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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...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Mar 2

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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...
    sissyJanine sissyJanine 31-35, T 4 Responses Feb 27

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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...
    FAIRLANE1 FAIRLANE1 41-45 8 Responses Jan 18, 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...
    jwatters jwatters 46-50, M 5 Responses Feb 18, 2013

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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...
    abr549 abr549 41-45, M 8 Responses Dec 3, 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...
    MiriamK MiriamK 56-60, T 7 Responses May 3, 2012

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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...
    SecksKitten SecksKitten 31-35, T 9 Responses Aug 1, 2012

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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...
    skid59 skid59 51-55, M 4 Responses Dec 27, 2013

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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...
    crossdresslover1 crossdresslover1 31-35, F 20 Responses Aug 7, 2011

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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...
    grdlgrl grdlgrl 61-65, M 12 Responses Apr 8, 2012

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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...
    jessie3363 jessie3363 18-21, M 9 Responses Mar 28, 2012

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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...
    LucyTG LucyTG 26-30, T 4 Responses Mar 19

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    Look at mycrox-d.com Lingerie for crossdresser
    fercrox fercrox 46-50, M Apr 6

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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...
    crossdresser12345 crossdresser12345 18-21, T 12 Responses Jun 9, 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...
    RobinLeade RobinLeade 22-25 21 Responses Aug 19, 2011

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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...
    islutmyself54 islutmyself54 26-30, M 2 Responses 1 day ago

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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...
    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...
    shadow950 shadow950 18-21, M 3 Responses Oct 11, 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...
    chancery1 chancery1 61-65, M Oct 24, 2013

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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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    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...
    schoolgyrlKaren schoolgyrlKaren 41-45 2 Responses 5 days ago

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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...
    loverboy758 loverboy758 18-21, M 5 Responses Oct 12, 2012

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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...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Mar 2

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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...
    Teege07 Teege07 18-21, M 4 Responses a week ago

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    My First Time In Daylight. - Since my wife left I had been dressing up and going out while it was dark, but I had never gone out during the day, this was about to change. I had a...
    FAIRLANE1 FAIRLANE1 41-45 2 Responses Jan 25, 2013

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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...
    Cyndie1 Cyndie1 46-50, T 5 Responses Oct 17, 2013

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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...
    1SarahAnn 1SarahAnn 46-50, M 2 Responses Mar 2

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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...
    sandrasweetie sandrasweetie 26-30, T 14 Responses Dec 31, 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...
    wistfulmiles wistfulmiles 51-55, M 5 Responses Mar 23

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    Uploaded more pics go check them out!
    mrman77 mrman77 22-25, M 1 Response Mar 5

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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...
    ArejayakaRegina ArejayakaRegina 22-25 2 Responses Oct 24, 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...
    tabithastephens tabithastephens 31-35 15 Responses Aug 26, 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...
    marybethme marybethme 51-55, T 5 Responses Jan 20, 2013

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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...
    Adam59 Adam59 56-60, M 11 Responses Feb 12, 2012

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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...
    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...
    tiffanyjoxd1989 tiffanyjoxd1989 22-25, T 4 Responses Mar 7

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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...
    julieann3 julieann3 51-55 7 Responses Jan 17

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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...
    kayleew2000 kayleew2000 18-21 15 Responses Mar 28, 2012

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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...
    MylifeasMae MylifeasMae 18-21, F 9 Responses 5 days ago

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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...
    marybethme marybethme 51-55, T 5 Responses Jan 20, 2013

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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...
    BuffyOh BuffyOh 66-70, M 1 Response Sep 29, 2013

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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...
    JasmynLaura JasmynLaura 18-21, F 8 Responses Aug 13, 2012

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    Just uploaded a couple of pics check them out!
    mrman77 mrman77 22-25, M 1 Response Mar 3

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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...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Feb 28

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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...
    joseygurl23 joseygurl23 56-60 7 Responses Sep 15, 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...
    cdpattyny cdpattyny 46-50 5 Responses May 31, 2013

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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...
    sharinep sharinep 22-25, T 10 Responses Jul 2, 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...
    liljess93 liljess93 18-21 11 Responses Feb 27

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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...
    badassgirl123 badassgirl123 18-21, M 17 Responses Oct 10, 2012

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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...
    JordanJessie JordanJessie 18-21, F 3 Responses Feb 28

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