Disguised in Skirts (Part 3)

It was morning break when they arrived and Roger just wanted to sink through the ground as he walked down the corridors holding his mother’s hand – every single girl seemed to be staring at him, guessing his guilty secret.

Miss Jacobs was a tall darkly attractive woman wearing an elegant pale blue suit with a silk tie-neck blouse. She came round her huge desk staring at Roger as she came.

“My God! Is this really a boy?” She asked. Roger blushed.

“He was the last time I looked”, my mother laughed.

“He’s very convincing – very convincing indeed. I would never have guessed. What do you call him?”

“Rita. Say how do you do, Rita.”

“How do you do?” Roger muttered.

“Very well thank you, Rita,” Miss Jacobs smiled.

“Well, what do you think?” his mother asked.

“No problem, Annie. No problem at all, providing Rita is prepared to play her part providing she is prepared to behave properly as a girl – no fighting or anything like that.”

“There will be no problems, Hazel. I give you my word. Right, Rita?”

“Yes.” Roger whispered. What else could he do?

The next day was spent buying the school uniform – green gymslips, green gingham summer dresses, green school coat, green knickers, white blouses and socks and two pairs of simple flat heeled black shoes. They did not, of course, have to buy any sportswear.

As soon as they got home Roger was made to parade around in his new school uniform. His mother was delighted with the whole outfit. Roger groaned inwardly as he realised that in three and a half weeks he would be wearing it everyday. He had tried several times to convince his mother that the danger of his father finding them had long past – they had been safe for nearly a month, but she would have none of it.

And so it was that Roger gradually learned to be a girl – to be Rita in more than just a name. His first few weeks at school were a nightmare as he tried to fit in with his giggling feminine companions, as he learned not only the normal school lessons but found himself learning how to cook and dance. But he was and intelligent lad and, like most children, extremely adaptable.

Thus he slowly came to accept his new life as a girl.


It was the best part of two years before his mother eventually felt it was safe for him to discard his disguise. By this time he was even wearing a lightly padded bra to suggest the gentle swelling of female breast to his school companions.

Again, although, Roger never actually told me, I got the impression that her mother, and indeed even Miss Jacobs, was both very sorry to see Rita disappear.

As for Roger, it was a traumatic experience for him. For two years he had been conditioned to be gentle and feminine. He had grown to feel completely at home in dresses and skirts and had made a number of close girl friends. He had learned to look upon boys as the opposite sex – creatures to be flirted with – smiled at, but kept at a distance. Suddenly all this life was over.

All the close girl friends he had made at school he would never be able to see again. The last two years were to be wiped out.

In fact Roger ended up having a nervous breakdown and was in hospital of nearly three months. When he came out he had to relearn how to be a boy – to go to a boy’s school – to play rough games.

Not surprisingly, it was a disaster. All the other boys laughed at his ingrained feminine characteristics. Eve his speech patterns had become feminised. He only had to open his mouth in the classroom for the other boys to be mocking him – blowing him kisses or calling him a poofter. Gradually he withdrew more and more into himself, only happy with the few new girlfriends he had managed to make. But, unfortunately, he was quite unable to share the little feminine intimacies he had previously with girls when he was also one.

It was well over two years before he was able to come to terms with his role as a boy again – to eradicate most of his feminine characteristics, but he was scarred for life, condemned to live the rest of his life in a sort of halfway house.

His mother was unsympathetic to his predicament and happily allowed him to dress as a girl at home in the evenings.

It was not that he wanted to become a woman; he was, in other words, not a transsexual. He had simply become a dedicated transvestite who enjoyed wearing women’s clothes as often as possible – enjoyed being able to behave like a woman – to be gentle and feminine as he had learned to be during those two years when he had been Rita.

Eventually he qualified as a civil engineer, of all things, and got offered a good job by a firm in Manchester, which he accepted.

Two years ago his mother met and married a somewhat older American architect who had come over to work in Manchester for a year. At the end of the year they had both returned to America, leaving Roger the sole occupant of the little flat in Didsbury, where he still lived.

By now everyone in the flats around had realised that he was a transvestite and seemed happy bumping into him on the stairs when he was dressed as a woman.

For now his life seemed to have divided itself into two distinct areas – the daytime when he worked as a very successful male engineer, and the evening when he became Rita again – the girl, now grown up, who had been created out of the fear that his father would find him and make him go home.

Roger – or rather Rita had not heard of our little parties at the Dog & Partridge, so I decided to take her along with me. She proved to be the centre of attraction, not only because of her gentle charm but also her extraordinary natural femininity, which most of the other guests watched with envy and fascination.

But, of course, what they did not know was that she had lived as a girl full-time for two glorious years. That was something nobody could take away from her.

The End

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