By accident, of course!
I managed to pull this stunt last week, on a busy day with both a therapy session and electrolysis. I'm afraid I made a poor bank teller very uncomfortable.
Background: I'm part time so far, and haven't done the legal name and gender change yet. So, I obviously have ID that doesn't look like me. However, I almost always go out to my appointments as me rather than in male drag.
I had an electrolysis session that day, and had been growing a nice crop of hair clumps for Jodie to pick through and zap. Earlier in the day, I had a therapy session. Both are in the same town, an hour's drive from home, and I had them scheduled about 90 minutes apart. I knew I wouldn't be driving home between them, so I brought along all the stuff I usually use prior to electrolysis, the numbing gel, analgesics, and plastic wrap to cover the gel.
I finished up in therapy, and presented my hairy self at a food kiosk to grab a decaf and a little breakfast roll. Then I munched away while dealing with the day's e-mail. A little under an hour before the appointment, I headed to the car, slathered on my gel, applied the wrap to keep it from evaporating or drying, and took the analgesic. Then, I noticed that I didn't have my checkbook. Oops.
Now, I'm sure I could have just told Jodie and paid her later, but that always bothers me a little because I know businesses often depend on prompt payment. Out with the iGadget, and find the nearest bank. Hey, a branch of my bank is nearby! I can just get the cash out of the ATM, no fees, and everybody's happy. Brilliant!
So, I head to the bank, duck out of the car and up to the ATM in the lobby. "Out of Service" Huh? Out of frigging service? Uh oh. Inside the bank, a teller notices someone dithering at the ATM, and he buzzes open the door and motions me in. Oy.
So, here I am, skinny jeans, bodycon light turtleneck (in teal), 10" ginger blonde wig, purse, and plastic and gel over much of my face below the wig and eyes. I walk toward the teller. He looks up. His eyes get ever so round. The teller next to him glances up, and she stares, shifting to the far side of her window. Uh oh. I suspect they were thinking something other than "Trans!"
I say that I'd like to make a withdrawal, the cash to cover the electrolysis. He takes the card, swipes it, and says "Uh, I need to see some ID." OK, here's my wildly out of date but valid license, showing a round maleish person, weight 190, crew cut. He looks at the femaleish 140 pound person with the unruly ginger blonde hair. "Oh, I really should update the license. There have been some changes." He replies "Oh, I see... it's you." I get a quick count of the cash and a recept, and get the heck out of there before I scare a customer.
At least they had something interesting to talk about on their lunch break.

So, how's your day going? Surprise anyone recently?