What is your fondest memory of your early crossdressing?

[Monika G]

I was trying to remember how exciting and fun it was when I began to crossdress as a teenager. I can recall how exciting it was when I first stepped into a "borrowed" pair of panties. The feeling as I pulled them up my legs was indescribable.

Who else remembers wearing stockings or pantyhose for the first time? Do you remember lifting your leg to smooth the wrinkles out and them admiring how good you looked?

How about finding your first bra that actually fit. Do you recall how the band gently hugged your chest. Did you fill the cups with rolled up socks like I did?

Can you describe that feeling when you first put on that skirt? Remember the sensation as you raised it over your hips and then closed the zipper in the back? That feeling of being a girl for at least a little while.

Does anyone have any memories to share with me?

[M-Anne]

i remeber when i first put a thong on. it was a black thing with red tassels on. it felt so amazing.

i dont remeber when i first put a bra on to be honest.

however i do remeber the 1st time i put a pair of stockings on. rolling them up my leg and finally getting them on. then rubing them to feel the smoothness really turned me on at the time. then the feeling when i pulled up a pair of panties. the soft gental rubbing :)

[sherri52]

I remember putting my mothers stockings on for the first time. I took three steps and they fell down. I then picked them up again and tried walking around my parents bed, they were still too long. All I could think of was that in matbe two years I could get them to stay. As I think back I realize at that time I had no clue what a garter belt was.

[jenifer m.]

yes i remember my first pair of pantyhose i stole from my mothers drawer.i put them on and went out into the cool chicago night air and rode my bike for a while the wind blowing up my pant legs was an incredible feeling when i had hose on.i remember really feeling feminine at the time.then when i put on my moms satin slip and how it rubed aganst my nylon coverd legs it almost sent me through the roof,i was totally hooked at that point it was better than taking drugs.i guess it was kinda sorta my little drug hee hee.

[tifftg]

While I had tried on some of my mother's things for a while, my fondest memory was my early teens when my sister went of to college and left so many things behind. Those paster long leg girdles and nylons are still so beautiful a memory to me.

[Aubrey Green]

Not getting caught, especially by my older brother. He was quite the bully and would have enjoyed beating me to a pulp.

[Veronica Lacey]

Wearing multpile layers of panty hose (3 at most) and two pairs of panties was the first main recollection. After that wearing the same with a panty girdle as I did my early morning paper route. This was particularly nice in the winter, of course, as it would be very cold at 5AM and those layers would keep my body warm and my mind happy as I cycled for the hour or so.

Each first step was euphoria in its own way, yes? First slip, first camisole, first blouse, first skirt. Dress, heels (!), bra, water-filled balloons for breasts. When I sneaked a try of one of my (future) wife's old prom dresses (it was a yellow satin with lace and a slip - it felt divine) I was in heaven as I pulled the back zip up part way and snapped the closures to the top of the back of my neck.

There are still a few more firsts out there...maybe a wedding gown/outfit, some knee-high boots with high heels. Other possibilities...?

:daydreaming:

[immike]

I was trying to remember how exciting and fun it was when I began to crossdress as a teenager. I can recall how exciting it was when I first stepped into a "borrowed" pair of panties. The feeling as I pulled them up my legs was indescribable.

Who else remembers wearing stockings or pantyhose for the first time? Do you remember lifting your leg to smooth the wrinkles out and them admiring how good you looked?

How about finding your first bra that actually fit. Do you recall how the band gently hugged your chest. Did you fill the cups with rolled up socks like I did?

Can you describe that feeling when you first put on that skirt? Remember the sensation as you raised it over your hips and then closed the zipper in the back? That feeling of being a girl for at least a little while.

Does anyone have any memories to share with me?
I remember secretly sneaking into mothers closet&borrowing one of her mini-skirts&
one of her white blouses.I borrowed a fresh pkg of pantyhose out of her drawer*put
them on,along with a skirt&blouse&I went into her closet&stepped into a pair of her
white high heels.The feeling was INCREDIBLE and years later,I still sneak into her closet&dress in her good outfits,as well as my own outfits

[Maria Heels]

My fondest memory is first trying on my step-mother's black patent high heel pumps with a platform. Those shoes were my favorite, and I hope to someday find a pair just like it for my colleciton...those shoes excited me, and I was so used to wearing them that they were like a pair of sneakers...comfortable and easy to wear...

[Rachel Morley]

My fondest memory of early crossdressing? ... my first memory was going around my best friend Rebecca's house when I was about 6 or 7 and playing dress up with her. That's a pretty fond memory, but the one that sticks in my mind the most was when I was 16 and my girlfriend at the time (and her younger sister) wanted to dress me up in their clothes "just for fun".

I had fairly long hair in those days (late 1970's) and she put my hair in a pony tail with barrettes on each side of my head. She also dressed me in a blouse and skirt with a padded bra. I was scared to death and excited at the same time in case her parents came to her room :)

[Danielle76]

I've always been a freak for thigh high stockings. I remember finding some of those in my sister's belongings, and the first time I borrowed her black silk slip. That was AMAZING!!! Fond memories, those...

