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Chapter 4
by
Lossleader2
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TGIF
The rest of the day was a blur. Max spoke with Harry who gave him a company card and a recommendation for the haircut. He gave Max a purse with the supplements he was to start taking and a list of instructions on staying in shape. He also gave Max a suitcase which he said had more uniforms and other stuff the associates liked to see.
“I’ve been here awhile and they like you to keep it interesting. If you’re going to wear the same outfit in a week, add an accessory or show some more skin and you should be fine. You don’t want too many comments about the way you dress.” Max nodded, practically in a state of complete shock as the world moved by him. “Be careful of the boss. Keep him happy. I would make sure you bring him his coffee in the morning when he gets in and check with him every day before you leave.”
“Cah ah takke thif off” Max sputtered through the gag.
“Sorry yah, take it out.”
“Why am I dressed like this? Is everyone here into other men?” Max felt like he could trust Harry enough to ask this.
Harry sat for a moment and then said, “I think they like to feel powerful and desireable just like anybody. Denver started this whole thing as a hazing ritual and more things have just gotten added to it over the years. It’s fun and for whatever reason it keeps this place going.”
“So you’re not into it like that?” Max felt like maybe Harry wasn’t part of it.
“I’d be lying if I said seeing you in that outfit with your gag on didn’t excite me a little. I went through the hazing ritual a long time ago when I joined. It was different then but it’s the same principle. You do your time and you get your reward. And sometimes that reward is another secretary’s ass to stare at as they prance around in fetish gear. I’m not going to psycho analyze myself to someone wearing a ball gag though.” Harry chuckled but Max felt alone. He had hoped Harry would be an ally in this, but it seemed like he was just as perverted as the rest of them.
“Okay, well I’ll try to make everyone happy.” Max said with little enthusiasm.
“That’s all you have to do.” Harry said, “Put your gag back on as you walk out.” Max could feel Harry’s eyes on his ass as he left.
The rest of the day was uneventful. Before Max packed up to leave he did as Harry said and went to say goodbye to Denver. He wasn’t in his office so Max took the opportunity to leave without saying anything.
At dinner his parents asked him about the job, eager for more good news. Max didn’t have the heart to tell them about the weird office dynamic and the outfits they made him wear.
“It’s good, the boss likes me, they want me to stay long term i think.” Max lied slightly.
“Thats great news! Congratulations.” His parents beemed with pride.
Thursday Max dressed in a nurse outfit and got comments about it not being exciting. The standards were already getting higher. Dylan still didn’t say a word to him and his morning meeting with Denver was hard.
This time when Max walked in with Denver’s coffee, Denver turned all the way to face him in his seat, leaving his crotch at eye level with Max. He held the leash tighter this time forcing Max’s face uncomfortably close to his manhood. Max could smell his cologne but also the distinct smell of his dick. He could see its outline in the seam of his pants and shuddered at the thought, it was clearly quite large. Despite his aversion he couldn’t help but stare at it. It was transfixing to trace the shape of it with his eyes and imagine what it looked like. Denver didn’t even say anything, he just sat there with Max practically between his legs.
“You sure this isn’t the perfect job for you?” Denver chuckled. Max blushed and tried to look away. Denver pulled his leash dragging his head against his thigh. “Tell me this doesn’t excite you and I’ll leave you alone?” So this was what Harry was warning him about. Max remained silent, his cheek pressed agains Denver’s inner thigh. Suddenly Denver reached down and groped Max’s crotch. His touch was firm but not aggressive but he was so fast MX barely reacted. Denver’s hand caressed Max’s aroused manhood. He smiled in Max’s face and released the leash. Max fell backwards onto his ass, his legs splayed out haphazardly and his skirt riding up. Denver could see his panties straining against his average sized erection.
“Look at that. That’s what I like to see. We’re going to have to cage that beast to keep you from hurting someone with that thing!” He laughed. Max covered himself but composed himself enough to kneel again.
“You can go back to your work now girl.” Denver said and waved him off. Max hurried out of his office with his tail between his legs.
After work Max went to the salon and got a bob cut, his straight black hair framed his face nicely and the hair stylist complimented his girlish features. He felt weird about the haircut but felt he could play it off with gel when he wasn’t at work.
That night his phone buzzed around 3am. He checked his messages and it was from the same number claiming to be Dylan.
“You up?” Was all it said.
Max debated on what to send back but landed on just saying “yah.”
“I want another pic. This time stick your tongue out at the camera and roll your eyes back into your head. I want to see the haircut.”
Max debated about what to do but Denver’s voice told him he had to do it. He set his phone up and took the picture. He was a little disgusted at how slutty he looked. He looked alot like a girl posing for a cumshot. He sent the picture.
“Tomorrow’s friday, you know what that means?”
“No.”
“Boss is leaving early. You and I should schedule some time together.”
“What does that mean?”
“You’ll see I guess ;)”
Max decided not to text back. He waited awhile and just before he put his phone down, Dylan texted again.
“Send me a picture of your ass without panties on.” Max was frustrated and felt trapped. He opted to not respond. A couple minutes later another text.
“Don’t make me talk to Denver.” Max felt a cold run through his gut. He decided to play coy and took off his underwear. He snapped a picture of his plump ass cheek and sent it.
“Next time I want to see everything.”
Dylan didn’t text anything after that and Max decided not to play into it further. One more day to go, thank god he thought to himself.
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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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