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Chapter 8
by
Nicegent42
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Those Legs
By the time their latest drinks were nearly drained, the buzz had gone full throttle. Both of them were dangerously close to wasted, and thank god they were finally down to just water—though it wasn’t doing much to fix the haze clouding their heads.
Liam sipped his water like it might pull him back from the brink. Bret, still nestled in his lap, was warm and loose and flush with **** and laughter. The empty fry basket was shoved aside, his hand lazily swirling the straw in his watered-down drink.
And then, without warning, Bret mumbled, “I shouldn’t have such sexy legs.”
Liam blinked. “What?”
“I shouldn’t,” Bret repeated, a little louder this time, voice slow and syrupy. “It’s messed up. But I do.”
His stocking-clad legs shifted, rubbing together under the short skirt, the sheer black fabric sliding softly. The motion was ****—like he was enjoying the sensation without even realizing it.
Still holding onto Liam’s shoulder for balance, Bret turned his head, his lips inches from Liam’s cheek. “Hey. You ever feel up a girl’s legs when she’s wearin’ stockings?”
Liam blinked. “What—”
“I bet you haven’t,” Bret said with a sloppy snort. “I know you haven’t. You had, like, one girlfriend. For a week. In high school. And she dumped you because you brought her Taco Bell on Valentine’s Day.”
“I was being thoughtful,” Liam muttered defensively.
“She wanted roses,” Bret grinned. “You got her a Crunchwrap Supreme.”
“She loved Crunchwraps—”
“Yeah, and I love girls. And they loved me.”
Liam rolled his eyes. “Thanks, Casanova.”
But then Bret shifted again, this time with purpose, and grabbed Liam’s hand.
“No, seriously,” he said, dragging Liam’s palm down and pressing it directly onto his thigh—just above the stocking's garter. “Feel. Rub. Doesn’t that feel good?”
Liam’s mouth went dry. His fingers brushed the smooth stocking stretched over freshly shaved skin, the warmth of Bret’s leg under it undeniable.
Bret let out a low, pleased purr, eyes fluttering half-closed. “See? Told you. Feels good.”
It was too good.
For Liam, it was like flipping a switch he didn’t know was there. His hand stayed where it was, sliding just slightly—rubbing the soft fabric slowly, tracing the curve of Bret’s thigh. His other arm wrapped tighter around Bret’s corseted waist, fingertips brushing along the satin ridges and fake lace trim.
He could feel everything. Bret’s weight. The warm skin under all that costume. The way Bret shifted again—just barely—and accidentally ground back against Liam’s lap.
Liam was pretty sure he was going to cum in his boxers.
His breath came shallow. Every muscle in his body went tense, trying not to react. But he could smell Bret’s perfume—light, floral, sticky-sweet from the heat of the bar and how long they’d been this close—and the scent was dizzying. His lips were dangerously close to Bret’s ear now, and he could hear every soft breath, every slow exhale.
Bret was too drunk to register how any of this looked. Or felt. Or sounded.
He just leaned into the touch, still laughing softly. “This night’s insane,” he said dreamily, his head drooping against Liam’s. “I’m sexy. You’re drunk. I’m drunk. These heels are trying to kill me. Everything’s stupid.”
Liam nodded absently, his fingers still sliding up and down Bret’s thigh in slow, hypnotic strokes. “Yeah,” he whispered, “real stupid.”
“I can’t feel my calves anymore,” Bret murmured. “If I fall asleep like this, don’t let anyone take pictures.”
Liam chuckled, low and hoarse. “I won’t.”
“Except,” Bret added with a grin, “if I look hot.”
“You always look hot,” Liam said before he could stop himself.
There was a pause.
Bret’s drunken brain didn’t quite process the comment. He smirked lazily and turned his face slightly, cheek to Liam’s, their skin brushing.
“Mmm,” Bret hummed. “Smooth, Romeo.”
Liam’s heart pounded in his ears.
Then Bret said, “You smell nice. Weird.”
“Weird?”
