How old were you when you started and who's clothes?

[Serena]

It was somewhere around 10, when I became trusted to stay home alone. I realized that I could do anything for the amount of time, so i explored my sister's room for fun. That was when I got the urge to try on my sister's clothes, just to know what it felt like. I started off slow with just a blouse on when they weren't home, and now I've improved alot. I'm pretty sure that was my first dressing experience, unless I got dressed up before the age of 4, since I can't remember anything before then. I just wish I would've been exposed to it earlier, because I love it so much.

What also may have influenced me to really try stuff on was that picture of Marilyn Monroe with the white dress. Anyone remember that? Well I wanted to know what it was like to have that feeling, but I wasn't sure when to get a chance to. Oddly, I forgot about the moment the first time I dressed, and I now remember I still haven't done it

Someday...

[Shining Star]

the first time i dressed was when i was 16 yo and a saw a pair of green sport briefs and a purple dress just lying on my sisters bed and i just had to put them on and after that i was hooked

[JennTV]

About 11 or 12 I think (nearly 50 years ago now). Tried mother's knickers and bra at first, and that gave me the first erection I can remember. I was trembling with the excitement. Then I found her hook-side girdle. It was really tight to put on, and the pressure on my penis inside it was really exciting. I found the rhythmic bouncing on the floor doing press-ups intensified the feeling until I had my first (accidental) orgasm. I have been hooked ever since, even though it took a long time to clear up the mess well enough for her not to notice.
Has anyone else got a more bizare "first orgasm" story?

Toni

I started in my mums tan tights aged 11, I put them on in front of her dressing table and got very excited - the feeling of the nylon over me was unbelievable as I wiggled my hips and watched myself in the mirror, so it was I had my first orgasm. As I wasn't sure what was happening, I pulled the front of the tights down and succeeded in spraying my mothers dressing table as well as the tights...

Needless to say I rapidly moved on to my mums panties, bra's, slips, skirts - anything and everything else I could get my hands on

Jenn

[ToniB]

Hi Jenn,
I know just how you must have felt. I remember it well, even though it was 50 years ago!
Welcome to the Forum too (first post). You'll find lots of support here, and advice, if you need it. Take your time and share some of your experiences with us. We're a friendly lot!

All the best,
Toni

[Faye73]

Hi there forum.

Let me first say that I have been a member here for some time now and I am only just posting my first post. So let me first say ‘hello’ to everyone here and I hope to speak to some friendly people here. I was quite shy to start with about saying anything here, but I have now finally though broken the ice within myself to do this.

I guess I first started when I was about 10 or 11 years old. Long skirts always fascinated me. Long pleated skirts and basically long flowing ones are the kind I’d like to wear.

I used to wear my Mother’s skirts as she had quite a few back when I was young. I can remember this long pleated purple skirt she had and a white one similar. I always got the urge when no one was in the house to put on a skirt. But that was not all, I got a real fondness for putting on a slip to or an underskirt as I call them. Long silky ones, white or black. And ever since then, whenever I get the chance, I’d put one on.

I tend sometimes to go the whole way and put on a blouse, skirt, slip, panties and bra. I feel so feminine and sexy whenever I do this.

I just like the sheer elegance of the old style of how women dress up nowadays. A long skirt and a blouse go a long way with me.

Thank you for taking the time to read my first post and hope to hear from anybody.

Bye for now and be safe.

Faye73

[robynlane]

It was my sister's 16th birthday. I was a two years younger and was about as lost as anyone could be. I knew nothing but that my body and mind were awash with desire (hormone ravaged that I was...). For the celebration, my family went to the Disneyland Hotel in Anaheim, CA, about an hour's drive from my home in theSan Fernando Valley. It was during a break in the festivities, of sorts, that I found myself alone in our hotel room... I was so rarely ever alone! But it was there within those few brief hours that I found what every fiber of my being had been longing for, found what I had not yet realized. There in the bathroom I found myself with my sister's clothes and my mother's makeup, somehow so drawn to it all, from some place deep inside I could hardly understand. I have not the words to explain from where my next actions led me, only that I can still remember with amazing clarity picking up my mother's Avon, Periwinkle Pink lipstick and pressing it to my lipsfor the first time (with so many years to follow!), my hands trembling in the obvious taboo of such an action, then putting on my sister's bathing suit and filling the breast with tons of toilet paper. There,suddenly, I was born anew. The virtually transparent Robby became glamourous Robyn and my world blinked from dark to light. It was there in front of that stupid Disneyland hotel bathroom mirror that everything fell together, there where I found me.

The next few months were simply a blur of finding private moments and of extra-long "baths" when I could extend my understanding of this new world I had somehow magically found. It was terrifying for me, every minute, but the desire far outweighed my fears. At every opportunity, my mother's and sister's closet and makeup become as if my own. I was on fire with it all, I have hardly the words!.

