Caught between a rock and a high heel 20

Deep in thought, Kieron staggered out of the restaurant's entrance and into the embrace of the night. The cool breeze gently grazed his smooth legs and played beneath the hem of his dress, sending shivers down his spine as he scanned the street for his ride. Spotting the sleek black sedan in which he had arrived, parked discreetly at the end of the street, he set off without hesitation. The coat he had arrived in was now a distant memory.

The crisp night air continued to chill his exposed arms and legs as Kieron minced towards the car, his aching feet perched atop a pair of seven-inch designer heels instinctively avoiding the pavement's cracks. Gripping his purse tightly in his impeccably manicured fingers, the rhythmic click-clack of his heels on the ground and the unfamiliar jangle of his earrings filled his ears, but all of it faded into the background. Consumed by the shock of the night's events, Kieron longed for the sanctuary of Becca's apartment where he could lock himself away from the world and process what had just happened.

(See image 39)

The day began ordinarily enough, at least by the standards of the past few weeks. Kieron rose and went through his morning routine, meticulously transforming himself into the fashion-conscious office girl he was now compelled to embody. He then went through the motions of a fairly typical Friday at the office, composing reviews on the latest dresses and shoes he had been wearing and sharing delightful lunchtime conversation about travel with Alain. However, it was after work that Kieron's day took a dramatic turn for the worse.

Ever since learning what Tom Watkins expected of him that Friday evening, the event had haunted Kieron's thoughts. And unfortunately, the reality turned out to be far worse than he could have ever imagined! Promptly at 4 pm, a chauffeur-driven car swept him away for what had promised to be an evening of pampering and luxury. Instead, the unsuspecting Irishman found himself transported across the city to a dressing service. There, he was stripped of his clothes and makeup, only to be painstakingly redressed from the skin out – an intensely nerve-wracking experience for someone concealing something between their legs that had no business being there.

As Kieron stepped out of the building to rejoin his ride, he noticed the driver's raised eyebrows, signalling that his appearance was, as he thought, a little over the top! With his hair piled atop his head in an intricate braided style and his eye makeup extending outwards to form the most dramatic cat-eye look he had ever seen, Kieron couldn't fathom what the stylist had intended to accomplish. He was even less pleased with the outfit he had been given to wear. His warmer business skirt and jacket had been replaced with a slinky white dress, leaving him feeling exposed. Ironically, the only item that remained from his original ensemble was the very thing he most wished to be rid of – the agonizingly uncomfortable shoes on his feet.

Filled with apprehension, Kieron sank into the plush back seat of the luxurious car as it drove to the next destination. He wished he could be anywhere else, but with no choice other than to endure the evening, he steeled himself and tottered into the Michelin-starred restaurant nestled in the city's heart. Soon, he found himself being escorted through the opulent dining room, the grandeur of his surroundings providing no solace for the unease that gripped him.

The sound of Kieron's towering heels reverberated throughout the majestic room, drawing curious glances from patrons who wondered if the elegantly dressed woman passing by might be a celebrity or someone of significance. Kieron paid no heed to the stares, focusing instead on Tom Watkins, who sat at the far end of the room engrossed in his phone. As Kieron approached, Tom looked up, and a wide grin spread across his face.

"Kiera!" he exclaimed loudly. "You look absolutely radiant tonight!"

Muttering a thank-you, the skirted man was caught off guard as Tom sprang from his seat and planted kisses on both of Kieron's cheeks. With his nerves now heightened, Kieron stepped aside as the maître d' pulled back his chair, allowing him to sink into the plush seat. However, he found no comfort from the luxurious surroundings.

For the next five minutes, Tom chatted animatedly while his phone lay dormant. However, his words failed to penetrate Kieron's anxiety-ridden thoughts. When a waiter appeared to take their orders, Kieron found it almost relieving when Tom took the initiative and ordered for both of them. In his current state, Kieron could hardly decide what to eat.

"I hope you don't mind?" Tom asked as the waiter retreated. "I want you to try some of their specialities. The seafood linguine here is award-winning."

"It's fine," Kieron mumbled, glancing up through his fluttering lashes before lowering his gaze again.

