How to tell your girlfriend or wife that you are a crossdresser i.e. a crossdreamer

by Felix Conrad - Clinical Philosopher on June 17, 2014

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Attention: this post is in response to an e-mail request. It is about telling your girlfriend that it turns you on to dress like a woman. It assumes you understand that ‘crossdresser’ and ‘transvestite’ are misnomers for the real force at work: crossdreaming – arousal at the idea of oneself as a woman.

how to tell wife

Dear Felix,

You repeatedly state in your books that we have a moral obligation to inform a new spouse or girlfriend that we get turned on by dressing like and having sex as a girl. Please could you tell me the best way to go about telling my new girlfriend about my crossdressing and other related desires.

Anonymous.

Dear Crossdreamer,

This is a complex question. While you do have a moral obligation to inform her that she’s not the only one who likes to get dressed up and penetrated, you must also remember that she has a moral obligation to keep that information confidential…

…INCLUDING WHEN YOU BREAK UP – EVEN IF THAT BREAK UP IS BITTER AND TWISTED…

If you can’t be sure that she’ll keep your secrets then think twice before telling her. Also, bear in mind that most people – men and women – share the intimate details of their sex life with best friends and even their not so best friends. Even if you stay together the rest of your lives – it is possible that she will tell her closest confidants, including her mother, best friend, and wider circle of girlfriends; human beings cement friendships through self disclosure and the trading of secrets. In fact, there’s a school of philosophy which says that once you tell a secret you should consider the secret exposed because it’ll inevitably be divulged.

Of course, this throws up two questions…

1) Why are you ashamed of your sexuality?
2) Why would you have a relationship with someone who you didn’t trust?

However, those are questions for another day. We will assume in this article that you’ve decided to tell your new girlfriend you’re a crossdreamer i.e. a man who gets turned on by thinking of themselves as a woman.

What’s the best way to tell your wife you’re a crossdreamer / crossdresser?

Step 1: find out if she is gender variant or has unusual sexual preferences.

You have a secret about your sexuality and she has no idea, but it might be mutual. The statistical chances of your new girlfriend being bisexual, gender variant or having a sexual preference for masochism, domination etc. are high. This is important because you might spend time and emotional energy on elaborate explanations when it turns out she’s just as variant as you, and all you need to do is exchange kink lists.

I know a happily married couple with two children who appear heterosexual, but in reality she prefers girls and he’s 50-50 bisexual. Both know about their preferences and allow each one (on special occasions) to have sex with other partners. During the process of courting they exchanged sexual histories and everything was out in the open from the beginning.

STEP 2: Choose the right moment and the right time, and then have ‘a chat’.

Let’s presume that step 1 reveals no hidden kinks, and that your new girlfriend is the epitome of heterosexual/gender normative behaviour. How do you tell her you’re a crossdreamer?

The first fact to remember is that there are no facts. You’re going to need some basic sexological or psychological framework to explain your crossdressing etc. but there is no scientifically proven narrative for such behaviours. The reason why a crossdesser gets turned on by female attire is extremely complex. Fortunately, though, you can use this to your advantage and stress the narrative which will be most amenable to her personality.

You have two options…

1. A gender variant approach.

With this explanation you basically tell your wife that you are transgender, but remind her that ‘transgender’ is not a word for transsexual people who transition and have surgeries, but an umbrella term for a variety of gender variant behaviors. You explain that while such discourse is extremely unpopular in transgender circles, the fact is that there exist degrees of the transgender condition and you are ‘mildly transgender.’ Therefore, she never has to worry about transitioning.

You then go on to explain that the principal dimension of personality where your transgender side emerges is in your sexuality, and while you enjoy sex with your girlfriend and will always be able to provide the goods (so to speak) you do sometimes need to feel female in sexual contexts. This may take a variety of forms that include crossdressing, anal stimulation or roleplaying.

If she wants to know why the transgender side comes out in your sexuality and not in other areas, then you will have to read my book – Transgender, Fact or Fiction? – for an explanation from the perspective of evolutionary biology.

2. A sexological approach.

With this explanation you use a twentieth century method and say…”I have a ‘fetish’ for dressing like/behaving like/ having sex like a woman.”

Sorry, there’s not much more that can be said. This is essentially an explanation that throws yourself upon her mercy. You employ a narrative of fetishised sexualisation and the rest is up to her.

Conclusion.

As you can probably tell, I favor the first explanation. I repeat: nobody really knows why crossdreamers and crossdressers do what they do, so you have no moral obligation to give the most accurate explanation because we don’t know which is more accurate. If you deeply feel that your crossdreaming is a sexual phenomenon then remember that there no such thing as ‘a purely sexual phenomonon’ (sexuality both feeds and is fed by the personality). Furthermore, even if there was such a thing, there is a strong case for saying that our society is not yet evolved enough to accept and talk about such phenomona without recourse to moralizing terms such as ‘fetish’ – therefore, better to explain it in other terms.

Do I really have to tell her?

Contemplating the reality of telling your wife, you may backtrack and question the moral obligation to do so… so let’s just re-examine the issue a little.

If you are fully aware that you are a crossdreamer (i.e. your desire for the feminine goes way deeper than crossdressing) and you start a serious relationship without telling your girlfriend… well, that really sucks. Why? Because it’s well known that even if you’re happy to be a man now, most crossdreamers go through a gender crisis eventually, and if one day you’re going to have to inform your now wife that you are transgender she’s gonna wish she’d known that before you had two kids and you later decided to become ‘mum’ rather than ‘dad.’ Cross gender arousal is a pretty good predictor of a late onset transgender crisis and she needs to know that your sexuality is crossdreamer.

Exception

Personally, I don’t think there are exceptions (except maybe in Islamic countries). FOR YOUR OWN GOOD AND HERS YOU SHOULD LIVE AUTHENTICALLY WHICH MEANS BEING ‘OUT’. However, if you push me to find an exception you could possible get away with it if you are (1) certain that you will always be able to satisfy her sexually and won’t start habitually using porn instead of habitually servicing her needs and (2) you love who you are and the body you are.

For further advice about living with the crossdreamer sexuality, read my books on Amazon or in our shop🙂


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{ 1 comment… read it below or add one }

Carlee November 4, 2016 at 12:17 pm

I really wish there were more areiclts like this on the web.

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