Tag Archives: confusion

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, Am I Wrong Wanting to be Who I Feel I Am?

Debbie DanielsDear Gabi,

I have been dressing since my early youth… 5, again at 8 and again at 12 and pretty much weekly after that I am 51 years old and married with one 5 year old child at home. I only wear panties here at home for that is all I own… no male briefs… nada. My wife knew of my crossdressing before we were married and accepted me. My problem now is that I can not dress any longer at home because of our child, so I take it elsewhere. Mainly to a gay friends house . I am hetero and my friend hits on me all the time as Debbie but never as Dave. For the past 3 – 4 years my dressing en femme has become very aggressive, and honestly that is all I want to do. I am at a point right now in that I would like to start hormones and transition to female, for that is who I truly feel inside. Dave has only been there out of fear, and to take care of his family. I actually get very depressed if Debbie does not get to play and even am Bitchy. I feel the urgency more so in my life today than I did years past. What to do? Debbie is who I befriended in my adolescent years and have came to love immensely. Even my family. Sisters, love having Debbie around to go out with and such.
Continue reading Dear Gabi, Am I Wrong Wanting to be Who I Feel I Am?