Cousin Amy 04

Chapter 04: Conquering Coffee Jitters

Scott glanced around nervously, barely able to believe he was actually doing this – strolling through his hometown, fully cross-dressed. The array of unfamiliar sensations enveloping his body was both strange and unnerving. Most prominent was the feeling of the thin, dark tights hugging his freshly shaved legs. The nylon fabric slid and tugged against his smooth skin with each step, and the occasional breeze offered a gentle, yet unfamiliar, caress.

The rest of his outfit contributed to the otherworldliness of the experience. A short, brown corduroy skirt, cinched with a belt, fluttered against his thighs. He was acutely aware of its every movement. The soft, olive green turtleneck jumper, tucked into the skirt, felt all wrong, moulding itself over the padded bra, altering his body's contour and making him constantly aware of the feminine underwear beneath.

On his feet were shiny black platform Mary Jane pumps. The straps dug into his ankles, and the unfamiliar height of the heels made every step a cautious, wobbly challenge. Even after days of practice, he struggled to walk – the uneven streets posing a completely different challenge compared to the carpeted floors of Amy’s apartment.

Atop his head, the wig, expertly brushed and styled by Jessica, looked more natural than he wanted to admit. It was a constant annoyance, but crucial to maintaining his disguise. The lipstick, alien in taste, compelled him to compulsively lick his lips in a mix of discomfort and nervousness. His eyes, accentuated with mascara, flickered nervously from one passerby to another, laden with the fear of being recognized as a man in a skirt.

Although he was in a place he knew like the back of his hand, the situation couldn’t have been more foreign. He pondered the trivial yet pressing concerns of how long it would take for his body hair to grow back and whether the 'subtle' reshaping of his eyebrows had crossed into overtly feminine territory.

(See image 07)

"Don't look so nervous," Jessica advised confidently, strolling alongside Scott. "Swing your arms more. Copy me."

"You’re loving this, aren’t you?" Scott replied, his tone tinged with bitterness.

"What do you mean?" Jessica asked, sounding genuinely surprised.

"Any excuse to dress up. Why did you have to pick such a girly outfit? I feel ridiculous!" Scott complained, his shoes clicking loudly on the pavement as he walked beside her.

"Hey, I picked something that wasn’t pink, just like you asked. And I dressed up to make you feel more comfortable. My outfit is a lot flashier than yours," Jessica pointed out.

“Exactly, you’ve been waiting for an excuse to raid Amy’s closet,” Scott shot back, his discomfort palpable.

“Can you stop being so mean to me? Or do you want me to walk off and leave you here?” Jessica’s tone shifted to one of slight annoyance.

Scott let out a sigh. “No, I’m sorry. I’m just not used to all this. It’s a lot.”

“I know, Baby. And you’re doing great. Just remember to use your girl voice,” Jessica reminded him as they passed by an elderly woman who glanced at them curiously.

“Argh!” Scott let out a soft sound of frustration. Despite it being a quiet Thursday afternoon, the town still had its fair share of people. “Is this better?” he asked, raising the pitch of his voice.

“Much,” Jessica confirmed with a nod.

“Now, tell me something. Where is Amy exactly? I never actually asked you. I mean, I found her phone in a drawer earlier. It’s odd she would leave it,” Jessica queried, glancing over at her feminized boyfriend.

“She’s in rehab,” Scott replied in his best imitation of a feminine voice. “They told her she couldn’t take her phone with her. I guess her drug-fuelled lifestyle finally caught up with her.”

“Rehab! Wow!” Jessica said, sounding surprised. “Does her family know?”

“No,” Scott shook his head, feeling the wig tickle his ears. “She made up some story about going on a wellness retreat. Somewhere remote without phone reception.”

“I guess she does seem the type. Rich girl going to rehab. It's a bit cliché,” Jessica mused.

Scott grunted in agreement as they turned a corner. “Hey, I could really go for a coffee right about now. Look, there’s a place just up ahead.”

“Erm… I’m good,” Scott replied nervously, his gaze dropping to his nylon-clad legs and cringe-inducing shoes.

