When did you first crossdress?

[LenGray]

Can't remember exactly when, but I know that when I was little I was in LOVE with my brother's cargo pants and band shirts. My mom was always trying to get me to wear cute dresses and skirts but I was constantly going into my brothers closet and getting his clothes instead lol I didn't realize that was cross dressing back then though, I just knew that I was so much more comfortable in them :) This continued pretty much until he moved out to live with his girlfriend.

I was about 15-16 when I dressed with the intention of being perceived as a boy. I hated my sex a lot back then and I'd just moved to a new town so I figured, why not? I liked the feeling that I got from it :) I felt very sure of myself, much more so than when I dressed as a girl. Since then, I've kind of been waffling between the two lol

[Laura]

Well for me it started when I was about 11.

My friend told me that he used to put on his mums shoes and dance to Human League records. I tried that with my sisters shoes, loved it, and decided to take it one step further. She had a beautiful powder blue bra with matching knickers and suspender belt. How could I resist? And when I saw that she had white stockings in her drawer too, well that was enough for me. Although she didn't have a name at that stage, Laura was born.

She has been a secret ever since but I'm hoping to get some tips and advice from the girls here and see if I feel like.........................who knows what!

Time will tell.

[JazT95]

I must have been around 6 or 7 when I started having a strange interest in wearing tights. It took off after that before I started dressing seriously when I was 14 :)

[MaryBeth29]

One of my earliest memories, not just in crossdressing but really in life, was being in pre-kindergarten and putting on this ballerina tutu I found in the toy box. Who would've thought that little, innocent action would have led to all of this.

[Xandra]

Minj skirts from cut-off jeans. Love it.
Hmmm, not sure if mine counts....but my mom was the
oldest of 4 sisters. One was still pretty young. They
weren't a well-off family, so when i was brand new, for
my first few years, my clothes were hand-me-downs
from the sisters.



My mom told me that years later. I do vaguely recall
sitting under the ironing board in the half-assed shack
we lived in and one of the sisters teasing me about the
little dress i was wearing. Playfully, of course.

On my own was about 8. I didn't know or care about
anything to do with sex....i just liked the clothes.

I made several mini-skirts from just cut-off jeans for
years after. I could make them whenever i wanted
a new one.

~♥~

[Aeslyn]

Was thinking about this topic just recently trying to remember. Unfortunately I don't. But I do remember that is was such a secret part of my life, my secret pleasure, by the time I was 8. Somewhere around that age there was this one day my cousin who was my age suggested we steal some panties from a clothes line and wear them all day everywhere we went (it was a small town and kids of that age had a lot of freedom). This is the first specific memory of wear anything girly. How I know I was already into wearing that stuff though is that I distinctly remember how excited I was by his idea and how much I felt that I had to hide my excitement lest he learn my dirty little secret.

[dressyjessy]

I started much later. It wasnt untill i was 21 when my girlfriend would leave some cloths at my house, well my parents house. I started wearing her panties. Not too much later i bought my first pair of heels from Payless. Oh, ill never forget how it felt the first time i put them on.

[Xandra]

Aeslyn: I love your story.

[trisha kobichenko]

I think I was 8 or 9. My mother had left some of her clothes lying around and had gone to work. I was home with my sisters, and went into the bathroom and tried on a blouse (nylon or silk) but very smooth and sensuous. I loved how it felt and looked! Then my little sister burst into the bathroom. Some fast talking satisfied her curiosity, and I was glad because I knew even then I needed to keep it secret. But i was hooked, and have been dressing ever since. In secret for many years, but came out to my wife about a year ago...

[Aeslyn]

Aeslyn: I love your story.

Thankies :)

[Nadina]

Panty hose age 11? 12? then panties and a skirt that was my aunts around the same time, There is something about wearing panties and a wispy skirt for me, the way the air feels around my legs when the skirt moves around brushing against me, I feel like a different person with a skirt on.

[longirl]

I was 5 and my Cousins were living at our house and i have a cousin that is a few weeks younger then me and i took all of her panties, that is also the first time i got caught because she had no panties and they found me wearing them.

[kiwidownunder]

Around 6 years old ,at a friends party his sister was a lot older and got us to dress in her old cloths
Felt wonderful!


kiwi

[Barbie Anne]

I was 5 and my Cousins were living at our house and i have a cousin that is a few weeks younger then me and i took all of her panties, that is also the first time i got caught because she had no panties and they found me wearing them.

I already posted the story in this thread but the short version is DITTO lol. Glad I wasn't the only one :)

[AprilSavanh]

Probably around 12-13 years old, still to this day always been just me...long time closet cd.

[Lexi Moralas]

I was 11

[Ozark]

Way back December 2007, I posted this on the board. Seems that it fits in here. My mother has since passed away.


I posted this before, but it seems appropriate for this thread.

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, 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.

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 I thought 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. 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.)

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."

[Felicia Dee]

Hi Alexandra! Thanks! Now if I could just find some local grrls to hang out with... ;)

[Olive_CD]

Around 13 I had one afternoon by myself every week and my mom used to store her used pantyhose in a plastic bag. I started wearing wool tights I used to wear during ski trips, and then the pantyhose in the bag and became hooked to pantyhose. I bought my first pair 10 years later.

It took 20 more years after the first episodes for me to turn to other aspects of crossdressing, involving stockings and garter belts, skirts and dresses, knickers and bras, and now ballet flats and heels.

[FemPossible]

I remember I was like 10 or 11 and my sisters dressed me up as a girl. It wasn't very detailed (like panties or bras), just a wig, a little makeup, tight sweatpants and a blouse. While it may have just been a bunch of goofing around, I felt really comfortable in those clothes.

[Wanttodress]

I'm hoping to start in the next week or so. Finally worked up the courage to buy clothes.

[Gina04]

My grandmothers pantyhose and my moms heels. I still look for that wonderful round toe looking pumps. But I feel so ashamed when I go to a store thats crowded and look around at the heels. Anyone else feel that way??

[GenieGirl]

When I was around 5. I first got caught when I was about 9 by my mom. She didn't like it. Afterwards years of off and on cding trying to repress it from then on up until about 3 years ago when oi said to heck with it!

[Jenny Elwood]

I was between 4 and 5 y.o. My brother and I wanted to dress up in my parents clothes. We "fought" about who would get to wear my fathers clothes. He is older than me so he reckoned he should have first choice. I "reluctantly" relented. I never let on that I was glad to be the younger.

I think my mom still has this out of focus picture of two little scarecrows out on the lawn, one is wearing a slip.

[Truth]

First time I CD was when I was about 13 or 14, whilst my step mum was out!

[Krisi]

Probably around age 12. Stuffed my mother's bra that was in the dirty clothes basket.

[Sarah Smith]

For me i reckon it was early teens raiding the washing basket! :)

[Lucy Lou]

For me it was when I was about 16. Just one dress in the bathroom. it wasn't until I left home and got my own place that I really started putting on more things and it has just got more and more as the years have gone by. The first time I actually did the whole thing with full make up, shaved body, wig, painted nails, jewelry, stockings, basque, panties, high heels and not forgetting perfume was about 5 years ago.

Lucy Lou xx

Nadina, totally agree with that. Panties and stocking and suspenders and a short skirt. Wonderful. Lucy Lou.

[Sallee]

I was real young in 3rd grade I thought about it but really didn't get into it until early teen years and when the 20's hit I went all out wig falsies out to the clubs had a great time but now it is when I get time which isn't often enough.

[kev.wong140]

Beginning of this year! Fell in love with my gf's skirts ... Then I bought some pantyhose and a pair of heels ... fell in love with pantyhose and heels even more ... then, soon the whole package came along.

[ClaraKent]

I've only recently started explore this side of myself because of numerous reasons, but I can remember trying on girls clothing when I was at least four or five. It got severely repressed by my family so I'm letting her out finally.

[Jennifer S]

Second or third grade. I spent A LOT of time in my mom's closet!

[bittersweet]

First time I fully dressed up was a year ago when me and my bestie went shopping for clothes and oh did it feel so liberating!

[Leslie Iz]

I used to "borrow" control top pantyhose from my mom and then wear my sisters bras and panties. 1979-1984. 11-16. I was kind of a devious child and teen always curious but something definitely stuck when I first started cding. The emotions and feelings I felt the first time have consistently always been there I just needed to explore the other me who has been repressed for so many years.

[Madisyn]

My first time was losing a bet with my wife. Don't even remember what the bet was but she had me clean the house with a maid outfit, black tights, and heels. It felt great

[yyc_panties]

It was 3 years ago, was more of a drunken dare (with the girlfriend of the time). Who knew it would blossom into something more?

[Melissa18]

I was about 6 years old, I was in my mothers bed room and I saw this lovely yellow dress hanging in her closet, for some unknown reason I just had to try in ,on. When I put it some force came over me and I can still remember it like yesterday, it felt so comfortable, it felt like it was made for me?
Returned the next day and tried the same dress on, again and the same feelings, this is wonderful I thought. Then my father saw me and I knew something wasn't right, dad came in and explained to me boys shouldn't wear dresses. I listened to him, took it on board for a week or so, and i now knew not dress while he was at home, when he was at work I was back into the closet to try on another dress,same wonderful feelings and since then ive been hooked!

[DAISY LYNN DOKES]

If only my wife would manage to win a bet like that, I would be in heaven

[leeann_360]

I first started dressing when I was in 5th / 6th grade. I would try on my mothers things, yes, much to big, but still very thrilling. I finally found the courage to get my own panties and girls tshirts from the local Woolworths and it all grew from there.

[karencd#3]

Hi Leeann,
I started to dress later in life.i was in my thirties.i met a woman who wanted me to try on her clothes.i did and I was hooked.i have been doing it whenever I can ever since.My next step is going to be going to lunch with a man I know while dressed.i need lots of tips on make-up and removing it(I am married and need to be discreet.)I have had pics. taken of me dressed;but not in a passable mode.
thanks for the post,
karen

[KimCal]

Mid 20's.

