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Thread: How did you start dressing

  1. #1
    Junior Member KIM SLIMS's Avatar
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    May 2008
    New Jersey

    How did you start dressing

    Hi I was wondering how we all get started. I started with my sisters clothing like panties and bras got into jeans and dresses. I was busted by my mother one day. She was not really ok with it but she did take me shopping for my own girls clothing. When I was 18 I only had girls clothing to wear

  2. #2
    Aspiring Member Star01's Avatar
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    Aug 2018
    Got into some clothes in the attic in 1964 at thirteen. First gender related memory was Superboy #78 story about being changed into a girl. I was probably around 8 and vaguely recall expressing a desire to be a girl. I remember a blowup between my parents about me and comic books and I think there is a connection.

  3. #3
    Join Date
    Nov 2009
    when i was about 15 years old or so, my mom and i were at the mall and she asked if i wanted my ears pierced. it was popular then, and then i started wearing her earrings all the time and fell in love with the feel and look of girly earrings. i started wearing more of her clothes and it spiraled from there.
    Last edited by shortskirt87; 03-14-2021 at 10:26 AM.

  4. #4
    New Member
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    Mar 2021
    I started with pantyhose. Loved the feel and look. Id "borrow" them from my mom. It then progressed into panties. That lasted up until high school. I got busted a few times and was forced to go to counseling. I stopped through high school and regained a love for panties and hose in college. That progressed into being able to dress since I was away from home. Now 10 years later and I dress when able.

  5. #5
    Junior Member stefaniec's Avatar
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    Feb 2021
    Fayetteville, NC
    My story is pretty similar to most. I started to notice and be attracted to girls around middle school, but part of what I was attracted to about them was their cute uniforms (private school) and tights they could wear. As a kid, there was just a big basket in the laundry room where everyone put their stuff that needed to go in the wash. So one day when I was putting some clothes in the washer, I noticed a few pairs of mom's pantyhose in there from the work week. I was really fascinated by them and snuck a pair off to my room and tried them on. I just remember what a thrilling experience it was. I had never felt anything close to the feel of that beige nylon on my skin, and knowing that I was doing something I shouldn't have been doing was also a rush.

    After that I was obsessed with exploring more. I wanted to try on panties, skirts, bras, high heels, the works. Unfortunately by this point in time there was a noticeable size difference between me and my mom, and with no sisters I was mostly limited to sneaking away her pantyhose and panties. One time I had a chance to check out the shoes in her closet but they were way too small.

    I didn't get to dress much in my teens or college years, but once I was on my own and had my own place I really got into dressing a lot more. The last phase for me wasn't until my early/mid 20s when I finally started buying wigs and makeup. That really launched my dressing up to the next level.

  6. #6
    Female Illusionist! docrobbysherry's Avatar
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    Sep 2007
    Orange County, Calif.
    A tenant moved out and left a box of her old clothes!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  7. #7
    Miss Conception Karren Hutton's Avatar
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    Aug 2005
    South Western PA
    I was 7.... mom had always said I was supposed to have been a girl. She always wanted to make me girly dresses for Halloween. And I never took her up. But when my sister was born I became obsessed with sneaking into moms closet and trying on her bras and girdles and stocking and nighties. That was over 6 decades ago and I am still obsessing and have the breasts to prove it! Lol.
    Last edited by Karren Hutton; 03-14-2021 at 02:28 PM.

  8. #8
    Aspiring Member MonicaPVD's Avatar
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    Jul 2018
    New England
    Around first or second grade I started borrowing mom's hose. It was all downhill from there. Fully dressed for the first time around age 15, went out in public for the first time around 16, dressed a lot during college, then became a boring hetero guy for a very very long time. Too long.

  9. #9
    Girl Power! CrossKimmy's Avatar
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    Jun 2006
    San Diego
    I was probably 7 or 8 years old when I got into my mother?s wardrobe. I was alone for like 3 seconds and saw her pink and neon green tulle skirts and was quite taken with them so I put them on and played ballerina. Then I decided to keep them in my wardrobe but they were quick to find them and I was told that this was not acceptable. But they probably thought it was a phase. Well look how well that turned out for them lol

  10. #10
    Silver Member
    Join Date
    May 2016
    Northern New England
    I was about 11 or 12 years old. My mother ran a pretty tight ship at home so the only thing around the house that might satisfy a young boys curiosity about girls were the lingerie sections of the Sears and JC Penney catalogs. Over time I realized I was just as fascinated with what the models were wearing as I was with the models themselves and I found myself wishing I was one of them. It just took of from there.

  11. #11
    Silver Member Pumped's Avatar
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    Aug 2013
    I was very young, maybe 5-6 years old. This was early 60's, living on a farm miles from the city so I couldn't just go buy stuff. I started messing around with my moms bras even though they were huge on me. I would stuff them with t-shirts and pull another t-shirt. I cut up up a t-shirt to make a skirt. I had an older sister, but she didn't have much girlie stuff. It was pretty much a disaster, but it was all I could come up with. Even then I was into big boobs!

