When did you first crossdress?

[Xandra]

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?

[~Joanne~]

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.

[Vanessa5]

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

[artofbalance]

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.

[I Am Paula]

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

[kimdl93]

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

[Stephanie47]

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????

[Michaelasfun]

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

[RADER]

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

[vikki2020]

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

[Charlotte Haynes]

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...

[Ariamythe]

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.

[Phoebe]

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.

[Cheryl T]

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

[Wendy G]

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.

[Joslin]

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

[sarahgrant]

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

[Deborah J.]

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.

[FeminineEmoBoy]

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

[Robyn2006]

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:

[FrozenShiela]

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!

[Amelia_Barry76]

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

[JadeEmber]

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.

[S. Lisa Smith]

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!!

[Jenny Gurl]

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.

[Eddie]

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.

[Sylvermane]

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.

[Alisa]

Here is an earlier post on this subject.

http://www.crossdressers.com/forums/showthread.php?13736-When-was-your-first-time-with-makeup&p=2409283&highlight=#post2409283

[kellylynn_31]

9 or 10 years old, moms panties

[Andinera]

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.

[TeresaL]

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

[Georgina]

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.

[stacycoral]

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.

[Luna Nyx]

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.

[outhiking]

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.

[ArleneRaquel]

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.

[MeganHenry]

Between the ages of 8-10...

[Teddie]

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:

[Raychel]

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

[ChelseaErtel]

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.

[JuLo]

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!

[Ms. Laura]

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. :)

[CONSUELO]

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.

[Dena]

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!

[Ninotchka]

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.

[Jilmac]

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.

[Jolene]

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 ..... :)

[VikkiDave]

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.

[Beverley Sims]

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.

[Diane Smith]

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

[Chiana]

Like many here. Very early 3 or 4 yo at the latest. I had no idea there was anything wrong with it. I clearly remember the first time I realized that being a "girl" really wasn't OK. When I was 5, I told my Mom "When I grow up, I want to be just like Beverly". Beverly was an older girl that lived across the street. The look my Mom gave me set off alarms.

[Aylineira]

Earliest memory of myself crossdressing was putting on high heels and boots when I was extremely young. Definitely around age 5 or 6.

[kimberlybates]

I believe I was about 11-12 when I first slipped into a lovely blue long nightgown that belonged to my Aunt. I was hooked at that point.

[Melanie Sykes]

I never had any sisters, but I remember a day that one of my mum's friends' daughters was over, and she was a similar age to me. We must have been about 4 or 5 and she had on these black patent Mary Jane shoes. I could hardly take my eyes off them and really wanted a pair, although I had no idea why. I also remember when my beautiful Aunt Steph used to come over and, although very young, I was quite taken with how beautiful her legs looked with her nude tights and shoes. Then I remember getting out of the bath once when I was about 6 and my parents were both downstairs. There was a pair of tights and a skirt on the floor of their bedroom. As I was only wearing a towel, it was easy for me to try on the tights and then the skirt - I was genuinely curious as to how they felt. Of course, I was hooked.

[jackie_p]

Around 8 years old. I tried on my sisters Cheerleader outfit. Been hooked even since.

[BLUE ORCHID]

Hi Alexs, Some where around age five 65 years ago .

[Julie Denier]

Clomped around in Mom's shoes when I was very young, maybe age 5 or earlier. Explored other parts of Mom's wardrobe periodically through high school. Never dressed fully until about 2 years ago.

[lynnmcarthur]

I was 3 or 4 when I first remember being sure that I knew that being a girl would have been better for me

[Lorna]

I didn't have a sister or brother. Girls were of no interest to me until, aged around 12 or 13 (1957) I began to notice some girls about my age who waited on the same station platform. One or two of them had started wearing nylon stockings - as did the older girls. All the schools were single-sex so I had only a few minutes each day to observe the girls and was fascinated by their legs, wondering what it must be like to wear stockings. I also wondered how they held them up. I knew my mother wore girdles but I had no idea if these younger girls did likewise. I didn't know any girls well enough to ask. After a while I decided to borrow a pair of my mother's stockings and try them. It was a pleasant experience but, with nothing to hold them, it clearly wasn't exactly how the girls wore them. So, I managed to find an old girdle which I don't think my mother wore any more and put it on. It wasn't a very tight fit and I remember wearing a leather belt round my waist to keep the girdle from slipping down. At that stage I wasn't interested in bras or slips but I did try on one of my mother's summer skirts and loved the way it felt to have my legs in nylons held up by suspenders and shrouded by a loose, swinging skirt.

[dyane]

Must have been when I was about 13, Got interested in girls and what they were like under their clothes, so I 'borrowed' my sisters day of the week panties. Each day was printed on them. Mom's bras, girdles, nylons and dresses soon followed. Been dressing ever since

[Vanessa Amber420]

When I was 8 I tried on my cousins panties. I remember liking how the felt on me and the way they looked on me.

[Emma Beth]

I think the first time I tried on women's clothing is when I was a preteen going through my mothers drawer. The most significant memory was when I was in the military. It was a bachelor party gag for one of my best friends. My girl friend got with her boss at the strip club and we put together something I could do on stage. The other dancers worked with me for weeks to put together the most convincing performance. When all was said and done, it is a very fond memory; and I think I made about six hundred dollars in tips that night and my friend had the shock of his life.

[Nichola]

I was 6 years old playing mums & dads with my sister when she suggested I be the mum. She helped me into one of her skirts & I knew right away I was different. It felt so right to me & the feeling of being feminine was overwhelming. I'd lay awake at night wishing I was a girl & it became my deepest secret. I didn't think anybody would understand.
So I grew up the normal little boy my parents expected me to be, but in secret I'd dress whenever I could. I was fascinated by clothes & makeup & I adored the way it made me feel, just getting to be like a girl even for the shortest period of time.
It just snowballed from there, I'm 38 years old now & just a 'normal' guy to those who know me but I still love to do this, I feel like I need to.

[Angela Campbell]

I can remember way back when I was no older than 4, trying on my mothers things. I also remember when in the bath I would take washcloths and lay down and use them as clothes, laying one across my bottom as if they were panties, and one across my top as a bra, then one over these as a slip, then another as a shirt and then a skirt, Somehow even then I knew that women dressed in layers that boys just didn't do, and I wanted to do that. For the rest of my life whenever I saw any female I always noticed how they dressed and carried themselves. So jealous that they got to look like that and I didn't.

[Rhonda Darling]

I remember somewhere before age 6 stuffing a couple of small towels into my shirt as mock boobs. Shortly thereafter I discovered the dirty clothes bin, and all of mom's silky underwear, bras, girdles, slips, etc. I'd raid the bin while supposedly going to the bathroom and try everything on. It was heaven. I played dress up with the neighborhood girls in a playhouse one of them had. As I grew up, I found many times when I could secretly dress for short periods of time. That was done more for the sensation of wearing frilly things -- a great sensation for a pre-pubescent boy. In jr. and sr. high I gravitated to the school theater department and the world of dress up clothing expanded exponentially. It was on to the "second star to the right and straight on 'til morning" after that.

[Adrienna]

I first got the taste of dressing when I was apprx. 4 or 5 years old. Just out of curiosity I suppose I got into my mother's stuff, can't remember where, and tried a few things on. Been hooked off and on ever since. I always thought it a strange thing too until I realized that I'm in good company here. Funny what one remembers over the years. I also developed a heavy boot fetish along with leather and pvc clothing as well. Dipped into the world of femdom off and on dressed as a dominatrix which was/is a total thrill to me. Go figure the tangents to all this but all good and fun!

[Angela Campbell]

I am not sure but I think it was when I was 3 days old and my mom washed one of my diapers with one of her red shirts and I ended up in a pink diaper......

[Jessica Who]

I was about 6 or 7, tried on one of my mom's dresses when she wasn't home, felt perfect!

[trendiebrenda]

I was 4 or 5 when my mom dressed me in a pink party dress. It seemed like a natural thing to do at the time for me. I started dressing myself at 10 years old and never stopped...

[ghostrider503]

started when I was about 19 yrs old.

[aliciasoprano]

We have a celebrity visiting, Miss Jessica! Welcome..

[Xandra]

Thanks everyone for sharing your memories. A common thread running through most of our posts is the similarity of the experience of dressing at an early age and knowing at once that we had opened the door to another world.

[Nathalie Antoinette]

I was five and wore a dress of my mother's to play outside with a neighborhood girl. I know there were other times through childhood where I tried other clothes, heels, makeup and my mother's wig. I mostly left it behind in my teen years. After I was married, there was a handful of times I tried on my wife's things. I'm really now just thinking about it seriously and starting to experient a bit. It great to have all of these resources online!

[Annette Anderson]

Shortly thereafter I discovered the dirty clothes bin, and all of mom's silky underwear, bras, girdles, slips, etc. I'd raid the bin while supposedly going to the bathroom and try everything on. It was heaven.

Definitely been there,at age 9 or 10 i think

[sarahcsc]

Hm... around the same age of 7. I couldn't remember what I loved wearing at that time but I remember my mother dressing me up as a joke and I enjoyed it. ^_^

[Lacey New]

When did I first crossdress? Hmm good question. Maybe I'll answer like Bill Clinton - depends on what your definition of crossdressing is. Definitely in my early teen years, I developed a strong panty fetish and I borrowed my sister's and mother's nylon briefs whenever I could. I may have even put on a bra from time to time but all of these experiences were very quick with one goal in mind. I do remember though being fascinated with the small advertisements that were in the back pages of Penthouse and Hustler for a place called Michael Salem's TV boutique. So, curiosity was definitely there.

Then in college, a girlfriend left a pair of panties and pantyhose and I did not bother to return them until I had tried on both. I remember the feel of the pantyhose and it was - well, you all know - great. After that, my opportunities were few and it was not until I got out of college and I was living in an apartment on my own that I first bought my own lingerie. First just panties, then a bra and soon after, the whole range of lingerie inclusing garter belt, stockings, slips, camis, etc. I think at that point i had probably "crossed over" Even though I have purged many times since due to moves, marriage, kids, etc, I keep coming back.

