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View Full Version : When was the first time you put on a Dress and realized you could look like a Girl



Robbiegirl
05-14-2018, 10:41 AM
Unfortunately for me when I was about 6 my mother and Aunt had this great idea to fool an old nanny that was coming to visit by having me and my younger sister switch clothes. After being shown the simple skirt and being bribed I agreed. Once down to my underwear my Aunt found a frilly dress she thought I would look cute as a doll in and despite my objections I was dressed in it. After hair barrettes were added and a hair band I was allowed to see myself in ! I couldn't believe how girly I looked ! I was shocked that It was that easy to make me look like a Girl ! My mother, and Aunt kept saying how adorable I looked and that maybe I belonged in dresses. I remember hating how short the dress was and that my sister kept trying to talk my mom into putting me into panties. But I kept checking myself out in the mirror in shock that my sisters dress fit so well and shoes and frilly socks.

Of course my aunt was very late and I had to spend way too much time in the dress so all the ladies got to teach me how to sit and walk and curtsy. My sisters use to love to bring up that story to tease me.

Once i realized I could fit into my sisters dresses I was hooked !

Tracy Irving
05-14-2018, 10:46 AM
Sorry, I could try on every dress ever made and still not look like a girl.

Nikki A.
05-14-2018, 11:07 AM
It depends on your definition of look. I think I blend better as a woman with age, better with make-up, more choosy in my clothing and more con.
Did I ever look good as a younger person (a girl) no not really, but I never thought passing back then. It was about the clothing and the feel.

Teresa
05-14-2018, 11:47 AM
Robbie,
Clothes and dressing had a totally different meaning to me until I came out to my wife in my forties, that was when the fllodgates opened and I wanted it all , my own underwear , attempts at applying makeup a wig from a dubious source and shoes . I've said this countless times but the wig was the turning point , I'm not saying the makeup was that good but when the wig went on the guy disappeared ! There was a woman looking back at me in the mirror. I was lucky enough to be able to take as many photographs as I wished as I was a professional photographers so had a studio and full darkroom facilities . The avatar I started with on the forum was from a selection when it really came together for me for the first time , I just couldn't believe it was me .

CrossKimmy
05-14-2018, 11:51 AM
I remember having a moment like that in my mid 20s. I had bought a cute pair of heels one morning in drab and was excited to wear them with all my outfits. I don't know what I did with my make up that day but it looked so perfect. The hair extensions were set perfectly too. I put on a printed skirt and white tank and pairs it with a light sleeveless cardi.

I looked at myself in the mirror and felt that I could probably pass as a female out in the world. I wanted to share my look so desperately that I signed on to a crossdressing video chat room and actually turned my camera on this time. I got a PM from another CD and we were talking about clothes and how we started, etc. She asked if I had ever ventured out dressed and I told her I hadn't yet. She said "why not?! You look like a real girl!" I thanked her so many times over. It was a confidence booster for sure. She asked to see the full look so I got up and posed and showed her my outfit and my shoes. She asked about my shoes and I told her I had just bought them that morning. She told me "go back to the shop and show the SA the look!"

I was brimming with confidence. I packed a purse and probably walked in and out of the front door like a million times even locking it and getting in my car.

I talked myself out of it and went to check my email to which she said "go and tell me all the details." I still regret that choice. I had looked very pretty that day too.

Tracii G
05-14-2018, 11:52 AM
Its a lot easier for little boys to look like girls I would think.
Skin,hair are softer and quite frankly girls and boy bodies at that age are almost the same minus the boy and girl parts.

Jodie_Lynn
05-14-2018, 11:57 AM
and oddly enough, older men and women tend to be harder to differentiate as well. For most, their bodies get rounder, skin gets softer

Robbiegirl
05-14-2018, 12:18 PM
Its a lot easier for little boys to look like girls I would think.
Skin,hair are softer and quite frankly girls and boy bodies at that age are almost the same minus the boy and girl parts.

Thanks Tracii G thats what I was trying to say. As a boy I thought girls were silly and weak, so when I discovered how easy it was to make me look like a sweet little girl it was a huge shock ! My sister on the other hand seemed empowered by being in boys clothes and getting to treat me like her little sister.

I'm 62 so this is kind of what the dresses looked like that my sisters wore and I was put in.

291758

sometimes_miss
05-14-2018, 02:25 PM
Let's see, that would be when I was 7. Not much changed until I finally reached puberty, at almost 17 (I was about 5'10" then, and still able to wear my sister's clothes, she was six feet tall), and my final growth spurt started.

Taylor186
05-14-2018, 02:36 PM
For me that would be never.

Diane Taylor
05-14-2018, 02:39 PM
The first time I ever put on a dress was back in 1992 when I started coming out and from that point until the present, I've NEVER looked like a girl.

Jaylyn
05-14-2018, 02:52 PM
It was right after I got married that I ever put on a dress myself and looked at me thinking I wish I was a girl. Never have looked good in one though. Mom dressed me as a baby in dresses, I played in her under garments in my early childhood, but until I got married is the time I slipped on one of my wife's old dresses. I don't know if I've ever looked like a real girl in one though.

Stephanie47
05-14-2018, 02:58 PM
I go with TraciiG on this one. As a kid I was always slender and underweight. I had really sun bleached blond hair with green eyes. If I had a mother, aunt, cousin or sister who would have dolled me up, I probably would have been able to pull it off. I did take some pictures of myself when I was in my 30's. I wore a blond wig. I think I would have passed nicely if I was six inches shorter. Maybe I could still pull it off if I emigrated to Sweden and hid among those really tall Nordic women.

