KK's Quickies: Sexist Tech Bro to Sexpot Secretary (3/3)

By this point, word had spread through the office of what exactly was going on behind Mac’s closed blinds…so when the start-up boss finally emerged, every single head in the building turned eagerly in his direction. They were met by an incredible, almost surreal sight: their angry, macho boss, not only divested of his treasured facial hair, but expertly made-up with high-end cosmetics, swishing out of his office in an attractive, short green dress that swirled enticingly about his waxed-smooth thighs and contrasted attractively with his flowing wig, which matched his own hair color almost perfectly.

“Listen up!” Mac barked, in a voice that was not feminine in the slightest, jabbing his finger at his gawping employees. “What you’re seeing right now is a testament to my dedication to this company, but I promise you, this is the first and last time you’ll see me wearing a dress…and if any of you breathe a word of this, to anyone, you’ll be out on your ass so quick you won’t have time to blink, understood?” He took a deep breath. “Also, it’s for charity,” he added. “Now, back to work!”

His shocked employees did their best to avert their gazes, but it was tough to do, and as Mac and Penelope made their way toward the elevator doors, most of the RoboPogo work-force couldn’t help but watch, stunned not just by the fact that their macho, misogynistic leader was in drag, but by the fact that, all things considered, he didn’t look half-bad. Who knew their boss had such pretty legs?

#

Mac had always prided himself on his composure and adaptability in high-stress situations, but he had to admit he felt more than a little nervous on his way to the Magnates in Drag event. The sheer and utter barrage of foreign, feminine sensations threatened to overwhelm him. Everything from the taste of his waxy pink lipstick, to the chilly air-conditioning caressing his bare legs beneath the hem of his dress, was deeply unsettling.

With Penelope’s guidance, he managed to exit the vehicle without flashing his panties to the world…but soon after, she abandoned him.

“I’m sorry, I have to get to the ladies’ room,” she said, in a pained whisper. “It’s that time of month, so…”

Mac gave a mighty shudder. “Don’t give me the details,” he snapped. “Just be quick about it.”

“Here, I put your phone and wallet in here,” Penelope said, handing him a small green handbag. “I’ll catch up as quickly as I can!”

With a grimace of distaste, Mac accepted the feminine accessory. Then, gathering his nerve and rehearsing his best schmoozing lines in his head, he followed the sounds of soft music and conversation until he reached the grand hall. The doorman gave him a slightly startled look as he approached, but one imperious glare assured he was let inside…at which point Mac wished, desperately, that he had been refused entry.

Just as promised by the event’s website, the room was full of business magnates rubbing shoulders and shaking hands…but in complete contrast to the photos Mac had seen, every single one of them, save he himself, was clad in a perfectly normal, perfectly masculine, perfectly tailored suit. Mac’s lipsticked mouth fell open in utter shock, as every head in the room, attracted by the puzzling appearance of the newcomer, turned in his direction.

Overwhelmed by the surprise, it took a moment for the gears inside Mac’s brain to start turning – but when they did, he realized immediately that he had been had. “That bitch!” he breathed, imagining Penelope giggling in the ladies’ room. “And she couldn’t have done it alone, either…”

He whipped out his phone, staring down at the photos from last year’s event, and finally saw the tell-tale signs of expertly done photo manipulation. Some conniving techie had managed to put the faces of actual business magnates onto the bodies of a bunch of drag queens, in convincing enough fashion to fool Mac completely.

He looked up again, his face turning as red as his hair, and to his absolute horror, the confused looks on the faces of his fellow entrepreneurs and executives were shifting towards looks of amusement, instead.

“Wait a second,” he heard someone mutter from the crowd. “That’s not…that can’t be…”

“Mac McMurphy!” someone else whispered. “What the hell…”

Paralyzed by fright, Mac could only stand there in his flirty dress and high heels, staring back, open-mouthed, at the men he’d thought would be equally feminine in appearance. He had to think fast, or his reputation would vanish down the drain in an instant! If he pretended he was pulling a prank, maybe, or that it was some sort of bizarre promotion for RoboPogo’s latest innovation…

But before he could so much as clear his throat, a large hand appeared on his shoulder – and when he looked up, he was staring right into the face of his business idol, Gill Mathers! Mac went pale beneath his makeup. He’d assumed the photo of Gill Mathers had been inserted specifically to lure him here, but against all odds, the famous CEO was indeed in attendance…but he was certainly not in drag. Bracing himself for disaster, Mac’s waxed-smooth legs began to tremble.

