Can you remember the first time you put on a dress ? What it looked like, whose dress

[Robbiegirl]

It was and maybe most importantly how you looked and felt wearing it ?

Growing up in the late 50s girls wore dresses almost daily but their party dresses were so fem. Around 7 I tried on my older sisters old party dress

a Very short yellow chiffon dress with puff sleeves . I couldn't believe how I just looked like a girl in it, twirling about ! LOL I was hooked !

[Stephanie47]

I did not have an older sister or female cousins. I was all boy until puberty hit. The only access to female clothing was my mother's clothing. The first dress I tried on was one of her summer dresses. Yes, it was from the 1950's and 1960's. A pretty floral dress with a wide sweeping hem. I was a real skinny kid so I did fit into it for awhile. It had a side zipper. That was the time period in my life of self loathing, self hatred of what I was doing. I outgrew her clothing so raiding her clothes ended. It wasn't until ten year later that I bought a dress to wear when my wife was visiting her family across the country. I pretty much got the same reaction and tossed it before she came back from her trip. Still a lot of self loathing. It wasn't until I gained self acceptance, and, stopped looking for validation from my wife that I started expanding my wardrobe.

[candykowal]

I suppose dressing in my closet Mom shared with me as all her small fitting clothes were stored in my closet.
There were so many of those June Cleaver outfits in there, not one come to mind.
The one dress I could call my own does come to mind as I put up such a tantrum to have one....
...you see, I fell in love with the confirmation dresses the girls wore in my Catholic grade school that I begged Mom to buy me something like that.
So, for all I went thru, in the trials of being a femme teen, she bought me my first dress.
It was a Madonna like, White Lace Ruffles Dress, laid on my bed with white Buster Brown Mary Jane patent leather shoes at the foot of the bed.
Later that week, I also got a hand me down clutch, costume pearl necklace and bracelet, and some hair barrettes.
You forget the ones you wore until you finally wear a dress you can call your very own!:battingeyelashes:

[Kirsty2907]

Think I was about 10
Everyone had gone out, don?t remember why I done it or if I?d been thinking about it for a while, but slipped into my sister school dress.
It was green and rather standard issue type thing..
but that was the start

[Lori Ann Westlake]

Yes, I do remember. It was my mother's dress, in pale blue wool, fairly close fitting with three-quarter sleeves and a zipper up the back. I was already in full women's underwear when I put the dress on. I felt good in a bra, girdle, nylons and panties, with a white full length slip. I guess my mother's shoes fitted me too at the time. I slipped the dress over my head, pulled it down over my hips, and I think I had a little difficulty getting it zipped up behind me, which was not surprising. But once I had it zipped up around me, I felt (naturally enough) that the dress "completed" me. I felt deliciously "enclosed" in the dress, as if I were somehow "locked into" femininity. Though I had no wig, I probably didn't look too bad in the mirror. Anyway it was an exciting experience.

[abby054]

As a preteen, I had access to my church after school and on weekends. Except all day Sundays and on Wednesday evenings, there was rarely anyone there. I walked to school. In those days, as long as I showed up at home by dark, no one cared.

From time to time, the church had rummage sales. They stashed the leftovers in a closet in the basement before sending them to charity in the big city. I raided the leftovers. High fashion they were not. It was mostly old clothes from the 40s and 50s. But it was fun to dress up and I fit many of them.

That is where I found my first dress, an emerald colored midi length number in a WW2 era style made of a heavy satin material. I found stockings and cheap accessories but there were never shoes or under garments. I must have been quite a sight but no one ever saw me.

[kayegirl]

Aged 13, and it was my older sister's dress, home alone I crept into her bedroom. An olive green, with a flared skirt that needed a petticoat. Looked a lot better than it sounds, and with a white cardigan, knee high white socks and some light tan sandals, it was my first time fully dressed as a girl. Also my epiphany, from that day onwards I so wanted to be the girl that I saw in the mirror.

