Chapter 2
by
Lossleader2
What's next?
Uniforms
Max unzipped the first garment bag and froze in confusion. Inside was what looked like a maid costume. It had the black and white dress, a pair of black high heels, and a collar with a heart on it. On top of that the outfit came with a pair of handcuffs and a plastic ball on a strap that Max recognized as a ball gag.
Setting it aside Max assumed this was a mistake and began unzipping the next one.
Max sat in his room, surrounded but what could only be described as fetish gear and wondered what he was going to do. He couldn’t wear these to the office but Harry had been specific. Was this some kind of joke they played on interns? It must be. Should I play along? Or does it show professionalism if I just wear my normal clothes. Max looked through the outfits again and decided to try on the maid outfit. It was the least revealing and could be seen as kind of funny. He decided to bring it with him and change in the bathroom, though he wasn’t sure what to do with the ball gag. He packed it anyway but didn’t plan to actually put it on. He pictured laughing with the associates and getting praised for playing along with their prank. Maybe this would be a chance to make some friends.
The maid outfit fit surprisingly well for being cut for a woman. It showed off his tan legs and skinny arms. It cut down a little low on his chest but was otherwise mostly suitable. The collar did make it look very sexual. He looked in the mirror and realized that he looked like a sex **** or something. He did look kind of cute and in the moment he tried fitting the ball gag around his neck. He plopped the red plastic into his mouth and snapped a picture in the mirror. Suddenly a text popped up on his phone from an unknown number.
“Did you try on the uniforms?”
Max was freaked out but knew it had to be someone at work.
“Who is this?”
“Harry. Make sure you wear one of the uniforms tomorrow.”
“Okay, which one should I wear? Are you sure you gave me the right ones?” Max hoped he would say no.
“I’m sure I gave you the right ones. Take your pick.”
“Okay, do I have to wear all of the parts?”
“Yes. Send me a picture once you try them on.”
Max was worried but didn’t want to be seen as not a team player. He sent Harry the picture he just took.
“Perfect, you look very cute.” Harry replied.
Max’s stomach felt warm from the compliment but also nervous.
“I feel stupid in this.”
“Just be ready to roll with the punches tomorrow. It gets easier.”
“Thank you.” Max said.
Max wasnt sure he was ready to get made fun of like that but decided it was best not to piss anybody off and dissapoint his parents.
At around 2am, Max lay there wide awake. He couldn’t sleep. His phone buzzed and be checked it, it was another new number.
“Send me another pic.” Max was confused.
“Who is this?”
“Dylan, send me a without the maid costume.” Max didn’t know what to do. He turned on his light and put on the latex dress and stockings. He snapped a picture in the mirror and sent it to the new number.
“Take off your clothes. I want to see your pussy.”
Max hesitated. “Im a guy.”
“Bend over in front of the mirror and take a picture.”
Max was scared now but did as he was told. He took off the outfit and left the stockings and panties on. He turned around and bent away from the mirror and took a picture. You could hardly tell he was a guy except for the bulge in the panties. His ass looked round and soft. Why was his dick hard? He hesitated but sent the picture anyway.
“Fuck you look good. Excited for tomorrow. I hope you’re ready.” Max stared at the phone as his mind raced. He had never had a job before and he wasn’t sure if any of this was normal. He wasn’t a super social person and didn’t have too many friends. He knew he couldn’t talk to his parents about this. And there was that feeling. The approval felt weird but he liked the attention he was getting from his coworkers.
Max didn’t sleep the rest of the night.
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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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