Tag Archives: Dear Gabi Advice Column

Dear Gabi, I’m a Crossdresser and Don’t Understand Myself

Dear Gabi,

My name is Casey. I’m an 18 year old male who enjoys cross dressing but is very secretive about it. I am straight. I have not told many people, and don’t get an opportunity to do it as often as I like. I have a lot of questions and stuff to get off my chest.

I have only come out to four people. I came out to my parents when I was in the sixth grade, because I was going through puberty and didn’t understand my brain. They were both fine with it and didn’t love me any less. However I think as far as they’re concerned I’ve stopped cross dressing. We haven’t talked about it since. I shouldn’t have a problem with it because they are two of the most loving, liberal, open minded people I know and every day I’m grateful that they’re my parents.

I openly describe myself to people as flamboyant, and when I say it, I say it proudly. I am proud that I do all the no-no’s of being a manly man. I love my girly side, I just wish I could express it more. I suppose I get along better with girls (except for my best friend in the world who is a guy) and the ones I am friends with are open and loving. My two friends here at college would probably be fine with knowing I’m a cross dresser but I freeze whenever I even think about telling them. I’ve told two other people besides my parents. Purely by coincidence they were both girls who were struggling with their sexuality. One of them is now my best friend on campus, and we talk about the subject all the time.
Continue reading Dear Gabi, I’m a Crossdresser and Don’t Understand Myself

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 Feel Envious of Pretty Girls

Dear Gabi,

I’m having issues with Girls. I feel a lot of envy towards Girls, and it often leaves me feeling so upset I can’t focus on anything else. I feel teased whenever I see a pretty Girl walking down the hall, or come up to talk with me. It gets so bad sometimes I end up feeling really awful about myself.

I don’t want to feel this way about Girls. I know they aren’t teasing me, but I can’t help but feel inferior. Please help!


Continue reading Dear Gabi, I Feel Envious of Pretty Girls

Dear Gabi, My Crossdressing Boyfriend Just Came Out but Now He’s Nervous and Depressed

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?


Continue reading Dear Gabi, My Crossdressing Boyfriend Just Came Out but Now He’s Nervous and Depressed

Dear Gabi, Why Do Men Crossdress? Many girls are just curious.

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.


Continue reading Dear Gabi, Why Do Men Crossdress? Many girls are just curious.

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 :)


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

Dear Gabi, My Crossdressing Honey Feels Like a Freak

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??


Continue reading Dear Gabi, My Crossdressing Honey Feels Like a Freak