Disable your Ad Blocker! Thanks :)
Chapter 58
by
Mr Nice Guy
What's next?
Rom-Com and Recon
The house was quiet, dimly lit by the soft flicker of the TV. Isabelle had kicked off her heels hours ago, curled on the couch in an oversized sweatshirt, a glass of wine forgotten on the coffee table. She'd put on some throwaway rom-com, the kind with cookie-cutter couples and paper-thin plots—something she could half-watch while basking in the glow of her own handiwork.
She'd done it.
The game had been perfect. Riley had been perfect.
Everything she'd been shaping, building, guiding—it had all come together on that field. The choreography, the confidence, the crowd chanting his name. Her creation, her beautiful little project, her masterpiece of raunchy ****, standing under those stadium lights and shining like a diamond. Isabelle had filmed nearly the whole thing, of course. For Riley. For his fans. But also for herself. Watching him dance, flip, cheer, glow... God, she could've cried.
She'd made that.
Somewhere between the third act and the credits, Isabelle had dozed off. The wine, the warmth of the blanket, the afterglow of success—it all dragged her under like a tide.
The jingle of keys in the front door brought her half-awake. Then the sound of a body thudding into the wall, followed by a muffled giggle. Then a shhhhhh that turned into a laugh. The door creaked open wider, and Isabelle cracked one eye open from her spot on the couch.
Riley.
He stumbled into the front hallway with Chase close behind him. Both of them were glittering with sweat and booze and the shine of something young and golden. Riley's heels wobbled under him, but Chase's strong arm kept him steady. They were trying to whisper, but they were both awful at it—drunk giggles spilling out as they bumped into furniture and held onto each other like they might float away.
"Careful," Riley whispered, which sounded more like a squeal. "You're gonna knock over the umbrella stand again!"
"I didn't knock it over last time," Chase murmured, laughing against Riley's neck. "You fell into it."
"I was trying to dance with it!"
They both giggled, and Isabelle smiled to herself. She didn't move. Just watched.
Riley was dressed in that little black dress she'd picked out. The one she told him to save for a special occasion. It clung to his every curve, the skirt riding dangerously high up his thighs, the sweetheart neckline exposing the tops of his perfect breasts. His makeup was a little smudged now, his lipstick kissed off, his hair tousled and wild. He looked ravished. He looked radiant.
They paused at the bottom of the stairs. Riley looked up the steps like they were a mountain.
"You think we'll make it?" he whispered, holding Chase's arm.
"Only one way to find out."
Riley giggled again as Chase scooped him up bridal-style—Riley let out a breathy "Oh my god," followed by more laughter—and the two disappeared upstairs, stumbling and swaying.
Isabelle waited. Counted to twenty in her head.
Then she slipped off the couch.
She padded quietly through the house, her bare feet silent against the floorboards. She didn't go all the way upstairs—not right away. She just lingered at the base of the stairs and listened.
A few more giggles.
A creak of a bed frame.
A door half-closed, not fully shut.
Then she moved.
She climbed the stairs slowly, deliberately, not making a sound. She passed the bathroom, then Riley's door—open a crack. She didn't look inside. She didn't need to.
Instead, she kept going to her own room, just down the hall. She opened the door, stepped inside, and left it wide open behind her.
She sat down on the edge of her bed. Her heart was thudding, and she knew why. One might think it was the wine. Or maybe the thrill of the erotic encounter about to occur. But it was neither of those things. Riley was about to pass another milestone, and Isabelle couldn't wait. Her work was paying off, and she couldn't wait for the next steps.
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
- 5,860 Likes
- 2,189,873 Views
- 932 Favorites
- 621 Bookmarks
- 384 Chapters
- 73 Chapters Deep
Comments moved below the chapter.
Jump to comments
Comments