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Ashley Tyler’s Guide to Self-Confidence - Part 3
🕑 Added 2025-07-17 03:20:18 +0000 UTCPart 3 - All Together Now
By 9 PM, he was standing in front of a neon-lit entrance, heart racing, hands stuffed into the pockets of his jeans. He hadn’t been to a club before. He hadn’t even considered going to one. Too many potential social disasters all in one place, and that was before you mix alcohol in.
“Caleb!”
The voice carried over the thumping bass outside and he looked up to see Tracey standing with a small group of women by the door, waving. They were all in mini dresses, with glossy lips, and glittering heels. He faltered and looked down at his jeans and plain black shirt, instantly feeling under dressed. Maybe he should just leave.
“There you are!” Tracey’s voice cut through his spiral. She waved him over, grabbed his hand, and pulled him toward the group before he could protest. The music was so loud that he could barely understand her as she introduced her friends. No one looked at him funny. No one made a face about his outfit. Still, he felt like he stuck out in all the wrong ways.
“What do you drink?” one of the women asked, Sasha, maybe?
“Uh,” he said. He didn’t know. A man would just say beer. That was the safe bet, but what was the common woman's drink? He had no idea.
“Cosmo it is,” Tracey said with a wink, ordering for him before he could decline.
The cocktail was pink, sweet, and surprisingly strong. He sipped it slowly, half-listening as they chatted around him. But the volume made it hard to follow anything for long, and the swirl of strangers made his anxiety bloom like wildfire. They were all so pretty and relaxed around each other. He barely knew how to socialise as a man, what had he been thinking? Then Tracey grabbed his hand again.
“Come on. We’re dancing.”
“I don’t really-”
“You don’t have to know how. Just come.”
He stumbled onto the dance floor, stiff and uncertain, acutely aware of every movement he made and how new his body still felt. The music pulsed through his chest, but his body refused to follow the rhythm. He stood awkwardly, occasionally swaying, desperately trying not to look like a complete idiot.
He waited for eyerolls, but the girls didn’t care. They danced around him, encouraging him with smiles and laughter. Sasha twirled him. Another girl, Bree, shouted over the music:
“You’re doing great!” even though he clearly wasn’t.
Little by little, he let go. The cosmo helped. So did the genuine joy on their faces. It was infectious. He started moving more, stopped worrying about what he looked like. His new hips swayed more naturally and he leaned into it, letting his but bounce a little. Tracey whooped when he spun himself in a little circle, arms up above his head. The music thumped louder, faster, and suddenly he was dancing.
His heart seemed to keep pace with the beat of the music; fast and excited. And then there was something else. With each beat of his heart, he felt his chest growing heavier. Caleb looked down and watched as his shirt transformed before his eyes into a cute black singlet. A pair of perky breasts slowly growing to fill the space. In a panic he looked around, but nobody else semed to notice.
“I forgot to say I love your top!” Bree yelled over the music, “So cute!”
“Thanks!”
He didn't know what else to say. This confirmed it, nobody but him seemed aware of any changes. As far as these women were concerned, he came into this club rocking a sweet rack and a singlet top. Speaking of his new curves, he could really feel them bouncing now. Each turn of his body seemed to make them move differently. It made dancing almost intoxicating. Caleb started to experiment, twisting this way and that just to see how different it could feel.
Tracey grabbed his hands and they danced together before she spun away, giggling. He laughed, for the first time in what felt like years. The night blurred into a haze of colour, motion, and laughter. For the first time he could remember, Caleb forgot to be nervous.
The music had just shifted into something slower and smokier when Tracey shouted in his ear.
“Bathroom break!”
Caleb briefly flashed back to high school and how women would go to the bathroom together in droves. Apparently, that stayed in adulthood, a fact he tucked away for later. The bathroom was a chaos; women swarmed the mirrors to fix their make up and line up outside the stalls. In the corner one group was trying to fix a broken heel while the poor woman drunkenly balanced on one foot.
