So, how many years now?

64 years, started at around 5.
A friend and i were playing her room one day and we exchanged each others underwear and panties we were wearing.

73 years ��

Many years ago. Started around age 6. Rainy day, next door sisters invited me over to play games, whish turned into dress up. Initially, no internet until they suggested I try on nylon stockings. It was like a bolt of lightning. I was immediately hooked. Now retired with a supportive wife, I?m so enjoying dressing most days. It?s been an interesting journey.

First dressed in women's clothing when I was about 5. So 48 years for me.

About fifty years for me.

Has to be close to 50 for me as well. I'm 54 now and I was probably between 7 and 10. It started with my mother's old dance leotards, one piece swimsuits and pantyhose.

I think I first tried on a bra,tights & skirt around age 10.....then occasionally into my early twenties. Then it all went on hold for several years whilst with a girl friend but started again after moving in with my (now) wife about 25yrs ago. I was about 32 when we got together. I came clean not long after and she's totally accepting and supportive now. I don't go out dressed or made-up, she likes to keep it for her eyes only.....fine by me.

The no-looking-back, Michelle? that?s what I hope always for my CD self. So enjoy seeing you express that. Love, Ann.

I guess it has been about 45-46 years. Started when I was 11 or 12, if I had a sister I might have had an opportunity to dress earlier.

My earliest recollections of my crossdressing (formerly know as transvestism) date back to 6 or 7 years old. The first female article that drew my attention was mom's pink control panties. Whenever I saw it hanging on the clothesline, I could not resist putting it on. From there, my exploration branched out to slips as well as girdles and stockings. In the '50s and '60s, the lingerie pages of Sears, JC Pennys, and Montgomery Wards catalogs also proved to be tantalizing reading. Thus, my interest in and wearing female lingerie has continuously spanned 73 years of my life!

I know that this has always been a thing (curse) for guys for eternity, but we are part of the Information Age and I can’t but I just sometimes wonder if the media (aka programming) has anything to do with it Or was I predestined to have an interest in advertising directed towards a female demographic. For me,I still don’t understand the longing for femininity that has always been present, but I do find peace when I relinquish my reservations.

I forgot to mention how long. Probably 55 years that I remember.

Started around 5 or 6 but that was very infrequent until say 12-17 years old with lots of wearing many items of my Mom’s and 2 older sisters who were out of the house for college and life by that point. Then a lull for about 6 years and decades of say quarterly or more reasonably quick sessions with minimal items of my own, mostly ill fitting items of my wife (wasn’t as fun and was disrespectful to her). Really started in earnest almost 3 years ago now with properly fitting everything of my own and growing wardrobe.

Thus a realistic answer could be 3 years or technically about 52 years.

Very interesting thread with so many commonalities and SO many years!

Right around 50 yrs for me! Hard to imagine it has been that long!!

Close to 55 years for me. Starting around the age of 10 with a few years of hiatus in between

Young, ever so. Early grade school my Grandmother would give me knee highs to wear. Later sneaking in Mom's drawers. Sisters ballet outfits. 55 today and watching the snow fall outside in heels, shiny tights and a lovely shiny black long sleeve fit n flare dress. So close to 50 years of wearing clothing made for women.

remembering back to a dance costume at about 5, it must be 75 years.

I think I started around 2nd grade, so that would be about 8 years old. My parents were square dancers and my mom had a yellow dress with white swiss dots on it and a big fluffy petticoat. So that?s about 50 years for me.

72 years and still going as strong as ever

Give or take, 60. I was about 7 when I wanted to try a dress on (it didn't fit). Was envious of the boys who got to dress as girls for Halloween. I still am. I got my turn in 8th grade, then had a few chances in my 20's.

Finally in 2016, after a few times out, I got bold and dressed for four days straight. The toothpaste was out of the tube and has never gone back in. I get to do things dressed I never imagined in my wildest daydreams.

55 years

20 years this month since I joined this site

Since I was about 14 (50 years ago).

