The first piece of feminine clothing I ever owned and wore was a latex miniskirt I bought while shopping on my 25th birthday – this was the day that something stirred inside me, and I look back at that day as when I came out to myself.  

I was browsing around one of the alternative clothing stores looking for some new clubbing clothes, and I saw this black latex miniskirt on sale. Looking at it, hanging up on the display wall, I suddenly had this weird, overpowering urge that I needed to buy it and the intense desire to wear it. Confused, I let these strange feelings rule me, so impulsively I decided to buy it. Then while waiting to pay for it, I grabbed some nylon stay-up stockings and some over-the-knee socks that they had on display by the cash till – on the premise, as I told the saleswoman, I was shopping for my (non-existent) GF.

When I got home, I locked myself in my bedroom. I took out all what I had bought and I was thinking to myself, ‘What the fuck is going on with me? Am I gay or something?’ Feeling shame inside, I really did not understand what internally was driving me to do this, but it felt it something I needed to do and experience.  

That night, after everyone in our house had gone to bed, I took a late bath and shaved my legs. Then once safely locked away in my bedroom, I sat on my bed, starting to roll the stockings up my now smooth legs. As I felt the nylon stretch and take form over my legs, I remember a conflict of feelings going on, it felt both so very wrong yet so very right. I then stood up and pulled the latex skirt up – and then being deathly afraid to look in the mirror, in case I saw something I did not want to see. However I was also finding myself uncontrollably aroused, the skirt now showing off a massive bulge underneath.

I laid down on the floor, fingered my ass with some lube, and then silently fucked myself with one of my dildos for the next couple of hours pleasuring myself. Some years before I bought this skirt, I had discovered anal sex – so I had a collection of dildos and vibrators to experiment and enjoy this kink of mine. I’ll talk about those another day.

I remember when I finally recovered from my repeated arousal and orgasms, and decided I needed to clean up and hide my new secret until my next opportunity, I had tears running down my face because I did not understand what was happening to me. I felt like I had crossed over some perverse threshold of no return – but at the same time, it felt like I had opened a new door from how I felt from this new sense of arousal. I knew I wanted to explore this newly-unlocked kink more.

Over time I would buy more skirts – such as a short, pleated tartan schoolgirl skirt, or a black satin, pleated skirt. I also had some black spandex miniskirts I would wear on a casual basis alone in my apartment, overtop black leggings.

A woman I knew in the scene named S was into wearing old-style lingerie. She was one of the first to know about my secret bisexuality and crossdressing kink, and to show her support and encouragement she made me a really short miniskirt from one of her black lace girdles. It was nowhere as comfortable to wear as the pleated ones for movement, as this girdle skirt would keep riding up and exposing my ass whenever I walked or danced. It forced me to cross my legs when I sat down, unless I wanted to show off my manhood underneath. Despite its awkwardness for me, I got asked by Mistress R to wear it a lot, because it showed off my tight ass really nicely – and as soon as I got remotely aroused underneath, it would also show off my bulge – and she liked showing me off when we were together. ‘That skirt sells you as sex’, as she would often tell me.

The pleated skirts I could get away with wearing bike shorts underneath, comfortable and useful for nights when I went out dancing - but with miniskirts, and their hip-hugging tightness, I would have to wear a leather thong that could barely hold me in. Occasionally I would wear nothing under my skirts, when I was on a serious prowl for some action and wanted to show off to tease, or get felt up in the process. That was how I lured my very first attempt picking up a guy.

One of the outfits I wore for Mister EU was dressing up in what I called my school-boy outfit. I knew and played off for arousal how many older men seem to really get off on the private school-look, but this was really was just modifications on something I wore out to my local clubs: black shirt, black tie, black shorts, and black over the knee socks, with doc marten boots – with my hair gelled and combed back or over to one side, glasses, and black lipstick. I do seem to recall, too, once dressing up as a private school girl for him complete with a black bob wig.