[Christie ann]

My mom was an enthusiastic square dancer. All those big skirts and bigger petticoats. My middle school years were full of scanning the special square dance closet in those few minutes after school before anyone else came home. My parents always asked why the curtains were always closed in the afternoon. As only a 12 year old can say...”oh, are they, I didn’t notice”

[jacques]

hello Robbie,
the first dress I wore was my own and it was probably just a few years ago. Until then I had worn skirts and tops.
luv J

[DanielleCD]

I don't remember the first time but I wear a dress whenever I get dressed now. Beyond the panties, bra and forms... a dress completes the wardrobe for me now.

[sometimes_miss]

I was four; my mom routinely got my sister ready for school, picking out her outfit, fixing her hair, every morning. This took quite a while, so, feeling ignored every day, I went to my sister's room and took one of her dresses and put it on, went up to my mom and sister, and proudly said, 'I'm ready to go to school, too!'. Of course mom would have none of that, and got me changed back to my boy clothes, and we walked my sister to school.
When we came home, mom asked me if I really wanted to wear the dress, but said it in such a manner to imply that my answer should be no, so that's what I said. I hadn't seen myself in the mirror, so I don't know exactly what I looked like.

[Geena75]

1975. My dad had bought the leftovers of a group yard sale to sell at our house. There was a short, dark purple dress (barely covered my rear). Short sleeved with elastic in the ends of the sleeves, thin white lace trim around the chest area, and zipped up the back. I remember rigging up a wire to attach to the zipper so I could get it zipped up all the way. Wore it with an old pair of pantyhose my sister discarded. I remember once the wire came off, and I panicked at how I was going to get out of it. Also remember diving in bed and covering up when I thought my parents had come home. I was at my full height then, but a lot less bulky or muscular than now.

[Bluesman]

I was in my mid-30s before I put on my first dress, despite having worn panties, bras, nightgowns, other lingerie off and on since my early teens. Didn't have any sister's clothes to try on. My first dress was a sleeveless white knit sweater dress that I bought on impulse off the rack during my lunch hour from work. I was living alone at the time and couldn't wait to get home to try it on. And it fit! That in itself was a revelation as I am 6'5" (but slender). It was stretchy and form-fitting and felt very sexy. I didn't have it for very long; I purged when my girlfriend and future wife moved in with me. Still wish I had that dress! 40 years later I have 14 dresses not counting the 6 or 7 that I retired for various reasons (fit, style) over the years. Wearing one of my favorites now, but missing that white sweater dress. No more purging though!

[Alice Torn]

I was around age 13 or 14, my sister's sleeveless courderoy green one. Was on cloud nine, but sure felt guilty after.

[ShelbyDawn]

I don't remember my first, I was probably five or six and was trying on lots of my sister's stuff.

The first one I remember was a formal, one of four my mom left in the garage after my sisters chose the ones they were going to wear and the only one I remember.
I was fifteen, tall and skinny and it fit like a dream, taffeta with a built in petticoat, crinoline or tulle, probably, with sequins all over the bodice.

I don't think I have ever felt as pretty as I did that day. I must have danced around the garage for an hour before I finally tried to take it off, of course the zipper stuck and it took me another twenty minutes to get out of that. I was just lucky no one walked in on me.
I do remember many subsequent trips out to the garage and trying on all of the dresses, but the green one is the one I remember.

[Karren H]

When I was 8 or 9.... the gang of girls on our block made up a game called... Catch a Boy and put a Dress on Him.... and I know I was not the slowest boy on the block but for some strange reason I got caught more than anyone else... Ohh Darn! The dress was an old dark colored, maybe blue, velvet sleeveless dress... and it smelled old like one of the girls grandmothers dress, I am guessing. And it felt amazing on! All the girls ooooed and aaahhed! I felt like a princess and I wish I could thank those girls!!

[DanielleDubois]

I was 10 or 11 and I found a beautiful angora sweater dress along with a corset style full length girdle in a cedar chest in my parent’s basement. I still wonder why those two particular items were saved in a basically empty cedar chest along with some random papers. But a very young Danielle did have some fun with them and the rest as they say is history.

[Jane G]

I can't actually recall the first time.

[MilenaSometimes190]

I was 9 I think, and it was my mom's bra and panties then moved to my sister's wardrobe. Felt weird at the time but I realized it was pretty nice and comfortable.

