A brief introduction is in order; Mistress Alison is a good friend and a very knowledgeable and experienced Mistress, she has also been a frequent contributor to PDQ. She is now available to answer questions from both Mistress and sissies alike, assuming a respectful tone of course. These email conversations may well be included at some future date in PDQ though a request for privacy would be respected. Feel free to write her at and please don't waste her valuable time asking "where / how can I find a Mistress?"

Dear Mistress Alison,

I am writing to ask if you think it might ever be possible for an 83 year old to finally realise a lifelong dream of being petticoated by a dominant lady. Or am I just being the old fool that there's no fool like?

My interested in being petticoated began when as a 5 year old, after the bombing of Coventry, I was evacuated from the English Midlands to a particularly dismal part of rural Wales. I was heartbroken at being separated from my beloved sister a year my senior, but that was only the beginning of my travails. I was billeted in a cold, dark, damp farmhouse with absolutely no mod cons run by a devout but dour couple. I seldom saw the farmer except in chapel, he was out working before I was allowed to get up and still working when I was sent to bed. His wife was as cold and forbidding and cheerless as the farmhouse itself. Grasping, tight fisted, flinty hearted and mean spirited, she looked on me as a source of income and a nuisance. I don't know what she was being paid but precious little of it was spent on me. My day to day supervision was put in the hands of her teenage daughter, Dilys.

She must have been around 14 or 15, but even at my tender age I could see she was going to blossom into a looker, a bobby dazzler as we used to say, but she too had a cruel streak. Every time I did something wrong, which meant something she didn't like, she would cane my hands because they had fallen into doing the devil's work as she called it and then laugh at me for crying. She used to say, "you're not really a boy at all, you're a big girl's blouse of a sissy." Back then being caned was more or less routine but being called a sissy was just about the worst insult there was for any boy, or man.

Due to wartime shortages whenever I outgrew any of my clothes or they got torn, I got given Dilys's cast offs to wear. School knickers, blouses that buttoned up the wrong way, girls shoes etc and when my trousers were in the wash one of Dilys's old gym skirts. Whenever I was wearing this Dilys would cane the backs of my legs instead of my hands and tell me that now I was dressed like the sissy I really was. Despite all this I was in awe of her, under her spell. Much later when I saw the film Great Expectations, Estella reminded me of Dilys and I knew just how Pip felt, like a rabbit caught in the glare of a car's headlights. Wearing the girls' clothes felt strange but not unpleasant, it made me more aware of what I was wearing and over time I got to quite enjoy it. It made me feel a bit special as I was doing something no other boy I knew had done. Naturally I got mocked by the boys in the village school, but some of the girls would ask to see what I was wearing under my gymslip then feel my knickers to see if I was the same as them underneath before running off giggling. That too made me feel special. This situation lasted until 1943 when I was sent to live with my grandmother back in Coventry. Although I was delighted at the prospect of going home and being reunited with my sister, I also felt a real pang at the thought of never seeing my beautiful tormentress again. This ambivalence of feeling would endure throughout my life.

My joy at being reunited with my sister was short lived as I learned our father had been taken prisoner after the fall of Singapore. He never returned. On the plus side, after I told my sister about my experiences with Dilys she let me wear her knickers whenever I wanted to. This wasn't every day you understand and it certainly wasn't an obsession, there were far more important things in my life like football and trying to decide which branch of the forces I wanted to join when I was old enough. We all just assumed that the war was going to last forever. Then one day my sister just said no, I couldn't wear her underwear anymore and that it was wrong. I now realise that she had reached puberty and had lost enough of her innocence to realise there was a sexual component to my wanting to wear girls pants. It is impossible to exaggerate just how sexually innocent we were back then, it really was a different world and talking about sex was one of the deepest taboos there was. The only sex education, if you can call it that, my wife ever received was on the morning of our wedding when her mother whispered to her, "When he does it just take a deep breath and remember it happened to the Queen." Even as late as the early 1960s jokes about honeymoon couples not knowing what to do were commonplace, and like all good jokes contained a large element of truth.

The rest of my childhood passed without significant incident, naturally the war did come to an end, and I attended single sex primary and secondary schools before leaving at 15 to work in a local factory. During this period I occasionally thought about Dilys and what might have happened to her and what might have happened to me had I stayed longer, but in a manner more wistful than overtly sexual.

Then I was called up to do my National Service. After basic training I did what so many others in my position did and visited a prostitute in order to lose my virginity before being posted abroad. This was easy back then as every major city had a red light district where "girls" openly worked the streets, particularly around the main railway stations in London. The deed having been done, and what a disappointment that was, I asked the woman if she would cane me. She wasn't a bit shocked but said it would cost me a shilling (now 5 pence) a stroke, a lot of money for me back then. But when I asked if I could wear a pair of her knickers while she did it she became abusive and used language the like of which I'd never heard before and threw me out. I was posted to the Far East, a cruel irony since my father had died at the hands of the Japanese while working on the Burma railway. In Kuala Lumpur I met another soldier who liked wearing female clothes and at first he was quite friendly telling me ways I could wear women's things under my uniform without detection. But he turned out to be gay, a fairy as we called it, and wanted much more than friendship and turned nasty when I rejected his advances.

