Interview with a Crossdresser

I have previously interviewed a young Australian woman doing a graduate degree who wishes to adopt the “bimbo lifestyle”. I am interested in interviewing people living unusual lifestyles.

For example, there is a young man who works at our local hairdresser who wears feminine clothing and makeup (although he does not change his voice). He has “gay voice” so I assume he is a homosexual. He is perfectly upfront about his behaviour. Which is not to say that he tries to give himself the appearance of a female chest. Perhaps having to work as a hairdresser all day might make using a fake female voice and wearing fake breasts impractical.

Anyway, I would like to interview him about his lifestyle one day. But one has to be tactful and wait for the right moment, if it ever comes.

I do have another contact who is a crossdresser, an older man. He has been dressing for a while and usually adopts the persona of a middle-aged lady or “matron”. He claims that he passes OK.

Here is my first interview with this man, whom I will call Janet. As time goes on I hope to add more to his account – in the same way as I was able to do with the Australian “bimbo”. In other words, follow up with supplementary questions.

Q. (Me): So, what do you do?

A. (“Janet”): I dress up to look like a believable woman of about my age. Middle-aged. I want to be seen as just another housewife going about her business.

Q. (Me): How does it make you feel?

A. (“Janet”): It is fun. I find it intriguing and satisfying and relaxing, although you have to use common sense.

Q. (Me): How do you want to be treated when you are dressed up?

A. (“Janet”): As a housewife, like I said. I want men in shops, supermarkets to speak to me and see me as just another female customer. To be honest, I want to be made to feel a bit feminine, find out what that is like. I enjoy being patronised a bit.

Q. (Me): How do you manage to “pass”?

A. (“Janet”): I am not sure, but I seem to. I have thought about why. I think it is partly because I wear low shoes so my male height is not such an issue. And I wear a bit of makeup and usually long skirts and blouses and a bit of age-appropriate jewelry. Earrings probably help. You can get some that look for all the world like your ears are pierced like a real woman. Also, I have a round face and fairly smooth skin. Men with long, masculine faces sometimes have trouble looking right. But I seem to manage it. After all, people tend to see what they expect to see. Also, I make myself a very matronly [laughs] bosom using balloons filled with water in a normal bra, and that probably does a lot to convince people. Also, I do housewifey things, like going to a supermarket midmorning and buying typical items.

Q. (Me): What do you do about your voice? And can we talk again?

A. (“Janet”): I aim for a sort of ladylike English sound, which goes with my look. It seems to convince people. At least so far. And yes, we can talk some more if you think of more questions.


3 responses to this post.

  1. Posted by Julian O'Dea on March 26, 2015 at 4:23 am

    “Janet” described some more of “her” adventures to me. He says he is still passing OK in women’s clothes, and he interacted on one trip out dressed “en femme” with three young men and two women (one younger and one an older Asian lady) at the supermarket and at the McDonald’s drive through without being “clocked” as they call it. That is, they apparently believed he was a real woman.

    He also walked around in public and went to a woman’s toilet for the first time, as transvestites are advised to do.

    His only negative feeling was that people were seeing him as too old; and he blamed this on 1) wearing old lady type “floral” blouses, 2) wearing short sleeves rather than long, and 3) having too big a fake bosom, which paradoxically makes him look older and very matronly. He is happy with his look below the waist, a long narrow skirt and court shoes with black hosiery. And he thinks his make-up is OK.

    He plans to go out with a much smaller “bosom” on his next outing. Maybe even go for a slightly small-breasted, more realistic look. He says that he doesn’t know if real women get used to having a female chest, but he finds he is very often aware of the weight and motion of his “breasts”.

    I am rather amazed he has had such success really. I can’t believe it is an easy thing to pull off, no pun intended.

    I did ask him if he noticed that he was treated differently as a “woman” than a “man”. He thought people were possibly kinder to him with a hint of condescension, but that might be more because of his presumed age than his apparent sex.


    • Posted by Julian O'Dea on March 26, 2015 at 6:48 am

      I suppose there are a few possible reasons nobody notices that the matronly woman is actually a man dressed as a woman. One is simply that most people don’t look too hard at middle-aged people, men or women. They are not very interesting, unlike pretty young women or handsome young men. Another may simply be that people do not see what they are not looking for, as this classic video shows dramatically:


  2. Posted by Julian O'Dea on March 28, 2015 at 4:18 am

    Another report from “Janet”. He is still having little trouble in “passing”, although when he went to a local shopping centre he did notice one or two women giving him a funny look. He decided they might have thought he was overdressed; so he went to a women’s toilet and removed his earrings!

    I asked him how he felt, walking around and shopping and eating dinner in a small Asian restaurant. He said, generally serene and content, but a little nervously feminine. He thought people treated him well, and that he probably looked like a real woman of his age, namely late 50s.

    He had one embarrassing moment when a man pointed to the fact that the hem of his long skirt was stuck in his car door as he drove.

    Hats to set off his relatively short hair and large male head could, he thought, be replaced in cooler weather with scarves over the head. Or maybe a “Russian winter hat”.

    He found that red lipstick and some blue eyeshadow created a good effect.


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