How old were you when you started and who's clothes?

[Alexa 1960]

Until the age of 18 I never have worn women clothes. It began at a garden party at my girlfriends home. It was a sunny day but in the evening it became cold. My girlfriend noticed it and went into the house to take some clothes for me and two other girlfriends of her. When she came back she wore a dark red twinset and held some other clothes in her hands.
I knew of her love to classic style clothes and she was just the type of girl who looks beautiful in it. Each of the two girls got a cardigan and when she came back to me she handed me a light grey pullover, I mean I thought it was an pullover.
Then I noticed the many little buttons and I realized that it was a cardigan too. "Would you wear this cardigan? It`s one of my larger twinsets and the size must be ok for you" she said. I took on the cardigan leaving all buttons undone. First I was a little bit ashamed of wearing a girls cardigan, I have never worn any cardigan before and I tried to hide the button side. My girlfriend noticed it and said “Don`t you like cardigans? I love them and I know that it`s a woman style but it looks very nice to you, isn`t it?” turning her head to the two girlfriends. “Yes indeed, but for a man it would be better buttoned up,” one of the girls answered. “Oh, but not completely, I think it would look better with only a few buttons closed,” the other girl replied. My girlfriend turned to me and began to close some of my cardiganbuttons and I hoped that the three girls didn`t notice my face turning red.
I went into the bathroom, especially for looking into the mirror to see my cardi outfit and was surprised about my “new look”. It looked really good and I closed the cardigan in different ways such as my girlfriend often did. I noticed that my face colour became normal and went back to the three girls. I began to enjoy the feeling of wearing one of my girlfriends cardigans and listened interested to the girls conversation about sweaters, twinsets, skirts, dresses, nice buttons and all the other girly clothes till this theme ended. I was surprised about myself that I had so many fun by listening to these girly things for such a long time, I have never done this before. For the next two hours we played cards, spoke about all and nothing and had many fun. I hated that the time was come for me to go home because I had to go working early next day. My home was only about 15 minutes away from here and I decided to walk this way. When I began to unbutton the cardi my girlfriend came to me for a long kiss and I must say it was a very nice special feeling for me, both wearing these beautiful soft woolen clothes.
“It`s cold tonight, you can give me back the cardigan tomorrow” she said to me closing the buttons I just had opened.
This day I will never forget and it was the beginning of the nice feeling wearing women cardigans and twinsets, first in private but after a while I loved to wear them in public too.
Now I live together with the same girlfriend for over 25 years and we both enjoy this wonderful woolen feeling.
Today our sizes are of course different so that I have my own cardi and twinset collection and we both love to wear them together. We have bought some skirts and dresses for me too, but I wear them only at home, I have never worn them in public, but perhaps…..?
We like to remember this first fashion day and I am happy to have such a beautiful girlfriend till today.

Love, Alexa.

Sorry for my bad English, but I have only a small English vocabulary.

[Rachael Warren]

I was 8 or 9, can't be exact, I seem to recall doing this after we had moved house and I had a bit of freedom. My parents didn't come home from work until about six, so I had a couple of hours, just had to avoid my brother.

I didn't have a sister at the time, so it was my mothers clothes that I "borrowed", never did get caught.

Rachael.

[HaleyPink2000]

Well the first time I was 5 and my Mother did spank me with my Grandma very Mad at Her for doing so. They did argue for hours over Her spanking me for putting on Her slip that was on the floor. My Mom said " I don't want Him to be a Fag". I remember her words to this day.

Then the next time I was 15 and In my Mom's closet dressed.

Well then I was in denial for years.

Love to you all!

Haley

[Jane]

I was about 14 home from school alone just felt so right to try my sis cloths! Now i love it feals so nice to wear some sexy underwear insted of boxershorts

[Nicole Lee]

Started a few years ago when I was about 13 (I'm 18 now). I used to LOVE wrestling, and like any young kid, I wanted to become one. I would used to "wrestle" with myself, like, throw myself onto the bed and such while wearing my tight longjohns.

