I write this in the midst of trying to sort out several thoughts and emotions. I’m elated to share my news, and yet a little hesitant because I sympathize with so many of you. This isn’t me bragging; I want to share my experience as I am sure that I’m not the only one who’s had a similar experience. I want to provide others the encouragement they might need to talk to their SO’s about their crossdressing.

Like many of you reading this, I started crossdressing at a very young age. I don’t know the exact age, but do know it was pre-puberty. I’m not sure as to exactly why I started, but my best guess is that I found female clothes to be very pretty and wanted to emulate all of the other beautiful girls out there. This went off and on while I grew up until I moved out of my parent’s house. Once I moved out, I did not have any items of my own to wear. When I was dating, I would occasionally sneak around and put on a pair of my girlfriend’s panties, but that was about it in regards to my dressing.

Then I met my wife. The fact that I like to wear women’s clothing never came up while we were dating. It was something I struggled to deal with personally, and I didn’t know how to handle it. I grew up in a small town surrounded by some extremely judgmental people; I wasn’t sure how it would be perceived. However, one night after going out and having a few drinks, I brought her back to my place. I don’t remember exactly how it unfolded, but I remember picking up her dress and her telling me to put it on. That night was some of the best “fun” we’ve had.

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I also mentioned to her that I was curious about trying on a bra. Over the course of the following months, I began wearing her panties when in bed together. One day in my dresser, I found that she had put a bra there for me. This later led to both of us wearing lingerie. Even though I was super excited about how this had progressed, and even after purchasing some of my own items, we still hadn’t really discussed the topic thoroughly.

These activities continued after we got married. However, one night while we were at home having some drinks, I’d gotten dressed in a bra, panties, thigh highs and a dress that I had purchased. After having some drinks, I brought up the topic of my desire to wear women’s clothing and shared with her some of my history. This changed things severely in our relationship.

In short, my wife said she was “okay” with it, but asked that I take things slow; to ease her into it as she wasn’t 100% certain she could be on board. In the years following, I received a crazy amount of mixed signals from her. There were times that she would purchase me panties, and times where she seemed unfazed by my dressing while in bed, and times where she seemed very cold and repulsed by the idea. I even went through the phase of telling her that I would stop and never do it again. If you read about crossdressers, you know that this isn’t possible.

Needless to say, my urge to wear feminine clothing never left. I began wearing again, but this time much more secretly, after she went to sleep. I was always nervous about her coming downstairs and catching me. I wasn’t sure how either of us would react. I wanted to talk to her about my crossdressing, but feared that it would lead to divorce and end my marriage to the best person I have ever met. This caused a lot of anxiety, which lead to depression, anger, and other issues.

I knew I was dealing with these things, but I didn’t realize how directly tied to my crossdressing they were. It came to a point where I called a counselor as a last ditch effort, knowing my marriage was failing as a result of all the side-effects. I finally had enough; I was extremely depressed about things and asked my wife if we could talk.

We went for a nice long walk as we like to do when we need to hash things out. We discussed everything, except crossdressing, and I felt much better when we got home. However, I still felt as if I had unfinished business. As we stood in the kitchen, I told her that I needed to talk to her about something else that evening. I didn’t want to talk extensively about it then, due to other people being in the house. With the few short words I gave her, she knew exactly what I wanted to talk about. She immediately gave me some very kind words, reassuring me that she loved me for who I was and was going to support me. What she said brought tears to my eyes. I felt like the weight was starting to lift off of my shoulders.

That night, we talked for about three hours. There were several things I needed to say, to explain, and to ask about. My wife also had her share of things to say and ask. I couldn’t be happier with the result of our conversation. My wife told me that she wants me to be able to feel 100% comfortable with myself and fully supports me wearing feminine clothing. I no longer have to be secretive about it. She is totally acceptable to walking around the corner and seeing me in a dress and heels.

