When did you first crossdress?

[shimmeryphantasy]

Hi everyone... I am new here.... kinda surprised I haven't found this forum sooner, I've been a member of other pantyhose sites for a very long time..... I love love love all the first time stories here!!!! So here's mine.... actually I can't remember mine because as far back as I can possibly remember ...... dunno if anyone can remember before the age of 4 much but if I can remember when I was 3 I was probably wearing my moms big black satin panties , they would almost cover my whole body and I loved how they felt so much I would put them on whenever I could.... as a child I had figured out that one side of the material was softer than the other so I would always turn everything inside out so the softer side was rubbing on my lil pp ....... then I started figuring out that when I would put on her panties and a slip and her long purple nightgown that they would be super super slippery with each other and I would always turn the outer gown inside out so it would become super slippery with the slip....... oooo my ..... after i started figuring this out I had many many fun times trying on different combinations of her many nightgowns ,,, turning them inside out and finding the most slippery way they would slide together..... making my lil pp hard for hours ... I must have been having multiple orgasms all I knew was how super good it felt....... and of course just like pretty much everyone else ,,,, pantyhose were always there.... I wore them every chance I could ... the way the long purple satin nightgown felt draping over my hose coverd legs was so amazing ....... so I have been addicted my whole life........ I'm 48 now ...... over the years I've collected lots and lots of super soft nightgowns, slips , panties, and pantyhose , mostly from ebay in the early 2000s.... Cabernet and Jones of NY are some of my fav brands, but the last few years they have become much harder to find the good ones...... I think back to how good the 100% nylon stuff felt when I was a kid then they started making the polyester nighty and gowns and they were like 100 times more slippery when I would turn the outer gown inside out, some work better together than others ....... anyways that is a little look into what I have experienced .... I love this thread and hope to see more first time stories......

[Terrylynn]

As long as I can remember I enjoyed playing with girls. I loved playing with dolls and other girl toys. Around age 5 my father told me to stop playing with my sister and her friend. I don't recall the reason but I didn't listen. One day he said If I wanted to play with girls that I would have to wear a dress. I think he was trying to shame me into stopping but that's when I made the connection between girls and clothes. After that I started wearing my sisters dresses whenever I could. I love being feminine and can't imagine ever wanting to stop dressing!

[LittleMissJoanna]

I started when I was about 10-11, with my mum's lipsticks, then started playing with eyeshadows, eyeliners, mascara (which I can't get enough off, it still turns me on every time I apply some), then lingerie, then heels, then skirts and then the rest. I then moved away and promised myself to never do it again after I had half confessed to my mum what may or may not have happened, she never brought it up again, I'm not sure what she thinks, maybe she tries to avoid it because she wants me not to do it anymore. I stopped for a while, met my fiancé, then I started cross dressing again, I got my own clothes and make up, then she found out about it and broke up with me, there were other issues but clearly, she wasn't happy about it, she called me a tranny in a derogatory way once and after that we just parted ways, I purged myself like we say. I sold as much of it as possible on ebay and I disposed of the rest, I sold one pair of heels I so miss still to this day, that was 4 years ago. Big mistake since I started cross dressing again about a year or so later, and now I know I won't stop, I am never getting rid of my clothes again, especially since I have an awesome wardrobe with so many amazing items, it's about 4 times the size of my male wardrobe, a bit embarrassing when I had to move the last time, traveling across borders with bags full of female clothing, I am glad I didn't get searched, except for these high heel boots that were in my carry on and got searched because my silly brain had forgotten a bottle of water in there!! Oh well, I pretended it was for my girlfriend, then I had some food coming into the US and ouch, they put them all through the X ray, but I didn't get any comment, only a couple of weird looks!! As long as they don't take them away, I don't care!! Only fear now, will I ever find a woman that accepts me for who I am, I start to doubt this, that's 2 down already and still nothing, no wonder I am a little intimidated by women...

[Paula_Femme]

Only fear now, will I ever find a woman that accepts me for who I am, I start to doubt this, that's 2 down already and still nothing, no wonder I am a little intimidated by women...

Hi Joanna

Don't despair, in my experience the best thing you can do is be honest, both to your potential partner, and yourself, and be open about your cross-dressing right from the beginning.

I met my girlfriend, who's now a member of this site, on a "Vanilla" dating site, and told her I was a cross-dresser in my very first email to her; she's met "Paula," and did my makeup a couple of weeks ago... which was great fun for both of us!!!

Yes, there are many Women, the majority actually, for whom entering a relationship with a cross-dresser is never gonna happen, but there are those who are open to exploring, for whom "vanilla" isn't enough... you just need to connect!

If you'd like to converse in private, just PM me and I'll be happy to answer questions etc.

All the best
Paula

[maxjohnson]

Well it started first with my fascination with panties. When I was a teen, I used to try out panties of my sister and sister in law when they're not noticing. At first I thought it was a fetish, but eventually I realise I can feel natural in it. I don't own any male underwear for years now.

As for full cross dressing, I don't remember, it's nothing special. When I was old enough with my credit card even before I moved out I bought some clothes online and tried then out. It just came naturally to me and I never felt guilt about it. However, even today it's something I keep private to myself, I am straight acting outdoor and have no desire to go out dressed, it never even cross my mind. I'm not into fancy stuffs either, I imagine if I was a girl I'd be a tomboy. However, I have no problem talking about it to my closest friends. I think the two reasons I do it is to get in touch with my sensitive side and stress reliefs. It's really amazing how crossdressing help my emotional states when I'm feeling down.

