Chapter 5
by
Nicegent42
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Gotta pee
It was somewhere between the fourth and fifth drink—depending on whether you counted the tequila shot that appeared suspiciously on the tab—that Bret leaned over the bar and whispered, “I gotta pee.”
He stood a little too fast.
The glossy black five-inch heels wobbled underneath him, and before he could catch his balance, his hip bumped directly into Liam’s shoulder. Liam instinctively grabbed him—hands at Bret’s waist, firm and steady—and their faces were suddenly too close.
Liam looked up, lips parted in something between surprise and confusion.
Bret’s lashes fluttered—completely unintentional, a byproduct of the heavy mascara and long falsies his sister had lovingly glued on with scary precision. His mouth was slightly open, breath soft. The contact, the closeness, the way those big made-up eyes blinked down at him—it was all too much.
Liam’s heart skipped. Then raced.
He held on a beat too long before clearing his throat and letting go.
“You good?” he asked, voice tight.
“Just need to take off the stilettos of **** before they fuse with my spine,” Bret muttered, wobbling off toward the restrooms. “Be right back, darling,” he added in his girl voice, throwing a wink over his shoulder—just teasing. Just for show.
The exaggerated walk that followed had Liam practically frozen in his seat.
Bret didn’t even realize it—the way his hips swayed, how the skirt bounced just above those sheer, stocking-covered thighs. His sister had drilled the “feminine walk” into him, heel-toe, hips first, one hand brushing the wall for balance like some leggy sitcom seductress.
And honestly, it worked a little too well.
Bret passed the men's room and paused.
He stared at the little black-and-white stick figure on the door, then looked at himself in the mirror above the hallway sink. The long hair, the tight corseted waist, the makeup, the shoes. No way anyone would clock him at a glance—not tonight.
“Yeah… no way I’m going in there,” he muttered, turning and slipping into the ladies’ room instead.
Inside, the place was cleaner, brighter. Smelled vaguely like citrus and very questionable vanilla.
He shuffled into the stall, locking it behind him, then—ugh—hit the real challenge.
Inside the women’s bathroom, Bret shut the stall behind him and let out a long, weary breath.
His calves burned from the damn five-inch pumps, and every step sent a dull ache up his thighs, but the worst part wasn’t even the shoes. It was everything else.
He lifted the black satin skirt and hooked his thumbs under the waistband of the lace panties, pulling them down to his knees, careful not to let them touch the tile. His sister had picked them out with malicious precision—tiny, black, lacy, and trimmed in white to match the costume, complete with little decorative bows on the sides. His crotch, under the panties, looked flat. Convincing. Sexy, even.
And that’s what bothered him.
Earlier, when getting dressed, his sister had insisted on a full tucking job. “You want this to sell, don’t you?” she’d said, eyes alight with a mixture of **** and artistic passion. “You want to win, right?”
Bret had agreed.
He hadn’t realized what he was signing up for.
She made him lie on the floor of her bedroom, watched a YouTube tutorial twice for good measure, then handed him medical tape and skin-tight control panties. She even coached him through it—“Okay, now push your balls up. Like, back into your body. They’ll fit. Trust me.”
And the horrible part? They did.
It was the strangest sensation of his life. Not painful exactly—at least not at first—but so foreign it felt like he was rearranging anatomy. Pushing parts of himself back inside where they clearly didn’t belong,and then taping his dick down between his legs like some kind of DIY origami.
The end result was a smooth, believable front in his underwear. The first time he’d seen himself in the mirror, lace panties snug and flat, he’d gone completely silent.
His sister had just grinned and said, “Now you understand what women go through.”
And now, hours later, sitting to pee because standing wasn’t an option, drunk, sore, and definitely questioning everything—he laughed.
It bubbled up from nowhere. A ridiculous, breathy chuckle that started in his chest and cracked out of his mouth before he could stop it.
He tried to smother it with his hand, but the memory that sparked it was too funny to keep in.
The last time he and Liam made a bet like this—almost a year ago—Liam had lost.
And the loser had to shave their head. Completely bald. And keep it that way for a full month.
Bret remembered the moment Liam stared at the clippers in Bret’s hand like they were a loaded gun. Remembered the buzz. The slow horror dawning on his face as inch after inch of his hair hit the floor. And how Bret had sent a picture of shiny-headed Liam to every girl on his contacts list within the hour.
He laughed again, loud enough this time that it echoed off the tiled walls.
That’s when he realized—he wasn’t alone.
Someone else was at the sink. A brunette in a tight leopard-print top, mascara smudged from too many vodka cranberries and not enough water. She turned slightly, giving him a look in the mirror, brows lifted in suspicion.
Bret froze mid-step, already out of the stall, clutching his skirt and avoiding eye contact like it might be fatal.
“You good, babe?” the girl asked. “You were, like, giggling in there. Alone. Creepy ghost shit.”
Bret swallowed. “Uh. Yeah. Just… thinking about something funny.”
The girl blinked at him, eyes narrowing slightly. Then she tilted her head, appraising him top to toe.
“Why are you dressed like a French maid?” she asked, smirking. “Trying to get fucked or something?”
Bret’s stomach dropped so fast he nearly tripped over his heels.
He **** a nervous laugh and scrambled for an excuse. Something believable. Something not “actually I’m a dude who lost a pool game and got body-hacked into girlhood by my sadistic sister.”
“Oh, uh, it’s a theme party,” he said, voice pitched back up into that fake girly register, slightly breathy, laced with nervous charm. “Costume bet with my boyfriend. He, um… likes maids.”
The girl wrinkled her nose, then smirked. “Freaky,” she said, like that explained everything. “I kinda get it though. You look good. You got the legs for it.”
“Thanks,” Bret muttered, cheeks burning.
She turned back to the mirror to reapply lip gloss while Bret quickly washed his hands, eyes locked on the sink.
His reflection stared back, all lashes, blush, and cleavage.
I’d fuck that, his drunken mind whispered again before he could slap it back into place.
He stared harder, trying to find himself in the face looking back.
This is too much, he thought. And the night’s not even over.
His calves screamed, his toes were going numb, and he was definitely developing a blister—but pride wouldn’t let him back out. He said he’d last until closing, and goddammit, he would.
He dried his hands with shaky fingers, took one last breath, and plastered on his sultry mask again.
And then he strutted—limped, really—back into the bar, hips swinging more out of stubborn determination than grace, determined to get through this night… even if it killed him.
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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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