Well, here's my pitiful story!!!!
A long time ago, in a galaxy far, far away.. ( que the Star Wars Theme ) hehehehe
Actually, about 30 yrs ago, I think..... My Wife and I were invited to a family Halloween Party... we both couldn't think of a proper costume, until my wife suggested both of us cross dressed... What a novel idea, I thought. But, we had to hide her 36 D breast, and I had to figure out how to "grow" 38 D's...
I borrowed one of my wife's dresses, don't remember what I did for hair, panty hose and one of her bra's.... For stuffing, 2 pin cushions, minus the pins and needles of course.... For her, Ace Bandage wrap....A pair of nondescript womens pants, one of my shirts and ties. We tucked her more than shoulder length hair up into the hat as she wore it....
She applied some exaggerated makeup to my face. ( I looked like a hooker actually! LOL )
When I came out after fully dressed, my wife said I had prettier legs than she did ! I really doubted that, but gave her a thank you kiss. I was totally horrified and nervous for the first 45 mins at the party, but really got into it.
To this day.... I wonder if that really was the start of my crossdressing????