When did you start to cross-dress?

This topic contains 36 replies, has 31 voices, and was last updated by  Mandy May 4 months ago.

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  • #100598

    Arianna Arianna
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    Registered On: May 22, 2018
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    I’m curious about your stories, when did you start to cross-dress and what made you do it? Was it the feeling of wearing girl clothes, was it the excitment?

    hope to see some of your answers

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  • #110919
     Mandy May 
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    The first memory I can remember of me exploring my feminine ways was when I was about 10 years old. I have an older sister who was just starting high school at the time and I can remember all of the dresses and skirts she was wearing to school and thinking how pretty they were for some reason and wondering what it would be like to wear them. Fast forward about a week, I was about to get into the shower and sitting right outside my sisters room was her laundry basket with her clean clothes. I walked over to it and started looking through it when I came across a white cotton thong w/ a picture of a cherry. I grabbed it as fast as I could put it in my pocket and went into the bathroom to shower. I turned the shower on, got undressed and pulled the thong out and slipped it on. It was such an unbelievable feeling, no idea why but I was loving every second of it. I couldn’t stop looking at my butt in the mirror lol. From there on out I probably wore a pair of my sisters panties everyday. 14 years later and I’m exploring my feminine ways more then ever. I have at least 100 pairs of panties, 20 bras, a bunch of different outfits, and dress as a girl whenever I can. I’m starting to realize I might be more comforts k when I’m presenting as a girl…

    #110667
     Patty Phose 
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    I was 4 and had a fascination with women’s legs in nylons. I liked to get close and touch them. My parents made me stop. Dad was harsh. Mom didn’t like that. She gave me stockings and pantyhose to play with and let me borrow her heels. I began wearing the pantyhose and heels with a long shirt that looked like a short dress.

     

    #110535
     Ashley 
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    One of my very first memories as a child was that I was playing in a family friend’s pool. I was just starting potty training and I had an accident. My mother didn’t have any other underwear for me and the house we were at only had little girls. My mom’s friend gave her a pair of white panties with lace trim on the leg holes.

    Fast forward to 10-11 years old and I found a pair of my mom’s black satin panties, I felt compelled to try them on. I had the most wonderful feeling ever when I pulled them on and felt the satin over myself. It was a very sexual satisfying memory and made me a cross dresser for life. I was hooked.

    #110266
     Anonymous
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    I think I was 7 living in Ohio by lake Erie. I put on my moms panties and pantyhose and the thrill I got was so joyous and the material was so soft I was in heaven. The saga continued to today and my impulses of old have not diminished but have grown to a full blown need to dress and express myself as a woman. TTFN

    Danielle

    #110251
     Leah 
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    Registered On: June 13, 2018
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    I started to dress when I was 4/5 yrs old.  Just in panties, then I found pantyhose drying in the shower and how great they felt.  After that, a bikini bathing suit or maybe a bra but it quieted down until mid teens and started top pick up while in college, grabbing that lone pair of panties that was in the lost n found.  I have a large collection of lingerie and this past year bought my first skirts, tops and a wig to go along with trying out make up

    #109574
     Stephanie Flowers 
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    Started around 12 myself with a flower dress I aquire from old clothes destined to be throwing up had it for many years then with everyday life I stops but many years later the urge came back. Today I’ve assemble a small wardrobe enjoy dress up as much as I can🌹

    #109568
     Jefferina Pantywaist 
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    Registered On: July 5, 2018
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    I was born in 1957, and I was about 13 or 14 when I first ever fancied wearing Panties, also nylon stockings.

    At about this point in time, I was needing some new underwear, and told my folks I’d like to have Panties, and they let me know in no uncertain terms that I would drop that idea if I knew what was good for me!

    At age 49, it came back to me that I really would like to wear Panties, and after trial and error buying different brands in different sizes, I found my way and started catching up on the fun I’d been missing out on for so many years!