Finally, on an incredibly memorable Sunday when all were gone, I dressed for the first time completely - as complete as any boy-to-girl could ever hope for. With my long blonde hair, slight stature, and fairly good looks (no, really!), I transformed myself completely. Complete makeup (foundation, lipstick, mascra,blush...), pantyhose, my mom's black, 36D, full-bodybriefer stuffed full with old hosery she had forsaken (far better than the TP I'd been using!), and this AMAZING red-flower summer dress my older sister had worn to her prom. That day was as wonderful a day as I have ever had...

[JuliaMarie]

11-12...in my sisters clothing..

[horny_boy3107]

i was about 13. I had discovered masturbating not long before and for some reason i was rummaging through my mothers drawers. Most of her panties were white cotton but among them was a paid of black lacy panties. I had never thought about putting them on before but that day i did... i became very aroused very quickly leading me an amazing orgasm. For the next ten years i wore evry piece of lingerie my mother owned.. over time the stuff she bought became more exciting.. thongs, crotchless panties, stockings, baques, bras.. everytime i had the chance id be into her room and dressing up and jerking off. For me it is a purely sexual thing.

I also developed a fetish for shoes, especially open toe sandals, loved the way it feels to squeeze my foot into a pair that are too small. Thankfully i was never caught altoght they're were some close calls. I often wonder did my mother know as they're were times when i accidently dripped some c_m onto her panties or laddered her pantyhose.

if anyone had/has similar experiences and would like to get in touch feel free to email me - tipsy_tranny_boy@yahoo.com

[Sweet Susan]

It is amazing how many of us started at 11-13 years of age. It must be the erection thing.

[Jennifer1]

[Hi girls
I,m Jennifer and new love your site hope we can all be fiends .

[Amelie]

Hello Jennifer and welcome.

There are many fiends on this site, hope you find one to your liking. LOl
Amelie

[cdncd]

Mine started the summer i was 13. One of my friends parents kept borders and Larry was about 30 maybe and was always home when it rained. We would wrestle quite often and one thing led to another and well you now what happened after that. I was very slim and very white and he said that black panties would look great on me. He bought me a pair on sheer black and put them on me next time. It felt so wicked when he ran his hand over me that i could not stop squirming, and he laughed and said i looked so cute. He kept rubbing and i eventually made quite mess in my first panties. After he moved away i stopped for a while, but the urge kept returning. But i guess any one thats been there knows all about the "urge".

[Natasha Anne]

Before I relate my experiences, let me say this is simply an amazing thread. Reading all of your experiences has brought up a few of my own. I thought I recalled all aspects of my childhood and one or two came creeping out.

Anyhow, when I was 4 or 5 (can't remember my age other than it was definitely younger than 6 as I was not in school yet, but I do recall everything else!). I found a trunk in our garage which had my mother's winter/old clothes in it. I had a ball in the garage dressing up in all the clothes, and I can still recall vividly a green dress with organza, the texture and the way it felt. Obviously the clothes were way to big for me, but I haven't looked back since, and clothings texture still is a big factor when I'm out buying clothes.

[RhondaLynn]

I was probably around 13, back in the 70s. My older brother was a CD, and I would see him at night sometimes wearing slips etc around the house. I didn't quite understand. I found where he kept his clothes, and was looking through them one day, and found a pair of foam rubber breastforms. For some reason, I became quite aroused holding it, and i decided then to find out just how arousing this stuff could be. His things didn't fit me - I started scavanging clothes that people would give my parents, like before goodwill. I'd find a slip, a dress, a bra, etc. as time passed, and I'd get some hosiery from my mother or aunt. I really hadn't found my niche yet - i was just trying things out looking for that special something, but I managed to collect a box of things by the time I was a freshman in high school.

So of all things, what happened? Our school had kind of a hazing thing - each senior picked a few freshmen and did what they felt like with them one night, then the next day, we had to come to school and do anything they said. My senior decided that 'all of his freshmen were going to dress up like women'. He took several of us out that night, but I didn't go. But we were supposed to goto school dressed the next day - all of us did. I think i was the only one who had his own things that fit !!! My mother seemed surprised that morning - she mentioned off-hand 'I wonder how you found all these things that fit you so well...' Too bad I wasn't really into it as I became in later years - it would've been a day that dreams are made of if I had known my inner self that day.

Through the years, I learned to enjoy the softer side of life. But I still felt guilty afterwards, and purged several times during the 80's. NEVER PURGE - BAD !!! I lost some of my most treasured items in purges.

After a series of moves in the 90s, my things went into storage. I got them out a few years ago, and my collection has grown considerably since then. By now, most people who know me know what I do. I quit caring when I learned not to feel guilty about it, somewhere in the 90's. Since then, I've had a 'so what' attitude whether anyone finds out or not.

Ahh, if only I could go back to that day in my freshman year........... hmph.

