Failed!

A Facebook group I am part of recently put up a plea for stories of crossdressing success stories, I opined that I thought my failures would make more interesting stories, so of course I was challenged to tell more.

January 2012

Until the last year or so I was a cross dresser all my life, even before I knew that there were such things, a bit like music and gardening I cannot remember a time when this wasn't a factor in my life.  I have only stopped crossdressing since embracing the concept that I am indeed a woman, but the recipe went a bit wrong and I ended up looking like a man.   I no longer cross dress, I just dress in a gender appropriate (if not always age appropriate) manner for the woman I am.   But of course this was not always the way!

Until I was already quite old all my cross dressing activities were pretty furtive, I was very much in the closet only dressing at home when no one else was around, or indulging in those ridiculously dangerous late night walks thinking that no one would see me, without realising that if anyone did see me they were exactly the ones I didn't want to be seen by.   It was only when I got to 50 that I realised that this was not going to go away, and that I needed to explore what this was all about.

November 2014

I had a stash of clothes and a little makeup, so around my 50th birthday I had my first proper outing, I remember I wore some very nice baggy white linen trousers, canvas slip on shoes, a blue top with spaghetti straps under a white linen shirt top which I wore open. I teamed all this with a white canvas over the shoulder satchel.   It is a nice summer outfit, and I still wear it on occasion (when we actually have a summer) the only trouble on this occasion is that I still wore a beard! In my defense I will say I was trying to work out if androgyny was an option, but it was more a question that my beard had become part of my self identification as man.   I was aware that I was getting a few looks but decided to ride them out and enjoy myself. It was only towards the end of my outing that I heard a small child ask her Mother "Why has that woman got a beard?" that I realised just how wrong,or maybe how right I had got my presentation.

French Trip 2011

It must have been a couple of years later when I had removed the beard but had still not gone out in public wearing a dress and heels, I decided that my first proper outing would be a small shopping trip, to a center not too far away.   I drove down, getting changed in the car, even having gone to a different county I was still terrified of being recognised, so by way of disguise I decided to walk around without my glasses on, great idea, except that I kept drawing attention to myself by bumping into things!

I have had some bad wigs and some bad outfits, but the photographic evidence has long been destroyed!

On another occasion I found I had the house to myself for a a few days and nights, so of course I dressed, I also decided to go out and see a play at a local art house theater we still had then.   It was a very good play, apart from two distractions, a member of my band was in the cast, and my dress was a little shorter than I realised so my stocking tops kept showing. Neither spoiled my evening though!

I think one of my most worrying moments though was when I was posing for a photo shoot to advertise some concerts, I was wearing the most gorgeous black backless evening gown, the cut of the gown simply will not allow any form of bra, so I had to rely on double sided tape to hold the girls in place.   The problem came as the lights got hotter and I started to "glow" the tape gave up on the unequal struggle and my boobs slowly started to descend towards my waist

I have of course experienced the wardrobe failures that we all encounter, the stay up stockings that don't, zips which refuse to stay fastened, and on one occasion a broken heel.   But these are just dressing failures not cross dressing failures.