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Chapter 3
by
Lossleader2
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Wednesday
Max put on his regular clothes and threw the garment bag with the maid costume over his shoulder. He was out the door at 6am and was in the office bathroom by 6:45. He changed into his maid outfit, put the leash on and adjusted it in front of the mirror. He wasn’t sure what to do with the ball gag but decided to follow Harry’s instructions and put it in his mouth. He got to his desk and sat down and waited for the associates to start coming in. His stomach was a pit. At around 7 Harry walked in the door.
“Morning.” Harry said cheerily.
“Mormih’” Max mumbled through the gag.
“You look good. How does it feel?” Harry said.
“If oh hay” Max struggled to form words and spit began to pool around the gag.
“You can take the gag out if someone tells you to. Make sure it’s in when the boss walks in though, he likes his secretaries very professional.”
Max nodded, not wanting to drool on his outfit. Harry entered the door behind Max go go to his office. Over the next hour the other associates came in, most said a brief hello and moved on, a few commented that Max looked good in his outfit. Then Dylan walked in the door. He looked tired, probably a late night considering the time he texted Max.
“Hewwo” Max was nervous but you could barely tell as he formed the words around the plastic ball in his mouth.
“Hi.” Dylan was curt and walked through the door without stopping. Max was relieved but almost a little disappointed. He had expected Dylan to make a comment about him or say something about the pictures he made Max take the night before. Maybe it was a different Dylan? Maybe it wasn’t Dylan at all. Now Max was really worried. Who did he send that picture to? Max didn’t have much time to think about it as the door opened again. Max recognized the face from the website, it was Denver. He was a tall man with dark skin and a tight haircut. He was the regional partner and probably the person his uncle had asked about getting Max a job.
“You must be Max!” Denver said with a smile.
“Hu Mr. ‘Envew” was Max’s response.
“You look fantastic. You remind me a lot of our last secretary. Welcome to the firm. I’ll be by to do a proper introduction later today. In the meantime, there should be a folder on your computer labeled Tanya, that was our old secretary, go ahead and open that and review her notes would you?” Denver smiled again and breezed through the door.
Max wiped his mouth with a napkin and looked around for the folder Denver told him to review. He found it on the desktop and opened it. Inside were a couple of folders labeled things like “contact list”, “receipts”, and other admin task related things. But sitting loose at the top of the folder was a text document labeled “Tanyas notes” and a photo album file labled “Tanya’s Album”. Max decided to click on the notes.
It was a long document, it appeared to be over 50 pages. It started with some basic first day notes but got more organized around page 3. Most of it was stuff that Max had done or been told about, documenting receipts, mailing letters, and doing admin work around the office. Something did catch Max’s eye as he went through her notes. There were a lot of mentions of the various associates in her day to day notes. They would list the name and then a phrase like assist or relieve, but sometimes they would be a location like utility closet. Often times these notes would have what looked like times. Max assumed this was some kind of task related time keeping method. No one had said anything about keeping records of the tasks that he did but this made sense. Before Max could scroll much further the phone on his desk rang.
Max answered through the ball gag, a stifled hello.
“Max, i meant to tell you and I’m glad I called, take the gag out when you answer the phone, if a client calls we dont need them struggling to hear you. Come down to my office.” Denver’s voice was smooth and commanding. Max grunted his agreement and got up to go to Denvers’ office. He made his way through the door behind his desk and into the ‘bullpen’. This was a wide open area with the lower ranking accountants and their cubicles. Lining the walls were the associates offices and Max made his awkward journey to the back corner where Denver’s office covered almost the whole back wall. He could feel the other accountant’s eyes on him the whole way down, his leash jingled a bit as he walked and he stumbled a little in the high heels. He felt stupid and a little bit excited with everyone’s eyes on him. He felt like a show pony. He reached the large wooden door and knocked. He heard Denver’s voice through the door and entered.
“Max, thank you for joining me!” He was propped up behind a large wooden desk with his computer and several stacks of paper on it. There were a couple of leather chairs facing his desk and Max went to sit down on one to begin their meeting.
“Whoah, sorry Max, those chairs aren’t for you. You’re over here.” He motioned behind his desk next to him. Max couldnt see over the desk so he made his way around it. Next to Denver was a small, cushy looking mat. Max hesitated, not sure of what to do. Feeling Denver’s eyes on him he chose to kneel on the mat, it seemed the only reasonable thing to do. Denver looked at him approvingly. He stuck his hand out, which now sat around Max’s eyeline and left it there expectantly. Max felt like this was a test. He looked down for something to give him and realized what he wanted. Max took the lead end of the leash and placed it in Denver’s hand. He gripped it softly and smiled.
“Very good. As you’re here longer I’ll make sure to get you a chair but since youre new I figured it’s best to start from the bottom. You can take your gag out now.”
Max unclasped the gag at the back of his head and removed it, drool slid out of his mouth and splattered on his outfit. He kept the gag in his hand, unsure of what to do with it next.
“Max, I have to say I’m pretty impressed. You’re figuring things out very quickly around here, especially for your third day.” Max’s stomach felt warm with the compliment.