[marissany]

I was four and it was my older sisters clothes. Wish I knew for certain I would feel this way all these years later I would certainly have acted sooner on my desires, no doubt everything would be a lot easier in my journey.

[RhondaLynn]

I wish I had had a sister. A role model, a clandestine clothing source, etc. What a difference it would have made. Everyone with sisters should feel privileged, regardless of the grief they may've put you through.

[benambcd]

I was 10 and was with my aunt, who is two years older than me. She wanted to use her dolls and for us to be doctors and nurses. (un)fortunately she only had nurses outfits, no doctor outfit, and so I became a nurse, the white outfit, the white tights, and I even had to wear her panties.

My Grandmother, my aunt's mother, caught us, and didn't say anything, but the next time I went, I had my own outfit and underwear to go with it.

Because I used to visit my gran regularly I could always be dressed up to play with my aunt. As time went on I went from the nurses outfit to ordinary girls clothes, even having my own schoolgirl uniform so that we could do our homework together.

We used to go out, to different places and my aunt would say that I was her cousin, we even got boyfriends!!!

I have dressed ever since.

Benamb

[sunita_rao]

I remember when i was first forcibly dressed- when i was about 4 years old and my brother and his friends put my sisters dress on me. i hated it at the time, but it lead to this. when i was 11, my mom and sister recalled when my brother dressed me and then i got to thinking. i wondered, what would it be like to dress as a girl? so i went upstairs to my mom's room and put on one of her bras and voila, i felt something inside of me that i never felt. i didnt put one on for the next two years until i was doing laundry one day and found my sister's college roommate's bra in our wash- she was staying over during fall break. that bra was beautiful- pink, padded, laced, and it smelled like her. and dammit- she was hot. so i put it on and found a small t-shirt and i had an instant rack. i then was sexually excited, in record amounts. i've been hooked since then.

[Jiera]

I really wish I had an exciting or exotic story, but the truth is, I was in college, and had fought my curiosity for a few years. One night I just decided I would do it to try it out (I had been thinking about more and more), so I went online, ordered an entire outfit, locked myself in my dorm room after everything arrived, and wore it the rest of the night. I told my roommates I was sick, and just walked around the room, read, did homework, and played on the computer.

It was a pair of chunky black schoolgrl pumps, white thigh-highs, a leopard print thong, a white blouse, a charcoal grey skirt, and a red wig. None of the items were on sale, and I think it cost me 200 bucks total. But it was worth it!

(I've become a more savvy shopper since then)



Ji

[gender_blender]

I was 4 years old when I started and I have the pictures to prove it. It was never a question, just something that was, and I have never "purged" of my female clothing.

I am an only child, so naturally my mother's clothing was the only clothing that I could experiment with until I began my own female wardrobe sometime later, around middle school.

~Charlie

[Aloha_Dana]

My early childhood is only faint memories, but two are clear as day. One is of my older sister running from bathroom to her room in nothing but her panties. She was all selfconscious about it, but I can still see them, white w/little red flowers. The second must have been shortly after. Our neighbors had children similar in age to our family w/a daughter my age. One day when they were out, I broke into their house through the window and did a full panty raid. I pulled out all the panties from the daughter, her older sister and her mother. Then I put on a pair and went home.

somehow, I got busted and I was still wearing the panties. I can still feel my embarassment.

Your Panty Theif,
Dana

[pamalamathews]

I was 5 years old when I wore my first Girls bathing suit and about that same age I was wearing mamas high heels. But I really lived for it when I turned 12. I started wearing my sisters drill team uniform and her bras & make-up. I also found a corset that was my moms that I just loved

[christy_blue1]

i was about 12 years old i guess. i was looking for something in the closet one morning, and noticed one of my sister's dresses. wondered what it felt like to wear a dress, so i tried it on. not looked back since.

it wasnt the first dress i wore that i have so many memories of. it was a dress someone from church sent her. my sister would get new clothes a lot, form other women at church who's daughters had either outgrown or no longer wanted the stuff she was given. anyways, the dress i have so many memories of was a light blue party dress, had long see through sleeves, and had a full pleated skirt. slip built in. zipped in back. i played sick one sunday so i could stay home and try it on.
when i put it on, i felt like the most beautiful princess in the world.

like i said earlier, my siter would get new dresses and skirt outfits a lot. i can honestly say , that i have worn almost every dress and skirt she did when we were growing up.

[ShannonP]

The earliest I can remember is at the age of seven when I was caught in my closet wearing my older sisters bra and panties.From there it progressed to my mothers,aunts,girlfriends and so on.Wish I would have followed my heart then.

[Alison9009]

I was 13 and I used to put on my mother's things when I was in the house on my own. I didn't have a sister to play with like some
I started because there must have been something inside me telling me to!
Anyway I did and still do enjoy it!

Hugs

Alison