waistband of his panties down and freed himself as he cradled the phone on his shoulder. "It's white with little blue polka dots. It has sort of a gathered waist and a princess collar."

"Sounds cute. Do you have it on now?"

"No."

"What are you wearing?"

"A nightgown and panties."

"Yum! Pull your panties down."

"I already did."

"Naughty girl! Are you touching yourself?"

"Not yet," Terry moaned as his penis twitched in anticipation.