how old were you?

I must have been about 7 or 8 years old when I first tried on a pair of my mother's tights and a long pleated skirt. Oh my. But I can remember wanting to wear my friend Rachel's clothes years before that. One morning we were in the garden before school (infants) and she was wearing a pair of black patent MJ school shoes and white knee socks. I remember looking at them and thinking that I'd love a pair of shoes like that. I must have been 4 maybe 5 years old at that point. The desire to dress has never left, although my tastes have evolved over the years along with my age.

The first time i remember trying on women's clothes, were my mom's when i was about 12. The opportunities and desire to dress up largely disappeared until i was in my mid 20s, when someone left a couple pieces of clothes in an apartment laundry area. I "borrowed" them and wore them around my apartment for a few days before returning them to the laundry room.
After I got married, i occasionally would try on some of my wife's clothes.
Then over the last 6 months or so, I realized how much I want to be able to wear women's clothes. I currently sleep in a nightgown, but haven't pushed that boundary.

I used to try and get to the nursey school first, so I could wear the brides dress. I'd be 4 years old

I was 23 when I finally came to terms with the reality that this was part of me, and wasn't going away. I hadn't dressed in a couple of years due to a girlfriend. She expressed a desire to see me in pantyhose. I asked her about that recently, some decades on, and she doesn't remember it! Anyway, with the request I went and bought myself some pantyhose, came home, and put them on in preparation to going over to her place. The impact on me was...intense. I'm not talking about outward physical reactions. I'm talking about in my soul. I felt it in the very fibre of my being, and couldn't believe what I was feeling. I'd been dressing since age ~8, but this was the first time I had to admit it wasn't just a curiosity, a phase, etc. This was me.

That's when the real struggle of self acceptance began. Before that, I didn't have to contend with it being something I had to accept.

Never really had an inclination until my 40’s.
Now it’s becoming a serious pursuit at our house

I first started when I was about 10 yo, finding som old clothes from my mum stored in the attic. I remember a couple of swimming suites, a bra and a slip which I stored in my bedroom and used in my first years of dressing.

I started when I was 12 years old. My older sister and her friends would dress me up and treat me like one of the girls. I never told them that I enjoyed every minute of it.

When i was 13 my cousin was going to the local collage and my family lived on the bus route so she stayed with us . One day i saw her thow out a couple of bras and some panties . She is a smaller lady and what she threw out fit me perfectly . I snuck them out of the trash and tried them on and was in love with them . Had them for many years even though they became to small for me to wear .That was the 1970s . After the internet became a regular thing i bought some new ones . I love wearing bras and panties Even though my wife hates it .

As soon as I was old enough to be left home alone for a few minutes, I ran into my mother's and sister's room like in my dreams.

I was maybe 8 or 9 and it's the most beautiful experience. I'm glad I get to enjoy it but I'll love to be able to share it with the people I care. Maybe someday.

Actually, about my current age of 76. I didn't start wearing panties and stockings until age 74. About 1 month before I turned 76, I began wearing bras and dresses. I'm a late bloomer; but, I love it. I have completely accepted this part of me and relish in it.

I was around 10…maybe 11 years old when I started dressing. My first attempt was in panties and a pair of thigh highs. It quickly escalated to full dressing and makeup. I will add that even though this is when I officially started, I do have a memory from around the age of 5 or 6 that I remember. My mother has a plastic bag full of stockings. One evening while she was watching TV in her bedroom she allowed me to try on every stocking and pair of pantyhose in that bag. I have no recollection as to how or why it started, but it is something I have always remembered.

I think most of us started when we were quite young.
Then later in life we realized that this is how we will always be and it's who we are. It's a now of never sort of thing to much more fully explore one's female side.

Personally I "started" when i was 7 years old. which was about 1954. .I had a older and younger sister, Yes, I was a middle child.

It wasn't until much latter in life....in my '60s that I finally admitted to myself that I will always be like this and started to more fully embrace it for the most part
With no family in the area... and my few close friends have all died or moved away.

With a passable trim female type body, I now go out in pubic as Barbara quite often.... like shopping, going to movies etc .I almost always wear a skirt or dress.
I am now 74 years old and thankfully in excellent heath... and blessed with full head of long (grey) hair.

I try to be kind to all I meet an find that most everyone responds favorably to kindness. :)

Until I was about 4, I had never seen a girl. All the kids in my street were boys. Then a new family moved into the street. They had a daughter about my age. When I saw her for the first time, she was wearing a dress and she looked so pretty. I wished I looked like her.
Shortly afterwards, my sister was born.
By the time we were teenagers, I discovered some of her clothes would fit me, and I tried them as often as I could. Ever since I was 4 I knew I wanted to wear pretty, girly clothes.
Finally. I could, but it was my guilty secret.
By my 2nd year at university I was living alone, so I was able to obtain my own clothes and dress whenever I wanted. This was the time when I knew it was right for me, and my guilt disappeared.
That was in 1982, so I've been comfortable with it for 40 years now.
But such is society that most of the time I still have to hide everything.

