What attracted you to the first item you wore?

[heathr1]

For me, the feel and shiny look of mum's leather miniskirt.

[Katey888]

Oh gawd! That's so long ago now I'm really not sure I could answer with absolutely total recollection...

Knowing what it was (a fluffy, acrylic fur hat - quick! Urgent call out to the fashion police - crossdresser down.. :eek:) I'd have to say very simply, that what initially attracted me to it was the fact that only girls wore it. :) And after that, I suppose I must have been hooked by the feminine look and feel it gave me...

Interesting question - certainly has more depth if you go beyond the 'what', but it's Saturday night and a beer and Christmas choccies beckon... :)

Katey x

[Robin777]

For me, it was a pair of very sheer hip hugger panties With a embroidered pattern on them. I found them when I was getting the laundry out of the dryer for my mother.

[Belladdresser]

It was an ankle length skirt. I just looked up from my homework to see it hung up after being ironed and thought that I just needed to put it on. After that, something opened and j couldn't get enough. Swimsuits, denim cut offs, lingerie, blouses, whatever I could get my hands on. There was no turning back. I've gone a few years at a time keeping it at bay, but then it just always comes back stronger.

[prene]

I was attracted to the whole package.
I envied girls, their skirts, shoes, bra.
I know I was younger and wore a bras a lot.

[missjoann]

Since I was quite young when my mother started dressing me because she wanted a girl...I really can't say what it was that attracted me to dressing, it all just felt very natural

[EllieMayxxx]

It was a nice floral lace covered bra that had been left in the bottom of an old laundry basket and i had to put it on, something was just so enticing about it. As soon as I put it on i was hooked and it just felt amazing

[CarolBrown]

I wore a dress in a stage variety show, when I was about 12...

[pamela7]

i feel like two different epoch of replies.
in 2002 I chose and bought my first panties, and that was definitely for sexual play.
In probably 73 ot 74 I liked a couple of my mum's tops and she gave them to me, they were soft and comfy and I loved them. Somehow I then missed 30 years of clothing joy by trying to find replacements in mens departments - talk about dumb!

[Dana44]

It was nylons for me. Then in 94 I had an operation. I woke up with white frilly nylons on. Had to wear them the entire time in the hospital. I asked the doctor how long should wear them at home. He said for the next three weeks and after that any time you want to. LOL Yep even verified by a doctor.

[CDRMolly]

For me, the looks and feel of my sisters pantyhose,I was in my early teens.

[Ashley Lyn]

my sisters' petticoat..:battingeyelashes: Damned if my brother didn't catch me trying it on..:eek:

[chrissy111]

My sisters cheerleader outfit.

[Bruce64]

Every Male has a Feminine side, What attracts me to Feminine things?. That is something deep in me and was there before Adam was born, no one knows the answere for sure.

[Princess Chantal]

My youthful curiousity. I was a leg hugger when I was little and I was curious why my mother's legs felt so different when she had pantyhose on.

[heatherdress]

High heels - they looked and sounded sexy.

[Lily Catherine]

It was a long skirt and a qipao-styled blouse. I suppose the blouse hugging my body and the skirt against my legs were outright sensuous (although I doubt I could describe it that way at 11). Icing on the cake was how the skirt flared out when I twirled around. It made me feel pretty, at least below my head.

[Rachelakld]

Aged 4, sister had a tutu, figured if I could be 100% "girl" for a short time, then I would be able to ride her "girls" bike (boys didn't ride girls bikes in those days).

[laurenp245]

I remember it like it was yesterday, I was about 6 years old and I was in my older sisters room while she was gabbing away on the phone and noticed a pair of her dance shoes (ballet) under the bed. Unbeknownst to her, I strode right up and slipped my feet in them and stood there leaning on the bed while she gabbed away at her boyfriend. She never knew!

I'm still not sure exactly why I decided to put them on, but everything inside me was drawn to them like Gollum to the One Ring... Slipping those on was my awakening into this magical world.

<3 Lauren

[AllieBellema]

A poodle skirt costume. Was cheap compared to the one I have now, but I liked skirts with flair and that's what drew me to it.

[TrishaTX]

satin slip I think...and do I really have to explain:)

[Genni]

This is an insightful question -- or I think it would provide some insight to me if I knew exactly what led me to try on my mom's satin panties some 50ish years ago. My sense is that I was fascinated with the female gender and wanted to try something that was intended exclusively for them.

