How did you start down this road?

[RichardTO]

I started just before my teenage years. Had a sister and two stepsisters who always seemed to get away with everything while I always seemed to get the short end of the stick. Complaining to them about it got nowhere, they always said "You don't know what it's like to be a girl!" and never argued anything further.

One night, I went to my mom and asked what it was like to be a girl. Her response was that it was just something you do. After a bit, she suggested for me to dress up to get an idea of what it was like and she put me in one of her dresses. I was told that with a little makeup and my hair done, I'd be a very pretty girl. I wanted to see, so next day we did that. That was the point mom said that I looked good enough dressed that maybe she should start getting me dresses and skirts. Was a bit taken aback, but she offered to buy me things if I would wear them. I kind of liked it, so I agreed to it.

That started several years of very regular dressing, both at home and outside. I left it behind when I went to college, but the memories are always there.

[bridget thronton]

My dressing was hidden from my mom while growing up and wearing her clothes.

[docrobbysherry]

I started in my 50's. Dad had passed and my mom had Alzheimers. My daughters disagree about Sherry, but my sister thot it was cool!

[Cheryl T]

I was 5 or 6 when curiosity got me and I tried mom's panties. They felt so different and actually so right, I loved them.
Sometime later I tried her bra too and as time passed a slip, then a dress, an OBG and stockings, then her heels. When I dressed completely the first time it just felt natural.

[RichardTO]

Yeah, I wound up with panties, bras, nightgowns, swimsuit, a sundress, skirt and blouse almost right away (not to mention a couple pairs of shoes).

I don't know if I would have started without the help and encouragement of my mother. Being a kid it was hard to understand what her motivations might have been. Wasn't until I was talking to a therapist about it in my 30's that they pointed out that my mother hated my father after their divorce and I was a small version of him. Add to that mom was a raging narcissist, and it gets easier to see.

Not to say I didn't enjoy a lot of it, or that it didn't help me grow as a person.

[April Rose]

I remember having an interest as young as 4 or 5. I got caught a few times around age 7. It could have gone worse, but that doesn't mean it went well. The first time learned the word "transvestite" I knew that was who I was.

[Bluesman]

I was 15, playing one of the kid roles in a professional production of Macbeth. Dressing room space was limited, so couple of the gay men and me (go figure!) shared space with the female cast with just a clothes rack separating us. One night when I was alone in the dressing area, I noticed a pair of panties on a chair. I pocketed them, took them home, put them on and masturbated. Around that same time I discovered a trunk in the attic with a couple of nightgowns in it and started wearing one to bed. Over the next years I found or purloined panties until I got up the nerve to buy my own along with a matching bra in my early twenties. Dressing was limited to those kind of lingerie items, off and on, periodic purges, reading cross-dressing letters and stories in Penthouse Variations (how many remember that publication?) til my mid-30's when I bought my first dress, which was later purged. Things continued that way more or less for the next 20 or so years, hiding it for the most part from my wife. In my late fifties decided the only thing "wrong" with CDing was hiding it from her, so put it more out in the open. Didn't go well initially, went back into hiding although the secret was out of course. Eventually started purchasing dresses, skirts, blouses, shoes, etc. wearing them in private, and occasionally being caught if my wife came home unexpectedly. It's all out in the open now, and I dress more or less as I want to.

[LizMichelle]

Age 8, discovered a dress I liked at a second hand store. Mom noticed I liked it, with me having Asperger's Syndrome and let me try it on. Went into the dressing room and put it on and loved it on the spot. Came home with it, mom did buy it for me.

[oh to be rachel]

There was always a tickle of an interest.
It was a neighborhood costume party where the wife and I wore wedding dresses that set it on fire in my head.
Years of pink fog followed.

[NancySue]

At 5 or 6, got invited to play games by next door sisters. After a couple games, they decided to play dress up and invited me to join them. Initially, no interest, until I tried on some thigh highs even though they had runs. Wham, bam. ⚡️ They felt so good. Still do. The sojourn began.

[BLUE ORCHID]

It was 78 tyears ago @ age 4 Playing with Mom's Hose & Heels, And the Rest is History,

[sara66]

Around 4 or 5 put on one of mom's bras and progressed from there,
Sara

[Georgina]

It started with me in the late fifties (1950s) when I saw my first petticoats and stockings and suspenders at school. I began by wearing my mother's and much later when I got my own clothes it felt wonderful and right. I have continued dressing ever since.

[CarlaWestin]

Mom's bras.

[Erin77]

Around age 5. Moms panties. Don't know why but the material and feel of it just kept me going. Then bras, lingerie, pantyhose and finally just dressing all up as I got older.

