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Q: My Husband Likes Wearing Women’s Underwear. What Should I Do?

My name is Isobel, and I’ve been married to my husband for nearly 25 years. Our two children are grown up, and they’ve moved out of the family home — giving me and my husband more free time than we’ve ever had.

Crossdresser with red bra in his mouth

I was really looking forward to our future together, but that all changed when I discovered photos of my husband dressed as a woman.

I was absolutely devastated when I found those pictures — I cried for days afterwards. Eventually, I confronted him, and asked him how long he’d been doing it. To my horror, he told me he was dressing in women’s clothes before we even met. I then asked him if he’s gay, and he told me he wasn’t.

After a few weeks of not having any sexual contact with one another, I eventually suggested he dressed up for some role play in the bedroom. I really didn’t want to do it, but his eyes lit up the second I suggested it. We had sex, but I was uncomfortable throughout. I’m convinced my husband is gay… what should I do?


A: Don’t confuse homosexuality with cross-dressing

You and your husband are still together, and I’m assuming that you’re both relatively happy. The fact that you’re still having sex and role playing together is a good sign. For these reasons, it is highly unlikely that your husband is gay.

There are many reasons why men like cross-dressing, and not all of them are sexual. For many men, they dress this way to escape the reality of life for small periods of time. You’ll only know why your husband does this by asking him.

Cross-dressing is surprisingly common

Cross-dressing is surprisingly common among married men. In some cases, wives help their husbands with makeup and clothes, so please don’t think there’s anything strange or perverted about your situation. However, you do need to be honest about your own feelings.

As long as your man isn’t doing anyone any harm, there’s nothing wrong with dressing up for fun. However, if you’re experiencing emotional anguish because of the situation, your husband needs to respect that. The only way you’ll be able to work out how you move forward is by communication.

Cross-dressing provides men pleasure or relief

There is always a good reason for men dressing up as a woman. It may be that your husband gets a thrill from the experience — whether that’s sexual or related to the creation of an alter-ego. However, there is a chance that your husband is creating a new persona in order to escape some form of mental anguish.

There are many potential reasons for your husband’s love of cross-dressing, but if it gives him pleasure or the chance to escape, then what’s the harm?

Get involved

Your partner has hidden his cross-dressing secret from you for decades, so it’s very unlikely that he’ll stop now. And why should he? This is obviously something he’s very passionate about, and asking him to stop might cause resentment and anger.

If you can find a way to accept your husband’s cross-dressing, that’s a great start. But you have to both agree some ground rules. For instance, you might both decide to keep this side if your husband’s personality a secret. You might also want to agree that your husband tells you every time he decided to cross-dress.

Once you’ve made your peace with your husband’s behaviour, there will probably be a period of getting used to things. But after a while, getting involved could be good for your relationship. This could involve role-play, or it might involve helping your husband with his transformations. Eventually, you may both be brave enough to introduce your husband’s alter-ego to the outside world.

There may come a time when you want to find a fetish partner on an adult dating site to join you and your husband for sexy fun. Just make sure you’re honest about your husband’s proclivities from the outset.

Work out what you’re comfortable with

Most men want to keep their cross-dressing a secret. Some will limit their transformations to underwear, and others will create a completely new female character. Find out what your husband wants, and decide whether or not you can live with that.

This is going to be a period of discovery. If you keep an open mind about things, you’ll both eventually reach the stage where you’re completely comfortable with the situation. But if there are any doubts or grievances, you both need to communicate them immediately.

If you really can’t live with the new situation, you may run into some serious relationship issues down the line. Some women agree to turn a blind eye to their husband’s cross-dressing, but this course of action rarely ends well. Ultimately, you and your husband may need to compromise. If neither of you are willing to, however, I’d recommend marriage counselling.

I’ve read hundreds of similar stories over the years. While some relationships breakdown, others actually improve. If you can both find a way of integrating cross-dressing into your relationship, you could end up happier than ever before.

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