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I Remember My First Crossdressing Experience

Personal Stories, Advice, and Support 2,888 People

    I started ************ at 12,

    sat on the bathroom floor going at it. I saw a pair of my mothers panties on the floor and the look of them turned me on. I picked them up, they felt so good in my hand and I rubbed them on myself as I played. It felt amazing. I did this for a few months when ever I had some 'me...
    tanyachambers tanyachambers 41-45 10 Responses Jun 10

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    This is my tenth year of living

    as Heather. I still remember when my older step sister Janet adopted me when my parents died in a car accident and agreed that I was to become heather. When Janet arrived I was with one of my older step sisters Linda and both dressed me in a pink laced up corset, pink panties...
    SexyHeather88 SexyHeather88 26-30, F 4 Responses Jul 13

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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 14 Responses Mar 28, 2012

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    I was 8-9 and we had just moved to a new home.

    As often happens, things were disorganized for a while and one day after school I cam across a plastic bag full of lingerie that had been my mothers (obviously when she was younger and skinnier). I opened the bag to find real silk stockings, garter belts, a negligee and my...
    tvCorinne tvCorinne 51-55, T 25 Responses Jun 3

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    It was the summer of 77

    and I was 10 years old when it happened. It started out as dare from my friends sister who was twelve and we were sitting in their back yard the first day of our summer vacation when she says I dare you boys (me and her two brothers both 10 also) to wear my clothes all day...
    greenmonkey17 greenmonkey17 46-50, M May 24

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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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    First time I completely dressed,

    I was on a business trip and had bought a wig, makeup, a bra, panties, waist cinch, stockings, petticoat, and a french maid outfit. After getting dressed, I took some pictures of myself. I then went online in a crossdressers room. Wasn't long before a Dom, sent me a private...
    deleted deleted 26-30 10 Responses May 2

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    So all my life I always knew there was

    something different about the feelings inside compared to my little brother only two years younger. Things I thought where funny him not so much girly things like barbies n playing dress up seemed interesting to me even tho I wasn't participating for fear of being called gay by...
    Natalitx Natalitx 31-35, T 1 Response Mar 20

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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 3 Responses Apr 12

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    I have tried to post part 6 of my story many

    many times but EP will not allow it. So I will put it in the comments below and see if that works.
    jamie50 jamie50 51-55 2 Responses Oct 11

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    Dressing Up for the First Time (part 2)

    After the first time i crossdressed in my sisters clothes, i just had to do it again. It was a week until i had the house to myself for a couple hours. Right when my family left i went to my sisters room and picked out some clothes different then the ones i wore last time. I...
    badassgirl123 badassgirl123 18-21, M 11 Responses Oct 11, 2012

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    Sneaking Into My Sister's Room

    I was twelve, she was sixteen. She was away with my mom for the weekend. I had been really curious about crossdressing for a while, so I took the plunge and went into her room. I remember fishing through her bikini drawer and her panty drawer looking for fun stuff. Eventually...
    LaurenJcd LaurenJcd 18-21, T 17 Responses Jun 14, 2012

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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 14 Responses Apr 8, 2012

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    Dressing Up For The First Time Pt3

    Dressing in my sisters clothes became a regular thing after about 2 months of doing it, I would use her vibrator on my *** at least once a week. My family was gone more often so it gave me plenty of time to prefect doing my make up, hair and shaving my legs. One night when my...
    badassgirl123 badassgirl123 18-21, M 13 Responses Oct 22, 2012

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    Feminized To Her Will

     The new boy in the office is soon whipped into feminine shape She knew as soon as she saw him that it would be no contest. As office manager she knew a thing or two about how to have her way and one look at the way he came swaggering in on his first day and she decided he was...
    sammi11 sammi11 41-45, T 33 Responses Aug 4, 2011

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    I was 16, my sister had moved out

    and she had left a huge bag full of her old clothes. I got very curious about it and decided that one day I'd look inside. I found lingerie and stockings, suspender belts and bras. I got really turned on. I wanted to be in them, so I planned to fake a day off school so I knew...
    irishfella82 irishfella82 31-35, M 5 Responses Apr 29

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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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    My first experience of crossdressing was

    when I stole a pair of knickers from my mums underwear drawer. I remember seeing a woman walking round in her knickers on the tv and wanted to see how that felt. I will always remember the rush that first time I pulled them up my legs and the amazing feeling I had :) It all felt...
    LisaTG LisaTG 26-30, T 7 Responses Jun 1

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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 19 Responses Oct 10, 2012

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    Part III mid-teens There was one girlfriend

    that I had forgotten about before I met Marie. At 15 a new girl had moved into our neighborhood and she ended up becoming my first real girlfriend. I wasn't attracted to her because of the way she dressed. She was a cute friendly girl but they were not well off financially being...
    jamie50 jamie50 51-55 1 Response May 18

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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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    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 5 Responses Oct 12, 2012

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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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    Dressed By Girlfriend And Her Friends

    It was a normal summer day. I was just hanging out with my girlfriend at her house. Both her parents were away at work Several of her friends were there too. I was 16 and they were a couple years younger. I was a jock back then. Although I had tried on a few girlie items in...
    bethanngirl bethanngirl 56-60, M 12 Responses Jun 9, 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 31-35, T 13 Responses Dec 31, 2013

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    When I was seven years old,

    my sister was the flower girl at a wedding for one of my mom's friends. her dress was perfectly white, with a pink ribbon that tied in a huge bow on the back, but since she was such a tomboy she hid it in my closet so she never had to look at it. I thought it was beautiful, and...
    faellorien faellorien 26-30, M 9 Responses May 21

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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 Time Dressed

    My first time crossdressing was the most exciting sexual experience of my life. It still makes me hard remembering it. I had dreamed of dressing since seeing my sister act as a fairy in a school play. She was dressed in a pretty pink dress, and I so wanted to wear something as...
    Mandisissy Mandisissy 31-35, F 3 Responses Sep 8, 2013

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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 8 Responses Apr 12

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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 14 Responses Feb 12, 2012

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    It was inspired by the show Jackass

    and by WWF. If i remember correctly it was New Year's eve of 2000 and i had just taken a shower in my parents bathroom. Some thing shiny caught my eye after i got out of the shower. It was a gold colored satin/silk thong on the floor. Obviously it was my mothers and my...
    banannasplitz09 banannasplitz09 22-25, M 4 Responses Jul 31

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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 Apr 16

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    I was a kid, and it was snowing.

