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I Remember My First Crossdressing Experience

Personal Stories, Advice, and Support 2,925 People

    At Comic Con

    it was a month before a comic con i was going to with my friend alice "so what are you going as for the con" she asked "i dont know i dont really have any money right now for a costume" "well i do have some old costumes from other cons" "oh no im not going as a girl" "dont...
    sissyslut64 sissyslut64 18-21, M 5 Responses Oct 2, 2013

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    My first real crossdressing experience was just

    a few weeks ago. My gf wanted to see me get all dolled up for her so I went out. Bought a beautiful black half sleeve dress tan stockings, black high heels. Already had a corset, wig and panties at home. After getting home I put all of this on and did my makeup to the best of...
    sandrasweetie sandrasweetie 26-30, T 14 Responses Dec 31, 2013

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    Oh How Exciting It Was

    I had my first cross dressing experience when I was 11 yrs. old. I went into my Mother's room when everyone was out of the house, and got her black Haynes hose out of the drawer. I put them on and promptly **********. I though it was great. As I matured, I always liked the way...
    chancery1 chancery1 61-65, M Oct 24, 2013

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    Wow, A Day To Remember

    Do you remember that first time you put your first high heels on, and how it made you feel? I will never forget that first time going out as a young girl. Like most of us I played around with my mom's shoes and clothes, nothing really serious, just having fun, until my 14th...
    MiriamK MiriamK 56-60, T 7 Responses May 3, 2012

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    I was with my friend

    and we dressed as guys and walked around outside.
    soonkyu soonkyu 16-17, F 4 Responses Feb 24

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    Grdlgrl's First Time

    Much like many of you I started perusing the Sears, JCPenney, and Montgomery Ward catalogs. When you're just coming into puberty its a big deal to see women in their underwear. Eventually I started to wonder what it would feel like to wear one of these things . So I went to my...
    grdlgrl grdlgrl 61-65, M 12 Responses Apr 8, 2012

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    Dressing Up For The First Time

    I was always interested in women's clothing. I don't know what it was but it just made me wonder what it was like to be a girl. When i was 15 i finally gave into my curiosity and wanted to browse my sisters clothes. I went into my sisters room when the house was empty and opened...
    badassgirl123 badassgirl123 18-21, M 17 Responses Oct 10, 2012

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    My Mothers Dresses And Nighties

    When I was about seven years old I remember admiring how pretty my mother looked in her dresses and especially her nighties. I began to look forward to seeing them in the laundry basket. When I was sure that I would not be disturbed I used to try them on for a few minutes and...
    ChrisBloom ChrisBloom 31-35 4 Responses Jul 14, 2013

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    This Is How It Started...

    I was about 7 or 8 and had never had any interest in girls clothes or anything at all like that. One night i was staying the night in an aunts house. i slept in the spare room and the next morning i woke up very early and could not go back to sleep. So in boredom my eyes began to...
    crossdresser12345 crossdresser12345 18-21, T 12 Responses Jun 9, 2013

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    fercrox fercrox 46-50, M Apr 6

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    Quiet Mountaintown

    I had dressed at home but never left my house before. But a few summers ago I was online chatting with a guy on and off and one conversation led to turn-ons. He confessed that crossdressers turned him on. Well we had never met but I thought "what the hell - I'm game" I told him I...
    Cyndie1 Cyndie1 46-50, T 5 Responses Oct 17, 2013

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    The Party

    My first time crossdressing came when I was 13. I lived with my mother and her girl friend. My mothers office was having a halloween party costum ball. I was now to old to go trick or treating so they asked if I wanted to go. My mothers friend came up with the idea of going as a...
    RobinLeade RobinLeade 22-25 21 Responses Aug 19, 2011

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    My Early Crossdressing Fantasies If you recall,

    I was forcibly crossdressed and humiliated by three adult females, and in front of four young girl cousins. My earliest memories of wanting to be a girl were in kindergarten. Girls still wore dresses to school, and I wanted to wear a dress. To me then, a dress symbolized being...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Mar 2

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    First Time, Caught By Mom

    My mom knew I crossdressed, or suspected it anyway. I had been hiding old dresses of my sisters in my closet for a couple of years. Mom never asked me about them, thinking it was a phase. I'm not sure she thought I was trying them on or what, she never did tell me. When I was...
    marybethme marybethme 51-55, T 7 Responses Jan 18, 2013

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    Yeah. I had to go outside in the cold I grab

    some logs and I put my moms sweater in real quick. And that's pretty much that.
    Gus1996 Gus1996 16-17, M Jan 27

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    To Tell The Truth

    So, we are all just sweet ladylike men, who bask in the glow of our frocks and finery, eh? NOT! I do not know about anyone else, but, for me, it was SEXUAL, pure, and simple. The first time I put on my wife's black half slip that was hanging from a hook on the bedroom door, I...
    joseygurl23 joseygurl23 56-60 8 Responses Sep 15, 2013

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    I was tired, lonely and needed to relax.

