Disable your Ad Blocker! Thanks :)
Chapter 4
by
Nicegent42
What happens next?
They drink, they drink
Note: This was done with highly curated AI with edits from me because I am being lazy with writing at the second.
Liam cleared his throat and waved the bartender over for another round. Maybe three. The first drink had done nothing to help the confusing swirl of arousal, amusement, and pure what the hell spiraling in his chest. His best friend looked like he belonged on the cover of some trashy Halloween pinup calendar, and that thought alone made Liam’s eye twitch.
"Double vodka soda," he said, then glanced at Bret. "You want anything?"
Bret sighed dramatically, smoothing down the front of the absurdly snug maid dress with an exaggerated pout. “Mmm… surprise me, handsome,” he said, pitching his voice higher and sweeter, fluttering his lashes like some retro pin-up girl.
Liam blinked, his mouth hanging open for a second too long. “...What the fuck was that?”
“A performance,” Bret replied, voice dropping back to normal, though his grin stayed plastered on his face. “I’m trying to make your night magical,” he added in the sultry voice again, then immediately took a long drink, avoiding eye contact.
It was a mask. One that glittered, fluttered, teased. But beneath it, Bret felt like he was unraveling slowly, one lace frill at a time.
The barstool was hard, his posture felt foreign, and every time he adjusted the skirt to cover more of his thighs, it just rode up again. The wig itched. The bra was tight. The heels were already ****. But the worst part—the absolute worst—was that people kept looking.
And not in horror. Not laughing. Not mocking.
Interested.
Even Liam.
Especially Liam.
“Here,” Liam said, handing him a Sex on the Beach with a grin. “Strong, sweet, and way too colorful. Kinda like you right now.”
Bret took it and raised the glass with a dramatic flourish, the sultry voice back in full swing. “Cheers, sugar. Hope you’re enjoying the show.”
Liam coughed into his drink and gave him a sidelong look that made Bret’s stomach twist—but not in the fun way. He pushed that down with another gulp.
The drinks flowed easily. One became three before they even remembered food existed. And while Bret kept up the teasing, fluttering his lashes, licking sugar from his glass rim with too much flourish—inside, he just wanted the night to end.
But the bet was to stay till closing.
He’d lost the game. Liam had chosen the costume. And the terms were clear: full outfit, full night, no bailing early.
“I can’t believe I’m saying this,” Liam muttered, squinting at him. “But how the hell do you look like… that?”
Bret raised an eyebrow, swirling his straw through the melting ice. “Like what, sweetie?” he said, slipping easily back into that voice. Safer to stay in character. Easier to act like it didn’t bother him.
“Like someone who just destroyed my last functioning brain cell.”
Bret smiled—too wide, too plastic—but leaned in anyway. “Trade secret.”
He dropped the voice with a sigh and took another drink, letting it burn down his throat like punishment.
“I had no clue what I was doing,” he admitted. “Went to my sister, figured she’d laugh me out of the house. Instead, she got this look—and said it was time for ****.”
“****?” Liam blinked.
Bret nodded. “Yeah. Said this was for all the girls I cheated on back in high school. Called me a serial heartbreaker and said it was time I ‘felt what it was like to be hot and objectified.’”
Liam barked a laugh.
“I was like, ‘How does that make sense?’ And she just shoved me in a chair and said, ‘Shut up and suck it in.’ Next thing I know she’s contouring my cheekbones like a madwoman and picking out which push-up bra matched the dress.”
“She go full wax-and-paint mode?”
“Oh yeah. Waxed my brows. Glued on these lashes. She even taught me how to walk in heels. And I kept asking her how this was **** and she just smirked and said, ‘This is justice.’”
Liam chuckled, but then noticed how stiff Bret had gone.
“And… you okay with all this?” he asked, quieter.
Bret shrugged too casually. “Yeah, man. It’s just clothes and makeup. I’m not gonna lose the bet.”
But inside, he was screaming.
He’d gone too far to back out now. That was the truth. He couldn’t undo the makeup, or rip the stockings, or yank the wig off in the middle of the bar and admit that every look made his skin crawl and every moment in this costume chipped away at something he wasn’t ready to name.
So he kept playing the role. Kept fluttering lashes and giggling and teasing. Because if he acted like this didn’t get under his skin, maybe it wouldn’t. Maybe he could be man enough to pretend to be a woman—just for a night.
“You know,” Bret said in his girl voice, turning to Liam with a smirk that barely hid the tension in his jaw, “if I have to suffer, I might as well make it entertaining for you.”
Liam chuckled, sipping his drink. “You’re really committing, huh?”
“I always commit,” Bret said, almost too sharply. “That’s why I’m staying. All night. Until closing.”
Liam looked at him, the grin softening just a little. “Well… if it makes you feel any better, you’re the hottest fake maid I’ve ever seen.”
Bret groaned, face flushing again. “Don’t make this worse.”
“I’m just saying. You might be breaking hearts right now.”
“God help me if one of them is yours,” Bret muttered into his drink.
Liam didn’t respond. Just downed the rest of his glass.
And they ordered another round. Because neither of them was ready to leave. Not yet. Not while the line between performance and something real kept getting blurrier.
What's next?
Disable your Ad Blocker! Thanks :)
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
- 5,858 Likes
- 2,186,405 Views
- 926 Favorites
- 619 Bookmarks
- 384 Chapters
- 73 Chapters Deep
- All Comments
- Chapter Comments