[Imogen_Mann]

I'd be a lier if I said my early memories of dressing included stockings, thongs and stuffed bras... Stockings and bras don't fit 4 year olds, and around here, thongs didn't exist until the 1980's and that was 10 years too late.

My memories are of my sisters knickers and a yellow tartan skirt, her ballet leotard and my mum's undies drawer. There was a suspender belt in there... I had no idea at all what it was, or how it went on... But I knew, deep down, I wanted that too. It remained a mystery until I was at least at puberty. I think my 'happy memory' was clomping around playing dressing up with my sister, I was wearing a long knitted dress (Hey don't laugh.. It was the 70's !!) and a pair of gold ( I did say it was the 70's !! ) high heels.

Happy days marred only by the repeated beatings at the hands of my mother every time she caught me at it. The good part out-weighed the bad... As it was, is and always shall be.

[MargaretJ]

My earliest memory is around aged 4, trying on my mums panty girdle and shoes. I can also remember not wanting to get caught! I can't remember my first experience of stockings/tights, but the feeling of my legs in stockings has always been a strong influence on my desire to crossdress.

[JustAlex]

I have many memories but my oldest is of wearing pillowcases as dresses. I was probably 6 or 7 at that time and I was already messing with mom's panties but somehow the idea of using a pillowcase crossed my mind and it fitted.

After that, my first experience fully dressed was at age 14.

[Michelle-Leigh]

Mine would have to be the first time I fully dressed up (had been wearing just bra, hose and panties before that). Some time before that, I had seen my second cousin wearing a short silky dress and pantyhose, and so I was about to bust wide open to wear what she was wearing. At the first opportunity, I found a very similar dress in Ma's closet, dressed up all the way in it (with the hose of course), and when I first looked at my reflection in the mirror my knees turned to jelly and I nearly collapsed !

[EnglishRose]

I just remember going into my moms room and trying her clothes on, while she was in the room!! That was when I was 6 or 7. I can vaguely remember her laughing good-naturedly at it. She'd probably be less fond if she knew just how many of her undergarments and lipstick I tried in the later years.

[t-girlxsophie]

Without a shadow of a doubt had to be my Aunties Wedding dress,and two Organza and silk bridesmaid dresses,loved them so much I used to take unbelievable risks like sleeping in them etc

[josie_S]

My cousin moved in with us when I was like 15 and she was about 18 and we were the same size (OH HOW I MISS BEING THAT SIZE!). She had great style and I was desperate to try them all on. One night my parents and brothers and my cousin all went away for the weekend and I had to stay back for some reason (work? some school stuff? I don't remember and I sure didn't feel neglected :P) It was the first time I dressed head to toe minus a wig (but my hair was long then) and I spent the whole Saturday dressed. I tried on a dress of hers and painted my nails and put on make up (badly probably) and I was in heaven. That night I borrowed my cousin's one piece and got in the hot tub and just giggled and swooned at the sight of my painted toes above the bubbles of the hot tub.

I washed everything I borrowed and folded it and put it all back where and how I found it (crossdressers get good at this, I think) and I would never do anything like that now. But at 15? In the mid 80s? No internet, etc?

I HAD A BLAST!

[MonicaJean]

this jarred my memory of a really fond time...
I think I was 11, my parents planned on being out REALLY late that night with friends. I was the babysitter for my younger sister. She went to bed, I fully dressed in mom's L'eggs, skirt, blouse, heels, full makeup...eyeliner, mascara, blush, & oh that pink lipstick!!, even some of her perfurme she used earlier in the night. I truly felt beautiful when i stood in the mirror that night.

I can only imagine how bad the makeup job really was looking back now. LOL But I REALLY felt beautiful. It was an amazing feeling to look in that mirror and say "I wish I could be like this every day of my life!" And then of course, feel guilty about it a day or two later. now, I feel no false-guilt. It feels good thinking back on that memory. In fact, it feels GREAT!

Now, I look at the younger generation and just gaze in amazement at those who were willing to transition at a really young age and live their dream rather than bury it like I did.

[SamanthaS]

My fondest memory while being dressed was when I told a female co-worker about Samantha. I showed her some pics of Sammi and as she was going through them, she said" Thats a man!" I looked at her and she looked at me and said "Oh my" After work she asked if Samantha would like to come over to her house for some wine. She informed me that her husband was opened minded and wouldn't care if Sammi came over. At the time I wasn't sure enough in myself to go with the husband there, so I said no, maybe another time when he wasn't there. See called me back in like ten minutes and said her husband would be leaving for work at such and such time and asked if Sammi would come over. Hell yes! I quickly picked out an outfit, black skirt lepoard top with black sling-backs and went to Laura's place. Laura was very open and asked questions I wish my girlfriend asked. We drank wine and looked at clothing catologs when I got this idea in my head to ask to see her closet. I tried on a sinky dress of her's and couldn't get it over my head to take it off. She tried to pull it over my head but it was not coming off. I'm in pantyhose, bra and corset, and we were both like where is someone with a video camera to catch this moment? Well when she got the dress over my head, my wig popped off and went flying across the room, we were in stitches! I will always have a special place in my heart for Laura :)

[Jason+]

My fondest early memory comes from a time when I got sick. I very rarely get more than the sniffles so for me to be down in bed sick was notable. My wife offered a cream lace nightie of hers for me to wear and a pair of ivory pantyhose hoping to make me feel better. Didn't help with being sick much but sure was sweet of her to offer especially with her not being a fan.