[Denise1951]

My story is typical. I was 5 or 6. Started with my mothers slips and went from there. All my childhood, all I heard from her was. "I wanted a Girl." "I told the doctor to take you back, I wanted a girl." and statements like that. I was going thru home movies a few years ago, and found movies of me dressed up for Halloween. I don't remember it. When I got into high school, I decided to go buy my own cloths. Once I got over the fear of taking them to the checkout, I ended up with a nice collection. It was the mid sixties, and I discovered the "bra slip." I was hooked forever.

[kristinacd55]

My sister's full slip hanging and drying by the tub, when i was taking a bath. I was 6 or 7 and loved it! hook line and sinker

[NicoleScott]

I started around age 6 by putting on lipstick behind a locked bathroom door. It wasn't clothes, but I think that qualifies as a crossdresser activity. I didn't start putting on my sister's clothes until around age 10. Lucky for me, my sister and I were the same size (shoes included) throughout several teen years.

[Roberta_C]

At about age 13 or so I tried on a girls hockey skirt to see how I would look in it. Loved it! And that's where it started for me.

[Kari B]

Tried on my mums pantyhose when I was about 12 I think. Just to see what it was like. Took them straight off, but the seed was sewn. Always feel sexy and comfortable when wearing.

[Tammy Nowakowski]

Hmmmm, I think whan i can remember is when my got sick i was about 14 i tryed on one of her bras and a pair of panties both wear to big for me

then one day i went of over to my girl friends house she left her room for few mins i grab a pair of panties and a one her bras they fit just right

[michellecd9999]

I was told my baby sitter used to dress me up when I was under 1 yr old. But the first time I did it was around 12-13. Put on a nightgown.. one of those layered things of nylon and tricot. This would have been around 1969. I loved the feeling. Then moved on to slips, hose, pantyhose, panties, dresses, shoes, etc.
Did not dress fully in wig, makeup until I was in my 40's.

[Rachael Jones]

Must have been ten or eleven or so. Just vague memories of wondering what it felt like to wear tights, and the feeling of legs being free under a skirt. Fantastic, so it's carried on and off over the years.

[Danielle_cder]

Not soon enough... :) bout 5-6 aunts panty hose got me

[CynthiaD]

When I was three I begged my mother to wear nail polish. She painted my nails and I was in heaven. All the other kids in the neighborhood made fun of me, but I didn't care. A year or two later I begged my mother for a ribbon to wear in my hair. That was a bit disappointing, because my hair was too short, and it kept falling out. I don't remember all of the steps, but by the time I was in high school I was dressing fully, and thought of it as "just something I did."

Despite my early start, it took a long time for me to be really OK with it. I grew up in the 50s and the world was a very different place back then.

[MysticLady]

I remember trying a pair of mom's pantyhose that were hanging on the shower door left to dry and I was hooked.

[missmars]

nine . I tried moms bra.

[BillieJoEllen]

I had as a child been dressed in girl's clothes numerous times. I had always considered myself a girl/woman. I don't know if others saw that in me. I was never drawn to female clothes as a child. If I found myself in girl's clothes in any way shape or form I hardly gave it a second thought. Sometime around when I was nine or ten I started realizing that there really was a difference between boys and girls and I started coming to terms with the fact that we were 'different'. At about that time I got my clothes dirty while playing on my aunt's farm. She dressed me in my girl cousin's clothes. I was deeply embarrassed and humiliated. I continued after that to allow my mother to use me as a dress model for dresses she was making for a girl cousin although I was very sheepish about it. My mother encouraged me to use a costume for Halloween that she made for my older sister. That costume lead to conversations with girls in my fifth grade class and they encouraged me to 'experiment' with different girl's clothes. Up until then I could've stopped CDing and never look back although I still had very deep feelings of being a girl. When I was encouraged to try a certain combination of girl's clothes I was 'hooked' and I knew there would be no turning back. Although I don't think what I had experienced before was really CDing I think at that point is when I really became a CDer.

[Aylineira]

Definitely around 5 years old. I put on my mom's red heels and pranced around in them.

[Christinedreamer]

I am currently visiting my older sister and I asked her what her recollections about my early dressing were. She said the first she remembered was when I was about four years old and discovered my oldest sister's new pink babydoll PJs. This was around 1957. She tells me I would get them out of the drawer and wear them around and loved to take a nap in them. Mom was not too keen on this but didn't throw a fit.
Then on Christmas, my grandmother gifted both my sisters with new, really cute babydoll sets. My older sister got a lime green double layer set with double layer bubble panties and my oldest sister got a fire engine red set. My grandmother though had not looked carefully at the red set. They were one layer and quite sheer. Obviously my sister could not wear them around the house and so she buried them in her dresser drawer under the more traditional stuff. I discovered them and as they fit me perfectly, I snuck them into MY dresser. As with most every one else here, I was hooked on the feel of the material. My older sister was too shy to wear hers but did not hide them. One day she found me wearing the red set and teased me about it. She went to her room and got hers and said "here you can wear these too. I don't want them".
She goaded me into putting them on over the red set and I did. The thrill was electric!
Just then mom came in and was seriously pissed. My sister said she found me wearing them. Mom believed her and said I was going to wear them until dad got home and saw me in them.
When dad got home I was marched out for him to see. He just said " I see you like your sister's clothes. Want some of your own?" According to my sister, I just stood there. Mom said maybe I should wear them until I got tired of them and dad agreed. I do not remember much in the way of details now, but My sister tells me I wore them every day after school, the entire weekend, and slept in them for a month. Mom made me stay in bed naked while she washed them and then I had to get dressed in them again. Whenever I was with my family I was dressed in them. Pat says she thinks this went on for at least a full month, maybe longer. After that I found mom 's nylon nightgowns and really got started . They only took one picture of me dressed in them and I was sitting on the couch next to mom. We are looking for that picture now.

[CassandraSmith]

Three years old. Slipped into mom's girdle and jumped into bed. When she saw, she told me to take it off and put it back. It felt soooooo right though; I knew I was different then.

[becky77]

I think I was too young to remember, I have a vague memory of trying on my mums boots and could only have been about 5 maybe older? It feels like it has always been there so I have no real definitive start point?

[danielleinbr]

When I really think about it, I guess about 5 or 6 my mom had some really cool high heeled red boots. That is the first thing I remember. It started progressing slowly in my teens then went into overdrive in college.
Danielle

[ArleneRaquel]

Between the ages of 6 and 8, I don't remember what I wore the first time, but in one of the first I wore my mothers gloves, high heels, and jewelry. I have loved woman's fshion for almost 60 years.

[AlexisRaeMoon]

Does just sticking socks in your shirt count? Then 5 years old. But actual female articles? Probably 13. That's when I started being left home alone, and discovered mom's shoes fit. It was downhill from there!

[alexbowral]

At the age of 17 yrs I tried on a bra and panties, I have dabbled on and of for very many years, I have only been serious
over the last 12yrs. it came about after my wife passed away and I had to clear her cloths she was about my size so I tried some on , and from then on I nave become rather obsessed and now buy cloths that I rearly suit me.Mature maybe but thats fine.

[Tara D. Rose]

My earliest recollections are from around 3 or 4 years old. Though I had to hide it,it was so natural for me.

[Xandra]

Thanks to all for responding - I've really enjoyed reading everyone's recollections. It's curious that what started at an early age just doesn't go away.

[SarahMarie42]

When I was three or four years old, I used to beg my mother to buy me dancers' dresses and tights and shoes. I didn't quite get the shoes or too many dresses, but I'd occasionally get the tights and a skirt or something -- I would become implacable if I couldn't have them. Lol.

[May(be)]

When I was 6 or 7 I was running around the house in my mom's nightgown, shoes, and earrings and I didn't think anything of it. My mom had to remind me of that memory. I had totally forgotten until she told me about it when I talked to her about my crossdressing.

[Leighcdmd]

The earliest that I can remember was dressing in my mother's slip at about age 8. Supressed it during high school and college but reemerged in my twenties.

[Claire Cook]

Thanks to all for responding - I've really enjoyed reading everyone's recollections. It's curious that what started at an early age just doesn't go away.

No, it doesn't, does it? That's why it is so great when we just accept it -- and enjoy it.

[phlover]

Thanks to all for responding - I've really enjoyed reading everyone's recollections. It's curious that what started at an early age just doesn't go away.

I agree.
My crossdressing started when I got the stockings of my friend's mom at around 10 or 11.
They were really sheer as if I wore nothing on my legs, and the feeling was really fantastic.
My wearing stockings moved to wearing thigh-highs, and then pantyhose.
I became really enamored of pantyhose after lycra was used for pantyhose and I was hooked to the tight feeling of the pantyhose.
Later, my crossdressing developed into wearing girdles, shapers, short mini-skirts and high-heels.

Several times I tried to purge my feminine clothes and heels and resolved not to wear girly clothes anymore.
But the urge returned one after another, and I couldn't shake the desire away.
I finally compromised with my urge to crossdress, and it develops into deeper stages as time goes by.
I recently began to shave my pubic area and tuck using sports tape, and I don't know where my crossdressing would go further.
Maybe makeup and wigs and so on....

I am typing this reply wearing nude pantyhose, mini denim skirt and grey stilettos with 4.5" heels.
I LOVE the feeling!

[Nikki50/50]

Many variables, here.
Crossdress without acknowledging that it was 'different'? Without knowing even?
Or willingly pulling on the stockings, skirt, bra, etc...knowing full well that such was
considered a deviant behavior by most social standards?

Fist time was 6 or so. Summer dress to be a gift for my cousin, but the hem needed to be taken in so the dress would fit her. I got to be the manequin model for a few hours.
I remember that it felt...not quite right, but not wrong, exactly either. I didn't question it, I saw the need and accepted it. Besides, I was paid for my time by a huge sack of swedish fish by my Granny.

When did I willingly and knowingly dress the part of my female side? THAT is an epic stroy yet to be told. I am awaiting permission from the moderators to tell it.

[Diedre]

It was the mid 60's, I was 10, and my mother used me as her wig stand to comb out and style the short haired wig she had. I hated doing it.

But she also took in laundry and did sewing and alterations. So when I was 12 I got used as the dress model and protested each time, but I secretly started liking it.

In the name to get the job done and make money , my mom thought nothing of having me wear a stuffed bra. Or sometimes a girdle and nylons to make the shoes fit better when doing the hem. I enjoyed every bit of it.

