At What Age Did You Start To Crossdress? / What age did you start cross dressing? Why

I grew up with an intense nylons, girdle, spiked heel fetish. My main weakness was the nylon stockings for sure. I can remember when I was 10 I would stay after school at a neighbors house until my mother came by after work to pick me up. They had three older girls around 11 thru 14 that loved to dress me up in there school uniform which always included tights. This was in the early 60's and all women still wore garters and stockings. I remember being embarrassed as they made me walk in front of their mother as she also laughed and thought it was cute. Even helping the girls at times put lipstick on me. As I was embarrassed I also loved the attention and loved feeling wearing those nylon tights. One day they thought it would be cute to put me into their mothers ultra sheer RHT shiny brown nylon stockings, girdle and high heels. The sensation of those nylon stockings drove me crazy and my nylon fetish was born. The funny feeling in my stomach turned into a visual sexual reaction that I could not hide. I remember I was in tears as they showed their mother my condition and state I was in. As their mother did laugh the girls got into trouble for exposing my fetish weakness that they had discovered. Their mother winked at me and told me it would be our secret and she and the girls would never tell anyone.....To many other stories about wearing nylons and those young dominatrix girls.

Ok everyone please dont laugh but im 23 now only got into all this when I was 21 as my then girlfreind got me to try a dress on she was making so she could sew the hem on it.

Anyway I enjoyed it alot and a few weeks later she asked me to do it again and I did after that started trying on her stuff when she was not around and would sometimes try on a drees she was making so she could do the hems etc.

Anyway 2 years later shes left me (not due to crosssdressing) and Im still enjoying dresing up have got some things of E-bay skirts mostly and love em, and hopefully can carry on doing so :)

I started around the age of five. In fear and excitement, I would sneak into the bathroom and take from the linen basket a pair of my mother's tights or stockings to try on. They had a wonderful soft and silky feel that filled me with delightful sensations. I often wore them to bed. As a young child I dreamed myself magically transformed into a woman, and would imagine myself with boobs, or being held in the large bosom of an earth mother goddess.

I got my start very early i think it was around 7 or 8 and havnt looked back since there isnt a day i dont dress enfemme i wear my enfemme underwear to work every day as a auto mechanic:love:

Actually started dressing in mid-life, after suppressing for many years.
Even as a child, I can remember wanting to wear that cute party dress, the special Easter dress, my date's prom dress, etc, etc, etc. As to why...well, I just plan to spend the rest of my life exploring the feelings and having fun.
:heehee:

I was about 12 when I snuck into my cousin's room, and tried on a dark blue leotard and tights. Was transformative! I've always loved leotards, tights, nylons, bodystockings. Second skins are magical!

I remember as child of 3 or 4 going around in my mothers shoes when ever I could get them, and I also would spend hours in my mothers underwear drawer touching and feeling her panties and stockings etc right up till I was about 10. After that I went into remission until after I was married in my early 2o's and then the urge to dress start again and is still with me 30 yrs on.

Collette

I started crossdressing at the age of 8 I started wearing my moms panties bras,skirts and blouses than went to my sisters clothing. on time i was in the shower and my mom came in to use the bathroom when i was about 13 and found a pair of her panties rapped up in my clothes.she didnt say much but she kept a very close on her stuff because she would ask me time to time if i had barrowed some of her clothing.

I am a 50 something... I've had my secret (:rolleyes:) since adolescence. For some reason I've always had my head in the clouds and I wasn't fooling anyone. That knowledge was seldom talked about in the house, other than my sister calling me a "Queen" and one brother calling me a "Fag" when they were mad at me. Other siblings never mentioned it and we were always their for each other when needed.

I boxed, played football and baseball. I did well in all sports and despite all my trying to be macho I was voted most likely to sell ladies lingerie while in high school... or maybe wear lingerie.


sugar

How old? I was nine, almost ten, years old.

Why? I could no longer resist. It was something I had always wanted to do.

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Originally Posted by Rachel32533

It was early... I have a twin sister and I remember wearing her cloths very early. Mon would often put me in my sister's cloths if mine were dirty. My first memory is about five went my mother dressed me in one of my sister's dress including panties and shoes. It felt great, and I wondered why she always got the perty cloths? It continued until I was about 12, I even had to wear her panties to school if mine were not clean. One day went I was in the 4th grade I had on my sister's panties at school and I knew something was different! I then started wanting to wear her cloths more and more. I was the same size as my siter and we looked identical. I continued wearing her cloths all the way through high school. When the family was gone I would change into her cloths and put on my mothers wig and cruise around town. Often people would confuse me for my sister. My desire has never gone away. I still dress as often as possible. While my sister knows about my crossdressing I have not brought it up to her in many years and she has not asked. I am certain that the desire starts early, and will never truly go away.

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Racheal this sounds like my life although I had 2 more sisters taht were also twind they were 2 years older than me and my twin and always dressed me in there clothes from the time I can remember, in Junior high school I could dress just like my twin and people couldn't tell us apart either.
Maybe we are destined to be here, in this forum I mean.:love:

I started at 13 or 14 by wearing lipstick whenever i was alone and here i am at 59 and still love dressing up after 46 years!!!!