[Kay J]

I was 10 also it was at a friends house one of his sisters dress a blue dress with sheer sleeves and wore a petticoat and stockings with it. My friend had to try one on also we both hit puberty that day to!

[Teresa]

Robbie,
I do remember at about 9 trying on my sisters full layered petticoat for the first time , it did make my head spin . I still feel we were lucky at that time as we had the full cotton dresses and skirts worn with a full petticoat or nice full slip and then we had the start of mini skirts , I couldn't wait to slip into a mini dress of my sister's .

[Fiona Lindum]

First time that I put on a dress was when I was about 20 and was trying it on in a charity shop.

[MonicaPVD]

The first time I tried on a dress I was 15 or so. It was a small stretchy red number and very short. Until that point, I had stuck to hose and intimates. It was probably the most exciting thing I had done to date. A few weeks later I had a friend over after school. We were playing video games and we started talking about the upcoming Halloween party at school. I brought this up because I was looking for an excuse to dress in front of anybody. I told him that I was going to dress up like a hot girl, he laughed and I said, wanna see? It was scary and such a rush to walk back into my room in a dress and heels and see his reaction. I think that was a defining moment in my life.

[Jillcder]

Sometime around 5th grade I wore a dress for my schools Halloween party that is my earliest memory. One of the most memorable dresses I wore was in my early twenty?s and married my wife had borrowed a dress from her sister for a holiday work party but it was a couple sizes to big for her well the first time I was home alone I put on a pair of my wife?s panties and pantyhose then came the dress it was the early 80s the dress had puffy sleeves and a full skirt just above the knee. What I remember most is that was the first dress I wore as an adult that I could zip up and fit me perfect it was an incredible feeling I will never forget.

[kellyanne]

In my 20s but the first forays into dresses were all too small, then I hit on a 3 part wedding dress and it fit great.

Have a few dresses but am generally a blouse and skirt girl.

[Kirsty2907]

For me, there is something about being zipped in, that is appealing.

I bought a short black bodycon skirt (not knowing what bodycon was) but was disappointed with no zip, so binned it and bought another short black skirt and made sure it had a zip.

[Cass42]

Age 7,was a dark navy sleeveless dress.Mom and I were at an aunt's house visiting and I discovered it on the floor deciding to try it on

[Claire M]

I don't remember my 1st dress but I remember every detail of the first time I fully dressed. I was 13 and had tried on my sisters panties a bras a couple time before. One day I was home alone so I tried on one of her favorite outfits, a green wool skirt with a white sweater top. I added some panty hose and a pair of heels. I remember looking in the mirror and my emotions going everywhere .. I felt really good wearing them, I definitely didn't want to take them off ... ever ... but I also didn't want anyone to ever find out I had done it. (a cycle I seem to repeat even to this day sadly)

[Lacyfem]

I definitely remember the first time I put on a pantie and bra as I was 10, so I'm guessing the dress came in my teens as my start was more into the lingerie.

[Beverley Sims]

Ilooked like a boy in a dress, I was five.

[Deborah G]

I'm sure it was one of my sister's wool skirts, along with a fuzzy, cropped sweater top. I tried it on after putting on her panties and bra, and It fit me perfectly. But, I of course needed to stuff the bra a bit to get the right look! I was 14 or 15 at the time.

[Christina89]

I was about 18 or 19. I was staying at my dad's for the summer. At my dad's my aunt also lived there too to help take care of my grandparents that lived there. Well I had the basement to myself and my aunt left some of her clothes that wouldn't fit in her closet down in the basement. I went thru them one night and found her old wedding dress. Her and I were about the same size so I figured why not. I tried it on and it felt amazing. Sadly I didn't get any pictures of it at the time. But I have the memories.

[Robbiegirl]

Lots of Great answers ! Thanks ! I am a bit surprised no one mentioned ever trying on Tennis Dresses ! As got older my sisters had some very cute, white short tennis dresses that came with bikini panties with a few rows of ruffles ! So fun to put on and pretend to play tennis in. Did anyone else ever try one on ?

[Kirsty2907]

Robbiegirl
There is a line......
And you have crossed it 😮

Only kidding😂
No but I did used to fancy Chris Evert and Jennifer Capriari

[Pumped]

I don't remember trying on a dress until about 8 years ago. I bought a scuba fabric, with blue and white strips, flared skirt, sleeveless tank style. I love the feeling of tight clothes and this one fit snug.

