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Crossdressing reasons
#1
I started with my sisters panties and bras since then i am hooked at age 14..now i am 31

Why one gets addicted to it ?
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#2
i start at 13 with my mom stuff. I was home alone and explore it. I continue for a year before my mom found out and she hate the dressing. Send me to therpy which didn't help at all. I am now 53
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#3
I started exploring around 12 or 13 although the 'need' to goes back a lot earlier than that finding things in PTA collection bags having the rotten luck just to have brothers and borrowing the odd top or skirt that wasn't to removed from a senior outfit from Mom moving towards walking into lingerie stores and buying my own in my twenties (newsflash! It's a all a sale to them!).
I started getting more uniforms shortly afterward buying from catalogues that dud stock stuff in adult sizes until I found online suppliers with Big Kids ranges so it would be identical to that actual worn and wear my uniforms (pinafore dresses or red/maroon tops with blouses etc) everyday and when I'm with certain adults who are more parental Caregivers, I'm required to take them with me as homewear around them.
It's just me being how I see me ultimately.
Gender fluid Feminine Boy "Jane Girl"
My Tumblr
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#4
With me it started as a punishment from the age of about six, when my mother started making me wear a pair of my little sister’s knickers for a spanking. That developed into her making me keep the knickers on for a while after my spanking, to having to wear a dress or skirt as well.

After a while Lucy complained so much about me being put into her clothes that I was bought my own. For a while I was dressed identically to Lucy (she’s two years younger than me), and then I was dressed younger than her, and finally put back into nappies and baby clothes.

It was terribly humiliating, but having to wear knickers or nappies, especially to bed, while going through puberty resulted in certain associations in my teenage mind. Now I love to be humiliated, and to wear girls’ and baby clothes.
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#5
I could not resist borrowing panties to try - it was far far too exciting for me and blew my mind... I've been obsessed with cute panties and feminization ever since. PM me if you'd like to know more.
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#6
I was mostly always dressed as a girl . I only took to male clothes in my teens because i wanted to get out and meet girls .
Angel A little bit of hanky panky does you good .  Angel
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#7
With me it started when I was very little, I used to play with my mother's knickers. It abated for a while but came back strongly throughout my teen years. I would take every opportunity to dress up in my mother's underwear.

I started work at 18 and from then on bought all my own clothes, make up and perfume so I could explore my very intense crossdressing desires.

I am totally obsessed with ladies' knickers. I always have been, always will be, and to be honest I wouldn't have it any other way.
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#8
I started at about 8, when I tried on my sister's leotards. She had two, one light blue with a scoop neck and 3/4 sleeves, and a black and white one with a turtleneck and long sleeves. Leotards are still among my favourite girl clothes, particularly with a pair of dance tights or gymnastics leggings underneath.
I moved on to my mothers knickers and tights. I remember locking myself in the bathroom where the airing cupboard was and putting on a pair of knickers, then a pair of tights, then another pair of knickers, another pair of tights, and so on. I think I wore 6 pairs of knickers and tights at once, enjoying how with each additional garment the whole lot felt tighter and tighter. I still love the feel of tights on my legs, and find being tightly enclosed a big turn-on.
When I was 12 I borrowed my sister's navy blue school knickers, her pleated netball skirt and a pair of my mother's tights. That's what I was wearing when I had my first ever orgasm, stimulated by the feel of the sheer nylon on my legs, the soft knickers clinging to my penis and buttocks, and the pleats of the skirt crisp under the fingers of my left hand (my right hand was busy...).
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#9
Whem I was little and wet the bed I was diapered  by my mother and since my boy pajamas were  wet I was  put into my sisters pajamas.  When mother saw that I was having erections she spanked me and then forced me to wear diapers and girly pajamas, play with dolls and  use a pacifier. My little sister loved to dress me up and be the babysitter. I am still  a fetish crossdresser, sissy baby
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#10
I had just started kindergarten early (age five) and had also started having wetting problems again. One day, when the bus let me off at my babysitter's after morning kindergarten, I couldn't make the walk down the long driveway before tinkling my pants. My babysitter, a woman in her forties, got me out of my wet pants and laid out some clothes belonging to her children in the bathroom for me to wear while my pants dried.

Unfortunately for age-five me and fortunate for sissy me, all her children were daughters. I still remember staring at a pair of black stretchy pants, a white blouse with some sort of purple floral pattern, purple socks, and a pair of white panties also with purple flowers. I recall kicking and screaming until she compromised and said that I didn't need to wear the socks, which had anklet frills.

However, the most shame of the day came as her four daughters all returned from school one at a time. Having young ladies and women come in and burst into giggles and laughter as they saw a naughty, precocious, little boy in bits and pieces of their old wardrobes. While I took no pleasure in the humiliation that day, I would soon find myself having accidents or getting my clothes muddy intentionally so that my babysitter would keep putting me in her daughters' things. By the end of the school year, she had a closet with several little outfits for me.

I've never fought wearing panties since!!!

<3SMR
There once was a sissy so fair/ Who went out to breathe the fresh air/ When a bully did try to pull her panties aside/ He was surprised to find that she had a spare pair!
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