When did you first crossdress?

Do you remember the first time you tried on an item of women’s clothing?

I remember putting on my mum’s fake fur coat around age 7 and getting a thrill from my appearance in the mirror. I knew at once that this was part of my future. How about you?

I remember having an pantyhose fetish at an very early age. I think I was 10. I loved The way they looked on women, how "see through" they were, The shine they gave off and how cute they made feet look. It was within that same age that I wanted to know how they felt on me so I stole a pair of my mom's. They didn't look as good as they did on other women (to find out it came down it brand and such) yet they felt amazing! There was little turning back after that.

Probably about the age of 10. Those pantyhose just hanging there in my grandmothers bathroom were just too much to resist.:o

I used to be dressed up in ballerina outfits my sister had as she was growing up... about 4 years old I think. I remember about age 4 trading underwear with a girl my mom babysat for. They were white with strawberries on them.

My sister and I were very close. She'd dress me up starting around 5 or 6. Alot of kids play dress up like that, but I liked it too much. By my early teens, at pajama parties I was my sister's make up manequin.-Celeste

As early as I can remember...probably around 4 years of age.

Probably as a single digit midget. I fondly remember taking my mother's nylon slips off the clothesline and trying them on. I loved the feel of the material. I had no conscious thought that I would like to have been born a girl. I had no sisters or female playmates. No one dressed me up. Maybe, if my mother wore cotton slips I would have turned out differently????

I am a late bloomer, I guess..it was about 10 years ago, my wife and I were playing around and she put her bra on me for fun when we were "messing around" one evening..shortly after I suggested we go find a lingerie set for me at the dept store, so we went and she helped me get one...the novelty kind of subsided for several years..then last year for whatever reason, I got that outfit back out and tried it on..then went on an ebay spree and slowly gathered more stuff until i was "evolved" enough to go out in public..anyway I digress lol

I might have been 4 or 5, I would go into my moms closet and put on her girdle,
Then try walking around in her heals.
That was OK for a while, but when she caught me wearing her girdle and
nylons in bed when I was 10, I got the "TALK".
Had to hide stuff better, Under the mattress was no good anymore; so I went
to work and built a false bottom to my built in dresser drawers. Worked like a charm.
Then when I went off to the Navy, I had to purge everything, That hurt.
I left a note in the hiding space saying, "HA, I caught you looking at my Hiding Space"
The old house is still there, all though we moved out 40 years ago; I wonder if anybody
found the note.
Rader

about 4 years old---slipped on some nylons, and never looked back!

School holidays, ten years old, and I had the house to myself during the daytime. Went through my Mam's drawers looking for tights/pantyhose (I'd been obsessed with them since I was about five) and pulled out some sheer black ones. I put my arm(!?) in them, then panicked and went back downstairs. A few minutes later and I was back up...this time putting one foot in over my sock...panicked again and back downstairs. Sat down, and then promptly went back up, took my trousers and socks off, and pulled them on. I can sometimes recall exactly how I felt at that moment... but it only lasts a second or two...a "first hit" type of experience, never fully recaptured. I couldn't keep out of them after that...

I don't remember precisely when I did it the first time, nor what compelled me to. But it was in high school, with my moms clothes.

Four and five years old, my mother had me put on dresses she made then have me get on a chair so she could make the hem straight. Sometimes wore those dresses all day long. My father was away in the hosptial then and never knew my mother dressed me in dresses.

Mom's panties and slip at about age 7 and then her wonderful pink OBG with 4 garters and lace up back.

I was 6 years old. I was enchanted by pantyhose. I found a chance to wear my mother's hose along with a skirt and blouse. Of course they did not fit, but I was thrilled and began pursuing crossdressing as often as possible. Over forty years later, I'm fully dressed as I type this. The thrill has never escaped me.

I was 11 or twelve just watched a movie where a man dressed ad a woman and somehow wanted to be like them so id borrow my moms clothes anf do it got caugjt a couple timed but that hadny stopped me ftom dressing. I to love thr feel og nylons on my legs

Aged about six. Tried on a pair of my sister's panties in the cupboard under the stairs. Felt wrong but oh so right.

