The Insecurities of Loving a Crossdresser

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.

Latest posts by *Trisha Anne (see all)


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  1. Sarah Anne 9 months ago

    Very nice article Trisha. I have found it very difficult to find a female to be in a relationship with that is not only understanding of my CD lifestyle but supportive. I have tried the various dating sites and have had contact with GG’s but once they find out I am a lifestyle CD they run for the hills. Some are intrigued but most are just not understanding enough to pursue a relationship with me. That being said I will probably stay single as I have taken myself off the market. If there is one thing I stand by is that I will never compromise myself to conform to what others think or want.

  2. Liv 9 months ago

    Thank you so much Trisha for sharing. I have read it over and over and will share it with my wife.
    hugs, Liv

  3. Katie 9 months ago

    Hi Trisha I’m a genetic male but I think I should have and feel I am a woman.Im married with kids and all my life I felt different.Ive worn women’s clothes from I was about 8 not to play dress up but it felt normal as I thought I wd become a woman one day!Weird I know but it is how I felt all my life.I told my wife a few years ago I like to crossdress after we had a few beers and she seemed fine with it and took me shopping and bought me bras and panties and I thought I was in heaven thinking it was the start of my new life as “Katie” but after a while she started hiding my bras and panties so I took it she doesn’t approve which I totally respect but if your man likes to wear women’s clothes consider he might be doing it for different reasons most men that crossdress are straight.I think I should have been born a woman that’s why I need to do it but your man might just like the feel of dressing as a woman so don’t be too hard on him take him shopping for girly clothes and you will make her the happiest girl in the world and that in turn will if you let it bring you closer together.Good luck

  4. Stephanie Flowers 8 months ago

    Trisha I can’t stop reading this , Beautifully written. It shows insecurities can be deeply scarring in life’s challenges . My wife continues mentioning thoughts about my love for her, her feelings towards her identity, and our relationship in a whole. This community shows compassion and you Trisha thank you for bringing this to light.

  5. Rose Turner 8 months ago

    Trisha. Yes, we are weird. But we are loving every minute of it.

  6. *skippy1965(Cynthia) 8 months ago

    Another awesome article! You do a great job letting the community know how our SOs fears and worries manifest yet can still hope to work out a path for relationships to continue. Thank you so much for sharing our perspective and helping bridge the sometimes daunting gap we face in understanding each other! I can’t wait to see your next article! You ad your SO are two very very lucky people


  7. Paula1 8 months ago

    Thankyou for this Trisha, Your prospective form a SO side is so true, my wife and I have spoken about this so many times, as she is not as into displaying her fem side as much as I do, and have two girls 16 and 12 years old and trying to understand there needs to wear makeup and go shopping is hard for her, but it one off the things that I love the most, I have always dressed from as long as I can remember and my wife found out about 8 years ago, the times have been a rollercoaster ride for both of us with the insecurity’s from both sides, will she leave me, am I a freak, and also from her side will I keep changing, dose he still love me, All I can say is communication has been the key to us staying together, The love that we have for each other is I believe stronger than ever before, I will ask my wife to read your article so she knows that she is not alone XXX

    • Patricia Marie Allen 8 months ago

      It took 10 years for our roller coaster ride to calm down. The best thing you can do is to become “Super Husband.” Pay attention when in casual conversation with her. If she mentions something she likes or states a preference about something, make a mental note. After a time, long enough that it doesn’t look like you’ve taken it as an order and you are submitting to her, make it happen. It needs the be and look like an act of love.

      For an example, I discover, years ago, that my wife’s personal preference for milk shake flavors is peanut butter. Peanut butter milk shakes aren’t common in our part of the world. Dairy Queen is currently the only place that has them. When I’m out and about, I might just stop by pick one up. and bring it home for her. I do this sporadically and tell her, “I was thinking of you, so I got this for you.”

