At what age...

[Courtney_Glenn]

Did you start dressing?

Here is my tid-bit:

The earliest memory of my whole life that I can recall was my 4th birthday (1995), and I received a slew of Power Ranger toys. Love me some Rangers!

anyways, my second earliest memory was later that year, prior to my mom's wedding, I snuck around in my sister's room and tried on her flower-girl dress. It is quite possible that I could have been doing some "sneaking around" before this, but this is when my long term memory was barely developed.

So, I've literally been dressing for as long as I can remember

okay Your turn!!!

[sissystephanie]

I tried on my older sister's panties when I was 6 years old. That was 73 years ago, and other then my time in the military and another brief spell, I have been dressing ever since. I have no desire to be a woman, I just like to wear their pretty clothes!

[Regan]

I can remember being home sick from school in 1 or 2nd grade and trying on my moms girdle, bra, and panty hose and realizing I loved it. Haven't stopped since and I am 52.

[Courtney_Glenn]

I have no desire to be a woman, I just like to wear their pretty clothes!

Pretty much the same here

[Nicola2876]

I dressed in a kids wedding dress outfit when I was about four years old. I remember running and laughing with a friend.

At about five or six years old I stayed with an auntie and found some panties and tights. I didnt know why but I just HAD to wear them.

[moondog]

Shortly after my 6th birthday, I got caught wearing my sister's panties by my mother. I know this because I was home with the mumps. Last week I asked my mother when I had the mumps and she told me it was right after we moved to Maine when I was 5. So I was either 5 or had just turned 6 when I started wearing panties, at least.

[BLUE ORCHID]

Hi Courtney, It was about 64years ago when I was about 5years old.

[Aloha Jayne]

At my high school reunion, one of my classmates reminded me that in first grade, I told her I loved her dress and wished I had one like it. I had forgotten that, but I would have been 6. And I know I got caught trying on my sisters underwear at age 4 or 5. Then again in first grade, me and my best friend Leslie played roman soldiers in an Easter play. Our moms made the costumes which were basically a tin foil vest and a royal blue pleated skirt. Google a picture of a roman soldier to see what I mean. So I beggggged my mom into letting me wear the "soldier uniform." She finally gave in when we were at my grandparents house, where nobody an our small town would see, and I went outside and climbed trees and played football wearing a pleated skirt. It felt soooooo wonderful! The mail man even called me girlie and I still loved to be called girlie.

Aloha Jayne

[eluuzion]

First time was at age 28 while back to college to earn more useless degrees.

Part-time entertainment with no depth until I divorced (17 years ago). That was the point when I jumped in on a daily basis.

I have no experience juggling CD with an SO in a relationship to date. Yes, I have been single for 17 years now. No, I'm not avoiding relationships, I have just never "searched" for them.

[shawnsheila]

I have been dressing up since the age of 14. It started out with me wearing my moms pantyhose that she would leave in the bathroom cloths hamper then, as it progressed,I'd sneak into my moms closet and try on her clothes (full outfits) while my parents were out. I looooooved the feeling but then I felt extremely conflicted and scared about being caught (being raised catholic in a semi conservative family). Later I figured out that I was not gay and that I just feel good when dressed (thats the only way I can explain it... feeling good or right while being dressed) Now because I work from home, part of my morning routine is to dress up after I get the kids and wife off to school/work. My major regret is not dressing more and embracing it when I was younger i.e. in college. I had an excellent body for it (I was 130lbs) and many of my friends would not care if I did.

[Patty F]

Started at about 8 years old with moms clothing. I had a lot of guys with sisters my age in the nieborhood and was able to get some panties once in a while that way.

[stacycoral]

iWhen i was 12, trying on my sister clothes, never got caught that i know of, Did dress for my sister once back then. dress ever since.

[Jenniferpl]

Tried on my sisters bra way too many years ago, probably 8 or 9 yeaqrs old, and I have hooked ever since.

[vikki2020]

I was probably about 4 when I tried on some nylons, and the light went on!! Maybe 10, when I started to try on more things, bra, panties, and went out in public at about 15! Was there ever any doubt that's where I was headed?

[paulaprimo]

i was probably about 9 when i got into my moms things and tried on her bra and stockings, and how i enjoyed it!!

[kimdl93]

My earliest recollections, as a 3 or 4 year old, involved being interested in my older sister's slips and undies. I first tried them on when I was 4. I also exhibited some feminine behavioral traits as a preschooler and was teased about it by my older siblings. So, I learned to hide and repress.

