Disable your Ad Blocker! Thanks :)
Chapter 73
by
Mr Nice Guy
What's next?
Brave Little Girl
Riley woke up tired. Not the kind of tired that a nap or coffee could fix, but the kind that lived in the bones — the kind that felt like forgetting how to rest. He blinked up at the ceiling, trying to piece together fragments of dreams that dissolved as soon as he reached for them.
Something about changing. About losing who he was. About being remade into someone else.
That was silly, though. Of course he was changing — that was the point. Isabelle was helping him. She was always helping him. Every day she told him he was becoming more refined, more complete, more himself.
Still, when he caught sight of his reflection in the vanity mirror, something flickered in his chest. His face looked the same — flawless foundation, delicate eyeliner, a soft sheen to his lips — but behind the shimmer there was something unsteady, a hint of someone he almost recognized.
He shook it off and leaned closer, running the mascara wand carefully along his long lashes. Maybe the dreams were just stress. His numbers had been incredible lately, but with that came pressure — everyone watching, expecting perfection, expecting GirleyRiley.
He dabbed at a speck of powder and frowned. Maybe it wasn't the dream at all. Maybe it was what he'd seen on OnlyFans the other day — the other girls, the ones who had figured out that the key to success was to ride Riley's coattails. There was some real competition there, not because they were better looking or more innovative than Riley, but because their equipment was far superior! Those videos had gone viral. Their movements so effortless, so natural. He hadn't noticed a seam, or an clue as to what they were wearing and how it worked .And him? His prosthetic was… fine. Basic. It worked, for the most part, but he couldn't do the advanced techniques his competition seemed to excel at.
That must've been it. The dreams were just insecurity, bubbling up. He needed to upgrade, that was all.
He dressed quickly — a pink cropped tee, short enough to show the smooth curve of his waist; a pair of tiny white shorts that showed off his thighs; soft pastel scrunchies on his wrists. It was a little outfit that felt like armor, that told the world who he was supposed to be, that reminded him of who he really was.
Downstairs, the kitchen smelled faintly of espresso and citrus. Isabelle was already there, poised at the counter like a painting — silk robe tied neatly at the waist, long hair falling over one shoulder, one manicured hand holding a mug while the other scrolled idly through her tablet. He noticed her before she noticed him, so he paused outside of the room. She was beautiful. He remembered their time together, their long relationship. In those days he hadn't known how to treat a woman, how to be appealing to her. His whole approach to masculinity had been wrong. Without her guidance, her wisdom, and most of all her forgiveness, he would never have been able to become the man he was that day, a sexy girl who knew exactly how to use his body to please not just his boyfriend, but bring pleasure to millions of viewers around the world.

She looked up and smiled. The kind of smile that felt warm and safe, the kind that could erase any doubt.
"Morning, sweetheart," she said, voice honey-smooth. "You're up early."
Riley shrugged, index finger of his left hand playing absentmindedly with his long blonde hair. "Couldn't really sleep. I had these weird dreams. Don't even remember what they were about, really."
Isabelle tilted her head slightly — the smallest motion — and in her eyes, a flicker of curiosity. Then it was gone. Her smile returned, gentle and sympathetic. "Dreams can be strange that way. Sometimes it's just your mind catching up with all the changes you've been making."
"I guess."
He hovered by the island counter, fingers tracing the marble edge. "Actually, I wanted to talk to you about something."
Her posture shifted almost imperceptibly. The slightest forward lean, the faintest widening of her eyes — an invitation. "Of course, darling. What's on your mind?"
Riley hesitated. "I was watching some other girls' content last night. The big creators. And I noticed…" He laughed softly, embarrassed. "They're all copying my streams, which is fine, but some are doing it a little better. A lot of them have, um… better equipment than I do. I don't want you to think that I'm not grateful for the prosthetic you gave me, but, like, isnt' there something better? So I can compete?"
"Yes?" she prompted, sipping her coffee.
"Well, I was thinking that maybe I owe it to everyone. My fans, my brand. And..." his voice faltered "...and Chase. If there are girls who can give him what I can't, how am I taking care of his needs?"
For a heartbeat, Isabelle said nothing. The corners of her mouth twitched, not quite into a smile, but something close. She looked down at her coffee, hiding the satisfaction behind a veil of warmth.
When she looked back up, her expression was all sympathy. "I think that's a beautiful idea, Riley."
His eyes widened. "You do?"
"Of course! You've been such a brave little girl through everything, so committed to your transformation. You deserve to feel complete — and not just for everyone else, but for yourself."
She crossed the room, the silk of her robe whispering as she moved. Her tone was soft, nurturing, her hand resting lightly on his shoulder. "Let me make a few calls today. I'll find you the very best. It'll be exactly what you need. There might even be a surgical option, which I know you always love."
Riley's heart lifted. "Really? You'd do that for me?"
Her smile deepened. "I'd do anything for you, girlfriend. You know that."
To anyone watching, the touch would look motherly — tender, guiding. But to Isabelle, it was the act of a sculptor admiring her creation. The curve of Riley's jaw, the smoothness of his skin, the delicate vulnerability in his eyes — all of it was hers.
When she withdrew her hand, he leaned forward slightly, as though **** to break the contact.
"I'll be out most of the day," she said, grabbing her keys. "But we'll talk tonight. We'll look at options together."
"Okay." His voice was soft, grateful.
She smiled again, a perfect, practiced thing. "You're doing so well, Riley. I'm proud of you."
When she was gone, Riley stayed at the table, staring into the remains of Isabelle's coffee cup. For a while, he just listened to the quiet hum of the house, feeling oddly light — content, even.
He was doing the right thing. Of course he was.
Still, there was that strange whisper again, just behind his thoughts, something small and sharp that didn't fit.
Another step forward into what?
He shook his head, laughing under his breath. "I really need to stop watching creepy videos before bed," he muttered.
He pulled out his phone, swiping open YouTube. The cheerful voice of a makeup vlogger filled the air.
"Hey babes! Today's look is all about that glossy skin and flirty lashes!"
Riley smiled, brushing a little shimmer across his cheekbones, focusing on the sparkle, the rhythm, the routine.
Everything was fine.
It had just been a dream.
It had to be.
What's next?
- No further chapters
- Add a new chapter
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
Updated on Feb 22, 2026
by Dayeandknight
Created on Feb 1, 2018
by Dayeandknight
- 5,861 Likes
- 2,190,115 Views
- 932 Favorites
- 621 Bookmarks
- 384 Chapters
- 73 Chapters Deep
Comments moved below the chapter.
Jump to comments
Comments