Where did you first crossdress ?

[bettysmith]

I first cross dressed in my parents bathroom, my mum kept her girdles and slips in the airing cupboard. One day I slipped them on and I was in heaven !!

Betty

[Elle1946]

I would say my mother's bedroom while she was at work. Stockings and shoes were my first love.

[linnea]

I was in the basement where the washer and dryer were kept. One of my mother's girdles was hanging on a line that she used for drying some of her clothes. I was by myself and for whatever reason I decided to try on one of her Playtex girdles.
I took off my jeans, pulled on the girdle, and there I was! She came down the stairs at that moment and saw me. She said (in a fairly calm voice), "What are you doing."
I said, "Nothing."
She turned around and went upstairs without another word. She never mentioned it or talked to me about it, but from then on I experimented with her clothes as often as I could.
I was seven at the time.

[Angelofsomekind]

My best friend at the times bathroom. His mom left a bra in there.

[Veronica Electronica]

This almost sounds like a game of clue, "Colonel Mustard...in the library...with the lacy thong!".

Anyways, it was in the bathroom. There was a space next to the sink were we would put our laundry before it was collected and taken to the laundry room.

And my sisters bra was just sitting there by itself....

[Lorna]

It would have been my parents' bedroom on afternoons when I was home from school and neither of them would be back for a few hours. With obscure glass in the front door and hall window I felt safe to venture downstairs and the back of the house was not overlooked, so quite safe. Once there was a knock at the front door and I stayed quiet until I heard whoever it was go away. After that I would hang something over the letterbox just in case someone came to the door and looked through it to see if anyone was there!

[KarenSusan]

My grandmother's closet. She had all kinds of 40s and 50s dresses and lingerie.

[serinalynn]

Same for me, my mothers things in her bedoom. Oh What a Feeling. I was 11 at the time.

[trisha59]

My sisters closet. Which by the way would make a great name for a crossdressing store?

[Frédérique]

Where did you first crossdress ?


In my little bedroom – I had a nice full-length mirror there. However, I was lucky to have a barn to keep all my female clothes in, so I quickly moved everything out of sight, and nobody knew about my secret activity. I used to go to the barn a lot, unless it was extremely cold, in which case I would transfer my precious alternative lifestyle uniforms back to the little bedroom and carry on…

[Olivia]

In my bedroom, in Geelong, Victoria, Australia, where my family lived at the time. I was 13; it was my mom's big ol' bra. It still felt great and had an immediate physical reaction...ahem...:)
O

[AmyL]

In my early teens, back before pantyhose were invented, my Mother would leave her corset, garters and hose laying out from time to time. I'd slip into them whenever I sw them, thinking she'd never catch me. She never did catch me in them, but she did confronted me once because she apparently noticed that her hose were getting stretched out and were then too big for her to wear. I of course denied everything, but unfortunately she stopped leaving her things out after that.

[Kari Lynn Franks]

the bathroom sisters panties

[SweetCaroline]

The VERY first time. It was in the living room one Sunday morning right in front of my two little brothers. I tried on my sisters night gown when no adults were around. I was around six.

[Emme]

Come to think of it. The first time was in the sitting room off the kitchen. My mom used to let me play with her stockings and shoes. She said her dad used to wear grannies stockings to church. Ohhh those stockings still feel like heaven. I "found" a small bra in a vanity drawer, it had yellowed with age. Was a start to the bras.

Once I was playing in a large cardboard box and fashioned a bra from a strip of old towl. mom came out and said "whatare you doing? do you want me to get you a bra of your own." You know I said no! But wished she would. I know she knew I was messing in the dirty clothes hamper! She once complained of bra stretching. OOPs.

Once at our beach cottage mom was wearing a "tube top", I was about 10 -11 YO. I said I wish I had one of those. She smiled and said,"you don't have anything to hold it up!

GEE MOM, you would sure be surprised by todays adhesive silicone forms. Still don't have that tube top. LOL

I guess I'll have to go shopping.

Thanks for the forum ladies.

[Christina2008]

Like others the first time I wore feminine items was in the bathroom, the lock on the door was the safety net. The first time I put more than one item on was in my childhood bedroom, as I started to build my collection.

