When did you first crossdress?

Probably around age 12. Stuffed my mother's bra that was in the dirty clothes basket.

For me i reckon it was early teens raiding the washing basket! :)

For me it was when I was about 16. Just one dress in the bathroom. it wasn't until I left home and got my own place that I really started putting on more things and it has just got more and more as the years have gone by. The first time I actually did the whole thing with full make up, shaved body, wig, painted nails, jewelry, stockings, basque, panties, high heels and not forgetting perfume was about 5 years ago.

Lucy Lou xx

Nadina, totally agree with that. Panties and stocking and suspenders and a short skirt. Wonderful. Lucy Lou.

I was real young in 3rd grade I thought about it but really didn't get into it until early teen years and when the 20's hit I went all out wig falsies out to the clubs had a great time but now it is when I get time which isn't often enough.

Beginning of this year! Fell in love with my gf's skirts ... Then I bought some pantyhose and a pair of heels ... fell in love with pantyhose and heels even more ... then, soon the whole package came along.

I've only recently started explore this side of myself because of numerous reasons, but I can remember trying on girls clothing when I was at least four or five. It got severely repressed by my family so I'm letting her out finally.

Second or third grade. I spent A LOT of time in my mom's closet!

First time I fully dressed up was a year ago when me and my bestie went shopping for clothes and oh did it feel so liberating!

I used to "borrow" control top pantyhose from my mom and then wear my sisters bras and panties. 1979-1984. 11-16. I was kind of a devious child and teen always curious but something definitely stuck when I first started cding. The emotions and feelings I felt the first time have consistently always been there I just needed to explore the other me who has been repressed for so many years.

My first time was losing a bet with my wife. Don't even remember what the bet was but she had me clean the house with a maid outfit, black tights, and heels. It felt great

It was 3 years ago, was more of a drunken dare (with the girlfriend of the time). Who knew it would blossom into something more?

I was about 6 years old, I was in my mothers bed room and I saw this lovely yellow dress hanging in her closet, for some unknown reason I just had to try in ,on. When I put it some force came over me and I can still remember it like yesterday, it felt so comfortable, it felt like it was made for me?
Returned the next day and tried the same dress on, again and the same feelings, this is wonderful I thought. Then my father saw me and I knew something wasn't right, dad came in and explained to me boys shouldn't wear dresses. I listened to him, took it on board for a week or so, and i now knew not dress while he was at home, when he was at work I was back into the closet to try on another dress,same wonderful feelings and since then ive been hooked!

If only my wife would manage to win a bet like that, I would be in heaven

I first started dressing when I was in 5th / 6th grade. I would try on my mothers things, yes, much to big, but still very thrilling. I finally found the courage to get my own panties and girls tshirts from the local Woolworths and it all grew from there.

Hi Leeann,
I started to dress later in life.i was in my thirties.i met a woman who wanted me to try on her clothes.i did and I was hooked.i have been doing it whenever I can ever since.My next step is going to be going to lunch with a man I know while dressed.i need lots of tips on make-up and removing it(I am married and need to be discreet.)I have had pics. taken of me dressed;but not in a passable mode.
thanks for the post,
karen

Mid 20's.

I was about 6 but I remember it well, because I was caught.

For some reason I was alone in my sister's room and saw a pair of pink sandals (my sister was 11 at the time, and the sandals were VERY girly). I just felt like trying them on and it was so magical, so different from my boys shoes. One thing I loved was the fact that it had straps and buckles, and they were the very reason I was caught.

So while me and my boyish feet were enjoying this nice pair of pink shoes my older female cousin called me for lunch from another room and I tried to remove them desperately, to no avail. It was hard to unbuckle them. My cousin then walked in my sister's room only to find me nervously trying to take off the sandals. She looked at my feet, didn't say a word and just left. I managed to take them off seconds later and then went to have lunch.

I think it's funny that I was caught right at my first time. My cousin ignored this and never said a word about it to me. Oddly enough, I totally ignored female shoes for many years, focusing mostly on panties, shorts and tops. Now I love them. :battingeyelashes:

Saw some of my moms pantyhose hang drying in the bathroom as a kid and tried them on. I fell in love with how smooth and silky they felt.

I was nine when I started to secretly wear my sister's panties. My sister Sue was a year younger, but nearly my size in everything! Initially I used the laundry hamper as my source of her underwear, but freshly laundered panties from her lingerie drawer were better still and offered the opportunity for some choise in both color or fabric, as opposed to the "panties du jour" that the hamper allowed. I would sneak on a pair of her panties whenever I found the opportunity, wear them all day and deposit them in the hamper without anyone's knowledge, or so I thought.

WOW! most people started dressing very early in their life! I think I missed A LOT on that! well I shaved my legs when I was 15 didn't know why I'm doing it but I liked it! does that count? didn't wear any women clothing / makeup until I was 25. Started by wearing girlfriends panties and bras.

Katie x

I guess my first post here should be about the first time I started cross dressing. I had to be about 11 or 12 when I first started trying on clothes in my grandmothers upstairs room. She always seemed to have nice summer dresses she would pick up at sales. I tried them on and would look at myself in her mirror and imagine I was a southern belle. I started trying on her pantyhose around the same time. There was not a weekend that went by that I did not spend time there dressing and playing around with her clothes. I've been wearing pantyhose and tights on and off now for 35 years and love every minute of it.

was trying on a pair of tights for me, gave me an instant hosiery fetish.

I was probably around 8 or so when I first crossdressed. While home alone, I tried on some of my sister's clothes. I liked the look of them in the mirror and it was a great rush of fun. I didn't really get semi-serious about until later in my teenage years though. I remember always having an interest in feminine clothing.

When I was a freshman in college, I tried on my gfs panties for the first time...and subsequent girlfriends panties :D It kinda just went from there.

I have to say that it was in my mid teens, my dad's ex girlfriend had great taste in eighties fashion. She had lots of clothes she didn't wear in black bin bags. Thus were easy to borrow and return without to much issue