What did I look like? Like an old guy in a dress with fake boobs! It was a bit disheartening!

[CynthiaD]

I was in 7th grade when I dressed fully for the first time, dress, bra stuffed with socks, full slip, and panties, all borrowed from my mother. No wig and no makeup, so the effect was a little disappointing. I'd been partially dressing for many years before that, but this was the first time I dressed fully.

[Cheryl T]

It was Mom's.
I have no idea how it looked on me, how I looked in it. All I remember is how wonderful it felt to wear a dress. Of course I had her lingerie on beneath it so that was wonderful too.

[Robbiegirl]

Robbiegirl
There is a line......
And you have crossed it ��

Only kidding��
No but I did used to fancy Chris Evert and Jennifer Capriari

Here is the great Chris Evert in her cute dress and ruffled undies

319757

[Rachel05]

My first time in a dress was one of my mums, it was one of her favourites and she looked really nice in it, it was white with zipper up the back (that was a challenge first time), short cap sleeves and some lace round the neck, it felt amazing, I guess I was about 12yo by then, I had been wearing panties and bra's, plus I used to wear one of my mums nighties, but wow a dress, that felt like a step up and it was

That was where my love affair with dresses began I guess and I still get that wow feeling when I wear one now, some 50 years later

[Rosemary+]

The first time I wore a dress, is a memory I?ll never loose it was the most wonderful feeling.
I was about 4 years old and I hadn?t started school. I was playing in my grandmothers bedroom and I saw this beautiful yellow dress �� hanging in her wardrobe. For some unknown reason I just had to try that dress on. When I slipped it on, I felt amazing, it felt right, it felt like I should always wear dresses. After that first time, when my family visited Nan?s I would make a bee line for her wardrobe and and try on one of her dresses. Eventually my parents worked out what I was doing, I can vaguely remember my father explaining to me why boys don?t wear dresses.
What amazes me to this day is, My memory of wearing that yellow dress is so much clearer in my mind than the talking to from my father

[Lana Mae]

My first dress was put on just a few years ago! It was a claret knit below the knee! Somewhat frumpish! BUT, the freedom and joy it brought is beyond words! Hugs Lana Mae

[Krisi]

I did not know this until a few years ago, but when I was a baby, my mother would dress me up as a girl and pretend I was one. She really wanted a baby girl and this was long before anyone knew the sex of a child before it was born.

She ended up with three boys and no girls so she would sew dresses for her nieces. She would make me try them on so she could see how the fit and mark the hem. I remember protesting, but in hindsight, I might have enjoyed it. This was before I was five years old.

[BrendaPDX]

I have posted this before, in fact I went back and found it. LOL Here I go again... Early high school, I was at the Salvation Army thrift store, I ran across a dress and just had to have it! I paid for with shaking hands, and tried it on that night. Of course it had to fit perfectly! I remember the side zipper, I had never seen one before, but when I sipped it it pulled the dress around me and fit perfectly! I was stunned at the pretty girl in the mirror looking back at me. A girl like "that" would never date a boy like me. I must have stood there an hour... The die was cast!!!

[Rayleen]

first time was my wifes hot pants in the 70s. its started me do buy my own.

[RainbowDash]

Well let's see.... the very first time I wore a dress, it was actually a cosplay outfit of Princess Peach, so I don't think it was a real dress. I knew I was a guy and that I shouldn't be doing these things, but I just couldn't help myself. I felt really girly and feminine, and just felt like a princess in general. As I wore it more often, I started to wish I could actually be a princess, and then wondered what my life would be like if I were Princess Peach. Those feelings have not gone away even today, although I'm not really interested in being a princess that much anymore, preferring to wear other women's clothes.
The first time I put on a real dress, it was from an online crossdresser store. It felt good to wear something that a woman would wear and not just cosplay. There was one problem.... I had no set of breast forms. So when I looked in the mirror while wearing my first dress, I saw a flat-chested woman looking back at me. I liked the look very much and was happy, but I had to have the breast forms so I could have the appearance of a woman with breasts. Well, when I got my breast forms and put the dress on a second time, it was a hundred times better, and I loved the dress even more than before.

