When did you start to cross-dress?

This topic contains 36 replies, has 31 voices, and was last updated by  Mandy May 7 months ago.

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  • #100598

    Arianna Arianna
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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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    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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    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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    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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    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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    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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    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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    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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  • #101680
     Maggie 
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    I was crossdressing as long as I can remember. Wearing girls, as was back, then women’s clothes just came natural. But repressed and fought for years as I was supposed to be a boy. Always cross dressed and have now begin my journey coming-out. It has been 8 months and feel free! I do not dress all the time as I still must be male in many of my roles, but am really enjoying dressing and going out en femme!!!

    Iloveit

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  • #101570
     Leslie 
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    I started as a teenager when I would go into my mother’s dresser and put on a girdle. I was so excited by the material and the tight fit. To this day I still prefer tight fitting clothes made with silky material and/or spandex. The next item I tried was a full slip and I loved the feel over my torso. After my teenage years I didn’t experiment with women’s clothes until I was in my late 20’s when I put on a pair of panties on a whim as my wife and I were making love. That really became the starting point for my desire to buy and wear many different women’s clothes.

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  • #101271
     Anonymous
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    I started when I was around 15. I don’t know why but I had the chance to buy some underwear so I took the plunge and it was then I wore my first bra. I can still remember, some 45 years later how excited I felt and how lovely it was. I dress on and off when I can but I’m firmly in the closet, apart from chatting on CD Heaven!!!

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  • #101258
     Zoe Kay 
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    Ι must have been 6 or 7.  I just loved the pretty things the girls got to wear and saw no reason I could not wear them too!

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  • #101245
     Petra Y 
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    I started around the age of 8 to 9 years. I found my moms wedding dress in a trunk in our shed and I don’t know why but I tried it on. There was an orange dress there as well and after trying both several times I was hooked. Slowly progressed to some lip stick I found in a box and borrowing moms bras and some of her other clothes for quick try ons. Didn’t know what it was all called then. Slowed down for many years until I reached my 40s and met my wife. Told her about this quite quickly and as she was okay with it started getting my own clothes for the first time. Now have a full wardrobe and dress as often as I want.

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  • #101146
     Alexandria Divine 
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    I vaguely recall a couple of scenarios from before I was 10 years old, each of which had a minor influence on me. Once we were visiting a friend’s house, and after my baby brother had an accident (he was maybe 2-3), the only spare underwear available were our friend’s daughter’s. We’re talking toddler undies, but I was strangely compelled by  a situation where a boy had to wear girls underwear. I also recall “dressing up” with my sisters by turning one my dad’s big white t-shirts into a dress. It fell past my knees, so I just added a belt to cinch up the waist. Might have included a pair of mom’s shoes, too. There’s an old photograph of this somewhere, I believe; my recollection is a bit fuzzy.

    The most powerfully influential scenario happened when I was 11 and went to sleep away camp for the first time. The setup is a bit of an odd story, but what I remember is that the boys’ cabins and girls’ cabins (which were on opposite ends of the camp) maintained a fun but heated rivalry all week. One evening the girls stole the boys’ mascot, “Bob” (a mannequin, more or less), brought it to breakfast the following morning, and announced that “Bob” had been turned into “Barb.”

    Well, that simple, silly episode flipped a sort of gender switch in my mind. Strangely, I felt a strong sense of envy about Bob/Barb’s situation. I have aspired to be feminine ever since. I was a different person when I came home from camp that week – on the inside, at least. I started trying on my mom’s clothes very soon afterward.

  • #101133
     Anonymous
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    I first felt like wearing lingerie when I was 10 but I had a thought of crossdresser since I was much younger and yes I love the way it feel on me and looks on me I feel very sexy when I’m fully dressed as a girl and love the way it look on me and I guess because of that I started to feel a little bit of a submissive too and always wanted a friend who also has the same feelings about being a pretty girl and I don’t think I can come out of closet and let my family and friends to know that I am very much a woman inside ,and so i found this great site to explore my inner feeling with my kind of girls

    I was born a guy and as long as I can remember I wanted to be a feminine girl ,I guess some people desire to he a doctor or engineer or teacher, I wanted to be a pretty samantha. Because I’m in love with my samantha side of me cause that’s what make me happy with my dressing on and enjoying looking pretty, too bad I can’t do it all the time. Hope to share and make new friends here soon , so I can be samantha all the time with my new fems

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  • #101123
     Anonymous
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    Hi Arianna I guess I started crossdressing when I was around 5 or 6 I would spend alot of time at our next door neighbours house they had two girls and they always had the prettiest clothes Easter dresses ect. We would play out side and I allways made sure to get real dirty and wet because I knew there mother would dress me in there clothes including panties until my boy clothes were clean. The girls liked when I had to wear there clothes they would dress me like i was there doll of course I would put up a fuss but I really liked being dressed up in girl clothes. I have always thought I was meant to be a girl even my mother said when she was pregnant with me she was sure I was a girl I really wish I was.

