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.

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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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  1. Chrysta Minot 4 months ago

    Thank you so so much, Trisha. I am in a 23 year loving relationship with my wife; we are raising a beautiful 14 year old son, and am just come “out” with my relationship with my inner “girlfriend”; and all kinds of physical symptoms are dissipating in my body, slowly released from to decades of low level repression. There is magic and mystery in the air. My wife is a little bit hesitant and uncertain, from her insecurities and unfamiliarity with the whole scene. But I am looking forward to periodically being the beautiful, kind, classy, compassionate, sensitive girl I am inside, with her support. I bring all kinds of “manly” things to the table of our relationship (eg, a few days ago I installed a new dishwasher!) and also she loans me her skirts to go dancing in, and is giving me tips on places to shop for delicious girl stuff (eg mascara, skirts, leggings etc) with a friend. I told her, “Let me be as much the woman I want to be, and I’ll be more of a man for you than you ever dreamed of.” I build things, fix things, lift things for her and am a great massage therapist for her and my family. I’m also thrilled to be getting my first wig and make up kit soon. Oh, my goodness, it is so scary and exciting. I wake up early before the alarm, thinking about my lucky life. It’s like a part of me that’s been ‘waiting to exhale’ for 50 years, is finally letting out a sigh of relief and pleasure. Thank you, Trisha for your warm and thoughtful article. This chapter in my life is indeed scary, and yet wonderful, and you have helped me remember I am not alone! God bless, and Tally Ho!

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