[Joanie_Shakti]

Bikini panties from the 1970s. Specifically, J.C. Penney's "Days of the Week" bikini panties. But the bikinis and hip huggers in general had a cut that you don't much see anymore. Nylon fabric with a crotch in the same fabric instead of cotton crotch. And wild, psychedelic prints.

[Miss Anais]

I remember high heels the most! I loved learning to walk with them, slowly at first, and then more and more confidently. I felt so girlish in them, they were so taboo, yet felt so right! I was into "playing dress up" as a younger boy so my mom actually didn't mind me doing this. I was an aspiring actor, too, so my little promenades weren't met with much skepticism. I even have a picture of when I was 9 and posing in one of my first high heels..cute!:o

[NathalieX66]

I was nine years old, and I wanted pierced ears so badly that I took beads from a necklace from my mom's jewelry box, and glued them on my earlobes with Testor's model glue...and also glued some earring catches on the back side of the lobes as well, so it actually look like I had pierced ears. the glue actually gave quite a burning sensation, but I was thrilled.

[DaisyG]

It was about the end of June, 1945. I was then age 6. Shoes were just starting to become available again, after a prolonged wartime shortage.

One of my playmates got lucky when her mom spotted a pair of really cute Mary Janes in a store. My friend had them for maybe a week when she and I had much of an afternoon together. I don't recall whether I asked to try them on, or she decided they would look good on me, but she let me put on her Mary Janes. Those girl shoes looked so, so pretty on me. I felt at the time my feet looked like girl feet! I was sad indeed when time came that I had to give Sonja's shoes back to her.

From that day on, putting on a cute pair of shoes has given a real boost to my femme feeling. They may be low heel, mid heel, or 4-inch - - - I look down at my feet and say to myself "That's ME!"

Daisy

[Jenniferpl]

My mom had longline bra that I would wear every chance I could.

[adrienner99]

I used to pretend to be sick and stay home from school to dress in privacy. My mother had one petticoat which I adored wearing, plus a yellow silk evening gown, black patent high heels, and even gloves. Diamond clip on earrings, too.

With my short black gloves on, I would open her Revlon Cherries in the Snow lipstick. I learned quickly to apply it quite well.

It was heaven.

[Rachel05]

I too remember those early days with great fondness, my mum had some really nice underwear and I used to find it very nice against my skin and I worried so much in them early days about leaving the drawer contents exactly as I found it so she would never know

Yes I used to use rolled up sock to fill the bra's out and my favourite dress of mums was a really nice short white one and by the time I was about 13yo it used to fit me perfectly, I think I used to wear it more than mum did

They were great if not sometimes a little confusing days

[JennaR]

All of those things bring back fond memories. I guess the zipping of the skirt somehow strikes a nerve or the first time I tried on a wig. But I have to say sharing my pictrures to the world through this forum after having to be so carefull that no one ever saw me dressed can't even be measured. Yes, freedom from fear.

[APRIL0401]

I was lucky. During my high school years I had a part time job cleaning classrooms after school for this Catholic grade school.
I found this closet containing girls school uniforms. Girls donated their old uniforms after graduation from eight grade. I was a skinny little kid at the time so the clothes fit perfectly. Many days after I finished work and all the nuns and teachers were gone I would try on a white blouse, the plaid jumper, and the knee socks and walk through the hall ways and go in the eight grade class room and sit in a desk and pretend that I was a school girl. I would do this a few times a week. I would even go outside during the winter months when it got dark early. Those were great days.

[Midnight Skye]

One of my favorites was my first swimsuit. It was white with tiny blue flowers all over it, and it was soft cotten fabric. It was also slightly too small so it hugged me tightly. I can even remember it had crossed straps in the back. I just adored wearing it when I could. :)

[ArleneRaquel]

OMG - You expect me to remember that far back ECK !!!!! :heehee:

[Carol A]

I was 14 and poodle skirts were all the rage, I would wear my moms squaredance skirts with 2 or 3 can cans under it put on a bra and sweather and pretend to be like the girls in school. :daydreaming:

[Pamela Thomas]

I discovered pantyhose and long leg pantygirdles. The silky feeling of the pantyhose was wonderful. Pulling the girdle on and the feeling of it on was so exciting. It was very pretty.