[sherri52]

My parents bedroom. We only had six rooms in the house if you count the bathroom/coal bin. At the time I started (Eight) I was already the oldest of five. Later it became nine. Ther were two rooms on each floor. My parents room was on the top floor away from the stairway. The only safe place to dress.

[SFRobin]

My first time putting on girls attire was in the bathroom of one of my friends. For some inexplicable reason, i open the hamper and saw a pair of his sister's panties. So irresistible urge came over me, and I simply had to try them on. Once I put them on, my fate was sealed.

[Karen43]

When I was 5 years old my parents were visiting friends who had a daughter the same age. Well she wanted to play dressup and I was dressed in one of her prettiest dresses. What a wonderful start.

[windycissy]

Mom's closet, then sister's bedroom, eventually the whole house when nobody was home...the risks I took!

[Christina89]

i first dressed in my room when i took a pair of my mothers bra and panties and tried them on in my room. since then it has been my room. i have walked around the house while underdressed.

[aggi123]

My first time was in the bathroom when my mother left some of her bras hanging in there. Had an urge and that was that.

[Ballerina]

Bathroom. After nabbing my cousin's brand new bra after she moved out.

[Meghan]

The family bathroom. That's where all of the drying pantyhose and the makeup were :)

Meghan

[CindyLouWho]

The first time, I was 5 years old and my mom made me wear a pair of her panties, under my boys clothes, to kindergarten. After that I put on my mom's panties quite often, usually in the bedroom I shared with my younger sis and bro. The first time I dressed fully was about 3 years later in my parents bedroom while they were at work. All my mom's things were in there and a big mirror to look at myself in. That's where I found out I'm a girl.

[pantyhosecd]

In my Mothers bedroom with a pair of her RHT stockings, been hooked from then on.

[Lara Smith]

So young I can't pinpoint. Maybe preschool.

[dreamer_2.0]

It was sometime in Jr High. I was going through the storage closet in my parents basement, ironically looking for old clothes I could use for a Hercules costume, and came across a box of some of my sisters old clothes. Inside I found a lycra leotard from when she was in gymnastics. The material felt smooth and stretchy. Completely new to me as I had only been used to boy things up until then. Curiosity got the best of me and so I tried it on. Wow...it was so tight and felt incredible how it stretched and covered me. I ran my hands over my stomach, chest, arms, butt, and felt myself getting hard despite being tucked away. I had never felt anything like that before and consequently led to my new hobby, which shortly after led to having the dream of being a real girl.

There may have been some earlier experiences with girl clothes before this, but this was the moment when I realized that a) girls have more fun than boys and b) I wanted to explore more.

Heh...feels good to share this. :)

[JENNYgirl]

For it was in attic sisters dress me in black tights plaid skirt and blouse :D

[babyrene]

I was 7...I think when i first slipped into my sisters yellow panties..then i wore her leotard and put her fur ear muffs between my legs...I was hooked...what can i say...

[TJ Tresa]

In my mother's bedroom, the bathroom, and all other rooms in the house at the time. My mother had dressed me up in some of her old clothes for Halloween. I was hooked, little did she know I had always wished that I was a girl at that time.

[Claire Cook]

I think I was 4 or 5. My mom let my play "dress-up" and put a dress on. me After that, I would try on her bras and girldes whenever I could in her bedroom.

[daphne g]

why the ear muffs between the legs?
not tried that b4
do tell, pleeese

[Leanne2]

I found a pretty dress in the basement that was a hand-me-down and still too big for my sister. I was four years old. I took the dress to the area under our front porch that was enclosed with lattice. I could sit under there wearing the dress and no one else in our large family could see me. Leanne

[DAWNB]

There was an attic in our house. I borrowed one of moms slips and tried it on up there. This went on for awhile and then I got caught. She didn't say much. Just told me told to change and left the attic.

[Jilmac]

For me, it was in an attic room. A cousin of mine had found a box full of girls clothes being stored in the attic and dared me to wear one of the dresses and a pair of panties. I was seven years old and the clothes were age appropriate so the dress and panties fit very well. I loved the soft silky feel of the panties and the prettiness of the dress. Having three older sisters I had an abundant supply of clothes to experiment with in their bedroom but that attic room will always be in my memory as the place where I started my favorite hobby.

