How did you start down this road?

For me it was an accident

I?ve told my story several times but I enjoy telling it so here goes. I started at age 3 when I begged my mother to paint my fingernails red. I showed the other kids in the neighborhood and they told me that only girls wore nail polish. I didn?t care. I asked my mother if I could wear perfume, and she showed me how to apply it. I secretly started borrowing her clothes and wearing them. I continued wearing nail polish. My mother was out socializing with friends a lot and my father was only home on weekends. I was left home to baby sit my younger siblings. I would put them to bed and use the remaining time for dressing up. By the time I was in 6th or 7th grade I was fully dressing with bra, panties, full slip and a dress. I got caught with my mother?s clothes a couple times during this period. I made lame excuses that were probably not believed. I think that my parents knew but were too embarrassed to say anything. I found my father?s stash of feminine undergarments once. That?s probably the reason he never talked to me about it. When I was a junior in high school I decided to give up the girl stuff and learn to be just like the other boys. This was pretty much a disaster but I don?t want to go into that here. I promised myself that I would never even think about female clothing ever again. I stopped dressing, but never stopped thinking about it. I looked at catalogs and fantasized a lot. I finally couldn?t stand it anymore. I accepted that I was a crossdresser, and started dressing again. I?ve never been happier.

I think, in my case, everything started with an unconscious desperate attempts to clarify my real gender identification. As a toddler, I had a very pleasant and satisfying dream, so good that I still remember it. I was a naked female in high-heels publicly on a stage... Next, when I was less than twenty, I was lying down on a coach one day and came to a clear conclusion that I would have been much more satisfied if had been born as a girl. This idea is still with me all the time.

i was about 8 or ten i traded clothes with my sister at a movie house ill never forget that feeling of coming down the stairs. i felt like a queen, i felt like the prettiest girl there

It all started with a little girl named Lana! She was flipping her white dress over her head and giggling! I wanted a dress! And so it began...
Hugs Lana Mae

hello Richard,
when I was young I wanted to dress like my hero Robin Hood so I tried on a pair of my sister's tights...
Luv J

I don’t know. Since I was 10 or 11 I wanted to wear women’s underwear. Not having any sisters I tried on my mom’s bra and just knew. By the time I was 14 had some of my own panties that I liberated from a store.

It started at age five when I saw the sister of a friend all dolled up. This was in a long gone time and place when mothers dressed their little girls is frills, ribbons, and bows. I wanted to look that good. I investigated the possibility but I did not like the answers, also products of the same long gone time and place. Nonetheless, I found fleeting occasions to dress, such as Halloween and after work. I worked as a janitor in a small church with a clothes lending closet.

4 or 5. My sister's petticoat called to me. I had to see how it would feel to wear something like that. Later, mom's slips. Over 60 years later I have a large collection of my own.

Innocent curiosity..

When I was about 4 all the kids in the street were boys. I don't think I'd ever seen a girl.
Then a new family moved into the street and they had a daughter. When I first saw her I was in awe. She was wearing a pretty dress and I wished I could be like her.
Shortly afterwards my sister was born and several years later I tried on some of her panties, and I was hooked. As we grew up into our teens, there were a few of her skirts and dresses that fit me and I wore them regularly (without her knowledge).
I used to do a newspaper delivery route. On Sundays the papers were big and heavy so I used to use a closed cart to carry them. One Sunday, one of my customers had put out a large bag of clothes for goodwill. Knowing the family had 3 daughters around my age - one of whom I knew at school. I figured that there might be something of interest in there. As you can guess, the bag ended up in my cart and I finished my deliveries wondering what was in there.
As this was very early morning, I got home before the rest of the family had got up and I was able to get the bag up to my room.
I wasn't disappointed. All the clothes were teenage girl's including dresses, tops, a bright yellow swimming costume, and a couple of bras. Most of them fit me quite well so I wore them as often as I could.

Apologies to the goodwill people, but the clothes did go to a good home (in my opinion).

When I was about 4, I asked my Mom if I'd be like her when I grow up. She said no, boys grow up as men, not women. I was disappointed, since I wanted to look like her, not like a man. I don't know if I thought about that any more. Maybe I was satisfied with my fate. I know I didn't want to be like my sisters though.

When I was 9 or 10 I was in a 4H play, a comedy about a sort of hillbilly wedding. My sister was the best man and I was the maid of honor. The 4H leader had a nice looking fancy dark green satin-like dress she let me borrow. It felt like heaven. I got to practice once or twice for the play and then actually be in it. The following year I made up a play myself in which I played a lady in a fine dress walking in the park past 2 men sitting on a park bench. One was a gentleman in a suit reading the paper. The other was a bum. I dropped my hanky for the gentleman, but he didn't notice. Instead, the bum picked it up and loudly blew his nose with it.

Around that time, my sister had a short green dress like a girlscout dress. One day I took it from her closet and put it on once or twice in the bathroom. Instead of putting it back in her closet, I stashed it under the upper bunk bed. One day Mom found it and when we got home from school she showed it to my sister and both of them then confronted me in my bedroom, Mom asking sternly why did you put her dress under the upper bunkbed. Somehow I quickly thought to say I wanted to see how long before she would notice it was missing. They were satisfied with that answer and didn't say any more about it. That made me very nervous.

I would say you were very lucky. I bet there are a lot more lucky girls these days than back in the 50s and 60s.

So long ago now. I used to dream about being a girl from my earliest memories. I have only sisters and female cousins to relate to. I was always the only boy from my earliest years. We played together as a group of young people. I was simply one of the group. Never really realised I was not just one of the girls until junior school. By then it was too late. Being a girl was simply more fun. Alas my parents and society at that time didn't think the same, so it all went underground. Did me a favour in a way. I know now that I am just a man that was conditioned through fun and circumstance, to enjoy being a women. As a teenaged that was very confusing and I think some modern male tenagers transition when they should actualy stick it out and would enjoy later life more as crossdressing males. But we can each only deal with what we see in front of us.