[JustAlex]

I mentioned the pillowcase the other day and now I ran into this

Pillowcase nightie (http://www.howcast.com/videos/341938-Valentines-Nightie-Howto-Threadbanger-Projects)

I'd love to have one.

[Frédérique]

Can you describe that feeling when you first put on that skirt? Remember the sensation as you raised it over your hips and then closed the zipper in the back? That feeling of being a girl for at least a little while. Does anyone have any memories to share with me?

Yeah, my girlfriend (at the time) left some of her clothing at my house one day. Nobody was around (I think my father was weeding a flower bed), so I put on a skirt and just enjoyed wearing it for a while. If I had felt “silly” in some way, I wouldn’t be here now, but, since I was pre-disposed to feminine things, tactile objects, and free thinking, I reveled in my re-birth after this minor transformation. I went onto bigger and better things, always just out of sight, giving free reign to my sensitive urges. It was a joy to feel the “male” melting away, and I wanted to be in this newfound state as much as possible (still do)…:battingeyelashes:

[Sarah Doepner]

I'd been caught by my mother but this was before counseling was commonly available so I was sent to spend my way too much free time during summer vacation with my dad and his new wife. My mother and stepdad figured I needed to be deprived of the opportunity and maybe it would cure me. However, I guess the reason for the summertime visit wasn't shared. I was put up in a basement bedroom with an old wardrobe full of girly things that fit me just right. I'm still in love with that short blue dress.

I came back cured! Yep, I wasn't caught by my parents ever again.

[cindycd]

I was 6 and I wanted to trade clothing to shock everybody and to my surprize, I was the one who loved those red pantie's and that green jumper that we traded. After that I couldn't wait to trade with her at any chance we had. Fortunatly for me our familie's were very close so I could do sleep over's all the time and she would let me wear her pantie's and nightie's all the time. Over the year's she never said no if I asked to wear anything of her's and she even used to help me and pick out stuff for me. Unfortunatly she died accidentally about 15 year's ago, and I still to this day love her dearly for being the most under standing woman who ever walked this planet. I wish all my girl friend's over the year's were like her.

[Avana]

fondest -

probably when i was 5 or 6 and I would lay in bed at night dreaming that I could step into my closet and magically transform into a little girl, with a closet full of dresses.


most exhilarating -

when i was in high school i made a few daring runs into the girls locker room during after-school practice to 'borrow' some bras and skirts :eek:

[ringedjohn]

I have lots of lovely memories. I remember the first time I put on a pair of nylon panties - lovely exciting smoothness. And the first time I pulled on nylon stockings and fastened them to the suspenders of my open-bottom girdle. I remember the thrill of wearing a bra for the first time. And having my ears pierced and wearing drop earrings. And - lots more......

[ArleneRaquel]

Seeing da covered wagons roll by. :battingeyelashes:

[Monika G]

Thank you for sharing your memories with me. I hope I brought back some pleasant memories to you. I enjoyed reading your responses. I am glad I finally started a thread that struck a cord.

[Lynneth Lee]

The first I remember was at about 6. I tried on some of my sisters underware(she was 10). That felt so wonderful, the next time I went to visit mt father & step-mother, that I boldly asked if I could sleep in one of her nighties. She laughed and said they may be too big but, that she had a slip that would fit!(It was satin-WOW!) I thought I had died and gone to heaven! When I slipped it on, there was this feeling of pure joy. They both laughed at me, but I didn't care. I'm afraid Dad didn't like this much and discouraged any more dressing. But my step-mother had lots of satin tap panties and I would sneak a pair to wear to bed every night. Oh, those wonderful days!!!

NANETTE FAYE :love:

[ellenwannabe]

Back about 1971 I got completely dressed with wig and makeup and drove 25 miles to the city and went to the college I was attending and then went to a dept. store and had a hard time when I realized I needed gas and had to speak with the attendent that pumped the gas as my voice is very manly - I had a ball that day and that was my 1st time out by myself enfemme - loved every minute of it and have ever since - Ellen

[Sarah...]

No fond memories for me. Every experience was an exercise in reminding myself that while I knew I was a girl (in those days) everyone else thought I was a boy. Now I have the maturity to say who I am things are much better.

[willowgurl]

Hi My fondest memory was the first time my friend Jonny and I went on a weekend camping trip, and was girl dressed the whole time. I sort of became Jonny's "girlfriend" that weekend. Willow

[Myopedee]

There were several although three stand out. First, was the first time I put on one of my mom's panty girdles. I was then hooked on girdles. Second was wearing one of my mom's suits. Skirt, top, and jacket. I felt so completely dressed and it was my first skirt experience when I figured out you cannot run in one-lol. For those two I was propably 13 or 14 so I was about the same size. Third is when I was over a friends house and she stepped out and I wore her Girbaud denim skirt with FAB deep pockets for about 45 minutes. I was bummed when she returned although I have since bought two on Ebay over the years.

