As the de facto leader of the group, Jack was used to being responsible for their personal hygiene. Thankfully, newcomers David and Les came from a loving home, so they didn't need as much of a reminder. Although they had somewhere they could sleep, they decided that as a sign of solidarity, they would bunk with their new friends for their first night. What David hadn't accounted for was how comfortable they would all be with their bodies.
As twenty boys throughout different stages of puberty flaunted their stuff around the room, David tried to shield Les's eyes. Jack noticed the occurrence and walked over to the pair, slightly amused and completely nude, save for the towel around his neck.
"Wow David, look at Jack's thing! It's thicker than yours!" Les shouted with no concept of consequences. David blushed furiously and was about to retort that his was longer, but realized that wasn't necessarily information to share.
"What's the matter Davey? You's a bunch of prudes or something? The kid's gotta know what he has to look forward to", Jack asked, brazenly giving them an eyeful.
"We change in front of each other all the time at home", David explained, "but as far as strangers go, he's pretty sheltered."
Jack grinned at Les's vehement denial.
"Well, maybe it's time to change that. After all, you guys are Newsies now, and Newsies don't hold any secrets. Privacy is hard to come by, if you catch my drift, especially for private time."
David blushed again.
"What does he mean? Like peeing?" Les asked innocently.
Jack looked at David in shock.
"You mean you haven't taught him about you know what?" Jack asked, pantomiming the action in front of him. "I mean, come on, every guy's gotta know about that."
Les looked back and forth between the two older boys, desperate to know what you know what was. Furious that his brother was keeping something from him, he tore off his clothes and stood with Jack, defiant against his brother.
"If you're keeping information from me, I'm going to go with Jack so he can teach me stuff!" With that declaration, Les crossed his arms and huffed, staring at Jack for confirmation. "You will teach me stuff, won't you?"
Jack looked down at the newly nude boy.
"I'd be glad to, but David's in charge here. Only if he says yes."
David realized he was losing this battle and came up with a compromise.
"Look Les, Jack can teach you stuff IF and ONLY IF I'm there too."
Jack and Les looked at each other and Jack broke into his signature smile.
"Well, alright then. Dave, you might wanna hustle because the first lesson is starting in the showers in 5..4…3…"
David quickly starting undressing, desperate to catch up to the fleeting sight of his younger brother and new business partner. In his haste, he couldn't help but admire the tight ass of the Cowboy Newsie. He finished undressing and ran after them.
Jack turned back to see where David was up to. Hmm, I may be thicker, but he's definitely longer.