Disable your Ad Blocker! Thanks :)
Chapter 6
by
Nicegent42
What's next?
Seats Taken
With Bret gone to the restroom, Liam tried—really tried—to keep his eyes on his phone instead of the spot where Bret had disappeared into the crowd. He opened his photo gallery, mostly just to distract himself from the mental image of those long, stocking-covered legs wobbling off in five-inch heels.
He scrolled past old dumb memes and blurry concert photos before his eyes locked on the few pictures he’d snuck earlier tonight.
The first one was Bret mid-pout, head turned slightly, staring off at nothing with those big fake lashes catching the bar’s warm lights. It didn’t even look posed—it was just a moment he’d caught while Bret was probably zoning out. But the way his lips were pushed out, the shine of his gloss, the curve of his cheekbone—it hit Liam harder than it should’ve.
The next photo was Bret with a mozzarella stick halfway stuffed into his mouth, eyes crossed and making a goofy face, completely unaware of how it somehow managed to still be hot. And the third was him sipping his Sex on the Beach through a straw, one pinky up for flair, the glass tilted just enough to show a little cleavage.
What is wrong with me, Liam thought, rubbing at his jaw.
He shouldn’t be staring. Shouldn’t be feeling this. Not for his best friend. His very male, very stubborn best friend who happened to look like the star of Liam’s confused, ****-fueled fantasies tonight.
But all he could think about was those damn legs. And the way those heels looked strapped around Bret’s ankles. And those lips, soft and pink and so easy to picture wrapped around—
He groaned and chugged the rest of his drink, slamming the glass down.
“Another for me and… Brittany,” he told the bartender, making up the name on the spot. “And two waters.”
The bartender raised an eyebrow but nodded. Then, as he leaned over to collect the glasses, he said under his breath, “So, uh… how’d you get your girlfriend to dress up like that?”
Liam blinked, then laughed, a little too loud. “Oh God, no. That’s not—I wish I could pull someone that hot.”
The bartender grinned. “C’mon, man. She’s smokin’.”
Liam shook his head and waved him off, heart pounding. “Nah, man. Her name’s Brittany. She lost a bet.”
The guy laughed and walked off, and Liam slouched forward, pinching the bridge of his nose. Brittany. Great. Just great.
Inside the women’s bathroom, Bret had barely managed to convince the stranger at the sink that he was just another girl with a weird boyfriend and a kink-themed costume. Her comment about him trying to get “fucked” lingered even as he left the bathroom with his head down and his heels clacking too loud across the floor.
When he returned to the bar, he was already pouting.
Someone had taken his damn stool.
Crossing his arms in irritation, he didn’t realize that the motion pushed up and emphasized the fake—but eerily realistic—cleavage that his sister had sculpted with pads and tape and makeup artistry that should’ve been illegal. He just knew his back hurt, his feet were killing him, and the last thing he wanted was to argue with some dude over a barstool.
Liam looked up and gave a crooked grin. “What’s with the face, Britt?”
“Some asshole took my seat,” Bret huffed, not even catching the fake name yet.
“Shit. Sorry,” Liam said, glancing around. “Wanna move somewhere else?”
“Not unless we’re teleporting to an empty bar.”
“We could play pool?”
“My feet hurt,” Bret grumbled.
That made Liam grin, because drunk Liam had exactly two modes: sarcastic, and enabling.
“Fine,” he said, and without hesitation, he reached out, wrapped his hands around Bret’s corseted waist, and pulled him forward—light but firm—guiding him down onto his lap.
“Wha—hey!” Bret yelped, shifting his weight—unintentionally grinding his ass against Liam’s crotch in the process as he tried to balance on the heels.
He instinctively looped an arm around Liam’s shoulders to steady himself.
Liam forgot how to breathe.
The sensation of Bret settling into his lap—soft, warm, all satin and lace and thigh-high stockings—short-circuited something in his brain. Bret felt like a hot girl grinding on him, completely unaware, and it took every bit of Liam’s self-control not to groan.
“I didn’t mean sit on you like some fuckin’ prize at a fair,” Bret muttered, shifting again—making it worse.
“A gentleman,” he added with fake drama, “would’ve offered the lady his seat.”
Liam, still reeling, smirked. “Then I wouldn’t have a seat. I gave you one, didn’t I? Hell, it’s warmed for your comfort.”
“You’re disgusting.”
“And you’re still sitting there.”
Bret scowled, but didn’t move. His feet were shot, and leaning into Liam’s shoulder helped him keep from wobbling like a newborn deer. It wasn’t comfortable exactly, but it was better than standing.
Then the bartender returned, setting down their refills and two glasses of water. He gave Bret a long, unmistakable once-over and leaned in with a grin.
“Hey, Brittany,” he said, handing Bret his drink. “Your boyfriend says you lost a bet, but damn—he’s a lucky man to have you. If he doesn’t take care of you, I’d be happy to.”
Bret froze.
The way the guy’s eyes dragged down his body made his skin crawl. It wasn’t subtle. Wasn’t flirty. It was sleazy.
It wasn’t checking out, it was hunting.
He hated it. Felt like he was under a spotlight, like the costume had peeled away and he was just on display. It made his stomach twist.
What a creep, he thought, jaw tightening. Jesus, is that what it feels like for girls?
Then the thought came, smug and confident even through the haze of tequila and glitter glue:
Nah. When I check girls out, they like it.
That guy was creepy. Leering. Trying too hard. Bret had game. Girls smiled when he looked at them. Flirted back. He knew how to handle attention, and he never made anyone feel like this—like some prize to be claimed.
He wasn’t that guy.
Still, he didn’t say anything—just blinked, stunned and silent, trying not to react while something unpleasant curled in his chest.
Liam didn’t miss a beat. Sensing the tension, he grabbed his water and flicked a few drops toward the bartender like it was holy water.
“Alright, cool it, Casanova.”
The bartender chuckled and backed off, leaving the two of them in silence.
“Brittany?” Bret finally hissed, voice sharp in Liam’s ear.
Liam shrugged with a smirk. “He asked. I panicked.”
“You gave me Brittany?!”
“It’s cute! It fits the look!”
“It sounds like a cheerleader from Ohio!”
Liam leaned in close. “Yeah, well, ‘Bret’ doesn’t exactly scream ‘sexy French maid.’”
Bret groaned, resting his forehead on Liam’s shoulder with an exaggerated sigh.
“This night’s cursed.”
“And you’re rocking it,” Liam murmured, still trying to keep his voice light, his thoughts far from the heat pressed against his lap. “You’re like… dangerously convincing.”
“Don’t say that.”
“Why? You’d make a hot Brittany.”
“Don’t say that,” Bret hissed again, but his grip on Liam’s shoulder didn’t loosen. His legs hurt too much to move, his head was spinning from the drinks, and somewhere underneath all the exhaustion and annoyance… he wasn’t entirely sure if he was still pretending.
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
- 2,186,700 Views
- 927 Favorites
- 620 Bookmarks
- 384 Chapters
- 73 Chapters Deep
- All Comments
- Chapter Comments