Lips Lickin' Lolli's For Money • Joshler One-Shot Stories

°A Date For Josh°

Oh my shit face!!!!!!!! YOU GUYS THIS JUST HIT 2K!!!!! Thank you all for being amazing and reading this. Here's An Update!!!
Riv

"It'll be fun, I will make sure by the time we leave today, you have a date with someone," Tyler said excitedly as he pulled Josh through the mall. The said boy ducked his head down as they walked into a retail store.

Tyler was snooping around and Josh stayed close by, making the younger boy turn around at him with a scowl. "Come on Josh, people are gonna think we are the ones together if you are right up my ass like that."

This made the older boy blush and take a couple steps back. "Y-You can't say things like that so loudly, Ty," Josh whispered, and it made the said boy roll his eyes. He scanned his eyes across the room, finding some blonde across the way.

He flapped his flannel in Josh's direction, "You have to go talk to her," Tyler told him. Josh looked up at him, although he was older, he was a bit shorter and he gave Tyler a confused look. "Come on, Josh. You've been lonely for too long, you complain about it to me every day, this is your chance."

"Uhm, Ty, If you haven't realized. I'm lonely and complain about it because I am literally socially awkward. I can't just go up to her and spike a conversation." josh pushed at his chest.

Tyler squinted his eyes at him, "We're gonna break that."

"W-what?" josh scoffed in his face. "You can't just break something like that in a few hours."

"You gotta start somehow?" Tyler let out a breath, seeing the blonde now exiting the store. "Fuck this, since we're already here." He made his way over to look at pants. He almost burst out laughing pulling out some leggings.

"I think someone misplaced these." They were a pair of white leggings, but Josh rounded the cart and saw there were more in a different size.

"No, they are meant to be there."

"No way!" Tyler quickly left, making his way to the fitting rooms. With his head low, Josh followed, but not before something caught his eye. His dirty little secret, he already had a few, hiding them from his best and only friend and college roommate. He snatched the clothing from off the rack, with quick steps to the fitting rooms.

He kept his head down as he stepped into the already open room, letting out a sigh when he was alone. "Joshie boy, is that you?" he heard from the stall beside him. Josh shook his head, hating his teasing roommate.

"None other." He heard Tyler giggle and move on with himself and looked down at the fabric in his hand. The soft silky feel, so flowy, so smooth, his heart racing so much quicker. He toes off his shoes and set the fabric on the bench slowly.

He tinkered with his pants before they fell and hit the floor. He smiled, rubbing his finger along the soft elastic band of his panties. It was a chrome-y kind of color, shimmering in the light. "What are you bickering at over there, Joshie boy?"

Josh covered his mouth as to not let Tyler hear his whimper. Josh then cleared his throat, "T-these, skinny jeans feel f-funny." Josh then reached over, grabbing the skirt, he lifted it up his legs, a feeling of relief burst through him.

He hasn't been given the chance to wear skirts in so long, so he let out all his worries as it snapped along his waist. He felt funny with the hoodie on, so he ripped it off, and tucked his band t-shirt in.

Tears brimmed his eyes, he felt so pretty. He felt so tiny too, he gave it a couple twirls, letting out another laugh. His cheeks blistered red, looking away for a second before catching sight of the skirt around him. He's definitely gonna buy it, he's just gonna come back tomorrow to get it.