Ive known this was who i am, all my life. ��

Wore things since I was a child but didn?t wear makeup, wig and heels until about 10 years ago. Mid 30s.

I started dressing in my childhood and knew right away that there was something different about me so I guess I always have known who I was.

Early forties. My first toe-dip was in my early teens but I was in my thirties and already one purge down before my first time fully dressed and made up (I didn't want the day to end). After a second purge, quickly followed by regret and grieving for lost garments, I knew Fiona was a fixture. I still worry about what might happen if she's discovered but I embrace her now and enjoy being her. And no more purging!

I dabbled a bit all throughout early childhood... trying on my mother's wigs, shoes and jewelry. It wasn't until I was maybe 11 or 12 when I finally had the house to myself alone all day that I went all out with the makeup and clothes. Seeing the transformation in the mirror was... well... transformative for me. On the one hand, I felt I finally had proof that I was born in the wrong body, but on the other hand I knew there wasn't anything I could do about it.

I don?t remember how old, maybe 11 but it was before I really knew much about what anything sexual was. I was alone and able to put on the bra, girdle (yes it was that long ago), stockings and heels for most of a day. I did this sporadically until I became interested in girls.

I really didn?t do it again until mid 20s while living and working far from home and anyone I knew. Had there been an internet back then I would likely have done it more but again sporadically until my late 30s

I started dressing when I was 12 and have done so on and off over the years. I'm 56 now.

I shared my answer in my introduction, but I think I was roughly 5 or 6. My Mom stored extra clothes in my bedroom closet and one time out of boredom I put think I put on a skirt. I actually got an erection and had no idea what was happening. I later mentioned it to my Mom and of course she immediately moved all the clothes elsewhere. I have two older sisters that I grew up with and when my parents divorced I was in the 2nd grade.

When my older sisters went off to college I was in the 6th grade. My then single mother was working full time to support us and thus I would come home to an empty house. A house which had a LOT of women’s clothes in it and as I aged I experimented more and more until in High School, if I didn’t have any plans it would be almost daily. For me is started as very sexual and every session would end as you might think under the teenage years.

Even now there is a strong possibility that a “session” will end by masturbating due to the immense feelings the clothes make me feel. BUT, lately I have had more frequent, but shorter sessions and not the time or effort to finish. Hmmmmm. I need to add to my post count so I will probably create a new thread, but I am interested to see what people think about low Testosterone and it’s effect on cross dressing tendencies and why guys in their 50s (I am 55) tend to increase or get more involved in cross dressing at this age.

I was 13 and had just started to go through puberty when I began my CD journey.

I was 11 or 12 when I found the joy of wearing my moms dresses and slips. Then through out life I would put on anything femme I could. This year I am 52. Jade became real and she has her own clothes. Nothing borrowed.

I was in Nursery School so I think that would have put me around age 3. I also knew that is was something I needed to keep my mouth shut about, because I knew it wouldn't go over well with the adults.

Started around 12 with Mothers pantyhose and makeup. Tried to hide but was disovered many times over 30 plus years of marriage. Told my wife in 2018 at 53 that I am gender fluid and wont lie or hide my crossdressing from her anymore. But she doesnt like seeing me wearing feminine clothing. I epilate and love having smooth skin, love wearing panties, pantyhose and sometimes a little lipstick.

Guess I have know since I was about 5 or so. There is a lot of conflict about my early ventures into the world. Some i don't wish to bring up here, but I remember my brother who was stationed in Vietnam sent home a Vietnamese doll. She was sort of a "spy" that would try to make my GI Joe talk. She had a tight blue asian dress long black hair and high heels. I guess I sort of identified with her. Flash forward to about 13 years. I found some sexy vintage Merry Widow undergarments in the attic of our new house. I love putting those tight corset like garments on in the bathroom. I would be my parents would wonder why it took me so long to take a bath. I have been crossdressing since then.

I was 9 when I tried on my moms stockings and slips. Hooked from then on.

I'm someone who's relatively new to CDing, but browsing threads like this one do bring to mind episodes in my distant past when I was unwittingly introduced - and attracted - to the sensory joys of what is now known (and celebrated!) as crossdressing.
Like many of you, I was always envious of the fashions available to the women and girls in my life, and although I never acted on that feeling, I suppose I always held some deep subconscious desire to "look like them". I also have a tall, slim build that in many ways lends itself better to women's clothes than to men's, and now I'm dressing more in ways that really do improve how I look and feel.
For most of my life I wore baggy, oversized clothes that were certainly comfortable but looked ridiculous on my slight frame. BTW, I'm 5'10" and 140 lbs. and can easily fit into a size 6, sometimes even a 4.
Several years ago I read an article about how women's jeans fit much better than men's jeans on people with my build. This piqued my curiosity, and off I went to the local thrift store and bought three pairs of skinny jeans.
The fit and feel of them was amazing, but most of all I loved the feeling of being somehow "transformed"!
One thing led to another, of course, and here I am today, fashion liberated and enjoying this experience with all of you. Where it will ultimately lead me I really don't know, but so far it's been a most pleasant and satisfying journey.