      Another example is that another family member sent us some digital pictures of our grandchildren. As we viewed them on the computer, she commented that she like to have and 8 X 10 of one of them. That Christmas, I got a friend who is a photographer and makes print of digital photos all time to make me a print. He also framed and matted it for me. He wouldn’t accept any money for it. I boxed and wrapped and include it in the gifts I got her. All told, that Christmas I spent $200 on her. When she opened, she said with surprise, “You do listen to me.” And when she recounted her Christmas to others, she didn’t say anything about the other gifts, she only told them about the picture that cost me nothing.

      It’s the little things that count.

  8. Giselle Reeves 8 months ago

    great post Trisha
    posts like yours saved my marriage when my wife connected with other wives and girlfriends on this forum.
    our marriage is not like it once was(i lost the complete trust of my wife and also how she views me as a man and husband) ,but we are still together more best friends and looking to grow old together.

  9. Jezebel Jetlag 8 months ago

    Thank you Trisha, so much. It’s as if I joined this community just so I could read this article, which has already helped calm me down so much. It’s days since the man I Love with all my heart told me he liked to dress in lingerie and other sensuous feeling women’s clothing. The questions in my mind seemed endless and overwhelming, and not in any way helpful for starting important conversations. So your article has helped me more than you could imagine

    • Author
      *Trisha Anne 8 months ago

      I’m glad I could help! Have you read one of my other recent article titled “To the Partner of a Newly Outed Crossdresser?” You may find some insight there as well. Welcome to CDH!

  10. Erica Sparkles 8 months ago

    Great Article Trisha

  11. Melissa 8 months ago

    This is good article. When I was reading the article and probably most of us happen, We are identifying with that person, have a wife that can you trust in your femele side is hard to find, my wife knows what I want and what I like but always inside the bedroom, we have kids and is very dificult let them know what I am or why ai am doing this to dress like their mom because my dougher wants me like her masculine pathet, strong. This is very frustrating only be in the closet but the good thing is your wife support you. Well sometimes she is not 100% agreed what I am and many times we are discussing about my femele feelings. I congrats Trisha for thing positive like that and gave 100% support to her husband. Maybe one day we can meet and can know my wife because I understand is very difficult for a wife to know husband like to use her dresses.

  12. Deety 8 months ago

    Nice article Trisha. I always loved the water babies as Iwanted to grow up in a world run by Mrs Doasyouwouldbedonby.
    We should all always remember the other persons point of view befor we express our own

  13. Elise Michelle 8 months ago

    Thanks, Trisha. I wish I had a wife who was as understanding as you. I’ve been married twice, and neither one worked out. My first wife didn’t find out until after we divorced, but the second found a stash of photos and clothes. She flipped out (I can’t blame her) and refused to ever talk about it again (I do blame her for that).

    I’m certain she must have felt the same insecurities you so eloquently expressed, I just wish she would have felt comfortable enough to discuss them with me.

    Thanks for sharing. I wish you both a lifetime of happiness and understanding.

    Hugs, Elise

    • Scarlett398 8 months ago

      Elise, I know exactly where you are coming from. So far and I don’t ever think my cross dressing will ever lead to a divorce or even a separation.
      When my wife found out the first and second time I was a cross dresser and couldn’t give it up, she freaked out!
      Now she knows I will never give it up and the fact that I’m really good at it as well.
      Elise, she has now reached a level of acceptance of which I thought she would never ever reached. The fact that I can store all of Scarlett’s things in our new home and that I can dress whenever I want as long as she’s not home to witness me getting my girl on.
      I’m not sure if she’ll ever go further with her acceptance of my cross dressing and the limits she’s put on my cross dressing, but if she doesn’t, I’m just fine with were she’s at with the limited acceptance of my cross dressing.
      I’m sorry your two first wives never could get to any level of acceptance of your cross dress but I can definitely relate to your past situation because it’s where I thought I would end up with my sexy redhead!
      Take care Girl Friend and look forward to hearing again from you soon! XOXO Scarlett

      • Elise Michelle 8 months ago

        Thanks, Scarlett.

