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I Remember My First Crossdressing Experience

Personal Stories, Advice, and Support 3,141 People

    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 26-30 17 Responses Oct 10, 2012

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    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 18-21, M 6 Responses Jan 16, 2015

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    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

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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 31 Responses Aug 4, 2011

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    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

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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...
    deleted deleted 26-30 14 Responses Mar 28, 2012

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    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...
    Jazonx Jazonx 36-40 3 Responses Sep 17, 2015

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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 7 Responses Mar 28, 2012

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    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 5 Responses Apr 29, 2015

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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...
    deleted deleted 26-30 12 Responses Oct 22, 2012

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    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 18-21 6 Responses Dec 29, 2015

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    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 2 Responses Sep 17, 2015

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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 5 Responses Apr 12, 2014

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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 18 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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    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 10 Responses Mar 25, 2012

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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 41 Responses Nov 13, 2012

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    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

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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 2 Responses May 26, 2014

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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, 2014

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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 19 Responses Aug 7, 2011

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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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    WILLLICKU WILLLICKU 56-60, M 1 Response Sep 27, 2015

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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 12 Responses May 23, 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 13 Responses Jun 9, 2013

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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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    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 15 Responses Jun 21, 2014

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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 61-65, M 29 Responses Feb 13, 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 39 Responses Feb 5, 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 14 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, 2014

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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 10 Responses Jan 18, 2013

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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...
    GirlyLisaTG GirlyLisaTG 31-35, T 4 Responses Jun 1, 2014

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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, 2014

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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 9 Responses Jun 6, 2014

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    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 6 Responses Feb 17, 2015

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    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

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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 3 Responses Oct 11, 2014

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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 22 Responses Aug 13, 2013

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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 26-30, M 4 Responses Jul 31, 2014

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    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 36-40, M 6 Responses Sep 16, 2014

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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 7 Responses Jun 10, 2014

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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 36-40, F 3 Responses Sep 8, 2013

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    Sisters friends clothes.

    I was about 14 at the time my parents had gone away for the weekend and i was left in the care of my older sister.She told me that she had planned a night out with a girlfriend and wouldn't be back until the early hours of sunday morning, great i would be left alone to dress in...
    daverick daverick 51-55, M 6 Responses Oct 28, 2015

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