Caught between a rock and a high heel 05

The next morning

Prying open his puffy eyes, the sinking feeling in the pit of Kieron's stomach returned as he suddenly realised where he was. There on the floor lay the same shaggy white rug. And there on the far wall, high up on a shelf, sat a collection of stuffed bears. He was still inside his femininely decorated prison cell, and he felt like screaming.

All night he had tossed and turned as his mind conjured up horrific images of what the next day would bring. Finding sleep difficult, he had willed the morning to come, but now that it was here, all he wanted to do was stay in bed and hide. Anything to avoid what was to come!

Hearing a knock, Kieron turned to see Becca pop her head into the room. “Breakfast is on the table,” she said with a kind smile. “See you in five, ok?” Kieron nodded and forced a smile before watching Becca's head disappear out of sight.

Pulling back the sheets, Kieron groaned as he looked down to see the layer of thin satin material covering his silky-smooth body. He hadn’t wanted to wear a nightdress to bed, but Becca had insisted. Saying something about him having to live and breathe Kiera's life until the day of the dreaded interview. Whatever that meant!

Feeling his bladder about to explode, Kieron slipped on a pair of fluffy pink slippers that perfectly matched the colour of his night dress. Up on his feet, he then shuffled towards the bedroom door, where he slipped on Kiera's soft white bathrobe. Once on, he set off towards the bathroom, not wanting to admit that the soft fluffy material surrounding his feet and body was actually rather comfortable.

After relieving himself and freshening up a little, Kieron found Becca eating her breakfast by the kitchen table. Reluctantly he sat down to join her.

“How did you sleep?” She asked, trying to make conversation.

“Not great,” Kieron grunted back while shaking his head.

Becca snorted. “Understandable, I guess,” she replied while moving a box of cereal closer towards Kieron. “Here, eat something. Then we’ll start your training.”

Kieron puffed up his cheeks and blew out slowly. “Becca, I’ve been thinking. I remember what you said yesterday. But this is a bit crazy, don’t you think? Perhaps we could talk to Kiera and think up another solution?”

“It is an unusual solution, I give you that,” said Becca raising her eyebrows. “But I do think it'll work.”

“How can this possibly work?” Kieron moaned loudly. “I’m not a girl! I’m just going to embarrass myself, and you, for that matter. Come on! There must be another way.”

“Hey! This can and will work,” said Becca in an authoritative tone as she placed down her spoon. “And remember, you’re the one who filled my impressionable sister’s head with notions of travel. So, if you want your stuff back, you better change that attitude. Because I’ll tell you now, if you embarrass me or jeopardize my job, I’ll ruin you!”

Then, like a switch being flicked, Becca’s tone reverted back to being all bubbly and friendly. Picking up her spoon, she looked over at a wide-eyed Kieron, and smiled. “But that’s not going to happen, is it?” she added. “As much as you probably don’t want to hear this, you’ve got the looks to pull this off. You’re short for a guy and have soft facial features. After a little posture and vocal training, you’ll easily pass as a woman. But for this to work, I need your full co-operation. Do I have it?”

Shaking his head, Kieron wanted to yell fuck you and storm right out the door. But dressed in Kiera’s sleepwear with no money, luckily the logical part of his brain kicked in. “I’ll do it for five-hundred quid,” he replied with as much assertiveness as he could muster.

“I don’t think you’re in much of a position to argue,” Becca replied before rubbing the back of her neck. “But I tell you what. You pull this off, and I’ll give you fifty quid. That’s enough for a few outfits down the charity shop.”

Breathing heavily through his nose, Kieron took a second to ponder her offer. “Fifty quid and a plane ticket to Ireland,” he countered while leaning over the table.

“Done,” Becca announced. “Now eat up so we can get started.”

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“Much better,” praised Becca, nodding her head. “That’s it! Pause between each question. Play with your hair, rub your leg, and bite your bottom lip.”

Feeling physically uncomfortable and mentally exhausted, Kieron simultaneously bit and released his painted bottom lip, ran his left hand through his synthetic hair, and ran his other down the side of his pantyhosed calf.

(See image 9)

“So, Kiera. Can you tell me a time when you’ve used your femininity to your advantage to solve a problem in the workplace?”

“What kind of question is that?” Kieron replied as he screwed up his made-up eyes in frustration. “No one is going to ask me that!”

Becca tutted while shaking her head. “Perhaps, but we’re practising getting you to think and feel like a woman. The same reason, as I’ve already explained to you, why you’re wearing makeup and are dressed in a skirt. So, can you please stop delaying and answer the question?”

“I... I don’t know how,” replied Kieron, cringing as he ran his hand down his nylon-covered thigh. Before today I’ve never felt feminine. And all this. It’s… It’s a lot. These clothes feel too soft and are tight in all the wrong places. And I know what you said earlier about the skirt, but can’t I just wear pants? I’ll feel more comfortable in pants! Women wear them all the time. And if I feel more comfortable, I’ll be less likely to mess up.”