[sherlynn]

I don't remember the exact age but it was my pre-teen years. My mom was a seamstress and quite often she would make dresses for my cousin who was about my age. My mom didn't have a dress form so she would make me wear the dress while she worked on hemming the dress or taking in the waist and what nots. It wasn't always pleasant as I would get stabbed by those pesky dressmaker pins quite often.

[Robbiegirl]

I don't remember the exact age but it was my pre-teen years. My mom was a seamstress and quite often she would make dresses for my cousin who was about my age. My mom didn't have a dress form so she would make me wear the dress while she worked on hemming the dress or taking in the waist and what nots. It wasn't always pleasant as I would get stabbed by those pesky dressmaker pins quite often.

Did you ever see your cousin in one of the Party dresses your mom made her ? I would think that would be a bit ackward but funny ?

[ellbee]

I honestly have no idea. :o


But one that sticks out to me?

I must have been around 16. Not to brag, but I had a very hot & fit GF at the time. :D

Christmas was coming up. She was a girly-girl, with a slight tomboy touch. And she was *very* much into fashion & all that. She also enjoyed shopping at those "hot-GG" clothing stores at the mall.


Anyway, we went into one of her favorites, so she could pick out one of her gifts. Don't even remember the name, as they're always changing all the time & it was a long time ago.

OMG, was I in heaven! :c9:

Completely surrounded by all these young, hot GG's shopping for all these hot-GG clothes, with girly music playing throughout the store. I was also the only guy in there, ha!


She picked out some things, then modeled them for me. I wasn't *totally* in the dressing room area when she did, but I was probably a bit too far in? :strugglin Hey, she did coax me to come closer, after all. And luckily, none of the other GG's seemed to mind... Being a young pretty-boy definitely had some benefits, LOL.


So, she settled upon a tight & slinky long-sleeve low-cut mini-dress in a gorgeous black stretch velvet. And she looked absolutely amazing in it!

I paid for it, she grabbed the (girly) bag, and out we went.


Of course, the only issue? It wasn't quite Christmas just yet. So, I told she would have to wait for her gift -- and I would hold onto the dress in the meantime. :devil:


Suffice it to say? I wore that thing a *lot*! :heehee:

Not exactly proud of that, honestly. But, I was a young & horny CD'er. Besides, technically it wasn't hers just yet... So, I forgive myself.


Sadly, Christmas came all too quickly, and I finally had to cough up the goods. :(

Fortunately, she looked way better in it than me! :battingeyelashes:


She wore it for a few occasions. I remember one time, she *really* got all dolled-up with the hair & make-up & heels & what-not. When she was ready, she came down the stairs... OMG, the bright-red face of her father! :roflmao:

Of course, little did they all know, that I had worn that dress first. :p

[Georgina]

I tried on my first dress in my early teens. For the first 5 or so years of my interest I just wore lingerie. Back then my drive was mainly visual. I adored the way slips looked while wearing and I really did not wish to cover them up. Eventually I took the plunge when my mother's dresses fitted better. I was hooked immediately even though the dress was not a perfect fit.. Years later, in the 90s, my mother got a new dress that was a perfect fit and felt so lovely to wear. The joy and excitement that that dress generated was immense. I wore it to death and much more than my mother did. I still have that dress today, a little the worse for wear, but the memories it helps relive are magic.

[Janet Devon]

My first outfit was a jumper but looked a lot like a dress. I was about 12 or 13 and my mom and sister helped me dress and walk and look like a girl for a contest. I won first place and had several guys looking at me like they seriously wanted some of that. It was written in the paper that I had to turn down dates but that was not true. My first dress was a blue formal bridesmaid's dress that my wife wore at her girlfriend's wedding. I was probably about 20 at the time. I still have that dress but I have outgrown it. I don't have the same wife either, out gown her as well.

- - - Updated - - -

Geena,
I was going to say that I can't see fitting that many dresses in my closet but then I started counting. I have maybe 10 or 11. I have a lot of blouses and a few skirts. For some reason, I am attached to one black skirt that fits perfectly and goes with almost any blouse.

