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Chapter 20
by Mr Nice Guy
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Brushed, Blushed, and Brainwashed
Isabelle didn't need an alarm anymore. Riley's soft humming from the bathroom always woke her before sunrise. She padded quietly to the doorway, mug of lemon water in hand, and watched her pretty boy begin his routine. It had been a couple months since she started making changes in Riley's life, a couple months since she had decided that she had had enough of his toxic masculinity nonsense, and while she had the experience and know-how to make the changes she wanted, but Isabelle had no idea how effective they'd end up being. It was far better than she could have imagined. Every morning was its own little triumph.
There he was, her beautiful bimbo-in-the-making.
Riley stood at the mirror in his cloud-blue camisole, brushing his long, honey-blonde hair with care. He always kept his strokes even, his elbows in, his movements so gentle and practiced. Isabelle could hardly believe this was the same boy who once lived in ratty jeans and hoodies and didn't even own a hairbrush. Off to the side, on the vanity countertop, his phone was quietly playing a video of a makeup tutorial. She suspected that he no longer needed the coaching, but that they were a source of comfort to him.
He turned slightly, checking his side profile. The push-up falsies Isabelle had glued into the lacy pink bra made his chest look irresistibly full under the cami. In truth, he was starting to grow his own—tender little buds from the hormones, enough that he winced when hugged too hard. But he barely registered the change, at least not in the way a young man normally would. Instead, he had seemed excited, thinking that he was seeing his chest growing, becoming more manly by the day.
That's perfect, Isabelle thought, sipping her drink. He'll be ready when they come in for real. Let him think what he wants, it won't change what's coming for him.
Riley moved on to his skincare. Toner. Serum. Moisturizer. His face was glowing. Feminine. Rounder in the cheeks now. Softer jawline. Lashes dark and long. He was barely recognizable as the old, masculine Riley. Only someone who stared, really stared, could notice. To everyone else, he was a young woman, nothing more.
After his pills—Isabelle made sure he took them at the same time each morning—they had breakfast. Acai bowls with granola. Riley, as always, sat with one knee folded over the other, scrolling through his socials and giggling when someone commented fire emojis under his latest #OOTD.
"You seem to be trending with a certain demographic," Isabelle teased lightly, looking over his shoulder and seeing all the comments from men on Riley's feed.
Riley smiled, biting his lip. "They're just being sweet."
They're being thirsty, Isabelle thought, but didn't say it. It was better to let Riley think what he needed to. If she confronted him too early with truths he wasn't expecting, it might shake loose some of his programming, undoing some of her hard work.
After breakfast, it was time for meditation. Isabelle had texted Riley some pictures of Chase she had sneakily taken at the gym, which he quickly excused himself to the bathroom to appreciate. She'd noticed that he had cleaned his egg that morning, and that he stopped by the towel that it had been drying on to take it with him.
Perfect, she thought. It's time for a new track.
She scrambled up to his computer to upload the new subliminal track. This one was special.
Kissing is a way of being close, a way of learning his needs. You want to learn Chase's needs. You want to kiss him. Kissing is something girlfriends do with their boyfriends. You worry about doing it wrong. If Isabelle allows it, you can practice with her. But it won't feel good unless you imagine that it's Chase that you're kissing. Kissing Isabelle is weird. She's your ex. The idea of kissing girls is weird, and would remind you of kissing your ex. Kissing Chase helps you understand his needs.
The file uploaded without a sound. Though there was no way to detect it, Isabelle knew the message was already broadcasting from Riley's pillow, his headphones, and his computer speakers. She tiptoed out of the room, past the washroom where she could hear the quiet vibration of Riley's egg, and smiled. Soon her new messages would begin to sink deep, like a sugar cube dissolving in tea.
Then it was gym time.
Riley changed into his black leggings with the contour stitching on the rear—ones Isabelle had bought and told him that he looked darling in. The sports bra, combined with his breast forms, gave him an extremely top-heavy look, with cleavage begging to escape out of the top. And the cropped tank he wore overtop left his flat, hairless stomach on display.
At the gym, Isabelle stayed back, watching him from the elliptical. He had developed such a natural swing to his hips. His ponytail bounced in rhythm. He glided from machine to machine, always careful not to sweat too much—just enough to get a glow.
And then he saw him.
Chase Donovan.
Isabelle spotted the moment Riley did. His jaw slackened, his lashes fluttered, and he unconsciously smoothed his top. He stared openly as Chase moved through his reps, every muscle rippling under a sheen of sweat. Riley wasn't just noticing men anymore—his eyes were drawn specifically to Chase.
Then, to Isabelle's delight, Riley walked over.
He paused just beside the bench where Chase was curling, then leaned down just enough to give him a view. His voice was soft, shy. "Hey," he said.
Isabelle couldn't hear what Chase said back, but she saw his eyes flick over Riley's chest, his grin slow and interested. Riley twirled a strand of hair, bit his lip. He giggled. Actually giggle-giggled.
Flirting.
Isabelle clutched the edge of the machine to keep herself from squealing. The little minx was doing it.
After a few more exchanges, Riley walked back, cheeks glowing, hips a little looser.
"What was that about?" Isabelle teased as they left.
"I just... wanted to say hi," Riley said too quickly, then added, "He's, like, really ripped. I told him he looks great."
Isabelle leaned close. "He thinks the same about you."
Riley looked away but smiled. "You think?"
"You should have seen him stare at your ass as you walked away. Those leggings are doing their job. You look absolutely hot, girlie-girl."
Back at home, Riley showered and moisturized while Isabelle reviewed his post-workout selfies. The lighting was perfect. He looked dreamy with the sweat-sheen and the crop top pulled off one shoulder.
"Caption this one," Isabelle said, handing him the phone.
Riley typed: Post-gym glow - working hard to be my best self!
He posted without hesitation.
Later, as Riley slipped off to the washroom for another evening meditation, Isabelle watched him leave with quiet pride.
Her boy was coming along beautifully. She still had plans, such big plans, for her ex-boyfriend. Soon enough Riley would be practically throwing himself at Chase.
It would be her job to get him ready for that day.
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Crossdressing Stories
A collection of separate stories that all involve guys ending up in dresses
A collection of separate stories that all involve guys ending up in a dresses
- Tags
- Hypnosis, Misunderstanding, Crossdress, Halloween, Bet, Dare, Crossdressing, hormones, feminization, sissy, housewife, Stepford, Stepford wife, hucow, Maid, Fetish, Femdom, Thigh-highs, mistaken identity, mind control, manipulation, Accidental, Mr Handy, Vault, Fallout, Magical Crossdressing, Leather, Princess, Secretary, Fantasy, pokemon, Mindcontrol
Updated on Jun 19, 2025
by ShimoDragon
Created on Feb 1, 2018
by Dayeandknight
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