[Julia Red]

I was about 6 but I remember it well, because I was caught.

For some reason I was alone in my sister's room and saw a pair of pink sandals (my sister was 11 at the time, and the sandals were VERY girly). I just felt like trying them on and it was so magical, so different from my boys shoes. One thing I loved was the fact that it had straps and buckles, and they were the very reason I was caught.

So while me and my boyish feet were enjoying this nice pair of pink shoes my older female cousin called me for lunch from another room and I tried to remove them desperately, to no avail. It was hard to unbuckle them. My cousin then walked in my sister's room only to find me nervously trying to take off the sandals. She looked at my feet, didn't say a word and just left. I managed to take them off seconds later and then went to have lunch.

I think it's funny that I was caught right at my first time. My cousin ignored this and never said a word about it to me. Oddly enough, I totally ignored female shoes for many years, focusing mostly on panties, shorts and tops. Now I love them. :battingeyelashes:

[Wildruler]

Saw some of my moms pantyhose hang drying in the bathroom as a kid and tried them on. I fell in love with how smooth and silky they felt.

[Bobbi McCarthy]

I was nine when I started to secretly wear my sister's panties. My sister Sue was a year younger, but nearly my size in everything! Initially I used the laundry hamper as my source of her underwear, but freshly laundered panties from her lingerie drawer were better still and offered the opportunity for some choise in both color or fabric, as opposed to the "panties du jour" that the hamper allowed. I would sneak on a pair of her panties whenever I found the opportunity, wear them all day and deposit them in the hamper without anyone's knowledge, or so I thought.

[Katie7]

WOW! most people started dressing very early in their life! I think I missed A LOT on that! well I shaved my legs when I was 15 didn't know why I'm doing it but I liked it! does that count? didn't wear any women clothing / makeup until I was 25. Started by wearing girlfriends panties and bras.

Katie x

[opaquetights09]

I guess my first post here should be about the first time I started cross dressing. I had to be about 11 or 12 when I first started trying on clothes in my grandmothers upstairs room. She always seemed to have nice summer dresses she would pick up at sales. I tried them on and would look at myself in her mirror and imagine I was a southern belle. I started trying on her pantyhose around the same time. There was not a weekend that went by that I did not spend time there dressing and playing around with her clothes. I've been wearing pantyhose and tights on and off now for 35 years and love every minute of it.

[vago487]

was trying on a pair of tights for me, gave me an instant hosiery fetish.

[SierraTsuki]

I was probably around 8 or so when I first crossdressed. While home alone, I tried on some of my sister's clothes. I liked the look of them in the mirror and it was a great rush of fun. I didn't really get semi-serious about until later in my teenage years though. I remember always having an interest in feminine clothing.

[TomboyBecca]

When I was a freshman in college, I tried on my gfs panties for the first time...and subsequent girlfriends panties :D It kinda just went from there.

[Rebekah_uk]

I have to say that it was in my mid teens, my dad's ex girlfriend had great taste in eighties fashion. She had lots of clothes she didn't wear in black bin bags. Thus were easy to borrow and return without to much issue

[Xandra]

Sounds wonderful, Lucy xxx
For me it was when I was about 16. Just one dress in the bathroom. it wasn't until I left home and got my own place that I really started putting on more things and it has just got more and more as the years have gone by. The first time I actually did the whole thing with full make up, shaved body, wig, painted nails, jewelry, stockings, basque, panties, high heels and not forgetting perfume was about 5 years ago.

Lucy Lou xx

Nadina, totally agree with that. Panties and stocking and suspenders and a short skirt. Wonderful. Lucy Lou.

[secretcd1]

11 years old. I was home alone and next thing I know I have on my sisters mini skirt, panty hose, bra, tank, and make up.

[Tami]

First time around 18 but only occasionally. Have worn my wife's clothes when at home on my own throughout our marriage but never said anything. We have since split up for non related reasons but are good friends so I told her. I have now spent 2 evenings at her flat wearing dresses with her and am now building up to asking her to help me with make up etc, I'm sure she will be happy to help.

[RachaelInLv]

from the age consensus I am seeing here I was definitely a late bloomer, I didn't start until I was 24 and already married to my wonderful wife.

[Rachell Carter]

I found a bag of clothes I think they could of been a crossdressers they were in some woods don't know what made me try them on bra nickes and suspender belt all in purple I put them on and loved it xx

[Diana81]

Fully, one month ago.

[laceslip]

Just wanted to share with you girls some thoughts I had written down on this obsession that I love!!

Did it start with your older s****rs or mothers lingerie drawers?
Sorting thru lace trimmed panties. Looking at hoisery drawers.
Looking at those catalogs and the extensive lingerie sections.
Sliding on that first pair of panties and being amazed at how they felt.
Finding that drawer full of slips and being taken back by all that pretty lace.
Letting a slip drop over your head and feeling it slid on your body.
Taking some of that lingerie to your room and trying it on.
Did you have the nerves to explore your Aunts or your neighbor ladies dresser drawers.
Was it "borrowing" some piece of lingerie that you had to have.
Did you end up with a collection of lingerie hidden away in your room.
Was it when you were in a department store and walking thru the lingerie dept.
Or when you got up the nerve to purchase your first piece of lingerie from that store.
The first time you had the house to yourself and found yourself trying on everything.
Piling all that pretty lingerie on the bed and writhing around on it.
Finding an old dresser in the attic with a drawer full of vintage slips.
The first time you wore a dress or a skirt.
Finding yourself trying to catch a glimpse of a peek of lace under a skirt hem.
Trying on that garter belt and a pair of stockings that was buried in your Aunt's dresser.
When you got the nerve to get a hotel room solely for the purpose and privacy of being girlie.
Choosing your girlfriends based on the assumption of there choice of lingerie.
Seeing your first adult film and finding the lingerie you saw to be more provacative than the sex.
Being in college and having a female room mate and rifiling thru there lingerie.
Having independence as a young adult, enough to dress whenever you wanted to.
Building a stash full of lingerie and keeping it hidden.
Finding that niche market and buying VHS tapes of lingerie tease.
Buying adult magazines and cutting out the best lingerie pictures and making a collage.
Finding a pair of heels that fit and being amazed at how they made you feel.
Hearing those heels "click" on the floor when you walked.
Wearing a wig and perfume for the first time.
Experimenting with make up and realizing how hard it is to make it look right.
Having a new found appreciation of a pretty face with perfect make up.
The first time you dressed all the way as a woman and how erotic it felt.
How nervous you were the first time you ventured out of the house dolled up.
Admitting to someone else that you had a "girlie" fetish.
Putting on your prettiest lingerie, your favorite dress and heels. Perfecting your make up and getting in the car and riding all over town feeling so sexy.
Spending an entire weekend as a woman.
Experimenting sexually being dressed and finding out how erotic it can be.
Spending way too much money on lingerie, clothes, make up, shoes and jewelry for yourself.
Discovering how much the internet could be a factor in your crossdressing.
The first time you were with another CD.
Admitting to yourself that this was a very deep part of you and that you really loved it.

Part two coming soon!

I hope this brings back some fond memories for you.
It certainly does for me!

xxoo

Mandy

[cdyoung114]

I remember trying on a bra around the age of 10... I didn't start buying clothes and lingerie until I was around 22

[Josette_Laroc]

About 9 or 10 years ago when we received an adult "toy" catalog in the mail, it came with a cute little mesh thong with some rhinestone word on the back. I tried to get my wife to try it on and model for me to no avail. After a while she told me, "if you like it so much, why don't you put it on?"
So I did, and made a big show about it. I am pretty sure that she didn't expect that I would. She got pretty mad.

[pajeantv]

Wow, Crossdressing for me started early, at age 7 or 8, started when a cousin (girl) came to visit my mother for a week during the summer. she was a little older than me but was about the same size. She brought a swim suit, dresses, and shorts, tops, Mom and her went out on day and I was looking at the swim suit, started by trying that on, WOW, the went on from there, sadly Mom came home while i was still in one of the dresses, i couldnt get undressed fast enough, She flipped out on me and wooped my butt, that just reinforced that i should look like a girl as much as i could. was in my late teens till i bought any of my own stuff, just dresses, or things like that that i could get at a thrift store.

[texasm31]

Just wanted to share with you girls some thoughts I had written down on this obsession that I love!!

Did it start with your older s****rs or mothers lingerie drawers?
Sorting thru lace trimmed panties. Looking at hoisery drawers.
Looking at those catalogs and the extensive lingerie sections.
Sliding on that first pair of panties and being amazed at how they felt.
Finding that drawer full of slips and being taken back by all that pretty lace.
Letting a slip drop over your head and feeling it slid on your body.
Taking some of that lingerie to your room and trying it on.
Did you have the nerves to explore your Aunts or your neighbor ladies dresser drawers.
Was it "borrowing" some piece of lingerie that you had to have.
Did you end up with a collection of lingerie hidden away in your room.
Was it when you were in a department store and walking thru the lingerie dept.
Or when you got up the nerve to purchase your first piece of lingerie from that store.
The first time you had the house to yourself and found yourself trying on everything.
Piling all that pretty lingerie on the bed and writhing around on it.
Finding an old dresser in the attic with a drawer full of vintage slips.
The first time you wore a dress or a skirt.
Finding yourself trying to catch a glimpse of a peek of lace under a skirt hem.
Trying on that garter belt and a pair of stockings that was buried in your Aunt's dresser.
When you got the nerve to get a hotel room solely for the purpose and privacy of being girlie.
Choosing your girlfriends based on the assumption of there choice of lingerie.
Seeing your first adult film and finding the lingerie you saw to be more provacative than the sex.
Being in college and having a female room mate and rifiling thru there lingerie.
Having independence as a young adult, enough to dress whenever you wanted to.
Building a stash full of lingerie and keeping it hidden.
Finding that niche market and buying VHS tapes of lingerie tease.
Buying adult magazines and cutting out the best lingerie pictures and making a collage.
Finding a pair of heels that fit and being amazed at how they made you feel.
Hearing those heels "click" on the floor when you walked.
Wearing a wig and perfume for the first time.
Experimenting with make up and realizing how hard it is to make it look right.
Having a new found appreciation of a pretty face with perfect make up.
The first time you dressed all the way as a woman and how erotic it felt.
How nervous you were the first time you ventured out of the house dolled up.
Admitting to someone else that you had a "girlie" fetish.
Putting on your prettiest lingerie, your favorite dress and heels. Perfecting your make up and getting in the car and riding all over town feeling so sexy.
Spending an entire weekend as a woman.
Experimenting sexually being dressed and finding out how erotic it can be.
Spending way too much money on lingerie, clothes, make up, shoes and jewelry for yourself.
Discovering how much the internet could be a factor in your crossdressing.
The first time you were with another CD.
Admitting to yourself that this was a very deep part of you and that you really loved it.