[occdresser]

I was 12 or 13 and I didn?t have a Halloween costume so my sister said try on this dress, well I loved it but said I can?t wear that, greatest feeling ever, so I always checked her closet after that for more dresses

[BLUE ORCHID]

Hi Robbie :hugs:, That was OH so many years ago , I am sure that it was an awesome feeling,

>>>>Orchid**0:daydreaming:0**

[susan2010]

I was older than most. I started very young with petticoats and slips, but didn't try a dress until I was about 30. When my wife (at the time) was away I tried her bra and a navy dress. Now I wear dresses about the house quite a bit, and love them.

[UsuallyRick]

First time was very young (like 6?) my parents friends were over with their daughters.. we got into my older sisters dressup chest, they dolled up then went to town on me, like 3 princesses!! The parents had to check on us because we were being too quiet.. oops.. then before we got married my then girlfriend and I went to a Halloween party with her dad and stepmom,(they both were part people) we both dolled up as hookers and said we were lesbian hookers.. took til the end of the party before anyone realized I was a male😁🤣, the hostess loved it and said I would have won the first place had they known.. can't get enough dress wearing in my life now, but still only come fully out of the closet at Halloween.. wish my wife was more ok about it.. her ,our younger daughter ( 19) and I have fun checking out cute girly stuff and I say I would totally wear that..ha ha maybe she's more ok with it than I know??

[SometimesNatalie]

I was maybe 13 years old, and found this dress in my mom's closet...a tight sleeveless thing with a high collar, that hit right at the knee. It was black and white, that's all I remember about how it looked. But I put on a pair of black tights and that dress, and a pair of her black pumps and...wow. It felt amazing, so completely different than jeans and tee shirts or whatever else I usually wore at the time. The feeling of the tights, the hug of the dress...it's strange to say but it felt comfortable. Of course I grew fast and it wasn't long before I couldn't get it zipped anymore and she eventually got rid of it anyway. To this day I have no idea how she ever fit into it, either, hah.

[Sallee]

Not sure it was the first but my guess is around 12 would sneak into the dirty cloths basket and try mother's dress on. If they were gone for a while would head to the closet and try those on. Kept it up for awhile and finally realized I had to stop so I moved away from New England to Colo because I am sure being a mtn man would cure me. After a few years settled in Denver and could buy my own dresses Frequented all the thrift stores in that city.

[Judy-Somthing]

At about 8, I remember the first outfit i wore because my sister took a photo.

Been hooked ever since.

[sherlynn]

As a matter of fact I have seen my cousin in a dress my mom made. It wasn't awkward since she didn't know but it did get a chuckle out of me knowing that I had worn her dress before she ever did.


Did you ever see your cousin in one of the Party dresses your mom made her ? I would think that would be a bit ackward but funny ?

[samuktv]

My first time was amazing :) I only ever wear dresses now x

[Teresa]

Robbie,
I've just read your comment on wearing a tennis dress , I played tennis at school and then later joined a tennis club , I haven't played in years but I'm considering taking it up again as I've found someone who runs a group for more mature players . So I've been checking out tennis dresses , can't find any with frilly panties most now come with shorts .

[Robbiegirl]

Robbie,
I've just read your comment on wearing a tennis dress , I played tennis at school and then later joined a tennis club , I haven't played in years but I'm considering taking it up again as I've found someone who runs a group for more mature players . So I've been checking out tennis dresses , can't find any with frilly panties most now come with shorts .

Teresa you need to be a fashion starter and bring back the frilly tennis panty ! LOL

[SaraLin]

The first dress I can specifically remember, though it might not have been the very first...


I was about four or five. The dress was my grandmother's. It was a plain, rather frumpy, cotton house dress. I don't remember the pattern or the color, but probably a drab green or blue. It was a thousand sizes too big for me - like wearing a tent. My grandmother had to put a belt around my waist and hike up a lot of the skirt material under it to keep me from tripping over it - giving it sort of a double-layered skirt effect.

She would do this if I slept over at her house, since she didn't have PJ's for me.
I must have looked ridiculous.

But I was in heaven. For even a few brief moments I was allowed to "be" a girl.