I also have to add maybe my attraction to aroma and my body shape have something to contribute to it as well. I make sure all my panties smell like flower. I'm quite thin and light myself and I like light clothings so aside from lacking a bosom, which sadden me sometimes, the girl stuffs tends to fit me.

[kaylyn]

The first time I tried it I was eight. I've been doing it on and off ever since. But since about 19 I've been doing it everyday. Well panties at least.

[Eselka]

That would be around 10 for me, and for many years my mum's wardrobe was my playground I couldn't resist the curiosity of trying on skirts, dresses and make-up and I loved it (which really puzzled my mother when she found out by the way)

[Xandra]

I am curious. Is there any correlation between the age at which someone first dressed and the frequency of dressing today? I seem to be dressing more and more the older I get, whereas before it was just at weekends.

[Diversity]

I remember trying on my mom's bra and stockings. She always left her undergarments on display in the bathroom. I believe it was part of my sex education, because my parents never talked about any of 'that stuff'. Anyways, as I sit here tonight, I thank my mom for taking the initiative to try to educate me. She was a wonderful mother and now that both have passed, I miss them more and more, as I realize how much they really did for me.
Di

[Paige62]

i started dressing as a teenager i had always liked girls clothes but didnt know why till i found my older cousins bra panties and a tight mini dress she had put in the washing basket and just looking at it made me so excited and i waited till more dirty stuff was put on top of it and i took it and hid it at the back of my wardrobe and that night i tried it all on what a feeling and knew then i had to keep dressing only started dressing again after years of not dressing and started again last year after the feelings i had originally felt came back in similar circumstances and have now got my own female clothes hidden away and dress when i get the chance which isnt as often as i would like xxxx
hugs love and kisses Paige

[tryingtoblossom]

For me wearing panties,pantyhose and bras started around age 4-5 then by the time I was 13 I was ready for the next step and started wearing clothes (dresses and jeans with heels).

[Aspen K]

I remember I was about 10 and I was looking for something in the laundry and instead I came across a pair of cute green panties.....the rest is history ladies. Lol

[erica2054]

i am sure like everyone - around the age of 7 - saw moms bra and panties put it on . At that age - i really did not know what i was doing

[Sc0rp10N]

Not like "everyone"... I'm 39 and just started about a year ago...

[Velocity]

I must have been around 11 or 12. I remember the thrill of grabbing a bra and panties from my sister's room and running across the hall into the bathroom and locking the door to try them on.

[Jessica S]

I was 5 yrs. old. I was helping sort the dryed laundry and had for my moms kneehi's ask what are these and then just put them on. They felt great. It didn't take me long to look for them again and found some pantyhose. My mom kept a bag of old pantyhose in a closet right across from the bathroom I raided them all the time. The of course there were the silky slips and panites that hung to dry in the bathroom that I tried on next. Everything was big but I grew into her stuff between 10-13 yrs old. When I was 12-18 yrs old and left at home alone, I wore her clothes that I could fit into. After 18 I bought my own but was careful not to be caught.

[JulesAlton]

At 10 I started wearing my moms pantyhose

[Xandra]

Wow! That is really interesting that you started so late. No feelings before that?

Not like "everyone"... I'm 39 and just started about a year ago...

[AshleyT]

id when i was 8 id start trying on dresses that were in house

[Stephaniew]

started about 7yo... missing around with a older cousins clothes... and got caught... and my females cousins dressed me out in a little pink dress with all the fixings ...topped off with blush& lipstick...I pretended to hate it but... inside I was in heaven.

[susancheerleader]

I first wore my sisters one piece swimsuit (or maybe her gymnastics leotard) when I was 11 or 12 years old.
I always got caught. But I also kept taken them too.
Eventually I stopped. I was sick of being made ashamed.
It wasn't until I was 40 and living alone that I stated dressing again. Starting with a leotard, and going to pants, skirts, dresses......

[ajlove]

I was about 8 years when I started playing dressing up with my sister, in my teenage years I'd secretly wear her clothes. I've done it on and off all my life, but it wasn't until my 40's that I had the confidence to be the person I wanted to be.

[sharon7]

My first was age 12, wearing my sister bra that she left in the shower room, i cant forgot the amazing feel and keep repeat wearing bra for the next 15 years.. secretly for sure.. i never want to be a girl, just wanna have sexy boobs..

[jack.palmer1770]

Around 14 years old I secretly dressed in my mother's corsets and pantyhose and enjoyed the feminine feel I had walking around the house alone. Around a year later I purchased my own bra, couple pairs of panties, and fishnets to dress up whenever I pleased. I'm 23 now and haven't dressed much since 17 but will forever enjoy! Looking to buy a pair of heels and new lingerie in the coming weeks!

[Carmen de Rafael]

First time at 14, although I had thoughts of it long before that. At five, I would stare at the teacher's tan pantyhose covered legs. Couldn't take my eyes off them and wondered what they felt like. As I got older, I started looking more at pantyhose covered legs.

At 14 it all changed -- I "borrowed" a couple pairs of pantyhose from my neighbor. I put them on and was instantly hooked. Wore pantyhose only until 18, ah yes, the magical age of 18 when one's hormones boil. That's when my feelings changed, I wanted to wear more than pantyhose, I wanted to wear all women's clothes, especially lingerie and tight dresses. That is when I began to seriously shop for women's clothes, been hooked since.