    My mother insist that i put a pantyhose of my sister to go outside (white one). After protesting i was forced in. I just remember now that even if i was really young it just turned me on. Few years after i started sneaking in my mother stuff to take her pantyhose, it all started...
    melit99 melit99 22-25 12 Responses Jun 21

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    One of many.I was about 14 my parents had gone

    out and so had my sister as I normally dressed in my sisters clothes I made my way upstairs to her room but was distracted when I stopped by my parents bedroom I could see a white strap hanging out of a draw so I went to have a look I opened the draw grabbed hold of the strap...
    daverick daverick 51-55, M 6 Responses Apr 13

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    The Beginning Of "me"

    I can remember it like it was yesterday, we were about 7 or 8 yrs old and a couple of friends and I were playing street hockey in the school yard. We had been playing for about an hour when I noticed Lori sitting on the step watching us. I decided to take a break and go say hi...
    Idare Idare 51-55, M 36 Responses Nov 13, 2012

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    Part II Early Teens To recap my first story,

    I was dressed as a little girl at the age of 4 or 5 in a plaid dress and Mary Janes by my older sisters for Halloween which is where I believe my cross dressing started. The first article of women's clothing that I was interested in was women's heel's and I used to sneak into my...
    jamie50 jamie50 51-55 5 Responses May 17

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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 46-50, M 9 Responses Jan 18, 2013

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    How It All Began

    Alright, so it all started with the Sears Catalog, hahahaha, and all the flyers we get in our newspapers, nice looking ladies in panties, bras, hosiery, shapewear, lingerie etc, fascinated by ALL of that, then one day i was about 10 or 11, my Mom was doing laundry and i had to go...
    SilkandLace SilkandLace 36-40, M 10 Responses Apr 5, 2012

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    My First Crossdressing Experience

    Although i had been trying my mothers and sisters clothes on secretley since i was about 10 my first real experience was when i was 15 i was at home one afternoon with my older sister of 17 and her friend i was watching tv while they were altering some dresses for a dance they...
    daverick daverick 51-55, M 19 Responses Apr 27, 2011

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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 19 Responses Aug 19, 2011

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    My First time fully dressed happened

    when I was 14, I had been wearing mum's panties and stockings in fleeting moments, but never found the time to relax and really go for it. At the age of 14 my parents agreed that I no longer needed a sitter when they were at work, Dad work as a pharmaceutical sales manager and...
    neverstop749 neverstop749 41-45 37 Responses Apr 3

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    Part 5 My girlfriend Marie

    and I had been dating around 3 months and were having sex on daily basis. We would usually drive to a private spot in the woods and get it on and she would always be wearing her leather sling back sandals from the previous story. I went to pick her up from school 1 day and as...
    jamie50 jamie50 51-55 1 Response May 25

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    Ever since I was young I have always wanted to

    dress up as a princess. The first time I lived my dream of being a princess was when I was 9. I as at my friends house and she had a trunk of disney princess dresses. Each dress had a lace top and a long satin skirt. When I was in her basement by myself I grabbed the Cinderella...
    deleted deleted 26-30 May 18

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    my first time was at age 5

    when my new stepsister moved into the family home. I was getting ready to take a bath when I noticed some of her panties on top of the hamper. I do not know what made me try them on but I just had to. this soon led to me trying as many of her clothes as I could before she left...
    jamie172 jamie172 46-50, T 3 Responses May 26

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    fercrox fercrox 46-50, M Apr 6

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    Joy Ride

    My first chance at going out crossdressed was when I was around 22 yrs old. I decided to go out and buy some sexy lingerie at Frederick's of Hollywood. I bought myself a 1/4 cup lacy bra with matching panties and garter belt. I purchased white stockings, a mini skirt, and a very...
    BarbieB BarbieB 56-60, M 30 Responses Feb 13, 2012

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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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    I remember how it started,

    it was a summer night and I was about 8 or 9 years old. I spent most of my summer at my grandparents house, I found a calendar that had some women wearing sexy lingerie, I was so fascinated with it. I ended up hiding the calendar,next I remember I was just in the bathroom and...
    Cdpantygurl Cdpantygurl 26-30, T 5 Responses Mar 14

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    How It All Began

    It all started many years ago when my ex girlfriend suddenly moved out of OUR place. She took all she could in one truckload, and told me to trash anything of hers that was left at the house. WELL…..The only thing left was a large plastic trash bag (full of her misc clothes and...
    ocxdresser ocxdresser 41-45 16 Responses Aug 13, 2013

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    I had just started puberty

    so I was probably around 11 or 12 years old and horny all the time. I had the house to myself in the afternoons after school. I was snooping around in my parents bedroom 1 day and discovered that my foot fit perfectly in my mom's pumps. Then I tried on her pantyhose. They felt...
    chrissyk48 chrissyk48 46-50, M 6 Responses Mar 20

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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 5 Responses Apr 10

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