Dear Richard Madeley: ‘Trying on my girlfriend’s clothes turns me on – should I tell her?’

Dear Richard,

I don’t know whether you are comfortable dealing with sexual problems and I’m feeling a bit weird about admitting I might have one, but really this is about how to have a conversation – or whether to have it at all. 

About six months ago I was kicking around the flat I share with my girlfriend, supposedly working from home, and I tried on a couple of her clothes. I had no sudden revelation about wanting to transition or anything like that – but what did happen is that I became really strongly aroused.

I put everything away again and tried to put the genie back in the bottle but I couldn’t. Since then it’s been an occasional ‘solitary vice’, if you know what I mean – but it’s intensified my attraction to my girlfriend and our physical relationship is much more energetic than it was.

I don’t want to dig into the psychology of this, or rather I guess I am afraid to, but what’s concerning to me right now is that I don’t want her to accidentally find out, think I’m a pervert and run a mile. 

But I don’t know how to tell her. Meanwhile I am trying not to feel shame about this ‘kink’ – but I can’t shake the feeling that I am hiding something from her. Do you have any advice?

— Anon, via email

Dear Anon,

I’m perfectly comfortable answering letters about sexual issues, so don’t worry – no problems there. However, I’m not an expert in this field, so like a GP presented with a case above their pay grade, I’m going to refer you on! But we’ll come to that.

I think it does you great credit that you want to be open with your girlfriend about this. Assuming you think you have (and want to have) a long-term future with her, honesty is absolutely the best policy. Why? Because of two things.

Firstly, if you keep this to yourself it will become an ever-growing preoccupation; your secret, like all secrets in close relationships, will gradually grow into a boulder that stands between you.

Secondly, it’s practically inevitable that your girlfriend will find out anyway. She’ll come home unexpectedly early one day and find you in her things. Or you’ll get careless and leave a tell-tale sign that you’ve been wearing her clothes, e.g.: ‘Why does my skirt smell of your aftershave?’ So you have to tell her.

Now. I noticed three red flags in your letter to me – the words ‘pervert’, ‘kink’, and ‘vice’. Please, please, Anon – stop judging yourself. You’re doing nothing wrong: nothing immoral or illegal. Human sexual desires are pretty much infinite in their variety and range, and cross-dressing is hardly among the most uncommon. You are not alone; yours is merely one fetish among many. You didn’t choose to have it. For whatever reason, it found you.

So to the referral.  Here’s what I advise. Before you talk to your girlfriend about this, seek out a sex counsellor or therapist and lay things out to them. They can give you a much better perspective than I can on what’s going on here, and advise you on how to broach the issue to your partner.

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