[Judith96a]

Curiosity- that which allegedly kills cats!
I wanted to know what it was like to wear a skirt. And there it was, lying on the spare room bed, a polka-dot mini skirt in my size!

[Sheila11]

curiosity and the feel of nylons.

[Ozark]

I first posted this in December 2007--- In March 2008 my mother passed away

My mother is now 79 years old and lives in a house my wife and I bought for her that is two doors down from us.

She is still a wonderful lady, getting older and just got her 25 year pin from AA. When I was growing up, I never knew she drank. I just thought that everyone occasionally found their mother passed out at the kitchen table with a half empty bottle of scotch. I'm much better now, thank you.

I was around 9 years old.

My 15 year old cousin had moved in with us. It was a sad story, her mother had died, her father remarried, the typical wicked step mother, car wreck, her father died and the step mother went into a nursing home. My grandmother said to send her to our house, we got so many kids another one won't make much of a difference. So she moved in with us.

Somehow in my 9 year old mind, I thought she (the cousin) was getting favorable treatment from my parents. I wanted to get the same kind of treatment.

For some reason that 9 year old mind also concluded that if I wore her clothes, my parents and grandparents would shower me with affection also.

I put on a pair of her yellow big panties (this was about 1958) and a pair of her side zip jeans and a sleevless white camp shirt. Nobody even noticed. (In retrospect I don't see how they could not have known, but they didn't say anything to me at the time.) I went upstairs and took the clothes off. Those panties did something to me.

One time when my parents went on a trip and the cousin was in charge of us. She was downstairs reading a book. I got on a pair of her panties and crawled into her bed. (In our house it was scandalous to sleep in anything but pajamas or a nightgown.)

The cousin came upstairs and turned on the light in her bedroom and saw me in her bed. I feigned being asleep. She came over and ever so gently lifted up the covers and saw me in her panties. The covers came back down, she turned out the light and went and got into my bed.

After a while, I went into my bedroom in just her panties. She was in my bed reading a book. I told her I was scared and wanted someone to hold me. She looked at me and told me to go back to bed and hold myself.

The episode was never mentioned again.

She eventually went away to college.

Fast forward about 5 or 6 years. I had developed a bedwetting problem. Wet beds and wet sheets were a real bummer.

My father insisted I was just to d*** lazy to get out of the bed to go to the bathroom. Lots of tears, spankings and wet pajamas. My mother eventually bought me several pairs of 'stay dry' incontinent pants that I was to wear under my pajamas. I was both embarassed and excited about them at the same time.

My father had remodeled our basement and turned it into a bedroom. I was down there by myself, had a tv and radio and my school desk where I did my homework.

I had progressed to buying my own panties by this time.---this was before walmart and kmart. Went to Kresgee's or Woolworths to get them.

One night I was in bed in a just a pair of panties.

My mother came downstairs to kiss me goodnight. My pajamas were lying on my desk, along with some laundry she had told me to put away earlier in the day.

She told me to get out of bed and put away the laundry like she had told me to do. I told her no, could I do it in the morning, I was tired.

Mother insisted I do as she told me to do. Then she saw my pajamas and wanted to know why I didn't have them on and did I have on my 'protection' (That was our code word for the incontinent pants and diapers I wore to bed....we would NEVER call them by their real names, only by protection.)

Mother than told me to get out of bed right now. I refused. She reached down to pull my covers off of me and I blurted out, "Mom, I'm naked!"

She went over to my desk and picked up my pajama bottoms, gave them to me and told me put them on and put away the laundry.

I put the bottoms on over my panties while still under the covers and got out of bed and started to put away my laundry. She then insisted I wear protection to bed and I was always to wear protection and pajamas to bed. Nice people didn't sleep without pajamas.

She then swatted my butt. She must have been able to tell I had something on under my pajamas because she pulled out the waistband and asked me what I was wearing.

I started crying. I told her it wasn't fair, I hated wearing protection, I hated having to wear big white briefs (JC Penny double seats--wish I had some now..she bought them for me) that looked like diapers, I hated wearing diapers to bed and I liked how these underpants felt. I told her I had bought them thinking they were boy's bikini underpants.

She hugged me and said she understood how I felt. But until I outgrew the bedwetting it was so much easier on her to have me wear protection. It was too much trouble to have to laundry everyday--we didn't have a dryer- and to wipe my face and put on my protection and go to bed.