After my demob I returned to my job in Coventry and in a short time met and married a girl and settled down to a life of blameless normality. I still thought about Dilys from time to time, but never mentioned her to my wife and never did anything further about wearing female clothes or being caned. I could have worn them under my usual clothes in secret like some of your correspondents, but it was important to me that I be made to wear them, forced if you like, rather than do it voluntarily. I don't know why but that's the way it was. In the same way I didn't want just to be caned, but caned specifically for wearing these girls' clothes. The only abnormality in our marriage is that we never had children, I don't know whether that was my fault or my wife's; one just didn't ask things like that back then. We tried enthusiastically for ages at a time when the only form of contraception was what's now called a condom, back then it was universally known as a Johnny, a real passion killer if ever there was one, but even without contraception my wife never conceived.

Once I visited a doctor and confessed how I couldn't get the idea of wearing women's clothes out of my mind. He looked at me with withering contempt and asked me if I was a poof, which was illegal at the time and people could and did gent sent to jail for homosexuality. I told him I definitely wasn't, was happily married and was trying for a family, but that as a child I'd been forced to do so by a very pretty girl and I just couldn't seem to get over it. He curled his lip and said, "For God's sake man, try to get a grip and pull yourself together." I changed my doctor as I was too embarrassed to go back and have never repeated the experience.

Six years ago my wife passed away and I grieved in solitude for a long time, becoming something of a recluse. Then I thought about the possibility of some female companionship and so joined a social club for senior citizens, how I loathe that patronising term, and was introduced to the possibilities offered by internet. I'd always liked dancing and since in my heyday of the 1950s the ladies, they were always ladies back then, wore proper full skirts with petticoats and white gloves I bought a CD of dance tunes called Dreamboats and Petticoats which brought back a flood of happy memories. Then one day looking for similar recordings I mistyped it or accidently typed it the wrong way round or something or other and one of the web sites that popped up was yours.

I was amazed and intrigued in equal measure. I'm not vain enough ever to have imagined my experience or my feelings were unique, but the fact that the phenomenon of men actually wanting to be dressed as women, schoolgirls and maids was apparently quite common was a real eye opener. Also the fact that many, many women are more than happy to accommodate them in this and that, if what you say is accurate, even more are prepared to force them to do so against their will was even more of an eye opener. All my memories of Dilys came flooding back and I ended up dripping tears of regret onto the keyboard at the thought of how I've wasted my life on blandness and mediocrity.

I apologise for having bored you with my "life" history but please be honest with me, is there still a chance? I am still in vigorous good health for my age and keep both physically and mentally active so I would like to think that even at this late stage it might be possible to realise my dream.

Yours more in hope than expectation,

Dear Reg,

Thank you for most poignant letter. I am sorry you lost your wife and even sorrier that you feel that your life has been wasted. Your generation went through privations and the kind of heartache that the rest of us can only imagine and I think you should be proud of having come through it so well.

I am not in least surprised by the reaction of the doctor you consulted, even in today's more enlightened atmosphere many people regard cross dressing as some kind of aberration or perversion and many more associate it, completely erroneously, with homosexuality.

Dilys, the girl whom you describe as your "beautiful tormentress" gave you your first sexual stirrings and since she also gave you canings and dressed you in girls' clothes it was almost inevitable that these things should become inextricably intertwined. This was reinforced by the actions of other curious and maybe not so innocent girls touching your genitals. You may feel regret about not having done anything about your feelings and desires but the one emotion you should not feel is guilt. You have done nothing wrong.

In answer to your specific question the truthful answer is that you have left it very late and therefore your chances of success are that much lower. However that does not mean your quest is unattainable or that you shouldn't try and with the advantages of the internet you are probably better placed to find someone to help you than at any time in the past. But time is of the essence and you should not delay in taking positive action. What that action should be rather depends on what sort of experience you are looking for. If you just want to dip your toe in the water with a one off and see where leads then would probably be best to visit a professional, who will understand exactly what you are looking for and be able to provide a session tailored to your own particular needs. However you would be wise to bear in mind that time and distance may have given your childhood experiences elements of romance and glamour that never really existed. If you are looking for a longer relationship based on petticoating and discipline then you would be better off looking a specialist dating sites on the internet. Remember when either posting your own details or replying to someone else's advert that you do not have the luxury of the time to be coy, so I would advise you to be as open and direct as possible.

Please do write again if you want any further information and also to let us know how you get on.

I wish you every luck in your search.

Yours sincerely,
Mistress Alison

(Edit: He has now found someone prepared to help him fulfil his dream.)

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