Trying on my Sister's Dresses at 7 and looking like a Girl ! Ugh Scary and Fun

When you were young Did it shock you how easy it was to fit into your sisters frilly dresses and how Girly it made you look and feel ?

At an age when most boys thought girls had cuties, seeing yourself in Silly Girls clothes looking like a Girl was shocking ! At least at a young age I realized Girls and boys weren't that different and how easily we could be made to look just like Girls. Scary but also so much fun !

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Maybe its just me. I was extremely lucky to be born 1 year after my older sister and 2 years before my next of 4 sisters. I was also a very late grower entering high school at a height of 4:10. Anyway by the time I started getting interested in my sisters things at around 7 I had so many fun things to try on. My sisters did ballet for many years so the number of tutus around was great. They also later did tennis for years and back in the 60s all the girls wore very fem tennis dresses with lacy butt panties. It was so much fun putting on all these outfits because of how well they fit and felt, but it was also very funny !!! Even with my longer hair I was laughing at myself everytime I went in front of the mirror wondering what would happen if I got caught ! They also had several FRU FRU Babydoll nighties that were to die for ! New Dresses and Slips were constantly arriving. Anyway It was just so Fun and really Funny ! I would pay a fortune now to just get to spend a day at a vintage shop trying on Dresses and those great full slips and getting a good giggle !

I, too, was seven when it happened. It wasn't my sister's clothes, it was someone else's sister's. And I was mortified when I looked in the mirror, and saw what appeared to be a little girl looking back at me. Back then, the worst thing a little boy could ever be, was anything like a girl. That sentiment is still active, as many males AND females continue to use female terms and adjectives towards men as insults to us. We all know the words I'm referring to.

I also had a sister she was 18 months older (and other just 1 year younger) and the older sister loved cloths. Which made my life heaven, at around 9 years old I would fake being sick and spend the hold day in her room. I did feel bad however, as much as I tried to be careful and replace everything just like I found it I didn't. My poor little sister would catch he rafted for being in her room.

Wow, sounds like my story. Being a middle child with an older and younger sister, i had my pick of cute dresses and outfits growing up.

The first time i tried on one of my older sister's skirt and top set, i couldn't believe how much i looked like a girl. Kind of scary and wonderful at the same time. I was in 7th or 8th grade at the time. Its also when i discovered that i wasnt quite like other boys...

Bree

Wow. Where was I? I was born in the same situation, one older, two younger, but didn't crossdress then. What an opportunity missed!

Thank you Sometimes Miss - MORTIFIED is the word I was looking for !

Looking like a Girl and then kind of feeling like I needed to dance while in the dress were very scary! Of course being caught in the dress would have been the worst !!!

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In my teenage years I would try on my older sister's clothes. I was mortified by my presentation in the mirror, it looked neither feminine or me, so I avoided mirrors. But I loved making a feminine shadow, or the reflection in a dimly lit window on a dark night since it would blur out my maleness. The idea of being caught was only scary with no fun side. Probably because I was scared of admitting this side of myself. It was just a guilty pleasure that I should stop doing (and yet kept doing).

Robbiegirl,
Yes, I wore my sisters clothes - a lot!
I am a lifelong CDr and began dressing at around age 6. I am the youngest of 3 with 2 older sisters that were 6 and 7 years older than me. My father travelled a lot on business and was away from home for days and even weeks at a time so it was just me, my mom and my sisters. When I was about 8 my mom went back to work full time. My mom always considered me a very 'grown up' little boy and felt I could take care of myself at home after school until my older sisters, and eventually she, got home. So from the time I was about 8 (c 1965) until well into my early teens I had plenty of afterschool 'home alone' time (this would be anywhere from 3-6 hours depending on when I got home and when my sisters did as they were very involved in aftershool activities). And for a young CDr our home was a paradise! My mother was a total pack rat (probably from growing up dirt poor herself) and kept almost all of my sisters old clothes from when they were younger. So I was home alone in a house filled with tons of perfectly fitting girls clothes. My father even had built a huge walk-in closet in our basement for my mother and sisters to keep there clothes in! My sisters had so much stuff - dresses, skirts, blouses, jumpers, even their old shoes! I wore their panties, tights, vests and training bras, and pantyhose. I wore almost everything of theirs that I could and by age 9 or 10 I was one of the best dressed little CDrs you could ever meet. And this was the 1960s and early 1970s and girls clothes were GIRLY. One of my sisters even had some wigs (she obviously was experimenting with her own looks) and they were just the icing on the cake for this little CDr. There were even ballet outfits and a skating dress (even though to my knowledge neither of my sisters skated). I dressed almost daily from age 9 to about age 14 in perfectly fitting and age correct little girls and pre-teen girls clothes! Complete outfits head-to-toe, shoes-to-wig, inside-out! ! I am sure this is the reason for my preference for girls clothes, as opposed to womens clothes, today (I can and do dress my age but prefer the younger look). Eventually my sisters grew older and moved out and eventually most of the clothes were gotton rid of before my parents moved to a smaller house. I was never 'caught' or anything that I know of but certain later events would lead me to speculate that my sisters and mother may have suspected something - Im just not sure.