    I went to the local adult video store and picked up a video. In it, there was a woman who was really cute who wore a white corset, and a pair of pink kitten heel pumps. I got so excited because everything was from her point of view, and she was totally in charge of what happened...
    wistfulmiles wistfulmiles 51-55, M 5 Responses Mar 23

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    Ice Skating Heaven

    My first time dressing myself up came when i was around age 12. My sister used to ice sKate but had recently quit, and all her ice skating dresses were in a bag in the corner of my moms office. Everyone in my house was gone and the yellow leotard on the top of the pile caught my...
    jessie3363 jessie3363 18-21, M 9 Responses Mar 28, 2012

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    Forced To Crossdress

    Every now and then in my childhood, I would slip into my friends house while they were gone, and try on his moms girdles, panties, leotards, etc. Then one day, I was dressing in my favorite girdle, when my friends mom came in the room. I had missed hearing her come in, and we...
    crossdresslover1 crossdresslover1 31-35, F 20 Responses Aug 7, 2011

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    mrman77 mrman77 22-25, M 1 Response Mar 5

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    My Halloween As A 9 Year Old Was More Embarrassing Than Fun.

    I was 9 and it was not long after my sister first introduced me to dressing up. My mother, a growing supporter of my budding feminine relationship with my sister, told us she just bought us matching devil costumes. I suppose they were very cute but I was not expecting our recent...
    kayleew2000 kayleew2000 18-21 15 Responses Mar 28, 2012

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    Two Weeks At My Aun't's House, Living As Mary Beth

    I don't know where else to share this but here. It's about spending two weeks at my Aunt's house in Cleveland, as a 14 year old girl. It was my mother's idea, with the intent of having me get my cross dressing into the open, which as I've thought about it, was a smart move...
    marybethme marybethme 51-55, T 5 Responses Jan 20, 2013

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    This was my first out of the house experience.

    I think I was around 12. It was really late and I left the house to walk around. I was in one of my sisters pink dresses and had this stupid flowery hat. The hat really didn't fit my head but I didn't have access to a wig and my hair was short. No makeup, no nothing. I got...
    julieann3 julieann3 51-55 7 Responses Jan 17

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    I joined a pageant where guys should wear

    girl's clothes and girls wear guy's clothes. I wore a tuxedo. It was my turn onstage and when I got there, people screamed for my name. For the first time in my life, I felt like human. I felt so beautiful and handsome and cool. And yeah, I won!! :) Don't get me wrong, I'm not...
    MylifeasMae MylifeasMae 18-21, F 9 Responses Apr 12

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    Comfy With Myself

    I started when I was very young also, and then for many years I completely hid my fetish. Now I am comfy with it and express it anytime I can, thanks to a loving and accepting wife =) My first times I thought something was wrong with me, maybe that I was gay (a bad word in my...
    SecksKitten SecksKitten 31-35, T 9 Responses Aug 1, 2012

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    When I was about 10, I would try on my moms

    clothes. I loved seeing how they fit me, feeling girly. Loved her skirts, I would wear them high like it was a micro mini skirt. I specially loved her thongs and bras. It made me feel like a girl, and gave me my first cravings for sex with men.
    islutmyself54 islutmyself54 26-30, M 3 Responses a week ago

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    One of my first times I was around 16 I tried

    on one of my sister's miniskirts and then I was hooked. And of course I was always attracted to girls in knee socks, so I had to try a pair on for myself. the rest is history.
    schoolgyrlKaren schoolgyrlKaren 41-45 4 Responses Apr 12

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    Well, i lost a bet so I had to make a fake

    Facebook profile of me but as a boy with photos. Sooo I tried to pass off as a boy buuuttttt didn't work too well I had to use sooo much duct tape on my breasts xD
    JordanJessie JordanJessie 18-21, F 3 Responses Feb 28

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    I clearly remember my first experience

    crossdressing-I was six years old and I was playing with a doll. I don't know why since I wasn't effeminate as a boy. My cousin tried to take it away and I hit her. My mother was so mad that she dragged me into the house, ******** me, spanked me in front of the girls, forcibly...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Feb 28

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    Yesterday I cried yesterday,

    not a hard satisfying cry, but small sobs, the kind that struggle to come out against your will. I didn’t think that I would cry, it caught me by surprise, but not as much as the violent shaking that shook my body as I talked. I even wrapped my feet around the chair legs, and...
    1SarahAnn 1SarahAnn 46-50, M 2 Responses Mar 2

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    Do I Remenber?

