Early on, I used Halloween as an excuse to shop for my lady wardrobe.
"I'm going to a Halloween party dressed as a woman, so I need a... (fill in the blank with whatever I needed at the time: wig, bra, girdle, dress, high heels, makeup, purse, etc., etc., etc.)
I used that excuse a lot when I was still closeted. I dunno if I fooled any of the store staff with my Halloween story. Not many guys are going to spend $100 or more on a wig for one night, so something else must be going on.
At least once, I outed myself. I was 23 years old working in Kingston, New York, a couple of hours away from home and my stash of female finery. Halloween was coming up and I decided it was a perfect time to start my Kingston Kollection.
I found an old school lingerie store where I intended to buy an all-in-one. An older woman greeted me as I entered the store. I told her my Halloween story and added that I wanted an all-in-one.
That probably tipped my hand immediately; how many guys know what's an all-in-one.
The woman used a tape measure to take my measurements. Then she went in the back room and returned a few minutes later with two all-in-ones.
"Take these to the dressing room, try them on and call me so I can see if they fit properly."
I did not expect such a hands-on sale, but was glad to have it. I quickly stripped down to my briefs, zipped myself into my all-in-one and called for the saleswoman and by doing so, I tipped my hand again.
"Wow - that was quick," she remarked. (I assumed that her other male customers were not as fast as I when trying on their "first" all-in-one.)
She then checked me out and remarked that I had a real girlish figure. I tipped my hand again as my face turned beet red in embarrassment. Strike three --- I was out.
Couple gender exchange, Halloween 2011.