When did you first crossdress?

[Rachel292]

I'm not sue, it was either my yonger sister's checked mini skirt or my mum's green tight skirted almost backless 1950's/1960's style dress. It must have been mid/late 1960's when i was about 10 or 12

[Barbara Jo]

I was about 8 years old back in 1955 and had a younger and, an older sister who was about 4 1/2 years older then me.
Yeah, I was the middle child with two sisters.

I began to wonder what it felt like to wear all those feminine, '50s female clothes.
So, one day, I put on one of my mom's nylon panties and full slips.

I was hooked and soon began to also try on my older sister's things as she got into her early teens and began to get very feminine grown up lingerie and other clothes.

[Annette_boy]

Hi everyone

I was 5 years old (in 1950) when I first tried on a pair of moms Panties they were nylon and felt real silky I was hooked from then on in 2006 I went fulltime and have not worn male clothing sence

Hugs Annette

[Princess_pantyboy]

I think my mom put me in girls clothes when I was small because we had some hand me downs and she said I was two years old, and put me in a dress and brought me to the mall.

[Xandra]

Thanks to everyone for the responses. I am so loving reading about your memories. Keep 'em coming..

[Kit]

The first time I completely dressed was at an anime convention. I build myself up to it for like 6 months, getting the costume and wig together and teaching myself makeup, how to walk in heels and other tricks, but that was the first time I felt complete lol. I was so damn nervous and almost didn't leave the hotel room about 5 times but I was finally convinced to, and within the first 10 minutes got some cool responses so I ended up having a blast have loved it ever since.

[timbertv]

I remember being in 8th or 9th grade and watching a talk show during the summer and seeing Rupaul and decided to go get some of my sisters clothes and try them on.

[lovetobedani]

I can remember back as far as when i was about 4 playing with and trying on my mothers bra and heels. A friend of hers was over and saw me and commented on how cute I was to want to look like my mom. Then I looked at lingerie ads in publications and wondering if I would grow up to look like this. Nothing was ever said to me about either. Maybe thought that I was just too young to understand. This was in the late 50's. It wasn't until I was 12 almost 13 did I dress fully. I have no idea why. It just felt like the right thing to do. From that day on I get the most wonderful clam feeling as if this is the way I was meant to be.

I've always been jealous about how many different choises women have in clothing styles and colors. Men have a basic and limited choises that's not diverse enough for me. I once told this to a GG I was dating and she told me that she would teach and help me dress if I wanted to. Like an idiot I said no hiding for the fear of being humiliated for what I've been doing for years. I look back on this as one of the greatest mistakes I've made in life.

What I find the most amazing is so many of us have the same past from the time we experiemented at an early age to looking forward to the hamper, bathing suits and lingerie hanging to dry in the bathroom when we were in our early teens.

[Peta-Downunder]

I have always had a thing for satin and silky fabrics for longer than I can remember, I guess my main source of that was woman's clothing an mainly underwear and sleepwear and progressed from there. Wasn't until my late teens I was in a position to start my own collection.
Now just shy of 40 I only just got my first wig, make up, and shoes that fit in the last month or so as I am now living alone and can have this sort of stuff around Been shopping online now too building up a collection.
First time I got myself funny done up it just felt terrific, one of the best things ever!

[DorothyElizabeth]

Here's a little essay I posted on another site a little while back.

Feb 2005

So, when she left, I was devastated. I felt so ALONE – so vulnerable. I’d come home from work to an empty house. I wandered from room to room, searching for - for what? For her. Not just some sign of her; they were everywhere. I saw them in the rooms where we had sat and drunk coffee together, in the kitchen where we cooked, and ate (both food and each other) together. NO, I wasn’t looking for signs; I was looking for HER.

It took a year or two, and I finally got used to living alone – well – not really – used to the feeling of emptiness. And I no longer missed her, specifically – I just missed having a woman around. Then, one day I got a call to go play Cabaret.

In Cabaret, the orchestra is a part of the show; they are all supposed to be musicians in over-the-top drag queen outfits and makeup. I was a little leery, having never cross-dressed – well, not since I was a very young child, playing dress up. But the gig paid $350.00 for two weekends performance, and two rehearsals, so I accepted.

At first, it felt strange, sharing the dressing room with strangers of both sexes, but there was a certain decorum. Of course we all looked at each other, but there was no open staring, and no gesticulation or even raised eyebrows. By the third performance, we were used to seeing each other nude, and began to be a little more relaxed about our sexuality. Clearly, it was not something that could be ignored entirely – but we laughed off the occasional erection (over either men or women) and we all became more like siblings than couples viewing each other as potential sexual partners. (Though there was a little of that going on between some members of the cast, in a reasonably discreet manner.)