        You are indeed lucky to have an understanding wife. I honestly think that understanding and acceptance is all we can ask of our SO. While we all dream of the SO who will embrace and partake in our activities, I don’t think that’s realistic. Unless your SO has bisexual tendencies, she’s not likely to want to visualize her man as a woman. I know I wouldn’t have been thrilled if my wife wanted to look like a man. Of course I would still love her and would like to think I’d be accepting, but I don’t think I’d want to help apply the facial hair and “strap on” accoutrements.

        Oh, and I absolutely love that you refer to your wife as the “sexy redhead.” I hope she sees how much you obviously adore her.

        Hugs, Elise

      • Author
        *Trisha Anne 4 weeks ago

        Finally catching up and responding to comments… I think it’s important that you recognize that wife #2 had the right to be upset when she first discovered your secret, but also that it was not OK that she refused to talk about it further. Relationships are a challenge, and half the challenge is communicating when things get difficult.

        I would like to add, if for no other reason, than to perhaps speak to partners who may read this… I’ve never considered myself to have Bi tendencies. I would have never pursued a relationship with a woman. It simply doesn’t interest me in the slightest. However… I love my partner. I love him enough to love her. If I have a wife, instead of a husband, something I certainly never planned for, I will still have my person. I know we might face some challenges, but just as her sexual orientation isn’t tied to her gender identity, my love for her isn’t tied to her gender identity either.

      • Scarlett398 8 months ago

        Hi Elise, thanks for you entertaining note and you’re right about total acceptance unless there may be some sort of bi tendencies. Not always the case but probably has a bit to do with complete total acceptance!
        I do have a fantasy that I will never be able to live out. And that’s getting all dolled up as Scarlett and go to bed with my sexy redhead with her all dolled up and us light a few Yankee candles and just spend the next two hours making love to each other while working around all of the sexy clothes. Won’t ever happen and I realize it will have to remain just that – A total fantasy!
        Or even go out on a dinner and movie date with her dressed up at girl friends. Won’t ever happen but another fantasy of mine.
        About the “Sexy Redhead” of mine, I simply can’t take my paws off of her. She’s smoking hot and wears some really sharp outfits while at work and on dates. She’s got that total sexy and cute thing going on at the same time which drives me absolutely crazy!
        Take care Elise…Gotta quickly run…Love having you as one of my coolest new buddies in Heaven here! XOXO Scarlett

  14. Patricia Marie Allen 8 months ago

    I can see that when her mate’s feminine side come to light, not just that he’s likes things considered feminine, but that he has a compulsion to express a feminine nature, she needs to redefine the relationship.

    Over the last 45 years, I’ve seen my wife struggle with that very thing. You’ve hit the nail on the head when you point out it’s not being able to understand cross-dressing. I wish someone who does understand it would explain it to me. I’ve been cross-dressing for over 60 years and don’t understand it.

    What I do understand is that my desire to express my feminine nature won’t go away, and my tolerance for hiding it wears thinner with each passing year. As I began to assert my needs in that area, the struggle my wife had grew. Fortunately, in the last 5 or so years, she’s come to the conclusion that I’m the same me she fell in love with and that we, after 50 years of marriage, have a good, solid, loving relationship.

    Women find that to succeed in a man’s world they don’t just need to be as good as a man at what ever they need to do, they need to be better to get the same recognition. The same is true for cross-dressing husbands. In order to succeed in marriage, we can’t just be as good a husband as the next guy, we need to be a better husband than our wives perceive other husbands to be.

    Each day we must prove ourselves worthy of their love. We must, without complaint, exceed any expectations our wife might have for her mate. Not an easy task. Each success counts one point in our favor. Each failure, counts ten points against us. It’s a constant battle to stay in positive numbers. But once you’ve become accustom to applying the effort to do so, the result is rewarding enough to make the effort seem trivial.

    We all, cross-dressers or not, need to remember, love in not about what you can get, but about what you give. I’ve determined to give my all in the love of my wife. In return, she matched me point for point. We joke about it, saying that we play a game called “Points”. When one of us does something the other likes, we ask, “Are you trying to get points?” My answer is “Always.” When something is even mildly displeasing we admonish, “Your losing points.” Or as my wife sometimes say, “Minus, minus, minus.”