Part two coming soon!

I hope this brings back some fond memories for you.
It certainly does for me!

xxoo

Mandy
So many of those hit home. Thanks for a few wonderful memories.

[Tanya+]

I don't know exactly how old i was, but i remember my mum demonstrating how to put socks on, by putting her pantyhose on, and generally being around her as she dressed..my dad was usually at work already.

But my first time was when i was about 5 or 6 my friend wasn't home and the little girl next door invited me to play, she got me to put on a pretty lemon dress and buttoned me in, some adults called to her and were coming over..i left the dress on the grass and ran away cheeks burning; didn't really start wearing my mum's clothes until puberty; i knew what i liked pretty quickly. About the same age (5ish) my friend rolled me up in a carpet and i loved the feeling of restriction..tried to reproduce it. Xdressing was more a spice to being restrained since puberty.

[CrossRose]

My first time was when I was around 4 years old and I was wearing a pink princess gown and those fake plastic slippers from cinderella story :D

[Emily43]

I used to stay at my aunties a lot when i was 7 or 8 and remember looking through her draw in the room i used to sleep in...was full of stockings and french knickers...i tried them on...the rest is history.:)

[Erica Grace]

I think I was 12 or 13 and went through my stepmoms closet, she had so many dresses and I tried each one on. Happy to have my own now :)

[Jaidyn]

I remember trying on my sisters ballet suit when I barley knew how to dress myself in my own clothes.

[AprilMayy<3]

Oh jeez, when I was about 10 or 11. Walked in the bathroom one morning during summer and my sister was drying her bras she had washed over the shower rod. She had all 4 just hanging there, and I couldn't resist :P I think that's when it started, but I only got serious with it about when I was 14 or so.

[CD Stephanie]

Just wanted to share with you girls some thoughts I had written down on this obsession that I love!!

Did it start with your older s****rs or mothers lingerie drawers?
Sorting thru lace trimmed panties. Looking at hoisery drawers.
Looking at those catalogs and the extensive lingerie sections.
Sliding on that first pair of panties and being amazed at how they felt.
Finding that drawer full of slips and being taken back by all that pretty lace.
Letting a slip drop over your head and feeling it slid on your body.
Taking some of that lingerie to your room and trying it on.
Did you have the nerves to explore your Aunts or your neighbor ladies dresser drawers.
Was it "borrowing" some piece of lingerie that you had to have.
Did you end up with a collection of lingerie hidden away in your room.
Was it when you were in a department store and walking thru the lingerie dept.
Or when you got up the nerve to purchase your first piece of lingerie from that store.
The first time you had the house to yourself and found yourself trying on everything.
Piling all that pretty lingerie on the bed and writhing around on it.
Finding an old dresser in the attic with a drawer full of vintage slips.
The first time you wore a dress or a skirt.
Finding yourself trying to catch a glimpse of a peek of lace under a skirt hem.
Trying on that garter belt and a pair of stockings that was buried in your Aunt's dresser.
When you got the nerve to get a hotel room solely for the purpose and privacy of being girlie.
Choosing your girlfriends based on the assumption of there choice of lingerie.
Seeing your first adult film and finding the lingerie you saw to be more provacative than the sex.
Being in college and having a female room mate and rifiling thru there lingerie.
Having independence as a young adult, enough to dress whenever you wanted to.
Building a stash full of lingerie and keeping it hidden.
Finding that niche market and buying VHS tapes of lingerie tease.
Buying adult magazines and cutting out the best lingerie pictures and making a collage.
Finding a pair of heels that fit and being amazed at how they made you feel.
Hearing those heels "click" on the floor when you walked.
Wearing a wig and perfume for the first time.
Experimenting with make up and realizing how hard it is to make it look right.
Having a new found appreciation of a pretty face with perfect make up.
The first time you dressed all the way as a woman and how erotic it felt.
How nervous you were the first time you ventured out of the house dolled up.
Admitting to someone else that you had a "girlie" fetish.
Putting on your prettiest lingerie, your favorite dress and heels. Perfecting your make up and getting in the car and riding all over town feeling so sexy.
Spending an entire weekend as a woman.
Experimenting sexually being dressed and finding out how erotic it can be.
Spending way too much money on lingerie, clothes, make up, shoes and jewelry for yourself.
Discovering how much the internet could be a factor in your crossdressing.
The first time you were with another CD.
Admitting to yourself that this was a very deep part of you and that you really loved it.

Part two coming soon!

I hope this brings back some fond memories for you.
It certainly does for me!

xxoo

Mandy

A lot of this hits home for me. I was about 11 or so I guess and always looking at the lingerie section of JCPenney and Sears catalogs. I was doing household chores and gathering up the trash around the house to take out. On my Mom's side of my parents bed was a small trash can. When I went to empty it, all that was in there was a pair of pantyhose that she'd thrown away because of a run in them. I pocketed them so I could try them on later. When I was alone in my room later, I put them on an immediately became aroused. After that, when I was left home alone, I would go exploring Mom's lingerie drawers. I'd try on her bras, slips, and whatever else I could find. I'd stuff the bra cups with socks. Sometimes I'd even try on her dresses and swimsuits. I've been hooked ever since.

[ngzero]

I guess somewhere when i was 8-9. I asked my cousin to paint mt nails, and put lipstick on me, it as fun :)

[KayleeAnn]

I think I was 9-10, but it was just small stuff like wearing panties but as I grew up, I started getting more and more clothing and dressing more and more. I still haven't gone out in public dressed but I'm working my way there.

[tammie]

My first time crossdressed was by my mom when she was feeling playful and I wore my older sisters outgrown party dress with lace panties lacy socks and maryjanes . What I remember most was being stimulated and embarrassed both , mostly because my older sisters
little friends saw me and laughed.

I tried on my first bra at age 14 because a cute MILF told me I should be wearing a bra , since as she said ,my tits were bigger than hers. Again I was both embarrassed and stimulated . A week later I saw my older sisters lace underwire bra on the floor of her bedroom , being home alone I picked up the black lace underwire bra and as I was leaning forward walking my hands down the band to hook the brassirere behind my back like my mother, and felt my breasts in those lacve cups I almost feinted from the sensation.

Then I knew I was a crossdresser , it fit me like I had been measured for it , I looked in the mirror and I had 36B breasts like a woman , and I was so excited , I decided to take it and wear it for awhile (my head was spinning) and as I was leaving her bedroom I saw the
matching (Vassarette) LLPG with lace around the legs , so sexy and all sheer black lycra, and decided to take it too , ohh my I can still remember them .

[Lacyfem]

I remember it like it was yesterday as it was so exciting. I was ten and parents had a cocktail party and then they all went out to dinner. There were all sorts of drinks and liquor left around and I decided to sample the booze. My Dad drank Jack Daniels so I helped myself to a nice pour of it and within a short period was feeling really good. Sexually I had already started to masturbate as an older friend had taught me and was sexually involved with my older brother. For whatever reason when I got myself drunk I dropped what I was wearing and went into my mothers hamper and put on her full cut nylon panties and her bra. She was a very full C cup so I stuffed the bras with the other panties from the hamper. I was hooked as it felt so good and being so young not sure I understood my feelings then but they were definitely sexual as well as feeling very fem. I had always loved to watch my mom dress and envious of her beautiful body and wonderful lingerie and cloths she had. There is a thread here on putting on our bras as I loved watching my mom as she would put the bra on with straps on shoulders and then lean over so her beautiful breast would hand down and she'd then pull the bra over her breasts, stand up and connect the hooks behind her back. She did it so easily and it was sexy. From this day on I was into her hamper a lot as well as other things she wore. As for that wonderful night, I got pretty drunk, did throw up and the following morning my Mom knew I had gotten sick and knew why I got sick. However, she never knew that I also started a lovely fem crossdressing career wearing her beautiful lingerie.

[Abbygirl]

I can't remember exactly how old I was, but I can remember that when I was young I used to feel guilty/shameful about trying on panties and other things I would find in the "dirty-clothes" hamper Mom kept in our bathroom. I can remember vowing that when I turned 10 years old I would finally quit doing it. I remember I had been doing it for years and felt it was about time I stopped. Turning an age in the double-digits seemed like a good target for quitting. Of course I never quit. If I had to guess I'd say I was 7 or 8. I don't feel guilty anymore.

[Paula_Femme]

When I was a child - 4 or 5 maybe? - practically all the neighbor kids, and so all my friends, were girls, and I do distinctly remember wishing that I was a girl, so I'd be just like them! :battingeyelashes:

Then later - 10 to 12 is the best I can estimate - I remember trying on my Mothers shoes, and I've had a heel fetish ever since! :lovestruck:

The first time I seriously cross dressed was in my early 20's when my girlfriend suggested I "dress-up" while I was doing the ironing... the rest is history!!! :)

[wanda66]

I was about 10 . I had no sisters so I got moms stuff first the panties , bra . Them I startd with the dresses, and such ..this when on untill my late teen. Mid 30's ....the wifes panties. Then I went on the road to work , away 5 days a week . I got bold and began buying my own panties and bras .getting older my pecks got a bit larger and filed my bra some. I enhance them now to a 38b... I have writen this down a 100 times on paper this will be the first time it will be read by someone.. Iam into my 60's now and if feels good to talk about how I got here. I know many of us have similar stories . I hope I'm not boring any one...thank you for the place to talk....