“Yeah. Like… like you’re clean. But also like pine trees.”
“I shower,” Liam said, breathless.
“I don’t,” Bret said proudly. “I’m full of perfume and lies.”
Liam lost it—laughed softly against his neck, the heat of the moment bleeding into that familiar humor that always lived between them. But this was different. Closer. He could feel it.
So could Bret.
Even if he didn’t know what he was feeling exactly, the warmth, the safety, the pleasure of being touched, held, leaned into—it was too much. And not enough.
“Hey,” Bret whispered after a long pause. “You gonna rub my legs all night or what?”
Liam’s voice cracked. “You want me to stop?”
Another pause. Then, quieter, “...No.”
And the night kept slipping. Faster. Deeper. Louder around them, but somehow they were in a bubble. Just the two of them.
One hand on Bret’s thigh. One around his waist. One heartbeat away from something neither of them could joke their way out of.
Bret giggled, head still resting against Liam’s shoulder as he let his eyes flutter closed, one hand lazily tracing the rim of his drink, now forgotten.
“I bet,” he murmured, “everyone in this bar thinks you scored some hot chick.”
Liam's breath caught again. His fingers were still sliding up and down Bret’s thigh, slow and warm, now brushing closer to the soft edge of the inner seam. His knuckles hovered just shy of dangerous territory, and Bret wasn’t stopping him. If anything, he was leaning into it, legs shifting just enough to let Liam’s hand glide higher.
Bret sighed and let out a contented little noise. “Mmm… that feels nice.”
Liam swallowed hard. He was going to explode.
Bret, eyes still closed, smirked and said, “Bet you wanna kiss me, don’t you.”
Liam’s body tensed.
Yes. Yes, he did. More than that. He wanted to bend Bret over the bar, lift up that frilly little skirt, and bury himself inside whatever the hell this sexy creature had become.
But what he said was, “No. I don’t wanna kiss my best friend.”
Bret laughed softly. “Bullshit,” he whispered. “If I looked like this and wasn’t your best friend, you’d be all over me.”
Liam didn’t reply.
Couldn’t.
His hand was still moving, slow and steady, palm brushing over Bret’s inner thigh now, heat radiating through the sheer stocking, his thumb dangerously close to the edge of that high-cut lace panty line.
Bret shifted slightly again, the movement pulling a breath from Liam’s chest. His voice came out quieter this time, a little more serious, a little more playful beneath the surface.
“I bet you wouldn’t kiss me.”
Liam’s jaw clenched.
“You wanna bet?” he asked.
Bret laughed, head lolling a little as he grinned lazily. “Sure. You won’t do it. You’re gonna chicken out.”
Liam’s hand curled slightly, fingers pressing more firmly into the silky warmth of Bret’s thigh, and Bret groaned, hips shifting again as his back arched faintly in Liam’s lap.
“God… if you keep doing that,” Bret murmured, “I’ll let you pay the tab, and I’ll just melt into the bar.”
Liam laughed, voice ragged. “What do I get if I win?”
Bret grinned, then groaned again and tilted his head back, clearly feeling every movement of that hand.
“Ugh… fuck it,” he said. “Tonight’s been so screwed already. If you win? I’ll ask my sister to dress me up again. Like, a full redo. Hair, makeup, everything.”
He waved a hand vaguely at his face. “I’ll come over looking like this again, I don’t care. I never wanted to do this tonight, man. You have no idea. I felt like a joke walking in—but I committed.”
Liam raised an eyebrow, still rubbing Bret’s thigh, hand dangerously close to crossing a line they could never uncross.
“And that’s how confident you are?” he asked.
Bret grinned wide, his laugh low and teasing. “Damn right. You’re not gonna kiss me. I know you. You talk a big game, but this? This is where you fold.”
And Liam?
He said nothing.
Just stared at those glossy lips, at the flushed cheeks, at the soft flutter of lashes and the earrings that swayed when Bret tilted his head back again, still smiling.
Bret might not have known it yet, but Liam was already too far gone to walk away.
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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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