However, I started showing too much interest in the part ( shaved the fuzz off my legs and would stay in the lingerie a little too long after finishing the fitting) and it came to an abrupt halt. One day mom showed up with a dress form from a second hand store and I was done. No more dressing, at least not that she knew about.

[Christie ann]

I have been cross dressing or wishing I could cross dress ever since I can remember

[katlee]

I didnt start crossdressing until I got a GF, but prior I would sometimes tuck when I got an urge similar to the stories I would read at ss.

[FoxxxyBri]

I was about 7 years old and my Mom put a little girl's dress on me as a joke. I have no idea if that influenced me or not. But at the age of 12 I put on her stockings before I masturbated the first time. After that I slowly turned into Brianna...

[Sarah V]

Putting on me mums pantyhose that she would hang in the bathroom after taking them off. I was around 6 ys old at the time. Shortly therafter I tried on one of my sisters body suits. That was it, I've been hooked on womens clothing ever since. (Sorry Nancy Reagan, I could just never say "No" to ladies things!!)

[adrienner99]

I was 8 or 10 when I started to pretend to be sick and stay home from school. My mom didn't work but she'd often go out and I would have time to dress..I believe the first outfit of hers I tried on was a yellow silk evening dress with a bow in the back. She also had a champagne cocktail dress I would wear with a petticoat. I wore her black patent three-inch heels (way too big) and her clip on diamond earrings. Then I would sit at her vanity and put on her Revlon's Cherries in the Snow lipstick. Sometimes I would put on her short, white gloves...Even today it is hard to describe how blissfully happy, peaceful and excited I felt. I also pored over her women's magazines, particularly the shoe and lipstick ads....Ladies Home Journal, McCalls and Redbook...now of course I like Vogue, Elle, Allure, InStyle, Glamour...

[Lacyfem]

My first time dressing was when I was 10 in my mom's panty, bra, hose and heels and it was also the first time I tasted alcohol and got drunk. Parents had a cocktail party before going out to dinner with friends and as soon as they were out of the house I started to try my Dad's bourbon. As I got tipsy something clicked in my mind and I went to the hamper and put on Mom's full cut nylon panties and bra, pulled out some nylons and slipped into a pair of her heels. It was a feeling that I can remember till this day. I so enjoyed being dressed and walking around our yard in the evening feeling fem but very drunk and excited. I ended the evening throwing up from the booze which wasn't fun and my mom knew about that the next morning but don't think she knew I was in her lingerie and nor did she for the rest of my years at home till I went to college.

[Kalista Jameson]

When did I first crossdress?

Last week. I was actually looking for a World of Warcraft PvP guide for my Blood Elf Rogue, redirected here and got inspired.

Lol, joking. Bad humor...

The first time I remember was playing with my sister, three years younger than me, I was around ten or eleven, and putting on her ballet tights and leotard so we could be super heroes. I stuffed a pillow case down the back of the neck for extra effect. Then I discovered pantyhose....

Life has never been the same. I blame the Super Friends for this.

Cheers,

Kalista

[Buxom Fella]

On purpose?

Twelve or thirteen, don't remember exactly when. I know I was 14 the first time I went out like that.

[Xandra]

Many variables, here.
Crossdress without acknowledging that it was 'different'? Without knowing even?
Or willingly pulling on the stockings, skirt, bra, etc...knowing full well that such was
considered a deviant behavior by most social standards?

Fist time was 6 or so. Summer dress to be a gift for my cousin, but the hem needed to be taken in so the dress would fit her. I got to be the manequin model for a few hours.
I remember that it felt...not quite right, but not wrong, exactly either. I didn't question it, I saw the need and accepted it. Besides, I was paid for my time by a huge sack of swedish fish by my Granny.

When did I willingly and knowingly dress the part of my female side? THAT is an epic stroy yet to be told. I am awaiting permission from the moderators to tell it.

I hope you get permission to tell your story; I'd love to hear it.

[CarmenSkye]

I first tried on my cousins dress when I was 7, but I didn't fully dress until about a year ago.

[savvy_fudge]

There's a photo of me, about 5 or 6 wearing my mom's one piece swimsuit. In my early teens I used to be jealous of the girls I knew and wondering what it was like if I was born female. Then in high school I started wearing my sister's clothes and experimenting with hers and mom's makeup. And thus Savannah was born.

Cheers.

[Nikki50/50]

I hope you get permission to tell your story; I'd love to hear it.

I hope so too...I approached the moderators about it, and I was asked to private message the first draft to get the OK...but every which way I try to encapsulate it, it ends up being damn close to novel-length. Still whittling it down...

[Julia Stevens]

I tried on my sisters black high heeled boots (she was 9 years older than me, they were up to the top of my thighs!) when I was about 8. I used to put her bangles over my ears as earrings and carry her shoulder bag. She thought it was cute. Not long after in secret I tried on her engagement dress, which was also far too big for me. After that it went on to my mothers clothes, bras, lipstick etc (I loved my mothers lipstick), this was also in secret.

[Xandra]

Hi Nikki,

Any news on your story?

Alexandra.


Many variables, here.
Crossdress without acknowledging that it was 'different'? Without knowing even?
Or willingly pulling on the stockings, skirt, bra, etc...knowing full well that such was
considered a deviant behavior by most social standards?

Fist time was 6 or so. Summer dress to be a gift for my cousin, but the hem needed to be taken in so the dress would fit her. I got to be the manequin model for a few hours.
I remember that it felt...not quite right, but not wrong, exactly either. I didn't question it, I saw the need and accepted it. Besides, I was paid for my time by a huge sack of swedish fish by my Granny.

When did I willingly and knowingly dress the part of my female side? THAT is an epic stroy yet to be told. I am awaiting permission from the moderators to tell it.

[Julogden]

Probably 3 or so. My mom had an old net petticoat that she gave me to wear, and I wore it a lot and I also got into her makeup and tried to put it on whenever I got the chance. I also clumped around in her shoes a lot when I was very little.

I didn't try on other stuff of hers that I can remember until I was old enough to be left alone at home for a short time, probably 8 or 9. I remember the first time I tried on a pair of her nylons when I was way too small to fill them out, they were very baggy on me, but I still thought they looked great. I used to try on her nightgowns too. By age 11, I was too big to fit into her clothes, and I was very unhappy about growing so tall at such an early age.

Carol

[Stevie]

The first time I remember was in my teens trying on my moms boots, but disinterested really start until my college days and the temptation grew slowly from there.

[Helen 2]

In my case , Mom. in 1961, my sister died when I was 9, she 11. Tore my mother to pieces because it was her fault...she miss-diagnosed what was pneumonia as a slight cold, by the time my sis was diagnosed, it was too late. Mom spent weeks in a mental institution and was in bad shape for many months. About two years later, once day at home Mom asked me to dress in my sisters' clothing and I of course said no, which made Mom cry in huge, heart-wrenching sobs, so...very concerned form her mental state, I grudgingly said she could -and I loved it. Spent the day in a frilly dressy, training bra and one of mom's girdles to give me some shape - and I loved every minute of it...it was so different, so much a discovery so......natural.
Two weeks later, she asked me again and I did not argue. A couple weeks after that I asked her and she beamed with happiness. From then on, as long as we were alone, I could be Helen as much and as long as I wanted to.

[Nikki50/50]

Hi Nikki,

Any news on your story?

Alexandra.

It was suggested that I should tell it in fragments, over several posts. 'Chapters', if you will...
I am currently writing out my crossdressing origin/history in longhand, and as soon as I chop it into segments (and and spell-checking...and grammar checking...lol), I will begin typing and posting them. One every other day should do it. No worries, it is coming...

[JenniferMBlack]

I was 13 the first time. I found one of my sisters skirts in the hamper and had wondered what it felt like to wear a skirt for a long time,I figured it is now or never and put it on. After only a few minutes I thought it is not normal to be wearing boxer shorts with a skirt and went to find a pair of panties, then relised my boys shirt looked awful with the skirt so had to find a blouse. I was fortunate to have the house to myself for an hour or more every day at this time, so I got to dress up for an hour after school for at least an hour. But that wasn't enough for me I started wearing panties to school everyday as well.

[misstracy90]

When I was really little, don't remember exact year or age, I wore pantyhose at certain times at home. My parents didn't really think much of it. For a while I didn't do anything but as I got older I started wearing things that were my moms when she was not around.

[Xandra]

Great. Look forward to it.
It was suggested that I should tell it in fragments, over several posts. 'Chapters', if you will...
I am currently writing out my crossdressing origin/history in longhand, and as soon as I chop it into segments (and and spell-checking...and grammar checking...lol), I will begin typing and posting them. One every other day should do it. No worries, it is coming...

[alexbowral]

I first started about 17yrs.old never became realy serious until 14yrs ago and now realise what I should have been doing
CD for ever, now I am makeing up for those lost years, live alone so no holding back............

[cdxmatty]

I started very young around the age of 4 or 5. Was not a very pleasant memory I had been caught by my mother and her telling my father and me catching the beating of my life.

[jenni_xx]

I was around 5 years old. Visiting my Aunt/Uncle. Was in a bedroom, with my sister (2 years older than me) and two cousins (both girls, 3 and 4 years older than me). They dressed me up - skirt, blouse, clip-on earrings, and lipstick. Then they grabbed my hand, walked me out of the bedroom and into the living room where my mum, dad, aunt, and uncle were. My Dad went mad, I ran out of the room, back into the bedroom and took off all the clothes. My sister and cousins laughing their backsides off.

[crystalbath]

I first started when i was about 15 when i started and tried wearing my mums panties - was amazing haha

[Ericaxd]

I think I was about 11 or 12. Tried on my mother's shoes and they fit. Well, high heels and boys jeans didn't cut it, so one thing led to another...

[Ceri Anne]

I was about 12, put on one of my moms satin body suits, felt pretty sexy. It was green and white and fit pretty good. I tried things on occasionally but didnt start dressing til just over a year ago when something clicked and I went all in.

[Madilyn A.]

I started before starting 1st grade. By 3rd grade would also wear makeup. By 4th grade I was already getting pretty good with makeup and getting dressed in a hurry, lots of very close calls !!

