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A Beginner Goes Shopping

| Sep 2, 2019
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By Brittany Chambres
© 1996 TDForum and Brittany Chambres

Have you ever wanted to go shopping for lady’s clothes but were too afraid? This story is about my first experience buying clothes for myself in a lady’s clothing store. I hope it alleviates fears you may have about doing the same.


The first time I ever crossdressed was on Halloween. An event that started out quite innocently, turned out to be quite an enlightening experience, thanks to my wife’s spontaneity and wry sense of humor. It also turned out to be a turning point in my life. I found I couldn’t stop thinking about that night, and how dressing en-femme felt so natural.

The thought of being viewed and treated as a ‘Lady’ more than intrigued me. All of my life I had envied the clothes, makeup, hair styles, and activities that were considered taboo for me, simply because I was male. Deep inside, I wanted to wear the pretty dresses with patent shoes. For me, to have been a cheerleader instead of a football player would have been a dream come true.

A few weeks later I found myself wandering through the local mall, casually studying the ladies from afar. I longed to be ‘that attractive lady over there; the petite one with the cute, blonde, shoulder-length hair, slim skirt-suit, and three inch pumps’.’ Subconsciously I had made up my mind. If I could, I would. After all, hadn’t I passed once before already? My night out, en femme, on Halloween, brought forth the feelings I had always kept safely hidden away. It also made me realize the possibility that I could, in fact, be ‘that attractive lady over there’.

Before I realized it, I found myself browsing through ladies’ clothing stores. I was nervous. My hands were sweaty, and I kept thinking how everyone in the place was watching me. “Excuse me! What are you doing in here?”, I expected someone to ask. Who? I didn’t know, just someone. After all, I was a man and these were women’s clothing stores, filled with women’s clothes. What could I possibly want here? Men don’t buy female clothing! Or, do they? Sure they do, I realized. Men buy women’s clothing all of the time. They buy clothes for their wives, and I was married, wasn’t I.

I was still nervous as heck. At first, as I picked outfits off of the racks and held them up to look at, my hands shook. After some minutes, I became more absorbed in shopping. My hands calmed down and I started to feel more relaxed. Most female sales clerks, in spotting a young man out of ‘his’ environment, were kind and eager to help, although I meekly declined. I finally settled on a knee-length, navy blue, skirt-suit from one of the sales racks.

As I stood nervously at the sales counter, waiting to pay for the outfit, a young sales girl approached me.

“Did you find everything you needed today?” she smiled easily, “All of our accessories and hosiery are on sale.” Accessories? Hosiery? I looked down at the outfit in my hand. Some kind of belt would be nice I thought. And I would certainly need some hosiery to wear with the outfit. After all, it was a skirt-suit. That meant bare legs.

“What kind of hosiery would you recommend?” had slipped out of my mouth before I could stop my lips from moving.

“That depends on the color of shoes she’ll be wearing.” The clerk assumed I was buying the suit for someone. My mind raced. I hadn’t even thought of shoes.

“Navy pumps, I think.” Wasn’t that what ladies usually wore with suits and dresses?

“Well. . . I’d wear sheer white, if her office is casual, and sheer beige if it’s formal.”

“Oh, it’s formal. She’s an Executive Secretary.”

“Do you know what size she’ll need?” Again my mind raced. I wasn’t prepared for all of these questions about things of which I had no experience. I felt embarrassed. She pretended not to notice.

“No, not really.”

“How much does she weigh?”, she asked, turning one of the packages over in her hand. I tried to see the chart on the back, but didn’t want to be obvious.

“About one-fifty-five,” I responded, knowing full well that my wife only weighed one-oh-five.

“Here you go.” She handed me a package, “Is there anything else you need?” I told her I didn’t think so and thanked her.

Relief and excitement flooded my body as I strolled through the mall towards the exit. I had done it! I had bought my very own outfit. It might not fit just right, but I could always take it back. Couldn’t, I? I still needed some other items, like a wig, makeup, nail polish, jewelry…, but I had enough excitement for one day. I couldn’t wait to try on my new outfit!

The moral of this story is, if you haven’t bought clothes for yourself from a lady’s clothing store because you’re afraid, don’t be. No one is going to laugh at you. No one really cares! So, have fun. Go shopping!

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