And I don't know WHAT made me do this, but I went into my mom's room once, and found a pair of white pantyhose. So, I put them on, and pretended they were the tights that wrestlers wore. They were a good substitute back then, but what I REALLY wanted were some spandex (not that I knew what spandex was back then). Unfortunately, my mom didn't have any shiny spandex in her drawers.

However, when I went to my cousin's house once, I saw her wearing a pair of SHINY pink spandex bike shorts (I think shiny bike shorts were popular back then in 1999-ish amongst the young teen crowd). She had three pairs of shiny spandex shorts (because she was a ballet dancer, I think). That bright hot pink pair, a bright lime green pair, and a black pair with stripes on the side. Eventually, after going to her house several times (my parents would leave me with her family when they had to go somewhere by themselves, or if I wanted to sleep over), I found the courage to go into her drawer and steal the pink pair of shorts. I was in love. Hahaha.

Since then, I would be a young little thief and steal spandex (whether it be cotton or shiny nylon) from her drawer. And not just her, either. My aunt in New Jersey had some nice spandex clothes. I stole a pair of red bike shorts, shiny black spandex leggings, and a shiny black leotard from her. And another cousin who lived in Pennsylvania, stole a few pairs of panties from her (including a white one with pink hearts, it was so cuuuute! I want to buy a pair).

I have loved wearing spandex ever since I started. Except now, it's not so much the shiny stuff anymore. It's more of the ballet dancewear that I like now. A black long-sleeved cotton leotard with a pair of white or pink nylon footed dance tights. But, I still have some shiny stuff that I've bought.

Anyway, that's my life story. Bye now!

[hot chelsea]

i started when i was 13. it was great i was home alone(except for my sister,who locked herself in her room) one day and decided to lay on my parents bed and read one of my mom,s magizines(i've loved womens magizines since i was six)but i saw a bra sticking out of my moms drayer. i went over anddecided to see what bras were like it took me 5 minutes to get it on right but once i did i just loved it i then went to my 14 sisters,Molly, room(she had always tried to get me to wear her clothes, she thought it was cute) and told her how much i loved tthe bra i was wearing so she went and grabbed a box of tissue paper and stuffed my moms bra. then she got some of her clothesout. turns out we wore the same size(and still did until i turned 18) but once she saw me in her clothes with a stuffed bra on she decided to call mom at work and ask if she could go shopping if she took me with her mom said yes so i put my clothes back on and walked to the store that was across the street from our neighborhood. she then started grabbing different bras an holding them up to me withthhe cup pushed out. and found a size she liked on me she then grabbed ten of different style bras in the size she had chossen,grabbed alot of different colored panties, aqnd some lingere and otheer various articles of womens clotheing. then every day she'd take me somewhere(id be wearing my ne clothes under mmy boy clothes) and she'd take me into the girls bathroom to change and do my make up. shed put my clothes in her purse and wed hang out as to sisters. now my girlfriend and i do this almost everynight.
love to all
Chelsea

[michelle19845]

i was looking for something and ran into a bag,one that had panties in it and after that i started wearing dresses and nylons with it.i wore sister's and mom's .i was lucky we were all about the same size.later on i started buying bras and panties at the store when i was 16.i've built up wardrobes and binged sadly a time or so.(bad news).now it's whatever makes me look and feel feminine.



michelle

[Vaerise]

17 yo. My mom's bra. Though I have been dying to try on womens clothes since 10

[MICHELLE739]

it was when i was about 4 yeasr old i would sneak in my sisters room she is 2 years older than me i would go through her dresser drawer and take one of her panties and put them on and got caught by my mom and told me not to do that again the next day i found a nice little blue dress that my sister left on her bed no one was around so i put on along with some panties pantyhose and shoesi got caught again by my mom and she made me wear it infornt of everyone. A few years later at about 9 years old i started all over again this time my sister had better clothes i would find a nice black lace bra and panty set and put it on with a nice red skirt and white blouse and a pair of mom high heels and was walking around the house nobody was home so i thought my mom and sister caught me got yeld at with a spanking and said you like to wear your sisres clothes then we will have to take you shopping for some dressed like that i was yelling that i didn't want to but i had no choice to and i was happy when we did because now i dress up everyday now

[BeckyB]

I remember this like it was yesterday. I was 4 years old. I was caught by my oldest sister wearing my youngest (4th)sisters slip and dress. I am the youngest of six with four older sisters. I got caught with my 3rd sisters clothes several times through out my time at home.