“Thank you.” Max said.
“Sir.” Denver’s tone turned flat and commanding.
“Thank you sir.” Max repeated hastily.
“Now I know Harry has been showing you around lately, what has he told you about your job so far?”
“Well, he explained that I’m supposed to get the mail and answer the phone. I’m supposed to file the paperwork and email the associates when the client’s reach out. I…”
“Yes yes, very good.” Denver cut max off before he could continue. “Typical Harry, he has always been a timid guy.” Denver chuckled a little. “Did Harry tell you to wear the outfits?”
“Yes sir.”
“Did Harry tell you about your duties besides the admin paperwork?”
“He said you would explain all that stuff sir.” Max was getting uneasy.
“Your uncle got you this job right? Did he tell you what it would be?”
“He did sir, but he didnt tell me about the job.”
“Have you had a job before?”
Max felt embarrassed and didnt want to lose his job. “No, sir”
“Did you finish college?”
“No sir” Max was worried now.
“Do you want this job?”
“Yes sir.” Max was practically already begging.
“How much do you want it?”
“I need this job sir.”
“Good.” Denver let that hand in the air for a moment as he looked Max up and down. “Step one, you’re going to need to look the part more. The outfit fits nicely and you have the right bone structure, but you’ll need to cut your hair and start taking the supplements Harry will give you.”
“Supplements?” Max asked. His head rocked to the side as Denvers hand delivered a quick slap to his cheek. It felt hot and the pain radiated through his head but subsided quickly.
“Don’t make me repeat myself.”
“Sorry sir, what supplements?” Max held back tears.
“You’re here to handle the day to day. Most mail and phone calls will be junk and most filing is done digitally. You’re not here to be a traditional secretary. You’re here to make sure the office continues to run at record breaking pace. That means everyone here is under a lot of pressure. You looking good and entertaining the associates and the managers and me helps keep things from getting too tense around here. Do you understand?”
“I’m not sure sir. You want me to entertain?” Max didnt know what to think. Maybe the outfits weren’t a prank. Maybe this was the job. Were these men attracted to him?
“I want you to do whatever anyone asks you to do as long as I approve it. That can be anything from picking up dry cleaning to showing up for work with a boob job so that the associates have the correct motivation.”
“A boob job sir? You want me to get surgery?” Max was about ready to walk out. What was he doing here, he was kneeling at this mans desk while he talked about turning him into a whore for the office!
“Is that a problem? I can call your uncle and tell him it didn’t work out. I’m sure he and your family will understand.”
“No wait, dont do that sir.” Max was panicking. “I can’t let my family down.”
“Good, see how important proper motivation is? Thats what I want you to be around here. If you show up and you look good and you show off some skin and you flirt with guys like Dylan you’ll be handsomely rewarded for your trouble. Our last secretary was almost making 6 figures before she got another offer.”
100,000 dollars was a lot of money. He could finally move out of his parent’s house. Could this be worth that?
“Do I have to do sexual things? Sir.” Max asked awkwardly.
“It seems like you’re already doing them. I got this photo from Dylan this morning.” Denver held up his phone to show the picture of Max showing off his ass in the mirror. Max noticed that it was sent in a group text and the message accompanying the photo was “the intern looks qualified”. Max felt humiliated. He didn’t think Dylan would share the photo and he only sent it because he was scared of losing his job. Now everyone was looking at him like some slut.
“Now like I said, you have a good frame but you need to get a woman’s haircut and start dressing to impress. I want you to look fuckable if I can be blunt.”
“Sir I don’t even like guys.” Max stammered.
“That’s why we’re having this conversation. I’ve told you what the job is. Now its up to you. I will say, you took to this like a duck to water. I’ve never had an intern walk in here and immediately know to kneel by my feet and put their leash in my hand. You clearly want this, maybe you just dont realize it yet. Or maybe youre ashamed of it.”
Max knelt there for a moment, his head buzzing with the all this new information. Was this even legal? Could he get in trouble? What if one of his coworkers wanted to have sex with him? Could he go through with something like that? Was Denver right? Did he kind of like the attention and the sexiness of it all? He did send Dylan a picture without much prompting.
“Well?” Denver seemed impatient.
“I would need money for a haircut and stuff.” Max said weakly. He wasn’t sure he’d ever step foot in this building again but he didn’t want to turn this down without thinking about it.
“You can sort all that with Harry. All I want from you right now is to know if you can handle the job.”
“I can handle the job, sir.” Max felt a piece of his pride break away. Whether or not he decided never to return, he had submitted himself to this in that moment.
“Glad to hear it. Put your gag back in and go grunt to Harry. He’ll get you set up with what you need.” Denver smiled and as if to put a point on it, he slapped Max’s ass as he stood to walk out. Max yelped quietly and started to walk away but was suddenly yanked back by his neck, forgetting the leash that bound him to Denver. He turned to face Denver who didn’t even seem to notice he had almost yanked Max to the ground. He met Max’s gaze and smiled, he handed Max the leash and waved him out of his office.
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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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