Bringing up her hands, Becca sighed before slowly dragging them down her face. “Look, I know this is all new to you, but you also agreed to give it your all. If this is going to work, we need the interviewer to believe, without a doubt, that you’re a woman but at the same time deem you unsuitable for the role.”

Narrowing his brow, Kieron folded his arms and tilted his head to one side. Seeing his confusion, Becca tried to break it down further. “A skirt will help you walk like a woman and remind you not to sit with your legs wide open. We'll do your make-up and pick out an outfit that makes you look a little ditzy. Then if you give a few silly answers, it won't matter.”

“What!" An appalled-looking Kieron cried. "You want me to look and act like some dumb bimbo? blonde hair and high heels?”

“Blonde hair isn't necessary your wig will do. But heels! We’ll get to them this afternoon,” Becca said while smiling.

“Oh, come on. I wasn’t serious!” Kieron cried. “I don’t need heels!”

“You do, but we’ll talk about that after lunch,” stated Becca, lifting her hand up to bring an end to the matter. “Now, Ms Frost, tell me about a time you’ve used your femininity to solve a problem in the workplace.”

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After hours of prancing around the house doing chores, Kieron stopped to catch his breath. Not only did he despise housework, but to make matters worse, he had been doing it wearing a dress and heels. The feeling of having the shoulderless dress surrounding him felt weird. And its knee-length accordion-style skirt was constantly flapping against his smooth legs as he tried to vacuum the carpet and dust the shelves. Then there were the ridiculous shoes he'd been forced to wear! Black, patent, Four-inch pumps that pinched his toes and slipped at the heel. Saying that they had impeded his movement would be an understatement. Every step at first had been accompanied by a wobble, and the concentration level needed not to roll an ankle had almost driven him crazy. But as he slowly improved, he had to begrudgingly admit that Becca had been right. The only way to master anything heels was to just do it. After a day and a half of practice, he was getting better.

“Why are you standing there?” Asked Becca as she entered the room to find Kieron leaning against a wall, resting his cramping calves, and throbbing toes.

(See image 10)

“I’m just waiting for the washing machine to finish,” Kieron replied as he pushed down hard on his heels to stop his exhausted legs from shaking.

“Ok, but why are you standing around,” Becca lectured. “You should be using the time to practice. You know that the interview is tomorrow, right?”

“Awww,” Kieron sighed. “Give me a break, will ya?” I’m trying my hardest here, you know. I’ve hated every minute of this, but I've still done everything you’ve asked of me. I just need a minute, ok? Otherwise, I’m going to fall and break an ankle. But perhaps that would be a mercy. At least then I can skip this God-forsaken interview!” The outburst was followed by a few seconds of awkward silence.

“Sorry,” Becca said, softening her tone. “You’ve been doing really well. Your walk is so much better now that you’re taking smaller steps and swinging your arms."

"You really think so?" Kieron replied feeling a mixture of pride and embarrassment.

"Oh yeah," Becca shot back. "It takes a big man to try at becoming a woman, like you."

"But... do I look ok?" Kieron asked while looking down at his high-heeled feet.

"You'll look passable," Becca replied with a smile. "That padded bra helps with your shape. You just need to perfect your voice."

Kieron sighed and scratched his head. He had been trying to talk in a higher pitch, but it was hard!

“Here, come sit with me for a minute,” Becca said, pointing towards the sofa.

Trotting over, Kieron smoothed his skirt along his pantied backside, just like he’d been shown, and sat down. He took a moment to arrange himself, folding his legs at mid-thigh and positioning his skirt right. When ready, he turned to face a smiley Becca.

“What!” He exclaimed, feeling embarrassed. "That's what you want, right?"

“Ur-huh," Becca mumbled while nodding. "I'm just.... starting to think that this might work, that's all.”

"That's all!" Kieron cried. "If you're only just thinking that now. What the bejeezus have we been doing all this time?" Becca laughed, and after a few seconds, Kieron started chucking along.

“Ok, we’re going to do the scales again,” Becca announced as the laughter started to die down.

Kieron groaned. “Again?” But I feel ridiculous doing that. And my throat's still scratchy from last time!”

“Good!” Becca replied. “That means it’s working. Your vocal range is extending.”

“Don’t you have work to do or something?” Kieron asked, trying to get out of the humiliating and painful exercise.

“One of the perks of working from home is that I get to take breaks whenever I want,” said Becca, making herself comfortable. “Now, stop stalling and begin. Start deep and give it as much volume as you can.”

Seeing that Becca wasn’t likely to back down, Kieron took a deep breath before letting out a deep, gargled hum.

“It’ll be over soon,” he told himself as he slowly raised the pitch of his voice in time with Becca’s ascending finger. “This time tomorrow, it’ll all be over!”