Ask Hannah!

Helloo! I’m so glad i found your website.

I stumbled across something on our computer the other day and think my husband wants to crossdress. He has ordered a dress and a bra and inserts. Now I know and I’ve tried subtly approaching the conversation, but he isn’t been open and honest with me. I know it must be so difficult for him, but I thought he would know that I want him to be himself, whoever or whatever that looks like doesn’t bother me. But I worry about the lying around it, how can I facilitate a conversation that will allow him to be open.

I would leave this for him to do but I have one pressing concern as we are currently trying to conceive and as far as he has vocalized this is very much something we both want and so I am concerned that if he doesn’t tuck correctly when wearing Gender Affirming Underwear that he may create problems with testicular distortion or cause and ED problem.

Do you have any advice on this please? I love my husband and I want to go about this in the right way. I don’t want him to not explore this if its something he wants to do, and I worry if I handle it badly that this is what will happen. I have read one of your very super long articles but if you can point me in the direction of more or have any words of advice. This would be greatly appreciated! Thankyou xx

I know a lot about tucking but I am afraid I don’t feel I am much of an expert on how tucking (or anything else) could impact someone’s ability to obtain and maintain an erection. Um, for what it’s worth, a decade of tucking hasn’t affected me. I am not… ah, not trying to brag but what I mean is that tucking can be done (at least so far) without causing damage or being painful.

What I can say is that if tucking hurts, then you’re doing it wrong. Try a different garment, try a different technique, untuck and try again.

Could it cause damage to the point where reproduction is difficult? I don’t know. This would be a question for your doctor.

And you can be subtle when you ask them. Ask your doctor if keeping one’s testicles close to their body could cause damage (body heat, for example). You don’t necessarily need to tell your doctor your partner is tucking but you could ask if wearing certain undergarments (whether it is a tucking panty or boxers, etc.) really matter.

But if you don’t mind I’d like to comment a little about the elephant in the room, er, the elephant in your question. In your words, he is lying to you.

When it comes to a relationship and crossdressing, it’s usually not the crossdressing itself that is a problem. It’s typically the things that come WITH crossdressing. Dishonesty, going behind their partner’s back, stepping outside of agreed upon boundaries, spending more money on clothes than they told you, etc.

It doesn’t sound like you are bothered by the idea of him crossdressing and that you are trying to open the conversation with him about this to show your support. I realize that this may be a difficult to thing to be supportive about but I hope you are being honest with yourself as this is a lot to take in.

In most cases, the lying tend to snowball. A little lie now grows into a bigger lie later on.

If you want my advice, here it is:

Be direct, be gentle. Tell him what you just wrote here. “I saw that you ordered a dress and I want you to know I am supportive and I would really talk about this side of you when you’re ready.”

He may resist, he may blow you off, but hopefully he will be open. If not, well, perhaps counseling is the next direction. He may benefit from talking to someone so he can sort out his feelings. He is in the process of discovering himself. Gender identity is an overwhelming thing. I also wouldn’t rule out counseling for you and/or the pair of you, either. Counseling isn’t always beneficial when there is a problem in a relationship, counseling is beneficial when it comes to developing stronger and more honest communication.

Listen.

A committed relationship takes work. You know this. Your partner’s crossdressing is not something that will “go away”. Please don’t count on him coming around and broaching the subject with you if you’ve already opened the door to it. A new baby will forever change your relationship and your life and leaving something major unaddressed (such as one’s dishonesty about their gender identity) will likely cause bigger conversations down the road. A partner’s crossdresser almost always complicates a relationship.

Love, Hannah

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4 thoughts on “Ask Hannah!

  1. It has always been my experience that the person will open up when the time is right. Hannah is right that you need to address it, but you want to be very careful not to create a situation where you make them feel uncomfortable or forced. That never ends well. My wife buys me lingerie for various occasions (Father’s Day, Xmas, etc) because I am a practical man who gets what he needs and Dora’s put much stock in gifts. Probably a male thing. As Camille, I look forward to the pretty gifts and she loves being able to give me something that I’ll actually use/enjoy. As such, you may consider a random gift if you can figure out what size they wear. It says “I am trying to accept this about you” and it may open up the dialogue in a more natural way. Trust me, it’s hard for a cross dresser to pass up a nice bra and pant set or a teddy, etc.

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  2. I 100% agree with Hannah as I have gone down this path and it doesn’t work. Just remember he maybe feeling a little guilty about all of this as it is VERY hard to understand. Talking to him will be the only way to relieve his way of thinking that this is wrong! Rough yes it will be rough trip but the outcome will be a wonderful trip for both of you to enjoy. Remember the only person that can make YOU feel guilty is you! After 68 years I can fully understand! LOL

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  3. I remember back in the day they said men should wear loose fitting boxers for better reproductive health rather than tight fitting Jockey style briefs.

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  4. It is going to be hard but please, please if you value your marriage and your story together, be straightforward and comunícate directly to him what you are feeling about everything regarding and around his crossdressing…hinting does not work! And most of the times, if not all, it is going to be you, (wife) who brings up this conversation; almost never expect him to bring it up.
    As Hannah says, crossdressing by itself is not usually the issue, although it takes a lot of compromise and commitment from BOTH, the crossdresser and the wife, to really make things work.
    However if there is lying and it is not “cleared out” or dealt with, it will most probably start escalating to a point where there is no going back or it is very difficult to do so… the reason behind it does not matter; either because he is not ready to share that part of him, because of what you might think or simply because he does not want to tell you the truth because it is more convinient for him to have “both worlds” separate… whatever the reason, lying does destroy, or at least greatly damage wonderful marriages.

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