“This isn't up for debate,” Jessica insisted. “You need practice interacting with someone.”

“Jessica, please!” Scott whined, stopping in his tracks. “Don’t make me go in there dressed like this. I’ve come outside like you wanted. I don’t need a coffee.”

Jessica stopped and faced him. “Come on, Scott,” she said firmly. “If you can’t fool a barista in a coffee shop, what chance do you have tomorrow at the meeting? Just use your girl voice, and you’ll be fine.”

Resigned to Jessica's logic, Scott exhaled a deep sigh. "Fine, let's get this over with," he conceded.

With a reassuring smile, Jessica, radiant in her designer ensemble, gently grasped Scott's hand. "Come on," she encouraged, guiding him towards the coffee shop.

Entering the familiar green-and-white chain coffee house, Scott's heart pounded against the fabric of his bra, his breathing growing heavy with anxiety. The sensation of doing something wrong intensified as a few customers glanced over, their eyes reflecting surprise at the sight of two overdressed women on a sleepy Thursday afternoon. The aroma of freshly brewed coffee and the sound of frothing milk filled the air. Jessica confidently led the way to the counter, leaving Scott to follow, his steps unsteady atop his platform shoes.

At the counter, a cheerful barista in a green apron greeted them with a bright smile. “Hi. What can I get you today?” she inquired.

“What do you fancy, Amy?” Jessica said, subtly stepping aside to give Scott the spotlight.

Scott hesitated, his gaze drifting to the menu board as he tried to collect his thoughts. The sensation of his attire seemed to amplify - the tights clinging to his legs, the peculiar feeling of vulnerability without pants, the unfamiliar tightness of the bra. For a moment, all these sensations almost overwhelmed him.

“Erm… two lattes,” Scott finally managed in his best feminine voice, though nervousness tinged his words.

“Short, tall, or grande?” the barista inquired.

“Erm... tall,” he replied, his voice slightly steadier, though his knees trembled.

“With regular milk?” the barista continued.

Scott paused again, glancing at Jessica, who raised her eyebrows expectantly. Gathering his composure, he said, “Soy milk, please.”

The barista keyed in their order. “That will be nine pounds, forty, please. What name for the order?”

“Sco... Amy,” Scott quickly corrected himself, a flush of embarrassment colouring his cheeks.

“I’ll get these, Amy,” Jessica interjected, stepping forward with her card ready. She tapped the card against the reader, and the barista turned to prepare the coffees.

Free from questions, Scott turned to glance around the room, feeling like a deer caught in headlights. Never before had he experienced such awkwardness. Jessica leaned in, whispering, “Posture. Breathe. You’re fine.”

(See image 08)

But fine was the last thing Scott felt. The soft material of his clothing hung and clung to his body in unfamiliar ways, and his feet ached in the high heels. Time seemed to stretch on forever as he waited for the barista to prepare their drinks, shifting uneasily on his heels, longing to be anywhere else.

At last, the barista set down two cups on the counter, calling out “Amy.” Scott stepped forward to collect them, embodying the role he had been thrust into. He was Amy at that moment, dressed in her clothes, wearing her shoes, his face covered in her makeup. He managed a nervous smile as he took the coffees, realizing only then that he had forgotten to ask for them to go.

Jessica, seemingly able to read his mind, stepped closer. “Looks like we’re having our coffee here,” she said with a light, encouraging tone. “See, that wasn’t so hard, was it? You did it!” she added, her smile aimed reassuringly at Scott.

Scott knew she was right, but a part of him wished she wasn’t. Deep down, he had harboured a hope that the barista would see through his disguise, a secret longing for affirmation of his masculinity.

“Let’s grab that sofa over there,” Jessica suggested, pointing towards a cosy corner with the tip of her long, manicured finger. “We can discuss travel plans for tomorrow.”

Watching Jessica stride confidently ahead, Scott felt the full weight of the moment. This was real. He was about to step quite literally into Amy's shoes to attend the meeting in her place!