My wife did request that I take things slow, allowing her to get used to some aspects of my crossdressing. We agreed that if she wants to take a step back, she will say something, and I won’t dress at that time. However, she said becoming more passable or even going out together is a possibility down the road. She also agreed to help me find my correct sizes and to shop with me both online and in stores. She currently sells some of her clothes online that she no longer wears. She gave me the okay to go through them and pick out items that I like and want to keep for myself.

I’m still on cloud nine and couldn’t be happier. I can’t believe how much lighter and less burdened I feel. It’s made me realize how much of that anxiety, depression, anger and other issues were directly related to my crossdressing. Now that I’ve had that conversation with my wife, I’m able to be more open about my dressing, and we can talk about it anytime. I can ask her a style question or inquire about something she does while getting ready.

All of those negative side-effects have subsided and are mostly gone. I can’t tell you how many blogs, forums, and posts I read from people who stated that in order for crossdressing to work in a relationship, you must have open communication with your SO. I withheld mine far longer than I should have as I was nervous to bring it up. Now, I wish that I would have brought it up sooner.

I hope this can be another positive story encouraging others to open up and have that communication with their SO.


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  1. Rochelle Mills 3 months ago

    Wonderful, heartfelt description! All the best for you and your wife.

  2. Zoe Peru 2 months ago

    Thanks for sharing your story. Coming out to your wife or SO can Be difficult and risky. I’m sure it wasn’t easy for you, but you’ve done it!! I’m so very happy for you and your wife. I suspect your wife will soon (if not already) enjoy the wellness CD’ing brings to you and her. Have fun. Z

  3. Miss P 2 months ago

    Jessica, Thanks for sharing this part of your story. I am glad that you had your “amazing conversation” and that life going forward is much more hopeful. In your story, you mention going to see a counselor. I fully endorse do this. In my own experience, going to a counselor who is both understanding and supportive has been incredible. She has given me a sense that I have worth and that the shame which has been present to lesser and greater degrees over the years has begun to go away. I have felt much more empowered and I am glad to say that my wife and I have had some very good conversations as well. Thank you for sharing.

  4. Charlotte Bristol 2 months ago

    That really good for you both Jessica, much healthier than keeping secrets. I am also blessed with an understanding wife. She’s happy for me to be dressed at home, just not too keen on me in a wig around the house. We’ve both started going to a local support group where I can be fully dressed and she can chat to other SOs (not that we particularly needed support, just a nice social thing).
    We are so much closer as well now and have more in common and more to chat about than before. We go clothes and jewellery shopping together. It has greatly improved our relationship. I am also much calmer as I am being truer to myself and not hiding a big part of me.
    Obviously you need to tread very carefully with this, but the benefits to both in a relationship can be very great.

    • Author
      Jessica 2 months ago

      I’m glad to hear that you too have such a supportive wife! I can relate to everything in your second paragraph. It is a process, but our relationship between my wife and I has grown tremendously. I also feel much calmer as I am able to be my true self. It just feels right to be able to comfortably dress how I want around the house. I am working on getting ready to go out for the first time, but not sure how soon that will happen yet. Going to counseling and talking openly with my wife about it has helped immensely to overcome feelings of shame allowing me to become more comfortable with this. That has allowed me to become more calm and more aware of the needs of those around me as well. Overall, it is freeing up brain space for me to be able to focus on other things no matter how small they may seem.

  5. Angie 2 months ago

    Well done for the bravery, I feel that now you are both over that hurdle, your relationship will go from strength to strength and you personally, will be in a much better place with your mental health. Wishing you both all the very best for the future.

  6. Michelle 1 month ago

    Thank you! Talking about cross dressing with your SO is nerve racking. My wife knows I am a cross dresser. and that is about as far as it goes. She has passed down some of her things to me which is a good sign. She has read alot about cross dressing. We really don’t talk about it. There is still an invisible barrier that I cant seem to get over. She has know about my cross dressing for a year or so. My hope is that we can get to the point that we can share this.

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