The Making of a nancy-boy. PART 1

I have been a transvestite since an early age.

I have gone though the typical phases of denial and the occasional purges. Originally it was avery private obsession. The thought of being seen by anyone dressed in womens's clothes was mortifying, but over time the urge to be seen dressed in womens' clothes became more and more compelling.

Originally costume parties provided a credible cover for dressing up publicly. But then I found a growing urge to go out fully dressed in broad daylight. I dressed as "normally" as I could. I sought to emulate a sexily elegant young, girl/woman my own age -sheer pantyhose, mid-thigh length skirt, matching blouse etc.( I will detail my first outing and the exhilaration of being out in the sunlight and in a crowded city store in sheer pantyhose, hot pants and suede boots, in a blog to be posted soon.) At that age I was quite passable. At first I thought the stares and smiles I attracted were because I had been read. I soon realised that they were mainly interested males who seemingly liked what they saw.

As time went on, going out in public and passing was not enough.

I was hooked on the danger, the shame the humiliation. I waned people to know I was a transvestite; a crossdresser; a faggot; a sissy; a nancy boy. I even quietly fantasized about being pointed at and being called such names in crowded public places.

After a short-lived marriage I began to regularly wear pantyhose or stockings with women's panties under my male clothes. Frequently, on weekends and at nights I would go out in public with my sheer , stockinged ankles showing under my trouser legs. I eventually added a diamante anklet.

Just walking around normally did not attract the attention I wanted. I bought myself some low cut loafers to show off more of my stockinged feet. I would sit my self in very public view in shopping centres and at bars so that my trousers would ride up to display my ankles and much of my calf.

With my heart in my mouth and my groin in a high state of agitation I would sit there with the light shimmering off my stockinged ankle and my anklet glimmering brightly as it delicately adorned my rather shapely ankle . It was quite a contrast to my otherwise masculine appearance. I started to get the second takes, the stares, and the smirks I craved. It was exhilarating, but I was prisoner to a very powerful urge to take more and more risk.

I came to add light pink nail polish and light eye make-up and lipstick. I would on occasion wear a bra that would be visible through a thin shirt or reveal a strap through the shoulder of a t-shirt.

I bought women's slacks which were more tapered to more elegantly allow a glimpse of ankle and many, delightfully zipped or buttoned up at the side or the back. I then progressed to adding some low-cut womens loafer or elegant pumps with 1/2 inch kitten heels that showed off the shimmering tan pantyhose that adorned my feet and toes.

What I aimed for was an androgynous balance that was stylish and elegant rather than comical or grotesque. In a rather strange incongruity, perhaps rather indicative of my own ambiguity, I wanted to be stared at and sniggered at but I also wanted people to think I was elegantly presented. I wanted them to be challenged by the incongruity of a boy/young man dressed in elegant female clothes that a young woman of his age would wear, rather than visually offended by some garish get-up that was not only effeminate, but would look ridiculous on anyone, regardless of gender. The idea was to have people privately admire my sartorial aesthetics, whilst at the same time have their gender sensibilities confronted by an obvious male, effeminately presented.

Overhearing the odd whisper - "Look! That guy's wearing stockings" or "He's wearing a bra" would cause me to blush with shame and vulnerability , yet also arouse feelings of excitement and delightful girliness.

But it wasn't enough ....

To be continued