Dear Nanny Susan,

I read a number of letters by chance, having found your site while looking up the Caithness Schools site. I somehow clicked on 'navy knickers' there and found my way to Susan MacDonald.

I am new to the internet, having done a post-retirement course this year in the internet and find it most interesting. I found your 'Advice From Nanny Susan' questions and answers interesting, because most seem to be from men who are interested in wearing girls' clothes, or from women partners who are with men who had petticoat experiences as boys, and who want to relive their experiences.

I wonder have you ever written anything about the psychology involved? It seems a quite common experience with some boys to want to dress or act as girls, at least part of the time. The reason I’m writing is to give you some information from another angle.
I was a young teacher in a rural part of Scotland in the late 1950s. A small house, for rent, came with the job because of the isolation of the school. A boy of about 11 became friendly with me through his mother. I shall call him 'George' because he now has a job in the public eye. George used to call with me frequently, sometimes several times a week, to have tea and do his homework with my assistance.

To cut a long story short he came to stay with me during the summer holiday. Almost without noticing, I became aware he was interested in my clothes, especially my underwear. Several times I found he had been rummaging in my dressing table drawers – always in the undies drawer.

He also volunteered to hang out or take in the washing and I would have been blind not to notice that he had favoured certain things – like my brassiere, corsets or knickers, which he handled with reverent care. I confronted him one day when I stole upstairs and found him in my bedroom, naked except for a pair of knickers, admiring himself in the mirror. He looked ridiculous. And I told him so.

No sooner had I done that than I deeply regretted it. He burst into tears.  For the next hour he sobbed uncontrollably, and then sniffed for another hour. I really regretted having upset him so much. He said he didn’t know why he had put on my underwear. Eventually, I got him to admit that he had wondered what it was like being a girl, and how it felt to be dressed as a girl.

I told him my things were much too big, but I had some older things which were smaller. I fitted him out with an old pair of stretch knickers and a skirt, and he became calm and even smiled. I told him I’d get some proper girls' things that would fit him

We lived some distance from the nearest drapery shop, but in a cupboard in the girls’ changing room at school there were some old clothes, abandoned or lost over the years. Next day, I gathered up a pair of navy knickers, a gym skirt and a white blouse, torn at the arm. Later that day when George and I were alone at home, I took the girls' clothes from my bag, telling him I had a surprise for him.

He was reluctant to put them on at first; blushing deeply and looking a bit frightened. I told him not to be silly. Just him and I would know. “Just try them anyway, to see how you feel”.

I helped him scramble reluctantly into them. He was terribly shy at first, standing apart from me, staring out the window after he had put on the blouse and skirt, apparently not noticing the navy knickers on the arm-chair beside him.

With a curt, “Don’t be silly”, I lifted the knickers put them on him saying, “Your bum will feel much warmer now.” We both laughed. I asked a couple of times how he felt, but he squirmed with embarrassment, so I ignored the way he was dressed and carried on normally.

At bedtime, he seemed reluctant to go upstairs. I guessed he didn’t want to take the girls' clothes off. So I asked if he wanted to keep the knickers on in bed. He brightened up immediately. I fetched the top part of an old pair of pink, baby-doll pyjamas and he pulled it on. It fitted him like a nightie.

Next morning, he was up hours earlier than usual – dressed as a girl. I knew when he came into my bedroom that he had some deep need to dress as a girl. I gave him a kiss, pretending not to notice his skirt and blouse, which looked silly with his boys' heavy black shoes.

Maybe I’m an unusual woman, but I saw no harm in George playing at being a girl. He was doing no harm, and if it made him happy it was fine with me. That is not something I could have said before I came across your web site. There is some big taboo about boys dressing as girls, although I have to say this taboo is largely with men and other boys, not with females.

