The making of a sissy

I started in my teens, with the onset of puberty. And it was the classic start - mother’s things. By this stage, women’s lib had taken firm hold of many sophisticated women in various sophisticated societies but 1970s Ireland was way, way behind. So my mother wore all the classic retro stuff - suspender belt and stockings, girdles, heels. Let’s face it, you really can’t imagine a greater distinction between male and female clothes than this stuff that always seemed to me to be part of a sacred mystery. The clasps, the intricacy of attaching stockings to a belt; the girdle which shaped and held you; a bra - why was such a thing necessary? Of course, I stuffed socks in the bra to fill it out but, at that stage, I had no idea of the weight of breasts so a bra seemed to be part of the mystery. Such lingerie definitely shaped my sexuality and I’ve followed my mother in those tastes with one addition - corsets, to change my figure.

I was a strange little boy in any case - I played with girls at school, joining all their singing and dancing games. The only boy who did so. That was fine until about age eight when bullying started with the name calling - sissy, pansy, fruit, fairy. I was forced to realise that I was NOT to take part in the singing and dancing of ‘wallflowers’ -

Wall-flowers, wall-flowers
Growing up so high,
All fit for heaven
And all sure to die,
Except (girl's name)
She's the fairest of us all
She can dance, she can sing
She can turn her face to the wall.

There’s a kind of cruelty in this song as, one by one, the fairest turn their faces to the wall so that, increasingly, it’s the ugliest who are left behind. How delightful it was for me, as the only boy, to turn my face early!

Well, now that stopped. Another thing I remember was that, if a boy misbehaved, his punishment would be to be placed among the girls and have to share a desk with a girl. I thought that was not a punishment in my mind but I came to see it as such because that was the meaning that was projected.

Age eleven, a new school and a chance to break free from the bullying. I quickly saw that, to survive, I needed to butch up. I just needed to stop being a sissy boy and become an ordinary boy. I really worked at rugby and cricket and, although I detested both, I became quite good at them. It worked. There was no bullying, no name calling. I was passing as a boy! Oh bliss!

But at the same time, I discovered my mother’s lingerie and wearing it was such a sinful pleasure, inevitably leading to shame and guilt. So I was really leading a double life. As a boy, I wanted nothing more than to be ordinary; as a girl, I was excited, thrilled, moved, different. I forced myself to stop dressing.

Fast forward almost twenty years and I was a veteran of gay relationships, always in the passive role but still repressing all desire for female clothing. Then, with the birth of the internet, there were so many different lifestyles laid out before us. I met a man online who crossdressed and he pestered me for a meeting. So I did and generous guy that he was, he allowed me to make use of his female clothes, his breast forms, his makeup. He applied the makeup and had no skill at it whatsoever. I still have pictures of those early meetings and they are horrendous! It was a start, but it still didn’t really seem like ‘me’.

So I took myself off to Transformation in London, a shop that catered specifically for the trans community. I wanted only the lingerie - anyone detecting a bit of Freudian interpretation here? I bought a really fine and expensive corset. I still have it and wear it. ‘The mean person travels the same road twice’ is really my motto. The sales girl was Irish and was very good at talking me out of expensive, ‘ordinary’ stuff like stockings - ‘Go to Marks and Spencer for those,’ she said, ‘and for panties and a bra.’ She measured me and obligingly wrote down the sizes I should look for. I did buy a wig, and a gaffe - so I wasn’t totally avoiding a feminine look - and a pair of six inch heels. Still got those too. ‘Those aren’t beginners’ heels’, she said. ‘But they’re the height I want,’ I replied.

Now began a few years of lots of dressing in this lingerie, always alone. As I got bolder, I’d do a lot of cam to cam - though usually I was looking at nothing more than an erect cock. Never a face. I still did not possess a dress or any makeup other than lipstick.

Then along came my Scottish mentor, Tom. How many hours of chat did we engage in, late at night, when his wife was in bed? I enjoyed these chats because although they involved sexual matters, they were not overtly sexual, not designed to provide him with an orgasm. He wanted to know me, know my history, find out where I was coming from - and where I might go. This went on for months. My onscreen name was ‘butchcd. At that time I had abandoned the wig and wore my hair like a skinhead. I did it myself with clippers. I think I was a number three cut at that time.

Somehow a professional photographer from Israel got talking to me in a gay club in Berlin and made an appointment to come and photograph me - no wig, no makeup, just the lingerie and a pair of Dr. Marten skinhead boots; me smoking a cigarette and I don’t smoke. The photos ended up in a Tel Aviv art gallery! I love them as they capture my ambivalent attitude.

Armed with all his knowledge of me, Tom amazed me one night by saying, ‘Your problem is that you are in denial about who you are. You are really the little boy you were until the age of eight when you were made painfully aware that the days of your natural innocence were over. That little boy was a sissy, and you are still a sissy.’

The very word was a blow. It brought back so many of the insults I had endured. I had spent years and years escaping it and now it seemed I could not. Was I a sissy? Could I not be a butch crossdresser? At that time, I was a very keen member of an online site called Lingerie Bears. It consisted of many seemingly masculine guys who liked to wear female lingerie. They were bearded, they were burly, they were fat and thin - but no wigs, no makeup. Just guys in lingerie. I had felt that this was who I was and who and what I was meant to be.

Now, to the outsider, the distinctions within the trans community may seem very fine and there can be vastly different interpretations of what each ‘category’ means. Some people have strict interpretations of what each term - girl, cd, tv, ts, shemale, sissy - may mean and others do not and feel they can be used indiscriminately. But Tom had a very definite notion of what a sissy is.

I was shocked but I was intrigued because I had a faint, oblique sense of things in my life coming together and making some kind of sense. I listened as he explained who and what I am.

He said it was time I gave up the name ‘butchcd’. I needed a sissy name. Any suggestions? I could not think of any that captured my essence and brought different parts of me together.

‘Were you called a Nancy boy at school?’ Indeed, I was. ‘Then you’ll be called Nancy from now on, for ever.’

That started a new life for me. He encouraged me, he advised. I was no longer to be in denial. I was to embrace the sissy, release her, from all those years of captivity. Pink - what else? - became my colour. Lace and ruffles and flounces, became my ‘look’. Little girl party dresses, a bonnet, a wig straight out of Little Women with bangs and curls - these were all added to my wardrobe.

And I met Tom - many times. By now I was living in Berlin and his work took him there often. He came to my flat. I was ready for him, totally nervous as I had never presented myself to any man, even on cam. But when he arrived, I became very relaxed. This man knew the real me more than anyone in the world. I had found who I was. He had not finished with me. He was a critic. I was to lose every last element of masculinity in me. It was not permitted. Every movement must be sissy to the nth degree, my voice should change, I must be feminine to the extreme. And as I attempted to do what he asked, I really did feel free and empowered. I am still a sissy. I always will be, just as I will always be Nancy. Being a sissy has also allowed me to live out of a feminine side. The sissy is the ultra feminine but there are gentler feminine personae too and I happily live out of those, while having an eye and ear out for that rare bird - the man who loves ultra sissy sissies.

There are other sides to this. It turns off more men than it encourages. And I do still try to ‘pass’ as a convincing woman to get close to men and have sex. But, despite this, I do know who I am. I am sissy nancy.