How old were you when you first crossdressed?

I was always interested in wearing the pretty things that only the girls could wear as far back as I can really remember. Now acting on that... I did have a pair of my mom's heels I walked around in at a really young age more than a few times. I remember them vividly.

It was pre-school, and I started school around the age of 4 years 8 months, so before then.*  I must scribble out my early tale sometime.   School itself made me realise that the genders were separated by many artificial and needless rules  (Why can't I play in the Wendy House!   Why can't I be an angel in the nativity!  etc.)

* Hey, that means I'm around my 50th anniversary right now!   Yay!  Go me!

Hi Fiona. Even though it doesn’t have any scientific value, I dare to say that young boys who started trying on and / or wearing girls/women’s items of clothing were far less interested about the sexual aspects of crossdressing than those who got started during their early teens. (At least I know that is how it was for me). True, in my teens there was a close relationship between dressing up and sexual excitement, but when you are a teenager there is a close relationship of anything with sexual excitement!! 🙂

My oldest memory of me wanting to wear any item of girls clothing is from when I was somewhere around 3 or 4 years old. Then a bit later, when I was maybe 5 I ended up having to wear at least a couple items of girls clothes after a family picnic since I had fallen into a ditch and my own clothes were covered with mud. My mom didn’t pack any spare clothes and we were just minutes away from my aunt’s home so they took me there to take a bath. Now she only had 3 girls, the youngest just a bit older than me, so I had to borrow some of her clothes.

Anyway, posting this before I get over the limit of characters...

Gaby

i was about 11 or so. in school. had a school play had to wear green tights for the play. the play was snow white and the 7 drofs , i was scared at the time but when i put the tights on i was hooked, the feeling of them was out of this world, message feeling and when walking it was heaven. i became a x dresser slowly. it went away for years. then came back in my 30s. now in my 50s i have more female cloths then wife and more make up then she does. wife knows of my x dressing but will not let me sit with her and talk like 2 woman. she has seen me getting dressed up but would not help with make up or style my wig or any help. so here i am on the net for friends to talk to that under stand. i love to dress up and be pretty for that is what i should of been a female. when i dress up its like normal for me to dress in female cloths. even tho i am male.  woman dress  in male cloths all the time so what is wrong with men wearing female cloths?

I started actively dressing at fifteen. Our family  didn't have the funds to spare to buy my sister and I nice clothes to wear, that all changed when my father came into an inheritance from his  fathers estate. We moved from the city to the burbs and our lives changed, My sister got several nice outfits and went from drab cotton panties to pretty nylon underwear and nightgowns. We shared the same bathroom and laundry hamper, seeing those lovely panties and nighties got me wanting to try them on I could not resist myself any longer I was holding one of sis's nightgowns when I was caught by my sister. She did not get angry in fact she was very understanding and let me wear some panties and A silky nightgown to bed. I found out later my dad and my uncle both cross-dressed so I never had the feelings of guilt and shame so many of us have had to endure, never had to purge my stash, after reading the stories on CDH I realize what A lucky life I have.

My first time was around age 30.  Curious about wearing pantyhose was younger, but the timing and place that was presented was finally found around age 30.  It felt right, and closet dress when I am brave enough.

I was probly around 6 or 7 when I tried on my mother's panties. I was always more interested in girls clothes and girly things. Started fully crossdressing at around 11 or 12

I was 4. I would wake up in night and put on mums knickers and tights and go and sit for a wee

later became more serious around age 13 and I would dress fully and go outside when parents not around

had my first sexual encounter at 15. Parents away for night and I went out around 11pm for a walk in mini dress tights and heels. Got picked up by old guy in car who thought I was a girl. I told him I was on my period but offered him a bj

still remember the smell the feel the moans and the taste xxx

It first occurred to me aged 5 or 6 when I saw a girl in a skirted one piece swimsuit and wanted to wear it - I mean really wanted to wear it. I daydreamed about it for a long, long time!

I liked dressing up from my sisters dressing up box - always wearing dresses and my mothers old heels which were in there. My mother put a stop to that.

So my first proper experience came aged 11, during the hot summer of 1976.

My grandmother presented my sister with a waist slip. I had never seen one before, and thought it the prettiest, lightest, coolest thing to wear, and simply had to wear it before my sister did - the very thought of wearing it after her seemed horrible to my 11 year-old mind.

So I waited until I thought she was asleep, stole in, grabbed the slip, removed my pyjamas and put it on. Ahhh! The sensation was even better than I imagined.

But in the half-gloom came my sister's voice; "What are you wearing - is it my petticoat?

Hastily I slipped it off, put it back in the open drawer behind me, lied "No, nothing" and scampered back to bed.

That taught me to be a lot more careful, and to hide as well as possible.