But the odd thing was, one night the power went out just as the final curtain went down. Emergency lights came on, and the audience vacated the building in an orderly manner. But we who were in costume and makeup couldn’t see in the dressing rooms, to wash the makeup off, and couldn’t see to sort out our clothing and such. So we all decided it was easier to drive home in costume, and change there.

When I got home, it was like a light bulb went off in my head. Suddenly, there was a woman in the house. It felt right, somehow.

I have been “dressing” ever since.

I rarely go out dressed; I don’t care to bother with all the makeup and such that is necessary to “pass”, and there are too many people in this essentially rural county who know me from the years I spent working for the local government. But I always “under dress”; I no longer even own any male under clothing, except socks. In warmer weather, I only wear a bra if I am exercising (I need a sports bra, to keep things from bouncing and hurting – a by-product of testosterone blockers I take for my enlarged prostate) or wearing a suit jacket or blazer. But in cooler weather, such as we are having now, it is easy to hide the telltale straps and clasp under bulky sweaters or a down vest (purchased online from the “Women’s Outerwear” section of Lands End, thank you very much). No one has ever noticed that it closes the “wrong” way; or if they have, nothing was said.

[Zimri]

College! Found myself with the keys to the theater department's costume storeroom. A world of exotic clothes, shoes, corsets, you name it... no turning back ;-)

[Xandra]

Delightful :-)

College! Found myself with the keys to the theater department's costume storeroom.

[Shadowgirl89]

i must have been about 7/8 years old i remember seeing a pair of my moms panties they were white satin bikini with little red roses on them i love the way they felt and i had to try them on and it was one of the greatest experiences of my life

[FairyLink]

When I was a little kid. Not sure what age. Under 10 though.

[JazmyneCD]

I was definitely under 10 when I first tried on a pair of knee highs. I loved the feeling and eventually graduated to pantyhose. Of course, I'm still doing it as well as a handful of other girly things.

[AKADonna]

When I was about 12, my parents would go out every Wednesday night to play cards, leaving me home alone. Well, after rummaging through my Mom;s lingerie drawer one evening and trying on one of her Playtex bras, I was hooked. Wednesday evenings became "play night" where I would dress up in all sorts of girdles, bras, longline bras, strapless bras, slips, dresses and heels. I stopped it when we moved about a year later and didn't resume until I was more than 50 years old. I've since been dressing for the past 20 years!

[Annaliese2010]

My sisters panties when I was a little kid.

[lisagurl]

my aunt dressed me up as a girl, then i went home and began to wear my step mom panties i started at like 10 or so

[Milou]

I started when I was 13 and quitted for around 10 years. Even though I'm alright, I had my fair share of guilt and anxiety. I will probably crossdressing in March and hopefully I'm able to accept and love myself.

[deevon89]

My cousin completely dressed me when I was 7 and I mean top to bottom purple silk panties purple bra cute lil flower dress curled what little hair I had and full make up and nails .... Best feeling of my life

[FeliciaCDSNJ]

There's dedication for you. Luckily I was never caught. :-)

I was caught numerous times, from my hidden stash to me actually wearing the items of choice but that never stopped me. :-) Even now, I own no male underwear and restarting a wardrobe that was lost to me due to an ex abandoning our old apartment when we went our separate ways.

[prettygirl4]

It was probably elementary when I secretly tried on my sister's clothes. However, as young as 5 I was always envisioned myself in a wedding dress one day so I always sort of knew. Did it secretly for a few years and now it's all I wear. I've thrown out all my men's clothes (im now 22). It's so freeing to walk around in what your comfortable in

[CONSUELO]

I have really enjoyed reading this thread. My early cross dressing experiences were so intense and I look back on that time with great fondness. Reading this thread takes me back.
By the way. How does one start a thread?It might seem like a stupid question but I am really not sure how to do it.

[Corrina]

I remember when I was ten. Wearing my stepmoms silky full slip, oh the deposits I left on that!! Hooked for life :-)

[Helen Grandeis]

I was in seventh grade. My parents were out. For some reason after my siblings had gone to bed, I wandered into my parents bedroom and put on my mother's girdle with attached garter stockings. It was surreal. I did a gymnastics move supporting my self on my arms with elbows tucked into my abdomen with my body horizontal. I rubbed my stocking clad legs together. The heady erotic feeling plus the physical exertion resulted in my first orgasm. Thus imprinted, various strenuous positions plus silky stockings reliably produced the same results. For a while, I could also fit into my mothers 5-1/2 pumps in dozens of colors. This carried me through middle school and high school.