    Later on in my early teens my parents got divorced, lived with my dad and I was able to collect a few items. Then dating and marriage and I took a 30-some year break even thought I still thought about dressing. My wife is tiny so her clothing wouldn't fit and nowhere to hide anything away living in a tiny apartment.
    Last edited by Pumped; 03-14-2021 at 09:53 PM.

  12. #12
    Aspiring Member kellyanne's Avatar
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    Dec 2007
    At a very young age , bras, panties & the appearance of lingerie clad women in catalogs were very appealing.
    Years before puberty, wearing my mother's bathing suit made me feel free, whole and truly myself, I had went to the dryer , opened it and felt I had to wear it to be me.
    In grade school, the sound of the walking teacher's pantyhose on her girdle was beautiful to my ears.

    In retrospect, the onset of puberty seemed to put the dressing aspect in dormancy but the love of lace continued.

    I couldn't dress in full until I lived on my own in the last year of college.
    Before the last year , leaving town for summer work forced a toss my ladies clothing for lack of storage.
    Since then I have lived on my own and dressed at will.

    It took some time to do it well, size properly, match colors well and put on make up better.
    A wig website helped pick the better wig style and I have pretty well stuck to it.

    The 2 things I wished I had done earlier is buy breast forms& Transform bras and a shaper girdle.

    Make up is easy once you get the hang of it.
    A really nice lady gave me 2 tips always remembered:
    - less is more
    - blending ( with the fingers) is the secret to a great natural look.

    I enjoy seeping in my bra, forms, panties and nightie every night and it gives the same sense of freedom to face to day as such.

    At 60, coming up 50 + years dressing, almost 40 + years dressing in full with wigs, make up, heels etc.

    We can only be what we are.

  13. #13
    Silver Member Marcia Blue's Avatar
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    Apr 2009
    Western Iowa
    I was 5 years old. Mom and Dad had gone over to the neighbors for a visit. I was attracted to Moms lipstick samples. Mom sold Avon so there were lots of choices. I tried on several colors that day. I was hooked. That same year I started trying clothes along with the lipstick. By the time I was 8, I was also into mascara. I never ever really stopped dressing.

    Mom caught me once in High School. Dressed to the nines, in her clothes. She never said anything to me about it. I learned to be even more careful. Once when Mom, Dad, and my sibs were going out of town, after she caught me. Mom pulled ma aside and said to behave while they were gone. She also told be to stay inside if I, was not "properly" clothed. I stayed home except to go work. My hair was bra strap length then. I wet set my hair, and spent most of the week dressed. To this day I wish I would have at least gone out for a drive all dressed up.
    Marcia (LOVES) Blue

  14. #14
    Member Bluesman's Avatar
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    Jan 2009
    Los Angeles
    I was 15, playing one of the kid roles in a professional production of Macbeth. Dressing room space was limited, so couple of the gay men and me (go figure!) shared space with the female cast with just a clothes rack separating us. One night when I was alone in the dressing area, I noticed a pair of panties on a chair. I pocketed them, took them home, put them on and masturbated. Around that same time I discovered a trunk in the attic with a couple of nightgowns in it and started wearing one to bed. Over the next years I found or purloined panties until I got up the nerve to buy my own along with a matching bra in my early twenties. Dressing was limited to those kind of lingerie items, off and on, periodic purges, reading cross-dressing letters and stories in Penthouse Variations (how many remember that publication?) til my mid-30's when I bought by first dress, which was later purged. Things continued that way more or less for the next 20 or so years, hiding it for the most part from my wife. In my late fifties decided the only thing "wrong" with CDing was hiding it from her, so put it more out in the open. Didn't go well initially, went back into hiding although the secret was out of course. Eventually started purchasing dresses, skirts, blouses, shoes, etc. wearing them in private, and occasionally being caught if my wife came home unexpectedly. It's all out in the open now although not always comfortably so. I mostly dress when she's out and I change before she gets home (she usually texts me she's on her way). Sometimes she forgets to text and I'm still dressed; it's a little awkward but not distressing. Occasionally I will dress when she's around, especially during the lock-down period when we were pretty much home-bound all day. So that's the journey that all started with a horny teenager and a pair of purloined panties.
    Last edited by Bluesman; 03-14-2021 at 08:59 PM.

  15. #15
    Silver Member Sometimes Steffi's Avatar
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    Sep 2008
    Nation's Capital
    I was about 12 when I stepped into my mom's panties one leg at a time. I didn't realize that there was any other way to do it.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

  16. #16
    Aspiring Member ShelbyDawn's Avatar
    Join Date
    Mar 2013
    Austin, TX
    Five or six, fell in love with how soft my moms slips were, started wearing them when no one was around. Quickly gravitated to stealing/borrowing panties from my sisters, and then on to bigger and better things as I got older.
    I am Me and Me is OK!


