Growing Up Girl Free

I've noticed reading, and watching youtube that often crossdressers grow up with some girl in their life that helps inspire their dressing in some way. Was that the case for you?

I was the first born son in my extended family, a couple years later followed my brother. Then a string of cousins, every year or so, 6 in total and every one a boy. It was obvious that all the women of the family were just a bit disappointed with the lack of girls, they weren't overt about it, but things would slip. I remember my Grandma once joking about wishing she could put me in an Easter dress. On one side of the family no girls ever showed up until my cousins started having kids then it was nothing but girls. On the other side of the family I eventually had a girl cousin when I was around 13 and my grandma finally had that girl to spoil, I was so much older that I don't think it had a big impact on me, but I do remember being somewhat jealous of all the attention she got.

My Mom had wanted to have another baby and my Dad didn't, as usual my Dad won out, I was sure that my Mom wanted another to try for a girl, and I was always really sad for her and the rest of us that my Dad had been so adamant about it. I remember sitting at my Mom's vanity and combing out my hair in as girly way as possible and sort of wishing that I had been a girl.

I didn't have a super strong urge to crossdress back then, and no way to really experiment. I wasn't about to go buy girl clothes with what little money I had. If there had been a sister or girl cousins I'm sure that I would have at least stolen some panties.

Nope, raised in an all male household.

Not me second of two boys, fact my mom always said she was happy she had boys because little girls are too whiney.

Hi Sarah, so when did the urge to crossdress hit you?
I had a much-older sister that dressed in stylish and sexy 60's clothes, and a rich and beautiful next door neighbor that dressed in very chic clothes who let me have access to her house at an early age to walk her dogs (and explore her closet), so I had a lot of inspiration.

I had an older sister by 3 years and an older brother by 6 years. My dad was an alcoholic and was out of my life most of my childhood. I believe my dad who tried to be that macho man but was a complete mess whom I completely hated, made me hate the traditional male role. My brother definitely wasn't a macho man, but he was much older so I was much closer to my sister anyways. My sister and I would play dolls, play house a lot, and she usually controlled the remote so more feminine television programs with her. Once I hit 8th grade with my brother moved out for college and it was just my sister and mom, this is when I started secretly dressing in my sister's clothes. My mom wanted my sister to be a girly daughter but she would rather be a tomboy, so she would never notice me wearing the skirts and dresses my mom bought her that she never wore unless forced for some event or something. I don't know if I was trying to fill that role subconsciously because I know for sure me being a CDer was way worse for my mom than my sister being a tomboy.

I'm the middle of three boys. I have some female cousins but rarely saw them growing up as they were too far away or they were older so they really had no influence on me.

I have an older brother by one year. And, a sister who is almost twelve years younger. I had four male cousins. As post World War 2 kids, we were pumped out every year. There must have been some Mother Nature thing to replenish the world with guys killed off in the war. Even in the apartment building I grew up in there were few girls in my age group. We had enough guys in the building to field a good sized baseball team.

The only influence I may have had concerning external forces on any potential cross dressing was my mother saying more than once I was suppose to be a girl because I had an older brother. Her ideal family was husband and wife, son and daughter. I remember it upset me to the extent once I donned her nylon nightgown and cried "she did not love me because I was not a girl!" She consoled me that she loved me and all that rubbish. That made me feel better. I still think she wanted a daughter. When I think back to those days of youth the discipline handed out to me was more severe than what my first born brother got for similar transgressions. Through all my growing up I was rough and tumbled, got in a lot of trouble, unruly at school. My urge to wear women's clothing did not materialize until puberty.

I have an older sister that was quite voluptuous as a teen and she often scampered around the house in nothing more than pretty bra and panties while getting ready for a date. Rather than normal male admiration, I was envious of her pretty lingerie. She did make me over one halloween and the neighboorhood could not believe how good I looked as a girl. I remember stealing a pretty yellow slip from her which I wore under my boy clothes to go fishing with Dad no less. I'd sneak away in the woods, take my boy clothes off and just marvel on how pretty it looked on me as well as how good the silk felt. This age 6 - 8 maybe. Yeah, girl since an adolescence, no doubt.

I have a sister two years older than me, and in my teens we were very similar in size and weight. It was putting on one of her dresses when I was 15 than changed me from just getting gratification from wearing undies and such, to wanting to look as much like a girl as I could.

Yes brothers and sisters in my family, but Mom put me in a dress when young: have a picture.

I grew up in a household with three older sisters. My father would work long hours and so my Mother and sisters were strong influences. I was surrounded by feminine things and feminine ways. They dressed me and one sister would put makeup on me.
I have always thought that this was the root cause of my cross dressing but from my reading here I am impressed by the number of cross dressers who grew up in a more masuline world.
We have all ended up in more of less the same place yet our paths to this place have been so very different. That is what makes it so interesting.

