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I Remember My First Crossdressing Experience

Personal Stories, Advice, and Support 2,943 People

    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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    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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    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 6 Responses Mar 7

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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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    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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    As an adult it happened today/tonight 06/05/14,

    went out to a club tonight for drag night with my wife and daughter in law, both of whom know and support me. I haven't gone full dress yet but was wearing my white bra (42b) which I don't need any padding for under a white tee shirt and pair of brightly colored VS panties that...
    greenmonkey17 greenmonkey17 46-50, M 10 Responses Jun 6

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    I remember this like it was yesterday.

    ..I was young...about 15 when it happened. I was hanging out with a family friend and ended up back at his house. We had been hanging out for a few weeks now and my parents never really paid any attention to me so it was no concern if I spent the weekend with him. So there I was...
    deleted deleted 26-30 8 Responses Apr 15

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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 14 Responses Dec 31, 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 5 Responses Oct 12, 2012

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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 7 Responses Apr 13

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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 15 Responses Jun 9, 2013

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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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    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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    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 5 Responses Jun 1

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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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    PART 4 I finally turned 16

    and purchased my first car for $200, it had its problems but it got me around and I went to visit a cousin who lived about 18 miles from where I lived. He was a couple of years younger but we always had a lot of fun when our families got together. While we were driving around...
    jamie50 jamie50 51-55 1 Response May 23

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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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    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 21 Responses Oct 10, 2012

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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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    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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    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 10 Responses Jun 21

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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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    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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    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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    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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    fercrox fercrox 46-50, M Apr 6

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    It was during my bi phase.

    I had longer hair at the time. It was in a truth or Dare thing. My friend had a lil sister who was same size as me. The challenge was to put on one if her dresses and some girls shoes and a hair band thing. We all went to the store right around the corner and I had to buy a...
    pardax pardax 13-15, M 8 Responses May 9

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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 15 Responses Aug 13, 2013

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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 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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    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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    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 22-25, T 3 Responses Mar 14

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    I had been dressing for years

    but had never ventured out of the house. I was online and decided I would book a makeover and attend a T-girl open party in another city where I could finally be the woman I've always wanted to be. I was very nervous getting on the train but began to relax as I got farther away...
    Julieallen Julieallen 61-65, T 8 Responses May 1

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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 41 Responses Feb 5, 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. 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 11 Responses Apr 12

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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 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 35 Responses Apr 3

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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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    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 13 Responses Feb 12, 2012

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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 4 Responses May 26

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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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    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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    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 12 Responses Jun 10

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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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    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 6 Responses Jul 14, 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 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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    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 22-25, F 4 Responses Jul 13

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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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    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 16 Responses Oct 22, 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 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 11 Responses May 23, 2012

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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 29 Responses Feb 13, 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 4 Responses Sep 8, 2013

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    I was about 10 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...
    tvCorinne tvCorinne 51-55, T 14 Responses