Dear Gabi, I Have So Many Crossdressing Questions…

Anna (genetic girl) sent me an e-mail asking for some guidance with her personal situation. She’s agreed to share this publicly so that others who have a similar situation and questions may benefit from it.

Her original message has been broken down into small sections so that I can address each point directly:

I have so many crossdressing questions that I don’t know how to address. My boyfriend is a crossdresser…

You’re not alone, Anna. Crossdressing is very much a mystery to most people. I don’t have all the definitive answers (no one does), but I’d be happy to offer my personal insight and opinion.

We dated probably a year before he told me, by then I was so in love with him that I couldn’t leave, but didn’t like it. Leaving would mean I was shallow, that our love wasn’t real.

Not all couples are going to be successful because of a variety of issues. When a breakup occurs, it does not mean that the love felt by both wasn’t real. It usually just means that two people were not compatible enough to remain together. Breaking up is never easy, but it is sometimes necessary and healthy to do so when differences are greater than the personal tolerance levels of each or sometimes just the one.

So I let him do what he did. Prayed it was a phase, but it ate at me. So after three years we split up, but two months alone was all it took for me to actually grasp that it’s just who he is. It doesn’t mean that he’s gay and that he’s going to leave me later in life for a man.

Crossdressing is no more a phase than being right-handed is a phase. I’m glad you worked out that it is indeed simply who your boyfriend is.

Some crossdressers are gay, but it works much like like it does for non-crossdressers. If someone is straight, it is highly unlikely that they will magically turn gay (or vice-versa). If your man is into women, it has nothing to do with his crossdressing, but rather his sexual orientation.

It’s no different than me being a tom boy and wearing athletic shorts and t-shirts some days than his days of needing to wear heels and a blouse.

It’s a lot like that, yes, but a little different. There is typically a need for feminine self-expression that triggers dress-up time. I prefer to remove the word “feminine” and just explain it as a need for self-expression, period. That is a need we all have, regardless of how society sees our personal preferences in appearance and attire.

We want it to be a secret from our families. I don’t think his would understand in the slightest. But what happens if we have children? They will need to see Matt as Michelle, he’ll need to do that in front of them. But eventually, especially as a toddler, they’re going to say something about Daddy wearing Mommy’s clothes… I need children though, being a mom is a strong a need in me as being a cross dresser is to Matt.

My personal take on crossdressing and children is to allow the children, from a young age, to know the truth about their father. Treat it as an aspect of everyday, normal life and your children will grow up learning the truth about crossdressing rather than being taught the lies by our not-so-understanding society.

You concern seems to be in the kids mentioning how Daddy dresses to others, and that is understandable. Kids will be kids and you cannot control everything that comes out of their mouth. You can however, lay down the law and enforce it. If certain things are not to be mentioned outside the house, that needs to be made clear to your children. I think the main factor that comes into play is the level of discipline you choose to assert with your children. You can minimize the chance of the wrong thing coming out of your kid’s mouth by reinforcing negative actions with consequences and punishment. Even so, there will always be a chance that something is mentioned and the secret gets out. You need to ask yourself if that is a relationship breaker. Only you know the correct answer to that. Also keep in mind that times are changing. Maybe your parents/in-laws will always be of the same mindset they are now, but the the next generation of youth will be far more open-minded and accepting of differences and gender expression.

How do you cross dress in public? Is this only a thing in your house? Do you go out but pretend Gabrielle and Mrs. H are just friends? We live in a town of less than 5,000. Half the town thinks we should chase the gay people out, I’m worried that they’ll never leave us alone if someone found out.

Crossdressing in public is something I’m only starting to do myself. Unfortunately, like yourself, I also live in an area that is not very open-minded (or crossdressing-friendly) and therefore put myself in danger every time I leave the house en femme. Because of this, I am taking it slow and being cautious. I may never be able to maneuver in public (in this area) with the freedom I’d like, but I will not be kept locked in my house out of fear. Depending on how things go, moving to a more open-minded location might be necessary. We all have a need for freedom in our lives. If I cannot find it here, I will go to a place I can. This is something I have discussed with my wife. She has a lot of family here that she is very close to, but understands that she can always visit (as can they) should we relocate.

My wife and I have not yet ventured out into public together while I’m en femme, but it is a topic we recently discussed as that day draws nearer. Rather than show any romantic signs of affection, we would behave as if we are two good friends. There will be no hand holding, kissing, etc. The idea is to draw the least amount of attention.

Do you shave your armpits, legs and arms? Matt [boyfriend] wants to start, and I will get use to that as well, but part of me feels like that will mean “Michelle” is taking away parts of Matt from me.