“Incredible!” the CEO exclaimed, in a booming voice that drew even more attention to the feminized Mac. “How could I have gone all this time without knowing RoboPogo was run by a transgender woman…” His smiled widened. “And that she was so stunning?”

Mac nearly fainted on the spot, and had to cling instinctively to Gill Mathers’ arm in order to not fall over in shock. The CEO seemed happy enough to support him, using his powerful frame to bear most of Mac’s far smaller weight. Before he knew what was happening, the CEO was steering him through the gathering, towards the back of the hall, to get him a glass of water.

“My apologies, my dear,” Mathers said. “It seems I’ve startled you quite badly! It’s just that I had no idea, when I saw your company mentioned in the news…”

Mac was now doubly shocked, and under other circumstances, would have been over the moon to discover his business hero knew of RoboPogo’s existence…but under the current circumstances, wearing a dress, wig, and heels, he was horrified.

“Coming here as yourself, knowing you would be surrounded by a bunch of macho men in suits, must have taken incredible courage!” Mathers continued. “I’m quite floored by your bravery, my dear. I’m a huge ally of the LGBTQ community, and I’ll support you and your company in any way I can…starting, perhaps, with a drink for its lovely founder?”

Mac could only stare for a moment, floored by the sudden turn of events. Gill Mathers wanted to support his company, but thanks to Penelope and her accomplices, he thought that Mac McMurphy, man’s man and total tech bro, was transgendered! But if there was ever a time to prove his composure and adaptability, it was now…he would be able to explain the whole thing soon enough, he was sure, but for the moment, the important thing was that he had his foot in the door…even if that foot was wearing a stiletto heel!

Mac cleared his throat and gave the powerful CEO an awkward smile. “Sounds good,” he said, in as high-pitched a voice he could manage. “Uh, I’ll have what you’re having.”

The CEO grinned.

#

One Year Later...

As Mac made his way toward the same grand hall he had blundered into wearing a dress and heels just one year earlier, the former start-up boss tried, once more, to pinpoint how exactly things had gone so very, very wrong. That fateful day had been a whirlwind of activity: not long after meeting Gill Mathers, the powerful CEO had insisted on whisking him away to a more private location to talk business.

All too eager to get away from the stares of his fellow tech entrepreneurs, Mac had agreed…and when the CEO, impressed by Mac’s accomplishments and business acumen despite his young age, offered to not only absorb RoboPogo into his own company, but offer Mac a high-paying position working directly underneath him, Mac had leapt at the chance.

The wrinkle in the proceedings – that Gill Mathers believed he was hiring a transgender woman – was one Mac was sure he could smooth out in short order. After all, even if hiring an LBGTQ employee was a great business move, Gill was hiring him for his impressive talent and potential, not his supposed gender identity, right?

But when news of his hiring, splashed across every business rag in the country, mistakenly named him as “Macy McMurphy”...and was accompanied by a photo of him in his green dress, smiling nervously beside Gill at the networking event…Mac began to suspect he was in over his head. Unwilling to jeopardize his shot at the big-time, he decided to embrace the charade temporarily, then quietly “de-transition” once the hubbub died down.

Unfortunately, his new boss had other plans: before Mac knew what was happening, he was on a company healthcare plan that supplied him not only with female hormones, but a voice and decorum coach, a personal wardrobe consultant, and all sorts of experts ready to help guide him through his so-called transition. When Mac balked at the excessiveness of it all, Gill merely told him that as a high-ranking employee, it was his responsibility to present an attractive, professional image to the public!

Every time Mac was on the verge of admitting the truth and calling the whole thing off, Gill seemed to find a new carrot to dangle in front of him, whether it was rights to the private jet or vacations to Gill’s private island in the Bahamas. He quickly realized that the girlier he acted, and the more he committed to his “transition,” the more positive attention the CEO lavished on him. Finally, against his better judgment and after much badgering, Mac even agreed to a few simple, easily reversible cosmetic surgery procedures.