  17. #17
    Junior Member AndieB's Avatar
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    Feb 2021
    Western VA
    Age 3 or 4 I was caught wearing one of my mom's nighties. My dad said to my mom, "looks like we caught a princess." I'm fairly confident that is one of the earliest memories in my life and I've been dressing up to some degree ever since. I didn't really get into makeup until my later 20's though.

  18. #18
    Member Jeanettew's Avatar
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    Mar 2015
    I was a late bloomer a few years ago when I was about 35 the football club I go to was holding a Miss Club contest, and as a laugh some of the guys said we should try and railroad it and one of us should enter, my wife overheard and said she would help, the day arrived and so in my man undies she gave me some of her old tights found one of her lose fitting dress's and old Bra and some balloons she filled with rice for boobs, some make up and one of her sisters wigs, shoes were hard but she found some at an op shop that fitted, off I went and it was a fun night.

    Laying in bed that night all I could think about was how nice the tights felt against my legs and the dress was something else to wear and I wanted to try more, it was a few weeks later when she went out for the night with the girls and I spent the whole evening trying on her cloths, I was hooked, but I needed my own so I started to build my own closet, Stocking Undies dress's, skirts and heels, I just live for the feel of stocking and heels. that was thirty years ago

  19. #19
    Banned Read only Cass42's Avatar
    Join Date
    Mar 2021
    Age 7,was at an aunt's house and she had this dark navy dress on the floor.Mom and I were over to visit.They discovered I was gone and the bathroom door was closed.Was in the bathroom putting the dress on.I walked out with it on.Both saw there was something about me,I was not the typical boy into boys loved to do.Saw I loved wearing this dress.

  20. #20
    Aspiring Member SaraLin's Avatar
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    Jun 2017
    Central Fla.
    I've always felt like I "should have been a girl", but also knew from a very early age that this wasn't "normal". Needless to say, it caused a lot of turmoil until MUCH LATER I learned to start accepting myself.

    But putting that aside - the first things I remember doing were (not sure of the order)

    Spending the night at grandparents house. They didn't have PJ's for me, so GM used one of her house dresses, with a belt to tuck up the excess length. I was in heaven!

    Cub scouts - in a skit, got cast as the princess - string mop head for hair, and a paper heart pinned to my chest - that I gave to the prince who rescued me - from what I don't remember.

    "borrowing" my sister's clothes and wearing them in bed, under the covers - until mom found them, and I had to scramble for a good lie.

    Finding boxes of feminine clothes in my grandparents' attic that I could wear. I "liberated" some of these and hid them in an abandoned house in the woods, where I could go and be a girl.

    One halloween, and too poor to afford costumes, mom let me put on a dress -and yes, another mop head for hair. A neighbor lady loved it and said I was "the cat's meow"

    It would be easy to claim that these things LED me to my feelings, but in fact, I feel it was my inner feelings that led to most of the events.
    For example, I would make up excuses to stay the night at my grandparents' house, knowing I'd get to "be a girl" for a little while.
    About the only one that I can't say was a result of my inner she-ness, is the scouting skit. and maybe even there, they sensed that I was the right one for the part???

  21. #21
    Platinum Member Beverley Sims's Avatar
    Join Date
    Nov 2011
    Lowestoft UK. Beverley was here.
    I was dressed by the next door neighbours girls we playedmothers and fathers and I was the baby.

    Later they dressed me up in their clothes and went for drives in the country with their parents.
    Work on your elegance,
    and beauty will follow.

  22. #22
    Exploring NEPA now Cheryl T's Avatar
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    Feb 2006
    At about 5 or 6 I suddenly had the urge to wear mom's panties.
    Of course at that time they were nylon and so silky and smooth. They just felt wonderful. Next I wore a slip for the same reason, but noticed the "pockets" up top and stuffed them, but everything fell out so eventually came a bra and sock stuffing under the slip. From there it was her OBG with garters and then stockings and her heels. The rest is history.
    I don't wear women's clothes, I wear MY clothes !

  23. #23
    Junior Member Deborah G's Avatar
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    Jul 2006
    Just East of Houston, TX
    Started with my sister's clothes, i.e. panties, high heels and Keds shoes. She and I were about the same size. Then I tried on her hose with garters, dresses, bras, skirts. The feelings I have wearing these things cannot be described! Some things just feel right!

  24. #24
    New Member
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    Feb 2021
    Liked your one

  25. #25
    Claire M Claire M's Avatar
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    Jan 2014
    The first I consciously crossdressed I was 13. I had a major urge to see what it felt like to slip into a pair of my older sister's panties (white cotton with little blue roses still remember every minute detail 50+ years later). A few weeks later I HAD to see how one of her bras felt. And within another couple weeks I was fully dressed in one of her skirts a sweater and heels ... just to see how it felt. Needless to say it was wonderful .. confusing ... scary ... me (usually followed by a bit of guilt and shame be a useful after all boys shouldn't do things like that.)

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