Ashley Tyler’s Guide to Self-Confidence - Part 1

Commissioned by George Washington

Got problems with anxiety and self-confidence? Fear not! Ashley Tyler’s audio course will help you work through them and become the woman you were always meant to be! Please note: men who listen may experience unforeseen side effects. 

Part 1 - Walk the Walk

The next day started like any other; he got up, had his breakfast and dressed for work. The best part about being a data analyst was that he spent all day, every workday, sitting alone in a tiny room in the basement of a skyscraper. Most people moved on quickly from such positions, dreaming of the penthouse offices and big jobs upstairs. Not Caleb, he loved his dark little hole; he was pretty sure nobody in the company even knew his name, except the payroll man. That was exactly how he liked it, or at least, it was the best way to avoid embarrassment. 

Sure it was lonely, sure it hurt when he didn't even get invited to office get togethers because nobody ever thought about the guy in the room alone downstairs but…he’d probably just make a fool of himself if he went anyway. 

Today though, he felt something different as he walked into the lobby and scanned his security pass. Most people were heading to the elevators to go upstairs tot he proper offices. He passed them by as usual, ready to go downstairs but as he did several people looked up and smiled. One even waved. Normal, everyday interactions for most people, but not for Caleb. Most of the time people didn’t even notice he was there. 

Was it…could it be the way he was walking? His shoes clicked against the tile floors as he finally arrived at the stairs and realised he’d been walking just like he’d practised back in his apartment yesterday. One foot in front of the other, hips swaying, head up. His cheeks flushed a little, realising he’d been walking like a woman, but a small part of him felt happy. People had noticed him, but in a good way! That never happened. And the only thing that had changed was how he walked? 

“I know she said it made a difference, but…I didn’t realise she meant that much for a difference.” He muttered, descending the stairs to his dark little office computer. He sat down and waited the requisite five minutes for the ancient PC to boot up. He drummed his fingers and swung his legs impatiently, listening to the ancient fan whir. Hang on, legs swinging. 

Curiously, he bent down to examine his chair; normally, his feet were flat on the floor, but today they dangled ever so slightly. Had somebody changed the height of his chair? Impossible, he didn’t have any coworkers to prank him. Maybe he did it and forgot? 

Shrugging, he adjusted it back and settled into his chair to start work. Normally, he found solace in the simplicity of math; it always worked the same way, and there were no hidden social rules to worry about. But today his mind kept wandering, specifically to his ass which felt oddly large on his seat. The chair felt too soft all of a sudden, and his cheeks hung off the sides slightly. 

“Am I getting fat or something?”

He stood and twisted himself to look down at his body. It was hard, but even at the weird angle he could tell his butt looked different. The fabric of his pants was stretched across it much tighter than usual. He half expected the cheeks to burst through the seams! His belt had been a little tighter this morning, but he hadn’t thought anything of it. 

“I can’t have gained weight that fast…” He muttered before shaking his head. 

He could worry about weird weight gain later. And yet, as the work day went on, he noticed more tiny changes. The way his pants sat was different, not just across his ass but also around his thighs, where they were tight and too loose around his claves. He also had to tie his shoe laces tighter to keep his foot from slipping around in a shoe that had been the perfect size just yesterday. 

By knock-off time, he was behind, having only gotten half his usual work done thanks to all the tiny distractions. Caleb wasn't worried though; it would be weeks of bad work before anybody noticed. 

He was halfway across the upstairs lobby when he realised his hips had taken on a familiar tilt. He was walking like a woman again. 

“Damn, one night of practise and its stuck in my brain.” He muttered and forced himself to try to walk normally. 

It felt wrong and instantly, Caleb felt a shift in the people around him. There were no more friendly smiles, nobody moved out of the way as he exited onto the footpath, he was ducking and weaving through the crowd like always instead of it parting for him. And with every step his hips felt stiff, like they were moving wrong. 

“Maybe this Ashley Tyler girl actually does know a thing or two.” He muttered, the momentary thought being enough to distract him and set his legs going again. 

Just like that, the world became friendly again as his back straightened and he shook his head in disbelief. It really was that simple. What else did Ashley Tyler have to offer?

~

Caleb settled down on the couch with his earbuds in and closed his eyes. The same upbeat music started up, along with strange pulses that made him relaxed and a little dizzy. 

“Hello, beautiful! It’s me, Ashley Tyler, ready to help you transform into the woman you were always meant to be! I hope you’ve been having a good day so far, and if not, well, it’s okay, because I am here to make it better!”

A soft smile spread across Caleb’s lips; it felt nice hearing somebody say that. It was nice having a warm, supportive voice to come home to even if it wasn’t a real person. 

“Today we are talking about how your body can make you confident! You’ve already seen how just walking can make you stronger, now its time to change how you see yourself and how others see you!”

“A lot of women are ashamed of their bodies; they only see the flaws. Now, you probably expect me to say, you’re perfect, but guess what? You’re not…and that’s okay! So you have some freckles, maybe a bit of chub, or perhaps some nasty scars you want to hide away. I’m here to say stop! Those freckles are beautiful stars on your skin, that chub makes you curvy, those scars mean you survived something bad and came away stronger!” 

Caleb thought about himself; he’d never been very buff. He wasn’t fat or anything, but nobody would look twice at him on a beach or gym. Maybe Ashley Tyler was right, maybe it was all in his head. She continued talking, and Caleb ran his hands over his forearms; he’d always been self-conscious of how hairy they were. It was one of the reasons he always wore long sleeves. To avoid the inevitable ‘monkey man’ comment, he felt sure would come his way. As he touched them now, though, he felt that shame faded away. He opened his eyes and rolled the sleeves up to really look and found…less hair. 