[lisa_sf]

i started when i was 13. it was great i was home alone(except for my sister,who locked herself in her room) one day and decided to lay on my parents bed and read one of my mom,s magizines(i've loved womens magizines since i was six)but i saw a bra sticking out of my moms drayer. i went over anddecided to see what bras were like it took me 5 minutes to get it on right but once i did i just loved it i then went to my 14 sisters,Molly, room(she had always tried to get me to wear her clothes, she thought it was cute) and told her how much i loved tthe bra i was wearing so she went and grabbed a box of tissue paper and stuffed my moms bra. then she got some of her clothesout. turns out we wore the same size(and still did until i turned 18) but once she saw me in her clothes with a stuffed bra on she decided to call mom at work and ask if she could go shopping if she took me with her mom said yes so i put my clothes back on and walked to the store that was across the street from our neighborhood. she then started grabbing different bras an holding them up to me withthhe cup pushed out. and found a size she liked on me she then grabbed ten of different style bras in the size she had chossen,grabbed alot of different colored panties, aqnd some lingere and otheer various articles of womens clotheing. then every day she'd take me somewhere(id be wearing my ne clothes under mmy boy clothes) and she'd take me into the girls bathroom to change and do my make up. shed put my clothes in her purse and wed hang out as to sisters. now my girlfriend and i do this almost everynight.
love to all
Chelsea

Wow, AMAZING that a 14yo girl had enough money to buy you 10 bras, lots of panties, more lingerie, and various other articles...

[Marissa_njts]

I first started when I was about 6 or 7. The odd thing is that I never understood why I had the urge to, but I felt I had to. I remember locking myself in the bathroom, going through the hamper, and trying on my sisters clothes. My first article of clothing ever worn was grey pantyhouse, and an orange and grey skirt/shirt combo. I would then go into my sisters room, grab the shoes, and bring them into the bathroom. That is probably the only time I ever fit into her shoes. I would turn the bathwater on and pretend to be taking a bath, while I was sitting on the toilet dressed up. From there, I would dress every opportunity I could. Along with dressing came the guilt, for i am a very successful, athletic boy who did not fit the mold of dressing in girls clothing. I would dress every morning in middle school before I left for school. It is amazing to look back and see how early we started. My first recollection was around 4 when my mom used to let me wear her night gown. Hmmmm, could that have been a trigger. I used to fall asleep every night wearing pantyhose as far back as elementary school. It is funny how 20 years later things have not changed. In fact, the only thing that has changed is my desire to do more!!!! I even took hormones several years ago. The effects happened so quick I had to stop

[Charlene Marie]

Beautiful picture of you. I was in the seventh grade. I put on my mothers pantys and
bra and a slip of my older sisters. The feeling overwelmed me, I loved it but didn't know why. I was sitting at my mothers vanity trying to put rollers inmy collar length hair. My mother found me but she tried to be cool. She asked me if I wanted to see how I would look all dressed up. I did, so she dressed me in a skirt and blouse and put
a little makeup on me and lip stick. Then she asked me if I wanted my hair curled and
before I could think about it she took me into the kitchen and shampooed and set my
hair in rollers. I've been hooked ever since. About twenty years later she told me
she did it so I would get the idea out of my system. It didn't work.
Thanks for listening. Big Hair
hair in rollers

[michelle19845]

i started by wearing my sister's dresses and then her panties.i remember ther being disney characters on themi later went to mom's bras and panties she had in bags downstairs for garage sales and later on came across dresses and pants.
i also remember wanting to be the "baby girl" when me and my sister played when we were around 6.


michelle

[Stormgirl]

don't know and don't care anymore

[IRIA]

I think I was about 11 or 12. I slipped out of the house and tried on one of my mom's bras. It just felt so good, I just started doing it more and more as a child.