[diane_burf]

I was 6 and just started first grade back then I was just fooling around in moms room while she was dressing for her and dad's evening out she was always a very stylish dresser and had a lot of very nice things. Well after they left and the baby sitter was there I thought I would go see what she had left in her bedroom mom I mean. I went in there while the sitter was busy on the phone and found mom had left her lingerie drawer open a bit and saw a pair of sheer nylon panties pink still my favorite color on top of what was in there took them into the bathroom and put them on wow talk about being hooked. I was to go to bed at 8 so I made a beeline for the bathroom and took of my cloths except for the panties and put on my jamies. I jumped into bed and the sitter came in and turned out the light slept with them on was my start,,,,, db

[CarolynO]

I remember putting on my sister's frilly dress, probably age 5 and was caught that very first time.

[MsMargaret]

I was a sickly kid. I missed a lot of school days, and got bored. I started with my sisters' clothes I found in the laundry room, and managed to dress up a lot when my mom wasn't home. I dressed up a lot in my room, but couldn't really have a stash there as I shared it with my brother. I used to wake up in the middle of the night and steal down to the laundry room and dress. My younger sister caught me once, and I kinda stopped for a couple years. I went through a few purges. Many years later, I live alone, so it's easier.

[AnitaFloridaGal]

My mother and older sister dressed me up in my sister's clothes starting at age 5. They made me go to a neighbor's birthday party for her daughter. I had to wear a little girl's sundress and sandals. My hair wasn't long enough to style yet, so they made me wear a cute little hat too. Even though all of the parents and kids at the party knew I was a boy, I really enjoyed pretending to be a girl. After that, I became known as the neighborhood sissy. I was constantly teased by the boys for being so effeminate and ended up playing with my sister and her friends most of the time.

That was just the start. Since I was small for my age, my mother made me wear my sister's hand-me-downs that were appropriate for a much younger girl than my age. Afterwards my mother insisted that I grow my hair long. She would take me and my sister with her to the beauty parlor to have it trimmed and styled. For my seventh birthday, she curled my hair and had my ears pierced.

I've been dressing as a female ever since. I live and work full-time as a woman now in an office with other women.

[Jocee]

Very distinctly remember - 5 years old, mom was in the hospital very sick and I was looking for comfort. Put on her pajama's and housecoat

[Xandra]

One thing really does lead to the other. I just wanted more.
I think I was about 11 or 12. Tried on my mother's shoes and they fit. Well, high heels and boys jeans didn't cut it, so one thing led to another...

[CuriousCurious]

I think my first article of clothing I ever wore was a jean skirt when I was like 11 or 12. Maybe 10. I can remember the moment to this day. I do remember enjoying it. :-)

[Kelly Smith]

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 first crossdressed about eight months ago. I had fantasized about for maybe six months before. It was delicious and I will not stop.

[Xandra]

Nor should you, Kelly :)
I first crossdressed about eight months ago. I had fantasized about for maybe six months before. It was delicious and I will not stop.

[Jay135]

Disclaimer- This is probably 85%-90% accurate...my memory may be a bit fuzzy here and there, but here goes anyway:

I think I may have "cross-dressed for the first time" (if you want to call it that) around the same time as most everyone else...around 13-14 (sometime around then, anyway), finding a box of fake nails in my mom's closet and trying them on (they were the stick on tab type, not glue-on...I hate those useless not-so-sticky tabs to this day). I already had a "fetish" for long nails (I didn't understand at the time- that started around 9-10, but I "got it" eventually ;) ), and I "took pleasure in" wearing those nails (and others I eventually acquired), and painting my toes here and there throughout high school and college, until I got married (at 18)...I never dressed further than the long nails (and painted toes), and semi-suppressed it (read: didn't wear them as often) until only fairly recently...I started keeping my my toes painted 24/7 about 2 years ago...which slowly built up to also wearing pantyhose (with the long nails- only for "fun time" ;) )...then on to panties. Then, mayhap a little over a year ago, I found my first pair of heels that fit me at a thrift store, and bought them. From then, my dressing en femme seemed to grow exponentially as I finally made a decision to start exploring this side of me more, until I dressed 100% (and got busted by my SO soon thereafter ;) )...around 6 months ago...and went out dressed in public about a month or so afterwards (in my eyes, it literally exploded in a few short months from a simple fetish to...everything).

If I were to go back in time...even mayhap a year ago, and tell myself that I would be dressing completely en femme and going to all these fabulous places with all sorts of wonderful new friends, I would have laughed in my face, called me crazy, and went back to my game. Who's crazy now, hon ;) ?

I keep telling people I'm still new to all this...still exploring, understanding, etc., but it seems nobody believes me...

[libbyb]

My first memory I was about 5 was trying on my moms long leg panty girdle that was hanging in the bathroom. I had seeas n it many times and was always touching out when I could finally put it on in the house was just me and mom and my 2 sisters I did not know I could stand to per until I went to school and saw the other boys do that.

As I got older I dressed more and more. Finding my moms copy of the sensual woman I read that as much as I could. When I went off to college I lived I. The dorm for the first year a.d then saw an add for a room for rent so called the last was tryin.g to make ends meet and was close to school so I decided to rent the room after ni ING in I put some of my extra things in the attic there I found a trunk filled with bras girdles stockings slips almost anything you could dream of.
One day she walked in on me Freddie.g in the items from the trunk. And said I knew you were a bit different she ended up helping me dress fullly doing my make up and getting a wig for me. Ikmi felt so pretty and femine and that was the beging of my journey.

[lisa_cd]

Early Memories...
I was probably around seven years old when I had my first thoughts/feelings about cross-dressing. I can remember laying on my mom's bed and thumbing through her department store catalogs (JC Pennys, Sears, ect.) and being amazed at all the different styles and types of women's undergarments and clothing. Soon after I tried on a pair of mom's panties which were hanging on the towel rack in the bathroom, which seemed so right to me. I can't even begin to remember how many times I did that...as often as possible I suppose.
The thrill has never, ever left me!

[Joanne108]

Well I was 5 my brother and I were playing some game, and for some reason I had to be the girl. So I was. Then my brother goes away and came back from my mothers room with a bra and said something to the effect that since I was the girl I should were a bra. I thought nothing of if. Put it on. Put some of my sister doll pillows in the cups and like that I had boobs. That is all it took. Once I looked down at my chest and saw boobs, I thought this is great! I've been a CD ever since! Of course I found many ways to get 'tricked' into doing it again!

[socalcutie]

I don't remember exactly, but I remember being young, a little kid, trying on my mother in law's garments which she stored in my bedroom closet because me, being a kid, didn't need any closet space apparently. She didn't have anything I was in love with, but it was a long time ago.

[Taylor186]

Around age 5-6 I remember playing in my bedroom wearing a "dress" I had fashioned out of a beach towel. Does that count? At 7-8 I was trying on hosiery--some with exotic back-seams--that my mom left to dry on the shower curtain rod. At 8-9 I was wearing her girdle with the stockings. And, at 10-11 I found a one-piece skirted bathing suit in her bottom bureau drawer (like the one pictured below). I loved the way that strange elasticized bodice hugged me and the way the skirt flared off my hips. Had fun with that for several weeks until one day I looked for it and it was mysteriously missing. I was totally stealth, I thought, but maybe my mom suspected something. Nothing was ever said though.

[sophie_]

For me it was when I was around 8, when my Dad was working away and my sister was out, my mum sometimes let me dress me in my sisters school skirt after my bath and things just took off from there. I think she probably regrets introducing me to crossdressing now and she caught me numerous times while I was growing up but by then I had been well and truly bitten :D

It's never been mentioned since but knowing Mothers intuition I'm guessing she has known all along that I was still doing it in private. :battingeyelashes:

[olivia.tanner]

i think i first actually dressed when i was 10 or 11, i would wear my moms red silk nightgown that looked sexy as hell to me at least, i wore it with black thigh highs and a pair of white heals, i felt so beautiful that i was for ever hooked. when i was much younger than that i would walk around in my moms heals but that was just me being silly but i think i subconsciously new something was so right with wearing those shoes.

[FelicityMay]

played a game with my cousins around 10 or 11 called gender wars!
we each dressed up as each other and just had fun with it, but i had a little too much fun and got really into it!

[DaniG]

Yesterday!

I never knew I was transgendered until December 2012. And my wife hasn't been ready for crossdressing, so we've been sticking to easy stuff like painting nails, shaving legs, and makeup (yeah, go figure). But last week I spotted a gorgeous blue tunic on sale I just couldn't pass up. It arrived yesterday morning before work. My wife came upstairs as I was trying it on.

"How do you like it?" she asked.
"I love it! I can't believe it fits!"
"Well, I guess that answers that question," she said.
"What's that?"
"You like women's clothes."

I thought that would have been assumed, given that I'm transgendered, and all the other stuff that's been going on (TMI), but I guess she still had held out hope that I'd hate it. No such luck. She needed a hug.

It was euphoric - *intensely* affirming of my femininity. Must - have - more!

[AlisonHell]

I first wore female clothes when I was 14, a friend from over the road left a gym skirt at our house after a fancy dress party at school.

I had done the usual dressing up as a small child in family and friends outer clothes and thought nothing of it.

But this one time I was very aroused by the idea, and went for it as I was alone. WOW it blew my mind and as I was a lone for quite a few hours it ended as my first W&$k.

I have stolen a lot of underwear from friends mums and sisters in the past, I know this is very vain but it was only from the very pretty females. I have now just bought a full wardrobe of my own, and am bursting (literally) to try mine on as they arrive.

I had a girlfriend/ Fiancée from the past who used to taught me by saying she wanted me to wear her undies. She never knew my past.

One night we were both very drunk and she said put the underwear on! I thought she meant me, but I now think/ know for sure she meant I put it on her. When she saw me in her undies she was visibly shocked.

This was the end of our relationship.

I continued to steal underwear every now and a gain, and have not been caught thank god. I don't know how I would have explained it. People need to know this was early 80's to late 90's.

I enjoy the feel and texture against my flesh, it gives me a massive sexual boost when in the mood to wear it.

I'm currently wearing a lacy bodystocking under my pajamas, the pajamas are only because of the cold outside.

When the weather picks up I have Stockings and suspender belt, black lace corset and a very sexy cocktail dress (strapless). I'm just waiting for my sexy panties and high heels to arrive.