I grew up in a mostly male free environment. My father was in and out of jail and mental hospitals and when he wasn't he was "gallivanting around" according to my mother. He left for good when I was about 8yo. I was the only male in the house along with my two sisters, my mother and grandmother. Even the cats were female. I didn't have a very positive idea of being male. Most of the men around me were drunks, molesters, criminals, bums or just plain stupid and scary. There were no boys in the neighborhood my age. The ones that were older were thugs. The only positive images of males I saw were were on TV or movies and I didn't identify with the hero or tough guy types and I wasn't all that funny. The types that I did identify with (nerds, sissy boys, sensitive types) were not generally presented in a very positive way. I sure all this had something to do with my feeling that I would be better off as a girl.

I was a late in life child. Had a step sister that was 13 years older and we had little contact as she was in high school as I reached an age to really bond, then away to college. As a result we were never close. Thus no female influnce. But a female friend led me to this site as I started dressing and strongly supported me along the way, even going out with wheh I dressed. This site opened the world to me and made me feel good about my female site

Nope, not me!
Lucked out being the only boy with five sisters :o :cheer:
Plenty of fun to be had growing up with them :battingeyelashes:

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It seems to me that having girls around may have made dressing easier but probably wasn't a factor in why we start doing it.

Millisense: I started having weird feelings about things when I was probably in the second grade, so around 7. My mom had a spare bedroom and I found a drawer that she kept frilly things in, lots of lacy poofy things. Nothing fit but I played with the stuff a bit. I remember playing with her makeup and getting in trouble for it. I'm sure if I'd had access to girl clothes that fit me I would have worn them. I didn't actually do a full scale cross dressing experiment until about 4 years ago, had no clue what I was doing with the makeup and looked like a nut and felt really ashamed about it.

This is the story my mother often repeated to us. My mother wanted a daughter and my older brother was born. When she was pregnant with me she prayed for a daughter and did everything possible to make herself believe that she could will to birth a daughter. So when I was born I was a disappointment. I was only six months old when she found herself pregnant again. Could she dare seek a daughter again and risk another disappointment. Well on Christmas Day my mom gave birth to my sister. She had her daughter and it was the happiest day of her life.

My sister grew up as the pampered princess of my mother, and I grew up believing that my mother would love me more if I was a girl. I thought that all parents preferred girls because girls were better, smarter, prettier, and never caused problems like boys do. So for as long as I can remember I found that crossdressing was a way I could fix my world.

I had three older sisters. Needless to say you know where some of my clothes came from.

I am an only child, and the closest female relative in my generation (a cousin, 12 years older) lived over 300 miles away. However, my mother and grandmother were big inspirations and definitely influenced my sense of style.

- Diane

I was an only child raised by a single mother. My mom was a strong willed woman when that was not particularly fashionable. I grew to admire her and other women like her. The lack of a male role model and the admiration of a strong, independent women has shaped my perspective accordingly.

Nope. Middle child of three boys. She raised all three after divorcing my father when the youngest was 5....
I have no idea how my mother did it!

Although I have sisters, they were raised by my mother and stepfather. I lived with my father and stepmother where there were just five boys. But my stepmother was a socialite. She dressed very well. Sometimes changing outfits three or four times in a day. I do not ever remember this woman wearing pants. When I was little she used my closet for her overflow. One day, after a quick outfit change she left a pair of pantyhose on my bedroom floor. I don’t know why I put them on, but I was in heaven.

I have five older sisters. Not sure what their influence was as they never dressed me.

Except for one instance when I was going to go ice skating, and my long johns were in the wash. My mom had me wear a pair of my sister's tights
instead. One of my sisters helped me with them and was amused doing so! I did share a bedroom with two of them until I was 10, I learned to ride
a bike on a girls bike with the same two sisters running beside me until I learned to balance. I likely watched more beauty pageants than most of my
male peers when I was very young!

No sisters, youngest out of 3 boys. I have a similar story as Confucius. When my mother was pregnant with me she wanted a girl. Growing up I heard that story over and over that I was supposed to be a girl. I don't know if that was the reason I became a crossdresser, it was probably a factor but I believe other things influenced it too.

I have a sister who is three years younger than me. She was much smaller than me and had no clothes that came close to fitting me. I spent all of my youngest crossdressing days trying on my mom's undies and nylons.

Was girl free except for the next door neighbours, they played girl games and so did I.

I dressed appropriately to fit in with them.

Hi sarah…

No particular female role model (for dressing) in my family; second of two boys. I was drawn to the softness of some of my mother's clothing and my personality was rather equally distributed between male and female (couldn't qualify that with data; it's just how I've always felt.) My father was emotionally shut down, gruff and explosive so I suspect this pushed me towards my feminine side of emotional communication and equating this with a preference for wearing softer and more stereotypically female clothing (lace, lingerie, dresses, various colours.) I do always feel much calmer in a satin blouse and skirt with heels than I ever did in a suit and tie.