In every crossdresser’s life, there is a period of time in the closet. I was in the closet for about 15 years. While I wish I was upfront about my cross dressing habits with my mom/other loved ones, I couldn’t bring myself to do it. How would I ever walk up to my mother and say “Mom, I like to wear your clothes while you aren’t around”

Instead, I chose the safer, more relaxing route: Dressing in my room while no one was home. But while I was safe, I never had any stories, never opened up to anyone, and rarely had time to dress (seeing as how I had to make sure my mom, dad, and two brothers weren’t around). My only solution was to take some of my moms clothes out of her closet and hide them where she wouldn’t find them.

There were, of course, some close calls. I was sitting in my moms closet enjoying wearing some of her boots when my brother walked in. I was lucky enough to be in my mom’s room, which had a bathroom inside. He, thankfully, didn’t check what I was wearing on my feet, and I rushed to the bathroom and took them off there. My mom must have been very confused to find her boots hidden in the shower, because they weren’t there when I went back.

Exceptional Voice

I continued to not let anyone know of my crossdressing endeavors, keeping them locked up in my room or in a bathroom. I would pretend to watch T.V. in my mom’s room. When no one was looking, would slyly take a dress out and put it on in the bathroom.

Then she DID find them. I remember cleaning the basement with my mom when she all of a sudden went “Well how did these get here?” She was holding up the heels I hid behind some boxes. I stammered “Umm…I don’t know” and there was no mention of it ever again.

By age 14, I had sort of grown more than just ‘Wear shoes and then call it a day’. I had started fully dressing up at age 13, so I had hid the essentials behind a bunch of clothes in my closet (the essentials being heels, leggings, jewelry, a shirt, panties, a bra, and a purse). My mom was again, looking for heels that just happened to go missing (I had really liked shoes, ok?) when she found my stash. I couldn’t really think of a logical explanation as to why that was all hidden there. I had been caught, and I couldn’t bring myself to say “I’m a crossdresser.” I was lucky enough to have an understanding mom, and she hugged me and told me that she still loves me.

There was, after this day, no mention of it since, and I eventually started dressing more and more. I still haven’t told anyone else, and I still would make an attempt to hide what I’m doing  from my mom.

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I think that being out of the closet would be a difficult choice to make (and any ladies here that are completely open, I respect and envy you) and I wish I could muster up the courage to just fully dress. Maybe one day I could, but for now, I’ll just be Jessie in the closet.

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Jessie K

I'm a 22 Year old crossdresser who started when I was 3, trying on my mom's heels when she wasn't around. I was instantly hooked and have been crossdressing since. I'd love to share some experiences 🙂

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Lucinda Hawkns
Active Member
Lucinda Hawkns (@dlgeb275)
4 years ago

that was so good and true about telling family that we are cross dressers, its hard. dont know what the reaction would be, but for some women now days they like that in a man, dressing up as a female, they would even help you with make up and really pass as a female. then there are others who think different. for me i was a closet cross dresser for many years, my grandmother knew i wore her dresses but kept it quiet, later in the years my daughter seen a pic of me all dressed up really pretty and… Read more »

Active Member
Lea (@lea-jhene)
4 years ago

Thanks for sharing Jessie. It’s ironic how good we become at keeping secrets and hiding stashes of items. Then, it’s ironic how hard it becomes to reveal those secrets. I used to do the same things as you, sneak away from the family to dress in the bathroom or my bedroom, hide things behind stacks of clothing, and almost/got caught a few times. To this day, I still think I’m good at hiding what I want to hide. I revealed my secret to my wife a few years ago, she’s sort of neutral on what I’m doing, but wants no… Read more »

skippy1965 Cynthia
Trusted Member
skippy1965 Cynthia (@skippy1965)
4 years ago

Lovely story JEssie! So many parallels t many of us I was caught nearly right away by my dad wearing one of sisters’dresses and pantyhose. He made me take them off and talked to em about it. Said may boys are curious though most grew out of it. He asked me if I wanted to BE a girl-I said no (though truly I wasn’t then and still am not now) sure if that was an honest answer. I dressed secretly when I had the opportunity growing up and then got caught one year into marriage by my wife who found… Read more »

4 years ago

The closet can be a place of safety and security but once you step out of it you’ll never want that inside view again.

Taking that step, though it may seem difficult, isn’t as bad as many imagine.

Best wishes.

4 years ago

Jessie, your story is all too familiar. Being in the closet is emotionally, the safest place to be for me as well. Though i recently have begun to come out in my own way. I haven’t been able to show my loved ones who Rayanne is, but i have been going public in small ways. I will go into the Salvation Army store to shop for clothes wearing nail polish and a light colored lipstick once in awhile. I recently wore heels and a skirt while i pumped gas into my work van. I turned a lot of heads, but… Read more »

4 years ago

I got the pleasure of coming out to my mother just before she died. It was wonderful and stressful all at the same time. It is something I’ll cherish forever, getting to go shopping with her was incredible. I miss her so much because she didn’t judge she just loved.

4 years ago


Active Member
Leonara (@leonara)
4 years ago

Hi Jessie ..thank you for sharing your story. It is good to know there are other closet CD’s out there… I dress fully enfemme when the opportunity presents itself . It is very relaxing and love the feeling of being a lady. One night my wife and I were talking about my Curiosity about panties. She dared me to try one of hers. The next day we went shopping for me … She picked out Bali panties and Hanes ultra sheer stockings and a camisole… It was a very “interesting” night. Howeve, a few days later she confessed that she… Read more »

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