Playing the Bosses

Returning 6 September + Bonus Content

A/N: Hey y'all! So I've decided to start my two-week break, and this book will be back on 6 September. Before I go, I thought I'd share this short featuring the men. This happened the morning after Eva strapped Caleb.

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Justin and Caleb were in the kitchen preparing their separate breakfasts while Eva and Adrian were still sleeping. Other than the sounds of the dishes and blender, the space had otherwise been quiet as Justin tried to muster the courage to ask Caleb what he wanted to ask.

"You're quiet this morning," Caleb said, breaking the silence between them. "Don't tell me you're making shit weird after last night. And after I complimented you for being an open-minded straight guy."

"It's not that," Justin assured. "I just... There's something I wanted to ask you."

Caleb tilted his head to the side with smirk. "No. I don't actually want your dick. I was just fucking with you."

Justin rolled his eyes, huffing his annoyance. "Not that, Caleb."

"Then what is it?"

"So um... Eva told me I should ask you about um... prepping."

"Hm?" Caleb feigned confusion. "Prepping for what?"

"Prepping for... you know... what you guys did last night."

"We did a lot last night. I fucked her. She fucked me. I sucked off Adrian. You might say we had sex like three or more times last night."

"You know what I mean, Caleb."

"How could I if you don't say it, Justin? If you're gonna do it, you gotta at least bee comfortable saying it. Unless you actually don't...?"

"I do!" Justin blurted. "It's just... new. And..."

"Highly stigmatized because cis-het dudes think the only way to get pleasure is to put their dick in someone?" Caleb reached out and put his hand on Justin's shoulder with an expression of assurance. "Just say it, Justin. That's the first step." Holding his lips tightly together, Caleb tried to hold in his laughter.

Justin shook off Caleb playfully before answering. "Fuck it. Eva told me to ask you about prepping for anal... to receive it."

"There it is! Now, was that so hard?"

"Are you going to explain or not?"

"I need you to take it one more step, okay? Just admit you're asking because you want Eva's strap in your ass."

His nostrils flaring, Justin shook his head and turned back to his breakfast. "You're being a dick right now. I'll figure it out or ask Adrian. It seems simple enough, I just have to clean out."

Caleb pointed a finger at Justin. "That's where you're wrong, my friend. Not only do you need to clean out. You also need to stretch."

"What? Like for flexibility?"

At that, Caleb bursted out laughing, unable to contain himself.

"He means you need to stretch to prepare for something larger than you're used to, to go inside of you." Adrian casually walked into the kitchen from the hallway and went straight for the refrigerator.

"You know, I don't know why I didn't go to you first, Adrian," Justin said, turning his attention to him. "You're way more reasonable... How do I go about prepping for anal?"

"Caleb's gonna be your best resource there... He's a pro at that sort of thing," Adrian added with a sneer.

"Yeah, but he's being difficult. Can you just explain it to me?"

"He can't because he doesn't know how to take dick," Caleb interjected. "Adrian doesn't bottom for that. Did you just assume because he's bi, Justin?" he teased.

"No! Er— I just thought that since the two of you... I mean you two and Eva... she... you know..."

"Calm down, Justin," Adrian said with a chuckle. "Caleb is continuing to fuck with you while trying to shit talk me like the brat he is. I don't bottom for anal."

"He'll take some fingers, though," Caleb added. "A good old fashioned prostate massage... That's why more guys need to be okay with anal play. It feels fucking amazing."

"I really didn't expect this conversation to go here," Justin griped.

"Excuse Caleb," Adrian replied. "I'm sure this was a... vulnerable question to ask."

"Alright, alright," replied an entertained Caleb. "I'll explain it all to you, Justin. Products and all."

"Did it really need to be this difficult?"