[Adriana]

I believe I was 8 or 9 when I decided to put on my very first pair of tan pantyhose and has grown from there. I started buying shoes and more clothes by my late teens, then had a dry spell as life got in the way. Though, that changed once I got married, as I decided to tell my then GF that I enjoy being Adriana and she was very open and understanding. Today we both have fun shopping together and picking clothes out for either of us to wear :).

[Brendastevens47]

I was about 11, the late 50's. Girls had always interested me, and I had had an urge to wear girls silky panties for many years, and in those days boys were just not supposed to dress up like girls, so I had resisted this temptation, but broke down, seeing a pair of mom's silky white panties hanging on the clotheshorse...I slipped them on...what a thrill...and here I am today, at age 66, dressed fully as a woman...and enjoying it as much as I did then. I Love Cross Dressing so so much.

[Tasha'sLaboratory]

I think I was 5 or 6, my cousins panties. I just needed underwear and she gave me some. I liked them, I think they had multicolored stripes on them but its hard to remember for sure.

I've tried wearing panties since then but by themselves they didn't do much for me other than make me a little bit uncomfortable (physically).

[Aelita Nolan]

I was about 20 (it was only a few years ago and during the summer). I had expressed interest after I had seen my (then) girlfriend wearing a dress to a formal dance in High School (that was the only time I had ever seen her wear dresses, she was also still in High School at this time (we started later than most people)). I told my mother because I was to worried about my parents finding out, so I thought that I should just say something right then and there. My mother gave me a pinafore that she had. I was (and still am) in college at the time, but I never expresses the desire to dress in my room in the residence hall (you can probably guess why).

[Jessika]

I guess ive never really thought about it, i think id have to say i was around 10 or so, I had thought about it a LOT before then though.

[Trinity Sue]

I started when I was 10 , wearing my neighbors daughter's bra and undies. I would borrow them from the laundry room and return then after I was tired of them. When I was 15 ,I met another dresser and together we would borrow or buy things to wear. He moved away after high school and I never saw him again. I married and stopped Dressing until we divorced 10 years later. I started dressing again and was able to pass. I would go away on the weekends to do this ,coming back from one trip I met my second wife and stopped again. I tried several times to talk to her about it ,but she thought the person who did this was sick . We divorced after five years and I started dressing again. It was easier to buy underwear and clothes , the girl at the hair salon would do my hair and makeup . Nails and pedicures also done by a cd friendly shop ,omg things were great !
Then I met my third wife , yes I stopped , we moved away . I had an emptiness and long for it . Then one day while I watched her dress , I said something about dressing to her , she smiled and we talked . We shop together and have pedicures ,, I have been taking baby steps with her . So far things are good .

[Millie.Graham]

I first wore tights when I was about 5 or 6 as a Halloween costume. I fell in love with tights then. I am not sure what eventually drove me to try on the rest of my mom's clothes. But around the age of 10 or so I started trying on her clothes. I fell in love with a blue and green tartan print pencil skirt and some heels that I love to walk around the house in when I was alone. Great memories.

[lindsey89]

The first time I truly remember dressing up was when I was 4 years old. I was really good friends with the twins across the street, one was a boy and the other a girl. One day we were playing school and somehow convinced them that we needed a second girl to be a student since Sarah was playing as the teacher. after this I offered my self to be the girl and suggested that I should change to play the part :)

[Kristencdct]

I first thought about it around age 7. I noticed how the girls in school ere dressed and wanted to be like them. Around age 10, I tried on a skirt for the first time. After that I would sneak into my Mom's or sister's closet to try something on whenever I had a chance. I've been hooked ever since.

[larissa-laurie]

My first real experience was age 13 or 14 when my sister dressed me up in her school uniform. She had me in all the lingerie, skirt, blouse, vest, wig, and makeup. She commented I was a pretty good looking girl and I should go to class with her sometime. (Like that would happen). I asked to do that the next night too and she did dress me up, but I had to slow down so the folks did not get suspicious. But I was hooked both line and sinker. I then got a pair of her panties and pantyhose and hid them so I could wear them at night in bed and enjoy the feeling. It has been on and off again ever since.

[JennyLynn]

4 yrs old Mommys silk stockings

[joanne51]

With me it started with a short black open girdle out of my mum's drawer, but then finished up within a short time working through my mum's entire collection of clothes (back in the sixties). Although it would be almost 40 years before I started acquiring my own, and learning makeup, along with wigs, hair removal, the works. It was that initial imprinting all those years ago, that turned the light back on in my brain.

[Wanna be Heather]

At 6. After few encounter with boys

[helenacross01]

58. just experimenting but it is erotic.

[heatherdress]

I like this thread and, unlike other threads with repetitive opinions and suggestions which I tend to by-pass - I like to read each experience entered here. They remind me of "my first time" - very special, very intimate, very sexy, exciting, life changing. I feel happiness and a share a bond with each person as I read their "first time." I hope this tread goes on, and on....

[Xandra]

I am delighted this thread is still active, Heather!QUOTE=heatherdress;3488919]I like this thread and, unlike other threads with repetitive opinions and suggestions which I tend to by-pass - I like to read each experience entered here. They remind me of "my first time" - very special, very intimate, very sexy, exciting, life changing. I feel happiness and a share a bond with each person as I read their "first time." I hope this tread goes on, and on....[/QUOTE]

[irene9999]

When I was like 8 I grabbed a dress of my mom's that really caught my eye and tried it on, I think that was my first time ever. At some point in my early teens, I grabbed some stuff from my sister and tried it on, so the desire to dress was always there I think. The first time I fully dressed was in my mid-20s, when I was able to get a full outfit and a wig and tried it on

[Ben Grimm]

Sadly for my SO, it wasn't until after we were married and had 1 baby. It's been a hot button topic for almost 9 years. I have taken the honesty route with her for many years now and still stumble through it. She's allowed me be a member on this site to do more research, sharing, and getting me to a better place in life with my CD and the male / female balance.

[Christina Sevilla]

I started out by trying my mom's panties when i was about 7. Then starter trying her bra and dresses whenever she was out.

[Athena_]

I was around 8 when I would try on mom's lacy panties and a bra from the hamper in the bathroom. This, of course, started me down the path. On of the happiest days of my childhood is when my mom and sisters dressed me up as a girl for Halloween when I was 11. White party dress with a pink bow. Wig, makeup, nylons, panties, and a sock stuffed bra. I had such a great time. They still do not know about my "curious habit" as my wife calls it.

[DaniF]

At 10 I tried on my mom's one-piece swimsuit and loved it!

[Lea]

I do not remember a time when I did not dress.

Mom wanted a girl and at a young age used to dress me as a girl. Not all the time but a lot of it. Just before I started school she had my hair cut short and that was the end of that.

I kept dressing when I got the chance.

I found out about being dressed as a girl when I talked to my dad as he was dying. I brought him a picture of my daughter in a dress so he could have pictures of the family around him. He told me that it was a picture of me. When I said it is his granddaughter in a dress he told me that it was me and he told me the story of mom dressing me and treating me as girl.

Mom told me she wanted me to be a girl, that she kept my hair long, and people thought I was a girl but never could get her to admit to anything else. She is still alive but having medical issues I would really like to learn more while I can.

About ten years ago mom, my wife and myself went out to a Halloween party all in dresses in a group theme and she enjoyed that.

[StaceyJane]

I don't even remember when I first wore my mom's clothes. Junior High? I just know I always wanted to be a girl.

[Amy_blueyes]

When I was probably about 10 yrs old. There Was girl down street and she was tom boy. She would pretend to be boy and I would be girl. That Was happy time

[Jaclyn]

I was 8 or 9 and my costume for a Halloween party i dressed as a girl. BEST PARTY EVER!! Occasionally all my live i would sneak wearing panties, bras and nighties. This past January my wife found out and has been really supportive, although shocked. Now I dress a lot more, just bought my first wig this past weekend.

[michelle az]

as all of us very young moms petticoat around 8

[StephanieDragg]

when I was 8-9 trying on my moms nylons she hung over the shower rod

[GirlyTGreen]

Around 5 or 6 my first was much like Tasha's, i needed a pair and my aunt gave me a pair of my cousins panties. Something about wearing those panties felt right....then i started trying on my mom pantyhose and eventually my babysitters dresses when i got the chance to sneak in her room. Its grown from there ever since.

[bonni]

Early twenties but I don't know what triggered it.

[Underdressed]

Aged 5 or 6 trying to get plastic christmas stockings on under the table (after I had eaten all the sweets), aged 10 wearing mums heels, aged 13 progressed to nylons and suspender belt. it's been a long journey.

[kymmieLorain]

I think I was 12-13 I tried on a pair of my sister panties. I had the love for lingerie much farther back than that.

Kymmie

[Erica William]

Wow what an awesome topic. It's taking me a few days to get through to the end of this thread , but its got me really thinking. I can remember maybe being 7 or 8 years old going to my moms dresser drawers. But when I was 10, I found a books that my dad had. They were these little paperback dirty novels with a story line like you would find on literotica or somewhere. Most of them were straight porn type stories. But there was one that started out with a young boy dressing in his sisters clothes and getting caught by his father. The book itself was about incest. But little Tommy was always made to dress in his sisters clothes. And as I sat there reading this book I was so incredibly aroused. And when I went home after the end of the summer I took it with me. I can remember a week after I returned home I was stealing the neighbor girls panties so that I could wear them. So I think that's when it really clicked in my head I like this and not only do I like it I love it. So it's been on and off at different degrees for most of my life. This time I no one to answer to but me.