[allisonrn06]

For me it was nylons, in the bathroom at about age 14. In a family of 7, the bathroom was about the only place I could get away with it, except for the rare occasion I could find an excuse to stay home alone. Never got the chance to fully dress till my early 20's when I got my own place.

[RiverdanceGirl]

My mums thick black tights on the floor of her bedroom . I don't remember choosing to put them on , I just had to . And then I put on my socks & pants , went downstairs and showed my mum that I had her tights on . She laughed , thought it was funny but let me keep them on the rest of the day and sleep in them . I was in heaven . She gave me a dressing up box with 60's style dresses , lots and lots of tights , bras , funky high heels , skirts and tops - the works . I would race home from school and dress before my dad got home - I wasn't to crossdress infront of him . On school holidays I could dress all day and did , even sneaking out in dress tights and heels to ride my bike on the back lawn . Funny , the neighbours never said anything even though they were not nice people at all . And then we moved house and mum said the dress up box had to go . So then I made a superhero costume with a black garbage bag as a cape and balaclava for a mask . Sheer suntan tights with red socks over for boots running around outside for everyone to see . Nothing was ever said . Well , except that Jane Whitley claimed I was the only boy in her ballet class - but I wasn't .

[Jenniferpl]

My sister left her bra in the bathroom, so I tried it on and never looked back.

[terry29]

my mom's bedroom,... I think it was a red matching bra and panty set. I've been hooked ever since :) Oh-yeah!

[GirlyGirl26]

My very first time was in my bathroom. I was getting ready to take a shower and my sister left her baithing suit there. I tryed it on and was hooked.

[woodstockloner]

my cousins bedroom while she and my aunt were at work... it was just a thong and a pair of pants but it was so freeing

[Krissie1962]

I was in the first grade.I had just moved into a foster home"one of many" any way I was playing with the girl who lived there about the same age as me I guess,she pretended plastic toy bowling pins stuffed in her shirt were boobies.and asked if Iwould like some ,I clearly recall her opening her dresser and handing me some yellow flowery panties and a girls nite gown,I changed in front of her and we both pretended the plastic bowling pins were ..well grown up girls is what we played in her room for a long time.I had tried on girls things before as well as sneaking off with moms things.I had enough brians as to know I should not be seen doing this.I never knew then that A boy wearing a girls clothes was socialy "awkward". I never stoped .the ones I liked nobody had.so in my early years no dought a few things became missing from ladies clothes lines in the middle of the nite.:o

[Paula TV]

When i was 18 home alone with alot of time to kill just putting on lipstick and make-up. It wasn't something i thought about before that, was just curious but i liked what i saw. It was a struggle for me as you could not imagine as it felt against my beliefs, as i had some very conservative beliefs at that time. But now i have learned to accept it. I hadn't really matured by then. I did as a kid put on heels to feel what it was like, but it was just a novelty and there was no real enjoyment of it at that time, so that doesn't count for me.

[Barbara Jo]

Like others the first time I wore feminine items was in the bathroom, the lock on the door was the safety net. The first time I put more than one item on was in my childhood bedroom, as I started to build my collection.

This is exactly as my "first times" were.

It was when I was about 9 years old when I first started to try on/wear my older sister's and mother's panties, bras and slips.

[JennaByNight]

I actually started "exploring things" when I was about three or four, but the first time I actually wore anything was when I was 16 and saw a black lace Teddy at JC Penny's. I bought it and wore it that night. And many nights thereafter. I remember that I felt absolutely electrified as I put it on. My heart pounded, my face flushed.... I also was NEVER late to get up in the mornings - because I always woke up really early so no one would catch me wearing it!

[AmiFL]

It was in mom's bedroom while they were out at work. She had alot of clothes that did not fit her anymore so she did not notice them moved about. My favorite outfits were a satin one piece swimsuit with a skirt and a pair of black skintight stirrup pants with a satin top. It was heaven. Then I began to dabble with makeup in our downstairs bathroom because for some reason I never felt dressed unless I was all made up and dressed..... it added to the thrill.

[StaceyJane]

I the bathroom. I would look through the clothes hamper for my mom's clothes to try on. Later I would try on my mom's dresses while my parents were away.