Which was why, just a year after promising his employees that they had seen him in a dress for the first and last time, Mac was all dolled up in an expensive, very revealing green cocktail dress that presented his silicone-stuffed cleavage to advantage. And that wasn’t the only change, either: the days of wearing wigs were long behind him, as now he had long, luxurious hair extensions tumbling down his bare back in a glamorous, perfectly styled cascade. A nose job and minor work on his chin had eliminated any lingering trace of masculinity from his features…and with his fluttering eyelash extensions, puffy, collagen-enhanced lips, and perfect makeup, he was now utterly stunning.

The hormone replacement therapy, aided by a strict diet and work-out regiment, had transformed the rest of his body, as well: he now had slender, dainty arms, a tiny waist and toned midriff put on display by the revealing cut of the dress, and rounded, feminine hips to complement his pretty legs. His manicured feet were encased in five-inch heels once more, but after a year of femininity, he now handled the spikes like a pro! Massive solid gold earrings, as well as a matching bracelet and expensive designer handbag, completed his “look.”

All in all, there was no shred left of the brash, macho tech bro who’d so enjoyed harassing his female employees just one year ago…he had been utterly replaced by a gorgeous red-head in a sexy cocktail dress. The get-up was a tad too revealing to be worn by a powerful executive, which Mac had desperately pointed out to both his stylist and to Gill, who had presented him with it as a gift…at which point, he’d received the worst surprise yet.

The CEO explained that while “Macy” certainly had all the potential in the world, now was simply not the time to take on a high-stress, high-powered position in the company. Rather, he wanted “her” to focus on her personal transition, to ensure she emerged from her metamorphosis as a sexy, confident, full-fledged woman. And in the meanwhile, “she” could pick up plenty of useful knowledge by working as his personal assistant!

Just like that, Mac’s dream of being Gill Mather’s second-in-command took a sharp turn, as he instead found himself fetching coffee, organizing meetings, and generally scurrying around at the CEO’s beck and call, all in high heels and tight skirts. One essential part of his duties was escorting Gill to all his fancy functions and fundraisers, always while looking his feminine best…but he had never worn a dress quite like this one before.

As he anxiously bit his gloss-coated lip, Gill – the CEO insisted that Mac call him “Gill,” these days, rather than “Mister Mathers” – looked over. “There’s no need to be nervous, my dear,” he said kindly. “You look absolutely ravishing.”

Mac blushed furiously. “Thank you, Gill,” he said, in the throaty, feminine voice he’d worked tirelessly to perfect. “It’s just…well…I think an old, um, employee of mine…might be in attendance.”

“Oh, yes, Penelope Whitling!” Gill said excitedly. “Quite the rising star! She’s done such wonderful things lately, hasn’t she? Between you and I, Macy, I’ve been thinking of poaching her for our own company.”

Mac’s blush deepened even further, and he only managed a weak smile and nod as they entered the gala. Naturally, all male eyes turned to enjoy the sight of a gorgeous red-head in a skimpy dress…even though most of them knew that one year earlier, “she” had been one of the guys! Humiliated by the lustful looks he was receiving, Mac clung timidly to his boss’s arm as they walked into the party.

It didn’t take long for Penelope, dressed in attractive but very professional attire, to come find him, bearing a wide grin. “Macy!” she exclaimed. “So good to see you! My, you’ve certainly changed!” Her eyes dipped toward Mac’s impressive cleavage. “That dress is gorgeous.”

“Th-thanks,” Mac stammered. “It’s, um, new.”

“I bet it is,” Penelope said, giving Gill a knowing wink. “A cutie like you deserves to be spoiled!"

Gill gave a chuckle. “I’ll let you two have a little catch-up time,” he said. “But I’d love to talk business with you later, Penelope.”

“Of course,” Penelope said, laying a confident hand on Gill’s arm. “I have some ideas I’d love to bounce off you, Gill.”

The CEO departed, leaving Mac to stare forlornly after him…unfortunately, Penelope misinterpreted his look entirely.

“Ooh, you have it bad for the boss, huh?” she said, with a teasing smile. “I don’t blame you, Macy. He’s a real silver fox…and he obviously has the means to keep you pampered.”

Mac grimaced in embarrassment. “I don’t know what you’re talking about!” he squeaked, in a girlish parody of his old authoritative bark. “We’re just business partners!”

“Really?” Penelope blinked. “Because from what I heard, you were his sexy little secretary now.” She shook her head. “It’s amazing to think that little prank last year led to all this! The perfect opportunity for you to embrace your real, feminine self just fell right into your lap.” She beamed at her blushing former boss. “Guess it’s the luck of the Irish, right?"

The End