[sally38]

i did start dressing at age 15 mom stuff got makeup at 17 now ever time i can love it

[trisha11]

I was 7-8 and I found my sisters satin panties and matching bra, from that point forward I was hooked, have never looked back

[tiffyjo]

I was in 5-6th grade in school. My mom had a "rag bag" in my upstairs closet she threw old clothes in to use for rags at a later date. I was looking through it once and found some of her old panties. I had to try them on,,, and that was it, I was hooked. Panties and pantyhose mostly. Expanding soon!

[JessicaJJ]

Age 6-7 i think, my best friend then was a girl the same age and used to spend a lot of time over her house on sleep overs, she also had a sister and we used to hang out a lot and get very messy as kids do but my clothes used to get messed up so my gf and her sis used to give me thier clothes to wear, i was never short of things to wear lol they always made sure i was well looked after lol at the time i never thought anything of it, it beats getting cold and having nothing to wear so yea i was quite young, lol its no wonder i like dressing like a girl.

[Angie G]

It was better then 50 years ago. Up in the attic. Shoes adress undies when I could find them.Loved it from the start.I think I was 10 or 11 at the time.:hugs:
Angie

[Alexand]

At 12, I wore my mom's pantyhose. It was a new one right from it's package. I wore it and I felt so high I could not believe it! After that I carefully put it back into the package and the drawer. Now that I think about it my mom could definitely tell that something was wrong with her "new" pantyhose when she opened it, but she never said anything. After that, I remember stealing 2 pairs from a neighbour's yard where they where hanging to dry. I kept them hidden in my room but my mom found them after a couple of months and threw them away, again without telling me anything. Later I started wearing my teenager sister's bras and panties (no teenager wore thongs back in the early 90's) and I was wishing I were a woman. I am not gay, I never looked at or thought of another male in an erotic way but I know that I would feel more comfortable being a woman.

[newbiecdmd]

I wouldn't calling it totally crossdressing, but in 6th grade trying on friends' sisters panties and pantyhose...

[fun4metoo2004]

12 or 13. Loved it but really did not understand the feelings then.

[redwildberry7]

I dressed up around middle school. I went all out. I looked really hot, and danced around a little. It was so amazing. I did it every time I had the chance.

[Thom2332]

Summertime last year, I was sitting around in the usual mens baggy cargo shorts thinking to myself damn these things are uncomfortable. I envied the girls who got to walk around in short shorts and tank tops. I bought a couple of pairs of women's shorts to wear at home. I wore them off and on and am really just now starting to get more into dressing.

[savannaxdrsser]

The first time i started wearing was when i was around 11 or 12. For some reason puberty hit and i got an interest in wearing my sisters panties. After that I would dress on and off, but never fully. Started dressing more fully last 5 years and it has been wonderful.:battingeyelashes:

[satinsam]

Back in the 1960s..
Found mum's silky slips, bras, girdles, stockings, make-up and heels..
Seemed natural to play dress-up as liked girls and what they wore..
The rest as they say is history..

[MeganDay]

I was 14, mom's panties, slip, panty hose and heels. Added a dress later. Due to circumstances, I all but stopped about a year later, and completely stopped by the time I was 20. Restarted again, very recently.

[tightsplease1986]

Well I have to say that this isn't the first time I've cross dressed! When I was about 11 years old I was getting to the age where I was hitting puberty and became curious about my sexuality. My mum showed me this black and white skirt that she had and even let me try it on. I loved it, so I kept putting it on. However, as the years went by I became more and more nervous about putting it on and I certainly didn't want my parents to find out, so I would wait until they went out and left me home alone, and nick it from her drawer! I did this on and off until I was about 15 when I just stopped. Until, that is, one day last week when I suddenly got an urge to do it again. It started with me shaving my legs, then making DIY skirts out of old leisurewear shorts, and this week I got some tights. :)

[sophia7]

Probably around age 10 or 11... I used to paint my toe nails red, wear my mums stockings and black stiletto heels. I started to wear my first proper girlfriend's skirts and tops around age 17.

[StephanieinSecret]

I think I was 10 or 12 the first time I tried on a pair of my sister's panties. I knew I shouldnt be doing even then. I remember being immediately jelous that girls got to wear such soft fabrics all the time- I felt almost cheated! From there, it just expanded, from panties to bras to outfits. I love it haha

[sophia7]

Probably around age 10 or 11... I used to paint my toe nails red, wear my mums stockings and black stiletto heels. I started to wear my first proper girlfriend's skirts and tops around age 17.

[Dora]

What really stands out to me is when my sister got married and at the time I was living at my parents house, my sister after the wedding brought over all the bridesmaid dresses, my parents went on vacation and I decided to try on the bridesmaid dresses, ever since then I have been alot more embraced to crossdressing.

[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!!! :battingeyelashes:

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 :D 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.

[Mishell]

I was about 6. Mom always wore pantyhose, 24/7 and I loved how her legs looked. I took a pair out of her hamper and tried them on. It led to her skirts, bras, slips, dresses, heels and wigs, as I got older.

[Wiccle]

Used to wear mum's shoes in bed when I was 12.

Bought my first dress at 25. "Late-starter" doesn't even cover it. I sometimes wonder what it would have been like to do it at e.g 16. The logistics would have failed at some point I'm sure......

[BeatriceBlack]

I was about 12, hitting puberty and wondering how girls "worked", and investigating how girls' clothing worked led to me trying on a bra to see how they went on and came off... and it felt so good, I kept going.

[Alex PL]

About 5 - 7 sister's pantyhose ))

[kellyanne]

... age 8 or 9 ,I wore my mother's bathing suit, My interest started at 3 or 4.
I vividly remember the beautiful sounds of my grade 4 teacher's undergarments as she walked by... the shh shhhh of fabric on fabric.
It sounded beautiful and I wanted it for myself.

[Sc0rp10N]

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

nope, I was too busy feeding my animal masculinity. As described in other thread responses, it was likely brought on by 2 things that only came together at that time- my wife refusing to dress sexy for me, meaning our relationship was lacking in femininity, and that I was embarrassed about her doing me as a guy with her toy. It felt much better to pretend I was a girl. That sums it up rather snugly, but there's a lot of periphery.

[Vicky Peters]

I was in my early teens staying at my aunt's house for the weekend. She called me to zip up the back of her dress, no problem. That one simple act led me into xdressing. I had to figure out how she got everything on. She wearing a longline bra and a zipper OMG with a slip. After she left, I discovered the hidden joys that were in the dresser.

[heather88]

I got into when i was in elementary school. i dont know why but it was just something i did when there was a window to do it in. i wish i could read my mind back then, have a pair of panties on and curling up on the floor. i wonder why that was.

[~JessM~]

My sister tells me about age 5, I don't remember that tho, I do remember at about age 12 my first dress tho. Pink satin dress in the older "puffy" style :)

[pattysues]

I was around 6. Most friends that I can remember where girls then. And I can remember one of the girls wearing hose. I was so jealous, so I tried my moms on. From there bra's, dresses, wig.

[alexakennard]

I tried on a pair of women's satin gloves when I was an 8th grader. I loved the feeling of it and it's only grown on me. Now I like to wear dresses, heels, and full-blown lingerie. It's a sexual feeling rather than one of wanting to be a girl. I just feel sexier in women's clothing!

[sabrinaA]

My first time would have been when I was around 10 years old. Tried on a pair of pantyhose too.

[VickiTheGamer]

Around 5 to 6 years old. I was not yet in Kindergarten yet. Put on what ever I could of my sisters that fit.

[Laura28]

I am Guessing around 7 or 8 tried on my mothers stuff, i think my first article was her slip, and it progressed from there. I remember the first time i tried her lipstick i was scared i wouldnt be able to get it off, LOL. Been hooked ever since.

[Bryanne]

Around 7 or 8, I tried on my sister's dress. Then, around 12 or so, I fully dressed on night when home alone -- panties, nylons, slip, bra, dress, makeup, and I became absolutely hooked.

[bill1962]

Around 12 or 13. I had been watching Get Smart and I liked the 'damsel in distress' theme. So I borrowed one of my mothers' dresses (very short on me) , pantyhose and bra. I knelt in the bathtub, started filling it with water. I used to imagine that I was trapped in a phone booth that was filling with water. Strange, I know but it's my first memory.

[Aldoreeq]

I think I was around the age of 6.

[calliekat]

At about the age if 11 or 12. I first tried my sisters one piece swimsuit. About the same time, I also tried on her gymnastics team leotard. .... I was always caught, and it never went over well at all.
I stopped.
Until I was about 40 and made a "deal."
I worked in a hot restaurant kitchen. Always envied waitresses in there skirts. So one saying "joked" with thedinningroom manger saying" if I wear a skirt. Can I wait tables?" She replied "if you war a skirt. You can do whatever you want."
I called her bluff. And I got a skirt. She didn't know that to say accept. "I didn't really expect you todo it!"
Surprise!
And IMO dressing has snowballed from then.
(Side note) I never did wait tables that day. But that was rather exiting and I dress in everything. But... In the closet.

[Saepe]

When I was about eleven, I had a curiosity about what it might feel like to wear women's underwear. So I took a pair of scissors to mine and did the best I could. It didn't take long for me to figure out that a bikini shape was improperly suited to holding my junk, but in retrospect I blame that on insufficient leg-hole elastic (which had all been cut off to give the new shape its form).

Then I pulled a bit of a u-turn in the next couple years. Lord of the Rings had just come out, and I was obsessed as any boy could be with Frodo Baggins. I wanted to grow out my hair to be like his, dress up as him for Halloween, carry around the One Ring on a necklace, et cetera. Eventually, after growing my hair out to about shoulder-length, my infatuation with the hobbit subsided and I got tired of people saying I looked like a girl, so I got a buzz cut.

