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Chapter 23
by
Lossleader2
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Covering a loan
As if to punctuate their previous conversation, Denver called Max into his office the next day.
“Maxine, I need your help with a client again.”
“Is it Jerry again?” Max asked, remembering the night he lost his anal virginity to Denver’s business partner.
“No, this is a private equity group. They are playing hardball on some of the terms of an agreement we made a long time ago and I need your help settling it.”
“Oh, okay. What do you need me to do?”
“You’ll come with me to the meeting and do the same thing as last time.”
“The same thing?” Max asked, nervous about the implications.
“If necessary. Is that a problem?” Denver raised an eyebrow.
“No, no problem sir.” Max said, still wanting to please.
“Good. I’ll pick you up again. I would recommend packing for the weekend, this might take awhile.”
“Sure, should I bring anything special?”
“Bring a change of clothes or two, nothing too casual. Where your dress from last time tonight.”
“Okay, see you tonight.” A pit formed in Max’s stomach. Something about this meeting seemed off.
That night Max slipped into his fancy red dress. It fit tighter than last time, his ass and tits had both grown since he’d used this outfit to seduce the last client. It wasn’t uncomfortable though and he showed a flattering profile in the mirror. The way the dress clutched at his ass and cupped his small breasts distracted from the small bulge of his caged manhood. Max packed a small suitcase and waited to hear from Denver.
Soon enough Max was back in Denver’s sleek BMW. They rode in silence for awhile and Max felt nervous.
“So what’s going on with the deal you made?” Max breached the silence.
“These guys are sharks. When I took over the firm we were in a bit of debt due to mismanagement from the previous head of the firm. I knew one of these guys and they offered us a loan with a number of conditions. As time has gone on, those conditions have changed and we haven’t had much leverage.”
“It seems like we make plenty of money, can we not pay them out?” Max was intrigued and delighted that he had Denver’s confidence.
“The money isn’t the issue. Our deal was structured with a number of perks that frankly we stopped providing.” Denver shifted in his seat a little.
“What kind of perks?” Max was getting nervous.
“You know how I operate. I keep things fun, and at the time they were close so I promised to keep things fun for them. As time has gone in we aren’t so close.”
“I feel like there’s something you’re trying not to tell me.”
“You remember Tanya?”
“Your old secretary?”
“Yah. She works for them now. Or did for awhile.”
“Like the way I work for you?”
“Yah, the way you work for me. Or maybe more than that.”
“So what are we doing here?” Max was getting scared.
“We’re here to negotiate with them. I let them poach Tanya, she agreed to go, but it sounds like she may have left and now they want me to remedy that. We only have another year or so left on the agreement, so I’m hoping we can just buy them out of whatever they’re looking for.”
“So I’m the second option?”
“You’re butter, not the bread.”
“What does that mean?”
“It means you flirt with them, you keep it casual, and if it doesn’t go the way we want, we walk away.”
Max sat with this for a bit. It felt like Denver was dancing around the possibility that Max was payment. “I’ll do whatever you want me to. I want to help however I can.”
Denver looked at Max as if for the first time. His eyes glanced across Max’s body and met his gaze. “I appreciate that Maxine.”
A half hour later they pulled up to the hotel where they were to have the meeting. They made their way to the fancy restaurant where they were sat at a table. They waited for awhile and Max threw back a cocktail.
“Denver!” A tall slender man walked up. He was clean shaven and hawkish, his blonde hair was greased straight back over his ears.
“Eddie, good to see you.” Denver said. They shook hands and Eddie pulled Denver in for a hug which he accepted smoothly.
“This is my guy Darell,” he motioned to the man following him, also wearing a suit. He was younger, probably not much older than Max. He was bald and only a little taller than Max was. Denver greeted him with a firm handshake.
“This is my secretary, Maxine. She’s here to help with the paperwork and to make sure I don’t get caught up drinking with you two.” The two men laughed at his joke and shook Max’s hand. Their eyes devoured him without any subtlety. Eddie made no show of hiding as he looked Max up and down and up again. Max felt like he might devour him right there.
“Good to meet you Maxine. Glad to have you join us.”
They sat down and Max was mostly quiet. Eddie and Denver did most of the talking. They reminisced about old times and Denver seemed to be genuinely enjoying himsel. Darrell was also quiet. He checked his phone frequently and chimed in when he was mentioned but mostly just sat idly. Max caught him staring at him a few times but it wasn’t anything more than he was used to at the office by this point.
