Personal Assistant Roleplay: The Perfect Sissy Secretary
The corporate world is all about power. There are Bosses, and there are Assistants.
The “Personal Assistant” fantasy is incredibly popular because it combines intellectual submission with physical objectification. You aren’t just a toy; you are a useful, efficient, and well-dressed employee who also happens to be totally available for the Boss’s pleasure.
Your job is simple: Make the Boss’s life easier, keep his calendar full, and keep his stress levels low (by any means necessary).
The Office Dress Code
To be a good secretary, you have to look professional… mostly.
- The Pencil Skirt: This is non-negotiable. It should be tight enough that you have to take small steps. It forces a wiggle in your walk.
- The Blouse: Silk or satin. Buttoned up just enough to look decent, but easy to unbutton if the Boss demands it.
- The Glasses: Even if you have perfect vision, wear them. The “naughty librarian/secretary” look isn’t complete without peering over the rim of your glasses.
- The Heels: You need to hear that click-clack-click sound when you walk down the hallway. It announces that the help has arrived.
The Job Description (3 Scenarios)
1. Taking Dictation (Kneeling) Most assistants sit in a chair. Sissy assistants know their place is lower.
- The Task: The Boss needs to send an email. He dictates it to you out loud.
- The Twist: You don’t sit at a desk. You kneel beside his chair with your notepad. You must write everything down perfectly while looking up at him attentively.
2. The Coffee Run It sounds cliché, but service is service.
- The Task: Making the perfect cup of coffee is an art.
- The Twist: You must serve it with a specific phrase: “Here is your coffee, Sir. Is there anything else you need me to take care of?” The answer is usually you.
3. “Working Late” (Overtime) The office is empty. The lights are dim. It’s just you and the Boss.
- The Task: You have to file paperwork or organize the bookshelf.
- The Twist: Since no one is around, the dress code relaxes. Maybe the skirt comes off, but the heels stay on. You are “earning your bonus.”
The Mindset: Efficient & Eager
A bratty sissy doesn’t work well here. A Personal Assistant must be competent.
- Anticipate Needs: Don’t wait to be asked. If his water glass is empty, fill it. If his shoes look dirty, clean them.
- Silence: When the Boss is on the phone, you are a statue. You do not make a sound, even if you are under his desk.
📝 Your Task for Today
The “Daily Agenda” Drafting.
You are going to plan the Boss’s day.
- Open a document or get a notepad.
- Write out a schedule from 9:00 AM to 5:00 PM.
- Mix business with pleasure.
Example Schedule:
- 09:00 AM: Review quarterly reports.
- 10:30 AM: Oral inspection of Assistant.
- 12:00 PM: Lunch meeting with Client.
- 02:00 PM: Assistant stands in corner for posture training.
- 04:00 PM: Sign contracts.
Print this schedule (or save it) and post it on your wall. That is your day now.