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.
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.
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.