Chapter 62
by
Mr Nice Guy
What's next?
Boyfriend Shopping
Riley twirled in front of the changing room mirror, the hem of his minidress fluttering dangerously high. The shimmer-pink fabric hugged his new hips and flared at the waist, riding up just enough to flash a glimpse of white lace panties. He giggled, biting his lip.
"Chase is totally going to lose his mind," he murmured to himself, admiring the way the neckline plunged into a heart shape, pushing up his tits. He bent forward, testing the cleavage, just as he tested his new word. "Yup. That's definitely gonna help him… want to fuck."
He didn't really understand the word yet. Isabelle had only explained it a couple nights ago, and they'd only done it once. The more they practiced, Riley reasoned, the more he'd understand. But the moment Chase had been inside him—fucking him—something had clicked. Something warm and delicious and necessary. Like when a cheer routine hits perfect synch or a backflip lands so smooth it feels like flying.
He wanted it again. A lot. Like, all the time.
He twirled again, watching how the heels made his legs pop, how the dress spun like a fan. "This is definitely a fuckable outfit," he said to no one, trying the word out in a new way. Then he leaned out of the dressing room and called toward the sales clerk, "Can I try this in a smaller size? I want it to really grip my waist. Like, grab it. My boyfriend loves when I look super tight."
The clerk—a college-age girl with lavender eyeshadow—blinked once, nodded, and disappeared.
Riley beamed.
In his old life, before he and Isabelle had broken up, shopping had always been a drag. But now that she'd shown him so much, explained how to be fabulous, it was totes fun! Plus now that he had the body for it—dainty hands, narrow little waist, thighs that curved out into hips like a heart—everything just looked better. And the heels? He was practically floating. Walking in flats now felt like dragging cinderblocks.
He needed Steph to know.
As he stepped back into the changing room, he made a mental note to ask her if they could add a heel to his cheer shoes. Just a few inches. Nothing too crazy—well, maybe a little crazy. It would help him move. Make the routine pop. Put on a better show for the crowd. And for Chase.
Always for Chase.
The thought made him grin as he stripped off the dress, tossing it over the door. He slipped into a denim miniskirt and a mesh crop top next—this one barely covered his chest, nipples faintly visible beneath the fabric. He looked hot. Fuckable. Perfect.
When he stepped out again, a group of girls by the accessories wall turned to stare.
"GirleyRiley?" one of them gasped. A trio of students, one of whom wore a Goldridge College shirt, all juniors by the looks of it, swarmed him instantly.
"Oh my God, you're like… famous!" one of the girls squealed. "Your videos are everywhere."
Riley grinned. "Thanks! My followers are so totally amazing. They make it easy!" He paused, posing for his reflection in a nearby mirror, sticking out his ass in a way that he knew would make Chase excited. "Want to know a secret? It's all for my boyfriend, really. He's amazing. I just wanna be the kind of girlfriend who makes him look incredible, you know?"
The girls gave each other side-eyes. Riley didn’t notice.
"Like, I don't wear stuff for me. Not anymore. Not since he and I became a thing," he continued, voice bubbly and sincere. "Now I pick what will make him want to, you know, fuck more. That's kind of the point, right?"
There was a pause. A weird, lurching silence, like a skipped heartbeat. The tall girl crossed her arms. The one with the silver nose ring raised an eyebrow.
"Wait—hold on," said the third girl, who wore a frayed denim jacket and combat boots. "You dress like that so a boy will want to sleep with you more?"
Riley blinked, tilting his head. "Well, I mean, I wouldn't exactly say sleeping. Not, at least, until we've finished fucking."
"That's kind of... backwards," the tall one said carefully. "Like, no offense, but you don't need to dress for him. You can wear whatever makes you feel powerful."
"Yeah," said Combat Boots. "I don't need to prove myself to some guy just to earn sex. I'm my own woman, and that's enough."
Riley furrowed his brow, confused. Not only did he not know what this sex thing was, but these girls totally didn't understand what he was talking about. "You think you don't have to prove yourself to a man?"
"Exactly."
He giggled, as if they'd just told a silly joke. "Oh. That's adorable."
That gave them pause.
"I mean," Riley went on, "don't you want to be the best girlfriend ever? Don't you want your boyfriend to look at you and think, 'Damn, she's perfect. I wanna fuck her right now'? Like, all the time?"
"We want to be respected," said Nose Ring, a bit stiff now. "Not objectified."