Even in the cold weather if they arrive soon I will have a great private party for me! LOL.

Alison.

[HelenR2]

My Mother's stockings, when I was about six, but my favourite item of hers was a one piece bikini that I used to wear in my teens. I would put it on under my jeans and T-shirt. It was tight at the crotch and had plastic breast cups so I lost my bulge and got boobs at the same time. I guess that is what I am still after today, boobs and no bulge.

[rickyjoe1978]

I remember bout 6 I relized how women cloths felt and could stop after that...lol

[Janie {3]

Four years old. Loved it ever since.

[Angela Campbell]

I don't remember exactly, but I remember being young, a little kid, trying on my mother in law's garments which she stored in my bedroom closet because me, being a kid, didn't need any closet space apparently. She didn't have anything I was in love with, but it was a long time ago.

Wow! You must have married quite young.

[AmandaBlack]

Like many here...in mom's pantyhose from the drying rack at probably 12 or so. They felt incredible on me and aroused me instantly! I then recall venturing into her closet and dresser and wearing high heeled boots of hers with the hose and nothing else. I can remember looking at my slender bare body in the hallway mirror with the hose pulled up over my nipples and feeling so sexy!

I suppressed or let it go as I got into my later teens until about 21 or so, just after getting married. Jokingly, one afternoon my wife said to me, "You'd probably look ok dressed as a girl" or something to that effect. It immediately rekindled the flame!

She likes to wear sexy things and we were quite young at the time...she had lots of sexy outfits and lingerie (still does :)). Not long after her saying that to me, she was out of town for a weekend and I slipped on a pair of her thigh highs...soon I was in a bustier and trying my hand at make up and lip stick. It was thrilling and arousing!

I spent the weekend in our bedroom dressing and decided I would surprise her when she came home...playing off of what she had said. Now, part of me felt a little strange..."What the heck are you doing?!" This was early 1991 and we didn't even have the internet then! I thought I was the only "freak" who dressed! lol.
I got scared she might not like what she saw, freak out etc. I decided, no way! I'm not going through with this and got out of her things and told myself "Never again!"

Haaaaaaaaaaaaaaaa Haaaaaaaaaaaaaaa

[cuis]

I don't actually remember the 1st time, i think i was like 12 maybe, but wanted to do it since i was like 7

[mexdresser]

I was around 6 years old... can't recall if the babysitter started me off, or if I did, but either way, I was pretty young but knew I'd never stop from the first time I wore womens clothes.

[Anacita]

I must have been 6-12. I stole my mom's (old school!) pantyhose and wore them under my PJs with heavy wool socks. Had to have aroused suspicions, but we did NOT talk about these things...

[Kiltie]

I suppose I was lucky in that here in Scotland boys were expected to wear kilts from a very young age. I had my first kilt made for me at age 6. I dont recall too much about it but I do remember liking the feeling of not being trussed up in short trousers and underpants, which for boys then were always white and had buttons on the front. The answer then was for boys to wear girls school knickers and as my kilt was green based tartan I was given a pair of dark green knickers. This continued for a number of years and my mum liked me to wear a kilt to parties and to church and also I often wore a kilt to school and on any other dressed ocassion. I had a green tartan kilt and also a red Royal Stewart tartan kilt so my mum would always ensure I had the correct colour of knickers under the kilts. I remember at the age of about 9 or 10 realising that I envied the girls so much when I used to see their skirts or their girl kilts swinging and sometimes being blown up by the wind. At that point a kilt was the ideal answer for me as it is to this day. I did however start to actually crossdress in my early 20's when I got very curious and had a desire to feel what womens clothes really felt like. With a very red face I forced myself to buy a grey skirt, some white ladies knickers and a white blouse. Stockings and suspenders were a problem but I managed to pickup some in a department store and take them to the till in the hope they would fit! I couldnt wait to get the house to myself and get dressed and it felt fantastic when I did. I didnt have shoes at that point and I remember feeling that I just wanted to have boobs as well. I wracked my brains and as the blouse was quite generous I got 2 balloons and blew them up to the same size, stuffed them into my blouse and felt absolutely great. All a bit haphazard but thats where it all started for me. If I want to dress nowadays obviously I have the correct items of clothing and still enjoy it.

[MissJoanne]

First recollection I have of doing it "fully" would be at age 12. I'm now 55 and more into it than ever. I feel "freer" than I have in a long time.

[Rachel Murphy]

At age 6 or 7 my mother made my sister a dress. I liked it so much I made a fuss until she made one for me.

BTW, she (my mother) took a picture of me in the dress and didn't mind showing to anyone for many, many years. Ouch!

[Phanatic]

I think I was like 4 or something, pretty young, I think my mum and sister dressed me up in stockings and makeup etc. I liked it, but not when I got laughed at so left it alone for quite a while. Started dressing when I was a teenager at some point, worried about getting caught, purged. Now coming to terms with this other side of me and trying to enjoy it and let the benefits seep into other areas of life.

[Lorri_c]

I think I was about ten, I tried on my sisters dress while my family were out. I was way to big as my sisters are younger, when they got back my sister somehow choose the same dress to try on and accused me of trying it on which I denied absolutely (could she smell me??).

[marelna]

Around the age of 5, was always fascinated when watching my Mum do her make up and getting dressed. Tried one of her dresses and lipsticks.....have never looked back!!

[Becky Adams]

Around 1947 when I was 8. Neighborhood women were making dresses for a wedding (my mother was not there) and one woman suggested I might look cute dressed as the flower girl--they did and as one said when I was dresses I "was too cute to be a boy." That was it!

[DeidraDee63]

I started to explore around age three or four that continued into my teens to various degrees. I then went through a period of time where it was all mental and actural dressing would release the stress. I was in my mid twenties when I had access to full wig and makeup and when I first really saw Deidra as a reality and it scared me but I liked it, then went into denial, purge the whole nine yards which did not work. This continues to this day but only now am I understanding it, I now embrace it and what I thought was a curse is really a blessing. Where it will lead I do not know but I plan to enjoy the trip.

[lona]

I was 5 years old my sisters dressed me up big joke for evreone but I was hooked

[shayleetv]

I was crossdressed by my mom as a baby and off and on until my third birthday(no recollection) when my dad took me to get my first hair cut, a buzz cut at that. My sister used to play dress up with me because she had no other girls to play with in our neighborhood. She would put a scarf around my head because I was still sporting a buzz cut. When I became a Cub Scout they had skits at every pack meeting. One time a friend from another den was dressed completely like a woman, wig makeup, nylons and high heels for for a skit he was in. My mom being a competitor made me up as a girl all the way too the next skit I was in. And so it went all the time I was a Cub Scout. The time I remembered most was and the time I really felt girly was when the Scout District decided to have a skit contest between the Cub Packs. I think I was 10 Jery and I had girl parts and were dressed to the nines. In the morning there was a run through so everyone would know what to expect on the stage and the in the afternoon we would put on the skits with the top six skits competing in the evening. We weren't dressed in the morning but were dressed for the afternoon. As luck would have it we were to compete in the evening as well. Jery's mom didn't want to dress him a second time so we stayed dressed and our mom's took their "daughters" out to eat. I was feeling so girly at that time I could hardly stand it. Being treated like a girl by all those around me including my mom. We even used the ladies room. I think before that evening dressing was nothing but after that it was really something and I couldn't get enough of dressing. That is when I started to dress on my own, mostly in my sisters clothes and bras.

[Geena75]

I first tried on my older sister's pantyhose at around age 12 -- loved it but ran from it.

When my folks ran a big rumage sale one summer, I found that little purple short dress with the white lace in the front. I put on the pantyhose, and used a wire to zip the dress up. Loved looking at my legs in a mirror. Terrified I would get caught.

First crossdressed, knowing I was actually doing it -- Monday.

[Mikaylagirl]

Many variables, here.
Crossdress without acknowledging that it was 'different'? Without knowing even?
Or willingly pulling on the stockings, skirt, bra, etc...knowing full well that such was
considered a deviant behavior by most social standards?

Fist time was 6 or so. Summer dress to be a gift for my cousin, but the hem needed to be taken in so the dress would fit her. I got to be the manequin model for a few hours.
I remember that it felt...not quite right, but not wrong, exactly either. I didn't question it, I saw the need and accepted it. Besides, I was paid for my time by a huge sack of swedish fish by my Granny.

When did I willingly and knowingly dress the part of my female side? THAT is an epic stroy yet to be told. I am awaiting permission from the moderators to tell it.

Oooh...whisper it to me ;>P

[Mikaylagirl]

For me,the first time unknowingly I was about 6 years old. My family was visiting some of their friends and I was in my friends room playing some game with her. Before I knew it I was in one of her dresses. I remember feeling like "hope my parents don't see this because this feels great"!
As life went on I was in my ealry teens and had an older cousin I used to run around with. She would always let me try on her newest micro mini disco dress and heels. I always had super long natural hair growing up,and while she let me dress she always braided my hair into a really cute ponytail. When no one else was at home she would let me dress up and be about the house all day and night. She knew I was becoming more feminine and she totally stood by it and we had great fun with it. Eventually I got a gf and by my early 20's we were living together. I expressed to her that I wanted to try on her lingerie and she was very cool with it even after we broke up,till this day she has kept it a secret to our mutual friends.
I started dressing full time when I bought my own home and me and my gg start hanging out a lot more. used to love waking up en femme,laying out in bikini's (had 7 acres of private land),walking down the driveway in a spring dress n heels to get the mail. I miss that privacy so much.

[cdtraveler]

I was 6 and about to go on stage to sing at the high school for a holiday show and this well endowed teacher with her cleavage showing leans down and says wait honey you haven't had your stage makeup put on yet then proceeds to apply red lipstick. I can still smell her perfume and see her lace camisole. She then tells me how pretty I look and sends out on stage. On ride home I can still taste the lipstick. I'm mesmerized. Next day I'm standing in front of Mom's dresser reach for her lipstick apply it and well I've never lost the desire for feminine finery 45 plus years later.

[Nicolesmyth]

I was six when I dressed myself. At earlier age my sisters dressed me up.