[Christina89]

my fondest memory of CDing is when i first started and how i started.

[ArleneRaquel]

At age 20, I wnt out very late on a number of Fridays ( actually AM Saturday) fully enfemme as Maureen, boy did I have a good time.Sexily, but tastefully dressed.One one ocassion the Cabbie wanted my phone#. :eek: :battingeyelashes:

[Ms. Laura]

I remember when I was about 10, maybe 12, I had already discovered pantyhose. They were wonderful. However, my grandmother was quite a fashion plate and had a variety of designer things, plus she was quite young as grandmothers go. She had a pair of 3" heels, sandals, they were like a red and white bead design and I was just transfixed looking at myself wearing heels and hose. I think this is where I realized that all things feminine were what I was after, not just hosiery for kicks. I wish I had never outgrown her things!

[islandgirl]

Going to visit my best friend ( a guy) who had a sister my age and size. He would sneak a dress or skirt and sweater from her closet and watch me try the outfits on. He would even tell me how cute and pretty he thought I looked...Game over...I was hooked at 8 years old...Half a century later...it's still a "kick" like no other.
Kris :fairy3:

[Jenniferpl]

The more I think about it, the part of when I was young was having alone time to dress up.

[krissy]

when i was ten my mom would leave me and my sister and brother at the movies all day in the summer .well this one time my sister wanted to change clothes with me i told her no but after awhile we went into the womens bathroom and we changed clothes i put on her pink pantyslip her training bra her socks and her pretty pink party dress with bows i felt so beautiful she wanted to go sit and watch the movie i was scared to go down stairs to sit down she kept saying she would tell mom if i didnt so after awhile i went ill never forget the way it felt to walk down those stairs i felt like a queen i felt so pretty i walked down went and sat down and watched the movie right then i remember telling myself this is what i want when i grow up .that i was going to dress like this every day it was so easy back then .any way after awhile she wanted to change back i didnt want to .she started crying and saying she was going to tell mom so i had to change but that was the day i knew this was who i was and wanted in my life .that was before life came along and wives how cant stand me :daydreaming:

[Sweeterica]

I remember sneaking into moms room when she was out, looking in her underwear drawer and going through her stockings, i found a pair of seamed stockings put them on with her garter belt, wow was so nice, its all ive wanted to do since then, dress up everyday, sadly at moment i dont have any seamed stockings,must get some thinking about it, i feel so sexy and feminine in them with my tight black skirt on

[donnatracey]

Remember after school (when the house was empty) about 13-14 going into my parents' bedroom and grabbing a dress out of my mom's closet to try on. Then, carefully going into her top dresser drawer (where she kept her lipstick!) and carefully checking each 1 until I found a dark red one to put on....:daydreaming: I was so afraid she would notice that each lipstick was not where she left it.....:eek:

1 time she did comment that my lips looked a bit "red"....always had a problem with chapped lips so used that excuse and nothing else was said.....:battingeyelashes: Must be why I have a fetish for lipstick to this day.....love wearing it as much as possible ...don't buy as much chapstick anymore...:D

[Jolene]

Must have been around 12 years old that day after school when I found my sister's school clothes on her bed. Wanted to put her things on so much but I had to work myself up to it. Panties, pantyhose, bra, skirt. and blouse. I feel nice even now thinking about it. Was about the same size as her at the time so everything fit me well. That feeling was like nothing I had ever felt before. The bra around me and the feeling of soft panties around my hips. After that I would wear her things when I could and sometimes my mother's things as well. Got caught and after the Talk, that was it till many years later and here I am. :)

[Katie1234]

When I was at my friends house (there were 5 others for a sleepover) his sis and mom went chasing us all around the house and I accidentally(before I CDed) got caught and was put in a strapless dress and full makeup (why they did that I don't know why). I think I was 8

[Nicola2876]

My mum bought a pair of blck stockings by mistake thinking they were tights. I found them and put them in my bedroom drawer. Every night after school I would slip into the stockings and a pair of my mum's heels and walk around the house. Heaven for a 12 year old cder:)

[Ms Deidre]

Bikini panties from the 1970s. Specifically, J.C. Penney's "Days of the Week" bikini panties. But the bikinis and hip huggers in general had a cut that you don't much see anymore. Nylon fabric with a crotch in the same fabric instead of cotton crotch. And wild, psychedelic prints.

Wow does that ever bring back memories Joanie!

I would have to say one of my fondest memories came about 1966, I would have been 12 or 13 when the family was gone and I put on my older sister's undies and minidress and white go-go boots with a wig of my mother and went into the back yard, my first outing? It was dark and no one saw me but the breeze on my nylon covered legs hooked me for life.

[Leelou]

By far my favorite memory was 7th or 8th grade our school had Spirit Week, and one of the days was "Battle of the Sexes" day. Basically, it was crossdressing day. One of my best friends was a cheerleader and she "persuaded" me into wearing her cheerleader outfit for the day.