His arms looked much thinner than he remembered, and the thick hair wasn’t thick at all; it was barely present! Had it been so long that he’d forgotten what his own body looked like? 

“Find strength in flaws, find strength and beauty in the small details you ignore. Don't focus on the negatives, but the positives; let them overwhelm you. Look at the beauty of your smile, the brightness of your eyes. That’s the trick to a good smile, ladies, it’s all in the eyes. If you force it, people will know. Think of something that makes you happy, and let that guide you. Let your body find strength from within! Put your feminine energy out there, and others will feel it!”

~

Caleb strode into work, head high, hips swaying and a smile on his face. He was wearing a simple button up shirt, his arms fully on display and for the first time in years, his heart wasn’t thumping. He felt confident; he didn't even care that the sway of his hips was more feminine. 

“Morning, Caleb.” The security guard smiled as he swiped his pas. “Looking good!”

Caleb felt his jaw drop, but he quickly recovered. 

“You…know my name?”

“Of course! You’ve been working here for seven years!” the guard laughed. “You normally duck past so quickly that I don’t have time to say hi!”

Caleb’s cheeks dusted pink; he had no idea. He was learning a lot lately. 

“You should come up to the cafeteria and eat with us on break, me and the other security folk always feel bad you’re stuck in that basement all alone.”

His first instinct was to shake his head and turn the offer down but then he paused; why? Why not take a chance? This guard seemed nice enough and apparently Caleb had been snubbing him for years. 

“Sure, that sounds great!”

“Sweet, see you at twelve! Wait till the others see I got you out of your cave, eh? I’ll be an office hero!”

The teasing made Caleb’s stomach do a flip. The nervous voices in his skull were already whispering, but Ashley Tyler’s peppy voice drowned them out. This guy wasn’t being mean; he was just having a laugh with Caleb, not at him. Still, he had to remind himself of that the entire morning until he walked into the cafeteria, white-knuckling his tray with anxiety. He hadn’t even asked the security guard's name, how dumb was that?

“Caleb! Over here!”

The familiar face smiled at him and waved him over to a table where several other employees, most of whom were in security uniforms, sat. Caleb took a deep breath and walked over, making sure to keep himself poised. One of the security guards wolf-whistled playfully, and Caleb swallowed. Was that a good or bad thing? He didn't know. Oh God, was this all some elaborate prank? He couldn’t turn away now, though!

“Caleb! You finally came out of the dungeon!” One of them grinned; his name tag read ‘Steve’. “When Dustin told us, I didn’t believe it.”

“Don't be an ass,” The only woman at the table scolded before turning to him with a warm smile. “I’m Tracey, don’t let these lugs scare you off, they think teasing is a form of endearment.”

“O-oh.”

This was a bad idea. Ashley Tyler had taught him how to walk, but he still had no idea how to interact with people. He squirmed slightly on his too plump ass and curled his toes, trying to burn the nervous energy. At least he had room in his shoes now, thanks to his mysterious shrinking feet. 

“You’re making him nervous.” Tracvey sighed. “Sorry, Caleb. These guys aren’t the best when it comes to talking.”

“Oh, it’s okay, neither am I?”
Dustin laughed and grinned at him.

“See? Told you he was funny?”

“F-funny?”

“I figure the quiet ones are always secretly the most interesting people. I bet you have all kinds fo wild tales and fun jokes. Loud people always project everything they do, its the quiet ones you have to look out for.”

“That would explain why you’re such a bore,” Steve smirked and Dutin rolled his eyes. 

“I-I don’t know a-about that.”

Caleb felt his hands shaking, that damn stammer. He waited for a comment on it, but it never came. 

“We’ve always felt bad, you being stuck down there by yourself without even a coworker to bounce off,” Steve said instead. “But every time we thought about going down to say hi…”

“You just never seemed like you wanted company.” Dustin finished. “But lately, you’ve seemed lighter, it’s great to see!”

“And the shirt suits you.” Tracey added, “Those heavy coats always made you seem so closed off.”

“I…didn’t realise.”

All this time, he’d been warding people away to avoid embarrassment, and they thought he was standoffish instead?

“Something about your energy has changed lately.” Dustin continued, “You seem…happier.”

Ashley Tyler’s message about putting out his ‘feminine energy’ echoed in his mind, and Caleb barely held back a wince of embarrassment. Was that what they had been picking up on? 

“You’re here now, though.” Tracey smiled. “You can come have lunch with us every day if you like.” 

“But…why?” The question slipped out before he could stop himself. 

“Why? Why not?”

Tracey shrugged with a smile and sipped at her coffee. Caleb’s heart ahced a little, what he wouldn't give to have such effortless confidence. He thought about the Ashley Tyler lessons back home; they had gotten him this face and Tracey seemed to embody all the things he’d been learning. Maybe if he kept going, he could be like her. 

Lunch passed, and Caleb let out a breath; he didn’t even know he was holding when he got up and returned to his office. He felt exhausted, like his social battery was totally drained and it would take a year to refill. Despite that, though, part of him felt light; they had been…friendly, and it had been nice to spend time with other people. He wasn’t sure he could call them friends, but he’d never even had an acquaintance. Taking two lessons to heart and walking with a bit of wiggle in his step had already changed his life drastically; what would lesson three bring?