[Helen MC]

When I was 12 I summonsed up the courage to take a pair of my sister's white cotton "Cherub" briefs from her bedroom cupboard and wear them. I had found something attractive about knickers for a while before that but this was the first time I tried a pair on and the result was mindblowing! From them on I used to secretly wear her knicks both plain white briefs and navy blue ones and her more girly floral patterened panties except on PE Days when I had to wear the hated Boys Y Fronts changing into "my" knickers again when that dreaded lesson was over. I was able to ditch PE when I was 15 ands have never worn male underwear since! I also started to wear my sister's skirts, bras etc when home alone and also borrowed some of my Mum's clothes both knickers to wear under my trousers for that day and other items to dress up in when alone. The rest is history!

[Marsha]

I was 5 when my two older sisters dressed me in our mother's bra, garter, and stockings. It was not long after that I had my first feelings that I should have been born female. These feelings would come and go and the crossdressing would do the same. When I was 12 I dressed again in my mother's clothes and this time I filled the bra with socks. This was my first erotic turn-on to CD. Since that time I have kept my feelings locked away in a closet in my mind. Giving in occasionally and then purging. I've only accepted my inner self in the last two years. A lot of lost time don't you think?

[HIGH HEEL BOOTS]

i was 12 years old and it was my sisters bra and panty set

[Jennifer Rae]

5-years old when my mother dressed me in the dress she bought for my cousin's birthday present and then took pictures of me. Still have the photos in the family scrapbook.

[polo_shirt_fetish]

When i was 10 or 11 i snuk into my mums room and tryed on a bra. I still dont know why but i found it sexy so i kept doing it. Right until this very day.

[Jayne]

I was only young when I tried on my first shoes.
Then I progressed to my sisters tight and panties.
I moved up to nail polish and even got hooked on bra's when no one was home.
My younger sister had dressing up dresses which I would drop in the outside toilet and make excuses to go and lock myself in with the pretty frilly yellow bridesmaid dress.
The girl next door gave lots of things for my sister to dress up in and I realy enjoyed thies more than she did.
I even did my paper round cross dressed once and the thrill of getting caught enhanced the experience.
My wife is out and i am enjoying a few hours of crossdressing as I type.

Bye for now

[Madeline_K]

New member so just jumping on the bandwagon.

My first memories of crossdressing were when i was in first grade. My female cousin lived with my family. We were about the same size at the time and I remember wearing her frilly socks and white Mary Jane shoes. I asked myself why it was boys couldn't wear slip on shoes because at the time I HATED tying my shoes.

My first true crossdressing came when I was 10 in fifth grade. Women's shoes were my first love, still are. My mom didn't have high heels or stilettoes, but they were cool nonetheless. So one day when I was all alone, I tried on her shoes. Loved it. I could wear them until seventh grade when my feet got to big. After a while, I decided to get bolder and put on pantyhose, then underwear, panties, and dresses. I didn't get into makeup until college.

Real long story. If you want to read the whole thing, drop me a line here. Its on my CD Livejournal, the only other thing that keeps me sane.

Madeline

[Deana_CD]

Gosh, I guess I was about 10 or 11. Began by trying on my mom's red slip and bra. I couldn't beleive how good it felt, the way the satin felt against my skin. Soon I was raiding my cousins' pantie drawer at every opportunity. The feeling of her panties tightly cupping my bottom was absolute heaven! By the time I was 12 or so I must have "aquired" about 20 pairs of panties, along with a few bras and several pairs of pantyhose

[tullyxxx]

started about nine used to try my mothers undies on always felt like a girl useless at sport but as i had 3 older sisters and they really wanted a sister i was treated as one my blonde hair was down my neck before my mother would let it be cut . my sisters were always dressing me in girls clothes they said it was for fun but they really liked to make me look good . so i have always liked being a girl even down to seeing boys a nice and playing with girls , but i really took off at 15 when i went on the stage with my sister as she was an actress what a great time lovely dresses and make up and no one taking any notice of me it was heaven so much i was getting attention from all the men there so am still dressing now it is ok cause my wife dont mind and treats me more as a sister than a husband i love the freedom of not having to hide it from her even lets me have a man friend so i am very happy but feel sorry for someone who has 2 hide it from their wives must be x very frustrating hope you all ok love grace