And she stood there. I didn't know what I was supposed to do. I was too embarassed to pull of my pajama pants and have my mother see me in panties. I had only occasionally put on my protection in front of her, never in front of my father.

Finally I said the heck with it, sat on the bed and took of my pajama bottoms. I then walked over to my desk in my panties and turned my back, took off the panties and pulled on my protection.

This was very exciting to me and I didn't know why.

I started to get back into bed and my mother asked if I was forgetting something. I started to put on the pajama bottoms. No, my mother said, finish putting away the laundry.

I put away the laundry in my chest of drawers just wearing my protection. I was so embarassed and excited at the same time and didn't know why.

When I was done, my mother came over and kissed me and said, 'don't forget your pajamas." and went out the door and turned out the light.

Oh man, I knew I was in trouble. Not only was I a bedwetter, but my Mom had found out I wear panties. And she was probably going to tell my dad. I worried about that until I fell asleep. I think I cried myself to sleep that night. I wished I had on panties instead of protection.

The next day when I got home from school, I was in my basement room lying on my bed watching TV. My mom came downstairs with a bag from Sears.

She sat on my bed and said she loved me and was so proud of me for being a nice young man. She told me she was sorry that I struggled so much. She knew I was a good kid. Things will get better she said. Then, as she leaned over and hugged me, she said, "I understand boys need their privacy," and handed me the bag. "These are for you", she said.

Somehow I knew I had the upper hand. I just laid there and didn't return her hug or take the bag. She got up, left the bag on my bed, said supper will be ready when your father gets home and went upstairs. At the top of the stairs, she turned and said to me, "I am not going to mention this to your father."

After a while, I looked in the bag. There was a package of panties from Sear's. Three pair, blue, yellow and white.

[Stephanie47]

My family lived in a one bathroom apartment. My mother hung the laundry to dry in the hallway and in the sole bathroom. I brushed up against her nylon slips and thought I had never felt any fabric so soft. I started taking those nylon slips off the drying rack in the bathroom and trying them on. Next it was her long nylon nighties. One thing led to another and then it was her panties, hosiery, bras and girdles to go with the slips. Do I love nylon slips? Yep, I have over 400 full slips and about thirty half slips.

[Foxy Lady]

My mothers Playtex OBG and nylons way back in the mid fifties.

[RobynT]

early on, I grew up in a house of women..... Mom divorced, living with grandmother, my brother the only other male in the house (and we didn't get along). It was the 60's, and I got to see a lot of slips and bra's.... Mom and G'ma used to get ready with the bedroom and bathroom doors open (heck there just kids, they don't know anything).... boy did it peak my interest!!! Started with slips and panties, and the rest is history....I look back with fondness at those early days, before the internet, we thought we were alone, and then to find out that we aren't. and that there are so many of us we cant count.. proud to be who I am, love to do what I do, still love slips...:)

[Julia1984]

It must have been 1972 or thereabouts. I was 6 or 7 and home alone. I had to try on my mothers long Brown suede zip up high(ish) heel boots. Why? I don't now know, but I've had a thing for heels ever since.

Julia

[CherylFlint]

Bra and the garter belt.
Wig was last on the list.

[Lacey New]

The first item was panties. I hit puberty about the same time as the mini-skirt and a lot of the girls in school were wearing them - jeans were not allowed back then and neither were real short minis - I think they were supposed to come to the bottom of the kneecap but a lot of the girls tested the envelope. But anyway, the result was that if you dropped your pencil, and bent down to pick it up and looked at the desks behind you, you would often be rewarded with a nice view of nylon. Like most teenage boys, I was fascinated with what was under there. I also had a sister a year younger and she would leave her panties in the bathroom. You can imagine the rest of the story

[Angela Marie]

I remember trying on my mothers tights when I was 10 or 11. Loved the feel and the look. Eventually I moved on to dressing fully but even today my wardrobe consists of a lot of leggings and tights. As a daily exerciser I always wear tights when working out.

[CarlaWestin]

Playboy mags of older Brother > breasts fixation > mom's bra drawer > my bras > Carla

[CONSUELO]

An open bottomed corset and nylon slips. I found that the feel and look were very exciting. To this day I love the sheen of fine lingerie and the look of pretty lace trim.

