It was a typical Halloween night when my ex-husband and I were debating if we should go out dressed for Halloween at the local bars. Halloween has always been one of my favorite holidays because it was a chance for grown-ups to play as children without being criticized.
Most of my previous boyfriends were just not into dressing for Halloween, so when my ex suggested we do it, I was thrilled! We started talking about what we should be dressed as since it was Halloween night and we didn’t have time to go to a costume store and would have to make do with what we had in the house.
I thought since my ex was into music having been in a teen band as a drummer that he would want to dress as a rock star or Willie Nelson since he played an amazing rendition of “Angel Flying Too Close to the Ground.” I started looking around for a red bandanna when he stopped me and said, “What about if I dress as a woman?”
Taken aback by this he saw that confused look on my face, and went on to say, “I dressed as a woman a few years ago on Halloween with Sharon (his ex-wife) and we went out to Butch McGuire’s pub. It was so much fun.” The thought never crossed my mind since my husband was all “man” and usually more interested in talking about real estate than woman’s shoes.
Yet, he looked so excited by the thought of doing this with me; I said “Yes, let’s do it! But where do we get clothes big enough for you to wear?” I was a size two. Certainly this man who stood over 6 feet tall and weighed 180 pounds would not be able to squeeze into my clothing!
Minutes later he came downstairs with a black knit skirt, white lace top, black stilettos and a Marilyn Monroe looking platinum blond wig. He told me he kept these items from the last time he dressed for Halloween. In front of me my husband quickly changed into these clothes and asked if I would get my make-up bag and do his face.
I first went into the kitchen and poured myself a vodka martini. We went into the bathroom and I applied a full-coverage base to hide his beard. Lots of concealer and dark green eye shadow to make his hazel eyes pop. I have always loved make-up, so it was easy for me. Yet, putting makeup on my husband who was enjoying it more than I ever have was confusing for me.
We both drank a pitcher of martinis as we transformed him into a woman. We never made it out to the bar. Instead we got drunk, and made love in front of the fireplace listening to Prince’s song Kiss. Coddled in one another’s arms, I just knew my ex liked dressing as a woman, but had never met or thought about him being a cross-dresser. I had had no experience in my life with this and nor did he identify himself as one.
Yet, in looking back this was the start of him coming out and testing me to see if I would like it. Honestly, it was scary for me. This was mostly, because his cross-dressing just came out of nowhere after being together for two years. I have learned that this is not an unusual time for a cross-dresser to come out. Halloween is a very popular time to do a reveal even if it is not defined as cross-dressing.