What Ever Happened To Kay?

| Jul 23, 2018

The world of crossdressing and transgender is a transitory one. As we start to come out we change at a rapid pace. We change who we are and as we move around we also meet new people. Sometimes they become our friends. Sometimes they come briefly into our lives and then disappear without a trace.

Of the latter type for me was ‘Kay.’ Kay was probably the most confident, competent and outspoken crossdresser I’ve ever met. She was also one of the first people I met when I went to my first TV party. Her immaculate hair, nails and makeup, her confident air and her gorgeous clothes marked Kay as a special person.

It was about 1982 that I discovered the world of heterosexual crossdressers. Before then I thought my affinity for women’s clothing was shared only with outrageous drag queens, female impersonators or transsexuals like Christine Jorgenson or Roberta Cowell. However, by a serendipitous series of events I found out about a Joyce Dewhurst party being held in Queens, New York for crossdressers and their friends. I just had to go and I wasn’t going to let the fact that it was going to be held in hot, humid July deter me. Three memories stand out about that weekend in New York:

  1. Not many crossdressers go to parties in July.
  2. New York’s heat, humidity and one’s tendency to sweat under a wig will play havoc with one’s makeup.
  3. I met Kay.

The first two facts were enough to drive me back into the closet. However Kay made the weekend for me. Never had I met someone so outgoing and so full of facts and hints about dressing and passing and so confident about who she was. It seems she’d been everywhere and been there in drag. Kay was from California but traveled often to the Far East and to the east coast on business and when she traveled she always seemed to be able to fit in a little R&R en femme. Despite a very masculine business life Kay was a gorgeous woman at night.

Kay was very much into experiencing things and retelling those experiences – whether it was shopping for shoes or visiting a nightclub – to others. That first night at the Joyce Dewhurst party we talked a lot. Kay convinced me not to be afraid of being dressed in public — everyone is entitled to their own space and while some may read you very few will make an issue of it especially in cities like New York. (It may be different in Butte, Montana or some other town where everybody likes to know everybody else’s business.) I learned many things from Kay that weekend and later by reading her articles, “Kay’s Way,” in Transvestian and other publications. For instance, when I complained about having to wear two pairs of pantyhose to cover leg hair Kay told how she convinced her family that shaving her legs would reduce the effects of mosquito bites. Kay also had an effective way to get to try on women’s clothes in a store even when she was dressed as a male. She carried photos of herself en femme to show the store clerk as she would claim to be a female impersonator looking for a new outfit for a show or a pageant. That would reassure the clerk that she wasn’t dealing with some weirdo about to masturbate into one of their $1,000 gowns. Apparently they were sometimes thrilled with the idea that one of their outfits might be used on stage. I have since occasionally used the pageant idea myself.

That first weekend in New York, Kay took me to a Tri-Ess chapter meeting at Muriel Olive’s boutique and to a S&M club called Club ‘O’ somewhere in the bowels of Manhattan’s factory district. Access to the club was past a couple of burly guards and up a freight elevator. I had never been to anything like Club ‘O’ and I wasn’t really excited by it. There were a few domina queens in their black leather outfits and many men walking around in their underwear asking to be whipped. You could oblige or not and I was a ‘not’ but Kay was quite into it and was determined to find a slave to lick her shoes and feet — no problem. Although it didn’t seem to be a sexual turn-on for her, Kay seemed to really enjoy manipulating her ‘slave.’

We finished the evening at an after-hours club called “Hellfire.” Those who knew it will not be surprised that it was too much for this virgin’s senses and I left Kay there to return to my hotel and get a short sleep before my flight home. I never saw Kay again but we wrote to each other for a while and her articles continued to influence my life as I vicariously enjoyed her adventures in Washington, Pittsburgh and elsewhere. I also enjoyed her reports on various TV conventions and weekends. Then I stopped seeing her articles and her photos no longer appeared alongside stories of TV gatherings and her ad was no longer in magazines. Whatever happened to Kay? One person who used to know her said she thought Kay had been found out by her wife and a messy divorce ensued which destroyed Kay’s business and left her unable to pursue her hobby. But this person didn’t know for sure what had happened to Kay. If you see her say Linda says ‘hello’ and thanks for the memories.

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Category: Fun & Entertainment

About the Author ()

Canadian writer Linda Jensen is a long time contributor to TGForum. Before the days of the Internet Linda started her writing with the Transvestian newspaper. Her writing ranges from factual accounts of her adventures to fiction although frankly sometimes her real life adventures are stranger than the fiction. Linda is married to a loving partner who upon learning about Linda said, "she was part of you before I met you. Although I didn't know it she was part of the package I fell in love with. I don't want to mess up that package." "Does it get any better than that?" asks Linda.

Comments (1)

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  1. Tasi Zuriack says:

    The sadness in this story is that it’s repeated many times over. Friends that suddenly disappear for no obvious reason. There are way too many