It felt so wrong to be in here. Like at any second, one of the women would turn, see him and yell ‘perv!’. Security would come and throw him out, and he’d forever be branded at work as that weird guy who walked into women’s bathrooms. That didn’t happen, though. The ladies gave him half-drunk smiles, and one of Tracey’s friends, Natalie, threw an arm around his shoulder.
“You look like you’re about to combust. Breathe.”
“Heh, sorry, too much dancing.”
“No such thing!”
He watched in fascinated confusion as one of the other women, Sasha, pouted at her reflection.
“I’m all smudged, what would hide it best?”
“Smudged is sexy,” Bree chimed in. “Like you’ve been dancing all night.”
“I have been dancing all night,” Sasha said, mock-serious.
Then, unexpectedly, Sasha turned to him.
“Hey. What do you think?”
He blinked.
“Uh… smudged?”
Sasha grinned.
“See? She gets it.”
She. It was such a simple word, said so casually, and yet it hit like a ton of bricks. Once again, he glanced at himself in the mirror; after years of avoiding his own reflection, it felt strange to study himself so intensely for the third time in as many days. A woman stared back, his hair was still brown and shaggy, but the roots were starting to turn a soft blonde. His features were delicate, his curves obvious; nobody would ever mistake him for a man. There was even a layer of slightly smudged gloss on his lips and streaks in foundation he hadn't put on from sweat. Tracey passed him a makeup wipe from her purse.
“You’re sweating like you just ran a marathon.”
“Feels like it,” he admitted, wiping his forehead. “How do you all look like you stepped out of a magazine?”
“Practice,” Bree said.
“And setting spray,” Natalie added, holding up a tiny pink bottle like it was a magic potion.
They helped him fix his makeup, and then it was back out the door. The air was cooler and clearer somehow. His head still buzzed, but now it was with something softer than nerves, something close to happiness. And when Sasha linked her arm through his on the way back to the dance floor, he didn’t hesitate.
By the time they stumbled out of the club sometime past two, the streets were mostly empty, slick with the sheen of recent rain. A cab splashed past them, and Tracey shrieked with laughter as a few droplets caught her ankle. Her heels dangled from one hand, her other arm draped casually over his shoulder for balance.
He didn’t mind. In fact, it surprised him how natural it felt, her weight against him, her laugh in his ear, the way the night had chipped away at his walls without him realising. They drunkenly waved goodbye to the other girls and started down the road. Caleb’s shoes had transformed into a pair of strappy heels at some point during the night, and they clicked against the damp road as they walked.
“You,” Tracey said, “are not who I thought you were.”
He blinked at her, still breathless from dancing.
“What do you mean?”
“I dunno. You were always so… still. Like background music. But tonight? You were kinda electric.”
“That might’ve been the Cosmo.” He laughed sheepishly.
“Nope,” she said. “It's all you.”
All him. That felt…nice to hear.
“This is me,” Tracey said all of a sudden, and her arm slipped out from his, and she indicated to the apartment block behind them.
“Oh, right. Thanks for inviting me.”
“Thanks for coming! I am glad you’re getting out of your shell!”
There was a brief pause. In all the movies, this would be where the guy kissed the woman. But he wasn't a guy anymore. So that couldn’t be what she was waiting for, right? Was there some sort of secret woman only goodbye that all ladies knew? Like the bathroom rule or how to do that thing with towels around their heads?
“Well, goodnight.” Tracey smiled, “See you at work Monday.”
“Yeah, bye.”
Caleb watched her go, then immediately realised how creepy that probably looked and kept walking, maybe a little too fast, home. The energy had suddenly shifted, and his whole body felt hot, not in the club way, but a more familiar combination of embarrassment and arousal. It was so like him to develop a crush on the first lady to be nice to him forever. How pathetic. The only reason she was even hanging out with him was because he was a woman now.
“No, that’s not true,” said a little voice in his head that sounded suspiciously like Ashley Tyler. “You’ve been putting yourself out there, growing, that’s why she wanted to hang out with you. Maybe more.”
Caleb shook his head at the last part. There was no way. Women were just like that, tactile, friendly with each other. He was reading way too much into it. When he got home, his feet were aching from the heels, and he still felt a little embarrassed about how it ended, but he couldn’t regret the night.