CD urges flared up again at about sixteen or seventeen. I was finishing high school, still discovering myself, and wondering again what it would be like to wear female undergarments. At this point, the easiest thing to do was to knick some of my mom's. It's only ever increased from there, and I started growing my hair again at eighteen.

[chloecd1305]

7 or 8, mom's girdle and pantyhose

[Nikki_Taylor]

I was about 4 and living with my grandparents as my parents were separated and going thru a divorce, It was the late 60,s and they were in their 40,s and every weekend used to have parties in their basement, my sister and I used to sneak out of bed and sit on the stairs and watch through the railings all the women in their beautiful cocktail dresses beautifully made up, drinking martini,s listening to Dean Martin and Frank Sinatra. My Grandma would let me have my naps in her bed and would often find me fast asleep in her stockings that she would leave on the bed. After the divorce My sister went to live with my Mother and My brother and I went to live with my Dad, I wouldn't see my sister again for 10 years. My father remarried and my stepmother who was only 22 always resented me, Growing up I was small and often mistaken for a girl, although I didn't start really dressing until I was about 12 or 13 one summer when my parents were at work when my brother and I went into their room and discovered all of her sexy lingerie and would dress and play Mommy and Daddy.

[KittyD]

Uhm... think I was about 4-5 years old... the rest history :)

[Betty-Lou]

Around 10 or 11. First my sister's panties, but since she was smaller than me they hurt o I quickly graduated to my mother's nylon panties and dresses.

[ashley_addams76]

My first time was with pantyhose.

[nikinylons]

After a long infatuation with pantyhose and puberty starting to kick in, I put on Mom's L'eggs Sheer Energy and was hooked. They are the foundation of my fem side and CDing. From there, I put on mom's leotard with them and lipstick. It was an incredible rush that came over my body. The feel of tight, smooth garments, and the look, smell, taste, and feel of lipstick. Still feel the same today about it, except now, it has evolved into dresses, full makeup, nails, wig the whole 9 years baby! YES! Love it and love my pantyhose and heels!

[Nadia Pinky]

around 11 or 12 it was nice crossdresser and feeling more feminine than now

[Rachel Lea]

At the age of 6 or 7. My mom had her old heels and purses in our toy box played with them quite a bit. But 8th grade pushed me over to pantyhose and then I was hooked.

[jackie_p]

I was 8. Tried on my sisters old majorette uniform. I loved everything about it and still remember it vividly after 47 years.
Have been dressing up ever since.

[Colleen03]

The first time was when I was 10 years old. I took note of my Mom's & sister's swimsuits and when I saw them drying in the bathroom I saw it as a glorious chance to try one or both on. So I did and loved how it felt. I loved the tight, body hugging feeling and have been hooked eversince. I remember my Mom asking me why I was in the can for so long so I lied and said I was sick to my stomach and, well you get the picture. Luckily she bought it. Shortly thereafter, since my Mom & Dad have been separated since I was 7, my dad's x girlfriend had this hot looking pink one piece that I just had to try on, so when the opportunity presented itself under the same circumstances I tried on that pink suit and stared at myself in the mirror for a few minutes just noticing how sexy it looked on me and how I loved the shiny spandex material, then it was interrupted by a loud rap on the bathroom door with my hard ass father saying "What the hell are you doing in there!!??" So I made a few fake puking noises and told my Dad I was puking in there so luckily he bought that too. 30 years later I have about 15-20 swimsuits and I am always looking for more.

[Felicity_CD]

My cousin made me try on her ballerina outfit when I was about 8, her and her sister had been left to look after me. It was fun but I was only 8.

My first voluntary cross dressing , I was probably about 12/13 and I tried on my cousin's (a different one!) bikini. I loved it, wasn't long before I was wearing her underwear and it all went from there!

[Tera bytes]

My grandmother sparked my curiosity in pantyhose which later lead to full on crossdressing.

[orthotech58]

When I was around 8 or 9 I would lock myself in my mom's room and take a pair from her drawer and put them on.

[emily606]

Hi, I posted this exact post in another thread when someone asked me why I was asking about first time experiences. This is how I started. My first time was unpleasant, over time, I realized I liked it:

In 1962 I went off to a summer day camp. The day camp was located in Calumet City, Illinois, surrounded by what was still farmlands and forest preserves. The owner and director had been in that business for years and was a respected PE teacher in the Chicago School system.

I think what happened to me could be described as the perfect "how to" manual. How to rob a young boy of confidence, self worth, and dignity with a single insensitive and perhaps a crimminally abusive act. Near the end of the summer, the camp invited all the parents to spend an afternoon visiting their sons and daughters at activities and to watch each age group perform some kind of skit.

Some time prior to this visiting day, my age group was gathered into the drama hut and we were sat down with our counselor and there was a lady who seemed to be in charge of the show. Our counselor said, "We'll sing a song and half of you need to play girls. Raise your hand if you want to be a girl?"

Some of the boys laughed, but I thought, "want to be a girl?" Who would WANT to be a girl in a skit for everyone to see? I couldn't imagine and no one volunteered. The counselor asked again and then said that if no one raised his hand, he'd choose. Then he declared that his first choice was Mike. As in me. A chorus of laughter rang out amongst the boys. He continued and, in a pattern I couldn't discern, chose who'd play boys and who'd play girls.

In retrospect, I suppose, I was chosen because I was cute, small, and not one who caused this young man trouble at day camp. Of course, those qualifying traits meant nothing to me. My companions who'd be allowed to portray boys quickly cut to the core issue by taunting the so called "girls." We were told we were "fems," sissies, in fact they declared we were girls. I felt dread, humiliation, and even a bizarre guilty notion that being chosen corroborated a truth.

I was too embarrassed to tell anyone. I didn't tell my parents. I had this belief that somehow I'd get out of doing it. I'd pretend to be sick. Hopefully someone would offer to trade parts or who knows, maybe a big meteorite might smash the Earth. As a seven year old, I didn't know what to do and I was too ashamed to seek help.

As we rehearsed for the show, the drama lady paired each "girl" with a boy and we were taught a love ballad. We were told to sing and walk around the stage arm in arm. Parent's day arrived, and I'd convinced myself that if I simply, meekly, performed, most likely no one would have any idea of what I had done. After all, I'd be dressed up as a girl so who would recognize me? If asked, I'd deny it and undoubtedly get away with it. How painfully naive and innocent a child can be.

My dad, to my relief, was not going to leave work to attend, but mom came. She had no idea of what I was battling inside. The parents were herded into the drama area. We were told that all of the "girls" were to go to Lou's, the camp director's house, to get ready.

He was there, along with that lady in charge. We took off our pants and tee shirts and each boy put on white tights and we were put into a white schoolgirl (circa 1920?) style dresses. Then, one by one, this lady applied makeup onto us, eye liner, mascara, rouge and lipstick. Each boy was fitted with a kind of bonnet that had curls attatched which hung down onto our faces. I looked at myself in a mirror and felt a wave of relief, in the belief that I was unrecognizable. (In retrospect, I find the amount of make up that was used on 7 and 8 year old boys odd in itself.)

The lady told us that she needed to leave to start the show, but that we should wait with Lou, we should sit and watch TV, and be careful not to mess up our makeup or our dresses. Lou carried in a tray of lemonade and he asked me to stand up. He asked me if I was being a good little girl and I didn't know what to say. He reached under my dress and just grabbed my crotch. He laughed and said that I was a very good girl. The other boys laughed. I don't know how old I was before I realized that he wanted to see if I was hard under my dress. I think he was a pervert and he was getting off on all of us sissified boys.

Next it was our turn to go on stage and I still believed that no one would recognize me. Of course, I heard my name called in a jeering manner as we walked toward the stage, but that was nothing compared to the roar of laughter as we began our song. Quickly, it was over and I ran as fast as I could back to Lou's to get out of that dress and to furiously wipe off all that make up. It didn't come off so easily and until I got home, I bore a shameful kind of Scarlett letter or temporary tattoo that identified to anyone that day that I had been a girl in the show. I was so ashamed of myself.

I don't know how the others who stood on stage that day felt because I never talked about it again. I believed that if I blocked what had happened, it was as if it hadn't happened. I denied to my friends that I had played a girl. When they teased the crap out of me, I lied about having been a girl and I denied it. They knew I was lying and I knew that they knew I was lying, and unwittingly I gave them more fuel for their taunts. Some friends didn't limit their taunts for just that day, but for weeks and some felt the need to bring it up for years.

Over time, I felt an odd attraction to crossdressing. I'd see the three stooges in drag and it mystified me as to what led them to be crossdressed. I had dreams in which I found myself being offered the chance to wear a dress to school. When I'd put it on, in the dream, it felt nice and I wasn't embarrassed. I couldn't understand why I had those odd nutty thoughts. I didn't know why my penis would sometimes be hard when I awoke from those dreams. When I was 11, I saw a boy dressed up as a girl on Halloween. I couldn't believe he did that. Then I noticed that he even had on nylons. I wondered if he'd been punished and then it occurred to me that he wanted to be a girl for Halloween. I realized I was jealous.

Sometime within the next year, I finally tried on one of my mom's skirts. Then I decided I had to try on more of her things to discover that peaceful and exciting feeling that the dreams gave me. One night, I put on her panty girdle, nylons, half slip, and yellow chiffon dress and I realized that I adored the feeling. I walked about the house, I sat down again and again, crossing my legs and I kept feeling my legs and I adored the wonderful feeling of my nylons whooshing against my slip. The swirl of my chiffon skirt felt incredible. When I couldn't stand it any longer, I took off mom's dress and I masturbated. I immediately felt guilty and wondered what kind of pervert I was. I swore I'd never ever put on women's clothes again. I broke that promise the next weekend when mom and dad were out.

I read The Catcher in The Rye when I was fifteen and I was thunderstruck by Holden's description of a transvestite he observed in hotel room window. The man's movements as he dressed himself sounded just like me. It seemed dirty and perverted. I thought, that's me, there are others like me, but I'm not a pervert.