I was 12. Pantyhose weren't out yet but my mom used to hang up her stockings to dry on the bathroom towel rack. One day she also had her garter belt there. I tried them on. Couldn't believe how nice they looked. Even better was how they felt! I was hooked and the rest is history.

pretty much since i was 2 i think so 16 years ago. I had two older sisters who would dress me up and push me round in a dollies pram and gave me girl names, however i only really realised i was a crossdresser by secondary school as i simply didn't realize i was one before. i will just say i'm glad my parents were so accepting :) x

I was a bit of a late starter, I suppose, 14 yrs old. It was my sister's 16th birthday and we had all gone for the weekend to the Disneyland hotel in S. California, just outside our home in LA's San Fernando Valley. It was then while all were elsewhere and I was alone that I first realized the possibilities. There in the bathroom were my mother's and sister's bathing suits hanging to dry. Really, it was almost instinctual as I pulled my mother's one-piece suit off and just… well, put it on. Without a thought, I remember so clearly, I pulled off tons of toilet paper to fill the suit's 36D cups. From there, of course, all my mother's makeup seemed just natural to try on too. To say I was excited hardly describes it. But it was when I first pressed her Avon Periwinkle Pink lipstick to my lips (yes that was the shade, will remember it to my dying day) when all came to be and I discovered my true self. With each stroke of that lipstick, I became more alive than I had ever felt. After a bit of work, blush and mascara as best as I could manage, I couldn't believe how attractive I had become, feeling and looking just like a girl… my reflection in the mirror that of nothing but a newly discovered ingenue. It was such an amazing day, perhaps the best of my life. :kiss:

One month ago, I was in my parents room. I got to try on a couple bras, panties, and a nightie. Loved every second of it.

I wish I found this out about myself a lot earlier. I need to catch up!

I was 11 when I 1st dressed. I wore an old dress that was just sitting out in my mum's bedroom

Honestly, I don't remember. The first time I did it knowing that it was "abnormal" was around ten maybe? However, when playing house with my cousin, it was earlier. And I'm told my mother and sister enjoyed dressing me up as a girl, although I also remember rejecting the typical lace-sleeved shirts of the 70s at the time around seven or eight, probably because that was about the time outside influences began telling it was wrong to do that. Wasn't my parents, though.

I was in day camp at age 9 or 10 and the camp did Oklahoma. A bunch of the boys were dress and sang "I enjoy being a girl". I think that was my first time, but not my last!!

I knew I had a fem side around 5. By kindergarten I already envied the cloths the girls got to wear. Although I can fit in with the guys, I seem to gravitate towards the girls. I seem to feel more comfortable in a group of girls. Once I have been there for a short time they seem to accept me as one of them in our conversations. I started dressing very young, and did so until present aside from a few breaks.

I was 7 years old. I was always fascinated with nylons and girdles. My mom would have her friends over for coffee during the day and they would sit around the table,smoking cigarettes and gossiping, often wearing nylons and I wanted to be just like them. One day when she was out, I snuck into her underwear drawer and put on her girdle and nylons. It was an incredibly exciting feeling. I loved the tight feeling. It was sexually stimulating, and I didn't even know what sexual stimulation was yet.

I tried on a pair of pantyhose when I was 7 or 8 years old. That electric feeling that surged through me is still with me and I remember it fondly. The first time I really went all out was when I was 10 or 11 years old. I had a day to myself, mom and brother were gone all day. I dressed up in a nice business style black skirt that was 2-3 inches below the knee. A blue sleeveless blouse... of course the bra and panties as well as off black pantyhose, girdle. And the cutest pair of velvet 3 inch heels. I spent almost my entire day dressed in that and was in heaven all day. That was probably the single best day of my life in regards to cding and I regret not having more days like that... even though I did have the opportunity.

Here is an earlier post on this subject.

http://www.crossdressers.com/forums/...t=#post2409283

9 or 10 years old, moms panties

I was about 6. I was about to hop in the shower when, surprise, my sisters panties are laying on the bathroom floor. I got them above my knees when, no knock or anything, my sister comes in the bathroom and sees me. I don't remember if I pulled them up after she left but needless to say I denied it when she brought it up at dinner later that night.

1950. I was about three or four, and got caught wearing mom's nylons. She really put the shame and guilt trip on me. LOL

I must have been about five or six, I can't remember exactly. I remember discovering my mother's nylon slip and for some reason wearing it. I am so glad I did.

I would have to say it was my sister junior girl scout dress, it was short for me, but felt great to be a girl, around 12, hugs.

my own accord I didnt get into it hardcore till about a year ago. My mom dressed me up when i was a baby or so im told.

I was 12 and tried on a pair of knee highs while my mom was sewing up my jeans. Next came the bra, but it was when I discovered and wore her babydoll with sissy panties that I was truly hooked.

Between the ages of 6-8, that was ages ago. The urge has waned, at times, but since 2004 it's been also always 24/7. There is no heading back for this old bag.

Between the ages of 8-10...