~
Days went by and Caleb still had no idea what could be causing his strange change. It wasn’t just him either; it was his clothes, even his home. He opened his drawer to find lipsticks and sports bras, his old jeans and shorts had been replaced with skirts and dresses. Even his work outfits had become sharp pencil skirts and stockings. His hair had even grown out to brush his shoulders and turned a shiny white blonde.
It took him a while to get used to putting on a bra each morning, but he quickly learned going without wasn’t an option. Not unless he wanted a sort back and his nipples on full display. Caleb knew on some level he should have been bothered but honestly; his life had never been better.
Thanks to Ashley Tyler's courses, he was learning how to be the best woman possible. Her lesson on dressing for success had really helped him learn to navigate his transformed wardrobe. He even got compliments from strangers at the shops sometimes. And instead of getting flustered, he’d smile confidently and say thank you. It was like the world had become friendly. Something had finally clicked in his brain and navigating it felt less and less scary.
With one exception.
Tracey. She still made his heart thump every time they ate lunch together. The way she’d elbow him with a teasing smile as they talked made his palms sweat. He was a woman now, he couldn't go flirting with another woman! Especially when she was his first real friend. Dustin and Steve were too, he supposed, but Tracey felt different. There was a kinship he wasn’t sure how to navigate.
So he ignored it. Pushed those feelings so deep down he didn't have to think about them and focused on the here and now. Like tonight, Tracey and he were going out with Bree to a new cocktail bar. He slipped into tight-fitting white mini dress and matching heels with a smile. Showing skin felt empowering thanks to Ashley Tyler, not scary. His choice was instantly vindicated when he walked into the new bar, and Bree squealed.
“Oh. Em. Gee. Caleb, you look incredible!”
“Thank you! It’s new.”
“You’ll stop traffic. Doesn't she look fire, Tracey?”
Tracey suddenly became enamoured with her drink and drained the whole thing before letting out a strained gasp as she forced it down.
“Great! You look great!” She choked.
“Well, so do you,” Caleb replied, remembering Ashley Tyler’s advice of repaying compliments. “That skirt really shows off your legs.”
It was true. Tracey was in a short, black skirt with a red heart shaped top. Caleb suddenly wished he had a drink as well to hide him swallowing nervously. Instead he picked up the menu and looked it over.
“So, what should we order?”
Three hours and twice as many cocktails later, the three of them were laughing. The drinks here were incredible, some even came on fire, much to Bree’s delight. She finished another and put it down before jumping to her feet.
“I’ll get us another round!”
Caleb groaned.
“Is she trying to give us alcohol poisoning?”
“No,” Tracey chuckled, “She just wants an excuse to flirt with the bartender. See?”
He looked over to see Bree half off the ground, leaning on the bar top and curling a finger around her hair as the bartender took his sweet time with her order. It was obvious they were into each other.
“Maybe we should leave her to it?” Caleb suggested.
“And go where?”
“My place isn’t far.”
The words slipped out before he could think, damn those fruity drinks. But to his surprise, Tracey nodded, downing the last of her own cocktail.
“That sounds good, I don’t really want to drink more as it is. These heels are dangerous enough.”
They stumbled to their feet, giggling as they made for the door, only for a shape to block their path.
“Hey ladies, you’re looking a bit unsteady there. Want me to help you get home?”
The man was dark-haired and tall, about as tall as Caleb used to be. He hadn't even noticed losing a few inches of height until now. Tracey shook her head and tried to shift past.
“No, we’re fine.”
“Woah, woah, hey hold on a minute.”
He stepped up to block their path again, and Caleb swallowed. All of a sudden, the world didn't seem so friendly anymore.
“I know the game, you’re playing hard to get well, let’s cut to the chase, shall we?”
“Sure,” Tracey said, narrowing her eyes. “You’re acting like a creep, let us pass.”
“What about you, sweetheart?” He turned his attention to Caleb. “You like a guy who’s forward, don’t you? Wanna ditch your frigid friend and come home with me?”
Caleb felt like a deer in the headlights; he had no idea what to say in this situation, except maybe the truth.
“I’d rather get flattened by a steamroller.”
