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.

:love:

[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?:battingeyelashes::battingeyelashes:

[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

[Megan72]

I really cant remember an age but I lived in North Carolina which would have been around 1st or 2nd grade. I tried on my moms clothes and was hooked. My sister was quite a bit younger than I so I never got the chance to try her pretty dresses, but oh how I wanted to. Kelli

[Brown Eyed Girl]

Like many homes, we had a clothes washer, but not a dryer. My mom would wash the clothes and hang them outside…except for her delicates which always hung in the bathroom. While I cannot recall exactly when, I do recall seeing her white slip hanging in the bathroom and having the urge to try it on one day when everyone was out the house. It was so different….just a piece of clothing. But putting it on made me feel like someone else. I could envision myself being a beautiful lady on TV, singing to audiences, or just being at home doing chores.

While there was certain a level of arousal, it was more of an excitement of transforming myself into someone else that got me hooked. And everything seemed to fit me back then. I was young and in great shape from playing sports. It made finding things to fit easy when you were a young teen.

[Melissa.Lynn88]

I started around the age of 12 with my mom's stuff. But the desire to do so was there from a much earlier age, probably like 5. I just tried to suppress and ignore it up to that point.

[donnatracey]

Early teens when I started trying on my mom's dresses and red lipstick.............:heehee: Remember the time I almost got caught with the lipstick - played it off as chapped lips, which I had as a child. Nothing else was ever said.....

[karenlong]

i was 8, put on my sisters clothes, it all felt so right, been a cd since, im now 51

[JessicaM1985]

The very first time I ever did anything related to crossdressing was when I was 12. My family and I went to see one of those fake hypnotists and I got selected to be part of the act. The hypnotist had this guy and myself put on makeup and act as a couple for cheap laughs. I found that wearing it made me feel good. But I didn't start personally crossdressing with clothes and whatnot until I was 14. I had this dream, and in it I was loved and accepted by people more because I was a girl. I had more friends and was just a happier person. I even had *gasp* a boyfriend.

A few days after this dream, I went and found so of my dad's (now)ex-wife's stockings, bras and panties along with her makeup kit. I tried my best to look the way I did in the dream, but without much success. I did discover that I enjoyed it and did it semi-regularly for about another year before I was caught. I made the mistake of wearing stay on mascara, and it wouldnt wash out. I foolishly tried to walk around and pretend it wasn't on, and my dad's ex wife clocked me. Literally. I had a nasty lump on the head and endured about 20 minutes of being called a faggot and god knows what else.

Only recently have I started dressing to the point that I was back then...

[taís]

I think I had 10 or 11. mom's bra in the bathroom. I remember I locked the door real quietly so anyone wouldn't listen and wonder what the hell was I doing.
but I don't remember thinking about it again until 22 when... a girlfriend asked me to wear a piece of lingerie in bed. we broke up later that year (that's 10 years ago), I got my own place, started to dress and never stopped (okay one... two purges?) ever since. <3

[Diane Smith]

I definitely had the urge to get into my mom's things when I was two or three years old. But at that age, I was under constant supervision and actually formulating and carrying out complex and stealthy plans to raid her closet was beyond my ability. By age five I was definitely obsessed with women's clothes and especially high heels, and loved to play with my mom's but didn't wear them because they didn't fit. By age nine I had my ears pierced and was wearing nail polish and lipstick most of the time, courtesy of mom, who understood there was something "special" about me. She also bought me my first pair of "grownup" heels when I was 12.

- Diane

[daine]

at age 8 tried on a brown unform on and liked it.

[janet p]

I started at about 7 or 8 with slips and panties from the hamper and then to my sisters (she's 6yrs older than me) nightgowns loved the silky feeling on my body. Then at about 11 or 12 I started trying on mom's nylons and dresses and being of catholic up bringing in NW Chicago there was always the fear of being caught (which did happen a couple of times) added to the thrill of it. Still dress now off and on wear panties 24/7.

[DAWNB]

Well the best recollection I have is when I tried on my mothers slip at age 13. Felt good so I managed to hide it (was old one heading for trash) in our attic where I played alot. Wore it when I could and one day mom came up and I didn't hear her. She didn't get mad as I think she just felt it was of those things that enquiring minds want to know. Kind of got hooked so I played it casual and wore when I could. Got married and of course didn't tell wife and then I went into service so I was off dressing for awhile. I did on occasion get some time as we lived off base and when wife went to visit back home I had chance. Used her items as I didn't own any of my own. Fast forward to getting out of service and now have been in Calif since late 60's. Was dressing off and on without wife knowing. Then came the fateful day when we were vacationing and she told me she knew I was wearing. Thought I was a goner. Well that was early 90's and she is still with me. She only tolerates my dressing so I am careful not to offend her. Have my own apparel so I don't touch hers. Just so you know I am 74 and wife and I will be married 56 years in February 2012.

[STACY B]

I got to be the one to say it ?????? Everybody that responded well almost everybody said ,,, The hamper YE OL DIRTY CLOTHES HAMPER !!! It sure dont take long rto figure out if you realy dont want to get caught you better not get any clean underwear or ELSE ,, There aint no hidding that sissta ,, Stretched out pantyhose ,, NO way can you make them look like they were not worn !!!!! But for some reason Im just like the rest about 4 or 5 maybe dont know exactly sister comes busten in the bathroom ,,,,, BAM ,,,,, There I was just fixxen to get my second leg in those sweet coffie colored pantyhose ,,,, WOO ,,, WEE ,,, She just could not wait to tell ,,, But I got the last laugh ,, Cuz she was 10 years older than me an her shoes fit me perfect for a many a year sissta,,,, Thanx ,,, Right smack dab in the middle of 70s platform craze ..... LOL... An did I take full advantage ohhhhhhhhh yea,,, Just noooooo end to the storys this ol gal could tell ....

[Meg East]

Maybe nine or ten, there was a bunch of clothing under the stairs, bras, panties, girdles and dresses. Keep me happy for a year or two until mom cleaned up the basement. I had saved the best so not much was lost.