The Road to becoming a sissy, part two

I have written about a time spent fooling myself that I was a macho man who simply liked to wear lingerie – and after all this is evidently not uncommon in the heterosexual male. It has been suggested that such men are so in love with the feminine that they want to take it into themselves. I carefully avoided such analysis when it came to myself – I just knew that I got an erotic charge from dressing like this.

So I would set time aside and put on the few things I owned – first the corset – I loved and still do love corsets, not only for the way they transform the figure but because they are a kind of bondage device! The feeling of the corset tightening around me is still one of my greatest pleasures. Then a brassiere – no breast forms. Stockings – black, fitted to the suspenders of the corset. High heels – 6 inch stilettos in which I would totter for the time it took me to masturbate and cum. This usually happened in about five minutes.

And the first thing I would think as immediately I started struggling with the laces of the corset was always, ‘What a ridiculous thing to do. What an idiot I am. How stupid and ridiculous I look’ And there would be a kind of sense of shame and guilt and a resolve not to do it again.

In my first full blog post, I wrote about meeting a straight man who dressed me totally for the first time in my life. I was interested in what he was up to but… he had a number of traits which I did not share. He was working on being extremely 'convincing'; although married (his wife knew nothing, he assured me) he had a desire to appear as a real woman - hence his love of breast forms, make-up, despite his lack of skill, and he even had an artificial pussy. All of these he was keen that I should try. He had considerable guilt about his tendencies and tastes and finding someone who would go along with them and share them seemed to lessen his anxiety about himself as a pervert. By this stage of my life I was pretty happy with being a pervert in a number of other ways - of which more soon - but dressing was something that I had repressed for so many years that I am sure I, too, had 'issues' to deal with.

One of the things he insisted on was that I must have a female name - this was important, he assured me, and would help me relax into the clothes. I still had a problem about relaxing into the clothes and was reluctant to commit to this - or indeed to wearing the breast forms, wig or pussy. I wanted to be a bloke in women's clothes. I could not think of a woman's name that I could feel happy with - he it was who came up with the name Xena, after the eponymous heroine of a popular television programme. He argued that I was so macho that only a name with Amazonian associations would be appropriate. So with him I became Xena.

He also had BDSM interests... With these I was more familiar, having been involved in the leather fetish world from my early 20s. I think this was another example of me trying to present myself very much as a macho male; wearing leather and uniforms projected a stereotypical masculinity. I was particularly happy with BDSM in this context because I could allow the dressing to happen so long as I connoted it with the idea of being forced. Hence my interest in 'forced feminisation' which of course is not forced at all but something I now eagerly rush towards, not shy away from. Still the complexities of the human psyche are such that the IDEA of being forced to wear the clothes of a woman is still a huge turn-on.

I still have a couple of photos from those early sessions, some ten years ago. In front of me as I write, I have a picture of me in full, ghastly make-up, bound to a St. Andrew's cross.

Looking back, I see now that I was something of a selfish prick - I used his clothes and gear and essentially gave him nothing in return. After a number of sessions, we drifted apart. There was no sex involved and I would have liked that, though not with him en femme; the idea of 'lesbian sex' - sex with a man who was also crossdressing - had no appeal for me.

I wanted to have sex with a man. I had always had sex with men – but little by little I began to see that I wanted to have sex with a man with me dressed fully as a woman.