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  • #101108
     StayAtHomeMom Laqudem 
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    I’m glad you asked that series of questions, because I’ve been wondering the same things…about myself!  I honestly can’t remember when I started (I know it was in the last three years or so), exactly how I started, or exactly why.  I think I was in Target for some entirely different purpose and wandered into the women’s clothing section where a short, lacy nylon nightgown caught my eye, and suddenly it was in my cart.  I started wearing it to bed and suddenly I was back in Target buying bras and panties and other nightclothes, and then discovered the racks at Goodwill where I could expand my wardrobe without breaking the bank.  As to why I crossdress, I haven’t a clue except that I like the way it feels and looks.

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    • #101121
       Anonymous
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      I first felt like wearing lingerie when I was 10 but I had a thought of crossdresser since I was much younger and yes I love the way it feel on me and looks on me I feel very sexy when I’m fully dressed as a girl and love the way it look on me and I guess because of that I started to feel a little bit of a submissive too and always wanted a friend who also has the same feelings about being a pretty girl and I don’t think I can come out of closet and let my family and friends to know that I am very much a woman inside ,and so i found this great site to explore my inner feeling with my kind of girls

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  • #101040
     Anonymous
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    I start cross dressing when I was 10, I started having of being submissive pretty girl and always wanted to look as pretty as I girl can be ,I done few times alone at home but not with anyone I guess I thought it may be not appropriate to my friends and wife but I am excited to find this side ,I feel like home

    And i just wanted to mention when was about fourteen i stold my friends sister panties and make up and bras and go home and try to be like her and would for some reason fantasizing of my friends sister to make me her best girl friend and let her dominate me and still do fantasies like that is that normal for me but i am straight cd and love to look like a princess full time all girly samantha but do you think being a submissive crossdresser is weird?

  • #101039
     Anonymous
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    I start cross dressing when I was 10, I started having of being submissive pretty girl and always wanted to look as pretty as I girl can be ,I done few times alone at home but not with anyone I guess I thought it may be not appropriate to my friends and wife but I am excited to find this side ,I feel like home

  • #100992
     MacKenzie Alexandra 
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    My journey began as a teenage wannabe. I cannot recall what had prompted me originally other than curiosity.  In my late teenage years, I was outed to my parents. Being naive and scared, I reacted in a way that is my only regret which resulted in suppressing my feelings for 20 years. It has only been over the past 2 years that I have embraced my femininity and am exploring it all in full.

    MacKenzie Alexandra

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  • #100970
     Patty Phose 
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    I started wearing stockings, pantyhose and heels at 4. I began dressing partly fem at 17 and fully fem at 18.

  • #100861
     Maria Troup 
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    I started at the age of 5 and started shaving at 13 started transition 53 at the age of 55 in june I will be a come a full female I love dresses and heels

    • #101122
       Anonymous
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      I there girl friend how are you , I’m new to this site and love it cause I can be a lady that I am and no one knows so I excited to make friend and be a pretty girl with my new friend and open up about my life style that nobody knows off so this is a great site to be my myself as a princess I love to be

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  • #100859
     Edie Majeski 
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    I was about 5 0r 6 when I first tried on a little girl’s dress I found. Of course, at that age, I didn’t understand why I wanted to wear that dress. It just felt right.

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  • #100784
     Ronnie Me 
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    • Started at around three when my sister would doll me up. I got in so much trouble but i loved it. Continued sneaking aroundin my sisters and moms clothes. Later in life started exploring with boys and girls. Finally now at 40 have determined that i dont want to be a girl but i love looking and feeling pretty.
  • #100741
     Anonymous
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    Hi Ariana, I was 11 the first time I fully dressed but had played around in my sisters stuff before. I remember having feelings that I was a girl back when I was 4\5. At first it was a turn on, sexual thing, but once I started fully dressing I knew this is the way I should be.

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  • #100613
     Carolyne Sherman 
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    Hi Ariana. I can tell you I was around 2-3 grade when I started. I was just in awe of how beautiful and pretty my mother was and wished I could be a pretty young girl. I even told her that I wanted to be a girl when I grew up, that didn’t go over to well. I suppose at that age there was a certain amount of sexual pleasure in wearing her things when no one was around/paying attention, but I wanted it all the time. As I grew older I knew I was meant to be a female and have had those feelings my entire life. The reality I was a tg and not a cd was long coming but after I accepted that it made life easier. Unfortunately I waited to long to make a change in my life and have made peace with my situation and limitations.

    🍷C

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    • #100614
       Arianna Arianna 
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      i see,thank you for sharing your story !

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