We women often use male clothes as part of our fashions, and there is no outcry. But the idea that I, as a grown woman, assisted an II-year-old boy to play-act as a girl would be regarded by a lot of people as terribly wrong! Anyway, while I have never disclosed before now what I encouraged George to do, I am not ashamed of it and am glad to write to somebody who may understand, Susan.
That weekend we set off for a Ladies' and Children’s Shop in a nearby town.  At first George was a bit awkward, and hung about red-faced while I selected various bits of clothing and underwear. By the time he came to fit on a pair of unisex scandals, he realised no one in the shop except me was taking the least notice of him. I bought some white ankle socks as well, and later we visited a tea-shop.

Before leaving we decided we should both do a wee before motoring home in my old Singer. What happened next was spontaneous. George went ahead down a dark, narrow corridor marked 'Toilets'. As he pushed open a door, light flooded in and I saw a 'Ladies' sign on the door which George had missed in the darkness, or maybe he hadn’t!

In an instant, without thinking, I propelled him ahead of me into the empty toilet. We were both in a cubicle together before either of us knew what was happening. As I bolted the door I asked if he wanted to go first. He said no. I lifted my skirt, pushed down my knickers and sat down. As I was weeing I asked why he didn’t want to go. Was he shy or nervous? I asked. He said no, but I knew he was.

While I stood up, dried myself and fixed my clothes in place, he watched in fascination. I knew he was torn between wanting to flee and wanting to stay, between whatever urge he had to be a girl and whatever embarrassment he felt about being in the Ladies. I took command of the situation and without another word pulled down his shorts and trunks and pushed him down on the seat, the way I would have done with a five-year-old girl at school, saying that we had a long way to go and he must do it before we left.

He sat there for some time after the last dribbles had echoed away. I knew his embarrassment had returned, so I pulled off some paper and handed it to him, saying in my most school-mistress voice, “Here, dry yourself well”.

He did it remarkably well. I wondered if he had done it before, or if he had simply it picked up from watching me a few minutes earlier.

On the way home he was like a new person, grinning and talking non-stop in a giddy way. It seemed amazing that such a change had come over George. As we drove, he took the brown paper parcels from the back seat and opened them.

His shyness disappeared as he examined his new things, holding a pair of pink cotton knickers against his waist to try them for size. I said I would call him 'Georgina' from now on, and told him the knickers would fit a lot better than my things. Then we giggled and laughed for ages.

At home, he ran upstairs right away, asking if he could fit on the new sandals as well. I said "Of course", noting somewhere in my head that he was reacting to the new clothes just like a girl. When he didn’t re-appear for ages, I called up, “Georgina, are you dressed yet?” Slowly he descended the stairs. When the kitchen door opened I could hardly believe my eyes. The little boy George had really become little Georgina.

I know your readers give a lot of detail about these things, so I will do the same, in as far as I can remember. Georgina was dressed in white socks and brown sandals. Above that she was wearing a dusty blue, cotton, round-neck frock with a broderie anglaise scallop collar, fitted bodice, and wide skirt, which ended well above the knee. She looked lovely.

I stepped over a gave her a big hug, then a kiss on the cheek – and was amazed at the way her body reacted like a girl – no squirming, just a confident return of my affection. I lifted her dress and noted her vest was tucked into her pink knickers.

“You should wear your vest outside your pants in the summer. It’s much cooler”, I said.

A few minutes later I was brushing her hair and fixing a white bow in place with a slide. The light brown hair was quite short, longer than most boys were, but not as long as the average girl. But it looked so cute. My little boy-girl seemed so cuddly.

From then on, Georgina dressed as a girl every time she was in my house. It was our big secret and seemed to harm no one. In truth, I looked forward to our little game more than she did. I still can’t explain why.

When we had visitors, which was rare, George had to remain as a boy. He was always miserable then.  I would bring Georgina comics, 'School Friend' or 'Girls' Crystal' to compensate. Sometimes there were other little treats, like perfumed talc or nicely scented soap.