[thomson737]

It started off with a pair of black polyester knickers from my sisters draws. I'm not 100% of the material to be honest but I loved them. They were like hot pants, or more like knicker shorts. She had several pairs... and I wish I still had them. She didn't wear them that often, since id check her draws each day near enough and see they were been buried. I used to take a pair, and wear them at night. Felt so great.

[adrienner99]

Lipstick and high heels. (See my post, 'The Crossdresser and Lipstick," in the writer's section.)

As a young boy, I adored watching women apply lipstick. It was not sexual, it was feminine, elegant, and lovely. It was something I wanted. High heels attracted my attention when my grade school teachers wore them and "clicked" their way down the halls...I read my mother's fashion magazines and catalogs, searching for pictures of both. At some point, I entered my mother's closet, put on a pair of black patent three inch heels, then sat at her vanity and put on her Revlon lipstick. My life would never be the same.

[Cassandra*]

As a young child I kind of remember putting on my moms panty hose but not for sure. So around 19 I was dating my first wife and we were going ice skating. She told me to try wearing tights to keep my legs worm. The rest is history.👡

[RachaelXD]

I have not told my Mum about my CDing.

Recently my Mum told the story of when I was young and had to go into hospital. In those days the nurse uniform seemed to include black stockings. No really - this is according to her, not some dream I had.
Apparently, I could not take my eyes of their legs and went on at length (as an unashamed - unselfconcious 5 yo might) "look at their legs Mum!"

Black stockings (or even better lace hold ups) are still my number one item.

[Krystenw]

I never remember not being dressed as a little girl.
My mother wanted a little girl and she got me.
I think the memories I loved most was the summer before I started the first grade.
I was living with the neighbor family for several weeks because my Mom was in the hospital.
She had a set of twin sisters several years older then we were.
They dressed us up as sisters and since the other girl had her ears pierced I insisted on having mine pierced.
I thought I was in heaven.
That and when they polished our nails.
To this day I love to have my nails polished.
It's amazing the things we remember, that was more then 60 years ago.
Krysten

[melissalynn]

For me, the feel and shiny look of mum's leather miniskirt.

I wish my mom owned a leather mini skirt.

[Ally 2112]

I just had these urges that would not go away .The first thing i tried on was a red dress that i actually never seen my mom wear .It had a blue bow tie and the 3rd time i tried it on the tie fell off .I tried to to put it back on as best i could after that the dress vanished

[Jessicae]

For me it was the silky feel of my moms nylons and panties. I was home alone a lot in my teenage years and had a lot of time to try her clothes on.

[threeheavenshigh]

Shiny + soft. :doll:

[Tara Rushing]

What attracted you to the first item you wore?

Now that's the $64,000 question!!!!!

[Lori Kurtz]

I wish my mom owned a leather mini skirt.

But guess what ... now YOU can own a leather mini skirt!

[cdterri]

4 or 5 yrs old, found a little blue cotton dress in a bag of clothes. I have no idea why but I put it on and have been wearing dresses and skirts ever since

[Matterhorn]

I was about five and my older sister asked me to come into her bedroom. She was taking ballet lessons at the time and brought out a box that she said was for me. I opened the box to find a pair of pink ballet tights and ballerina slippers. She said they were a gift for me. Given that I had two brothers, I felt pretty special that she had chosen me. While I never ended up taking ballet lessons, I treasured the tights and slippers. Sometime later I snuck into her bedroom and put on some of her red lipstick. Although I was busted when my mom and sister came home later that day and saw the lipstick all over my face, those experiences undoubtedly planted in me the seeds of desire to ultimately express my feminine side

[Nine]

The feeling to be "free" Under a dress or a skirt. I like also the feeling of earings.

[JessiFoxx]

It started with girls jeans and riding breeches. I just always admired how much better they look on them (gg), and just had to wear them myself. I was hooked and discovered my femme side.

[CallmeAlice]

That I got to feel all girly and wear a dress. As well that I can swish around the skirt (Please keep in mind I was like 12 at the time)

[mmandy31]

to me was my granmother's yellow silk panties that me hooked they felt so soft and i loved it when i put them on

[GeorgeA]

The biggest attraction for me were and are nylons, I have hundreds of pairs, maybe more. To hold up the nylons I need girdles & garter belts, and I have many of them. One of the most attractive lingerie items is the slip and I also have a good collection of them (nowhere near what Stephanie's collection is). Dozens of panties complete the set. I must state that my lingerie preference is white, I have only one black and one yellow slip. I have absolutely no affinity for bras, jewellery, make-up, shoes or wigs. I underdress all the time, with only minor exceptions. I no longer consider that I am crossdressing, these are my regular clothes, and I'm most comfortable in them.