[StarrOfDelite]

and found out that i liked it. when i was about 7-8 my cousin (Female) and her girlfriend, who were 3+ years older than i, used to strip me down and dress me up in her panties and dresses and mary jane black patent leathers. i got such a raging pre- adolescent erection from that. wow! it still makes me aroused to remember that. they used to giggle so evilly.

i always lusted for my cousin, to no avail, but when she got married the girlfriend and i got drunk together, started talking about the old days. it developed that she got also got turned on when she was abusing me, and one thing led to another and we wound up in a motel room for most of that weekend.

[Tina Francis]

With twelve in my parents bedroom. I took some skirts and dresses from my mom and their shoes. Not high heels, but much higher than my children shoes and to big.

Later during my studies I bought my first own female cloth and they fit well, I felt like heaven since that date.

[ukcd87]

I first dressed in my girl friends bathroom, i was 5 years old and i wore her onepiece swimsuit.

[Jaclyn NM]

My mom's bedroom, where I tried on her stockings and high heels, and simply fell in love with wearing them. From there it just continued to progress to where I am today, a full out crossdresser.

[loardata]

i was in the 8th grade and i transfered to a local grade school, so i would get home before everyone else. so i would go up to my moms room a try on her brasw a panties-heaven:D

[ILV2DRESS]

i first dressed in my older sisters room I was probably 6 or 7

[Chris100]

When I was about 12 I found a way of picking the lock on the back door of our house. I hated school meals, so would sometimes go home to the empty house, pick the lock and get inside!

During one of these illicit visits, I had the urge to explore my Mum's underwear drawer and eventually started trying things on. I found it very erotic, but was very naive and didn't quite know why!

Became a bit of a habit after that :o

Chris

[erickka]

The closet in my room. It was full of mom's shoes, etc. that didn't fit in my parent's closet. Guess I was around 6 or so. It's been downhill ever since! LOL

[suchacutie]

which I did in my closet...the first time was for my wife in the privacy of a hotel room just before we left for home, so no "prying eyes" would see me. It truly was a life-changing experience.

tina

p.s. I was 55 at the time.

[JulieC]

Became a bit of a habit after that :o

I wonder why? I've been crossdressing for 30+ years and still haven't developed a habit. Hmm. :lol:

[MissyW]

It was the bathroom of my aunt's house . My cousin's panties. Oh what a feeling...

[ArleneRaquel]

[B] As a kid ( 8 - 9 ) I first dressed in my mothers clothes in my bedroom.[/B
:thinking:]

[Sophie Lynne]

My parent's room- my mom's bra. I think I was 7.

Many years later- my "restart" was 10/31/08... so I have an anniversary coming up. :D

[ArleneRaquel]

My parent's room- my mom's bra. I think I was 7.

Many years later- my "restart" was 10/31/08... so I have an anniversary coming up. :D

Congrats Sophie. :hugs:

[Samantha43]

In my bedroom when I was 13 or 14.

[Dayna3]

I would say it was in my dads bedroom with my stepmom's clothes, I must have been around 13 or so. I tried so much stuff on that day.

[sueb5678]

It would have been in my sister's room at about 8.
I put on her ballet tutu.
I haven't thought about this in years

[Tora]

Mom's bedroom, she had the best supply of Nylon delights. Panties, slips, nightgowns, hose. Wow, I was hooked.

[sherryR]

weekdays after school at friends house in his older sisters clothes in her bedroom

[Zoiq]

Was in my room at home... snuck a few items, tried them on after bedtime.

[Stephenie]

For me it was in my Mom's room while everyone has gone. Then found some storage boxes on the top shelf of my closet. Just added to them.

[Farrah]

My very first time was in my grandmother's room. I used to try on her slips. I simply loved the feel. However, to this day, I dont know what made me go in there and do that. I was about 4 or 5. Hmmmmm. Oh well, it all history now. After all those years, the pink fog still has a tight grip on me!!

[Kate Simmons]

Wow, that was a long time ago. My Mom"s room I think (when she wasn't home of course).:)

[Desiree2bababe]

Home, first time outside was on a pond fishing trip with my Dad. I'd swiped my sisters yellow lace slip and wore it under my clothes. I'd sneek off from my Dad and pull my pants down and look at it. Couldn't have been more that 6 or 8. Strange behaviour to say the least........

[Faye56]

My aunts house, staying there when I was 13 y/o and with 3 daughters I had a lot of choice.

[Jessica Who]

I guess I would have to say my parents' room :heehee: