Confessions of a Cross-Dresser:Part I

Confessions of a Cross-Dresser:Part I

Rachel is a cross-dresser who is married with children and works in construction. This is the first part of an insightful candid interview with Rachel as to the challenges of being born a cross-dresser.

You said you were 7 years old when you first were interested in trying on woman’s clothes. Tell us about what you were first attracted to? Your mom’s or sisters clothing? What prompted you to want to try these clothes on?

The first time I remember wanting to cross-dress; I just had an idea to play dress up with some girls. It felt like a good idea and fun. I didn’t think it was wrong. At some point an adult came by and told me that boys shouldn’t do that and I should change my clothes. It was fun and normal to me.

Did you ever get caught in the act of cross-dressing as a teenager? If so, what happened and how did you feel about it?

About the time of puberty, I was drawn to clothes again and would dress in my sister’s clothes when alone at home, but never got caught in the act.

Were you drawn to the clothes only or did you try on make-up and want to look like a girl?

I didn’t try make-up on because I was afraid I would be caught if some of it was missing. The attraction to dressing was strong and occupied my thoughts.

How did you deal with this issue of cross-dressing? Did you feel self-loathing knowing that this is something a guy doesn’t do

It didn’t make sense to me that I should want to do this and I began to feel bad about myself and I began to feel like an outsider, like no one would understand me or I didn’t fit in with other boys. I tried to be a tough, macho guy and got into trouble at high school basically trying to prove to myself and others that I was a real man; real men don’t do this.  I thought where do I fit in here?

Did you think you had an issue with your gender or thought you were maybe gay?

I never questioned my sexuality as I was strongly attracted to women.

How did your need to cross-dress affect you? Did you get messed up by it and turn to drugs or alcohol as a way to deal with your pain?

I discovered alcohol at 15 years old and found out I could forget my problems if I got drunk. This just exacerbated things, of course with legal problems, DUI, and suicidal thoughts. I later found AA (Alcohol Anonymous). Learning to live sober involves dealing with all of this. And being honest with yourself. 

Did you ever see a psychologist? If so, what did they say about your need to cross-dress?

I got busy-a short time later I confided in someone about my cross-dressing and they referred me to a psychologist. I worked with him for several months and was told that I needed to accept my behavior as it wasn’t wrong, or harmful, and that there didn’t seem to be anything else wrong with me.

Did the psychologist offer you any answers as to why you wanted to cross-dress? Did they make you feel more self-acceptance about your cross-dressing?

I was 24 at the time and he told me that the behavior was more of a stress-reliever  and that people do all sorts of things to relieve stress and it was a lot safer than sky diving, so rather than try to change my behavior, to stay with it. He said that there was no explanation for cross-dressing like you had a strong mother figure or you dress because you have female chromosomes or any of that. I got tired of paying to hear I was fine, so I stopped seeing the psychologist.

Since I didn’t have to share with anyone that I was a cross-dresser, it was easy to deal with that, I was fine. I would dress occasionally at home when I had time and figured that it would be that way as long as I lived. Then I fell in love.

When did you tell your wife about your cross-dressing habits and what did she say?

Practicing the honesty part of sobriety, I felt I needed to let my girlfriend know about me before I proposed. It’s the scariest thing I have ever done! It came out of my mouth like…Dear, I’m a serial killer, and do you think you could stay with me? She took a few days to think about it and got back to me and said, “If I don’t see it, I love you and its okay.”

Did you and your wife ever go to therapy together to help deal with your cross-dressing?

Actually, prior to marriage we did some couples counseling and cross-dressing was addressed and handled.


Check back for more on Rachel’s journey into cross-dressing in Part 2 of this series on Confessions of a Cross-dresser. Thank you Rachel for telling your story.

Leave a comment