[Rosemary+]

I was young pre school age,
I was watching my mum get dressed for a night out with dad, she was sitting at her vanity applying her make up and thinking I'd like to try that, I don't why but It resonated with me

[Adriana Moretti]

great question.......for me it was the material of the item....it was my cousins dance recital costume i found when I was really young ...it was made of this silky material that was new to me, and it had a sequin collar....and we all know how CD's LOVE sequins right !!!

[Patty's panties]

I started out slow. First a pair or panties then another. At first it was a sexual thing, but after a while I found myself looking at skirts and dresses on Amazon. Soon I had a shopping cart full of choices. I finally bought a red skirt and a cute crop top to go with it. I was so excited waiting for it to arrive. As soon as it got here I had to try it on. I felt so...pretty. After that I had to buy shoes. So many shoes. I now have a dresser drawer full of bras and panties and a closet full of dresses and skirts and tops oh my.
I have a shopping cart full of stuff just waiting for me at Amazon.


Peace....

[BLUE ORCHID]

Hi Heathr:hugs:, That was probably 69yrs. ago, Probably moms nylons or slip,
I don't remember what I had for Dinner last Evening. ~~...:daydreaming:...

[Lacy PJs]

I was attracted to the feel of nylons...

Lacy PJs

[Scarlett Viktoria]

I think, like others, it was the feeling of the material while wearing it. I still can't stop feeling certain materials while wearing them lol.

[Sister Rachel]

I was too young ( about three ) to think about WHY I put on my Gran's panties, I suppose the silky fabric and lace trim seemed exciting. I just remember that I REALLY, REALLY liked it!

[threeheavenshigh]

I think, like others, it was the feeling of the material while wearing it. I still can't stop feeling certain materials while wearing them lol.

So true! I just don't get tired of the fabrics! So sensual... Mmmm....

[Kelly63]

Had to be pantyhose. So soft and silky

[wanda66]

My Mom's panties and slips,so smooth

[Dee-anna]

i went to visit cousins in another state when i was 7yo for a few weeks . my cousin showed me her new swimsuit a shiny one piece i told her i really liked it she told me to try it on so i did then she showed me 2 more one piece swimsuits +a two piece bikini and a pink leotard for her dance class i got to play dress ups for two weeks with her .now days swimwear is my favorite .:o

[kittie60]

It was the soft cool feeling I got from a nylon slip. That was a sensation I never forgot

[Bruce64]

The soft silky fabric, it still does.

[Judy-Somthing]

My older sister talked my two brothers and I to dress up in their ballerina outfits when I was eight.

For you older guy/Girls that started in the 60's clothes you remember fabrics were much stiffer with no stretch or give so the feel was much different from todays clothes.

I was before puberty but I remember the snug of the tights and ballerina outfit to be very pleasurable, BIG TIME! -Yes LOL-

[Gina Torres]

First thing I ever done did was attempt to paint my nails when I was like 4 or 5. I got a smack and a "NO that's for girls!"

I don't know what it is about nail polish but I love love love looking at my hands with the nails painted. My mom prolly traumatized me into liking it, haha.

[Jenny22]

My elder sister's pretty, ruffled very pink panties. I just had to try them on (age 6 or 7) when I found them in the hamper.

[Melissa B]

It probably was my mother's satin panties and Playtex 18 hour bra. From there it advanced to her sheer nightie. I remember looking at the Sears and JC Penny catalogs and the women's undergarment sections. Knowing that those were item I wanted to wear but never could own when I was young teen still living at home.

[LisaNJCD]

I remember it like it was yesterday....my sisters pink bikini hanging in the bathroom shower. Something inside me just said I wonder how it would feel to wear that. I was 8 years old.

[sometimes_miss]

Hard to say; the first female items weren't my choice, that decision was made for me by others. My own first choice was one of my sister's old dresses when I was about 11. It was red with a peter pan collar; I think the fact that it zipped up the back had something 'feminine' about it, and zipping it up DID make me feel quite distinctly as if I was a girl. The first thing I purchased was a camisole and tap pants set, which matched something my sister had, but she kept it in a particular place in her drawer, and I didn't dare borrow it or she'd definitely know.

