One Mardi Gras in New Orleans, my wife Pam and I had just parked under a bridge and we were getting out of the car to walk the 15 or 20 blocks to a good spot to watch a parade on Canal Street. I'd finished off half a bottle of bourbon on the way from our motel in the suburbs. On an impulse Pam talked me into a wearing a skimpy, feminine costume that she put together almost randomly in a few minutes by going through her suitcase in the trunk.
Pam had me get in the back seat, remove my clothes and put on totally sheer black pantyhose. It was cold, so I needed long sleeves up top to stay warm. Pam pulled out a stretchy light colored shirt or sweater that was skin tight on me when I put it on and barely came down to the top of my pantyhose. Then Pam gave me a piece of her lingerie that I liked on her. It looked like a faux leather one piece swimsuit in front. It was black, very stretchy, with high cut legs and a thong back. I was barely able to squeeze into it. The crotch was so tight that it almost forced my cock and balls up inside me. It flattened me out enough to give me a feminine look in front. In the back, the thong strap pulled my pantyhose tightly up between my butt cheeks. "I feel naked in back," I told Pam as I patted my strangely flat front.
She looked at me. "You look cute in front. Turn around...Yea, you do look naked in back. Nice ass, though. Come here." She put bright red lipstick on my lips and applied some other make up to my face. I knew I looked ridiculous, but I was too drunk to care or remember much at first. Walking the streets for hours I did get a lot of laughs and comments, some cat calls, and a few insults, but mostly laughter and I laughed along with all of it.
Mardi Gras is so strange that I didn't draw nearly as much attention as a lot of the even more oddly or skimpily dressed people. I was far from the only cross dresser. Many were obvious and ridiculous like me, some made you wonder, and some were perfectly passable trans-women or just sexy women, no way to know which. Bare skin was everywhere, male and female, so I eventually got used to wearing my skimpy costume. The cops will let almost anything short of total nudity go on that one weird day of the year. If I dressed the same way on Wednesday I'd probably end up in jail.