    I remember it like I acutually gave a damn. I saw my sisters clothes lying on her bed and next thing I know i was trying it on. I ended up devolping a good/bad? Habit pf wearing everything from bras, leggins, hell even panties.
    CozzyRosie86 CozzyRosie86 18-21, M Oct 8, 2013

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    Shopping With Friend

    I had been curious about cross dressing since middle school but I was always to embarrassed to try and do it. In college, I told my lesbian friend that I was a cross dresser who, well, hasn't cross dressed yet. So one day she took me to the local mall and had me try on various...
    shadow950 shadow950 18-21, M 3 Responses Oct 11, 2013

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    I was about 12 when I randomly got the urge to

    go into my sisters room who was 11 going on 12 and try on her clothes for reasons I didnt understand at that time I found a pair of cute pink bikini panties and matching training bra I put them on along with a jean skirt my sisters friend left over with a black spaghetti strap...
    liljess93 liljess93 18-21 11 Responses Feb 27

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    My first cross dressing was

    when I was a teenager and I wore my mums panties. She had some really sexy ones that were all frilly and Lacey. As I wore them they rubbed against my shaven balls which was such a turn on and felt fantastic When she was out I would wear them and her silky nightie and...
    skid59 skid59 51-55, M 4 Responses Dec 27, 2013

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    First Time In Lingerie!

    Hi everyone. My first time happened when I was about 9 or 10. I had my first wet dream and then started to ********** regularly like any normal boy. I remember finding a pink slip in the laundry and immediately needed to wrap it around my ****. That sensation was so thrilling...
    cdpattyny cdpattyny 46-50 5 Responses May 31, 2013

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    mrman77 mrman77 22-25, M 1 Response Mar 3

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    Being Dressed In Sisters Clothing

    When I was 7 years old whenever my mom went out, my sister would dress me up in her clothing including a bra and even put make up on me. She would do it like once a month for almost a year and once again when I was 12. After a few years I started dressing myself up in my friends...
    ArejayakaRegina ArejayakaRegina 22-25 2 Responses Oct 24, 2013

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    So Soft

    this is the first time i have ever told this story as a child my mother had a picture of me dressed up in her dress and nylons she used to tease me about being her little girl .i rememeber this stuck with me till i was about 10or 11when i would be at home alone and started...
    jwatters jwatters 46-50, M 6 Responses Feb 18, 2013

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    My older cousin cousin,

    (a girl) Madie, was babysitting me. As I was only 7 or 8 at the time. She was doing her makeup and I asked can I try some? She then did my "make up" and put a wig on me. Then proceeded to give me a pair of panties, short shorts, and a PINK shirt. I remember this as being a...
    Teege07 Teege07 18-21, M 4 Responses Apr 10

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    My high school years were very typical

    for a young man, cars, football games, parties, and girls. Not a lot of girls, but enough to know I liked them for more than just the clothes that they could wear. I was involved in sports, and began to weight lift and gain muscle. I wasn’t a big guy, but not too many people...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Mar 2

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    I was the only boy growing up with five sisters.

    I was second to the youngest with typically not more than a year in between each other’s birthdays. I'm sure I was dressed up very young in hand-me-downs and teased by my sisters. There was always girl clothes around and a rag drawer where old clothes went some of which...
    abr549 abr549 41-45, M 8 Responses Dec 3, 2013

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    Tabitha Found Me

    It all started , when i was very young i can remember being in a large store and wanting to touch the dresses and lingerie they somehow always attracted me . The silky touch was so nice , Some years passed i was maybe 6 or 7 . My mom gave me some clothes to take upstairs ,among...
    tabithastephens tabithastephens 31-35 16 Responses Aug 26, 2012

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    Crossdressing Awakening

    The first time that I recall having an interest in crossdressing was when I was about 10 years old. It was Halloween time and there was a costume parade at school. For the life of me, I cannot recall what I wore, but there is one costume that I vividly remember! There was this...
    jennyla73 jennyla73 36-40, F 12 Responses Mar 25, 2012

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    First Time In Public

    My mom, who had an advance degree in social work, was "cautiously supportive" when she first caught me cross dressing. She wanted me to wear a dress around the house as often as possible. The thinking seemed to be, get it out in the open and either I'll get tired of it, or...
    marybethme marybethme 51-55, T 5 Responses Jan 20, 2013

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    The First Time.

