What prompted you to start crossdressing?

The truth is, I really don't remember what prompted me to start crossdressing, but what was the case with you? (if you remember!)

I can't point to any particular event or trigger. I can just recall even as a young child of 6 that I wished I could dress like the girls. Never wanted to actually be a girl, but just to dress like one.

Nothing prompted me per se. I just started doing it and it felt right some 57 years ago. :battingeyelashes::)

Curiosity. I recall being 8 or 10 yrs old and trying on a discarded one piece swimsuit one of my sisters wore. Been hooked ever since.🌺

My mother.

I was in a bar. I was 17 years old. I saw a girl who I found to be attractive. Suddenly I felt a sense of wanting to BE her, rather than be with her.

thats a good question, my oldest memories of it are probly around 4 or 5, what makes a 4 or 5 year old do that?

I completely understand. I size women up - their makeup, nails, clothes, heels, everything - and want to be them and have their boyfriends/husbands!

I have a pretty specific memory of the first time. I'm not sure the exact age, but something like 11 or 12. I got up in the middle of the night to use the bathroom and a pair of my mom's panties were sitting out. I was curious and decided to try them on.

I often wonder would any of this have started if not for that moment? Or was I destined to come around to it sooner or later?

I was born a cross dresser. Opportunity is what prompted me.

For me, I was attracted to women's clothing when I was real young not realizing why. I remember trying on my mothers shoes. I was always attracted to the female clothing in the Sears and Penny's catalogs. I remember pestering my mom for a boy's nightshirt(which I got) which was like a nightgown. When I hit puberty and the hormones kicked in, I started with women's underwear and it went from there because it felt like the natural thing to do.

Yep- loved to dress in her lingerie and clothes - lipstick and everything. Completely fascinated with reading my mothers Cosmopolitan and Playgirl magazines - and romance novels - in my teens.

For some reason I put on a pair of hot pink satiny panties ang the gates opened.

I'd say I'd always wanted to dress. I always admired them, and wanted to be just like them.

Hi Tabatha :hugs:, I'm 73 and I've been in this program for almost 69yrs. ,

I guess at the time it just seamed like a good idea...:daydreaming:...

Hi BLUE!

Wow! Long time! Only 24 years for me. I am glad I found this site because I have often felt like I was getting older now and often wondered how much longer I would still enjoy dressing. But there are many members here a bit older than me that give me hope that I will still be able to enjoy dressing for many more years to come :-)

The feel of Mother's slips, hose, and heels.

My mother gave me panties to wear when I was 5.

As a young boy I always envy the girls and what they wore little dresses with pettiecoats and MaryJane shoes, one day my aunt noted how I watched them and asked me if I wanted to try one her friends daughters dresses on of course I said no but the next day she asked me again and I said yes I did and have been dressing ever since, I now thank my aunt for the many times I dress and the felling of freedom it gives me.

That's so cool, Terry!

The feel and look of the Women's cloths back in 1970. Never thought about dressing in them until after a fixed bet, it seems that it backfired and the results lasted from that first occasion. It is more of a fetish but one I have endeared and use to my advantage. And it is not confusing I enjoyed it and still do and expect to as long as I possibly can.

for me it was trying on mom's high heels , i was hooked after that :)

Its a big part of who I am. I just wish that I could dress more

For me it just seemed right.

Always wanted feminine clothes.

I can't remember any single event, but I remember little bits and pieces of when I was 6 or 7 and having to try on a skirt or dress and sneaking off to the bathroom and trying on things from the laundry basket. This urge never went away and I bought my first bra at 14, after trying on several of my cousin's bras and realizing how right it felt. Now that I'm 50 it is just who I am.