Chapter 34
by
Mr Nice Guy
What's next?
Meditation Mentorship
Riley twirled on his toes in front of the mirror, skirt flaring just enough to flash the white lace edge of his panties. “Can you believe that routine?” he gushed, arms flinging upward like he was still mid-cheer. “I crushed it!”
Isabelle, lounging cross-legged on the bed with a bowl of strawberries, smiled like a proud parent watching their favorite child win prom queen. “You didn’t just crush it, babe. You owned it. Stephanie looked like she was trying not to cry by the end.”
Riley giggled, collapsing dramatically onto the bed. “You think I’m in?”
“I think you are the team.”
They both shrieked for a second, kicking their feet like tweens. Riley was still breathless when his phone buzzed beside him.
He picked it up and stared.
Then blinked.
Then screamed.
“OHMYGOD OHMYGOD OHMYGOD.”
Isabelle nearly spilled her strawberries. “What?!”
Riley flipped the screen toward her.
It was a text from Chase.
riley – just got home.
let’s go out tn? why wait?
send me ur addy – i’ll pick u up @6
dinner + movie. my treat.
Riley squealed like his soul had just left his body. “It’s happening! It’s happening!”
Isabelle's face lit up, but there was a flicker of caution in her eyes. “It is. But babe… this is a big step.”
Riley flopped back on the bed, hugging his phone to his chest. “I know… what if I mess it up? What if I do something wrong? What if he thinks I’m not good enough?”
Isabelle leaned over, brushing Riley’s hair from his face. “You’re more than good enough. You’re perfect. But… you still need to be ready. Remember your little meditation sessions?”
Riley’s cheeks flushed. “The ones in the bathroom?”
She smirked. “Mmhmm. The ones where you think about Chase’s... you know.”
Riley’s thighs squeezed together involuntarily. “Yeah…”
“Well,” Isabelle said, sitting up straighter. “You’ve learned a lot about yourself during those meditations. Now it’s time to think about Chase. He’s going to be nervous, Riley. Extremely nervous. Big guys like that don’t always know what to do with those kinds of feelings.”
“Shouldn’t he, like… take care of it before the date?” Riley asked innocently.
Isabelle blinked, then gave a theatrical sigh. “Oh, sweetie…”
She stood and started pacing slowly, fingers steepled under her chin. “This is why I keep forgetting you’re still learning. See, men—especially hot men like Chase—aren’t always in touch with their emotions and deeper needs like we are. Meditation? That’s way beyond most guys. They don’t even know how to start.”
Riley nodded earnestly. “So… what do I do?”
“It’s like this,” Isabelle said, settling onto the edge of the bed. “Your job, as his soon-to-be girlfriend, is to help him meditate. Just like you’ve been doing. Same rhythm, same movements… but it’s his body now. You’ll have to guide him. With your hand.”
Riley’s eyes went wide.
“My hand?”
She nodded. “You know what you’re doing. You’ve practiced. And he’ll be so grateful—so relaxed. And that’s what a good girlfriend does. She takes care of her man’s needs.”
A flush spread across Riley’s chest. “I-I get to touch it?”
“You’ve been staring at it for months,” Isabelle said with a wink. “Now’s your chance.”
Riley let out a dreamy sigh, imagining it. Meditating with Chase… helping him. Feeling it in his hand. Seeing it twitch, grow, pulse—
His heart raced.
Isabelle stood and extended her hand.
“Come upstairs,” she said. “We need to pick the perfect outfit. First dates only happen once, and your boyfriend is about to see what a real cheerleader looks like.”
Riley sprang to his feet, practically vibrating.
It was happening.
Everything he’d meditated about.
And more.
What's next?
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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- 384 Chapters
- 73 Chapters Deep
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