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Chapter 30
by
Mr Nice Guy
What's next?
Acceptance
Riley stared at the envelope in his hands, the glossy university logo catching the afternoon sunlight like a seal of fate. His heart was fluttering, stomach fluttering, everything fluttering.
He tore it open with a shaky hand, unfolded the paper, and read.
We're pleased to confirm your registration…
He exhaled with delight.
Thank God Isabelle had caught his mistake.
He'd almost locked himself into that ridiculous schedule—Physics? Engineering Statics? Like, seriously? What was he thinking? That kind of stuff wasn't going to help him in the real world. It wasn't going to make him more desirable. More... girlfriend material.
No, what he had now—this—this was the dream.
Contemporary Dance, where he could perfect the graceful, body-aware movements that made his hips sway just so.
Fashion Design, which would help him understand the tight, clingy, bright little outfits that looked so good in his videos and even better on him.
Stage Makeup, because looking this good didn’t happen by accident—and because the world deserved to see what he could do with a palette and a ring light.
Even Nutrition made sense. A good girlfriend needed to know how to take care of their man, right? And their body.
All of it made so much sense.
And then there was the final line at the bottom of the sheet, scrawled in blue pen in Isabelle's precise, confident handwriting:
Don't forget: Cheerleading Tryouts, Friday @ 3:30 PM – Wear the outfit we picked ;)
Riley's heart did a flip in his chest.
Cheerleading.
He'd never thought about it before—not seriously. He used to make jokes about it, honestly. Thought it was kind of dumb. But that was before. That was before Isabelle had explained it all to him. Explained it perfectly.
Chase was a football player. An athlete. A man.
If Riley wanted to be Chase's girlfriend—and he did, more than anything—it only made sense that he should be an athlete too. But, obviously, he didn’t have a football body. He wasn't built like that.
He was lean. Lithe. Toned in all the right ways. Like, not bulky, but bouncy. Tight.
Cheerleading was perfect.
It would keep him near Chase during games, give him something to offer. Something visible. He could cheer Chase on like a real girlfriend would, all while showcasing his flexibility, his energy, his dedication.
Besides, the idea of jumping and dancing in short skirts, thigh-high socks, and tight little crop tops—it wasn't just hot, it was empowering.
Isabelle had already signed him up for everything: yoga, private cheer coaching, even pole dancing classes to help with strength and fluidity. He giggled just thinking about it. Who knew training to be a cheerleader could feel so... spicy?
The money for it all came straight from his OnlyFans.
It had become his main income source, and he was proud of that. He was making good money now. And if he had to lick whipped cream off his chest while moaning into a pink silicone microphone—well, that was just content.
Everyone loved it.
And the best part?
Chase loved it.
He'd seen him at the gym earlier that day. Riley was on the cable machine, pretending to struggle just a bit more than necessary, chest bouncing in his tiny pink sports bra. He felt Chase watching him.
When they talked after, Riley could barely stop himself from trembling. Chase was just so nice. So big. So close.
When Riley bent over to grab his water bottle, he didn't even mean to back up into him. Not at first. But then he felt it—it—that firm bulge pressing against his ass like the promise of something incredible.
He moaned right there in the gym.
The contact should have lasted just a second, but Riley lingered, pressing back for a moment, enjoying the touch, the feel that he'd been craving for so long. Long enough to make the fantasies come flooding back. The ones he usually saved for his morning "meditation sessions." In the bathroom. Or curled on his bed with one hand massaging his chest, the other trailing lower, always fixated on that perfect, unimaginable, gorgeous dick.
What would it feel like without the material of their clothes between their bodies? What would it feel like in his hands? On his girls? On his face?
Lately, while picturing Chase during his kissing practices with Isabelle, it hadn't always been Chase's lips he had been imagining. The true object of Riley's desire, Chase's cock, had begun to appear. Maybe one day soon Chase would get the courage to ask Riley out. When that day came, he was sure that he'd had enough practice to reward his courage.
Riley flopped back onto the bed, letter still in hand, grinning to himself.
He was going to ace tryouts. He was going to become the hottest cheerleader that school had ever seen. And Chase? Chase was going to notice. He was already noticing.
It was only a matter of time now.
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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