Outline: A mainly factual auto-biographical account of my fascination with womens' clothes and crossdressing, and how, what I once thought was a harmless, clandestine kink transformed into a world of intense public humiliation, self humiliation, sexual submission and, ultimately, my irreversible transition to extreme submissive transvestite homosexuality.

I first tried on womens' clothes at the age of 9 — I remember it as clear as if it were yesterday. A pair of sheer tan stockings attached to a tight satin girdle and a bra — I loved the look; the exciting feel of the stockings on my legs: the tightness of the shiny corset around my and waist; the tight constrictiveness of the bra around my chest and the excitement of doing something taboo — boys don’t wear womens’ clothes.

It was an intoxicating feeling — all my senses aroused at once as well as feelings, senses and emotions I had never experienced before: a sense of aesthetic and tactile excitement: strange mixture of nausea and excitement in my stomach and the powerful stirring in my loins that, at that age I had no comprehension of. It was like an addictive drug on which I would be hooked on for the rest of my life.

It was something I knew I shouldn’t be doing. I kept thinking of the ridicule and the shame if my parents or someone else was to catch me dressed like that. I was constantly peeking through the curtains in case someone came home early. That combination of guilt and shame, together with the strange sensual and sensual excitement of dressing in womens’ clothes was an association that would have a powerfully pervasive impact on the rest of my life.

My father worked away from home a lot and when he was there he spent very little time with me. When he did it was usually in a disciplinary role.

I was always fascinated by women. I was seemingly always in the company of my mother and her coterie of friends including the attractive leggy 20 year old daughter of our next-door neighbours and her friends. In my daily life, in the absence of male role models, I was surrounded by women

In fact I actively sought out the company of women, especially young attractive ones, who would always make a fuss over the “cute little boy”. I loved being part of their conversations — about clothes and make-up and general gossip. I loved being complimented and comforted by them. .I adored the way they looked and smelled. I loved their mannerisms. I loved the way they dressed — especially stockings and high-heeled shoes. I enjoyed their warm, caring supportiveness rather than the briskness of men and the boisterous bullying of most boys my own age.

That first clandestine experience of dressing in womens’ was repeated hundreds of times in my childhood and adolescence. I loved stockings and later pantyhose the most — sometimes even wearing them under my pants to school, and at great risk of discovery and the consequent shame and ridicule. I progressed to panties, bras, tight foundation garments, high heels and occasionally make-up and perfume

Dressing like women do allowed me to feel what they felt. It was an intimacy at a distance that allowed me to love them without the embarrassment of rejection. As I grew older I discovered it to be an intimacy more satisfying than having sex with them.
But parallel to that, and always present, was an intense sense of embarrassment at what I was doing. It was not normal for a boy to dress in womens clothes - and especially to gain sexual satisfaction from it. So as I masturbated into my pantyhose enjoying the bizarre, androgynously feminine image in the mirror before me, I often thought of girls I longed for and what the boys at my school would think, say and do if they saw or knew about this - the shame and humiliation; the taunts of "sissy", "queer", and "faggot" would scroll through my mind as a I luxuriated in the feel and look of my pantyhose, heels, panties, and skirts, working myself to a fever pitch of arousal. I also began to experiment with light bondage, emulating images of damsels in distress that I would often see on afternoon television. The feeling of helplessness and vulnerability enhanced the feeling of femininity. In later life, I also often pondered whether it was also a means of reconciling my “perversions” with my “normal” life — that creating the fantasy of being forced to dress like a sexy woman took the choice out of it and made it “acceptable”.

Nevertheless, I went through this process of regular association of euphoric sexual arousal with the wearing of womens’ clothes, with vulnerability and with intense shame and embarrassment. Shame and humiliation and vulnerability became an essential- maybe indispensable part of the sexual experience.

As I grew older I dated and eventually, married, thinking these strange urges that so filled me with shame would go away once I had a real woman to satisfy my needs.

It didn't happen. I began to be more interested in their clothes than them. They often thought it a little strange that I wanted to have sex with them whilst they were nearly fully clothed. I frequently lost interest in sex once they had disrobed.

Once I confided to my wife a desire to wear pantyhose and panties to bed (I knew it was more than that but I thought introducing it a s a little fetish for shiny slinky things would be more likely to achieve acceptance) she never really looked at me in the same way. I think she tried to accept it but couldn't reconcile it with the image (façade?) of the man she thought she married.

After we separated my dressing took a very serious turn. I lived alone. I had the house to myself. I had a well paid job.

I threw out all my men’s underwear and socks. I wore panties and pantyhose or stockings full time. At work or with friends and family it would be opaques.