Grrr! That we have to hide!

I still cannot think of a single reason we should hide except to appease others and thus confine our own lives to a second class status.

Oops - off topic!

Laura

Early teens - I guess 13 or so. Already fascinated by high heels, so when no one was around, would try on my mum's shoes and underwear. That's as far as I ever got actually dressing. Fantasizing, now .... 😉

I was about 8 or 9 years old when i first dressed up i used to wear my older sisters clothes when i was alone in the house, i didn't know at the time what it was all about i just thought i was just dressing up like when you put on a cowboy outfit or a uniform to play at cowboys and Indians or at being in the army, it wasn't until i was in my late teens early twenty's that i suddenly found out that i actually liked wearing women's clothing and would continue to wear them when ever i get the chance to, I'm always looking in the shops and magazines at the latest fashion's for women especially at the lingerie and what the latest dresses are in fashion, sometimes i wish i could take it a bit further and come out of the closet  we shall see what the new year brings, happy new year to everyone hope you all have a good one hugs Rozalyne x

For me it was a round age 10. I tried on a pair of my Sisters panties. And the rest as they say is history.

Amanda

i was 4...a neighbor girl aged 5 came over to play and she said lets hide on my mom so we hid behind this big chair...then she said lets switch under pants...so i took mine off and gave them to her and she gave me combed cotton with cherries panties...i put them on and felt so really good in them...so soft and comfortable...that started it all...i would check  out my my moms lingerie drawer and would put on some of her things...the feelings were beyond words...i loved the feel of nylon antron 3 etc....as i got older around 11 oe 12 i would ride my bike down to the 5 and 10 visit the lingerie department ...i would take pantaloons and panties and stuff them down my pants and walk out got home and immediately try them on...the pleasure was intense...i was so hooked....one time i slept over at a friends house and i would go through his sisters lingerie and closet..i tried on my first slip and slept in it....what an experience ....continued onto college and as an actor i would go into custume  room 20 to 30 years of clothing...especially womens gowns nighties sheer blouses etc i was in paradise...i would bring them back to my dorm room and live in them over the weekend while my roomate  was gone...for me as a adult i love the pleasure and sensuality of the female under things...im hetero i love women and what they wear and experience...however i would purge my lingerie from time to time....feeling quilty...ive been married twice my first wife never knew...my present second wife found me out and stopped sex completely and said i make her skin crawl...she found these underthings ....i told her im turned on by lingerie and the feel of it and use it for masturbation purposes...she didnt care and is a prude to say the least...very unforgiving , hateful, disrepectful...she is pretty much a tom boy and rarely ever wears sexy lingerie or a dress or stockings...plain cotton panties, plain white bra...pants always ...thick cotton pajamas etc...so for 15 years no touch, kisses or hugs...ive begged her to get counseling many many times...she says counselors are  phonies and scam artists...i dont know why ive loved lingerie so much...going into the store and seeing lingerie dept full of a sea of color and every fabric imaginable...the mens dept is one gondola of under pants...what choices women have and how lucky they are to have soft hair and even softer skin and then breasts so soft and nipples so hard...their curves so wonderful and their smiles melt me...beautiful and perfectly made...

Probably about 8 or 9. There was an old trunk in our garage and it had some dresses in it. I was fascinated by these and just had to put one on. I think my love of period costumes stems from about the same time when I read a book about all the finery that was female period clothing. I was hooked and these days own 3 examples, one American Civil War Ball gown and two 17th Century French, (with panniers to match).

I also remember trying on one of my mothers swimsuits with rather itchy tennis balls for breasts!!!

Some of you ladies have commented on how you were caught dressed. My folks had a weekend place by the sea and in my teens I refused to go there in the winter, cos there was "nothing to do".

So I was left alone for the weekend with the treasure trove of all my Mum's things. Some "rellies" came to check on me one night and I was well and truly "sprung".

My father , being the "product of his generation", ie the typical 60's Dad, told me that my disastrous  fate if I did not stop dressing, was that "the boys in the pub will call you a queen".

Quelle Horroeur!! (Cant spelt that, but you get my drift!!)

It brings  a smile now, but it was not funny at the time....

Two more "parentals".

My old man used to tease me about buying me a pair of pink panties.... I've often wondered if subconsciously, "it's all his fault".... (Lie down on the couch Caty and tell me all about it... But first,,, here's my bill!!!) But if he was still around, I might buy him a case of  beer and say "thanks Dad"!!!Dressed in my best Caty finery of course... He'd probably need the whole case to recover from it all!!!

I used to have a fascination with strapless bras. So at the tender age of about 12, I cut the straps off one of my Mum's.

I dont think she was all that impressed.!!...

Happy dressing

Caty