REMEMBER that Agony Aunt idea I had?

Well it’s come to fruition my friends and I couldn’t be more thrilled. (Or nervous.)

I put the idea out there and the emails have come. The first one that landed in my inbox was this one. I found it hidden in my spam box and when I read it, I don’t think I breathed until I’d come to the end of the words.

It took my breathe away.

Thank you to the brave person who sent it in (you know who are) and here are my thoughts which I truly hope will help. X


Dear Kate…

I write this e-mail with mixed feelings as to whether it’s a good idea or not. The reason I have been hesitant to send you this e-mail is that while I follow and admire your website for it’s championing of feminism and all things relevant to a 21st century woman, I am in fact a man – at least I am 99% of the time, hence my reason for writing!

Ok, here goes. I’ve been a crossdresser/t-girl/tranny (not sure what the PC label is these days) for years now, and it was something I was open about with my then-girlfriend (now wife) within the early stages of our relationship.

Initially, she was very supportive about it. In fact it was so staggering how well she took it (I’d even say enthusiastically!).

She would shop with me for clothes, help do my makeup, take photos of me made over and we would even share intimate moments to round off the photo shoots. We even once went out to a t-girl club on a weekend away to London once. 

The day after that however, which was several years into our dalliances, she broke down in tears telling me that secretly she’d hated it all along and so while blind-sighted and I suppose feeling a bit rejected, I immediately stopped out of fear I was causing her pain and that I’d lose her.

Months passed without me dressing, but the urge to do it was still there. I eventually began doing it secretly when home alone, or when she would go to bed early on nights she was tired. This has been the situation for 7 years now, but I must admit to feeling so unfulfilled and feel the topic is EXTREMELY taboo now between us.

I really don’t know what to do on this issue. I’ve tried burying the urge, but I’ve even found the desire popping up in my dreams despite my best efforts to block it out. In every other way, I am happy in our relationship (we’ve even since started a family). The fact is though that I really miss dolling myself up as Tiffany. I loved the ritual of the transformation and I got such a thrill turning heads of both guys and girls in that club that one time. I feel that I was just on the cusp of exploring my t-girl side and then the reset button was pressed suddenly.

I have kept this in for so long, to the point that I’m not now sure if I am being utterly unreasonable or if I should fight for something that I am starting to accept is ultimately a fundamental part of who I am.

As the topic is so taboo, I am considering opportunities to be Tiffany again but am a bit stifled in how to do so, and on a moral level whether this is dreadful deception? 

Thanks for listening to a confused 99% guy / 1% girl!

Tiffany x


Dear Tiffany,

Should you fight for something that is absolutely a fundamental part of who you are? Well the easy answer to your question, of course has to be YES.

One hundred per cent yes, with cream and cherries on top.

Why? Because you are who you are, my friend. You are who you are. We’re all weird and wonderful, in our own unique ways, so if Tiffany is a part of you, then she is a part of you. Whether you chose to lock her away or not.

To deny her presence would be to deny your full existence. Far too many people spend their lives doing that. Please don’t be one of them.

You tried to ‘bury the urge’ but Tiffany doesn’t seem to want to just disappear quietly does she? She’s demanding and kicking and screaming to be remembered. No two ways about it, she’s a woman who isn’t going to stop until you’ve given her breath.

Let’s go back to the beginning…

The very fact that you were honest with your wife, at the start, is to be commended. You demonstrated great courage and it shows me exactly the kind of person you are. And, how important Tiffany is to you.

You say your wife was supportive at the beginning, enthusiastic even, so what changed? Do you genuinely believe she truly hated all of it and was just going along to please you?

Or could it possibly be that the trip to the club in London was just too much for her? That going ‘public’ with you as Tiffany that one time was more difficult and traumatic, than she could have imagined?

I ask these questions, because it’s important I think to really try and figure out what happened here as clearly you have a woman who loves you greatly.

A woman who didn’t run away when you told her the truth. A woman who stayed and supported you. A woman who not only tried to accept Tiffany but even went so far as to helping you bring her to life.

Her love for you is evident. But it appears from her tears, that while you may love Tiffany, she clearly does not.

On hearing her pain, you chose to do what any decent man would. You chose to try and take the pain away. And you did so by trying to deny Tiffany’s existence and doing what you thought was ‘right’.

But I ask you, who is it right for?

It’s certainly not right for you. Nor do I think it’s right for your wife.

You say that you’ve been dressing in secret for the past seven years. Do you really think your wife doesn’t have an inkling that this may be the case? I’d be surprised if she doesn’t know or at the very least already suspect that Tiffany is still around, even if she is out of her sight.

How could she think otherwise after your history?

You say that talking about Tiffany ‘feels’ taboo but I urge you to reconsider. Because my feeling is, that if you don’t talk to your wife about this ‘fundamental’ part of you, it will eat away at you.

That all the unspoken things you dare not say will end up destroying the evident love in your relationship and force you down a path of deception, that you clearly don’t want to take.

You need to talk. That is my thought. You managed it years ago. You can do it again.

There may be tears. And it will probably be painful and embarrassing and all kinds of awkward but really what choice do you have?

Sure you could carry on living a lie I guess. Dressing up as Tiffany on those rare occasions and carrying on as if everything is tickety boo. Many people do manage to live double lives, in all sorts of ways and seem happy enough doing so.

But you don’t sound like that kind of person to me.

And what would happen if your wife discovered the truth? What then? How would she feel? And how would you feel about that?

By keeping Tiffany a secret, you are making her into someone naughty, seductive, mistress like. But mistresses can ruin marriages and destroy families and it’s clear you don’t want that to happen.

So there’s only really one thing for it.

You need to bring her out into the open and have that difficult conversation that you know, deep down, you need to have.

Maybe together you can come up with a compromise. Maybe together you can find a way of letting Tiffany exist without her causing your wife discomfort. Maybe you’re not giving your wife enough credit. Maybe she has no idea how much you are suffering.

All of these reasons (and more besides) is the very reason why you need to talk.

Your wife has already proven herself to be kind, supportive and non judgemental, so have faith. Maybe it will be possible for her find a way to try and accept Tiffany again.

Perhaps not as a loved one. But maybe, one day, as a necessary friend.

The conversation may not go the way you want it to, you need to prepare yourself for that, but you owe it to all ‘three’ of you, to at least try.

So yes, fight my friend. Absolutely. And be brave.

It’s time to be 100 percent YOU.






If you’ve got a dilemma – any kind of dilemma from motherhood to marriage, style to careers- that you’d like some ‘non expert’ advice for, please feel free to drop me a line at and i’ll do my very best to help.

I’m not a trained professional but I do have a very kind pair of ears.



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