    The object of the game isn’t to reach a point where one can be the “winner,” but for each of us to continually gain points. Hence my answer… “Always.” Always trying to gain points.

    • Author
      *Trisha Anne 4 weeks ago

      “Women find that to succeed in a man’s world they don’t just need to be as good as a man at what ever they need to do, they need to be better to get the same recognition. The same is true for cross-dressing husbands. In order to succeed in marriage, we can’t just be as good a husband as the next guy, we need to be a better husband than our wives perceive other husbands to be.”

      Powerful stuff right here! Certainly, as a CD, you don’t “owe” your wife more than any other husband, but when things are complex and maybe a bit confusing, seeing our partner go the extra mile to make us happy can lead to an appreciation of all that is femme about her. The “next guy” probably isn’t working as hard to make their wife happy.

  15. 'Eave 8 months ago

    I was fortunate that my wife knew about my dressing even before we married or even became a couple. We have been together now 28ish? years? She knows that dressing makes me a more comfortable dressing and now almost all of my close3s are fem or at least androgynous.

  16. esther 8 months ago

    I think its interesting that many married women now wear mens clothes & have real short hair, & no one cares. I know of one married couple who look so much alike that its hard to tell which one is which! Its too bad that society accepts that when they wont accept those of us that want to wear womens clothes! I fortunant that when my wife found out that i like to wear slips instead of underpants, she never complained, but she dosent want me to wear dresses in our home town. So I have been able to wear womens clothes several times when we were out of town, so that helps me to express myself. Its so much more comfortable to wear skirts than pants! I guess she is worried more about what other people think, which most of us also have to face.

  17. Smartina Fonteyn 8 months ago

    Great article. My wife has these same kind of insecurities, but we are still together after 20 years. She is something of a tomboy, so we kinda balance out. I think perhaps one factor which isn’t talked about too much is the huge changes in society itself. Women now expect to have any career open to them and average women’s clothing has become more androgynous or male. On the other side, there’s a probably more acceptance of biological men expressing female, particularly if they are committed trans. In the middle ages, rich men might enjoy silks or lace; in the modern age, men are not supposed to crave fine fabric and put up with something scratchy. It’s messed up 😉

  18. Luv Love 8 months ago

    Such a great article Trisha! I’m glad you felt my words would help others as it relates to being loved. Knowing about my partners dressing from the beginning and accepting it at that moment, I didn’t realize I’d still struggle with a few things over these 15 years. I just have to keep my pulse on what makes my partner and I work. I try to understand the desire to dress but may never fully understand it. What I do know is watching my partner grow as a person and the bond it’s created for us, I couod never have imagined it. Lots of open communication helps with insecurities on both sides and I’m grateful communication with my partner works exactly when it needs to. Thanks again Trisha for thoughtful articles! I for one am grateful to have connected with you and so many others like me. I’ve grown that much more since being here.

  19. Scarlett398 8 months ago

    Trisha Anne, this was the most insightful and well written article from the perspective of a female wife or long term lover of a male to female cross dresser!
    I could write for days in response to your article. I just hope I can soon tell my wife I’m a new member of Crossdresser Heaven and lead her to your article and have her understand many of the most important issues both the wife and the cross dresser who loves the wife even more than cross dressing face after the fact that the cross dressing has been exposed and the love for the cross dresser has not waned but has grown stronger when the wife or female significant other finally realizes the same person who loved them before the cross dressing was known still loves them as much or even more after the exposure and the words and actions that confirmed the love for the spouse before, during, and after the exposure of the cross dressing.

    I apologize for the rambling and the not so well written response to your super article. Just hope I can get my sexy redhead to read this wonderful article and have a better understanding that my thrill to cross dress has nothing to do with the amount of love I have for her and will continue to have for her forever regardless of the level of her acceptance of my cross dressing.

    Well done Girl Friend and I look forward to reading more of your writings, Trisha Anne! Sincerely Scarlett

  20. kaydee 8 months ago

    thank you Trisha for sharing your thoughts with us hugs Kate

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