Tracey gave a bark of laughter at the man’s shocked face before grabbing Caleb’s hand and quickly walking around him and out the door.
“Hey!”
The man turned and grabbed Caleb’s wrist. He froze, momentarily froen when suddenly, Tracey’s fist blurred past. She slammed a punch into the mans face so hard that his hand let go and he went sprawling to the floor. Tracey grinned, rubbing her knuckles slightly and grinning at the other bar patrons, including Bree.
“Try that again and it’ll be your dick.”
Snickers and whispers started to echo around the room and the man’s face went bright red. Caleb felt his heart pounding in his chest watching Tracey standing over him like an absolute badass. No wonder she did well in security.
“Men never think women can knock them senseless.” She shrugged, “One of the few advantages to my position. Come on, Caleb, let’s go.”
She turned on her heels and grabbed his hand. Caleb’s eyes lingered on the man for a moment, watching as he sheepishly dragged himself up and tried to hide the red mark spreading across his cheek.
“Your loss!” He yelled as the door slammed closed, and the pair of them giggled.
“He is right about one thing.” Tracey said, “We’re probably a little too drunk to be walking home.”
“Cab?”
“Cab.”
~
By the time they’d flagged a car down and stumbled their way to Caleb’s apartment, the alcohol was starting to wind down, and they were both closer to tipsy than blind drunk.
“Sorry for the mess.” Caleb blushed, “I wasn't expecting company.”
“No judgment here, my place looks like a bomb went off,” Tracey replied, flopping down on the couch. “So, what should we do?”
“...I uh, didn’t think that far ahead.”
Tracey didn’t seem bothered; she just shrugged and patted the couch where she was sitting.
“That’s fine, we can just chat. I always worry you must be lonely down there doing data analysis all on your own.”
“Hm, it didn't used to be,” Caleb admitted. “The truth is, I loved being away from everybody. Less chances to embarrass myself. I’m…sort of awkward.”
“So? I’ll admit, you can be a little jumpy from time to time but you’re not that awkward at all, and you stood up to that asshole no problem.”
“Yeah, I did, didn’t I?”
Caleb’s back straightened a little in pride; it had just been a single line, but it had been direct, he hadn’t stuttered at all. Actually, now that he thought about it, he hadn't been stuttering much lately.
“Hey, what’s this?”
The blood drained from Caleb’s face only to immediately rush back into his cheeks as Tracey held up a familiar CD with Ashley Tyler’s face splashed across it. One of her pieces of advice echoed in his mind.
“Remember, the truth will set you free. Don’t hide parts of yourself away!”
“It’s an advice course,” He admitted, “you know, learning how to build self-confidence and all that. I’ve been working my way through it, I’m almost done as well!”
“Hey, good for you. Is that why you started holding yourself differently?”
“Yeah…”
“Hey! I am proud of you, not many people want to admit they need help, or go searching it out. Is this any good?”
“Yeah, actually, she’s been really helpful.”
“Well, if this lady is why you started to come out of your shell and joined us for lunch, I should thank her.”
“You like my company that much?”
“Of course!”
Caleb suddenly realised just how close they were sitting, their thighs were pressed together and their hands were basically on top of one another. All of a sudden the flush in his cheeks was for a whole other reason.
“It’s pretty late.” He said finally, “Did you want to spend the night?”
“That depends.”
She leaned in close enough that he could feel the heat from her breath.
“Would I be staying on the couch, or in your bed?”
No amount of self-doubt could convince Caleb she wasn't interested now. He licked his lips, feeling their softness and was suddenly overwhelmed with the urge to feel Tracey’s against them. He cleared his throat.
“I think the real question is, will we make it to the bed?”
That was all the permission Tracey needed to press forward and capture Caleb’s lips in her own. Softness against softness, it felt better than any kiss he’d ever had as a man. He reached out and pulled Tracey onto his lap, letting his hands roam up and down her sides, feeling the beautiful hourglass shape. Her curves weren't as big as his, but they were lovely, and the way she shivered under her touch made him wet between his legs.
