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Chapter 3
by
Dayeandknight
What is Bret dressed as?
Bret the Pretty Pretty Princess (by Spooky)
Liam nearly fell off the stool when he saw Bret, He'd actually seen his girlfriend Nina first, she was dressed as some Anime Character, he wasn't sure which, but She had already shown him his costume so it was easy spotting her.
Bret was also easy to spot but the hard part was recognizing him, Bret was dressed in one of the most elaborate princess dresses he'd ever seen, he wore realistic wig, heels, he had cleavage for god sake.
When Liam had picked Princess for Bret's costume, he had picked it for a good reason, his girlfriend. Nina loved Princesses, she was a totally Disney Adult, just absolutely Obsessed.
Nina and Bret wandered over to Him.
Wow... Liam Thought... Bret looks really good.
"Wow!" Liam Said... accidentally letting his thoughts out of his head "I mean... like I expected you to flake on the bet."
"Like she'd let me..." Bret said half heartedly...
Nina chimed in energetically "There was absolutely no way I was letting a chance like this to slip through my fingers!" Bret shrugged his shoulders as if to say 'See?'
Nina helps Bret fix his dress over the stool before taking a seat herself. And the two of them began recanting their afternoon. Liam couldn't stop watching Bret's Ruby red lips move as he talked.
"I've been trapped in this thing all afternoon, She had me put the Corset on at 1:00"
"-Because it took hours to get you ready! and let me remind you, we were still late, I should've gotten you started at Noon."
Bret sighed, "Dude, I blame you for this, you triggered something in her, she's got me wearing two pairs of underwear, I've even got 2 wigs on."
"What?" Liam asks confused
Nina groans, this is clearly a back and forth they've had before. "No, you're wearing pair of panties and shaping shorts, You're only wearing 1 wig... you just also have clip on bangs."
"That Counts as a Wig" Bret argues back.
"It doesn't sound like a wig..." Liam jumps in joining Nina's side.
"You..." Bret turns his attention to you... he's actually really cute when he's all fired up like this "You can stay out of this until you're in the dress." he turns back to Nina, "And the two bras?"
"That one's true, but how else were we supposed to create cleavage, have you ever seen a princess without cleavage? the first bra is padded, and the second was to push your chest up and together."
"I'm telling with the amount of you of things I'm strapped into she's got some new Bondage kink or something." Bret jokes turning back to Liam.
For A Moment Liam and Bret's eyes met... a moment of unexpected intensity for Liam and he blushed and returned to his drink.
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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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