Luv and hugs
Patti

Well I have worn my sister's clothes before back in the 70's. Just the other night my 14 yo granddaughter who lives with us spent the night with her best friend. She said that they dressed her friend's little brother up like a girl. Billie Jean

Patti,

We are close to the same age so yes, girls clothes and dresses were way more Girly than they are today. Pertticoats and slips and short dresses with puffy sleeves, lol!

What makes you think they might have suspected you were trying on their clothes ??

I thought I was lucky but you had way too much fun !

My sister is twelve years younger than I. I did not have any female playmates. For some reason the sperm pool in the apartment building I lived in only produced boys with the exception of one girl. I was rough and tumble. I got my butt beat too many times for childhood transgressions. However, I never had any thoughts of wearing girl clothes. I do remember when I was in kindergarten and wore a cowboy shirt. My teacher complimented me but she had called my shirt a "blouse." I was livid. I told her in no uncertain terms "It's a shirt,not a blouse!" I definitely set her straight on her error. I suspect if I did have an older sister or older female cousin (four male cousins) the thought of wearing a dress would have been repulsive. It was until puberty that some hormones sort of switched on the cross dressing genes.

WOW! JUST NOTICED THIS WAS MY 10,000 th POST. I THOUGHT I WAS GOING TO SAVE IT FOR SOMETHING PROFOUND TO SAY!

I was 7 when I was first left at home alone. I had just turned 7 when we moved into a single family house. (In an earlier post I said I was six and was wrong.) I don't remember why but I was into my sisters' closet ASAP. Everything was too big but not by a lot. My oldest sister was 17 and only 5'2" so the only one even closer in size was my Mom at 5'1". Over the rest of my time until high school I raided my 3 sisters' closets and drawers as well as my mother's. As I grew there was always something close to my size that fit me as my sisters were growing along with me. I ended up in the middle of them height wise at 5'5 3/4".
I lived on a street in a town on Long Island that was very close knit. There was one boy 2 years older than me and 5 girls my age or close followed by two boys much younger. So I spent most of my time with the girls. I never played with dolls but spent my early years bicycling around with them and going to the park or movies. We played hopscotch and board games at a different girl's house all summers. I even dared them to dress me up and they did. I was around 10 and was the same size as the girl next door. They dressed me in a pretty red chiffon over satin party dress of her's with a satin belt. Even her kitten heels fit. I stayed dressed all afternoon while we played games until her mother said it was time for me to give back her daughter's dress. No one ever dfid that again and I often wonder if they saw how much I was enjoying it.

i don't have any sisters, so I never got that opportunity, and not at a young age either. But i feel like my experience had similarities with some of yours. The culture of the family, dictated by Dad of course, was to hate any feminine tendency in males. So when, as a 15 year old, I discovered my mom's wardrobe and became fascinated and disgusted at the same time, as well as deathly afraid of being discovered. I felt certain I would be beaten half to death by dad, humiliated at school by my brother, then kicked out of the house and ostracized by my friends.

That said, my fascination kept me coming back every time i was left alone in the house. Mom had a cute little short sleeve sweater with puffy sleeves that fit me closely enough to give a bit of definition to my breasts. Slip into a pair of pantyhose and the erotic effect was overpowering. Still, I didn't accept that part of myself until more than twenty years later, and my wife didnt accept that in me for another twenty years after that.

I was about 12 when i first dressed. No sisters, so it was my Mom's lingerie and i could not believe how wonderful it felt. The first time I looked in the mirror and saw myself as a girl it was so exciting. After that, every opportunity I had I was dressing, I'm pretty sure that my Mom eventually learned of it, you can't fool your Mom, but she didn't say anything and I hope that she was ok with me exploring my feminine side.

It must have been 12-ish for me, too. Tried on my mother's panty girdles and stockings with garters. I don't remember trying on her outerwear at all. Maybe the pictures in the Sears Wish Book had gotten to me.

My sister is 4 years younger, so none of her things would have fit.

Being a latch-key kid I spent a lot of time alone at home. I vividly remember at around that age how unnerving it felt to try on mom's long leg, high waist panty girdle, look in the mirror and see a female shaped body with my head on it. A similar experience about that time was seeing the movie Invasion Of The Body Snatchers.

My earliest recollection is regularly being dressed up in my older sisters clothes by my mother. I vividly remember my favourite dresses were a green and dark purple velvet dress with puff sleeves with lace edging, accompanied by white vest with pink pattern and pink knickers, white socks and black sandal type shoes. Oh and a ribbon in my hair. Those were the days, and I loved every minute.

I had no sisters. I first tried on my mothers tights and I was hooked.