Needless to say, for a young crossdresser, it was heaven on earth. Some of the boys teased me about how cute I was, and one of my teachers teased me about how comfortable I appeared in the girl clothes. If they only knew--well, maybe they did:o

[VeronicaV]

Lots of playing dressup back then! I was about 10, when I used to do shows in front of my grandmother, with her wig, heals, and silk robe! She always got a kick out of it.
Having babysitters who also had girls around my age, provided other great opportunities to explore through their closets and try on some clothes. I'll never forget the feeling of putting on a pair of pantyhose for the first time...sheer exhilaration.
Some memories are a little more permanent. One day I raided through my mom's stuff, and wore her underwire bra the whole day, among other items naturally. At the end of the day however, I was shocked to see a slight outline of the bra across my chest where the "wire" had been! I still have it, and is a reminder everyday of my CD roots. :)

[ashley82]

When I was little I had a big chest of drawers in my bedroom in addition to my dresser... Well some of the drawers held random and off-season things of my little sister. Swimsuits in the winter, sweaters in the summer, tights, and so on. It was hard to ask for more when you're 12.

[Lainie]

I started visiting a thrift shop, following someone's suggestion on line. Before that I had just the occasional article of clothing, threw away most of what I bought because I guessed wrong on the size. The SA suggested I try some things on, and pulled some things off the rack for me to try. Felt so accepted, it was a delight. Soon afterward in their upstairs dressing room I put on a dress that zipped up the back and fit perfectly! It was so feminine--I was so feminine--that I almost fainted right there. It took my breath away.

[Myopedee]

Wearing a long leg panty girdle for the first time. I loved how it controlled me and girdles have been part of me since. The first one I actually bought was a side zipper long leg panty from JC Penny. The next one I bought at a corset shop with lots of courage and that one was a Promise by Porette. The next one was an open bottom which I realized I could wear under jeans and pants. I need to stop typing.

[VanessaVW]

I remember my grandma dressing me in her slip, panties (too big) and stockings. I really enjoyed it. Guess it occured a few times until mom and dad found out.

[Blake Lively]

Let's see, probably early teens I would search my mom's closet and drawers for bras and stockings. It was, if I remember, just out of pure curiosity that I would wear these things. Than as puberty struck a sexual interest emerged. . Ah those were the carefree days...

[Dragster]

At about 12 or 13, I put on my mother's hook-side open bottom girdle. I can't remember where the motivation came from, maybe I knew I needed its suspenders to hold up her stockings. It was so tight, it took me quite a while to do up all the hooks and eyes, but I remember trembling with excitement, feeling that I was a little "trapped" in it; it would take me quite a while to take it off if she came back unexpectedly. I had no trouble hooking up her stockings, and boy did it feel good to caress my legs in nylon! in the girdle! I didn't know what was happening at the time, just that it felt fantastic, but panic set in when I realised I had a major clean up to do, before anyone discovered my "misdemeanor".

I had many more "adventures" in that girdle and stockings, and, if you'll excuse the pun, I've been hooked on girdles and corsets ever since. I progressed to wearing many of her other clothes; my favourite was one of her ballgowns, black lace over pink satin. I can still remember the feeling of its full length skirt swirling around my stockinged legs, and the sound of the back zip going up nearly sent me into orbit. I was really sad when I grew too big to get the zip past my waist.

Tony

[BRANDYJ]

I'd have to say it was not my earliest memories of my adolescent/teen years, but when the first person I ever told, the woman that became my wife, woke me one morning and said that we needed to go shopping for a new dress for me. This was soon after I had firs told her and after a week or so of her trying to figure it all out and accept it. It was not an easy thing for her. So this particular morning was really her way of saying she is really OK with it and is willing to share the experience with me. RIP Dona..and thank you.

[makin' it real]

Oh gosh! I still vividly remember how fun it was trading clothes with a kindergarten classmate, until mom caught us and SCREECHED! Yikes. That didn't slow me down long, though. It's hard to pick a favorite moment, there were so many that stand out. Like visiting my grandparents and stealing a pair of my aunt's panties. She was only 2 years older than me and wore really sexy clothes.
Or the day there was a picture in the local, backwoods PA newspaper of a running girl in a string bikini. THAT sure made an impression. I started standing on the side of the tub in the bathroom, folding down the band on my underwear until it looked like the triangles she was wearing.
Or, oh my goodness, every new, semi-annual catalog from Sears or JCPenneys, with their pages of women's underthings. I would spend hours looking at the demi bras and imagining how they'd feel on me. MMMMmmmmmmm. Yummylicious!

[marlacd]

My fondest memory really wasn't when I was just starting to dress. It was when my wife brought home a brite pink skirt for a number in her dance troup. When I saw it, I decided to build a outfit around that skirt. I had to buy a white blouse, heels, and new lingerine for it. Even a new wig. As it turned out, it was a good thing that I had decided to get lacy bra and slip, since the blouse I had bought was a bit sheer, and it was rather visable under that. I also decided that if I was to go that far, that I was going to dipose of the hair on my legs, and wear perfume too! And of course I just had to have my makeup as good as I could get it, and fingernail polish to boot.
I made sure that as I pulled myself together that I was going to try to not see the whole picture until I was ready.

