Dressing to Express

 

by Bobette

The classified ad read as follows:

"Petite, attractive lifestyle Mistress seeks soul mate for relationship, possible/LT commitment. You must be single, unencumbered, 45-65, healthy white male, who enjoys and is experienced in c-d and domestic duties."

I had recently become single and was living alone once again. I was interested in meeting new people and having fun, new experiences when I came across this ad in a local alternative newspaper. This ad seemed far more straightforward and exciting than the usual call for someone to share moonlight walks on the beach, soft music, and candlelight dinners. Housework seemed a lot more authentic.

I called the number in the ad and after some back and forth conversations on the phone, earned an interview and thus began a journey, that for the first time, formally led me into the experience of cross-dressing, something I had really never done before. Unlike many others who are attracted to cross-dressing early in life, I never really was. I am of mature age and before responding to this ad, had only mildly flirted with "dressing."

However, at the time I read the ad I was consciously exploring a number of issues having to do with relationships, the roles we play, some of the social constructs of masculinity and femininity, including how we dress, to whom we are attracted and why, and so forth.

Five hundred men answered her ad. She interviewed about 100 of them, and out of all that, I was the lucky one to be chosen to become her personal servant.

It would take volumes to relate all the experiences I had after I started my training and duties with Mistress. Mostly it was good clean fun, housework, dressing up, entertaining, constructing scenes and going out and doing things together. However, the dressing-up was a core part ofthe experience, and something that has stayed with me ever since.

I dedicated weekends to being at her house, an arrangement that lasted for months and months. I was assigned regular chores, which I took on faithfully and in good spirit, and soon thereafter, she began to introduce me to "dressing."

One Saturday afternoon, early on, Mistress took me shopping. We went to Savers, a used clothing store on the west side with an enormous selection of low priced clothes. Once there, she selected, and I tried on, hundreds of articles of clothing. (Very frankly, she was so excited about the shopping I thought she was going to "lose it"). We honed down our discoveries to about 40 items, which we bought, at a total cost of only about $90; great bargains, I thought. She said this would become my basic wardrobe and that we would build upon that.

Later, back at the house, I learned that she was a master at the art of dressing someone up, as she outfitted me in first one thing, then another. She did my make-up and my nails. Then once dressed, I was absolutely amazed at the transformation of myself in the mirror. I could hardly believe my eyes. I had no idea I made such a pretty and believable girl. I discovered I would be absolutely thrilled to date myself!

Together, we constructed a variety of outfits for different occasions. We created several formal but very sexy outfits for evenings out. Then we created several other looks for more intimate "stay at home" entertaining or occasions. Then I had several more outfits for at home, when working on my chores, and housekeeping duties.

More than once we would go out to lunch or dinner together with me in drag, something I had never contemplated doing. Then, some evenings, we would dress and go out clubbing at one or more of the alternative nightspots along the Central corridor; mostly places which were open and tolerant of alternative lifestyles. Of course, I was absolutely amazed at people's acceptance of me "dressed". I discovered how easily I could "pass." On many occasions, I got nice "looks" and compliments. All of this really built my confidence.

I leave the Valley during the hottest months of summer, so our experiences finally ended, but we left the best of friends and I am still in touch with my former Mistress. However, I continued to enjoy the experience of shopping for outfits and accessories and "dressing" at every reasonable opportunity. Most of the summer I spent assembling clothes for a "cowgirl outfit," or otherwise, simple denim look. It's a look that I think is playful, flexible, fits my personality, and is a good look for here in the southwest. Of course, I do have other "looks" I am working on to express myself, in other ways, through dressing.

What exactly it is that attracts me to dressing, I can't say. Perhaps it's my androgynous nature wanting to express itself and dressing enables that. I do like the look and feel of the different outfits, and the colors and combinations one can come up with. I also like the actual "getting dressed" experience, but then I also really like the "theater" that's involved in going out. I just wish our society could accept us "special characters" more easily. I've learned that where most are quite tolerant and accepting, some don't quite get it. On the other hand, I've decided that dressing is a rather esoteric art form anyway, and as such, is an activity perhaps truly only meant to be understood and appreciated by a few.

However long my interest in dressing continues, I work on improving my image and continue to seek creative venues for my fun new hobby and personal expression.

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