Caught between a rock and a high heel 09

“Good morning, Kiera,” Tom Watkins announced as Kieron nervously shuffled into his office. “Please, take a seat, my dear.” Kieron thanked the older man while forcing a smile before trudging over to the sofa to sit down.

Once seated, Kieron took a moment to get comfortable, folding one pantyhosed leg over the other at mid-thigh. He then tugged at the ends of his jean shorts, which were a little too short for his liking but in his opinion much better than a skirt.

Kieron had picked out his outfit that day himself, well sort of. After talking with Becca the previous evening, he had convinced her to let him pick out his own outfits, saying he was never going to learn about fashion unless he practised. She agreed but only if she had the right to veto anything she deemed to be inappropriate for the workplace or the character Kieron was supposed to be portraying. So after four changes and a lot of critiquing, he had ended up in a pair of short denim shorts and a tight leopard print top. A little flashy, perhaps for a typical office, but where he now worked everyone seemed to be a little more relaxed when it came to traditional office attire. The rest of his outfit consisted of a pair of semi-sheer black tights and ankle boots with a short blocky heel.

Trembling with nerves, Kieron tried to hide his fear as he looked up at his new boss Mr Watkins, who sat behind his large oak desk, scrutinizing him from head to toe. When Tom reached his feet and saw the ankle boots he was wearing, a frown appeared on his face. "You're not wearing the shoes I gave you," he said, his voice tinged with frustration.

Bracing himself for Tom's reaction, Kieron looked down at his feet. "Oh, yeah, I like already did that review thingy you asked me to do. I sent it through to your email this morning," he explained.

"Oh," Tom exclaimed, sounding surprised, his face contorting as he furiously clicked on his mouse to open his emails. Kieron watched on nervously, feeling as if time had come to a complete standstill as Tom slowly read his review. As he waited, Kieron tried to steady his trembling legs by pressing his palms against his silky thighs, feeling as if he might pee his panties at any moment. But just when Kieron thought he couldn't take the tension any longer, Tom suddenly burst into laughter, the sound easing the heavy atmosphere in the room. "A very interesting write-up," Tom declared, still chuckling. "Not what I was expecting, but a thoroughly entertaining read and a unique perspective on the struggles a woman faces while navigating the world atop fashionable shoes."

On the couch, Kieron's mouth fell open in surprise. Tom wasn't the only one taken aback in that moment. Kieron had spent the previous evening describing his uncomfortable experience from the day before, stumbling around on tired legs as even the most trivial tasks had become a chore. He had expected Tom to dislike the piece, but instead, Tom seemed to find his pain and discomfort amusing. "I'll send this over to our editor for a quick review and then have him post it on the website to see how it trends," Tom cheerfully announced. "To be honest, I wasn't expecting you to get this back to me so quickly, but now that I know you can produce this type of quality in such a short space of time, it's given me an idea. I want you to write a piece for me every day, describing your experiences like a diary. What do you think?"

"Every day!" Kieron exclaimed. "But what will I write about?"

"Hmmm. You're right," Tom said, stroking his chin. "If you're going to keep producing compelling pieces like this one, you'll need some activities while you experience the products."

"Products! activities!" Kieron repeated, completely lost.

"Oh, sorry," Tom said with a smile. "I'm bombarding you with information. Don't worry about what you'll be doing for now; leave that to me to organize. For today, work with Gina again."

"Erm... okay," Kieron said in a gloomy voice, realizing that not only had his plan to get let go from the company failed, but it had backfired, giving him even more work to do. As he stood up, preparing himself for another day of being bossed around by Tom's secretary, Gina, Tom stopped him in his tracks. "Whoa! Not so fast," he said. "Before you go, I've got something for you."

"For me!" Kieron exclaimed, horrified as he watched Tom reach under his desk before revealing the scariest pair of high-heeled shoes he had ever seen. Plonking them down on his desk with a thud, he looked over at Kieron with a sly smile on his face.

(See image 17)

"With these, you now possess two pairs of beautiful shoes," Tom declared. "Rotate them each day and continue with your daily tasks. I am eager to see if your opinions change after a few weeks of wearing them."

"A few weeks!" Kieron exclaimed, his mind filled with fear at the thought of standing in the towering heels on Tom's desk, let alone having to wear them day in and day out.

"For now, yes," Tom nodded. "We will reassess the situation after seeing how your pieces trend. And take this as well," he added, reaching back under his desk to produce a large cellophane-wrapped box. "I have been told that these are top-of-the-line products. I know you do not typically wear much makeup, but that will only make for a more interesting article. Maybe you could try some different looks and see if people treat you differently. You can decide on the details, I'm sure you have some ideas of your own to contribute to the project."

Left speechless, Kieron stared at the desk in shock, unable to comprehend what he had just heard.

"Well, if everything is clear, I will leave you to it," Tom announced, clapping his hands and standing up. "I am very excited to see where this little project will lead. Do not worry about writing anything today but try to get into the habit of making notes on any interesting occurrences or thoughts. Let's meet again at the same time tomorrow."

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As Kieron minced out of the office building that evening, his troubled mind was only provoked further by the incessant clicking of his tortured feet. It had been a gruelling afternoon of menial tasks as Gina took full advantage of having an extra set of hands. He had been sent on countless coffee runs, forced to engage in small talk with colleagues while delivering assignments, and had lost track of the number of times he was sent to the copy room. Each one of these occasions had been a nerve-wracking experience for the young crossdressing Irishman. Every head that turned as he sashayed by, wiggling his hips, felt like an attack on his masculinity. And every comment about his unconventional footwear made him blush heavily through his thick makeup-covered face.

After leaving Tom's office, Kieron had called Becca, who listened patiently as the babbling young man poured out his frustrations. Though her advice wasn't exactly what he wanted to hear, it did make sense. She suggested he look up a makeup influencer she liked and copy her looks. That way, he could test out his new products and get step-by-step guides on how to apply them. So, in one of the only moments that day when he got to rest his weary legs, Kieron found a quiet corner and experimented with the makeup. At first, the task seemed nearly impossible. After messing up a few times and getting frustrated as he had to wash his face and start over, he almost gave up. However, encouraged by Gina, who found his idea of trying different looks amusing, he persevered, ending up with the overdone, caked-on look that now adorned his face as he tottered out of the building, annoyed, hungry, and frustrated.

(See image 18)

As he stumbled towards the waiting taxi, Kieron couldn't help but wonder how his life had taken such a drastic turn. He braced himself for the inevitable chit-chat with the driver as he awkwardly climbed into the car, dreading the prospect of having to discuss his flashy footwear yet again. All he wanted to do was get home and lock himself in his bedroom, the only place where he could relax and be himself, even if it was cluttered with feminine products belonging to the real Kiera.