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.

EnFemme Style

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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    Terrisa Washbourne
    4 years ago

    Jessica, that was well written. The truth will set you free and it has a an awesome way! You would be surprised at how many people enter a marriage lying and you have not but I could imagine it still took guts to say it. Hugs – Terrisa

    skippy1965 Cynthia
    Trusted Member
    4 years ago

    Great article and well said about not stealing/borrowing someone’s clothes behind their back-as you note it’s an invasion of their privacy. My ex was NOT at all tolerant or accepting, so my congratulations on your good fortune. 🙂

    Scarlett Slater
    4 years ago

    Jessica your story is very similar to my own, it takes courage to cross that first step and to be honest you’ll never look back. There is a good chance this is just the start of your journey and I wish you all the world in discovering the real you.


    Scarlett xx

    4 years ago

    Thank you Jessica for your thoughts hun hope you and your enjoy your journey hun
    huggs Katie

    Laura Days
    Laura Days
    4 years ago

    Congratulations on your success when sharing it with your fiance, but even more, I congratulate your courage to grasp that opportunity to share it with her, it must not have been an easy step to make.

    Holly G
    4 years ago

    Jessica I wish all of us had that same result. I waited over 15 years before my wife found out about Holly. This was definitely not the best approach. I hid Holly to protect my wife but in the end I only shielded her from the truth which she regretted in the end. I wish that I had the chance to come clean like you did with the person I love back at the start. We are slowly working our way through it though so I still have hope!

    Managing Ambassador
    Active Member
    4 years ago

    I love seeing the success stories! Thank you for sharing! I told my last girlfriend. Only person I’ve ever came out to fully. We had been seeing each other about 3 months, I’ve adopted a philosophy of letting my secrets out early so she could leave before we’re in too deep if she’s not cool with what I share. I warned her that one day she’d see girl mode in action. A couple months later it happened. She talked like she was supportive but I didn’t get the vibe she was really feeling it. Weeks later she talked a little… Read more »

    Alice b Carpenter
    4 years ago
    Reply to  Sa·man·tha

    I tell ladies early too now. Some say bye but remain friendly some hit the highway some say ooookkayyy but then they know I’m not going to drop a bombshell on them

    donna walter
    4 years ago

    I’m one of the lucky ones my wife is all for it. we go out and she will pick out something and say this will look good on you.

    Jamie' class='avatar avatar-64 photo' height='64' width='64' />
    4 years ago

    My first two wives hated the idea and never supported it in any manner. I divorced the first one, God took the second one. My current wife is very supportive. We talked about it prior to marriage. Her only restriction is not during sex. We share clothes and even have matching outfits. Lovely story, glad it worked out for you .

    Roan B
    Roan B
    4 years ago

    You’re very fortunate, Jessica. I’m very happy your coming out had a positive outcome. She is definitely a keeper. Congratulations.

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