[Xandra]

I was 6 and about to go on stage to sing at the high school for a holiday show and this well endowed teacher with her cleavage showing leans down and says wait honey you haven't had your stage makeup put on yet then proceeds to apply red lipstick. I can still smell her perfume and see her lace camisole. She then tells me how pretty I look and sends out on stage. On ride home I can still taste the lipstick. I'm mesmerized. Next day I'm standing in front of Mom's dresser reach for her lipstick apply it and well I've never lost the desire for feminine finery 45 plus years later.

What a lovely memory...

[confusedcder]

I was about 12, put on one of my moms satin body suits, felt pretty sexy. It was green and white and fit pretty good. I tried things on occasionally but didnt start dressing til just over a year ago when something clicked and I went all in. Sounds a similar story this as to me though unfortunatly I can't remember the particular item it was the lingerie body is what i remember and wore the most. She had a black and a white one she never wore the white one felt a little sticky on the skin the other when I first began seemed the perfect size silky and had kept it hid it wore other stuff looked online on teen clothes websites; those and back when the pair of high heels fitted me perfect are good memories. Washed the body in the bath or sink damn nostaliga good times.

[Nicky63]

The first time for me I was maybe 12 - 13 and I found an old blouse presumably belonged to my sister. I remember it was pretty wih lacy edges and I liked how it felt on me although I had no concept of cross dressing, it was just a bit of fun. It wasn't until my late teens I was staying at a freinds house his girlfreind had just left him and I found in his garden shed a bag full of her clothing, knickers bras etc. I just had no hesitation in trying them on and I've been hooked ever since.
Nicky
xx

[WantingtobeVictoria]

My first time was 2 years ago...I was in my 50's. It took a long time to have the nerve to bring it up to my wife...it started with asking to put on a pair of her panties

[Leanna Jean]

The first time I crossdressed I think I was four. My mom used me as a model to sew dresses for my cousins. She dressed me and then painted my nails and put lipstick on me. I then discovered my grandmother's closet. The next step was my mom's closet who had a wonder collection of evening gowns and my first wig. I was seventeen when my mom caught me in her panty drawer. She and a her gf dressed me in a prom dress with the works. They took me to dinner and dancing. I later had girlfriends who would beg me to cross dress and then I would give in. Little did they know! My wife supports me after my mom told her about my teenager dressing occasions.

[ReineD]

^ Seriously?
................

[iGenny]

Another late bloomer - VERY late. I'm in my mid-fifties, and it was about 1 1/2 years ago. I was getting dressed after a shower, wife was in the shower, we just had a fight, and I thought to myself I could be a better woman than she is. Put on her panties. Escalated from there over time.

[Samantha Horne]

Age 13. Removing washing from the line and I just had to feel that satin and lace against my skin. My sister always had friends around and there was no shortage of pretty things to choose from.

[Tracii G]

First time out fully presenting as a female I was 16.
My GF's down the street who made me up as a girl all the time coaxed me into going to the senior prom with them as a girl.I was a Junior at the time.
It was great fun and needless to say a giggle fest for us.
Boys asking us to dance all that stuff.I told them I went to a different school and my date didn't show up.
I got to dance with the captain of the football team and he got quite fresh with me too,kissed my neck and grabbed my butt a few times.
Word got out around school later the next year that I went as a girl and I had more than enough girls to hang out with.Guys didn't like me too much but I didn't care.
I was always with a pack of popular girls so the joke was on the guys LOL.

[lacy s]

I am guessing around 7 years old, stealing my moms silk panties. As I got older that progressed to lingerie and my sisters dresses. By the time I was a teenager, I had bought a few of my own items. Now I have a reasonable collection, although limited by the space I have to hide them. I think the best day was when I purchased heels and breast forms.

[Michelle K]

I was constantly being dressed in girls clothes from around age 6. I am the only grand-son out of 23 grand-children, They always liked playing dress-up and since I was out numbered they would doll me up in thier clothes. As I got in my teens my cousins had girl friends in other towns that they could get me to so that I could dress-up and go out with all the girls with out bumping into to many family memebers. Is tough when you grow up in small town Illinois farming communities cause everyone is related. LOL!!

Michelle K

[LSL_Dee]

I started with my sisters clothes when i 12ish. I do not remember exactly.
I went out dressed in college a few times and passed as a homely CO-ED but stuffed the desire for a while
I started dressing full time after my 1st divorce. purged and got remarried. Got caught dresseing in wifes clothes and she wanted to have me forcabl commited and drugged. Needles to say she is Ex #2.
Current wife has recently encouraged me to dress and go out. Even suggested I find a boy friend. She is a keeper.

[StephanieH]

This REALLY needs to be a sticky! Once again, 4th grade - won the boy's beauty pageant - things were never the same again!

[stephyX]

all started for me at 14, mostly my sisters clothes as we both were similar size,now as ive got more confident with it im glad i started when i did and not too much later :)

[ossian]

Ok, I saw this and had to reply, for me it started when I was thirteen. It was a rather confusing time, I felt the need a few of my mother's things on and it was an electrifying experience, and oddly enough I felt normal. Of course, this was mixed with heavy doses of confusion and of me wanting to desperately be a girl. That lasted for a few years until I got use to being what I didn't know at the time was bi gendered. But I still remember those early times like it was yesterday. It is just amazing which memories stick around. :-)

[Sabrina133]

i've always been fascinated by women's clothing for as long as i can remember - especially hose and shoes. I think the first time i ventured dressed as a female character was when i was 11 or 12 - i dressed as a witch for halloween. A few months later, i was in our bathroom and found one of my sister's skirt and blouse set. Just had to try it on. I remember it was made of some synthetic fabric that was soft and had a shine to it. The sleeves were tight all the way down, the skirt short and fit me like a glove. I looked in the mirror and loved the way it made me look. The thought of that outfit on me stayed with me from that time forward. A few weeks later, i was alone in the house - armed with fond memory - i decided to raid her closet. I found a short pleated gray wool skirt, a satin blouse, pantyhose and boots. We were the same size so everything fit perfectly. Over the next few months, i tried on pretty much everything she had - in secret of course. There was no doubt in my mind thats what i was supposed to wear. I was absolutly heartbroken when we moved (the bane of military life) and she decided to stay behind. She'd just graduated from high school and i'd just started. We had been living in NY and moved to PA. She stayed away for one year and so my dressing pretty much stopped. For some reason, i couldnt bring myself to try on my mom's stuff. It was so boring it just didnt seem right??????????? I was overjoyed when she decided to move back home. Best of all she brought back a whole new wardrobe. I picked up where i left off.

When i went off to college, i didnt dress for 4 years ... wow. the longest ever.

[Cheryl Ann Owens]

Some of it is still a fog and my memory isn't that great. But it was probably 1958 when I was 5 that I put on my grandmother's dress while she was my daycare at the time. I didn't get a thrill from it but somehow it felt right. I was probably 6 when I tried on my mother's girdle which was too big for me! LOL! My sisters and mother even painted my finger nails! Meanwhile my family humiliated and discouraged me from any other dressing. Then when I was about 11 I had an "ah-ha!" moment and "decided" I would love being a girl and being dressed. Devious little me raided my sisters drawers trying on their things and loving it! I was very careful to fold everything properly and put it back to avoid detection. (They probably knew!) Thinking back, was I pre-disposed to being a girl in my mind anyway?

Cheryl Ann

[Cheryl Ann Owens]

Part Two! (With joy and jubilation that I'm understood here!!!!!)

My first grade teacher in 1959 told me I had pretty blue eyes! (Translation to me---I should be a girl!) Actually my hair stylist told me to not use blue eye shadow and go for a rose color. WOO HOO!

When my sister got married, another sister was a bridesmaid and wasn't available when Mom tailored her dress. We were about the same size and I happend to be home. Guess who was the model! I didn't want to take off that gown! But...I had to...sigh.....

Cheryl Ann

[Rikidee]

Best I Remember I Was 5 Or 6 And Was Caught By My Mom Wearing Her One Piece Swim Suit Playing With My Brothers. Got The usual Threats And Learned To Hide Better. Progressed To Dressing Only When Parents Were Out Of The House And Trying On Clothes Every Time I Had The Chance. Hugs Riki!

[Leanne2]

Before i was old enough for school, about 3 I believe, I crawled under our front porch and put on a dress. I knew it was "wrong" so that is why I hid from my family under the porch. It took me 55 years to realize that I am transgendered and not a cd. Leanne

[spandexgirl188]

it was around six or seven. My mom put me in ballet so i started wearing tights at a young age. When puberty hit, the thrill of looking like a girl came into full bloom for me.

[shannon oeswicki]

My earliest memory was at 4 years old. I had a friend over, and for some reason I decided to go upstairs to try on pantyhose from my mom,s drawer. When I didn,t come back for awhile, my mom and friend came upstairs to find me. I still remember the look on my mother,s face when she saw me standing at the top of the stairs in pantyhose. For years after that, I was fasinated with pantyhose and would try them on any chance; I had. I eventually moved on to girdles, bras, lingerie... the whole nine yards. I really wish I knew what motivated me to start with this.

[SarahVA]

6-7 I guess, mom's dress....then alittle older 10ish a dress, bra and lipstick...fully at 13 with a female friend.

[Farrah]

I was about 4 or 5...I tried on slips and panties first....I thought it would go away. Boy was I wrong!!

[ninadiva]

I was in my early twenties when in a relationship at college with my then to be first wife. I found i liked the feel of her clothes against me when i was with her and then that progressed to experimenting with trying on when she was out. She never knew of my urges and after two years of marriage she moved on with some bstd she worked with. So naturally i built up my own modest little stash which i purged later when i got nervous of being found out by family.

[Sister Rachel]

Aged 2 or 3,pulled on a pair of my gran's panties, bounced around on the bed experiencing pleasure, and was discovered! Aged 7 or 8, found a way to turn my pyjama jacket into a skirt!

