Tag Archives: advice

Being a Successful Trans Woman in Public without Passing

Gabrielle Walking 2 2014-07-06

Passing without passing
The photo above shows me walking through a local mall carrying my bag of goods. That’s how I look to most people – just another random woman shopping in the mall. Until, that is, someone looks directly at me from 20 meters or closer. Contrary to the carefully chosen photos I post publicly, I don’t pass – not in person. Most people read me as trans without missing a beat. More importantly, most people treat me very well.

The right attitude goes a long way
Years ago, when venturing out into public I’d get laughed at every time. Getting laughed at, disparaged, and called names by homophobic/transphobic cowards made me self-conscious and fearful of going out. In retrospect, I understand the difficulties I used to experience.

Other trans women frequently told me, “It’s more about attitude than passing.” How can attitude affect how one is viewed by others? It took me a few years to figure out. Having the right attitude in public can be the difference between having an amazingly positive and enjoyable experience, or not. It’s a little like a magic trick, but it’s not magic. There’s something more powerful at work, and it’s not just attitude, either.
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Dear Gabi, I Feel Guilty & Fantastic and Don’t Know Where I’m Heading Next

Dear Gabi,

I’ve just been reading your site for hours and I just wanted to drop a line to say how much of an inspiration you are. For the past few months I have been trying to figure myself out, one day I just felt a physical need to dress up, wasn’t something I was born with or anything it was a moment. I don’t know why, it just happened and kept developing. I’m married, have a kid and am tied with this double life. I purge and purge but as your site says, it’s a quick fix to feel what society classes as ‘normal’, the next day I had the yearn again.

I love having something private that I can keep to myself but feel the guilt too whilst also feeling fantastic and complete as everything about me is able to be expressed. I work in a very masculine environment with my family in-law expecting a very masculine role model for their daughter but as your site made me realize, too much of something has suppressed something else that needs its venting too!

Your site has given the many answers that many people have no doubt gone through, I don’t know where I’m heading with this next but I feel like this part of my life is a new body part you can’t live without. It’s nice to see someone like you who’s so free and liberated after going through all the same hardships as everyone else and still accepts they too are still learning about themselves. Well, here’s to happiness!


Continue reading Dear Gabi, I Feel Guilty & Fantastic and Don’t Know Where I’m Heading Next

Dear Gabi, I’m a Young Crossdresser Confused About My Sexual Orientation

Dear Gabi,

I’ve just recently discovered your website and wish I would have earlier in my exploration of crossdressing. ;) I’m 18 now and have accepted who I am, been dressing up since I was young, 5 or 6. I’ve come to terms with a lot of stuff, and I’m no longer ashamed of who I am. I have a loving girlfriend for almost a year now who knows everything as well, she is very accepting and supportive =)

My problem deals with my sexual orientation, I know I’m attracted to girls, thus my girlfriend, but while dressed, I find I’m always craving guys, so for a while I just thought I was bisexual, until when I was 16 had my first relationship and sexual experience with a guy. Now he was a full time crossdresser, even during high school, I think that was the main attraction. I was so turned on being with him, and kissing him. Anything to do with touching or seeing his genitals didn’t turn me off, but didn’t turn me on. I love the feeling of anal sex (from a male), turns me on immensely.

So basically I’m kind of confused, I look at a normal guy and I’m not turned on, but I always find myself thinking about having sex with a male and strap-ons with my girlfriend just doesn’t feel the same. I know it’s a vague question as well, I’m still young and exploring and advice would be amazing :)


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Dear Gabi, My Wife Thinks Crossdressing is Wrong

Dear Gabi,

How best to handle it with my wife is my biggest concern. In the past I had felt that crossdressing was wrong and therefore had purged my collection several times. Now for me personally, I am comfortable with it. I had been trying to decide how to talk with my wife about it when she discovered.

Since then she has expressed the viewpoint/belief that (A) per the Bible and society crossdressing is bad and wrong. Absolutely no wavering on this so far. (B) She also believes that it is something that if you try hard enough you can stop doing it.. She has also stated from watching Jerry Springer show that all crossdressers will become gay at first and then that leads to all getting a sex change operation. For the most part she presents to me as these being absolutes.

She has also remarked that now all she can think of me as is Georgette whether it is just kissing or anything else. She also feels that if she would of given me sex more often then I would not want to cross dress. I have/had a web blog where I was journaling/logging my experiences. She wants me to get rid of that to. Currently I am doing that.

In addition to all this, I feel like she wants me to make all these changes and stop dressing and because she says it is wrong.

Yet at the same she does not what to consider or accept any offers for compromise.

Thank you,

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Dear Gabi, Discovered by Wife… HELP!

Dear Gabi,

Thanks for your page, I will be back to visit. I have dressed off/on since 5 years old. In an off phase went dated and married.

Had gotten back into and understand and accept now that it is part of me and great stress relief. Almost cost me my job due to poor reaction to stress.

I was trying to decide how to talk with my wife about it and left a journal site open. Now she knows before I was quite ready. I have seen your How to Tell Your Wife You’re a Crossdresser page but am looking for any other help tips there might be. If you have any, thanks.

I haven’t looked at everything here but your en femme pictures are awesome, you make very nice looking woman. If I can get half as cute as you I will be happy.

Good luck and enjoy in the future.


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“Dear Gabi” Advice Column

Gabrielle HermosaFor some time now, I’ve pondered the idea of offering an advice column. Not about fashion or makeup tips, but rather for crossdressers and their loved ones who are dealing with confusing feelings and would like some guidance on the mental health front.

Most of my life has been spent analyzing and trying to figure out what this all means. Confusion, guilt, low self-esteem and depression used to be the status quo for me. It’s been a long, difficult journey to self-acceptance and inner-peace, one that I almost didn’t survive, but I made it and learned a wealth of knowledge along the way.

This website was started with the intent to educate people about the realities of crossdressing and dispel the negative cliches and myths. I try also to offer insight and guidance for crossdressers who are dealing with their own issues and generally don’t feel good about themselves because of this aspect of their lives. Publishing an advice column seems the next logical step. It will allow the opportunity for an additional level interaction and communication with visitors.

A Dear Gabi link has been added to the navigation bar up at the top. Questions can be submitted using the form on that page. The content of the submission page may go through updates as things get ironed out, but it’s a good starting point. I encourage you to take a look.
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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.

Continue reading Dear Gabi, I Have So Many Crossdressing Questions…