Ashley Tyler’s Guide to Self-Confidence - Part 2

ommissioned 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 2 - Talk the Talk

“Hey, beautiful.”

Tracey giggled as Caleb slid into the seat next to her with a confident smile. It was the sort of greeting he would never dare to use on a woman before listening to Ashley Tyler, but now, it felt as natural as breathing. He’d just finished the last one before lunch; work had been making him bored out of his mind, and it wasn't like anybody was around to hear him goofing off for fifteen minutes. 

“Such a flatterer.”

“It’s not flattery if it's true.” He said. 

“I don’t think that’s how it works.” 

It had been a week since he started having lunch with the security crew and they were becoming fast friends. With each meeting, he felt a little more relaxed around them, and the fact that the last two Ashley Tyler lessons had been about how to charm and fake confidence with words helped. He’d learned all about girl code and how to support women.

“We should be boosting each other up!” Ashley said, “Not tearing one another down. Tell your friend her lipstick is cute, make sure to mention when your coworkers wears new earrings. Women are beautiful and they should know it, especially from other women. Relying on male attention for self worth is a fast track to low self esteem.” 

“I am so glad you started joining us,” Tracey said as she nibbled at her lunch. “I love the other security boys, but it’s nice to have a change of pace.”

“No other women in security?”

“No.” She sighed, “Honestly, I get it, guys are all big and macho, whenever I have to stop somebody trying to sneak upstairs, they laugh and call me sweetheart before trying to push past.”

“And then?”

She gave him a wicked smile. 

“And then I kick them in the groin.”

Caleb winced and crossed his legs subconsciously. He was about to keep talking when he realised something felt…off. He’d never sat like this before, crossing one leg over th either wasn't exactly comfortable for most guys and yet…now it was. Dustin and Steve joined them but Caleb barely registered; he was too busy, silently freaking out about the strange absence between his legs. 

He couldn’t feel his cock or balls at all. 

And not because they’d gone numb, it was like they weren’t there at all. 

“Caleb? You okay?”

He snapped back to himself and did his best to smile.

“Yeah! Just didn’t…sleep well?”

It was a bad lie, but Steve shrugged and thankfully didn’t question anything further. Caleb gave Tracey an apologetic look as he got up.

“Sorry, beautiful, gotta go.”

The worst escaped before he could stop them, and Steve looked up.

“How come Caleb can talk like that, huh?” He joked,  “If I call Tracey beautiful, I’m a creep.”

“It’s different when it's another woman, " she said, as if it were the most obvious thing in the world and not completely wrong. 

“A-another woman?” He choked out, and Tracey raised her eyebrows.

“Yeah?”

Everybody was staring now, and Caleb felt that familiar anxiety starting to build. Not knowing what else to say, he turned on his heels and headed for the bathroom. Mutterings of ‘he shouldn’t have had the curry’ followed him from the table. Followed by a cry of pain, Tracey had kicked Steven in the shins. 

Caleb raced for the bathroom. They thought he was a woman? Did he look that feminine just from his new walk? Oh God, this was so embarrassing. How was he going to tell them the truth? He couldn’t keep hiding the fact that he was a man, right? Just for the sake of keeping his new found friends? He practically fell into the bathroom and locked the door to ensure nobody followed him before clutching at the sink for dear life.

“I don’t look that feminine…do I?”

He looked up at his reflection in the mirror; he still looked the same except…where he didn’t. For the first time in days, Caleb realised he hadn't shaved, and yet, his face was smooth, without a hint of stubble. His eyes looked a little wider, or perhaps it was just that his eyelashes had grown a bit since last he checked, and honestly, who even consciously checked their eyelashes? Honestly, his first impression was that he looked…pretty. 

Men were not supposed to look pretty. 

And yet…he looked better than he ever had. The bags and worry lines around his eyes were gone, his skin was clear, and his lips were pink and slightly full. As confusing as it was, he couldn’t hate it. He was torn between the newfound confidence the appearance gave him, and the fact that he wasn’t supposed to feel that way. 

Caleb’s eyes slowly moved down his body, focusing again on the lack in his pants. Nervously, he glanced at the locked door, and unbuckled his belt. His suspicion was right, there was nothing at all between his legs: no member, no balls, only a neat mound of hair. It was surreal, but he reached down to touch the curve there out of shock more than anything. It was warm, and slightly wet, with a distinctive slit right down the middle. 

“I’m…female?”

He blinked down at the rest of his body; the thick booty and thighs, the smaller feet, and the lack of hair on his arms. He was definitely looking a lot more feminine, but he wasn’t all the way, either. His chest was still flat, his jawline still strong and angular. He was somewhere in between, except in the main place, it counted. 

“Tracey seemed to think I was a woma,n though…they all did, and they seemed sure.”

Caleb’s brow furrowed. Something else was going on, it couldn’t just be his body. Quietly as he could, he unlocked the door and stuck his head into the corridor. After making sure the coast was clear, he booked it back to his office and booted up his employee file. One of the best parts of being in data analysis was that he had access to almost everybody’s files. Caleb quickly typed up his name and found his own. 

The name was the same, so was the date and all his employment history, but…the photo it looked wrong. The face smiling back at him through the monitor was exactly like the one he’d just seen in the mirror. That couldn't be, though; he remembered the day they took the picture and how he’d been sweating bullets the whole time. All he’d been able to think about was how stupid he was for not shaving this morning. Now his permanent file had him with a five o’clock shadow. But now, it was gone. He was so busy staring in bewilderment it took him a full two minutes to notice the only other thing that had changed. Right there under his birthday were two daming words:

Sex: Female.