He had been so busy trying to fit in that he hadn't even experimented with his new body that much. At the end of each day, Caleb had just fallen into bed exhausted. Now, his whole body felt alive. Arousal tingled at his skin, and heat gathered between his legs. It was so different from being turned on as a guy; it was exhilarating.
Tracey’s hands found the edge of his tight mini dress and pulled it down around his middle, exposing his breasts fully. She leaned back for a moment, admiring them as she ran her fingers over the sensitive skin.
“These are even better than I’d imagined.” She whispered. “I wonder how they taste.”
That was all the warning he got before her mouth moved down to claim one of his new nipples. Caleb saw stars. Her tongue traced circles around the diamond-hard numb before licking and pressing at it, making his back arch against the couch. Tracey cupped both his breasts, massaging the skin while she suckled before finally pressing her teeth lightly to the skin and letting go.
“Amazing.” She teased.
“Hm, what?” Caleb’s brain felt like mush after that.
“That’s how they taste.”
Tracey giggled and quickly took off her own shirt and bra.
“Wanna try?”
Caleb had never wanted anything more. Gently, he cupped her breasts in his hands, squeezing gently and watching her face to see what felt best. Her hips rocked on his lap, and Caleb could feel a heat, very similar to his own, between his legs. He reached beneath that short skirt and felt the dampness soaking into her panties.
“I’m not very experienced at this,” he admitted, but Tracey just moaned.
“That’s okay, I’m patient and a good teacher.”
He pulled her panties aside and began to stroke, up and down. More wetness coated his fingers, and she gasped, rocking her hips until his fingers naturally slipped inside. Her passage clenched around his fingers before she slowly began to rise and fall. Caleb watched her face, taking in every twitch and gasp and committing it to memory. He thrust his fingers in deeper until they curled against something that made Tracey moan.
Caleb grinned and did it again, with each thrust of his fingers, he made sure to press against that same spot. Soon Tracey was bouncing up and down on his lap, fucking his fingers until finally her whole body went tense, she came with a shaky gasp and collapsed down against him, breast to breast.
“For somebody without much experience, you’re pretty good at that.”
She pulled back and smiled for a moment, tucking a strand of Caleb’s long blonde hair behind his ear before kissing him deeply. Her tongue danced against his for a moment before she pulled away once more and gave him a grin. Caleb watched as she slowly dismounted and got to the floor, pushing herself between his knees. Without a word, Caleb lifted his hips and pulled off his dress and panties before settling back, now fully naked save for his heels.
Tracey didn’t hesiotate, she dove between his legs, pressing her mouth to his pussy and kissing it just as passionatly as she had his mouth. Caleb reached over his shoulder and gripped the couch tightly, back arching and hips rocking into Tracey’s mouth. He didn't have words to describe how good it felt to have her tongue circling his clit, then pushing into his passage. No blow job could compare.
It didn’t take long for Caleb to be overwhelmed. His hips rocked against Tracey’s mouth as his fingers buried into her hair. The other hand was still gripping the back of the couch as he got closer and closer to the edge until finally everything crashed down over him at once. The orgasm seemed to last forever, filling his entire body and making his toes curl.
Tracey continued to lick gently against his clit, sending aftershcoks all through his body until finally, she showed mercy and Caleb collapsed back into the couch; sated and exhausted. Tracey crawled back up his body, straddling his lap with a cheeky grin and a glint in her eye.
“You look proud of yourself,” he chuckled.
“I think I should.”
“Damn right that was…amazing.”
“You didn’t last long.” She teased.
“It’s been a while.”
“No judgment here, darling, for a while I was worried you might not be…interested in me. I was putting down so many hints. I’m glad to see you’re just thick skulled.”
“...I didn't realise post sex chats involved so many insults these days.”
Tracey just giggled and kissed him again. He could taste himself on her lips, somehow, it was the hottest thing he’d ever experienced. A clattering sound made them both jump, and Caleb realised in their shifting the CD had fallen tot he floor. Tracey grinned down at it and blew a kiss.
“Thank you, Ashley, for bringing this lovely lady into my life.”