    This is an account of the first time I went outside dressed in women’s clothes. I was in my early 20’s and believe it or not, married. My wife was slim and into short skirts and long boots, so there was an abundance of sluttish clothes around. Anyway it was one evening...
    FAIRLANE1 FAIRLANE1 41-45 8 Responses Jan 18, 2013

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    I was 8 or 9, the youngest in a largish family

    of 5 kids - 4 girls ... and me. My sisters always seemed to have friends over to the house and one of their favorite activities it seemed, was playing oh-so-glamorous dress-up. I so clearly remember being envious of all that fun. I remember the day when one of the friends...
    sissyJanine sissyJanine 31-35, T 4 Responses Feb 27

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    My first crossdressing experience was with my

    Mum's knickers. I remember I wanted to recreate a scene from a film where I saw a beautiful woman walking around in just her underwear, it just made me want to feel how she felt with soft fabric rubbing against her. I put the blue soft knickers and felt a rush I had never felt...
    LucyTG LucyTG 26-30, T 4 Responses Mar 19

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    My First Step Down A Long Road

    My first time I was 8 and home alone. My brothers were out on dates. My parents went to the weekly grocery run. I was watching a war movie so my dad said to stay home enjoy the movie. Well the movie ended about 30 minutes later and a movie started with Grete Garbo she put on...
    francescavera francescavera 56-60, T 10 Responses May 23, 2012

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    My first couple times crossdressing were with

    my sister's panties. I, through a series of events with the washer being broke, ran out of underwear. My mom had to go and get my sister's underwear and make me wear it, I tried not to. At that time I felt "meh" about it. Later on, about a year, I got curious and remembered how...
    tiffanyjoxd1989 tiffanyjoxd1989 22-25, T 4 Responses Mar 7

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    First Time Being A Girl

    My parents went out on a 2 week vacation during the summer. I went to my grandma's house when my cousin, one year younger than me stayed during the summer. It was me, my grandma, and my cousin for two weeks. My grandma and my cousin are both really girly, really into make up and...
    JasmynLaura JasmynLaura 18-21, F 8 Responses Aug 13, 2012

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    Still A Thrill! (And Still Trim And Thin!)

    This is a workday for me (Financial services), and I have my own office and bathroom, so I can get out of the house and "femme out" on weekends!Today I started with a turqoise brief by vanity fair (But hipsters are a must with slacks to avoid "panty peek!"), a black Career...
    BuffyOh BuffyOh 66-70, M 1 Response Sep 29, 2013

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    Best Step Sister Ever ;)

    I was at home when everyone left to go to my Lil brothers game. So I got dressed in black panties, black bra, a tank top and short shorts. I went and laid in my bed and started watching a movie when I seen my step sister come up the steps with a bag, and my bedroom door was wide...
    loverboy758 loverboy758 18-21, M 4 Responses Oct 12, 2012

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    My First Time I Crossed Dressed

    The first time I crossed dressed I was 14 and it was for a costume party at church. There were 5 of us kids and money was tight. My mom said I would be going as a girl. First she had me put on a pair of her panties then one of her bras and stuffed it with kleenexes. I remember...
    Adam59 Adam59 56-60, M 11 Responses Feb 12, 2012

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    Started Young

    When I was about 7 or so, I tried on my mom's panties and then pantyhose. They were too big, but felt incredible, silky, soft, smooth. I do not know what made me do it, but once I tried, I was hooked, So, I have been crossdressing almost 30 years. I tried my sister's panties and...
    samctv10 samctv10 36-40, M 40 Responses Feb 5, 2012

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    My First Panties

    I remember my first panties when I was 12. My hands were shaking with mixed nervous and excitement as I pulled it out from its plastic wrapper. It was a cotton pink panties with lace edgings on the waistband and leg holes. My mom told me to wear it and it was so cool. That...
    sharinep sharinep 22-25, T 10 Responses Jul 2, 2013

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    Related Experiences

    This is not my first but it's the only one I feel comfortable sharing. I was 13 at the time and I knew more about the adult world than I was supposed. I was a crazy kid trying to...
    ttremain ttremain 18-21, M Apr 9

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    It was on my birthday this year (12th April 2014). I had my best friend over and also my boyfriend. I was feeling quite tired, so I put a movie on for my boyfriend and bestie to...