[heathr1]

sometimes_miss. If you are willing to share, what was your first item not through choice?

[AshleyJames]

Thongs. Something about them intrigued me. After "borrowing" my first one I was hooked, I loved the way it felt and couldn't understand why it was only socially acceptable for men to wear them. Shortly after I became even more curious and fell in love with bras, nylons, garters and heels. I know my mom probably noticed me wearing them on several occasions, and my sister definitely knew all along as she uncovered my collections several times when she decided to clean my room from time to time when we were growing up.

[Kiersten]

It was one of my mothers night gowns. Not really sure why, other then the fact it was very soft and frilly

[Bruce64]

The Fabric, soft and silky.

[threeheavenshigh]

It probably was my mother's satin panties and Playtex 18 hour bra. From there it advanced to her sheer nightie. I remember looking at the Sears and JC Penny catalogs and the women's undergarment sections. Knowing that those were item I wanted to wear but never could own when I was young teen still living at home.

I definitely tuned into the underwear ads more than any nudes. I remember finding a Playboy under my mom's bed (she supposedly bought it to investigate the Jessica Hahn pix), started beating off to the some chick hanging out of a Nascar suit but tossed it aside in favor of Cosmopolitan's shiny garb.

[Wen4cd]

It was lacy, white, and satiny. It looked like pretty doll's clothes. I wanted to be like a pretty doll.

Full story here:
http://www.crossdressers.com/forums/showthread.php?187692-When-did-you-first-crossdress&p=3856089&viewfull=1#post3856089

[Alice-n-wonderland]

The site of nylon clad legs, just had to know what it felt like to wear them. I shouldn't have done that.

[Anita Cosmolover]

Definitely inspired by COSMOPOLITAN! Seeing those beautiful models wearing lingerie did it for me!

[MidwayNH]

what attracted me was Corsets. One day I saw one and was like "I wounder what it is like to wear one of those" that is what got me started looking through my mothers stuff. Sadly not 1 corset could be found. But my older brother found me looking through her stuff and figured out what I was doing. He gave me the first thing I ever put on. A pair of pantyhose. My brother has a pantyhose/spandex fetish.

Depending on your point of view it had been ether down hill or up hill from their.

[Milly1410]

It was my mom's bra and slip, then i moved on my sis' closet, until i bought my own stuff

[wanda66]

No sisters , Mom's panties and bra got double use,then her dresses

[Genifer Teal]

High heels. I couldn't imagine how anyone could walk in them. I had a very short 6th grade music teacher who wore 6 inch heels all the time and walked effortlessly in them. I was a fascinated. I had to see for myself what it was like to walk on tippy toes.

[Devone]

It was an ankle length skirt. I just looked up from my homework to see it hung up after being ironed and thought that I just needed to put it on. After that, something opened and j couldn't get enough. Swimsuits, denim cut offs, lingerie, blouses, whatever I could get my hands on. There was no turning back. I've gone a few years at a time keeping it at bay, but then it just always comes back stronger.
When I was young kid , my mom and her sister were these cute petite Southern Italian women who were well developed and wore sexy swimsuits and clothes around the pool area of our house. One day I found my mother's bra hanging in the changing room of our house , tried it on, got a stiffy and that was it for me. To this day I enjoy the sun working on my tan and wearing string tops with a push-up bra and panties, still gets my juices flowing.Devone

[Eva Bella]

The site of nylon clad legs, just had to know what it felt like to wear them. I shouldn't have done that.

Agreed. I remember going out to JC Penny at the age or 8 or 9 to buy myself a pair of stockings and try them on. I've always been fascinated by nylons.

[Rita Leigh]

For me, I remember being dressed in a women's long satin nightgown or slip when I was 3 or 4 years old. Either my mother or grandmother helped me do so. To this day, I love the feelings of silky garments. Bras, panties and girdles came later, especially when I was sexually abused for 2 years by a male babysitter who made me wear these items for him as he masturbated me. My love of women's clothing though was fixed at a very young age.

[MissVirginia-Mae]

My grandmother's girdles and full slips....
Opened her drawers once and I was hooked!
Prancing around in her nice open bottom girdles, trying to attach the stockings and putting on her full slips...
I was in heaven.....I knew I should have been a girl right there!

