Nearly every crossdresser I’ve had the privilege to meet since I joined Crossdresser Heaven has expressed at least some level of insecurity about their femme side. Why do I need to dress? Am I weird? Will I find someone who can love and accept me? It’s unfortunate that our society has forced so many beautiful women into the closet because we can’t accept something new or different. It’s completely understandable though why crossdressing can cause major insecurities. As I’ve been getting to know more genetic girls in a relationship with a crossdresser, I’ve found that we have a unique set of insecurities ourselves, aside from the typical insecurities many women in a relationship feel.

The perception of femininity that a crossdresser has if often much different than that of genetic females. We’ve grown up entirely female, so the allure of all things feminine is sometimes lost on us. Sure, most of us like to get dolled up and feel pretty, but it isn’t something that permeates our thoughts and daily lives as it does with many crossdressers. Our partners put a lot of time and effort into presenting themselves beautifully, and some of us partners wonder if we’re girly enough. Do our partners mind that we don’t always embrace our femininity? It sounds backwards, doesn’t it? But the idea that the genetic female in the relationship is insecure about not being feminine enough for our femme loving partners is a frequent topic of discussion among us partners.

There are other insecurities too, that are harder to share with our partners, because they stem from us not understanding crossdressing, as hard as we may try. We don’t know how our relationship will change when we find out about our partner’s femme side, and it can be scary. They may do everything right and make sure we know they love us but it’s hard not to worry that their feelings for us will change because our relationship dynamic has changed so suddenly and drastically. It’s not a fair thought to have, but it’s one that almost all of the partners I’ve talked to have had. Perhaps it’s the feeling that we’ve invited another person to join our relationship. We haven’t, of course, that femme persona was always there, we just didn’t know about it, but we don’t have any other frame of reference for no longer being the only woman in our relationship.

While discussing this in the Significant Other forum, another SO said something that has allowed me to reframe how I think about this particular insecurity. She’s given me permission to share her thoughts. When responding to a member who was questioning whether their partner will still love them and want to be with them, she said He dressed before you knew and you are the one he desires.  He dressed when you knew and you continue to be the one he desires.  Dressing makes him who he is and you make him feel loved so does dressing really change that love and commitment you have with each other?” I felt like a lightbulb in my head (or perhaps my heart) went off! My partner knew about his femme side when he fell in love with me, so why would his feelings for me change just because I know about her now? If anything, wouldn’t him being able to share this special part of himself just make his love for me grow?

One of the things I love about this community is the way we can share with and challenge each other. My challenge to you, whether you are a crossdresser or you love one, is to keep in mind that for all the insecurities you have, your partner probably does too. These may never go away, but if we don’t talk to each other about these kinds of things, we may miss a perspective that can help us feel just a bit more secure in ourselves or our relationship, and that can bring great comfort.




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*Trisha Anne

I'm a genetic female, in a wonderful relationship with a super manly guy, who just happens to wear pretty things in private. I'm here to learn how to be an even better partner to him as I navigate these new waters.

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Chrissy Hilar
Chrissy Hilar
1 year ago

That’s so beautiful. I told my wife everything before we got married, and she accepts me more than I do. I feel that the truth will set you free as has me. It took a lot of guts to tell her but I wanted to marry her and I thought she should know before we get married. Now we share face masks and do each other’s nails and hair. I am living a dream

Sheryl Gibson
Sheryl Gibson
1 year ago
Reply to  Chrissy Hilar

I so appreciate what you said here. I just joined today. I met my boyfriend online two months ago and he was up front about everything before we met. I’m so glad he was honest with me because he is the most amazing man I have ever known. I tell him he is beautiful all the time, but I am the first woman he ever told and he is very insecure. I want to do all I can to support him. You give me hope. Do you have any advice or words of wisdom for me?

Joan Michaels
Trusted Member
11 months ago

*Trisha Anne, as a man with a significant feminine side thanks for looking as to what makes men who crossdress dress to express their feminine side. I was just recently reminded of something I said in High School 49 years ago, “I would wear a skirt all the time if I could.” The greatest thing is men fear the stern rebuke of other men via the MASCULINE Gestapo and society in general. So men end up crossdressing as women or transition to become a woman. Likely because they cannot wear skirt in public as a man and can as a… Read more »

Kristen Smithly
Active Member
7 months ago

I keep my crossdressing low key, mostly underdressing, but my wife knows I do crossdress. I keep it low key because I had a 23 year marriage end and my crossdressing was one of the main reasons for it, so I can understand the insecurities issues with dealing with it. I love my wife dearly and I respect just as much. I can’t ever know exactly what she feels about it because I am not the one married to a crossdresser. I try my best to be attuned to her concerns. She knows she can trust me, that I am… Read more »

Jamiee Oberg
5 months ago

I’m in the same boat with you . Good luck on your journey

Jamiee Oberg
5 months ago

Thank you so much for sharing. I’m new here but have been crossdressing for years now very hidden from everyone. Just recently I came out and told my wife everything even from the time I felt different from everyone. At first it was scary then it when to being very excited. Then my wife of 21 years told me she was kind of into men wearing panties or “ shemales “ and that she would read stories about it . I was like this is awesome and I had wished I told here a long time ago. Then I started… Read more »

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Inga Krasivaya
3 months ago

Wish I’d read this many months ago… The point about a lady perhaps questioning whether she feels feminine enough for her… errrmmm… lady, is something I had never thought about. My own SO is not exactly someone who could (or would!) describe herself as “the most girlie girl” but I’d never thought that she could doubt her femininity. No, she doesn’t know about me crossdressing (at least, I think that’s the case, though I have plenty of reasons to believe she does) but to think she could doubt her femininity? I never thought that possible – but now I have… Read more »

Sarah Jones
3 months ago

About 9 months ago I told my wife I would stop crossdressing, but today I had to tell her my desires are still there and I am still interested in feminine clothes and make up. I don’t think she was surprised by my admission I rather think she was more aware of this than I thought. For me it was hard but the honesty is so liberating and gave me a good feeling. Saz

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