[Jaylyn]

I guess I can put the blame on my mom. When I was born she had wanted a girl real bad. Apparently she dressed me up as a girl in some of the little girls dresses she had already sewn together. My dad I'm told didn't like what she was dong and put a stop to it. I found out later that she didn't stop doing it behind his back till I was about three. Mom has an old picture of me in front of her old dresser and me playing in her makeup with the red lipstick all over my lips and face. I guess I wasn't coordinated enough do put it on right then and or now...lol Later in my childhood I started getting her old panty hose out of the trash that had all the runners in them and stored them in the top of the barn. I later secured an old girdle she discarded and I also had a good stash of Sears and Roebuck, and Montgomery Wards ( we called it Monkey Wards) catalogues stored there as well. I would set in the hose and girdle and stare at the girls in those catalogues and all the bras girdles and hosiery wanting to be like them. I then progressed to when my parents were gone I would get her slips out and play with all the gear on. Even advanced to some play lipstick that was chalk so it could wash off easily. I also did all the guy things in school football, Ag (FFA) and Track. I loved a course in Homemaking that explained how babies are made and taught us how to wash dishes and cook, and then how to dress up for an evening with our dates...I listened when the teacher taught the girls how to dress...deep down I wanted to participate with them but had to keep the macho thing going. I hid all my feelings and suppressed them till after college and I met a girl and married her. She said she knew that I had played with her clothes and she was right, as its hard having someone near and wearing hose and heels and you have to wear jeans and boots...We are still married but now she is helping me with the dressing part and she is learning my feminine side with me as I don't know where it will lead me. I just know I want it to be with my wife...
I am in love with this site and the many good gals here...

[ArleneRaquel]

Jaylyn,
Lipstick all over your face-YUMMY. Sears & Ward catalogues....the lingerie section, that brings back so many fond memories. HUGZ !

[Aly Cat]

Well, my earliest memory of doing it on my own was when I was 13. I would put on my sisters nightie and other stuff while brushing my teeth in the morning and getting ready for the day. No one knew. Before that though, I have faint memories of my older sisters dressing me up and painting my nails and stuff. I may have been 3? When I was 5, my sister and I wore my moms skirts up to our shoulders secured with a belt and trampled around the house with sand buckets on our heads handles for chinstraps. I think I even still have the picture! So I guess from the very getgo!

[Anacita]

I started dreaming about crossdressing at 5. Sometime between then and 13 I began wearing my mom's pantyhose (lol - such old-school pantyhose they were, too).

[Pam]

In my teens
My cousin' s panties and Gym Outfit
Then was dormant for some years
Again in my 20's and ever since

[LynnR]

When I was about 4 I used to play with my grandmother's lipsticks and mum's jewellery. But I remember when I was only about six begging a girl day after day to let me wear her clothes. To my delight, she finally said yes, but of course I soon got found out. After that, I wore my mum's bras and stockings and played with her make-up and when I was in my teens I took every single opportunity that came my way to try on girls' clothes and experiment with their make-up.

[Xandra]

Reading some of the posts, I often wonder how my mum might have reacted has she ever caught me wearing her clothes!

[heatherdress]

My wife made me buy a pair of high heels for myself to experiment - 4 years ago - very exciting again

About 3 years ago - discovered Heather in Las Vegas

[sarahgrant]

Aged 4 or 5. Wore my sisters underwear and dresses. Knew it was wrong as I locked myself in the bathroom to do so. Now I do it almost 24 /7 and it feels right. The confused little boy is growing up into a confident woman.

[dreamer_2.0]

Hmmmm I have vague memories from when I was quite young, perhaps 4 or 5, of playing with my moms nice church heels and her purse collection. The first time I vividly recall dressing up was in either grade 7 or 8 when I was looking through some old clothes and such to put together a Hercules costume for school. I came across two gymnastics leotards from my sisters and curiosity got the best of me. I loved how they stretched and hugged my body, can't forget the colours too! It was so different from what I was used to wearing and yet felt good, it felt right. I had always been intrigued by girl clothes and girls in general but never had the chance to experiment till then.

So I confirmed my feminine side while looking for a Hercules costume. Ironic?

[Lacey New]

Oh my! I guess I started in my early teen years. School was a great place to see the occasional up skirt live and seeing a pair of panties live was such a thrill. Then when I got home, sometimes Mom or Sis would leave a pair in the bathroom. Well, one thing led to another and as soon as I put a pair of nylon briefs it was wonderful. Then I started seeing ads in the back of Playboy or Penthouse for a place called Michael Salem's and I knew I was hooked. It took a long time to come to the realization that I am a cross dresser and even now, it is limited pretty much to underdressing but I have enjoyed it for many hidden years

[lingerieluva]

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?

Hard to remember the exact time but I'm guessing around 13-14yrs old slipping into some kind of lingerie that mum owned. What sparked that off is the real question! That feeling was so intense it never really went away through all these years. Oh and I was caught by her a few years later as well. I thought I would have a heart attack at the time but got through it ok. Said I was just experimenting at the time and genuinely believed it for a little while. 20yrs later or so here I am.

[Norah_joy]

I was twelve, or so. No sisters in the family, so it was Mom's slips and petticoats; the feeling was magical. At the time, I thought: how can this feel so good and yet feel wrong. Looking back on it, I wish I had told my mother.

Norah

[ArleneRaquel]

At about age eight though it may have been as early as age six. THAT was long time ago.

[Sissy_Michelle]

The first thing I wore... I always helped my mom wash and fold clothes. Some of her clothes were really soft and smooth. I like the way they felt in my hands when I folded them. So I sneaked a pair of panties and bra to try on. She caught me trying to figure out how to clasp the bra behind my back. We had a long talk about what clothes boys wear and what clothes girls wear. Unless I had wanted to wear girl clothes all the time I had better leave her clothes alone. I don't remember how old I was, pre teen perhaps?

So I did it in private for a few years till my girl friend caught me. She thought it was cute and helped me dress up more often but we never left the house except to go to a Holloween Party a couple of times.

[MssHyde]

as a young boy about 5 people would think I was a twin girl to my sister, (when I had a hood on over my hair) I think I felt weird at the thought of it, but sorta good about it too. when I was about 8 or 9, staying at my grandmothers over night she made me sleep in a nightie at the request of my aunt.

also made me wear a something over my hair like a girl. (it was very stimulating)

around the same time I would put on my mothers or sisters clothes, when I had the chance.

I used to put my hair in curlers every chance I got, I like the feel of it. and looking at a full head of curlers in the mirror.

my mother used to make my sister clothes, she would have me put them on, to check her work etc. if my sister was at cheer leading practice or as a surprise for her.

from there the pulling that way only got worse.

[Ina Girdle]

My earliest recollection is trying on one of my mom's girdles, it was a white panty girdle with a satin tummy panel. I was probably 6 years old. I had to hold it up, because it was too big to fit. I grew into them! Could not wait for the Sears and Eatons catalogs to arrive in the spring and the fall. I would go leaf through them and pick out my favorite girdle, bra or corselette on every page. That thrill & excitement has stayed with me all my life. Just now able to CD with my wife's knowledge and approval nearly 50 years later. Ina

[GothicEmily]

I was really really little and tried on some of my mom's clothes. My mom freaked out because she didn't want my dad to see me like that. He was really homophobic and gender-normative, also prone to fits of rage and verbally, emotionally, and sometimes physically abusive. Actually dressing like a girl had to wait for college when some female friends made me up for Hallowe'en a few years running.

[LoriAnn_CD]

I have replied to threads like this in the past but always enjoying reliving the memories. Started pretty early not sure of age. It was out of curiosity with my older sister's bathing suit in the bathroom. Loved the feel and soon tried her pantyhose, then her ballet outfit. Soon I was trying her panties, bras, dresses, skirts and tops. She had one pair of kitten heel that fit perfect and felt so right! I snuck some of her nighties and would sleep in those. I liked that I could wear my sisters stuff. That way I was wearing what the girls in school were wearing. She had several outfits that were my favorite. Makeup came from my aunt. She sold avon and there was always a box of samples in the linen closet. No one ever missed what I took. Wish I had the forum back then!
Love to all,
LoriAnn

[Xandra]

I'm so enjoying reading all these memories...

[heatherdress]

Alexandra - that you for posting a question that each one of us can respond to. We can identify with and enjoy each other's responses.

[BLUE ORCHID]

Hi Alexandra, It was some where around age 4 or 5 .

[Joy3]

When i was 5 or 6 a neighbor girl liked to dress me as her "girlfriend" at her aunts house and we would play with her dolls, etc. I absolutely loved being her girlfriend. Loved the clothes the feel the look!

[cdgirl007]

Under my aunts bed when I was a kid looking for toys, found her box of underwear and hide under the bed all day trying them on

[AnnabelleBethanie]

In reality mine was probably longer ago than I can remember since my memory is pretty awful... But the first time I was remember was about 4 years ago when I was 15... I saw my sisters bra is the washing hamper and it caught my eye and I wondered what it was like to wear it... This is exactly what I tried to do, it unfortunately didn't fit and that was actually quite upsetting... So I carried on with my evening as normal, and then suddenly remember my mum is a bigger bra size than my sister so I went and tried that on - as much as it didn't feel right (due to the thoughts in my head that bras are for girls), I was in heaven while wearing it!

This progressed further into wearing panties, tights and dresses as well... But now I happily have my own bras and underwear.

Annabelle-Bethanie

[bruce]

I was dressed in little girl clothes by my sister as a todler( or so i was told),she continued til i started school.i never questioned my gender i always just became me.she moved out and i had nothing that fit, as i got older i got caught wearing my friends moms terrycloth sundress. my parent sent me to military school.for 2years there was nothing i could do about it. i started surfing at 12 and the bikini was replaceing the one piece and my oldest niece (3 months younger than me )had a talk and sne stared helping me. we were about the same size cause i really a skinny kid and she gave me her undies and bras and other girlie stuff.parents caught me again and sent me to a shrink.didn't matter the shrink heard what he needed to here and see,and it was just a phase.then came viet nam, well not much going on there but blood,guts,bullets,getting hurt and dope.for the next three years(23yrs old)it was all dope.too doped up to even relate to reality.i had an epiphany and fiured out that if i didn't change my lifestyle i was either going to wind up dead or in prison.no help,just dissapeared and cold turkeyed myself straight,not fun but it worked and has for40 years.at that time i started with just panties(i was a commecial fisherman,5-10 days at sea with 5 other guys)got married had three boys and continued to hide.14 yrs later i caugh ther with a friend of mine. she couldn't give it up so i had to walk away from my kids.i started going more femm and enjoyed it alot. found a girl i new in highschool and wound up getting married again,seven years later i told her that i liked to wear womens clothes,she said;what you like to play dressup?; iwas hurt,scared and for the first time in my life confused! we never spoke of it again.15 years later i drive a tractor trailer for an over the road company and am only home for 34hrs and go rignt back on the road. i now have my own panties,bras,cammis,tops,skirts,shorts etc:. would dearly love to have breast forms but have settled for water balloons. i have to pack up all my girl every weekend and hide it under a bunch of stuff in the bottom of the closet in the truck and hope no one looks too closely while i'm off( sometimes someone will drive my truck while i'm off). i'm happiest while i'm at work but will always come home to my wife .i love her and she loves me but don't ask don't tell.i'm 63 now and have had a pretty good and interesting life and it's getting to the point that i just don't give a shit anymore.
life's up,life's down life goes on
metaphisically,we are who we are because we are.