I began to invest heavily in my womens' wardrobe hosiery, shoes, boots, skirts, dresses, bras, panties, corsets, make-up, wigs, and jewellery. Mostly it was sexy day-wear, but I also bought a lot of fetish wear as well — latex dresses, skirts and cat-suits, frilly sissy maid outfits and lots more.
I went to gay clubs (not because I wanted to have sex with men, but because I believed it was a place I would find acceptance and be safe dressed as I was) in full makeup, wigs and womens' clothes. It was nerve wracking and again, the shame. Sometimes attempting to dress passably, sometimes more androgynously without a wig.

Occasionally a gay man would proposition me. I would occasionally dance with them because there was something excitingly humiliating about being seen by others dancing with a guy on a dance floor in full view of everyone in the room as my pantyhose sheathed lags shimmered in the strobe lights and 5 inch stilettos forced a very effeminately mincing step.

But I always rejected any physical attention. The idea of even kissing a man with his prickly stubble was repulsive. Let alone having sex with one was off-putting.

Most of the time I would seek out the attention of women that I found attractive — lesbian, bi or straight. Being with them; being dressed like them; crossing my legs like them; feeling the sensations they were feeling as they did so and knowing they were watching me as I did it - this is what turned me on.

The sexual identity I felt an affinity with was that of a feminine or “lipstick” lesbian. However, whilst most of the lesbians accepted me, I knew deep down I would not be attractive to them because I was male. I got lucky a couple of times but usually they accepted me as part of their group socially but that was it.

Similarly sitting among straight women - they would accept me as a curiosity (many thought it was cool to have cross-dressing friend) but they did not want me sexually (again with the odd exciting exception who was just wanted to a once-off experience).

But sitting there among these women gain reinforced my shame - I could never be one of them, but they would never see me as a male either. Again the shame and the excitement in tandem!

I started to take more and more risks to achieve the excitement and humiliation I was seeking. Going out in daylight to shopping centres, cafes, straight bars and cinemas fully dressed. I started to wear more daring outfits.

I loved self humiliation. I loved going out in public with a bra obvious under my shirt and sheer pantyhose and occasionally flat or low-heeled effeminate shoes on display under my trouser leg - sometimes tight womens' jeans with a plain-cut womens' shirt to keep them guessing.

I would love trying on stiletto heels in shoe stores and the look on the sales assistants face as I revealed a pair of stockinged feet and painted toe nails under my well cut suit. Sometimes disdain, sometimes surprise, sometimes a polite compliment about my nail polish or hose. I don't know what they were really thinking, but the words “sissy”, “transvestite”, “faggot” and “queer” kept going through my mind. These were terms I once eschewed but the humiliation associated with them began to turn me on. But regardless of what they actually thought, it was clear these women would never regard me as a normal red-blooded male.

One day on an overseas holiday in New Orleans I spent the day wandering around ultra shiny anthracite coloured Wolford pantyhose, a pair of black lace-up knee high boots with 5" heels and a plain dark grey silk womens blouse, with a little make-up, nail polish and no wig, and also a solid, heavily polished stainless steel slave collar.

Inside I was quaking with shame and apprehension, but also I pulsed with the excitement of being out in the open in busy French Quarter streets in broad daylight, my shiny hose sheathed legs, shimmering in the sunlight as they swished against each other was breathtakingly exciting.
There was no hostility, but I did attract I some stares, smirks, giggles and the occasional wolf-whistle.

I settled in at a mixed gay straight bar off Bourbon Street.

It felt like the whole room was staring at me. After I had a few drinks, a rather good looking, blonde haired, athletically built guy who had been sitting in the corner casting glances came over and asked if he could join me. He seemed harmless enough and I was getting a bit bored with just sitting there alone.

He asked me if I was a transvestite. There was that word. It excited and embarrassed me at the same time. It was pretty obvious from how I was dressed but it was his way of steering the conversation to what he wanted.

I gulped. I was blushing with burning embarrassment. I looked down at my stockinged legs and shyly whispered "yes". He then ran his finger over my steel collar and asked if was a submissive and into bondage. I again whispered in the affirmative, without raising my eyes.

He was reading me perfectly and playing me like a violin. He placed his hand on my stockinged thigh and began to caress it. His hand strong but also was soft and warm. I didn't resist. It was the first time I had allowed a guy to get that intimate with me. It felt kind of nice having someone caress my thigh through the sheer pantyhose.

Others were glancing at us - especially a group of young girls a few meters away. They not only saw a sissy transvestite who was not a real male, but one who was surrendering to the seduction of a man.

