I had hoped that you would use a bit more creativity than the “little black dress” but a classic is a classic for a reason and you wear it well! Properly styled, that long hair of yours is very feminine and your sister’s salon did amazing work with your makeup. Eddy, you pass! Any stranger would assume you were all girl.
Too bad for you, that tonight won’t be with strangers. I took the liberty of sending an email from your account to Mr. Delray, CC the staff and HR, that at tonight’s office mixer, you were tired of hiding so, you would be coming out tonight as your true self. Some replies were more supportive than others and HR has changed your pronouns, spelling and enrolled you in the company Gender-Transition program with free treatments!
You play the part tonight and I will consider our debt settled. Monday, you can tell them whatever you want, though I assume there will be severe consequences if you go back on your announcement. You may have to just have to go to work as Miss Eddie from now on.