[Meg East]

I was probably about six when I started dressing up in mom's dresses. I had the whole basement to myself and more than enough time to experiment. I remember putting on the bra, girdle and lacy half slip and then the dress and heels. Back then both women and men wore hats so once I was dressed up I would put out her hat boxes and work my way through her collection.

[lucidique]

i started when i was 8 years old my best friends sister was a full
time catholic student all the way from elementary school to high school
and she was the same size as me all the way hehe so i lucked out
when she found out that i was ((borrowing)) her uniforms and
to my surprise she was ok with it and we had a blast playing dress up!!!!!

[Olive_CD]

Around 13, I had half a day alone at home every week. I started looking around the house, found wool tights I used to wear for skiing as a kid, found they were very arousing when put with nothing else. Next, I found a stash of my mom's old pantyhose, and I started discovering the wonderful world of tights.

Once I wanted to try one of my mom's bras, but I was nearly caught that night. I stopped for a while but eventually wearing tights got the better of me and I started buying my own tights. Wearing anything else than tights is a really recent discovery.

[Xandra]

Working your way through the hat boxes sounds delightful.


I was probably about six when I started dressing up in mom's dresses. I had the whole basement to myself and more than enough time to experiment. I remember putting on the bra, girdle and lacy half slip and then the dress and heels. Back then both women and men wore hats so once I was dressed up I would put out her hat boxes and work my way through her collection.

[marlenesexton]

I used to live a block from my school. Back when things like this were still acceptable, I would walk home from kindergarten and I'd have maybe 20 minutes before my mom would come home for lunch from work. I remember stripping nude and slipping into her pantyhose, even encasing myself in them. I still love pantyhose to this day but I couldn't tell you if that experience drives my love of hosiery or I did because I loved nylons from the get go.

[dawnmarrie1961]

Memories can be a very difficult thing to track. Believe me.I've been working on them for years. I can remember my mother painting the nursery walls blue as I laid in the crib looking up at her. Every time I smell fresh paint it brings up that image.So clearly. Like it was yesterday. I remember a lot of bits and pieces of my early childhood. Some memories are good. Others are bad. Uncertain times of difficulty for my parents. My first recollection of wearing girls cloths was at the age of 6 or 7. I was in the first grade. It was a night gown that I would wear when I slept at night. I kept it hidden inside an old wooden radio box beneath a layer of comic books. I'd wait until my three brothers that shared a room with me were fast asleep and then I would slowly lower myself to the floor behind my bed and put the nightgown on. Wearing it helped me to sleep in the dark. I was always deathly afraid of being in the dark. I had sometimes decided to put the nightgown on when I first went to bed and then keep myself tightly covered with a blanket to conceal it. But sometimes my oldest brothers hippie friends would stop in and I'd have to carefully slip the top of the gown off my shoulders. They always came and wanted to read my comics and call me "Faggot." I didn't know what that word meant so it didn't hurt much hearing it until my big brother used it. That hurt. A lot. Especially coming from him. He always apologized for it later when his friends weren't around. The sixties made for some strange times.

[Andromeda]

I starter crossdressing when I was about 11 or 12. The first thing I tried was a leotard. Not too long after that I started to wonder what it would feel like to be a woman and I tried first swimsuits and lingerie. While I failed to avevie my goal the experence was interesting enough that I have keeped on dressing.

[tammie]

HI Luvs: My first real experience was when I was 14yo , and very embarrassed by the fact that I had tits . An older woman (very sexy 35yo) told me by whispering in my ear that I should wear a

brassiere , she said "your tits are bigger than mine honey" and she touched my arma nd rubbedit softly right next to my tit . About a week later I saw my older sisters black lacecup underwire

bra on the floor in her bedroom , it was a 36B and it fit me like I was measured for it and Lo I had tits when I got it on , I have been erect every day since then when I get on a brassiere .

Two weeks later my mom caught me in her bra girdle stockings and slip . She asked and was told I would not stop so she bought me my first bra pantie girdle and slip a week later.

[ErinP]

Easy enough for me to remember. We lived in a few different houses when I was growing up. They got bigger as my parents had more success. So, when I was eight I had a walk-in closet. The former house all the neighbors were girls. And I envied them in their dresses and tights. Loved playing with the toys they had. Barbie and the old tea set thing. But, I wanted to be just like them. So, of course, if you are in the closet no one will know your hiding inside, right? Well I could not believe how beautiful those pantyhose felt! By the time I was twelve I had panties, bras, night gowns and even shoes collected. I remember because that is when the next house came along. That would be the first time I purged!

[Susan Thomas]

I was about twelve and we were on vacation in Canada. For some reason, my aunt thought it would be a good idea to make me wear a bra. (I still remember it was a padded bra) I was held down and my cousins put the bra on me. Years later my late aunt actually sent me a picture of me wearing the bra. I was crying and look quite upset. Shortly after we returned home, I found myself drawn to my sister's clothing. I started with my sister's one-piece swim suit. Of course, my mom caught me and started yelling at me and asking me if I wanted to be a girl. Surprisingly, I didn't crossdress for another ten years. I still remember getting out of the shower (ten years later) and my mother-in-law's pantyhose were hanging on a towel rack. I couldn't believe the feeling of well-being as I slipped on the pantyhose. I sometimes wonder if they hadn't forced me to wear the bra, I wouldn't be wearing a bra, panties and slip as I write this?

[Nicola2876]

I was 5 or 6 when I gave into curiosity. I found some stuffed toys my auntie had made whilst at her house. They were stuffed with old underwear and tights. I had to wear them so I put on some cotton panties and tights. My heart was pumping so hard and the feeling was better than any drug. Years later when I was about 10 I started to wear mum's tights regularly and a pair of stockings became my daily treat that I used to wear.

[Dianne S]

I used to fantasize about wearing a girl's bathing suit when I was about 6 years old. Tried on some of my cousin's panties and dresses when I was about 9. Seriously got into cross-dressing as a teenager, first with my mom's stuff and then eventually I bought my own female clothes.

[Sephina]

I started as early as i can remember was 5 years old i used to wear my moms pantyhose (she thought it was cute at the time)* i believe i may have started out younger but any yonger then 5 doesnt really count as CD more just being a child to me lol

[Sephina]

i agree with you Nicola when i would get dressed up every time i just felt great i couldnt explain it was like a drug i continued to explore myself and what it meant for me growing up at 1st i though it was a fetish cause i couldnt explain it now as im older its not a fetish i feel good and dressing as a woman just makes me happy i love the way i feel and look, and i actually feel attractive for even just a brief moment i LOVE pantyhose and heels always have now i know why hehe

[dashing]

It happened just fter 7 days of my marriage at around 22 years ago. My wife made me crossdressed. But now ssshe don't like that I. Wear her outfits and it makes me uncomfortble.

[Anneliese]

I've always been fascinated with bras and panties. That's why I like the whole "feeling out" process when in a relationship. It is more interesting to me to unclip a bra than to have a girlfriend strip down and get into bed. I liked high heels as a kid also. I still have a good soprano singing voice, and have done female impersonations as long as I can remember (not dressed). I've always thought women's clothes were more interesting and exciting than men's boring stuff. Never actually wore anything from about seven or eight until after my divorce, and then only a couple of times, until about eleven years ago when the pink fog first hit. It only lasted a few months, and then I stashed what I bought until about four years ago. Have spent thousands, all on thrift store clothes, so needless to say, I'm completely addicted.

[Connie D50]

It started when I was in a play for the boy scouts (2nd gread) and dressed at a screaming girl fan for the beatles. I had one older sister and of course my mom both had a ton of great cloths. I would stay home sick in th great and spend the day dressing. the only bad thing was my 2 little sisters would get yelled at for being in my older sisters stuff.

[girlfan]

I started at about 5 years trying on my aunts girdle a stockings, I progressed to wearing my mothers girdle stockings and nylon knickers with a full slip over the top by the time I was 8.
It was the 60's and I was a latchkey child ,my sister left home at the age of 16 , so from the age of 8 I had access to the clothes that were left behind by her ,I was able to spend most of my school holidays dressed in my mum's or sisters clothes , doing housework for extra pocket money in a dress pantyhose and my mums pink fluffy slippers.

[Xandra]

I couldn't agree more about male clothes being boring in comparison to women's clothes. No comparison.
I've always been fascinated with bras and panties. That's why I like the whole "feeling out" process when in a relationship. It is more interesting to me to unclip a bra than to have a girlfriend strip down and get into bed. I liked high heels as a kid also. I still have a good soprano singing voice, and have done female impersonations as long as I can remember (not dressed). I've always thought women's clothes were more interesting and exciting than men's boring stuff. Never actually wore anything from about seven or eight until after my divorce, and then only a couple of times, until about eleven years ago when the pink fog first hit. It only lasted a few months, and then I stashed what I bought until about four years ago. Have spent thousands, all on thrift store clothes, so needless to say, I'm completely addicted.

[LoriFlores]

I've answered so many of these threads I'm starting to confuse myself on dates. Somewhere around age 9, and it was my sister's pink satin tutu. Awesome experience (we've all been there) and I've never looked back!!

[Sindy Lovelace]

Ina, I too started young with my Mom's pantie girdle. Strangly a neighbour saw me looking at a lingerie ad in a ladies magazine and brought around a trainer bra which her daughter no longer needed. Mom said I could wear it under my skool uniform it is was not sports day. I grew from there
luv Sindy X X X