Female. As in woman. As in not a man. As in…what the fuck? All at once, the confidence he’d been building thanks to the audio course came crashing down. This was it, this was why those guys were being so nice. This was all some elaborate prank. They were going to befriend him and then slowly make him think they thought he was a woman, just to see if he’d play along. 

“How could I be so stupid…wait, that makes no sense. None of them could have taken this picture, and they can’t have done this.”

He felt adrift; none of this made sense. He paced the room, hyper aware of how his hips were sashaying but unable to stop it. He could go to the doctor, but if this file said he had always been female, they might think he was some kind of nut case and send him to the loony bin. That was the last thing he needed right now. 

There was no choice; he’d simply have to ‘pass’ as a woman for now and then figure out how to fix this. The rest of the day passed with agonising slowness. Caleb found himself checking every inch of his body multiple times, even so much as a breeze across his arm from the heater made him inspect it. 

His hand went to his chest multiple times, feeling the firmness there and comparing it to the last touch; had it gotten softer? Larger? More shapley? He felt paranoid, but after his manhood had disappeared, he didn’t have much choice. He was glad when the shift finally finished and he could start walking home. He’d not made it two steps when a voice called out. 

“Hey girl!”

Caleb froze in place, then turned just as a red haired woman ran past him to greet another. They giggled and were immediately leaning in to whisper something before looping their arms together and walking off. He’d seen that sort of interaction plenty of times before but now a new, terrifying thought arose: would that be expected of him? The security group had thought he was standoffish because of his coats; what if he didn't act right as a woman and made some massive mistake? 

Caleb wanted to scream; just as his anxiety was getting under control, he found a whole new thing to feel awkward and anxious about. Ashley Tyler’s voice echoed in his mind.

“Remember, you are smart and strong and brave. If you feel overwhelmed by the world just take a moment, take a breath, then break it down. You can do this! I believe in you!”

Caleb stepped to the side and did just that. Taking a deep breath, he focused on all the nervous buzzing in his chest and imagined it leaving with the air from his lungs. He could do this. Taking a moment to think, the answer was obvious. Ashley Tyler; her advice had helped him so far, and it was all about becoming a better woman. If anybody could help him pass for female, it was her. 

~

"Let's take a deep breath," Ashley Tyler said, "In... and out... Good! Now, remember, posture is key. Confidence starts from the ground up. Stand tall, shoulders back, chin lifted. Imagine you're a queen walking into a room. How would you hold yourself? Yes, that's it."

Caleb straightened, looking at his reflection with a mixture of scepticism and hope. His shoulders felt stiff, his movements unnatural, but he pushed through, following her instructions. His legs had managed to memorise this; the rest of his body could too. 

"Now," she continued, "let's work on your tone. We're going to practice speaking from your chest, not your throat. It’s a powerful tool, and it’s all about control. When you speak, imagine you’re addressing a friend, someone you trust. You don’t need to overthink it, just let the words come naturally, from a place of ease."

Caleb held back a chuckle at being told not to overthink; that was his whole thing. He took another breath, trying to focus on the sound of his voice and how he could make it more like hers.

"The trick to presenting a friendly persona is confidence. Believe in yourself first, the rest will follow. Try repeating after me: ‘I am confident, I am worthy, I am enough.’”

He repeated, but unlike Ashley Tyler, he didn't sound convincing at all. The message was simple, but somehow difficult to internalise. He paused, staring at the person in the mirror. He ran a hand through his short, dark hair, pulling at the strands absently; they were longer than usual. He needed a haircut before it got shaggy. Then again, if he was going to pass for a woman, maybe he should grow it out even if he had no idea how to handle long hair. 

He inhaled deeply and repeated the words aloud, his voice still low but stronger now than before: "I am confident. I am worthy. I am enough."

It sounded strange, like an echo of someone else, but something about it was also a little reassuring. It wasn’t perfect, but he could feel the smallest shift, like a pebble rolling down a hill, picking up speed. He kept repeating, and felt his throat tingle as his voice began to naturally go higher. The man clenched his jaw, trying to push through the tightness in his throat. His hand smoothed over his throat; no Adam’s apple. 

"Great job!" the voice in his ear exclaimed, full of enthusiasm. "Now, let’s work on your social interactions. Engaging with ease and speaking with clarity and warmth is important. You want people to hear your words, and you need to hear them. If you spend all the time worrying about what you’re going to say, people will notice. You need to engage."

“Hear other people…right. Oh, who am I kidding, this isn’t going to-hang on, is that my voice?” 

Over the course of the lesson, he'd been trying to sound more invitingly feminine and failing—at least he thought so. Now though, he wasn't even trying and his voice still had a musical lilt to it. It sounded much more womanly than when he’d actually been trying. Ashley Tyler’s voice faded intot he background as Caleb leaned in close to the mirror. 

He blinked; and his eyelashes were even longer. He gasped and his lips plumped. The changed were so slow he could only see them when he focused but it was undeniable. His face was reshaping like clay, right before his eyes. He placed a surprisingly soft fingertip to his nose and felt it shift slightly. 

“You can do this! And you can help others too! Remember, women help women! Don’t tear them down! Say yes to new opportunities and new friends!”

As if on cue, Caleb’s phone pinged. 

‘Hey! It’s Tracey, wanna come hit the club with me and some girl friends?’

Caleb stared at the message for a long time before his fingers moved, almost of their own volition, to type ‘yes’.