The Office Swap

A Sexual Fantasy

— By bill

I've always been attracted to my executive assistant, and I suspected the feeling was mutual. But it's always felt too inappropriate to act on, given the power dynamics at play. Then one night while working late together on a project, I slip up and admit how I feel. She lights up, pleased I finally said it, but asks what took so long. I explain my reservations, which she understands. She thinks for a moment and then giggles at the solution she's come up with: we will swap clothes and act as if she is the boss and I am the assistant, and then it will be acceptable for us to get together for the night. I am surprised by how excited I am at the possibility of seeing her in my suit, and we quickly undress and help each other into our switched outfits. I help her tie her tie, while she applies my makeup. I show her how to sit and stand like a man, while she helps me walk in heels. We both love how each other looks dressed like this. She gives me instructions like she is the boss, and I do everything she tells me to. Eventually, we transition into less professional behavior together. She continues to give the orders about what we will do, and I continue to enthusiastically follow her commands. Eventually, she decides that the only way to properly complete this role reversal is for her to peg me. There is suddenly nothing I want more than this. She puts on a strap-on and has her way with me. Afterwards, we decide that we need to keep this a secret from our colleagues, but also that we're going to keep on swapping whenever we want to do more than just work together.