[Ressie]

IIRC I wasn't attracted to my sister's coat when I was 5 or 6, but my mother had me wear it to go trick or treating. Within a couple of years I was attracted to wearing silky panties that came with a large doll of my sister's. I was right, they did feel good to wear until my mom found me wearing them and took them away. Seems like I wore them for a couple of weeks, but maybe it was only a couple of days ;)

[Claire_tv_uk]

My story is similar to others talking about adverts having an effect,

When i was young the wonderbra adverts were huge in england, all over billboards wherever you went, i developed an almost obsession to them which i thought was just because i found the models attractive,

Then one christmas my sister got a black lace wonderbra for christmas, i realised my near obsession was with the clothes and not the models, i then put the bra on the next chance i got and loved it as well as realising i loved trying on all her other clothes as well.

[Barbara Jo]

As young boy growing up the 1950s, I was obsessed about how it must feel to be encased by and confined by all the feminine lingerie and other female clothes that my mother and older sister wore.

So, finally, one day I decided to find out.
I first put on my sister's nylon panties, bra and a full. slip. I was instantly hooked

It was then that I realized that I loved to feel / be feminine and I would never be like other boys.

[Lori Kurtz]

I was instantly hooked.

For a lot of us, putting on a bra was what got us hooked.

[heathr1]

Thank you for all your replies.

What is for sure is once you have decided to try something, there is no stopping/going back.

[Suzy Parker]

As a young boy of 6 years old I was always fascinated with the womens underwear section and also the clothing section in the Sears, Wards, and Meir & Franks catalog. I did not just look at the pictures I read all of the descriptions as well. One day after showering I noticed one of my mothers Corselette's in the laundry and I just had to try it on. I didn't know why but it felt so natural. It was then that I was catapulted into this life of heaven and hell.

[Roxy]

I don't know what attracted me to the first thing I wore but when I felt satin and lace on my bare skin, when I was very young, I was hooked. My mothers drawers were off limits for me, but some how found discarded under garments that I tried on and even made my own panties from scraps when I was 10 or 12. This lasted until I was in my thirties and started buying stuff mail order.

[Lynette]

For me it was seeing my sister in her girdles and slips One day I tried them on and was hooked.

[susan2010]

Me too! Just had to try my sister's petticoat! I was 4 or 5.

[suchacutie]

LOL...haven't thought about that first time in a while. We were just perusing through my wife's lingerie drawer when she came across an item that didn't fit her anymore. I had just lost a bunch of weight and I joked it would now fit me. She looked at me and said, "here...try it on". A few weeks later Tina was born!

[Alice_2014_B]

I cannot exactly pin-point it on what it was about high heels.
It was just something about how they felt and looked.
Part of it may have been knowing that, as a boy, I was not supposed to infatuated with them, at least not in that way.
:)

[stephiemont]

My mom was a corsettiere for a company in London's West End called Rousell, she made lacy basques, bras and so on and one day she must have made one that was too small for the order for it stayed in her locker for quite a while. One day I tried it on and that was it. I was 13 then and 68 now and with my wife's acceptance am en femme for most of the time. She even buys my make up. I'd love one of moms corsets though! And yes I think she knew.


Steph

[suit]

well i wanted to know what the girls that looked like the ones on this sight must feel when in clothes like there shows wearing.
http://downinflworld.tumblr.com/archive

[Angie G]

I think it was just that it was for a girl and I needed to put it on.:hugs:
Angie

[heathr1]

Yes, there is that to it also.

[renaej7]

...I remember it like it was yesterday. It was a pair of bikini leopard panties. They just caught my eye and for some reason I reeeeeeaaaaaaaaaalllly wanted to put them on. After torturing myself not too, I did. One of my best decisions. :)

[NewBrendaLee]

I have always wanted breasts so for me it was a bra

[Daryl]

The smoothness and silkiness of panties.

[PattiMichaels]

It was a form fitting knit skirt and sweater set, just my size thanks to Mom's genetics. The first time I went out in public as Patti was in 1986 at the ripe old age of 17, I only had to buy a pair of shoes since My feet were about a 1/2 size too big to wear hers. Except for the shoes, everything else was hers...the rest is history!

