My life as a woman

WARNING: This post is not for sensitive viewers and contains photos of a distressing, disquieting nature!

I was a cute baby, no question - chubby, with curly blonde hair, and gorgeous eyes. But the problem was that random strangers would often come up to my parents and fawn over their beautiful “daughter” – me!

Fortunately I grew out of that phase, and in no time was a strapping young lad (well, maybe more stringy than strapping). Unfortunately I had an older sister who liked to play dress-up with her little brother more than with her dollies - like when she dressed me in her teeny weenie red bikini. It was an easy fit, and posing like a lady, with the ever-present pout, came quite naturally. I responded to people’s shock and laughter and quite enjoyed the attention I received. And so it all started…

I was an actor at heart while growing up – possibly and probably because of my mother’s influence. In Grade 1 I took the role of Roo in Winnie the Pooh, and in Primary school I acted in all the annual school productions. Every holiday we children, as “The Natures Valley Amateur Dramatic Society”, would cobble together a play for our parents and next-door-neighbours and I was regularly given “normal” roles like the cow in Jack and the Beanstalk and the Beast in Beauty and the Beast. But finally, arriving at an all-boys’ high school I was presented with some unique challenges to have fun and to shock anew – by playing female roles in our school dramas. They weren’t big parts, but I relished them, and I didn’t mind that the other pupils mocked me and called me names. Grade 8 saw me acting as a fairy in A Midsummer Night’s Dream, while roles of the Player Queen in Hamlet and Potiphar’s Wife in the musical Joseph followed. What made them even funnier was that I was anything but effeminate.  Other roles, like when I was a policeman in The Pirates of Penzance just weren’t as much fun or as much of a challenge…

The sight of me chasing after Joseph singing, in the deepest voice I could muster, “Come and lie with me, love”, or doing a supposedly-seductive yet disturbing dance for Jacob’s son was, even if I admit it myself, hilarious. My “Hamlet” character was probably the most gratifying though. I laughed every time I had to get into my costume and have my makeup applied (firstly because of how people reacted) – the false eyelashes, false nails, real fishnet stockings … the whole toot. I even had my own pair of stockings at home. Our troupe was the comedy relief of the play, a lot of which came purely by chance. 

One evening I was running down a corridor to get to my stage entrance, slipped in my shoeless, stockinged feet and piled into a set of drums offstage to a loud “ke-rash”. Then, in one of the scenes the king was supposed to run up to me and jump into my arms. Unfortunately, when he did, he ripped my dress to the waist and left me standing sheepishly bearing my padded bra to a full audience… Finally, one evening we were making our entrance, as regally as possible, on a cart being pulled by some minions, when the cart’s wheel got jammed in a hole, flinging the king and I to the ground in a heap, me on top of him – all legs, dress and wig-askew.

I had a serious crush on the friend who helped
me out with this outfit. I don't think me dressing
like a woman helped my cause at all though.

As I grew older, virtually every fancy dress party I attended saw me go as a woman – once again because I was assured of a reaction. Everyone kept telling me what a stunning lady I made, what perfect legs I had, and how the outfits “brought out the colour of my eyes.” I guess that’s the beauty of mascara! There were two incidents that got me to stop, however. 

The first was at a New Year’s Eve party where another man told me that if I ever decided to cross the line, not just cross dress, he’d be waiting for me. The second was at a church party where one of my work colleagues thought I was a lady of the night. I still remember the horror on his face, as he backed up against a wall, seeing me rush towards him to give him a hug and a kiss on the cheek. He hadn’t recognized me at all! (He swears that he doesn't remember the incident.)

I did, however, come out of the cross-dressing closet one final time two years ago when I was asked to play “Oprah” at a classy ladies’ evening at church. And so I fished out the old stockings, had a deep cake of foundation plastered on my face and donned a fancy, frilly dress for my last big hurrah.(A quick aside - I didn't look at all like Oprah, but that didn't seem to matter. I still won one of the prizes on the evening, and everyone wanted to pose with me.)

My legs aren’t what they used to be, it’s getting harder to walk in high heeled shoes, and my hair has receded, but you never know, the old-age home setting is yet to be explored …

My "lady of the night" look, but wearing my brother-in-law's boots!

A just-discovered picture from Facebook: Me as "Oprah".
Yes, well, my interviewing style was pretty good, even if I didn't look like her.

My "Oprah" legs

"Oprah with "Ellen". It was the only wig we coud find at such short notice.
They should have just called me the "butch Indian-looking interviewer".