“Maxine, are we boring you?” Eddie’s voice cut through Max’s internal thoughts.
“Not at all.” Max smiled politely.
“How long have you two been a thing?” Eddie asked. Max blushed a little.
“Max has been working with me for a little over a year now.”
“Is that right?” Eddie seemed thoughtful for a moment. “You know me and Denver used to get up to some stuff.”
“I gathered.” Max joked dryly.
“She’s fun.” Eddie said as an aside to Denver. “Denver here used to be the life of the party.” Denver shifted uncomfortably in his seat. Max had never seen him uncomfortable in any situation. “Has he told you about those days?”
“No.” Max said, a little curious but not wanting to put Denver out.
“Denver, you dog. A stand up citizen now are we?”
“I have a firm to run, I can’t be out partying with you guys all the time.”
“Or ever it seems.” A tinge of animosity in Eddie’s voice. “Denver knew all the girls in the city, if you know what I mean. They couldn’t get enough of this guy.”
“They were good times. Should we get down to business before it gets too late?”
“Give me a call Maxine, I’ll tell you all about it.” Eddie turned back to Denver. “We’re actually waiting on one more.” He looked over at Darrell who nodded. “And it looks like she’s here.” Eddie looked to the door where a beautiful latin woman was walking into the restaraunt. She wore a black dress that hugged her large curves and she walked with a sultry gait that had even Max eyeing her up and down. She came up to the table and put an arm on Eddie’s shoulder, she leaned in and kissed him on the cheek.
“Tanya.” Denver said quietly. His eyes lingered on her. Max watched with a pang of jealousy as Denver ogled his predecessor.
“Denver.” A seductive smile as Tanya acknowledged her old boss.
“You look well.” Denver said, seemingly broken from his spell and now a little uncomfortable.
“I am well. You look as dashing as ever.”
Eddie scooted his chair back and Tanya sat on his lap. “Max will you go ask for a seat for Tanya.” Denver said without looking his way. Max stood and walked away from the table, his eyes burned a little.
When Max returned Tanya was leaning in to Denver and they were speaking in hushed tones. Darrell and Eddie wore satisfied smiles, whatever game they were playing had worked.
“So Denver, these guys need you to step up your services. If you won’t do it as a favor for them, please do it as a favor for me.”
“This wasn’t part of the agreement.” Denver straightened.
“It wasn’t, but it is now. If you can’t furnish us with some help for Tanya, we will have to pursue repayment in full.”
Denver looked frustrated. “I can swing full repayment. I can’t get involved with this, not now.”
“Think of it as doing me a favor, which I would ever so appreciate.” Tanya leaned in again, her breasts practically slipping out of her dress. “They’re growing and I need your help. Think of it as being like old times.” Max watched as Denver fell for their trap. How could Max compete with her? Her skin was a milky brown and her voice a seductive song.
“I’ll see what I can do. But I want it in writing once this is done. There will be no more of this extortion business.”
“You know we can’t put this in writing.” Darrell chimed in.
“You’ll find a way or I’ll repay and we’ll be done.” Denver said with finality. Tanya smiled and stood to sit in the chair placed between Denver and Max. The conversation moved on, the shady business seemingly concluded, but Denver didn’t move on from Tanya. He spoke almost exclusively to her. As the night wore on Max considered fleeing and calling a car to go home. He couldn’t watch this anymore. Tanya’s hands were all over Denver and he was eating it up.
“I think the three of us can let you two get caught up.” Eddie said, clapping his hands lightly as he stood. “Maxine, would you care to join us upstairs?” Eddie asked in an oily tone.
“Denver is my ride, I don’t know if we should split up…” Max said awkwardly, hoping for a way out.
“Go ahead Maxine, I’ll call you in a few.” He nodded at Max and Max took this to mean that he would be done soon.
“Okay then,” max stood from the table, “let’s go.” Max watched as Tanya practically slid into Denver’s arms. His stomach turned as Eddie and Darrell walked on either side of him to the elevator.
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Office Intern
First day
Max is a young college dropout with no prospects, but an offer from his uncle to work for a large firm might be his chance to make his parents proud. Little does he know that “Office Assistant” means more than he expects.
Updated on Jun 4, 2026
by Lossleader2
Created on Nov 11, 2025
by Lossleader2
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