Why and When did I start Crossdressing

My earliest memories of cross dressing are circa primary school days. There was a trunk full of women’s clothes in the garage of our home; I seem to remember enjoying getting the dresses out and putting them on. My Mother also had an old pair of bathers in our laundry and when she was not home, I’d go in there and try them on. “Worse still!!!” about that time, I found an encyclopedia article on women’s period dress quite fascinating, so I guess my love of wearing these clothes stems from that time.

I can also clearly recall how beautiful my Mum looked when she and my father were attending a formal ball; I guess I wanted to look like her--all beautifully coiffed, perfumed, made up, and dressed in a long evening gown. (Perhaps that’s where my ongoing love of formal wear came from too!!)

Moving to my early teens, my parents had a holiday cottage where, (though it would never be allowed these days), I refused to go for winter weekends, as there was “nothing to do”. So this gave me the chance to be on my own and dress in all my mother’s finery. (Tennis balls had to make do for breasts in one of her bras… But that was OK). I especially enjoyed the tightness of her panty girdles and feeling the tautness of the attached suspenders to her stockings.

This went on for some time, until, inevitably some relatives called in to check on me one night and I was well and truly “Sprung”. Being a typical “father of the age”, i.e. the 60’s, my father’s “severe talking to” about this “hobby” of mine, centered on the retribution I would face when I got older if the “boys in the pub” found out about my penchant for things feminine!!

I attended a trade oriented, all male high school where drama and plays were hardly given a mention. So it can only be imagined how jealous I was when I read a newspaper article about how in the best tradition of all male private schools of the era, boys were selected to play the female roles in the school’s annual production. Males playing “Lady Bracknell” in the “Importance of Being Earnest” have had me green with envy ever since!!!!

Onwards into my 20’s and once married, I assumed “this will all fade away”. But of course, it did not, and the need to be Caty caused much tension in the marriage. It was eventually one of the main reasons for the divorce. My career involved a lot of interstate and overseas travel so that’s when Caty would appear, mostly in a hotel room somewhere. She did venture out occasionally, in such places far from home as London and Toronto, and she attended a couple of CD group meetings in Perth WA. Caty has been retired for quite some time now, and the location where she lives and the circumstances of that location, plus her current relationship, allows her reasonably frequent occasions to “emerge”. Period and evening gowns are still favorites, as is classy cocktail wear and lingerie. Having two girls did not help, because when they matured, there were even more “frillies” about the house!

Caty would love to go out in public more often, but not in the small rural community where she resides. The gossip mill would go into meltdown if she was “sprung” and whilst she may be able to withstand all of the above, the burden on her beloved partner would be most unfair!

Furthermore, Caty knows that one day, (hopefully quite some time away), “advancing years” will decree a move to a retirement village back in the City. How this will affect not only her, but her clothes, make up, jewelry, when to wear and how to storage it all remains to be seen.

Happy dressing everyone…

DECEMBER 2018 UPDATE

Time has rolled by and now at past “3 score and 10”, Caty is very likely to end up in a retirement village soon. This will be most beneficial for her “male half” and “his” beloved, but could be a bit restrictive for Caty.

The saving grace is the storage unit about a half hours drive from the above and the need to do reasonably frequent overnight “charity business” trips. The charity she volunteers for is a two hour drive from here, hence the overnight stays.

Public trips out shopping and going out to dinner are very infrequent, but are treasured when they can occur.