[countrygirl]

Started at age 11 with moms bra and panties and then quickly added moms skirts and blouses and into dresses. At grandma's house wore some old wigs she had in a trunk and one of her dresses in the bedroom that I stayed in and next thing you know it took off from there. Now 44 and living on my own and have more female clothes than male and looking at microdosing HRT and loving every minute of being able to express this side of me. Who knows what is next maybe it is transitioning to female. Don't know and frankly don't care to know. I know that I can express this side of me and love every minute of it. To be able to express this side I that was not allowed to flourish and enjoy and now I have the freedom to do so. I love it.

[Sabine Janus]

Sister dressed me as her doll.

It took.

[Monique65]

I found my mother’s OBG and stockings, slipped them on, and my world changed.

[Jillcder]

When I was in grade school I dressed as a girl for the school Halloween party obviously I did not resist and I can still remember my teacher telling me my makeup looked good. Not sure if that seal the deal on my Crossdressing journey but it is my earliest memory.

[JesseVF]

Very young but I think it was actually open bottom girdles I found in the laundry. Soon after that Moms bras stuffed with whatever I could find.
I?m jealous of those who were assisted in this pursuit. I remember putting on a dress over my clothes once when hanging out with my older sister trying to get her to take the hint but she pretty much ignored me.
And yes Bluesman I remember reading the Penthouse letters and always hoping there were more of the cd examples. Newspaper advice columns also once in a while included a cd example which of course I found fascinating.

[Stephj]

When I was young about 4 or 5 when I would go to the store with my mom and sister she is three years older than me they would find me in the lingerie section of the store looking at and feeling the panties and bras. Then one day i was at home I walked by sister?s room and on her bed was a folded bras and panties she had just laundered. I went in to feel and look at them time got away from me. Next thing I new my sister was in the doorway she said would you like to try them on I said yes she have a pair of panties and go try them on them she help me with the bra I was hooked. I wore them every day. Then about a month later mom have me a hug and realized I was wearing a bra she said boys don?t wear bras for sister said he is also wearing panties had to take them off. A week later I asked my sister for them she handed them to me i started wearing them again about a week later mom found out she finally said I figured s you like them from all the times i found you in the store looking at and feeling them. She asked if I wanted my own I said yes. She said I would have to buy my own. I had allowance money I had saved so we went to the store I bought two pairs of panties black and blue along with two bras. Been wearing them ever since. I will be 61 in a few months

[Stephanie47]

The very first time I ever put a femme garment on was my mother's nylon nightgown. I know I was very very young. My mother constantly was saying I was suppose to be a girl because her first born was a son. He is a year older than I. I guess her idea of the perfect family was husband, wife, older son and younger daughter. I put the nightgown on and cried that she did not love me because I wasn't a girl. She hugged me a told me she loved me and never said anything about me not being a daughter. I often wonder if that set my mind on the direction of wanting to wear femme garments. I always believed that my mother doled out more physical discipline for me because I was not a girl. My older brother walked on water and got all the new toys/bikes while I got my ass whipped. A couple of years later I discovered her full slips that she hanged to dry in the hallway leading to the bedrooms and a drying rack over the bathroom tub. I loved the feel of the nylon. At first I just fondled the slips but ultimately I had to slip into them when I had the chance. I had an experience as a really younger kid, maybe four years old.

When I was about four years old I started having visions that I was a young woman who had been murdered and left in a muddy dirt parking lot and I was dressed only in a white full slip. I have no idea why this vision arose because we did not have a television set and I know nobody would have been talking about something like a murder with that much visual detail. It wasn't until decades later than my wife started watching a program concerning "past lives" that children remember that, just maybe that was such an experience.

[Katherine L.]

I first started at 11 or 12 by wearing my mom’s bra I found in the clothes hamper. Now almost 67 and I still love wearing bras.

[Kelli_cd]

I used to spend summers living with my grandparents. When I was 4, I discovered my grandmother's petticoats. I only ever write them over my clothes, but i liked them.
When I was 7,I tried on my mom's girdle. I didn't care much for that. I remember it feeling very rubbery. (It's odd, now i would love to have a girdle! )
At 11 or 12, my mom and sister both started wearing nylon panties. After wearing their panties, there was no turning back.

[KrissyTN]

I was around 7 when I started to notice my mom's bra's on a stack of towels just above the clothes hamper. Being in the bathroom like that afforded me the opportunity to try it on one day boom, I was hooked! After that, whenever I had the chance I would try on various clothes. It wasn't long before I discovered that my aunt & grandmother wore OBG's with garters and that set me down the path of admiring and loving those, garterbelts and stockings. Heels were much later, but a fun discovery too!