Cathy’s Story (Part Two)


Last year I told my story of how I became a practicing transvestite, it was published as Cathy’s Story. A lot has happened since then so I thought it was time for an update.

I have been very surprised with how quickly my ‘femme’ life has progressed. Perhaps the biggest surprise for me was a change of name. For reasons I’m not sure, of my daughter decided I had to drop my femme name of ‘Cathy Mann’ and she wanted me to be known as ‘Helene’. Her husband felt I should take things further and create a whole female character around ‘Helene’ and when I dressed up as a woman that I should get completely into the role; I had to completely believe I was female. I was a bit taken aback by these suggestions but a girl has to do what a girl has to do and so threw myself into becoming ‘Helene’ and it has been an incredibly fun and rewarding time.

I only began to dress as a woman in November 2000 at the age of 41 and now I can hardly believe or understand why I suppressed my desire to dress as a female. I truly believe I was a complete idiot not to dress up and I regret wasting over twenty years of my life denying I was a transvestite.

It was the discovery of the ‘Transformation’ web site that got me started as an active practicing transvestite as the opportunity to buy wigs, dresses, high heels and of course make up in a discrete manner was exactly what I required at that time. My biggest and most exciting discovery being silicone breast forms, these were beyond my wildest imaginings and I just had to buy some!

I have been learning with a passion how to dress and look female and now feel I am starting to get somewhere. It is not an easy process for the beginner but perseverance and practice eventually pay off, so if you feel you are not getting anywhere I can sympathise but stress you must endeavour with your efforts, it will work out for you, do not give up.

The process of transforming myself from a male into a female is incredible fun and so liberating. When I’m finally dressed as a woman wearing my make up and walking in heels I feel on a total high, it is the most sensational feeling and I adore looking and feeling this way.

My dream has always to pass as a convincing looking woman but I really believed I would never do more than dress up alone and in private. The big shock came in October 2001 when my daughter’s husband asked me when I would be going out as ‘Helene’. I had never considered this possibility, but the seed took hold and grew.



One evening in February 2002 I found myself walking out of the house and getting into my car experiencing a new sensation: my long hair was blowing in the breeze. ‘So what’ you may be thinking. Well as a man I’m bald but tonight I had long hair and what’s more tonight I was telling myself I was a woman. I had on full make up, I was wearing an elegant ladies trouser suit with a gorgeous ladies white shirt and I felt fantastic.

I started up my car and set off for an hour and half’s drive to meet for the first time other transvestites, people like me, I was both nervous and excited. I had learned of a coffee evening for transvestites and made the decision to attend. I was about to venture out of the house and into the public domain, it was very exciting.

I realised I could not park near the venue and I was faced with a long public walk from where I eventually parked. As I slipped out of the car and stood up in my heels on the windy February night I was thrilled and on a total high. I was about to walk for the first time in public dressed up as a woman! It was heady stuff.

As I walked down the street I had to pass several people and a few small groups and I was surprised not to draw any strange looks. I realised at that moment how much imagined paranoia we transvestites suffer, the reality was quite different. I began to think maybe I actually look okay and they just see me as a woman. I began to relax and thoroughly enjoy being a girl and must admit I felt a touch of disappointment when I arrived at the venue.

The night out was great and my confidence soared tremendously. I adored being out like this and chatting away with other T-girls, this was a dream come true. As with all good things the night came to an end and I set off back to my car. The pubs were emptying as I walked back and I noticed a few men looking at me when suddenly one fell in step with me and began to chat me up!!!!

Total panic ensued, I’m a man, I don’t want to get involved with men and he thinks I’m a woman, what do I do? I continued walking and didn’t say a word I just smiled a lot and realised I was actually enjoying this, it was so flattering. It was the ultimate transvestite compliment, he thought I was female! Eventually I reached my car smiled sweetly and gave him a wave and drove off. I wondered how he would have reacted if he discovered I was in reality a man dressed up? I think I was fortunate as things could have gone wrong for me. It taught me to be careful.

I have now been out dressed up as a woman on several occasions including a trip to Glasgow city centre during which I actually forgot I was a man! I have become so relaxed with being ‘Helene’ that I just think I’m a girl when I’m dressed ‘en femme’. Of course I only have to open my mouth and my voice is a total giveaway and I do need to refine my body language but I feel I improve all the time.

I have found that now I spend time appearing as a woman that my life is enriched and more fulfilled. I have unconsciously slipped into regular things many women do. For example I was getting fed up shaving my legs and I now have them waxed every three weeks. I was waiting for my appointment in a beauty salon when a work colleague arrived and she was very surprised to see me in there. Without thinking told her I was in for my eyebrow and leg waxing, she looked totally dumbstruck! I suddenly realised I was sitting in this big salon surrounded by beauticians and only female customers. She now knows I’m a transvestite but fortunately for me she is discrete, yet another warning for me I should take more care in the future with my secret.

I truly adore becoming a woman (albeit part time) it is such a fantastic experience and I would never give up being a transvestite. I feel privileged to have been born a transgendered person and that I can now experience life in both genders, I really do believe that transvestites are special people. It is so wonderful not to be constrained by conventional roles and of course dressing up is such fun. I for one would have it no other way.


Lots of love, Helene (Formerly Cathy) XX

Leave a Reply

Your email address will not be published. Required fields are marked *