I always assumed once I kissed a girl that my desire to crossdress would vanish. It didn't and then I assumed it would once I lost my virginity: it did not. Then I assumed once I married it would. Then once I was a dad. It's never gone away. I stopped beating myself up over this and have come to accept it. Though, I'm going to guess once I'm dead it'll finally go away or won't matter to anyone.

My wife knows I crossdress, but she prefers to not be part of it and she doesn't want me to be public about it. We have a don't ask, don't tell arrangement.

I'm fascinated by first time stories. I suppose I yearn for soft and gentle introductions to CDing because I think mine was dark and perverted. Perhaps I'd have been a crossdresser without having been a girl in the show. Perhaps Lou grabbing my crotch had nothing to do with anything either. Maybe it was just a joke. Yeah right, I think Lou was a criminal pervert. He and his God Damned day camp should have left me and the other boys alone and had I been an adult at the time, he would have found himself investigated by the Police. I bet he masturbated that evening at the thought of us putting on our dresses for the show and he got away with it.

That's my whole story.

[emily606]

Hi Lisa,

You should read my first time story. I was at a day camp too, but it was not a fun experience. If you don't find it, let me know and I'll send it to you.

[Nadya]

My crossdressing started when I was about 12 years old. I would be home from school "sick" and I was so fascinated by women's clothing. I tried on my mother's pantyhose first and couldn't believe how great they felt. I had to feel what a whole outfit felt like so I tried on a dress too. I loved how it made me feel. I remember wishing I could dress like that all the time. After taking it off I was paranoid that my mother would know what I had done so I sprayed her dress with perfume which probably made her suspicious about what's going on. I did it a lot when I knew I was home alone for a long time. I never was confronted by my mother about it though. I would try all sorts of things I found in my mother's wardrobe and I remember it being so much fun. Getting caught once by my very intolerant brother forced me to suppress it for a while until I started having those same desires to crossdress.

[DQ Tanya]

I dont remember - all I know is I cant remember a time when I didnt....but then i remember very little from early childhood - I must have had a good time huh

[Zoe B]

I can't actually remember the moment itself, but I do remember that it involved formal gloves.

[Desirae]

Somewhere around 4 or 5 for me playing with my mother's heels. During the weekends when I would go over to my father's house, I would put on my sister's nightgown, which was always hanging on the bathroom hook.

[sylviatv]

i started wearing nylons and tights in my early teens.

[Kitty215]

Somewhere around 8-10 years old trying on my mom's panties. Over the years graduated to bras and pantyhose. Always just felt natural.

[Xandra]

Curious: What are formal gloves?
I can't actually remember the moment itself, but I do remember that it involved formal gloves.

[Samanthasmith]

I think I was 7 or 8. The first time I wore my mom's lingerie I was hooked for life!

[janetcgtv]

About 6 or 7, I tried on a girl's babushka under my front porch. Plus when my Mom and I went shopping I couldn't resist looking at the blouses,skirts and dresses when we walked past the Three Sisters Store and also wishing when we were on the 1st floor landing I wanted to have a perm in Goldblatt's Beauty Salon.

My signature says it all.

[Blackopaquetwo]

When I was 5 or 6, I put on my Mums tights and they felt so good. I've been interested ever since. I've always loved the feel tights give you but also got intrigued into how good women's clothes make you feel when fully dressed. I started with just knickers, bra and tights when I was 18 but then moved onto fully dressing when I was twenty odd. In my situation atm it is hard to dress fully so have to stick to knickers bras and tights unless I am 'away'.

[colleen_cd]

I was about 8 years old, and had to wear girls tights as parts of a costume for a children's' ice skating show - I was mickey mouse :) I put them on and wow they felt nice. It was a few years later that I started "borrowing" my mothers hose, slips, bras, etc.

[jillishy]

I was 12. I discovered some wigs in the basement then tried a few dresses, shoes then....bingo! I was hooked. I instantly fell in love with the feeling of being pretty

[Brianna in Hose]

I was in kindergarten when I discovered pantyhose. Mom would comb my brother and my hair and put legs off of her pantyhose on our heads to hold our hair in place when we went to bed. I would then play in the ones that didn't have any legs. One day while playing in my fort in the living room I went to grab the hose I wore but ended up with a full pair instead. From that day on I would barrow moms pantyhose and even wore them to school under my jeans. Then when I was about 8 I started in with full crossdressing. In twenty years I haven't regretted it.

[Skylarlynn40]

I'm not sure of the exact age but I was in the single digits. My first time was seeing my sisters one piece bathing suit hanging up in the bathroom. I really felt the urge to try it on. The fabric felt incredible. I soon progressed to wanting to try on clothes of more types mainly panties and bras. Whenever I was home alone, I would raid my mothers wardrobe and have a great time. I remember there was one black thong and matching bra that was my favorite.

[alice clair]

I was at a family friends house spending the night, they were two sisters and their mom gave us a bath in the tub together. I guess I was about 4 or 5 when we were done I did not have any clean underwear so she gave me a pair of one of the girls to wear, I loved them, they were pretty and had flowers on them. Later when I was in my early teens I remembered the panties and bought myself some and have been wearing panties ever since, of course now I have about 40 of them along with all of my other clothes and don't even own a pair of mens underwear.

[Pantyhoselover1979]

I tried on my mother's sheer knee highs when I was about 5 then since I had them on I went in her closet and put on her shoes she just laughed and said that I wasn't supposed to wear those i didn't try actual pantyhose until I was about 7 at my grandma's house. When I was about 7 or 8 my mom gave me an old pair of her shoes and said dont let your father see these lol

[jenni2313]

I can remember wanted to from a very early age. But the first time I was probably around 8 when I put on my sisters Guess jeans.

[VeronicaWasboyski]

I'm new here, but I couldn't resist answering this thread!

I remember being 10, playing dress-up with my sister and finding an old Halloween costume, some girly pink fairy dress. I put it on just for fun, but when I went to take it off, I caught myself in the mirror and couldn't stop staring. It felt so wrong, but in a way that gave me a crazy rush.

I filed that desire away and didn't think much of it. Then a year or so later, I saw the movie "Ladybugs" on TV. It's about a boy who has to dress like a girl to play on a girls soccer team. In one scene, he has to learn how to act more lady-like, so he's taken to a dress store. He ends up in a white flowery dress with lace trim and a little rose on the front, with a blonde wig with bangs that made him look just like all the girls I had crushes on in middle school. I taped the scene off TV and watched it over and over- I wanted to be him so bad! From then on, I was hooked on dresses- the more flowery the better!

[Brandie.n]

13 tried on a cousins tights,leotard and knee high heeled boots.was going to be a cat for halloween

[Alara]

Nail polish about 5, clothes mmm 8 or so. I still remember pretty vividly putting on nail polish too!

[sexymexs]

I was you very young 6 or 7 so i really had no idea. But its in some of us. I like been a guy but I also like been girly.

[BeccaTVinNH]

I remember being 4 or 5 and trying on my aunt's stockings that were hanging in the bathroom. I always felt she knew what I was up to in there. I have been hooked ever since

[Carolina]

Very early. I must have been like 3 or 4 when my mom asked me to wear my sister's panties since my underwear was all being washed. I must have liked it. The other vague memory is me at about 5 or so wearing a frilly dress from my sister and being caught in it. I don't recall what happened but i was hooked. Ever since then i would wear my sister's skirts in the bathroom and i'd put on pants over them to go to my room. With the benefit of hindsight i believe my parents must have suspected, but said nothing...

[Andrea Payer]

i think i was 5 when i put on some clothes of my mother. the blouse was much too large and i had to use a belt for the skirt :)

[krissy]

I started when i was six i used to put om my sisters panties. at 8 my step dad made me dress in all my sisters clothes and sat me on the front porch so everyone could see me.i was hooked for life

[Eveyorkuk]

I think I wss about 8 when I tried om my Mum's swimming costume. The thing is, I don't know what drove me to want to try it on. It just felt really nice.

[GailNightshade]

I have been wearing womens clothes as far back as a child can remember

[Betty IA]

When I was about 7 or 8 my mom accidentally washed a pair of my tighty whiteys with a red shirt and they came out pink. She put them back in my drawer and said I didn't have to wear them if I didn't want to. I remember frequently wearing them under another pair just because I loved the look of the pink. I learned how to do my own laundry from this, too :)

From there I waited until puberty and began trying on her undies and even some of my sister's when I was able. Now I don't even own any men's undies (except for a few really high priced pairs from Prevail I purchased years ago before realizing panties were the way to go).

[rodiz72]

I was 12 wen I first tried dressing up. Was at my aunts house nd noticed sum lingerie she had nd sum thigh stockings. So I took them hm with me nd later on that night I tried it on n mmmmm fell in love with it.

[darinyc]

Hi there...

I began when I was about 10 years old. I didn't think twice about doing it. My mother was out all day and I did the proverbial closet raid. I was able to fit in everything quite well...a blouse, panties, tights, heels. The big challenge was putting everything right back where it belonged. Quite frankly, I believe she had her suspicions but it was never discussed.

Anyway, for a months after that, I continued. One great resource I had was the laundry room in our apartment building. There always seemed to be some dresses and stockings that were left behind. We had a neighbor who would ask me to cat sit for her while she would go to work, etc. I would have my little stash of clothes in a bag and dress in her apartment and just hang out.

[Ricki Dove]

I have thought about it for a long time, but only got the courage to actually do it after I retired from work.. I just started the first of last month at age 67. I have a lot of catching up to do. I really feel like it will be a great ride!

[Isabella Ross]

Like many others, about seven or eight years old, although I know I wanted to long before that--I used to wait for new department store mail order catalogues with incredible anticipation (Eatons, Sears and Woodwards here in Canada)...I would gaze at the lingerie photos with so much longing and curiousity! Finally, I gathered the courage to explore my mom's dresser, and I vividly remember trying on her Vanity Fair full panties and a slip. I was in heaven...but mortified at the prospect of being caught.