I think it was around 7 or 8, and what started it was my mom's Platex rubber girdle (open bottom), plus the nylons needed to hold it down. I'd love to have one of those girdles today. :daydreaming::daydreaming:

For me the underdressing started back when I wss just a boy. Probably sometime in the late 60's
and the full dressing started somewhere around 2005-2006

When I was six years old. I put on my mothers clothing. It began there and never stopped, just a pause now and then. 46 years and counting.

I think that I was 11 or 12. My mom did custom sewing & alterations. She was sewing bridesmaid dresses for a wedding. She needed to check a hem on a dress and I was just the right height! Screamed & hollered on the outside against it, but loved every moment of it on the inside! I was hooked for ever!

In my room at my Grandmother's was a closet full of her stuff. The earliest recollection I had was for some reason, I wanted to try on this pair of funky, high heel, beaded sandals that fit me at the time. I was maybe 9 or so. I remember how it arched my foot and looked like the ladies in the catalogs etc. From there, it just built on top of that until voila, you see what you get in the avatar. :)

I was probably about five years old. I was in the bedroom of my "youngest" sister and my other sisters decided that they would dress me in a corset belonging to my aunt, who was visiting at the time. The memory is so electrically clear to me; the feel of the corset, the soft material on the panels and the sunlight shimmering off the silvery satin. From that time on I dressed as much as I could. The sister, who was just a few years older than me, used to put makeup on me and make me sit outside by the street. I had three sisters, all older. What is interesting is not just the particulars of that first time but the way in which it shaped my sexuality. Dressing and underdressing in feminine clothing became more and more frequent. I also found that I enjoyed being a "bottom" sexually. I don't regret that day and neither do I blame my sisters for doing what they did. I believed that they unlocked something inside me and that set a course in my life.
I have friends whose son began dressing and using his mother's makeup at an early age. His mother just let him do it and never admonished him. He would borrow his mothers clothes and use her makeup quite openly and often in her presence. We talked about it a little and I told her that her tolerant treatment of her son was admirable. Don't we all wish that we had had mothers like that.

When I was around 7, my mom had me wear a pair of my sister's tights when my long johns were in the wash. I was going ice skating with my sister, I made a fuss, but found that I enjoyed wearing them!

My mother wanted a girl. And after her third son was born, she made me her little girl for a while. ( I was @2).
My earliest memory is being dolled up in a yellow satin dress and having a ball. Later she stopped dressing me, but I had the taste for it by then, and would sneak her slip into bed with me like a security blanket.
I was in the closet until I married my accepting wife. The next 38 years were peaceful private dressing with a loving partner who dressed with style.

When I was the ripe old age of seven, I took a dare from an older male cousin to wear panties and a dress. I was hooked from that time on. I am now a 60 plus senior citizen with a full feminine wardrobe, wigs, and accessories. If my cousin was still of this earth I would thank him for the dare because it helped me discover who I truly am.

I was maybe around 11 or 12 years of age and was about the same size as my older sister. Went into her room one day and some of her school clothes were laying there. After working up my nerve I went all the way.. bra, undies, pantyhose, and her skirt and blouse. It all fit me perfectly.
In my mind I was ready for school, but oh well, maybe in another life ..... :)

After many years looking and imagining it was me in those clothes, I snuck into my parents bedroom, tried on a pair of mums tan tights and slipped on a pair of 2 inch heels which felt so right. I was 10 at the time.

About 5 I played mothers and fathers when staying over with relatives.
I was the baby dressed in a frilly pinafore dress with puffy sleeves.
I wore frilly panties over my nappy and a dummy to finish it off.
That night at the dinner table the high chair was retrieved from the garage and I was sat in it.
I spent that night in a cot.
I can't say I did not enjoy it. I played the baby a few more times and then grew up to be an aunt with bra and high heels.

My first thoughts about dressing are among my very oldest memories, at 2-1/2 or 3 years old. By that time, I had figured out that men and women dressed differently, that my mom and grandmother were very attractive when they dressed to go out, and that I wanted to look like them. But at that age, I had neither the clarity of mind nor the physical ability to do anything about it in practice. What gratification I got came from my mom occasionally putting lipstick, nail polish or jewelry on me, which both of us enjoyed for our own reasons, I think. My first memories of actually trying on women's clothes and shoes on my own start at around 5 years, and continued more or less without a break (although mostly in private) after that. As I've mentioned in another thread, at age 40 I had a kind of epiphany that resulted in an urge to get out and about and take it to the next level, so I have been much more adventurous and social in my activities these last 15 years or so.

- Diane