She was only joking, but Caleb thought it genuinely. Life had never been better. Tracey’s fingers laced through his, and they left the couch, abandoning their clothes as they made their way to the bedroom. The realisation was slow and quiet as they walked. Caleb could feel his hips swaying, he could feel his breasts moving, and his nipples pebbling in the cool air.
He liked it. He had planned to fit in as a woman for as long as possible, but now, the desire to actually find a way back to his old body was gone entirely. Honestly, it hadn’t been strong to begin with.
Tracey settled down in his bed and held out an arm. He snuggled in next to her, breast to breast and took a deep breath. No. He wouldn't be looking for a way back, not now. Not when life was so perfect.
~
Tracey was asleep when he opened his eyes the next morning. Her hair was all over her face and her mouth was slightly open. She looked adorable. Caleb could still hardly believe last night had happened. His head pounded slightly, all those cocktails had to catch up to him eventually he supposed.
Quietly as he could manage, he slipped from the bed and tiptoed across the room to the bathroom and collected a pack of headache pills. Judging by how soundly she was sleeping, Tracey wouldn’t be up for a while, he’d pop a few of those and then when his headache was sorted, he could make them both breakfast.
He was just crossing the living room to get a glass of water when his foot caught on something, making him stumble. Luckily, he caught himself, but the pill in his hand went tumbling to the floor.
“Damn it.”
It felt awkward, being on his hands and knees like this. He probably should have grabbed a dressing gown or something so he wasn’t totally naked. He spotted the pill under the couch easily enough, but then something else caught his eye. A familiar, smiling face on a piece of thin card: Ashley Tyler.
“What’s this? It must have fallen out of the CD when I first opened it.”
He turned the card over in his hands, expecting the usual legal jargon but instead; there was a word in big, bold lettering right across the top: WARNING.
“This course is designed for women, and women only. The special, influential infrasound I have placed as a backing to these courses may have unforeseen side effects for any man who listens.
Fret not! If you are a man and have accidentally been exposed to these sounds, there is a cure! So long as you do not finish the course, your body and reality will return to normal within a month. Just hold tight! If you have already finished the course, and still want your male body back, please call the number at the bottom of this card and one of my magic-tech assistants will be in contact to see if there is anything we can do!”
Caleb stared at the message for a long while, soaking it in. It was so obvious, now that he thought about it. Of course, it was the audio course transforming him. And he hadn't finished it yet, there was still one final lesson to go. So all he had to do was throw away the CD and wait and he’d return to normal.
Caleb got to his feet and swallowed the headache pill before striding confidently over to the bin and dropping the card in without hesitation. He had no use for it. Instead, he grabbed his headphones and settled himself back on the couch. For a moment, he closed his eyes and remembered the night before with a smile on his face before pressing play.
“Hey, beautiful! We’re finally here! The final lesson!”
Ashley Tyler’s voice was as bubbly as ever, and those same rhythmic sounds sent waves of relaxation through his body.
“The truth is…I don’t have anything left to teach you! If you have been following my advice, you have been finding your inner strength as a woman, and that’s all you really need, darling. You can walk the walk, talk the talk and hey, probably even talk the walk if you wanted to! Hehe!”
“You’re your own woman. Now, does that mean you don’t have problems? Does that mean you’ll never feel anxiety again? Of course not, life is hard, beautiful, but you don't need me to tell you that. All I will say is this. You’re strong, you’re beautiful, inside and out, and you can make it through anything. Just remember: be kind, be strong and never give up. Okay? Can you do that for me?”
Caleb smiled and answered, despite the fact that he knew she couldn’t hear him.
“Yeah. I can.”
“That’a girl! I have faith in you! And importantly, you have faith in yourself! Go out there and take the world by storm!”
The voice echoed out, and the sounds stopped. Caleb looked down at his phone and saw the little bar had reached the end. He’d finished Ashley Tyler’s course. Nothing was going to change him back now. Or rather, her back now. The bedroom door creaked and an equally naked Tracey stepped out, stretching with a contented smile on her face.
“Morning. What are you listening to?”
“Nothing, how about some breakfast?”
“Naked breakfast? You sure know how to treat a lady. Maybe I should come here again.”
Caleb giggled and kissed her.
“I’d like that.”
