When did you first crossdress?

[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.