Our secret remained for years until one day, on the Home Service, a psychologist was talking about homosexuality, saying the “disorder” sometimes arose because boys had been treated as girls, either by their mother or by an older woman. It seems a stupid claim now, when sex and homosexuality are more understood and openly talked about. But then, a talk like that was revolutionary.
I wanted to shout at the radio, "I don’t believe what you are saying! It’s nonsense, what would you know?" But I couldn’t. I was absolutely terrified and guilt ridden. Sure that I had messed up my little friend’s future life, I threw out all Georgina’s clothes.

When she came round next day and went to change, she burst into tears, after discovering that her whole identity as Georgina had gone. I told her it was for her own good; that she would understand when she grew up. We both sat and sobbed. Georgina had existed for three years, and in that time had become a sophisticated little lady who helped around the house and shared my thoughts.

She never forgave me. Although we remained friends, George took to boys’ teenage activities – he was 13 when I destroyed Georgina clothes.

What I want to know now, Susan, is was I wrong to dress him as a girl in the first place, or was I wrong to destroy his life as a girl?
He is grown up now, married with three children, and I see him from time to time on TV because of his job. I often wonder does he remember his time as Georgina, or what he thinks about the need he had then.

A few years ago, there was a TV series about a 12 year old transgender girl who was going to have an operation in Holland to become a boy. She had been dressing, with her parents and school principal’s permission, as a boy since she was nine or so. The boys in school accepted her as one of their own and she played on the school football team.

My friend, Mona, who was watching it with me said, as we discussed the programme, that her son had dressed as a girl for about three years, but only in his bedroom or when there was no one but she and him in the house.

Her story was similar to mine with Georgina. She had found him wearing her underwear and he had become upset. She saw no harm in letting him play a dressing-up game, but it slowly evolved into a situation where he was wearing girls' clothes and night-wear, which she had bought for him, and using a girl’s name. I’m ashamed to say I did not admit to Mona about Georgina’s life with me. I don’t know why. Even after all this time I still feel guilt.

Which brings me to the last question: since Mona and I were both mature women alone with boys of a certain age, is that a factor in this phenomenon?  What I mean is, do women who are alone, and who maybe crave female companionship, project their desires onto the young boy who may be with them? Or is there some other explanation? Is it a fortunate coincidence maybe, that a young boy who wants to share the feminine world should find himself in the company of a woman whose needs for female companionship reflect his needs?

One last point: while Georgina clearly enjoyed herself and reveled in her time as a girl, I enjoyed it more! I really mean that. There was something special about our secret world that fascinated and terrified me.

This is not a story about humiliation or forced petticoating, it’s about a special relationship that developed between a lonely young boy and a lonely adult woman. I’d like to know if there are other women out there who have had similar relationships. I suspect there are thousands in Scotland alone.
Yours sincerely,

Hester

P.S. please reply by email or in your net magazine.

The harm that has been done by the pomposity of child psychologists over the years beggars description. There is no evidence whatsoever that allowing a boy to dress in girls' clothes will predispose him towards homosexuality. It was simply the 'political correctness' of the time, and like the authoritarian idiocy of political correctness in all times, you were meant to just accept it as a fact, and not open to the discussion or disagreement of 'nice' people.

No, you were not wrong to allow and encourage George to fulfil his desire to dress as a girl. Those desires are ineradicable from an early age, and to make the child feel guilty or abnormal, as most adults would have reacted, would have been the worse way to react.

Nor where you wrong to stop it after unfortunately hearing that wretched psychologist on the radio. You were a young woman, and your teacher training had probably informed you that psychologists were people who should be taken seriously. Under the circumstances you were simply behaving in the best interests of the child, as you had been informed of them at the time. You have no need to feel guilty, you have my assurance on that. Ironically, the person who should be wracked with guilt about spreading such misinformation, the psychologist himself, probably feels none.

You may well be right that a young woman alone in an unfamiliar setting might enjoy the company of a boy with feminine inclinations. But I cannot be sure - I am not a psychologist, but merely a sensible, down-to-earth woman trained in sciences a good deal more rigorous than psychology will ever be.
Susan