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I Remember My First Crossdressing Experience

Personal Stories, Advice, and Support 2,960 People

    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
    10 Responses Aug 26, 2012

    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
    5 Responses Apr 12, 2014

    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
    17 Responses Aug 19, 2011

    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
    17 Responses Aug 13, 2013

    My first time was scary i was a lat bloomer 16

    and thi is my story When i was 16 my sister moved out of state and my parents was helping with the move.They was going to be gone for the weekend.I checked out my sisters old room to see if i can move in it being as it was bigger.There was a box in the floor with goodwill...
    deleted deleted
    1 Response Sep 17, 2015

    My first cross dressing experience was my mums

    idea. I needed something under a costume for a school play, so stockings were the best option! It soon progressed to more, without mums knowing!!!
    rascalcam09 rascalcam09
    2 Responses Aug 19, 2015
    61-65, M
    1 Response Sep 27, 2015

    It was back when I was 11 my sister thought it

    would be funny to dress me up in a short strapless black dress with a strapless bra panties and tights with some heels as well I felt so girly that day because she also done my hair and make up.
    martha1995 martha1995
    6 Responses Dec 29, 2015

    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
    27 Responses Aug 4, 2011

    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
    22-25, T
    13 Responses Jun 9, 2013

    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
    33 Responses Nov 13, 2012

    I lost a bet in early 90s But it's evolved into

    something I love and desire. I wish more people were acceapting.
    deleted deleted
    2 Responses Nov 16, 2015

    First crossdressing memories I originally

    posted this over two years ago and deleted it when I decided to remove myself from EP, however I have now reincarnated and decided I will share again with you my ‘foundations’ into crossdressing. My very first memories go back to when I was probably about 10 years old. I...
    6strap 6strap
    66-70, M
    4 Responses Jan 31, 2015

    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
    8 Responses Jun 6, 2014

    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
    36-40, F
    3 Responses Sep 8, 2013

    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
    14 Responses Jun 14, 2012

    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
    4 Responses Apr 29, 2014

    LOL the very first time I can remember was

    when I was three or four and my mother sewed a dress for me to wear. Didn't take her long and I remember spinning around and around in the living room until my sisters got home from school. Dressed or not I remember my sisters friends always asking who the little girl was...
    amandatrane1 amandatrane1
    51-55, T
    1 Response Sep 19, 2015

    i remember when i was around 10 i discovered

    the feelings of my mom's pantyhose and stockings when i took a bath. My mom would wash these by hand and leave them in the bathroom to dry. It was rather easy to play with them and then hang them up again. About the same time, the older boy who lived next door introduced me to...
    cdkrissy cdkrissy
    56-60, M
    Sep 19, 2015

    I tried on my sister's bra

    and panties! It felt so good I came in the panties for the first time! Haven't stopped trying on them since!!!
    TAMMY529 TAMMY529
    66-70, M
    1 Response Jul 16, 2015

    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
    22-25, M
    5 Responses Oct 12, 2012

    The very first time I wore any womens clothes I

    was 12. I was staying the night at my friend seth's house. That night his mom and her bf went out and left us playing video games. They weren't gone long when Seth asked if I wanted to look at his mom's bf ' s magazines. We were looking at some hustlers when he pointed to one of...
    hollandcd3766 hollandcd3766
    41-45, M
    5 Responses Sep 16, 2014

    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
    May 18, 2014

    I was 5 years old when my 8 year old sister

    first dressed me up. I still remember the panties, short denim skirt, girly shirt, Disney princess watch. I didn't know what I was feeling but I loved it! I then would try to give hints to tell her to dress me again and again without seeming like I wanted it. During that time I...
    RoseStrayed RoseStrayed
    22-25, M
    6 Responses Jan 16, 2015

    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
    6 Responses Mar 28, 2012

    ok this isn't about my first experience,

    this is much more of a thought that I had. So many of us talk about how our sisters have been involved in the beginnings of our crossdressing. Many have been dressed by our sisters either for play or malice. For those who learn about our feminine side in a playful manner with...
    Freja14 Freja14
    36-40, T
    Jan 16, 2015

    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
    1 Response May 24, 2014

    When I was 5 years old,

    my older brother urged me to put on my sister's bathing suit. Something clicked, I started wearing panties before moving on to bras and other lingerie. I'm not passable, so I don't go out dressed. I do sometimes go out wearing panties and bra under my clothes.
    mandywantsit mandywantsit
    56-60, M
    5 Responses Feb 17, 2015

    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
    8 Responses May 2, 2014

    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
    10 Responses Dec 31, 2013

    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...
    deleted deleted
    4 Responses Jun 1, 2014

    I really didn't understand it at first.

    But my Mother used to dry her stockings on the shower rod. Then all of us (two Sisters) had to help with the wash and dryer. It finally became too much, pulling my Sister's nylon panties from the dryer....that I finally tugged myself into a pair of their pretty PANTIES!!!
    chrisg03 chrisg03
    56-60, M
    4 Responses Apr 29, 2015

    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
    7 Responses Jun 10, 2014

    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, 2014

    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...
    51-55, M
    9 Responses Jan 18, 2013

    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...
    deleted deleted
    11 Responses May 23, 2012

    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...
    deleted deleted
    9 Responses Oct 11, 2012

    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
    61-65, M
    27 Responses Feb 13, 2012

    I saw my moms bra and put it on in the bathroom

    was the first time. From there i explored hers and my sisters panties and clothes.
    BicuriousSissyBoi BicuriousSissyBoi
    22-25, M
    3 Responses Jun 14, 2015

    Nothing too crazy... When I was younger I used

    to shower with my mom. Seeing her put on her underwear and bra, I was always being a boy I only had underwear. Out of pure curiosity I wore my mom's bra and underwear, and grew fond of it. Just exploring my femininity is always not just a thrill but a huge part in...
    pk96701 pk96701
    Jan 31, 2015

    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
    17 Responses Aug 7, 2011

    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

    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
    36 Responses Feb 5, 2012

    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...
    deleted deleted
    2 Responses May 26, 2014

    My first experience was wearing one of my

    mother's bathing suits. She kept all her more intimate clothing in one part of her dresser. You opened the door and there were two pull out shelves. On the top she kept her bras and panties and on the bottom she had her stockings and bathing suits. For some reason, I was...
    deleted deleted
    2 Responses Oct 13, 2015

    about 4 or so liked to steal my moms panties

    and wear them. The attic access was in my room and I spent hours wearing dresses and skirts from there. I got caught and told her I wanted to be a girl, I was told I couldn't and to stop wearing her clothes. I didn't though. I progressed to wearing her clothes and make-up when...
    Amandolly2 Amandolly2
    56-60, T
    4 Responses Dec 8, 2014

    I remember our first time,

    we had been in sexual discovery mode and had ventured into anal play. I was amassed how much I enjoyed it. I jokingly said we should role play me dressed as you and you playing with my ***. To my surprise she said "that is hot". later in the day she said when I got home to...
    Macycraz Macycraz
    41-45, M
    1 Response Sep 17, 2015

    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
    26-30, M
    2 Responses Jul 31, 2014

    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...
    deleted deleted
    11 Responses Oct 22, 2012

    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...
    deleted deleted
    13 Responses Jun 21, 2014

    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...
    deleted deleted
    13 Responses Mar 28, 2012

    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
    9 Responses Mar 25, 2012

    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...
    deleted deleted
    16 Responses Oct 10, 2012

    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
    2 Responses Jul 14, 2013
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