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.

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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 🙂

Latest posts by Jessie K (see all)

  1. Lucinda Hawkns 3 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 showed mom. daughter said to mom its his body. but for dressing up infront of my kids, ah NO. wife knows of my desire, she lets me know when kids are gone and i can dress up. yes my wife seen me all dolled up at times but will not help with make up. or see me, i buy my own make up and clothing, yes i buy all of them, dresses, nylons, panties, pad, bras, heels, perfume. being a closet cross dresser is hard, to me its a depression drug stress free drug helps me relax

  2. Lea 3 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 part in it. I have a hard time talking with her about this topic – as a lead in, I sometimes force a discussion by intentionally letting her think she caught me, either dressed up, or a pair of shoes left out (for a few days, sometimes weeks). I deeply want to talk out my feelings, but it’s so hard to start the conversation….”So, honey, I found this really cute dress at my favorite thrift store”.

    And here I am on Sat, her at her computer, me at mine, hand on mouse ready to click close on the browser window in case she walks over.

  3. 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 packaging for a woman’s wig. She did NOT tolerate it in the least and almost left me but stayed for 11 more years before finally leaving me.

    After moving into my elderly moms house to save money and take are of her, m dressing in private accelerated and after she passed 4 years ago, it REALLY accelerated. I now dress every day -underdressing at work and then changing into full female mode when i get home and staying like that until morning. I am not sure if I will remain a CD but getting out in the world more or if transitioning is in my future. Either way I can no longer remain closeted at home-I need o let Cynthia see the world and the world see her.

    So far I have driven while dressed(day and night), walked around the neighborhood dressed(only at night), and gone through a DQ drive through (see my article “It All Stated With a Vanilla Milkshake and I am working up to going out shopping as Cyn. My oldest sis, whom I had feared would react badly is in fact my biggest supporters and of the 10 15 or so people who know or have been told about my TG feelings ALL of them so far have been accepting and loving of Cynthia! IF I can do it then so can you! I encourage you to let yourself be who you are. It is incredibly freeing!


  4. JaneS 3 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.

  5. RayannCross 3 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 i just simply went about my business. It’s easier to be Rayanne with strangers than with my family and friends, and that’s sad i suppose. But i do find peace with myself when i can dress and “be me”. Sometimes i will dress completely, makeup and all and drive home from work as Rayanne. It’s a drive of an hour and a half through several cities. I will stop at a picnic area near where i live and walk for a bit near the water before i change back into “normal” attire and appearance before going home for the evening. While i am Rayanne i can honestly say that i am at peace with myself. I feel free. My one great desire is to somehow greet the world as Rayanne. I know that you do too. Peace and love sweetheart.

  6. Kim 3 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.

  7. SIESSA 3 years ago


  8. Leonara 3 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 was confused about my new wardrobe but I had to promise that it was for us and don’t venture out underdressed.

    She would definitely not approve of my fully enfemme and my purchase of a wig. .. I did venture out to CD boutique to purchase my wig. I changed there .. You can’t try on wigs in drab!! My first”public” appearance as Leonara.
    Having this forum to express our experiences is so helpful. Thank you all for listening …

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