I have a couple thoughts about these times.
I don't think that this "started" anything. I already knew I was supposed to have been girl.
I also remember being embarrassed by it. Even back that young, I'd learned that "boys don't wear dresses" and despite what I felt, I knew that I'd been born as a boy.
I guess my journey of self-doubt and shame started very early.

[jazmine]

I'm pretty sure I was in second grade. It was my Mom's dress when she was a little girl when she first received the sacrament of holy communion. It was really frilly and "poofy". Lol! I remember always being mesmerized by it. My childhood home was a bungalow and I had the entire upstairs as a bedroom. One whole side of the hallway upstairs next to the staircase was closets for the entire family. So I pretty much had access to everybody's clothing. Why my mom still had the dress I do not know. One day, for whatever reason, I just decided to try it on. That's the day I found out what heaven is. She also had her eight grade graduation dress in the closet, which was a light pink & equally as cool. When I grew into it, I also would wear it. Why she kept these relics, I do not know, but it changed my life. I love my family. Cool peeps! I got a little something cool from everyone. My dad being a craftsman, loving old cars which led to my love for old Mopars. My uncle being into music and playing guitar, which led to my career. My mom was super cool. Taught me how to be a good human, be me, and chase my dreams. I got "womanhood" from her. ....at least as close as I could get to it.......:)

[Kiwi Primrose]

I was still at high school and was at my girl friend's house when she was dressmaking. It was a dress for herself and she asked me to try it on so she could measure it and mark the hem lines.
Of course I agreed and and she realised I enjoyed it We have been married for over 60 years and she has always helped with my wardrobe.

[MilenaSometimes190]

High school and trying som eof my mom's dresses. Then yearls later bought my own.

[Diedre]

For extra family income my mother did sewing and alterations. At around 12-13 years old I was drafted to be the dress dummy. I got to wear a lot of fun dresses and skirts in my size. Unfortunately I showed a little too much interest in wearing the clothes and was soon replaced with a dress form from a second hand store. My bubble was temporarily popped.

[Bea_]

I never considered my mom's or sister's clothes as anything to be desired. They never had a style that seemed attractive. Very plain.

Moving on to my marriage, it was a couple of decades before I ever felt an inclination to try any of her things on. When I did try on a couple of her cuter items, it just didn't do much for me. Even though i did try on various items out of curiosity, I would never define myself as a crossdresser at that time. To answer the specific question from the OP, to the best of my memory, i tried on a white dress that my wife had only worn once or twice. It was not fitted at all. I didn't hate it on me, but, at that time, it didn't bring any real desire out. It was only curiosity that was totally satisfied and not repeated for years.

After some major trauma over several years in my fifties, I developed a very clear inclination to want to wear things I'd never even considered as an option or even desirable up until then. When I began experimenting, I found a sense of 'rightness' and a sense of strength that still seems unfathomable. Now, half of my wardrobe is from the woman's department and, since I've retired, well over half of my time at home is spent in things from the femme part of my closet.

[StaceyJane]

It's been so long I don't even remember how old I was. It was one of my mom's dresses I tried on and the feeling of of wearing a dress was so wonderful.

[Jazzy Jaz]

I don?t remember which was the first dress as I took several dresses from my sister but they were all lovely and made me feel amazing. I started dressing when I was 11 and the first item I wore was a pair of hot pink panties, from there I quickly ended up having bras, panties, stockings, garter belt, skirts, dresses, swim wear, lipstick, heels, a wig, and purses.

[AndieB]

Honestly, I have no idea what age it was. I'm guessing it could have been around 4 or 5 years old. I remember my parents catching me wearing one of my mom's black lace nighties in a back den. It was super cute and probably felt like a lace dress of some sort since I was still small. I remember my dad saying "we caught a princess" and after that I know I got into my mom's stuff more often. Once I was big enough I started trying on her skirts and dresses, especially in middle school. I would get off the bus while my parents were at work and went straight to my mom's things where I would put on some nylons, a cute slip, a blouse or a sweater, and one of her many skirts. I can't imagine she didn't know because her pantyhose must have been stretched out. Unfortunately I wasted many years in college not dressing as much, but once I hit 25 or so it started again. Ever since then if you had to make a graph of my time versus en femme desires it would look similar to the Nasdaq for the past 10 years -- straight up and no sign of stopping, at least I hope...