When I stepped in front of the full lengh mirror, I was floored!!! After that, I proceded to ruin my makeup, and knew that I was never going to be anything less than a Crossdresser for the rest of my life.

Isn't it funny that accepting yourself isn't very hard when you do it correctly?

[RachelDenise]

It was trying on my mother's Playtex Cross Your Heart bra for the first time. I was about 11 or 12 and her lingerie drawer sang to me like a siren's song. I coulkdn't help myself. And now, I'm soooo glad I took those fateful steps and actions.

[Samantha_Smile]

I still remember the first time vividly.
Twas a saturday, I'd have been 12 or 13.
Mum, dad and my lil bro had gone to town doing the saturday 'big shop' which would mean they would be in Asda for atleast 2 hours before going into town for bits and pieces, from past experience I knew they were always away for 4 hours at the minimum.
I had intended to spend the afternoon completing Sonic the Hedgehog in one sitting, I got KO'd by the first Dr Robotnik and turned off the console.
Bored and alone, I made my way to my parents room and mooched around. I went into my mum's delicates drawers and found a white fully satin bra and matching ruffled french knickers. Curiosity took hold, I returned to my room, took my clothes off and went back to the bra and knickers.
I pulled on the bra and fumbled behind my back for a minute and got the hook and eyes to meet.
I instantly became aroused (not that I knew what to do with myself at that age) and went into a state of panic.
I tried franticly to remove it for what seemed like hours (probably seconds) with visions of everyone coming home and catching me. I got it off, put everything away and ran to my room.
When I looked at the clock, I realised they had only been gone 45 minutes, and then curiosity and some amount of determination took hold.
I returned to the silkies and slid the knickers on first up my hairless (late bloomer) legs and I felt instantly softer.
I grabbed the bra again and fastened it, and went to my room and stuffed the cups with a pair of boxers in each side.
I went back to my parents room to have a look at myself in the full length mirror and I liked what I saw.
From there it just spiralled for another 30 mins.
I pulled out some white suspenders and nude stockings, again stopping to look in the mirror.
Then a little black dress that I never saw my mum wear, it fit me like a dream, and then a pair of black heels (again fit me like a glove (ahhh, youth).
Paying no attention to my face I kept a check on the mirror.
I posed around for about 15 mins, and then took everything off with hours to spare.
I dont think I ever did the saturday 'big shop' again after this day :daydreaming:

And the rest, as they say, is history...

[Jennifer in CO]

my 'wedding' when I was 15

ok...now before you all go off and have a cow it wasn't a real wedding. The summer I turned 15 I spent with my GP's. I also spent about 3 weeks with my aunt (who created Jennifer 5 years earlier). Very long story short, I worked the first few weeks of that summer at the Community Chest my Granddad founded. No pay, but was offered 'payment' of anything I found I liked I could have. So after a couple of weeks there, I had all the clothes for the summer a girl could want...and a wedding dress. So when I went to my aunts to spend a few weeks, I took the dress. My aunt was a beautician (another long story of how Jennifer actually came about) and I'll never forget that Saturday afternoon/night. She had to do the hair of a bride and we 'girls' went with her to the church so she could do the final prep. The week prior, she had done my hair (which usually swished around at mid shoulder-blade) in a style similar to that worn by Farrah Fawcett in the Charlie's Angels TV series a few years later. Well, she wanted pictures of my hairstyle, so once the bridal party left she had a church full of flowers available and I had a wedding dress. So, once everyone was gone, I was put in my dress and with my cousins as 'brides-maids' I had pictures taken. The catch to this was as I was preparing to walk down the isle, my Grand dad appears from a side door wearing a suit. In shock (I really wanted to run but my feet were frozen to the ground) I stood there as he walked up. His words will forever be in my heart and mind..."What...you think I'm going to let my grand-child walk up the isle alone?" As he took my arm and we walked up the isle I saw grandma sitting towards the front. To keep from crying was difficult to say the least. The photographer took the pictures Aunt Jess wanted, then took shots of my cousins and me and also took some of me by myself and with with Grandma and Grand dad. Grandma had one of those pictures on her chest of drawers till the day she died (10 years later). No one ever figured out (as far as I know) that the girl in the picture with Grandma and Grand dad was me, just "someone special" as she would explain the picture. The remainder of that day/evening was wonderful, with Grand dad saying as he and Grandma left that if I came home in a dress that was fine with them, that I was still the same person inside. So I spent the remainder of that summer as Jennifer. It was VERY difficult to go back home and to be "me" when I did as I had by then spent 2+ months living/being a girl. Grand dad said he tried to get mom and dad to let me stay that school year (so I could continue being Jennifer) but they insisted I come home.