I started crossdressing after about five years of marriage. We were struggling with two kids, her unemployed and me attending college. To pass the time, we splurged on an Atari 2600 game for our TV. (It was our Christmas present to each other.)

We spent many an evening beating the pants off her (literally) while playing the old ping pong game and then redressing her in one of her mini skirts / dresses before we had a long romantic session. (Enough said?)

Well, she started practicing during the day (unfair) and she turned the tables on me. (I actually started looking forward to loosing because we had some really hot sessions after that.)

What I discovered, as all of you know, is that the clothes are comfortable, sexy, and fun to wear.

As the years went by, she gained weight - third child - and many of the clothes we used for play simply ended up on my side of the closet as did the panties end up in my drawer.

With my face and build, I will never pass as a GG, but we have our fun and there are times when I miss the old days when we were so poor that play time consisted of strip and switch clothing.

Oh well - memories - we cling to our memories.

CE

I must have been 8 or 9 when I first started dressing. I remember my sister getting a ballerina tutu as a gift and as soon as I saw it I had to try it on... I'm not sure why, but I just had to. The thrill was incredible, and before I knew it I was sneaking into her room every chance I could to try on panties, skirts, nighties, etc.

As I got older I enjoyed my little secret every chance I was in the house alone and thought I'd stop any time I wanted to. I got married (for the first time) at age 21 and after a couple of months of "behaving" I was shopping for the first time to buy my own lingerie. (I've always had a thing for babydoll nighties and to this day I have amassed a large collection and I love wearing them every chance I get.) That marriage and a second one didn't last long (for other reasons) but after my second divorce I really enjoyed dressing (always in private). I spent almost every night for a year in babydoll nighties, was able to spend several days in a row fully dressed and was loving every minute of it.

Alas, I had to go and fall in love again though. I am now 47 and very happily married (8 years) to my third wife, although she still doesn't know about my dressing. I just can't bring myself to tell her, I just can't imagine how she'd take the news. She works during the day and I work in the evening so I have plenty of time in the house alone to pursue my "hobby" - except for school vacations...It's was a long summer, but now I have most mornings free to dress in the lingerie I enjoy so much. I seem to be much more productive doing housework when I'm dressed.

I didn't start untill my wife and I began surfing the net, about 12 years ago.
We both realized that we were turned on from seeing "GUYS" dressed up.
We have slowly progressed from wearing her panties to her buying me full outfits. Just began wearing make-up recently.

I was about 8 or 9 when I started to cross dress and it was my moms panties then it went to her stockings and her girdles I now dress every day and I love it.

I remember telling a nieghbor lady that I wanted to be a girl at 4 years old. I didn't start to try on cloths til I was 7.

I started with my mother's things at age 9.
Felt wonderful then ,still does now

I toyed with it - trying on my mom's half slip, around age 5. Was seen & spanked.

Fastforward to age 14. My mom had died when I was 12. I stumbled across a couple of her dresses and a pantsuit of hers in a box in my Dad's garage. A flood of memories followed. I had to try them on... kind of like a part of her was with me, when I was wearing them. From then on, I sadly was in an all male household. I was very close to my mom, and never close to my Dad. My dad would be bigoted about it, so I would not let myself be seen. Anyway, that was my beginning...

NaomiLynn

I was always jealous of the cute dresses my sisters got to wear, I played dressup with my sisters when i was 8 and tried on my older sisters slip and school uniform about the same time..The first time I put on the dress it felt so wonderful, I loved it and knew I should have been a girl
Jennifer:love:

I first wore pantyhose when i was nine or ten, But i didn't cross dress till last year. For some reason I've had the urge to be a woman since i was about eleven or twelve, But i am not bi sexual or gay. It's a strange world.

When I was home, I would go into a storage closet where my mother left the clothing that was to be thrown out of given away. I particularly liked her girdle with suspenders, but I needed to go to her bedroom to find the stockings. If she ever found out, or guessed, she never let on. In those days it was pubescent fetishism, but as the hormones declined it has become a way to relax, regenerate and focus.

During the first thirty(!) years with my wife, I would use her clothing while she was gone. After I came out to her, she insisted that I get my own things, and she even helped me shop for them.:D

I really can't remember much before I started wearing my older sister's clothes. I distinctly remember being 3 or 4 and trying to pee standing up while wearing a white crinoline with lace and pink ribbons. The reason I remember it so clearly was it was also the first chubby I can remember having. hmmmm...

We moved around a lot when I was a kid and for a while I was my older sister's only friend/plaything. She used to dress me up in her clothes and make me play dolls with her. "My" Ginny doll had red hair. But before we blame her, I know that my Mom lost two babies between us, and that she was taking synthetic hormones to help her hold the baby who turned out to be me. But before we blame her, My Dad also was a crossdresser (although I didn't know this until I was in high school) and his twin sister was/is gay. And there must be some way to blame Adlai Stevenson... :tongueout

Actually, I'm kind of glad I turned out this way...it would be sad to go through life and not enjoy feeling pretty once in a while.

-jj