[LstSoul22]

I believe I was 8 or 9 and had always had a curiosity of sorts in the back of my head about the womens garments I would see in the Sunday paper and in misc. movies I maybe shouldn't have been watching at such a young age. Like many, that led to me going through my mothers drawers each and every time they had gone out and left me home alone...this carried through til my late teens when I left for college. I really love the various materials of women's undergarments and the way they feel. Safe to say I too am hooked and get some very strong urges to dress at times.

[Annette_boy]

Hi everyone

I started with Moms panties at age 5 and loved it . When I was 9 she helped me dress as a girl fro Halloween panties slip and petticoat dress shoes the works and I was hooked.
She did not take the things back after and I dressed off and on for years I now live fem 24//7 and just turned 69 . It has been a long and wonderful journey.

Hugs Annette

[tammie]

Rikki Dove Honey Congratulations for you sweetie.

The truth is some men are more manly than others , at age 14 I had breasts and a hot woman whispered in my ear that my tits were bigger than hers and I should wear a brassiere and her lips touched me when she said that word , a week later I saw a black lace bra on the floor of my sisters bedroom , I tried it on and almost feinted from the wonderful sensation , it fit me like I was measured for it
and I have loved wearing a bra ever since .

As we age , men turn into women it seems and women get more masculine . Since I turned into a sissyboi at age 14, I wore my moms stuff next and got caught in her bra girdle stockings and slip
all excited and just about to start mincing in the mirror as I looked quite cute with breasts in sexy lingerie, so

my mother was as confused as I was so she asked her gay friends what she should do to help me , she shopped for me and got me my own lingerie, their advise to keep me from stealing as boys
with a sexual fetish for lingerie will tend to do and....

I have kept growing more female as her friends said I would, and I still adore wearing a bra now a 42C and now I love dressing up for men who like sissies in bras and stockings with slips heels and makeup . Some times I even wear my hair styled for a mans pleasure and a hair comb to look as ****ty and femme as I can for him and wear a blouse and skirt too , might as well wear as much clothing as you can if you are going to get stripped right away to your bra girdle and stockings heels to be a femme sissy for real men . So that is where you are heading honey let me know if you ever get to the state of Az we can play , I buy the drinks .

[NicolaF]

I remember being as young as 5 or 6 when an older girl who used to look after me after school putting lipstick and nail varnish on me and me loving it.

I was probably 14 or 15 when I first started trying on the odd bit of clothing when the opportunity presented itself, and 21 (last year) the first time I ever went full wig, make up, dress and actually passed for a girl.

[TAMMY GIRLS]

I was very very young when I tried cross dressing. I would try using shipping box corner isolators tied together with string. It worked until someone found them and removed them.

[shelly1]

the first time I was in first grade I put on my sisters panties and tights

[raven_crossdresser]

I started later in life than most. I used to wear my wife's lingerie during our first years in college.

[Joy3]

I believe i was about 6 or 7 when I would play with a neighbor girl, Cathie. Her aunt lived next door and we would play at her house. Cathie wanted us to play as girlfriends and would bring some of her clothes for me to wear. I loved being her girlfriend! We would experiment with aunts make up and i felt so pretty. I then started wearing my mothers clothes when I was home alone.

[Della]

Vaguely. In my younger teens with what was available. Panties only, I recall.

[paige_stone]

I started when i was 4 or 5 with my mothers jewelry and then it progressed slowly from there.

[autera24]

first time i wear in 8 years old my mother"s black leather 3" heel pair of boots

[kayla316]

My mom held dress up to me when i wa 5 to check the size for a friends bday gift and I thout it would look nice on me. Didn't get to try it on though. A few years after that found a dress that would fit and tried it on and been hooked ever since.

[Janine cd]

I remember trying on my mom's nightie and shoes when I was 6 or 7. When I was 11, I went the whole way and wore her bra, panties and slip. I also tried on her makeup, powder, lipstick, eyebrow pencil. Unfortunately, by this time, I had otgrown any of her dresses and shoes.

[Sarina Curtis]

When I was around 9 or 10 I remember my mom going on about something or other with her pantyhose. Just to see what the fuss was I tried on a pair of her hose and very clearly remember the cool feeling of the air passing through the weave, the comfortable compression (by 10 I was nearly the same size as my mom) and wondering why Dad wasn't chipping in on the conversation. Back then I never thought it would become as important a part of who I am as it has.

[vicky_cd99_2]

I raided moms lingerie drawer at 8-9 and that was it for me. Until I could no longer fit in moms stuff. I think she knew but never said anything. At age 12 she dressed me as a girl for Halloween. I wish I could find the picture she took of me.

[Bluesman]

I was 15, playing one of the kid roles in a professional production of Macbeth. Dressing room space was limited, so couple of the gay men and me (go figure!) shared space with the female cast with just a clothes rack separating us. One night when I was alone in the dressing area, I noticed a pair of panties on a chair. I pocketed them, took them home, put them on and masturbated. Around that same time I discovered a trunk in the attic with a couple of nightgowns in it and started wearing one to bed. Over the next years I found or purloined panties until I got up the nerve to buy my own along with a matching bra in my early twenties.

[Big Sister]

I recall playing about with my aunt's tights in my room at night, aged abouty 6 or 7. It's just coming back to me now that I also used to drag myself along in high heels, and although they were probably quite small, they seemed huge to me as a young child.
Later on I started wearing my sister's knickers when they were in the washing basket or when I got a chance to sneak into her room. The first pair of my own were stolen, I am sorry to say, from a changing room in a shop. Another pair were stolen from the washing of the house next door where there were four girls living but alas they were too small. I no longer steal these days and get a thrill out of buying my own.
Very much a novice and limited to a few items under my male clothes. Bought a bra and some tights a few days ago which is a new departure. Tights are a drag, if you will pardon the pun - I just put a hole in a brand new pair with my fingernail. Enjoyed buying them though and the young foreign lady at the till was fun and chatty.

[Mistybtm]

My crossdressing started when I was about 12 years old. I would be home from school "sick" and I was so fascinated by women's clothing. I tried on my mother's pantyhose first and couldn't believe how great they felt. I had to feel what a whole outfit felt like so I tried on a dress too. I loved how it made me feel. I remember wishing I could dress like that all the time. After taking it off I was paranoid that my mother would know what I had done so I sprayed her dress with perfume which probably made her suspicious about what's going on. I did it a lot when I knew I was home alone for a long time. I never was confronted by my mother about it though. I would try all sorts of things I found in my mother's wardrobe and I remember it being so much fun. Getting caught once by my very intolerant brother forced me to suppress it for a while until I started having those same desires to crossdress.

I he a very similar story, I did pretty much the same ting as you.

[Joansometimes]

I started to crossdress between the age of 5 to 7.:o

[heather ann martin]

I've always preferred dressing as a girl. I'm just happier in skirts.

[Lacyfem]

I remember exactly when I started as I was 10 and the folks had a cocktail party at house and then went out to dinner. I started sampling the bourbon which I'd never done before and got quite high if not drunk. Not remember totally why but I went into mom's lingerie drawers and put on a nylon panty and bra. Her being a C cup I stuffed the bra with other panties. I felt so good as I walked around the house with a small glass of bourbon feeling what it must be like to be a woman. It was evening and I got brave and went out into the yard and walked around for quite awhile just in her panty and bra and found it quite exciting and to this day still think it's quite exciting as I'm sitting here now typing this in a wonderful bra and panty but this time they are my own.

[Gina Glowe]

I was 6-7 - got out of the bath tub at home and there on the shower rod was a pair of moms stockings- I don't know why , but the next thing I knew, I had them on - I am amazed at how young most of us were and how we have gotten to where we are now -all in different settings and circumstances, but with the same basic understanding of Nd need for ourselves.

[raelene]

I was seven yars old when I put my sisters panties and bras on. She was 17 at the time.

[Lisa760]

When I was 4 or five my mom caught me in my sisters room with her dress on.

[Dava76]

When I was five I had to get a shower at my aunts and had no clean clothes there to put on. So I ended up wearing panties and a nightie of my older cousin and I loved it. The panties were cotton but frilly and the nightie was so soft and comfy, I was in ecstasy.

[Tatiana]

I had no sisters so there were no girlie clothes around except my mums. The catalyst for my crossdressing was my brothers wedding when I was 12. I remember seeing the bridesmaid dresses and that started the urge in me to want the try girls clothes. As none were available I would try to make a skirt from my shirts by wrapping them around my waist. Small beginnings!

[CherylFlint]

Before 1st grade, 3 or 4 years young.

[sabrinaedwards]

As early as I can remember, I had an affinity for female attire. We must be born this way because I do not remember anything that would cause me to be this way. I tried on my mother's clothing at a very young age. As an occasion would arise I donned my aunt's clothing and also my grandmother's all without their knowledge. I have always been a closeted crossdresser. To this day my wife and I have a DADT relationship.

[Nati]

7 years old. Put something fem on. Loved it. Kept it a secret for years. Tried not to think much about it. Next piece, 11 years old, middle school. I was hooked.

[lonewolf]

I was about 8.I have a sister three years older and a sister two years younger.I can remember trying on their underwear and liking it.As a young child I remember mom giving me a pair of my older sisters hand me down pajamas and I loved them !

[Alleyne66]

I was about 7-8, put on a dress at a halloween style party. Quite innocent. Only a few months ago I went full Cd, lingerie and make-up inclusive.

[Auntie]

When I was 5 parents were seperated and Dad had custody. I really missed my mother. I found a slip that she had left behind and it smelled so much like her I put it on and laid down on her bed. I loved how it felt on and I was hooked.

[Savannah_Skye]

I was about five. I remember wanting to be a girl, so I created my own stuff. Eventually I got the real stuff and never looked back!

[Juanita O]

i was 10 when i tryed on a blue skirt that my mom had, i also tryed on her girdle