[DanielleCD]

I don't remember the first time in a dress. When I first started dressing, around 14 years old, it was about lingerie. Panties and bras and stockings. Stayed that way for many years but somewhere along the line I started with skirts and graduated to dresses and heels. Now I'm not complete unless it's it's the full outfit... Have a new dress and underwear to try out today.. with new matching heels. If I get brave enough I'll post some pics in the gallery forum.

[Christinne87]

When my roommate was out for a few days for christmas, I tried on her blue robe dress, and one of her sport bras (which I stuffed with some socks). She was a bit on the thick side, so the dress and bra fit me great. It felt ...amazing! Never before had I done something like this and I was hooked. I was 28.

At this time, I remember that an older roommate had moved out and some heels had been left behind in the basement, so I tried them on also. They were like 1.5 sizes too small, but I forced them on my feet, and, though each step hurt, it was euphoric. Shaved the legs, and the feeling of the dress and the look of the heels was like a totally different person.

I had been questioning myself at the time, so this definitely helped me discover more of me. Still don't do it very often, but this was the time I found Christinne.

[WasiaCD]

I was 8. We, my aunt and a cousin (boy), were traveling to a resort.
Mom bought a piece for another of my cousins (girl) who stayed at home. By some reason I decided that this was a nightgown bought for me and demanded to try it. Mom eventually gave up and allowed me to model that nightgown(?) in front of everybody. After a few minutes, I remember, I proclaimed "it is very comfortable". But since it was a "nightgown" at it was still a daytime, I was quickly changed to regular clothes and I never saw that nightgown again and this event was never mentioned in the family. Years later, the cousin(m) who definitely was present at the time could not remember that it ever happened.
I think, for me it was also kind of unmemorable experience. Since my second real dress come many years later (in late teens), stolen from mom's closet and I understood what I was doing.

[charlotte72]

Good question hmm, first dress was from a bundle of old clothes my mother left in the cupboard. First was a jean skirt but dress was blue and huge on me .

What an impact.

- - - Updated - - -

i think any age is the right age, never regret what we missed but what we do now is so important.

[darla_g]

i think i was 12 or 13 in middle school . I was home alone so i put on one of my mom's dresses but a full body shaper first. All remembering the exact way these things were situated in the drawers or closet. My mom had a wig in a wig case so of course i put that on as well. and i remember having one of those huge 50 eye shadow assortments as well. It was quite a feeling and escalated too quickly to no good.

[Larissa Cassandra]

Even though I had an interest in girly things from a very early age, I didn't have a chance to try anything at all since there were no females in my home during the last half of my childhood. Much later, when the pink fog started rolling in very heavily, I tried on a few of my wife's dresses, but they were too tight and it was very frustrating! But I did wear one of her larger nighties (given to her as a gift) before I even came out to her. I told her that I loved the feel of hers, and she said why don't you wear this other one? I was shocked but very excited, so of course I initially said oh no I don't do that kind of thing. Well, it wasn't long before she "convinced" me (I had to put on some kind of fight to protect my manly image at the time), and I totally enjoyed slipping it on and savoring the satiny feeling of it on my skin. I slept in it that night, and hoped she would make the same offer in the future. She did a few times, but it wasn't until several years later that I bought my first dress in my size. My wife was out of town, so I remember putting it on and it feeling and looking so good! I tried my best to give my long-ish hair some style, and I put on some of her makeup. It was the first time I ever saw myself in an almost-complete feminine look, and I loved it!
~Larissa

[Sara1950]

I think I was 9or10 my cousin put me in one of her dresses but what I liked most was the panties and stockings she put me into first

[Robbiegirl]

Wow Sara ! She put you in panties and stockings also ! LOL Thank god your mom or Aunt never caught you all dolled up ! Great first dress experience !

[Lori Anne]

Oh dear Lord; that was along time ago. I "borrowed" clothes from my sister, and it was the 70s. I think it was actually a knee length denim wrap skirt and a blouse, and I absolutely loved it.....now, THERE'S a surprise LOL!