"Objectified?" Riley repeated, puzzled. "No, no, it's not like that. It's not about being some kind of object—it's about value. Without taking care of my boyfriend's needs, I'd be a terrible girlfriend. Every good girlfriend knows that. I value myself, and I value my time, and my choices. And I know that if I start ignoring my boyfriend's needs, I'm not valuing myself at all!"
Riley blew a kiss at his reflection, then bent forward and squeezed his tits, just to see what it would look like in that top. "It's about being pleasing to my man. The more I get to know him and what he needs, the more I want to please him. If I understood his needs and ignored them, I'd, like, be a failure."
They exchanged a look—amused, skeptical, almost pitying.
But something else flickered there too.
Just a flicker.
"And okay," Riley added quickly, lifting the hem of his crop top to check how high it sat on his waist, "sure, I'm not perfect. Like, he doesn't let me take care of him completely yet. He still mostly cooks for himself, and he hasn't let me do his laundry yet, but like... he's a guy. And guys are visual. They respond to curves, to color, to skin. That's just nature, right? Why not lean into that? Why not make him feel that every day is his day?"
"That's..." Tall Girl started, but her voice faltered. "That's... not how I usually think about things..."
"Well maybe it should be," Riley chirped. "Like, you could keep dressing for comfort and being all edgy for yourself, and maybe your boyfriend will still want you—but why not guarantee it? You could be his fantasy. His dream girl. Don't you wanna be that? Don't you wanna do it for him?"
The silence returned. It was heavier this time.
"I want to be taken seriously," Nose Ring said, but it came out softer, like she was reminding herself.
"Duh, me too! But being taken seriously doesn't mean being boring," Riley said. "It doesn't mean hiding the parts of you that turn him on. Like, that's part of who you are too. Your body, your lips, your little skirt—those are all tools to make him crave you. The more I put his needs first, the more I take care of him, the more I shape myself to be perfect for him, the more powerful I get. Get it?"
The other girls looked at her.
"I don't know," Tall Girl said. "I mean... I guess it is kind of hot to be wanted like that."
Riley smiled, tilting his head. "It's more than hot. It's loving. Wanting to be wanted isn't weakness—it's just honest. And making yourself extra fuckable for your boyfriend? That's romantic."
There it was again: that flicker. That subtle ripple through their posture, their gaze.
"I do have that red lace bralette at home…" murmured Combat Boots.
"You should wear it next time you see him!" Riley said brightly. "And like... lean into it. Make him need you. Let him know you belong to him. I promise, when he fucks you, you'll feel so proud."
"I'm not saying I'm changing my whole look," said Nose Ring, frowning—then adding, "but I could do something... softer. Maybe."
Tall Girl bit her lip. "If he wants to fuck me more, that doesn't make me weak. It just means I'm doing something right."
Riley clasped his hands in delight. "Wait! I have an idea! My best friend Isa told me that I'm allowed to spend whatever I want on clothes today. Why don't you girls go a little crazy in here? There's so much sexy stuff. If it would help you show your boyfriends what you're offering, I'd gladly pay for it all!"
The girls laughed, this time in disbelief. Riley could tell that his words had made an impact, that he was getting through to these girls who had been so filled with toxic ideas. He was glad he had met them, glad that he could have a positive impact on their lives.
In a moment, all three girls had split up and began eagerly grabbing clothes. At a glance, Riley could tell that they had taken his words to heart. Even Combat Boots, who went straight to the small selection of shoes near the back, was already picking out a pair of platform heels to try on.
Riley beamed, spun once more in his own heels, and glanced at the mirror again. His panties showed for again a flash, just a peek of white lace, and he didn't even care. He loved how he looked.
But, really, that didn't matter. What mattered was if Chase loved how he looked. He wanted to fuck every night. It was his dream.
The sales clerk returned to Riley, handing him the smaller size of the outfit that he'd tried on before. He thanked her and went back into the changing room. Soon he'd be with Chase. Soon he'd be able to prove his worth by taking care of his man. It was through Chase's eyes that Riley really had value. And thanks to his wisdom, these girls were now waking up to see the truth of where their value came from too.
Riley had thought of himself as a lot of things in his life, but being a mentor was a new one, and he kind of liked it.
What's next?
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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
Updated on Feb 22, 2026
by Dayeandknight
Created on Feb 1, 2018
by Dayeandknight
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