THAT is my fondest memory of childhood...

Jennifer

[Soriya]

Hmmm, for me it would have to be the very first time I dressed completely head to to with makeup and all. I was a lot thinner back then and when I saw myself in a full length mirror I could not believe it was me. I stood there starring at myself for probably over an hour.

[KerryLynn]

ahhh pleasent memeories. I remember showing my panties to my first "Girl Friend" We were both like 5 or 6 and i had on a pair of my moms panties **not proud of that** We both had a good laugh and she gave me a pair of hers to remind me of her.

She was also my frist kiss and Her brother and I talked her into eating a piece of cat food with us. Kids are werid again Good times ;)

[annie2]

my memory is of my moms lingerie felt so good! running around the house in heels and stockings

[Toni_Lynn]

It simply has to be that day I bought my first bra and panties -- ones that were mine in my size and didn't belong to anyone else. I locked myself in the bathroom and tried them on and for the the first time in my life saw a girl looking back at me. I had tears in my eyes and wanted to run up to her and hug her and hold her. For the first time in my life I saw the real me.

Nothing ever since then has ever matched that first meeting when I found my self.

Huggles

Toni-Lynn

[joannemarie barker]

i remember putting on my sister leotard over shiny stretch leggings and pretending i was in flashdance :)

[LaraCreaft]

I remember when I was younger, two times when I wore women's clothing. First I wore a dress and no pants, just my regular underwear, then the other time was when I 'stole' a pair of panties from my sister. I enjoyed the feel of them, and wore them even hanging out with my siblings. I think I even wore them outside the house, but I'm not sure. I don't recall if anyone ever found out.

[adrienner99]

My mother had a yellow silk evening dress, knee-length, a pair of black patent pumps with three-inch heels, and Revlon's Cherries in the Snow lipstick (still my favorite shade).

I looked great in that outfit. I finished it off with her clip on dangling earrings and a matching necklace.

[Toni_Lynn]

Bikini panties from the 1970s. Specifically, J.C. Penney's "Days of the Week" bikini panties. But the bikinis and hip huggers in general had a cut that you don't much see anymore. Nylon fabric with a crotch in the same fabric instead of cotton crotch. And wild, psychedelic prints.

Oh I know exactly what you mean. Back in the early 70s the Sears, Montgomery Wards, and Penneys catalogues were my dream books. I sit and pour over them, hoping a dreams. I'd make shopping lists of what I wanted to buy, both in my size then as a teenage girl, but also when I grew up. And those panties you mentioned. I loved that style. They had this kinda weird nylon that felt so good. I had lots of them of the years, and it always was a special treat to wear them under boy clothes to school.

See below for an illustration from the 1972 Spring Summer Penneys catalogue

Huggles

Toni-Lynn

[Nicola2876]

I think my favourite memory is when I wore my mother's dogtooth two piece skirt suit with black sheer tights and high heels. Being dressed head to toe in feminine clothes, full make up and my long hair in a femme style I felt amazing. I think it was the first time I truely accepted myself as a TV in my teens. Great memories as I looked just like a female department store assistant:):):)

[linnea]

The first time that I dressed up with a wig, shoes that fit, make-up, jewelry, and an outfit that fit me well was a stunning moment for me. It happened just after I graduated from college. I was thrilled to look so female and to feel so feminine and pretty. I'll never forget standing in front of a full-length mirror and smiling back at my reflection--and saying, "oh my, oh . . . my!"

[lacie]

My grandmother gave me a pair of pantyhose to sleep in when I went over to spend the night. I had forgotten my pajamas, From that point on I made a point to show up without pajamas every time I came over to stay the night. Soon I was wearing hose under my pants to church on Sundays. I wore socks to hide them. It was a big time rush for me.

[dominique]

My fondest memory was when I dressed fully for the first time. My mum's top, putting rolled up socks in her bra, skirt and tights. Wearing all girlie clothes was amazing and looking at myself in the mirror, I couldn't believe the difference and I was hooked for life.

[Cithmore]

I remember playing dress up with my older sisters they would spend hours dressing me up in their bras, panties, slips and dresses they would put make up and perfume on me and little ribbons in my hair which was always shoulder length and even taking me shopping with them.
My best memory is sleeping with my older sister (I often had nightmares), and she would let me wear her panties and nighty.

[stellatoo]

I used to watch "Hitch hikers guide..." on my own in my parents bedroom and shave my legs (dry :eek: can't recall ever cutting myself though!)
I would borrow my sister's leotard and a wide belt she had, along with some boots and be a super heroine for a while.
Playing with her dolls:D

Leaving family get together's early for a "date"-if only they knew who I was "dating"!!!

I remember how nervous I was when I first opened the back door and just stood there looking out at the world...the 1st step, half a second into the outside, and then getting up the courage to walk to the gate!!!

Doing a charity run in my sisters school uniform and getting mistaken for a girl:daydreaming:

So many good times

Stella