41 or 42 years now, with some long dry spells in between

I'm a late bloomer, not discovering the woman within until my 50s. I've declared that Vivian's "birthday" is the day that I ordered her first women's clothes, so this April she will be turning eight!

Over 50 years now!

About 50 years ago, started with Moms pantyhose and lipstick. Increased when I lived alone. Increased more in marriage. Now at age 59 every day I dress partly feminine at least underdress or dress more completely in private.

I am at 66 years dressing. Started at 7 and will be turning 73 shortly. Sigh?.

Playing dress up around age 5, would be 45. A few momentary experiments with my sisters dresses around 12 could be 38. But really understanding that I wanted to and actively, regularly dressing it is just one year since I realized this is a part of who I am. It?s been a REALLY great year in that regard. I like myself so much better as I have come to accept this side of me, and oh my God how good it is go feel pretty when I can. Being in girl mode makes me so happy.

Started around 7 years old in some form or fashion

I'm 67 now.

I have been experiencing different crossdressing situations since childhood but it is just last 7-8 years that I used to dress from head to toe as a woman almost daily. I am almost 60 now.

I only have vague memories of the early years. I was fascinated by my mother's clothes. Sometimes explored the dirty clothes hamper.

I have been a crossdresser to some degree for 65 years.

Since I first wore Mom's panties and bra it's been 70 years.
Since I first had a complete outfit of my own it's been 58 years.
Since I first went out in public fully dressed it's been over 20 years.

It's been a long ride and it's not over.

It's been about 60 years for me from trying on Mom's panties and slips. I'm certainly glad that I have my own extensive wardrobe now.
What continues to amaze me is how similar we all are in this regard and how that desire never really changes throughout our lives.
Bravo for us!

I'm approaching 78 in a few months. My parents almost caught me wearing my mother's dress at age 18, so that makes it a minimum of 60 years. However, I was into my mother's drawers for many years before that. I'll even not count when I had to step on top of the edge of the bathtub to take her slips off the drying rack over the bathrub, so, realistically add another six years.....maybe 66 years???

With all of your responses, now I know that I was not the only early teenage boy playing with Mommy?s panties back in the 60?s.

70 years for me, officially. I started dressing at 7 years old.

About 45 years since that fateful day when I first put on a bra.

About 20 since my first lingerie purchase - I didn't crossdress for quite some time because I was in denial.

60 ish. But does it matter. As long as I have memories, they have included cross gender issues. We are who we are. There is always further to travel in life, but enjoy what you have, until you get there.

I started at 3 with nail polish, so 73 years. I didn’t fully dress until I was 12, so 64 years since then. I was in my mid 50s before I was able to fully accept myself, so about 20 years since then.

For me it's 70 yrs but the last 8 months I have been transitioning

55 trips around the sun, it came on at age 8.

Sixty years. I dressed as a peasant girl, maxi skirt with off the shoulder blouse, at Halloween at age nine. The idea of dressing had been rattling around in my head since age five.

I wore my first item at 6 , and I am 58...that is a long time.

It would be 57 years for me. Went as a girl to Cub Scout Halloween and have been hooked since.

About the same, if I count trying on mom's clothes when I was 8-10 years old. But I stopped in my early teens, and didn'rt resume until in my 50's.

About 67 year. Came out to my wife a got serious in 2005

Started at 8 years old now 46 years old, 38 years

For me since 1982 so 43 years now and January 1st of 2025 I?ve been out 24/7/365 dressing I finally got the nerve up to be out and no problem?s at all and I go everywhere. I?ve been out 2 years 4 months now

I started with high heels from the toy box, but I really got hooked hard when I was 13 and I stepped into my mom's pantyhose (wow!). Therefore 54 years!

I am at about 23 years of dressing. I started in 2002 when I was about 2 months maybe into my 8th grade year of school. It?s been a wonder adventure to be on.

From the first time I put on a pair of panties, until today, we're looking at 49 years.