"So, perhaps you're wondering why I've asked you here today?" Tom blurted out to fill the silence. His curiosity piqued, Kieron looked up once more, eager to uncover the purpose of their meeting.

"Well, you've been doing such an outstanding job lately, I thought it would be a great opportunity to celebrate," Tom declared, grinning as he knew he had the feminized man's undivided attention. "Since you joined us, profits have increased, Alain has become more productive, and most importantly, I arrive at work each day with a smile, just thinking about you."

As the words sank in, Kieron's makeup-adorned eyes widened, and a small gasp escaped his plump lips.

"For that reason, I'm going to cover the costs as you continue to transition," Tom continued. "Consider it a bonus, if you will."

"My... my... transition," Kieron stammered, his body trembling. "What do you mean?"

"Hormones, any surgeries you need, even the final snip," Tom explained, sounding pleased with himself. "We can write it off as company expenses."

"You know?" Kieron gasped in utter shock at what he was hearing. "How did you find out that I'm a... a..."

"A transwoman," Tom interjected. "I've known since the first time we met, when your wig kept slipping down. But don't worry, it's not a problem. I'm drawn to women like you, which is why I've been trying to help with your transition."

"Help?" Kieron muttered, beginning to hyperventilate as the reality of the situation washed over him.

"Yes," Tom replied cheerfully. "The spa and salon appointments, the vampire breast lift – I thought they'd be right up your alley. And no need to thank me," he added, leaning across the table. "But if you did, I have a 10-year-old Pinot Noir chilling back at my penthouse. We could make a night of it?"

"Eww, no!" Kieron yelled, his long-nailed hands flailing in outrage. "I'm not a trans woman, and how dare you do all those things without my permission! You're sick!"

"Stop!" Tom commanded, his hands flying across the table in a flash, pinning Kieron's to the surface. "The only sick person here is a little boy who likes to play dress-up to tease older men," he added in a hushed tone, his mood shifting to anger. "I'm a man who gets what he wants, Keira, and I've invested a lot in you. So here's what's going to happen: We'll finish our meal, and you'll smile and be pleasant. After that, you'll accompany me back to my penthouse, where tonight – and any other night that I desire – I'll use you as I see fit. You won't mention this to anyone at work, and you'll continue to progress toward the final operation. Once that's done, you'll be a complete woman – my woman!"

"You're sick!" Kieron squeaked in terror, struggling to free his arms from Tom's iron grip. "And why would I do that?"

"Because if you don't, I'll ruin you, Kieron Walsh," Tom threatened, a look of madness in his unblinking eyes. "I'll burn your pathetic life to the ground and drag your friend Becca down with you."

Hearing his real name spoken, Kieron's body froze, and his mind raced with two dominant thoughts: Were his family and friends back home about to discover what he had been doing? And what would happen to Becca?

"Ok," Kieron conceded, nodding.

"Ok, what?" Tom demanded, still glaring.

"Ok, you win," Kieron replied, his voice laced with sorrow. "I'll do what you want, but can I at least use the restroom first?"

Tom slowly released Kieron's wrists, a cunning smile crossing his lips. "Of course, my dear. Go freshen up."

With trembling legs, Kieron pushed himself upright, his stilt-like heels wobbling beneath him. Silently, he pushed back his chair with the backs of his thighs and turned. Focusing intently on each step, he crossed the room, his legs threatening to buckle, and his eyes fighting back tears.

Now functioning on autopilot, Kieron felt like a passenger in his own body. He teetered past the restroom, out of the restaurant entrance, and onto the street. Moments later, he found himself in front of his ride for the evening as the driver held the door open for him.

"Home, please," he mumbled as he climbed in and immediately kicked off his torturous heels. Rolling down the window for some fresh air, the shell-shocked Irishman extended his manicured hand outside, closed his eyes, and struggled to suppress the urge to vomit.

(See image 40)

As the engine roared to life, Kieron felt his stomach churn with nausea. He was alone and lost, unsure of what to do next. Desperately, he wondered if there was anyone he could turn to for help, someone who could pull him out of the enormous hole he had dug himself into.