(all characters are over 18)
Getting into your office wouldn’t be so hard: a question of picking the right pocket, an outward display of confidence and good timing is all it would take. I’m sure with some subtle inquisition I could gradually glean which is your desk. Ensuring you’d be wearing a skirt on the day in question, which would be critical to the surprise and my intentions, might be a little trickier without giving the game away. It could be resolved by giving you a standing order to wear only skirts on a Tuesday or maybe I’d make plans with you for after work and instruct you in what I want you to wear. Risky, the latter, because you might decide to change between work and play to be ever so slightly sluttier than you’d ever be in a professional setting, just to please me. A standing order it would have to be, with at least the fringe benefit of knowing that if I find you’re not obeying, I will have the pleasure of punishing you for it.