Once Penny realized that her desires lead her to dressing as the opposite Gender, it did not take long for Penny to make the start to Transform.
Once on hormones, Penny did not look back and adapted to her new gender with ease. After a few surgical procedures to enhance her mind, body and soul, Penny embarked on starting her new life and, career.
Penny did not view herself as a Woman or a Man, but simply like to be called “a happy person”, if someone tried to categorize her gender.
Penny started her career in the 80s, winning many talent contests on the drag strip, especially contests at Flo’s Palace and Balmain Town Hall Hotel.
From there she moved to being a full time showgirl at Patch’s Nightclub on Oxford Street in Sydney where she stayed happily for over 7 years as part of a dream team of stars, including, Trixie Lamont, Maggie Bums, Poala Negri, Jay Jay Bailey and many more.
Penny was then asked to join the 5 time Mo Award winning show ‘Simone & Monique’s Playgirls Revue’ (Very Las Vegas) and happily jumped at the chance to Tour Australia and beyond, in straight clubs and casinos, where she stayed for many years, developing and learning, many crafts not only on stage, but behind in organization and management.
Growing weary of living out of a suitcase, Penny started a show called “Raw Images’ with 2 fabulous talents, Ashley Swift & Anton Scott, and based in Sydney, took over the gay scene for a few years working 6 shows a week for over 3 years, and with some cast changes over the years, the show toured Sydney and Country venues and was very popular.
During this time Penny started working a Day Job for a newspaper called the ‘Village Voice’ which got her involved in an awards night called ‘The Caps Awards’ held at Paddington RSL Club hosted by Miss Rose Jackson. The awards had been organized by other people, the year before by David Dot Wilkins, but this year it was Penny’s turn.
After the success of that year, Penny, Ian and Dot (Diva Founding Members) got to together and The Diva Awards was born! (Drag Industry Variety Awards)
The Diva Awards became the night of the year, that everyone looked forward to, and the small team of 3 turned into a much larger and successful team over the years.
Penny, during the course of Diva growing, became one of the Managers at DCM Hotel, one of the most popular Nightspots on Oxford Street for many, many years. Penny stayed at DCM for over 10 years, and during this time, helped to raise much needed funds for Ward 17 South, the Aids Ward at St Vincent’s Hospital, and through star studded shows held annually at DCM over $100,000 was raised. Penny also performed at many other functions and charity nights and even competed for 5 years at Xtreme Nightclub and very popular multi gender Strip club.
Penny was just at home on stage as off, and organized many theme parties, events and functions over the years, including the Diva Award winning Drag Extravaganza, “Decades of Drag” a 4 week “This is your Life” style concept held at the Taylor Square Hotel.
After 10 years at both DCM Hotel and The Diva Awards, Penny, had a “Sea change” of her own and left both companies and returned to the stage on a more full time basis in Carlotta’s Priscilla Show, now known as Carlotta’s World Famous Les Girls. Still with this show today, Penny didn’t rest there but put her managerial and organizational skills to the test once more, with Unique Entertainment, An Artists Management Company, looking after Carlotta and singers such as Melissa Tkautz and Keren Minshull.
From there it was only a short jump to a Music Producer and now Penny is a Director of JRB Music, with Melissa Tkautz about to release her new single with JRB Music and Album. And as of this bio being written Melissa’s single ‘Glamorous Life’ debuted in its first week on the ARIA Club Charts at the number 34 position.
Penny, now an Aria Member and Voter, looks forward to expanding JRB Music with more local talent. As well as this, Penny is also on the Board for the Sydney Gay and Lesbian Mardi Gras and manages and performs in Carlotta’s Priscilla Show.
Penny is very proud of herself, where she started from, and where she grew too, and feels that her personal journey still has a long way to go, but hopefully that in the years to come she will experience many new and exciting parts of life!
This article was originally published in Transformation Magazine 61
One thought on “Penny Clifford’s Transformation”
Hi Penny, I have to agree with Charlotte Deneeice Windham that you are no doubt drop dead gorgious. I personally have not, at this time started my transformation and I use a femme name. the bodice you are wearing in your picture abbsolutely makes you look so femmine. Your breasts are nice and the fishnet stockings are fabulous. My real name is Bob, I live on the East Coast, and yes Charlotte to heck with all those close minded people who don’t understand. They will never get it and I don’t waste my breath trying to explain it to them. Penny & Charlotte Keep On Kepping on ladies. Hooray for Us & the heck with all the others.
Comments are closed.