My Embarrassing Moments A shared journal of embarrassing pictures and stories from our awkward childhood to the present.

Pillory

I should never have made that bet. Feeling cocky about my extensive knowledge of sports, I bet my wife that our beloved hockey team, the Toronto Maple Leafs, would earn a place in last year’s playoffs. They didn’t, much to my surprise — and my wife’s delight. We often bet on things, and this time her twisted sense of humor got the better of me. First, I was ordered to go to the local Goodwill and buy a week’s worth of women’s clothes. Seven complete outfits were required — 4 dresses, 3 skirts and blouses, plus some bras, panties, pantyhose, heels, and nightgowns. Next, I was to construct a pillory in the backyard. From the photo, you can see what happened next: I was dressed each day in one of my new outfits and made to stand in this old-fashioned punishment device for four hours. Pictures were taken to document my wife’s “superiority”. Fortunately I too have a sense of humor, and I must confess that, despite the long hours in the pillory, living as a woman for a week was a lot of fun.

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