[sheerpanties]

I must have been around six or seven the first time I tried on my sister's panties. What a rush! From then on, as I got older and my parents felt comfortable leaving me home alone, I would go through my sister's panty drawer and try on numerous pairs. I had to start going to the dirty clothes though, as I was usually really excited and "leaking" a good bit by the time I got the first pair on. I later tried on a dress or two, but never really saw the point since I couldn't fill them out (no boobs). I had longer hair in high school though and very much remember how excited I would get when everyone left home and I'd put on a pair of my sister's panties and then put my hair up in curlers. Wow, that was the most incredible feeling! Great thread Courtney Glenn. Seems like we all started pretty early down this road. By now I have a huge panty and bra collection and am starting to collect more and more dresses, skirts, blouses, lingerie, scarves, belts, etc. I can't wait to get more!

Cheers,
Angie

[meganmartin]

My earliest memory is around 11 or 12.
Did not buy a wig and or makeup till around 2006 where i started working on my full presentation.

[shawnsheila]

Jennifer I love your outfit and you look stunning in it

[Jessica Who]

I started when I was around 7 years old, though I had wanted to try it sooner. I would sneak into my parents' room after school and try on my mother's dresses.

[BillieJoEllen]

Although I had worn girl's things before I was almost 12 when I was 'hooked'.

[BRANDYJ]

Earliest recollection was when I was either 10 or eleven. I think it was the same year my dad died. We had moved soon there after. I recall finding my mother's nylon full white slip hanging on a hook in the bathroom door. I felt it and it felt so smooth. I got excited and ended up with it around my privates. That was the first orgasm I ever experienced. I was so naive that I had no clue as to what happened. I was both scared that I had somehow hurt myself and yet the feeling was so intense and good that I never forgot. The house we rented had a separate garage with a garage apartment above it. it was not occupied and I found a big box of clothes left by the previous tentant...I assume. In it was some skirts and tops. I for some reason had to try them on. I used to return to try them on as often as I could when I knew my mom, brothers or sister were not around. It would end up in an orgasm and I felt compelled to just about rip the clothes off. I remember feeling something was wrong with me to want to do this. But still had to do it for whatever the compulsion was that drove me. Oddly enough, i never tried on any of my mom or sisters clothes. Including that white slip. I am guessing that somehow, even at that age, I felt wearing their clothes would be just so wrong. Wearing girl things was rare beyond that early first year. Maybe for lack of clothes or because I started noticing girls and had several girlfriends even at age 11 or twelve. Whenever I had a girlfriend, or was trying to gain the attention of a girl I wanted as my own, I clearly remember feeling that dressing in woman's or girls clothes was something i did not want them to know about me and I'd not try anything on even if it was available. As best as I can remember I did not try on any female clothes from age 13 till 16. My mom died when I was 16 and I remember trying on a skirt that I think I got at one of those charity drop boxes where people could donate clothes. I felt any bags or boxes of clothes left along side those over filled boxes was fair game. I'd grab one or two, run home and find any female clothes that fit and return the rest. That continued even through my first marriage at age 17. (yes, way to young). My first wife never knew in the 5 years it lasted.
At age 26-27. I met and fell in love with my second wife. She was the first person I ever told. In time she became more then accepting and was playful and helpful in my dressing. In fact, that is when it became more often and less sexual. She died after 10 years together and since then my third wife of about 17 years and my present SO both knew and were/is very accepting too. My life as a crossdresser has been good once I accepted and knew what I was soon after telling my second wife.
Forgive me for rambling, but this thread made me think of the chronology of me as a crossdresser. But that's another thread.

[KarenCDFL]

I remember trying on my mom's tights, stockings and shoes at about 3 or 4 and then playing with her makeup.

This stopped till I was about 11 or 12 when I jumped it with both hi-heeled feet!. This went on at home till she caught me at 16. (a whole different story related in other posts here).

I had to stop till I got my own place in my early 20's and I have dressed ever since.

[Miss_Roslyn]

One of my first memories is of me sneaking into my younger sisters make up and trying on lipstick, eye shadow, and blush. It was quite the expierinece that i will be forget.

On a related note, its comforting hearing these stories and being able to relate to people, after feeling so weird for so long

[Katie83]

I think i was probably about 9 (20yearsago) when i first tried dressing up. The first clothes i remember trying on were my sisters polka dot swimsuit, and bright pink layered skirt. I have stopped dressing for short times, but i've always come back to it. I don't want to stop dressing again as it makes happy doing so.
Katie