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.

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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Jessica

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

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30 Comments
  1. Stephanie-Kimberlie 4 weeks ago

    Very nice !

  2. Leonara 4 weeks ago

    What an inspiration for all of us…thank you
    For sharing

  3. Sara Marie Franklin 4 weeks ago

    Jessica you are so very lucky. I wish my wife took to the news as well as yours did. It is good to see people being more open to our situations.

  4. Gina Hall 4 weeks ago

    Jessica, you have so much courage. You are very beautiful by the way.

  5. Patsy Jennusaith 4 weeks ago

    A world with no judgement would be paradise.

  6. Marianne 4 weeks ago

    Jessica, you are a very lucky girl. My wife just barely accepts my dressing as Marianne as long as I do it out of her sight, but is mot in any way supporting.

  7. nicola 4 weeks ago

    When I told my wife she was very supportive and said as long as I didn’t dress in front of the kids she didn’t mind. Now they’ve left I can dress when ever I want and now we go shopping together and gives me advice what clothes would suit me.

  8. Ashleigh 4 weeks ago

    Great story! Thanks for sharing. You are fortunate to have a supporting partner. Enjoy the journey, and as you said “ baby steps”.

  9. Rhonda Roe 4 weeks ago

    Jessica
    Thank you for sharing your story. I Love happy endings. I wish more SO`s where as open minded as yours. Best wishes to you going forward.

    *hugs*
    Rhonda

  10. Lana Dazzler 4 weeks ago

    Jessica first hun i want to say good for you that you came clean with your significant other. I wish i had done the same thing with my SO but i didnt and when she found my stash of lingerie and a wig she about blew her top. I tried to explain why I dress but she didn’t want to hear what i had to say and doesn’t ever want to see me dressed. Once again congrats and hun keep on loving yourself and enjoy wearing those sexy panties that you have. Xoxoxo

    • PaulaPlaytex 1 week ago

      LANA…THERE IS NOTHONG BETTER THAN WEARING MY BRA !!!

  11. Terrisa Washbourne 4 weeks 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

  12. skippy1965(Cynthia) 4 weeks 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. 🙂
    Cyn

  13. Scarlett Slater 4 weeks 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.

    Hugs

    Scarlett xx

  14. kate dancer 4 weeks ago

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

  15. Laura days 3 weeks 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.

  16. Holly G 3 weeks 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!

  17. Samantha Sang 3 weeks 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 smack to me about what I shared and eventually told me that she felt like she had to “compete” with me…I guess I had made her feel that I was more feminine than her…that makes me giggle but more so I feel bad that she saw it that way. I too had been hoping for a shopping partner or a girls night out. We’re not together anymore, NOT because of that, but other things, we weren’t in the same place anymore after 3½ years. It’s fine. Live and learn eh?

    • Alice b Carpenter 3 weeks ago

      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

  18. donna walter 3 weeks 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.

  19. Jamie 3 weeks 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 .

  20. Roan B 3 weeks ago

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

  21. Robbi Stevens 3 weeks 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 feelings I get when in my girlie things….sometimes I get very emotional, tears of joy really but when I’m feeling that way, I can feel the sensitivity of my skin and every movement reminds me of how much the blend of gender makes me whole.
    xox

    • PaulaPlaytex 2 weeks ago

      Not married, However my Sister-in-Law gave me my “FIRST BRA”…She with the size of my BREASTS (46B/C) that I “NEEDED TO WEAR A BRA” !!! I received a Nightgown, Panties and Pantyhose from her last Christmas…HOW GREAT IS THAT !!!

  22. Alice b Carpenter 3 weeks 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

  23. Jennifer Schmidt 3 weeks ago

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

  24. PaulaPlaytex 3 weeks ago

    I don’t have a partner (Male or Female). My Sister-in-Law gave me my first BRA. She said I need to wear one. I wear a 46B/C/D BRA now depending on “My Mood” She said not to hide my Bra wearing…Just be “Myself”. I wear my Bra 24/7 365, also Panties, I sleep in my Nightgown that she gave me last Christmas. She also gave me some Pantyhose…How sweet was that !!!

  25. Dan 3 weeks 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.

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

  27. linda smith 2 weeks 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.

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