He spoke to me for another 20 minutes talking to me about my fetishes and his whilst caressing my leg, occasionally brushing over my swelling cock as I was getting more light-headed.

Then came the point where he just grabbed me by the wrist, firmly, but gently, pulled me off my stool and pulled me towards him. I felt so weak and helpless. Any resistance was only token. He was so big, strong and athletic and I so small effeminate and weak. And as if that weren't enough, I was dressed like a little sissified, androgynous faggot.

He placed his lips over mine and forced his powerful tongue down my throat. The stubble; the masculinity of it was a little off-putting, but the sheer helplessness of my situation and the humiliation of being so forcibly seduced by a man in front of the bemused eyes of countless other men and women in a crowded bar was so arousingly humiliating.

Shortly thereafter we left the bar with him grabbing me by the wrist. I had no will power. I was just following him wherever he wanted to go.

He led me to a shop off Decatur Street which was a leather and fetish shop. He bought a pair of steel handcuffs, a steel chain leash and heavy leather bondage helmet with nose whole, a zip opening at the mouth and no eye holes.

I was thinking about pulling out — telling him sorry, but I wasn’t ready for this. But whether it was my own weakness, or maybe my light headed inebriation, something kept me there. Maybe I wanted to be there or just to see what happens next.

He fixed the leash to me steel collar and cuffed my hands behind me.

Where was this going to end up?

He the tugged at my leash and marched me out, in broad sunlight, into a crowded street. Meekly I tottered along behind him pathetically in my stiletto heeled boots; my pantyhosed legs shimmering vibrantly in the sunlight and my hands helplessly cuffed behind me.

I was so obviously a bizarre transvestite queer. I was so obviously HIS. In a public street! Was this really happening? Was this really me?

I was so engulfed in the most intense humiliation and embarrassment I had ever experienced. Yet I was also on the cusp of a powerful orgasm, despite the fact that there was no contact with my genitals.

People stared open-mouthed; they pointed; they sniggered; they laughed. I was his pathetic little transvestite pet — out in a crowded public street and visible to all.

After what seemed like an eternity we eventually reached a build down a side laneway where a man opened the door and seemed to know my conqueror (I still didn't know his name).

We went down to a dark cellar which had about 20 or so black leather or PVC clad men in it. It appeared to be a gay S&M bar. A few of the men seemed to know my ... well.... Master. It was at that moment I came to accept having a Master. He sat down with a couple of them at a couch in the corner. With my hands cuffed behind me and the handle to my leash wrapped around his wrist, I was pulled down to kneel before him on my stockinged knees

“Where did you get this little Nancy-boy queer?” one asked.

"I found it dressed like this, sitting around in a bar in Decatur Street he said.

"It"???

I was a thing. An object!

I was then led over to a little cage built under a high drink table. He motioned for me to enter it, which I did. There was round hole in the bars through which he opened and pulled my head and then locked a steel fixture to prevent me withdrawing it. He then fitted the leather hood he had bought over my head and laced up extremely tightly. I was on my knees, in a cage, my hands cuffed behind. Totally helpless; totally vulnerable; totally intoxicated with sexual excitement! I couldn’t see anything. From here on in; I no longer had any ability to resist t or object to anything that would happen to me. I could hear some muffled voices I could still feel the sensuality of my panties and pantyhosed legs caressing slightly against each other.

All of a sudden I could feel a large throbbing cock brushing against my lips through the zip in the mouth of the hood. After pursing them initially, it kept pushing at my mouth. I eventually allowed it in. I nearly choked and almost vomited.

Here I was helpless, feminised, objectified and caged with a guy's cock in my mouth as he stood there drinking beer with his friends.

I started to work his cock as I would have liked mine sucked. It swelled in my mouth and eventually erupted.

I could in a muffled way through the hood hear him; matter-of-factly, put his cock back in his pants and resume his beer. I was kept there for about another hour before he eventually released me and made me masturbate into my pantyhose before the whole room.

Did I enjoy sucking his cock? No.

Did I enjoy the humiliation of being helpless, feminised, chained, hooded and caged whilst being forced to do so? WOW!

It was the point of no return. Until now I convinced myself I was a more or less “normal” male with a harmless fetish for womens’ clothes. Now I was a “queer”; a “faggot” … a “transvestite “gimp”. Forever! Whether I enjoy sucking cock for its own sake is irrelevant — and I don’t. I enjoy it for the humiliation. I only suck cock when I am dressed in womens' clothing.

And I am well and beyond the point of no return