When did you first crossdress?

[Tiki]

I had tried my mom's lingerie when i was something 13 or 14.
Feeling was great. Unfortunately couldn't continue it and regret now.

[Lexi Moralas]

I was 11

[Roli F]

I was 14 house sitting pets for friends his older sisters clothes were left on the maiden, dry I was captivated, crapped myself thinking they would notice the clothes had been worn when they got back, they didn't. hooked ever since never looked back.

[clarisse-tv]

first experience was about 12 with moms pantyhose.
first full dressing was 6 years ago
last full dressing was 4days ago

[Valarie]

I remember (because of my therapist) I had one of my mom's night gowns as a security blanket, I loved the silk feeling. But when I was 4 it was taken away from me. Around 8-9 my harder childhood years I found it so much fun, I would be left alone for hours, and would walk in pantyhose and heels. I loved it. But then I was caught, and had to repress it.

[Sissy_Michelle]

There were some girls down the street when I was like eight or nine. Since they were about my age I was invited over a lot and vice versa. During one of their parties I got wet and was given a change of clothes by their mom, the sisters and their friend made fun of me and said if I didn't put on the clothes that they laid out for me they were going to send me home. I didn't have a lot neighbors or friends for that matter so I was dressed up in dresses and and anything they gave me to wear. After the first time it became a habit to dress up with them, it lasted well into high school.

[Rick5881]

I was probably about twelve years old the first time I remember wearing my mothers panties, bra, girdle and makeup. I remember because my mother came home early and nearly caught me. I ran to the bathroom trying to wipe my face and remove her undies at the same time. If my mother saw me, I'm really not sure, she never said anything. I've been a cd ever since, but always when I'm alone, but now I'm trying to get the courage to be me, when I can.

[Cindia]

I honestly can't remember the very first time. First extended time (more than just put it on , take it off real quick) was in third grade, so I would have been 8, almost 9 Stayed home from school sick for two days, but not too sick to spend most of them wearing my sisters clothes. Wore everything, panties, bra, blouse, skirts dresses, shoes. Got pantyhose from, mom, sisters had a few pair of tights but I liked the pantyhose better. I remember wanting to wear a one piece shorts/jumper type thing that my sister wore when I was 3 or 4. Can't say I ever got to.

[JenniferYager]

In eighth grade I wore some of my mom's clothes. I actually dressed up as a cheerleader for our spirit day in high school as a sophomore, that was my first time out in public. Funny enough, nobody cared except the assistant principal, who said my boobs were too big (I had overstuffed them a bit)!

[DanyGirlie]

I first crossdressed when I basically started walking!!! I can't remember a time when I wasn't a xdresser... that's why I feel like I'm a girl although that doesn't effect my masculinity.

[Martha G]

Basically in my late 50's

I went to a costume party dressed as Charley's Aunt.

I wore a beautiful period dress supported by a 120"lace trimmed hooped petticoat. I had a gray wig with curls, a fancy bonnet, hanging earrings, string purse, a black lace fan and a large bust. I also wore a pair of yellow satin bloomers with a lot of lace. The makeup was basically foundation, lipstick and eyebrow pencil.

Since then I have developed a few more female characters such as a duchess and a Southern belle. Also I dress as Martha Stewart.

Off and on throughout my life I wanted to at one time to dress s a lady but it never was a compulsion.

My avatar and profile photo are me as Martha Stewart.

[Valerie1973]

I remember I was 5 or 6. I liked this rust colored dress my mom had. I liked dresses and skirts there after. By age 10 I started trying on everything I could get my hands on. Mom was very fashion savvy and loved to shop and had a closet full of dresses, skirts, blouses, high heels, drawers full of pantyhose, slips, bras. This was 1983, Boy George and glam rock on MTV had a huge influence on young Valerie. I started experimenting with make up too. This is when I also learned to walk in heels. At age 12-13 mom's clothes were fitting me just perfect but her little size 7 feet and me at a size 9 men's, I no longer could were mom's high heels. . I am an only child, I was left alone a lot. This was my routine during summer vacation. My parents would leave to work around 7:30ish and I'd bounce out of bed and doll up with make-up, do the underwear, pantyhose, slip, bra padded with whatever, then find a dress or skirt and blouse outfit, and then heels. Back then it was OK to leave a kid at home at age 10 or 11. I think that's about when I started staying home alone. I'd spend the entire morning like this, changing out fits, reapplying lipstick, walking back and forth in the house. I was a healthy normal young crossdresser. By 11 11:30 I'd put everything back as perfect as I could and wash up. My mom would come home for lunch. The rest of the day I was a normal boy playing Atari 2600 and hung out in the yard or street with the neighborhood kids. Still dressing up after 35 years.

[mexdresser]

I started at the young age of 6. I used to love watching my mom get all made up and think what what it must feel like to wear makeup. Later in life, I remember how excited I would get when I found out I would have the house to myself, even if only for a few hours. Back then I was able to fit in my mom's clothes, even her shoes. I suspect she had suspicions but never said anything.

[Allison Quinn]

I can't even remember the first time anymore.. it's been a thing in my life ever since I as born. I just genuinely liked the way I looked 100 times more.

[Breanneb]

I think I was 5 when i first put on a pait of moms stockings and fell completely in love with them, boy if she could see me now

[Stacycdinma]

I'm probably like everyone else. Put on mind bra at a very young age and pretended to be a dancer. Later on I tried her panties and couldn't believe how good they felt. Have been wearing lingerie and dressing on and off ever since

[Ceri Anne]

I was just talking about this the other night at the Transgender Institute in Kansas City. My first time was one summer when I was about 10. The girls in the neighborhood, had been putting on nail polish at the picnic table and left it out. I was drawn to try it. Painted my nails a deep cherry red, then realized I didn't have a clue how to take it off.......oh well, it wore of soon enough. My next time I was around 13 and my mom had a stretchy satin body shirt and brown velvet kulaks. I had so much fun, I had to do laundry when finished............ I have always have a strong fem side, but never fully accepted it until recently. I've always gotten along better with girls, and in fact, never had a real close male friend until the last few years.

[Ceri Anne]

There were some girls down the street when I was like eight or nine. Since they were about my age I was invited over a lot and vice versa. During one of their parties I got wet and was given a change of clothes by their mom, the sisters and their friend made fun of me and said if I didn't put on the clothes that they laid out for me they were going to send me home. I didn't have a lot neighbors or friends for that matter so I was dressed up in dresses and and anything they gave me to wear. After the first time it became a habit to dress up with them, it lasted well into high school.

You are such a lucky girl Michelle, that would have been so incredibly fun

[irishsissy]

I was about 10 yrs old.

[Bethany38]

I think I was seven-ish. I tried on some clothes of my cusin.

[sperow2003]

My first real crossdressing came about when my wife to be suggested I try on her panties (way before marriage and children). She must have seen my reaction because it soon escalated to me occasionally wearing a favourite dress of hers which was floral and extremely silky. Over the years this "pastime" has given us both so much pleasure, me especially I must add.

[melissagrrl]

At about 6 years old.

[SamGreen]

I was 6, my aunt had a box of see through baby dolls, or something like that, and I just needed to put them on when no one else was watching. I've been hooked ever since.

[themodsca]

sisters heels,....
started from the feet to the head i spose

[mykell]

same for myself except they were my aunts heels, mom and dad were divorced when i was two, did it whenever i could, would love to sleep in my sisters pantyhose, cant believe all the story's hear, i feel so at home.