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    #102268
     Martha Lou 
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    Registered On: December 11, 2016
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    I had the urge throughout my life. However< I was a late bloomer.

    I first cross dressed in a beautiful 116″ hooped skirt as a lady of the 1870’s for a costume party with all the extras: lace pantellettes, hooped lacey petticoat, makeup, jewelry, wig and a string purse.

    After that I was hooked on dressing as a woman. As a matter of fact I realized that underneath it all that I  really a woman! . Am now a transsexual lady

    I just love to dress and act like a woman.

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    #102264
     Nancee Smith 
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    Hi All

    My first recollection is being very young and in a dressing room with my mother. I was fascinated with the lace around the hem of her slip and wanted to touch it. When I was eight I was home with Rhuematic fever for three months , one afternoon when my mother went shopping I tried on a pair of her panties that were washed and folded in a basket.  I’m sure the feeling of putting them on is the same feeling I still get today. I always describe it as “that wonderful feeling” I purchased my first panties at a Kmart when I was 16, that was 44 years ago.

     

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    #102039
     Sassy Stacy 
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    Registered On: May 16, 2018
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    The first time I cross-dressed was when I finally gathered enough bravery to buy some girl clothes from the store. It was a long cotton dress with spaghetti straps, the type you’d wear at home or on hot days in summer.

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    #101930
     rebekka moore 
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    Like many gals here I was between 10 – 12.  I was playing with a group of friends and had to use the bathroom.  I went into my friends house and shut the bathroom door.  Hanging on the back was a silky, sheer black negligee and for some reason was compelled to put it on.  I stripped down and put it own, and I was hooked!

    After this episode it was a bit later that I started putting on my mom’s underwear and pantyhose.  As a late teen I actually bought some of my own and would play whenever possible.  The first time I shaved my legs I was really in heaven.

    Today I live a “straight” life and it is very difficult as the urges get very strong.  My wife has called me on the carpet for shaving.  Makes life very difficult.  She knows I have “dressed” in the past and does not accept it.  I’ve gone to “hybrid dressing”, my term, where (on weekends) I get up early, shower and put on panties (and sometimes a cami), under my male shirt, but almost exclusively wear womens jeans.  The tighter the better.  I will also wear trouser socks or knee highs, and I’ve bought a few pairs of “booties”, the short boots women wear.  They tend to be very generic looking, but are a turn on because I know they are meant for women.

    People notice at times, but I feel so good in these clothes I don’t care!

    What do others do?  I so want to “come out”, and have fun with gurls!

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    #101893
     michelee 
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    Registered On: September 28, 2016
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    As most young boys do, I had these fleeting fantasies about women’s clothes.  It wasn’t until I realized that I was bi-sexual and started dating men that I realized that I truly had a feminine side.  One of my dates asked me to dress for him.  I wore a teddy, hose, and 4″ heels while making love and the race was on.  I was 30 at the time.  As the years passed I was never able to dress in femme mode full time.  I never was nor will be passable, sad to say.  But I just love the feeling of being feminine.

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    #101823
     Marcie Rose 
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    I started when I was 10 after my Dad died.  I don’t know if his death triggered it somehow, but I was home alone a lot since my Mom worked full time.  I was curious and tried on her clothes and wig, and it just felt right for me.  That was 40 years ago.

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    #101817
     Marie Bardinot 
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    Registered On: December 26, 2017
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    I don’t actually recall the exact age I was, but it was when I was really young. Elementary school or maybe earlier. Pantyhose were some of the first items I tried, but my cousin slept over for a week and she wore a little babydoll that I actually got to wear one night.

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    #101688
     Michelle Liefde 
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    Registered On: May 27, 2018
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    I was 11 the first time I dressed in my mom’s pantyhose, underwear, bra, dress and a wide brimmed hat.  I remember how amazing it felt and how exhilarating it felt.  Within the last 2 years, I have started again and that same feeling is there.

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