Coming out to a significant other can be a massive step in a crossdressers journey. There is the rush of telling someone your secret but at the same time the fear of rejection – especially from a loved one.

Like so many of us when we are just starting out, for several years I had dressed privately. I had created Jessica, a part of me the world at large never got to see. Deep down I knew I wanted to share this with someone – I wanted to share it with everyone if it came to that, but baby steps.

One night a month or two ago, my fiancee (who I have been with for six years), were discussing our fantasies. She asked me if there was anything I had ever really wanted to do in a perfect world with no judgment.

There was never going to be a better moment than that, so I came out and said it.

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I explained that for several years I had enjoyed wearing women’s panties in private while she was out and that on occasion I had borrowed one of her dresses out of her wardrobe. (Side note: Don’t do that, she never complained, but honestly the more I think about it the weirder and more invasive it is – buy your own stuff, or ask permission to share, but don’t steal other peoples clothes). 

I told her that it was a part of who I was inside and that I wasn’t transgender – I am a man, but I enjoy the act of dressing, of putting on makeup, and becoming Jessica for a period of time.

She sat intently and listened, and when I had finished my explanation, I made clear that I totally understood if she didn’t understand, and that if she wanted me to stop I would stop for her. 

I decided that putting the ball in her court would allow her to process the confession, and would also allow me to see how she reacted initially.

She just laughed, and went to the wardrobe, pulled out one of her old dresses which no longer fit and through it in my direction.

“Put it on,” she said, “I want to see you dressed up!”

My mouth curled into a beaming smile. I was so surprised by the complete and immediate acceptance. We talked a lot that night, and in the days and weeks since, about my dressing, and her general attitude has been, “Well if I can wear a guys t-shirt or hoodie or jeans and not get judged, why should it matter if you wear a dress or makeup?”

It was like the dream scenario. I couldn’t have plotted a better outcome in my head if I had tried, and the fear I had had about telling her has changed into an anticipation and a hunger to try more.

My partner has since taken me out shopping, and brought me a nice dress of my own – a bargain in a local thrift store – as well as some panties of my own.

The confidence I’ve gained from telling her has even led me to be able to wear these panties under my male clothes in place of my usual boxers while I’m out and about. It is hidden yes, but this has been a huge step for me.

What I’m saying above all is, I understand that you might be afraid or apprehensive to tell your significant other about your dressing. I know my dream scenario isn’t going to be everyone’s result either – I’m not naive – but just know, the success stories are out there. You don’t have to hide. Step out, Girls. Step out and be yourselves – who knows you might even gain yourself a new shopping partner with a great sense of feminine style.


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    26 years old, Jessica has recently become more open about her dressing, and is ready to explore her journey

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    5 years ago

    Just a great story Jessica. My wife of many years wouldn’t be to keen on me going out and about overtly, but one time about ten years ago she decided to switch brands of panties and I asked her for her cast offs. She was surprised at first, wasn’t too happy but decided on her own that I had a fetish to answer to and put this big pile on the bed and said, “…have at them.” We haven’t looked back and I have worn panties ever since, added bras and camisoles. I wear woman’s jeans too. I love the… Read more »

    Alice b Carpenter
    5 years ago

    At first she seemed to encourage me, then she started to to get distant eventually she asked me to leave. Then we lived apart which seemed to work we could still meet etc. Although we’ve come to a natural conclusion in our relationship, she still remains my rock as we’ve always said sometimes love isn’t enough. She remains my best friend wardrobe adviser and shopping buddy and as we’re a similar size, clothes horse at times.
    Hugs Alice

    Jennifer Schmidt
    Jennifer Schmidt
    5 years ago

    Great story Jessica I wish my wife was on board with me but she and my daughter thinks it is gross

    5 years ago

    That is so awesome I hint around with my wife but when she gives me this I’m weird look I stop. My thing is pantyhose and thigh highs. I always have on a pair under my pants My wife knows but I play it off as I use them for warmth. Great story.

    Lady Veronica Graunwolf
    Lady Veronica Graunwolf
    5 years ago

    Jessica , I am happy for your and your wife…….now there is a partnership!

    linda smith
    linda smith
    5 years ago

    As a wife of a cross dresser my husband is a loving husband and I under stand his situation. I support him as best I can. I see no harm in it at all. I try find things to suit and do my best. Over all we are together 30 years now and I feel the same today as the day I meet him.

    Dee Writer
    Dee Writer
    5 years ago

    I dunno. In the past six months I have come out to my wife as a submissive and she is now the head of our household. I have also told her a lot about my weird and unconventional fantasies, my desire to be dominated and my joy when she publicly asserts herself over me. She has come a long way with me, patiently and kindly. The crossdressing might be a bridge too far.

    Julliett Marie
    5 years ago

    I wish my so would be supportive and we could have a lot of fun with it

    Peggy Ann Culpepper' class='avatar avatar-64 photo' height='64' width='64' />
    Peggy Ann Culpepper
    5 years ago

    You have a soul mate to die for and don’t realize how blessed you are.
    There are about 99% of us girls out here crying tears of joy for You and
    tears of sorrow for us. Most of us are happy to even have a closet to hide in.
    Thanks for sharing your story, these morsels of good news are what we come
    to CDH for. Thanks again-GOD BLESS YOU and that FANTASTIC SOME OTHER.

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