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...?

[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]

[SIZE="3"]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 ! [/SIZE]

[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!

[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