Rayleen
05-14-2018, 06:02 PM
When after I got married, I bought my first dress...I was slender and I could look like a girl.

Face was soft, nice brown hair , that's why most of us need a wig now, less hair and discolored.

Rayleen

Victoria_Winters
05-14-2018, 06:43 PM
22.... ish. I got dressed up. Red blouse (still have it!) forms, simple red bra, shoulder length hair wig (still have it too!), lipstick. I logged into a video chat to just bs and I was never made. I kept getting hit on actually. I pulled up my own feed and was like DAMN! I’m good looking!

That was some number of years ago.... wish I stil looked like that

Queen Bridget
05-14-2018, 07:13 PM
Mid teens.

I realised I could feel like a girl. But not look like one.

DIANEF
05-14-2018, 07:24 PM
I was 15 when I tried on my sister's dress, stick insect thin, fresh faced, I liked the look so much I've been doing it ever since. (that was in 1979).

Cherylgyno
05-14-2018, 07:49 PM
When I was 6 year's old I could pass as a girl that was older than me due to my height. Same was true into my early teen's.
A nick name that was given to me because of a song. Big John. At 20 I was 6'6" 245.
No longer could I pass.
I am not comfortable in guys clothes.

kimdl93
05-14-2018, 08:11 PM
I'm still waiting for that moment. Afraid that time, HGH and testosterone have rendered that a highly unlikely eventuality.

MarinaTwelve200
05-14-2018, 08:59 PM
about age 14 in my mothers house dress. I was quite impressed at the fit and the way the skirt part hung. As I had a stuffed bra on too, the look was quite good.

Judy-Somthing
05-14-2018, 09:07 PM
Some people say cross-dressers are born with the CD bug but I remember the day when I was about 5 or 6 when my sister dressed me up in her Ballerina outfit I was hooked.
I put that dam outfit on when ever I could and remember underdressing with tights to school in 1st and 2nd grade.

Beverley Sims
05-14-2018, 10:43 PM
I had been dressed up since the age of three by the next door neighbour's girls but when I was five they dressed me up in a Sunday best dress and I went out with them for the day.

It was then I realised that I really did fit in and looked like a girl.

Others in the party were not aware that I was a boy apart from the girls next door and their parents .

DaisyLawrence
05-15-2018, 01:48 AM
Beverley. Am I reading that right? When you were five your next door neighbours let their daughters put you in a posh dress and then they took you and their own children out for the day? Did your own parents know of this? I've had a lot of neighbours over the years but I can't think of any that would hand over their five year old and say "why not do a bit of cross dressing for the day, he might enjoy it". Please don't take this the wrong way but are you sure some of these early historical events of yours weren't just dreamed or imagined?

rhonda
05-15-2018, 03:05 AM
it sure is strange what a dress can do to a male .it becomes a lifetime experience

dana digs sweaters
05-15-2018, 08:27 AM
Age 7
For Halloween
but I already knew what I liked at that age, as far as wearing my sister's clothes :heehee:

Robbiegirl
05-15-2018, 10:43 AM
Some people say cross-dressers are born with the CD bug but I remember the day when I was about 5 or 6 when my sister dressed me up in her Ballerina outfit I was hooked.
I put that dam outfit on when ever I could and remember underdressing with tights to school in 1st and 2nd grade.

Judy do you recall whose idea it was and whether there was any reluctance on your part ? Did your Mother find out and if so how did she react ? Did you learn any Ballet ?

LOL BTW both my sisters took ballet so loved to put on their Tutus . My best friend and I put on tutus once and got caught by our Nanny ! We were so scared she would tell our mothers but apparently didn't

Devi SM
05-15-2018, 11:01 AM
It's very interesting that sometime ago there was a thread about your first time dressed in a pic. I couldn't find my pic.
Now I have it.
I remember being around 7 or 8 years old, in my class, at an only boys elementary school, they mount a representation with some kind of art that was new in those days, mimes.
So they did a group of kids wearing black but with gender to act waiting in a boothphone.
I was a girl and my mom put on me a wig made with wool.
I remember the feelings, when before going out to the stage the other kids bulling me for being dressed as a "little girl". My country is a very homophobic one, more in 50 years ago, but my feelings we're weird. I feel uncomfortable for being bulled but the view of myself with long "hair" the feeling of the pantyhose, I liked it.
Here's the pic.
You can see another "girl" in the booth.
I can remember the name of all those boys and nobody else of that class, that means for me that that experience was very significative for me.

Nic J
05-15-2018, 01:45 PM
This is just never gonna happen with me. I love the clothes but they won't ever actually make me look female.

CynthiaD
05-15-2018, 04:55 PM
I realized I could look like a girl when I was in 5th grade, but I didn't fully dress until a couple of years later. (I'd been partially dressing since about age 3.)

Jaymees22
05-15-2018, 10:02 PM
Similar experience to Vanessa, a second grade production of Cinderella. I played one of the ugly sisters, Type casting?

Stephanie Julianna
05-15-2018, 10:12 PM
The first time I was allowed to be home alone around age 8. I had been sneaking things on from my Mom and sisters draws for years but the first time I put on a dress with full petticoats. This was around 1957. I have been in love with dressing ever since. 62 years and counting.