Anna isn’t my real name. It’s a girl’s name I chose pretty much at random – from a Page 3 girl as I recall. You see I’m a man that for some undefined reason derives considerable pleasure in transforming himself into a woman. This change is entirely on the surface and does not extend to my mind, I am basically just a man in a dress. It’s a hobby – an odd one perhaps – but through years of practice I think I’ve gotten pretty good at it.

Below are two examples from two different periods in time.

2005 and 2013



I can’t be certain for exactly how long I have been doing it. I have a rather vivid memory from sometime in the mid-80’s of trying on a pair of my mother’s heels. It’s fair to say I was hooked instantly. I’m sure my story from then on is similar to everyone else’s, raiding the washing basket for clothes, trying out different things and building up a sense of style and self. Though I feel I should point out early on that I do not desire to become a woman. This is important though makes more difficult to explain or justify (even to myself) why I do it. I just really enjoy the process and especially enjoy the end result.

Cross-dressing is the biggest secret I’ve ever kept and I indeed managed to to hide it successfully for many years. It pales my other secrets into comparison, such as they are. I would love not to hide it but I feel most people are not ready for that bombshell. I did eventually decide to confide in my wife but I’ll admit it was mainly so that she didn’t find out in some other unfortunate way. There was always the possibility no matter how careful or diligent I may think myself. She was genuinely surprised! I had been mulling it over and building up to confessing for a week or so but I still felt sick the moment the words left my mouth. I told her I’d try my best to answer any questions she had about it as I was not sure where to begin. Amongst her major concerns were ‘was I gay?’ and ‘do I want to become a woman?’. I assured her it was a most emphatic negative on both counts but I suppose even then her fears and worries may never fully be at rest.

I contrived to arrange a meeting of sorts, my wife had offered to give me a make-up lesson. I accepted and one night a while later when my little girl was in bed she set to work. I learnt about moisturising but to be honest I didn’t learn anything else. After this I really wanted to get dressed up to show her how seriously I take my look. I donned my smartest (and I’ll admit my most low-cut) black top, black pleated skirt (above the knee of course), black tights and my black 4 inch heels. I was a vision in black, very existential! She had the good grace to say I had nice legs but it must have a little difficult to deal with. Effectively I feel that I was threatening her femininity and since then she begun to wear more skirts. At Christmas that year she bought me a top as a little extra present. It’s a bit like something that Florence Welch would wear so I like it (though haven’t worked it into a definitive outfit yet I’m afraid). I do appreciate the gesture and she also bought me a little black stretchy skirt last year. It’s one of my favourites because it’s quite comfy and a little bit sexy. It certainly makes me more confident about buying her clothes now, especially dresses. We’re certainly more likely to talk about fashion these days but I can’t be certain if this has brought us closer or not. I hope it has as it was one of the main motivations behind my confession.

My wife calls it my ‘thing’ and sometimes it’s my ‘habit’. It’s not in her mind as often as it’s in mine so she can be taken aback when it’s remembered. If I’ve been left alone for a few hours when she’s out and I’m clean shaven upon her return I’m likely to be asked if I’ve done my thing. Very astute. It is often the case, as much as I try not to do it as regularly. Sometimes she’ll ask what I was wearing and I sheepishly oblige with a description. I like it when she’s curious.

Here are a couple of other pictures from the last year, both dresses belonged to my wife and I acquired them during a clear-out of her wardrobe.



2 thoughts on “Confessing

  1. Penny Clare

    Hmm. Sounds very much like me.
    I remember very clearly (far too clearly) having ‘the conversation’ with my wife. I forced myself to have it for much the same reasons as you did.
    Fortunately she didn’t divorce me, which I was very afraid of. Getting help with make-up is little off the radar for me at present and sadly most of her clothes would not fit me… which is a pity. You are lucky!
    I think it is really hard for a woman to understand why a man would want to look like a woman. Which is a pity because they do it all the while and so well. Why would one not want to look like them, at least some of the time?

    1. Anna Secret-Poet Post author

      Thank you, it’s great to hear from you! I didn’t think people went that far back on my page these days. Only some of my wife’s clothes fit to be honest, she had a clearout the other week and I got a few things; black leggings (very comfy), short denim skirt, a green top and a couple of nightdresses. Luckily those did fit okay, it’s these damned manly shoulders that prevent others fitting better 😉
      Anna X


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