From the neck down, everything gets shaved… with one exception. I’ll leave that to your imagination. :) The first thing I started shaving was my legs. My wife used to love my hairy legs so it was something she had to adjust to. Then came the arms/hands, then armpits, and finally I shed my facial hair. The facial hair was the hardest for her to see go, but she understood my need to not be the bearded lady when I dressed. For a while, she looked at me and asked “where has my husband gone?”, as she adjusted to it. I had facial hair for several years and looked very different without it. She loved me enough to allow me to shave though. It was something that I discussed with her for a long time before shaving (each area) and only did so after she seemed willing to give me her blessing. Though I did not need her blessing do change anything about my personal appearance, I personally felt it was important that she be comfortable with it before doing so. Though how I look has changed some, I am still the same man my wife fell in love with so many years ago and she knows that.

Does your wife ever have days where she says, ‘sweetie, I love Gabrielle, but today, I just need Gabe.’? I’m worried I’ll have those days, and I don’t want to hurt Matt, but I want to ever resent this either! Is that being selfish?

Every relationship has some give and take in it. Couples routinely agree upon compromises in order to maintain peace and contentment. When Mrs. H. wants Gabe instead of Gabi, she lets me know. I don’t resent her for it nor do I take it as a selfish request. Since coming out to her, she has been supportive, understanding, and not stood in my way when it comes to crossdressing. If she wants some quality time with my man-side, quality time with Gabe she shall have. Likewise, when I need some time to be Gabi, she also understands.

The key is to be completely open and honest about these feelings with each other. How much time is spent in guy-mode vs. girl-mode needs to be discussed and worked out among the two of you. You’ll both need to be very respectful of each others feelings as you discuss this – that should go without saying. Remember – you’re in this together and how one of you looks/acts does affect both.

I love him, in a way that nothing will ever stop me from loving him. I don’t want Matt to ever feel like because it took me a while to fully accept that one day I’ll get sick of it and leave him. Advice on how to reassure those fears?

Life is change. How a person feels about another person today may not be how they feel about them tomorrow. Matt’s crossdressing is but one of thousands of elements in your relationship. There is no way to reassure him that you will not get sick of anything about him and leave… unless you’ve got some insight into what the future holds. Because most people do not, this simply cannot be done with any certainty. I think the best you can hope for is to just let Matt know how you feel about him, period. Neither one of you can predict if what makes you happy today will make you happy for all of time. You can however, choose to maintain open, honest communication and agree to work out your differences. Good communication is the key to any successful relationship.

Anna, it is commendable of you to want to learn more about the realities of crossdressing rather than just treating it like some kind of personal defect in the man you love. If there is enough love, respect, honesty, and a commitment to good communication, I think the two of you will do just fine. How ever things work out, I wish both of you all the best in life.

Related content: Dear Gabi Advice Column

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7 thoughts on “Dear Gabi, I Have So Many Crossdressing Questions…”

  1. What a great & unique Q&A Gabi! You have a nack for explaining things so well in plain english that the general public can understand and relate to! Thanks for posting this up, informative and interesting for all. :)

    1. Thanks, Raquel. I try. :) I felt that Anna’s questions were very important to address publicly because I’m sure so many women have similar questions. Where will they find their answers? With any luck, they’ll find their way here. I don’t have all the answers and can’t speak for all crossdressers, but I can share some of the experiences and knowledge I’ve acquired. I want to make a positive difference in as many lives as I can.

  2. We are in a wonderful position to help people, and that is one thing that I am still trying to wrap my head around. I’ve received many emails since I’ve been on the web, and I try to answer as best as I can.

    You have done a superb job, and I sincerely hope that this woman is aided by your educated response.

  3. Hiya everyone ,
    I am a crosdresser and enjoy having my wife just tollerating it. I have found that she is mostly worried about what other people would think if they knew .

    This is a new angle that I have now to look at and to be fair to her . I love her and would have to give up dressing if she gave me the choice of it or her.

    Good luck all of you


  4. i’m married and still want to be more of a girl then i guy i want to crossdress all the time what can i do i’m so jelous of all the clothes girls can wear i want to be like one so bad

  5. I am a biological woman and my man is a CD. Unlike some of the others, I find it super hot when he shaves and cross-dresses. It is not a “I get to imagine being with a woman.” It excites me to see him unashamedly become a woman. I love her voice, her gestures, her joy in handing a salesgirl dresses she will try on in the dressing room. SHe is “new” so is still mastering being Jasmine. The only time I get confused is when he is dressed as a man but is Jasmine. It can sometimes tell by the voice but will be happy when she has the gestures she is working on down.

    I don’t know if this is appropriate here, but sometimes she likes to wear a …[content edited]… I am not dominant by nature but do love being spoiled as she makes me special meals, vacuums, etc. He is shaved everywhere but is fearful of shaving his arms.

    I myself love her in lace and fishnet stockings with her neglige opened just enough to reveal an incongruent [content edited]. How did that get there on this hot lady?? We love it.

    1. Hi Lorelei. Thanks for sharing. :) I’m so happy to hear that you enjoy your husband’s feminine side. That’s fantastic! It really is a beautiful thing when people can truly share themselves, wholly, with each other as you and yours do. There are so many more ways a couple that includes a trans partner, can enjoy each others company, than if there was not a trans partner – both romantically and non.

      I removed some portions of your comment to minimize the potential for being flagged as an “adult site” by search engines.

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