[lauriejean]

I still remember the what, but not the why: A suitcase in my aunt's attic with a couple of old swimming suits and bathing caps. I'm still not sure what made me think it would be fun, but enjoyed trying to "transform."

[JaniceP]

The pretty, soft look and feeling. It made me want to feel and look like a girl.

[Candey]

Going to the rummage sale and wanting to try on the dresses and heels.

[Bobbie1952]

Seeing my cousin in her slip. A simple full slip with just a hint of lace and a bow. I just knew I wanted to wear it.

[cdlove]

The first time I tried on something silky, something smooth, and so comfortable it was like wearing a cloud I was about 4 years old. I will forever remember that night because it was a start of a life long struggle between accepting it, realizing how it’s part of me, shame from those that don’t understand, and overall confusion as to why I was such an outcast. My father was on the couch in the living room where I was forced to be so he could keep an eye on me. It was dark and I was throwing a fit because I wanted to play my Nintendo (which I had just gotten after it had been released a year earlier). My father a very stern man told me to sit in the chair in the living room and shut up, “watch the movie you little brat” were his words. So I sat and I watched, not knowing what movie it was the next thing I know there was a woman in her lingerie and then nothing. I can remember wanting to know what it felt like to look like her and had many questions of what was exactly going on. Remember I was 4 so this world of women was very foreign to me. Later that night when my mother returned home from her shift at the hospital her and my father were in their room, having sex when I walked in unannounced. They didn’t notice me and I had not a clue what was going on all I saw was my mother in something that looked like the woman in the movie, that my father had made me watch a couple of hours earlier. Still curious I snuck out of my room once again and into the laundry room where there lay a pile of my mother’s cloths. I grabbed her silky panties and back to my room I went. I remember them being way to big for my little frame so I wore them under my own underwear that night. The fabric was so soft and something I had never experienced before. That one experience has turned into a live long love for the female physique, and clothing that I continue to enjoy. It has also been the catalyst of a life long struggle to accept that its ok to enjoy, its ok to crossdress, its ok that it’s a part of me, and a confusion of why its judged so much in today’s society.

[krissy]

For me it was my sisters clothes .that i was forced to wear and sit on our porch all day by my stepdad.

[Queen Erika]

The color and tightness -- black pantyhose...

[Cristy2]

Good question! I honestly don't really know.

[trisha kobichenko]

My mother's silky blouse, left on top of the clothes hamper. I felt how smooth it was and loved it. I put it on and felt it caress my skin, and have been hooked on that feeling ever since. There is nothing in male clothing that can compare to that feeling.

[Patrica Gil]

Seeing a young lady wearing a pink skirt suit with matching pink pumps. She looked great and it took me a while to see why her legs looked so nice. She was wearing nylons and that was the first time I knew such things were around. By the time I was thirteen I was wearing a pantygirdle with thigh high nylons. They felt great, but as expected it wasn't enough. The first time I went out as a girl I was fifteen, and it has been fun. Throughout the years I changed to wearing pantyhose, but recently my love expressed she prefers me in thigh highs. So back to the pantygirdle now. later. g

[cindi cinnamon]

PANTIES!!!
My wife has always told me I have a cute butt...and, the first time I modeled for her in a pair of g-string bikini panties, we were both hooked !
That was 30 years ago, and still struggling to decide which panties to wear every day.

[SaraCro]

High heels.I remember when i got my first job buying them,i was about 18..41 EUR size they fitted me well..i used to hide them under my bed at home then put them on when i was alone,paint my toenails and put some sheer nylons,and i felt such a turn on and adrenaline rush..then after some time I just drop them to garbage because..i dont know I felt something like shame..that was my first moments with crossdress :)

[ZenladyCD5]

Pantyhose/tights. I tried on my mother's black leotard and tights long, long ago and ever since then, I've been hooked and wanted to try more. I love lycra/spandex. It just makes the body/legs more slimmer, sleeker, shinier, sensuous, sexy, smoother, seductive, shapely. Did I miss any other S words? LOL! :D

[colector381]

I think with me it was my sisters champagne and lace dress (and her shoes)

[heathr1]

Also, on deciding to try something on, there was no going back!

[Paige300]

silk and satin and leather pants i just love the feel

[Fiona123]

The first item I tried was my sister's 1 piece swimsuit. Curiosity attracted me. I can still recall the thrill of feeling and seeing that my boy parts were gone.