You: just a skinny little straight boy with a baby face, looking to break into the industry. You managed to grab this personal assistant job and have been extremely excited and eager. You’d do anything to please but noticed that I’ve become less impressed lately. I’ve been more critical of your work lately and that has really been getting to you. You’ve even stepped up your game and improve each day but it never seems to be good enough. Yet, you still keep trying to please.

I pull you into my office late one night and it starts as usual. You standing nervously in front of my desk, asking how you can help me. I look you right in the eyes, “This just isn’t working out. You are not performing to the standard of what I need in an assistant.” You grow terrified at what will come next. Your legs start shaking out of fear…”I’m gonna have to let you go.” I see how devastated you are as tears start rolling down. You pause for a moment to take it in then suddenly drop to your knees, begging for another chance.

I walk around the desk and stand over you. I wipe the tears from your eyes, “What am I going to do with you. So much potential…” you stay on your knees hoping I will change my mind.

“I’ll tell you what…I thought you had embarrassed yourself enough prior to today, but this shows me how much more you are willing to embarrass yourself. You need discipline. Maybe a little more embarrassment will help with that.”

I lift your head by your chin and look you right in the eyes, “do you understand?” You shake your head no, showing a sense of fear all over your face. “You want the job back, it will cost you. For the next week, if you come back to work, you come dressed as a woman. I will inspect you every morning to make sure you actually look put together. Then show me you can do the actual job.”

I walk back to my chair with a smirk, thinking you’ll never do it…until the next morning when you come to my office, completely dressed like a woman with makeup, wig and all. Now I see how much you really will do for me and that I can push our boundaries even more.

If this excites you, please message or DM me. Maybe if it goes well we can make this a long term thing. I personally like to get right into the RP. When you message me, describe what you will look like and what you wore your first day along with any limits I should know. To make it more exciting, I will be at work while we talk.