Dear Gabi,

My name’s Angel and I have a crossdressing boyfriend, “Sullie”. We’re still in highschool, and have been dating for two years, but I’ve only just found out that he’s a crossdresser because he has been afraid to tell me because of how I may have reacted. I fully accept him, and try to encourage him to be himself no matter what. I am 1 of 5 people who know, but none of his friends or family know.

I’m almost sadden by the fact that he had took so long, after I’ve been very vocal on my opinions about Gay, Bi, Lesbian and etc decisions in life. I myself am Bisexual, but Sullie’s the only person for me.

He’s become a shell of himself and is still nervous when he dresses around me. He feels he is a freak, and “not normal.” This is what saddens me the most. His acceptance in society won’t be felt for a while. Like said, I fully, 100% support him in any way possible. He is himself, and that’s what I fell in love with, nothing less.

Our first year together, he wasn’t the most faithful, but something held me to him. Something told me to stay. After he came out, things have been so much better. We are stronger, and I can honestly say, I have never ever felt closer to him.

Sully has always had a quality about him, a shy nature. But as he has progressed in his nature and sexuality, he’s become ashamed of himself – not at all times, but it’s definitely a mental state of depression that I hate to see him go through. He’s never been sure of himself, inside and out. Now that I know, it’s boosted him slightly, but not enough for him to come out as Sullie to other people.

I sometimes get frustrated because some of the comments his friends make without knowing honestly offend him, but he can’t say anything. He’s 16. Do you have any advice for us? And advice for confidence for him?

Angel

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Posted by Gabrielle | 4 Comments »

Dear Gabi,

I am a straight SWF and actress. Can you explain why some dressers are straight, some are bi, and some are gay? Do they find dressing sexual at all? Do they have a special id with their mothers or sisters? Does each prefer specific items of clothing, or soft, silky fabric? Is the attraction to the clothing, or the idea of being a sexually appealing or soft female? Would they be more attracted to a more feminine or masculine looking and acting woman?

I have encountered many cross-dressers in Las Vegas, in and out of the entertainment industry. Most are very shy about revealing their preferences. Most surprising is that most focus on one specific garment ie shoes, lingerie, mini-skirts, that is associated with female sexuality. That is why I was trying to understand the psychology behind it.

Thanks for your response. Many girls are just curious.

Davida-Rochelle

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Posted by Gabrielle | 15 Comments »

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 :)

Angel

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Posted by Gabrielle | 9 Comments »

Dear Gabi,

Three years ago, I hooked up with my (yes, this is a cliche) High School SWEETHEART. We’re both in our late 40′s… divorced… kids… yawn yawn blah blah. He came out to me about 9 months after we re-initiated our relationship. He’s a cross dresser. Her name is Kelly. I am all for it. No problem. Be what makes you happy. Life is short. But it doesn’t always make him/her happy. He thinks he’s a freak. His ex never knew this about him. He’s known his whole life. What can I do to convince him that all is good… I love “them” the way they are. It’s now been 3 years. I moved from California to Michigan during an American financial crisis for “f” sake. I love him. Have since I was 14. I come from the land of fruits and nuts. I refuse to judge anyone… EVER!! Living in this closed minded world I have found Michigan to be is not an easy transition, so I understand his trepidation. HELP!! The people here have stunted his mental growth! He fights with me. When he’s Kelly… all is good until something (ie the door bell rings) sets him off. He becomes paranoid and rips away Kelly faster than you can sneeze. Then proceeds to be depressed for days! I have his back! He’s not alone anymore. What more can I do??

Lori

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Posted by Gabrielle | 13 Comments »

Dear Gabi,

I have just approached a therapist about some sessions as I feel my crossdressing is starting to effect my relationship. My girlfriend is understanding in a way but is still not overly keen.

It is just me who will be attending, as we both feel there are issues I need to address which could all be linked. Short temper for no apparent reason like I get really mad about the most silly things. My girlfriend thinks it’s always before I need to dress. She does not want to see me dressed though. I think I need to get a good understanding of why I need to dress other than “I love that dress!!”. I feel I’m rambling on a bit so apologies for that. I don’t wish for it to go any further than our home but I don’t want to always be alone when dressed but not sure she will ever want to get involved.

I just wondered what is the main objective of this type of therapy. I am nervous and not sure what to expect.

Best regards,

Tina
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Posted by Gabrielle | 10 Comments »

Dear Gabi,

My wife just found out I am a cross dresser (I have been as long as I can remember…), and reacted very badly. I don’t know where else to turn… none of my friends would understand, and I still think most of them would not speak to me again if I told them…

My beautiful, brilliant wife, the love of my life, and the only person I would ever want to spend my life with, has told me she would have stopped dating me if she knew I was a crossdresser, and has told me she will never be able to deal with me being a crossdresser… she has done the research, she understands I am hetero, and not gender confused, but she says she just cannot deal with me being a crossdresser… she has told me that one of us has to move out, that she will not change her mind, and that she will never be okay with this…

I have a beautiful family, and I don’t want my son and daughters growing up in a broken home! But I don’t know what to do, I don’t know what to say to make it better, to make her understand I am still the same person!

You have already been so much more help than I could ever have expected, and I don’t even know what I am asking you for… There is no magic word or phrase that will make this all okay, I know that… I guess it just hurts so much and I needed to vent and I just don’t have any other place to go… This is just so hard, and I don’t know what to do…

Nora
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Posted by Gabrielle | 23 Comments »

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,

Georgette
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Posted by Gabrielle | 20 Comments »

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.

Sincerely,

Georgette
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Posted by Gabrielle | 4 Comments »

Dear Gabi,

I am a crossdresser and I am really anxious about my parents finding out. Should I tell them or just keep hiding it?

Anonymous

Deciding whether to tell your parents about being a crossdresser or keeping it a secret can be a tough call. The anxiety felt in being discovered is very understandable – I was once there myself.

What is right for one, may not be for another and this is a decision that you must make for yourself. In the end, telling your parents will probably work out much better for you than being discovered or caught by them.

There are many things to consider before discussing with your parents. I suggest you give serious thought to the following:
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Posted by Gabrielle | 5 Comments »

Dear Gabi,

I have been having a really hard time adjusting to my boyfriend crossdressing. He told me when we had been together for two months. It has been a year since he told me and I am still adjusting. Is it normal to adjust so slowly? I guess I feel that I’m not in a normal relationship, and I feel like I am not the only girl in the relationship at times. He is very manly all other times and I love him so much. We live together and he is amazing.

My Problem lately has been that I feel I am taking pictures for everyone on the internet to see. He posts them almost immediately after I take them. He says that he feels sexy when people comment them. Another thing is that I want to dress up in sexy outfits too, but he never asks me to.
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Posted by Gabrielle | 8 Comments »