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I never wanted mother to know, that I didn’t hate her dressing me in her clothes as much as I did. At the same time I become ever uncomfortable with how in the solitude of my bedroom, I was coming to dress up in secret. Uncomfortable with the idea, that maybe, I didn’t dislike at all any more….. maybe that I was even coming to…….. like it……

Over time, I increasingly worried how mother’s love of dressing me in her clothes, was changing me. On one of our weekends away together, where mother would normally pack my suitcase full of dresses and skirts, and I would spend the weekend negotiating the world as a girl, it would be the first time I found myself looking at scantily clad girls (girls which a boy should find overwhelmingly sexy), in a distinct way in which I knew only girls supposed to. Disturbingly, as distinctly gross.

It wouldn’t be long until I would find myself thinking about another thing, in a distinctly female way which would mortify me…. men. Their bulges, their naked bodies, and their members.

Few things would be so profoundly unsettling and make me so vulnerable and insecure about myself, than when mother expertly dressed me in her lingerie, wig and makeup, making me look so convincingly like the kind of girls that boys supposed to obsessively lust over.

So vulnerable I was, that I found myself not only open to, but entertaining erotic thoughts that no boys were supposed to have. Thinking the kinds of thoughts which only girls were supposed to have about men, I would experience the most powerful orgasms of my young life, that would have important implications for the nature of my developing sexuality, decisively drawing me to my mother’s Playgirl magazines, instead of my father’s Playboy magazines

Oh boyhood. How once it would have been unimaginable to be anything other than one of those cuing up. Soon enough, I would come to look at something like this and imagine how anyone could not want to be in her place.

Compounding his anxiety, knowing how in his normal life, he no longer thought about girls like a boy supposed to, when he was made up glamorously in his mother’s lingerie, he no longer feared thinking and feeling the kinds of things that only girls were supposed to. 

He wanted sex with men, and he wanted it so very badly.

The first times that mother dressed me in her lingerie, were understandably distressing and confusing to the adolescent boy I was. The new sensations I found myself feeling….. The thoughts and dreams induced, that couldn’t be farther away from the kinds of things which boys were supposed to think and dream about. 

Over time I began to fear that I was becoming too used to it all, and that it would change me. No longer fighting against mother when she wished to dress me. No longer fearing the thoughts and dreams that I found myself experiencing at night.

I never could have imagined, that there would come to be a time, much to my mother’s delight, that I would dress of my own free will. That first time it happened, something changed within me. That night, for the first time I touched myself to the thoughts which once so disturbed me. and I knew then, how long I had slowly been sliding into bisexuality, that my worst fear had finally come to pass. 

Beyond bisexuality, then, I knew I had descended, irrevocably and forever into homosexuality. I had finally become a fairy.

The evenings spent made up by mother, in her most glamorous lingerie, it does something to a boy. 

Finding himself in utter delirium, thinking thoughts he never imagined he would entertain. Thoughts not of girls, but of things forbidden, of unparalleled pleasure. Thoughts that are only meant for girls. Thoughts of……

…. Men………….

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Very few things would come to be so symbolic to me, in how I would change in my early years, than Playgirl magazine….. 

….of gradually growing out of the things I used to like. The things all the boys liked. And slowly discovering… getting into the things that the girls were only supposed to like…. things as boys, we always had dismissed and mocked, but there I was, my juvenile desire for women being eclipsed by images that I never would have imagined I would have, and never imagined that would be so sexy. Soon, thoughts and images of girls would be gone from my dreams, and in their place, the things girls dream of. Oh how the dreams of my small delicate body, in bed with groups of large muscular men, did such things to me. What more pleasure could a boy have????

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It was always like night and day, the difference when we dressed as our femme alter egos. How without inhibition, we were free to see men, how they really were, how girls were only allowed to see them, as sexy like nothing else in the world.

How we boys, who were so sure in our attraction to girls, with a bit of makeup, would so easily forgot all about girls.

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“After the hysteria with Greg’s announcement of his experimentation with bisexuality, get the low down from the boy himself, as the unimaginable has happened… “

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Reminds me of my boyhood. That curiosity which a sensitive boy knows of, which compels him to look at the things he knows only girls supposed to look at.

That confusion and anxiety which follows, when you can’t help but stare entranced, as your sexuality is irrevocably turned upside down. 

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When you think such sexy thoughts, there is no going back!

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