R I'm Jo, and I'm a sissy
My introduction, a longtime lurker de-lurking.
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Hello, I am Jo, and I am a sissy.

I am such a sissy.  I am wearing a diaper now, because I wore one to bed.  When I'm not in a diaper, I wear panties most days.  I went over 8 years wearing panties, and only wear mens underwear when I must because of my career.

To the rest of the world, I'm a man.  However, at home, behind closed doors, I'm a little girl at heart.

I know where it came from too.  My grandmother.

You see, my grandmother lived the next town over from my parents when I was growing up.  My parents took advantage of this for lots of free childcare.  More accurately, every weekend of my life since I was a toddler they'd drop me off at my grandmother's on Friday evening, and pick me up on Sunday evening.  During the summer, my parents would leave me there for much of the summer break from school.

My grandmother raised 5 daughters born over a period of around 20 years, and was part of that generation from the Great Depression that learned to never throw anything away.  Thus, she had a huge amount of clothes, girls clothes, and girls toys, and basically everything for a young lady between infancy and teenage years for the 1940's through 1960's.

My grandmother, by the time I was coming around, was starting to get just a little senile as well.  My grandfather had died of lung cancer about the time I was one year old, and my grandmother didn't take it well.  

When you're an infant, it really doesn't matter if it's pink or blue blankets, or anything else gender specific.  My grandmother, out of her practicality, re-used the same blankets and baby dresses that my mother and my aunts had as little girls.

As I grew up, my grandmother much preferred to keep me in the girls clothes she had, and to treat me as a girl, just like my mother and my aunts.  She'd never raised a little boy, and in her senility I think she was either in denial that I was a boy, or didn't care.  In either case, I'd be dropped off after school on Friday, and promptly take off my boys clothes and put on my dress.  I'd spend the entire weekend in a dress, playing with dolls and tea sets and other "girl" toys, and only go back to being a boy when it was time for my parents to pick me up on Sunday.

My grandmother also seriously, and I mean very seriously, underestimated my overall level of maturity.  I was in grade school, and she treated me like a toddler.  When I was 6 or 7 she was amazed I was potty trained.  One big impact of this was that she was always afraid I was going to wet the bed.  Thus, every single Friday and Saturday night of my life from the time I was born, until around the time I was 13, I was in a diaper for bed.  If we were going on any long car ride, basically anything further away than just the same county, I was expected to be in a diaper as well, "just in case".  In practicality that meant if I needed to go, go in the diaper because they wouldn't pull over for a restroom, after all, as she explained to me, that was why I was diapered: so we wouldn't have to pull over for me to use the restroom.

There were other impacts of her thinking I was far less mature than I really was, like her insisting on cutting up my food and feeding me until I was around 11.  

The net effect of all this was that for 2 days a week, and about 2 months a year in the summer, I was treated as if I was a little girl.  I was loved and adored and spoiled as grannys little Princess, but I was most certainly a Princess and not a Prince.

This all came to an end when I was 13, almost 14.  I was going through puberty.  One night, in the middle of the night I woke up with my first erection.  I was aroused and hard and it was keeping me awake.  Well, I didn't know what to do.  I started playing with it, and quickly discovered masturbation.  I put my hand down my diaper and started to masturbate.  Before long, I felt the rush of my first orgasm, and I spilled my seed into my waiting youth diapers.  I didn't fully understand what semen was, only that I'd just messed my diaper.  I was used to the diapers absorbing my urine, and didn't know it wouldn't do that for what I just did.  In any case, the orgasm helped me get back to sleep, and I slept through the night.  

Sure enough, the next morning my grandmother came into my bedroom, that pink palace that had been my bedroom since infancy, and had been my mother's room as a kid as well.  As part of the usual routine, she undid my diaper and was going to check to see if I wet the bed.  I'd stopped wetting the bed at 9, so for years this check was purely a formality.

However, she could see my emissions in the diaper.  She got this look on her face.  Worry.  Concern.  Sadness.  I was worried that what I did was wrong, or was a sign that I was sick.  I went about my day as usual, taking a bubble bath and putting on another dress and being a girl, then went back to boy mode at the end of the weekend.  

When I came back the next weekend, all the girly stuff was put away.  No dresses, no panties, no nightgowns or dolls.  Instead of sleeping in the pink bedroom, I was given a blanket and a pillow and expected to sleep on the couch.  A few T-shirts and blue jeans bought at the store had replaced my wardrobe of dresses and skirts and blouses.  My grandmother had gone from doting on me as a little girl to wanting me to be a man, and I was suddenly expected to chop wood, do lots of chores and tasks around the house, and any show of femininity was frowned on strongly.

I wasn't a little girl anymore.  I would always miss being granny's little princess.

I know this is why I am a sissy.  I came to associate being a little girl with being loved, and being safe and comfortable, to associate wearing a diaper with being safe and loved, as well as orgasming (having my first orgasm in a diaper has to do something for you).
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Baby Butch
 Nice introduction, it is almost like a story. A grandmother like that would be great to have for both being feminine and being babied.

I have had a few similar experiences mostly with an aunt, sister, or my mother.

Welcome to Sissy Kiss from a big baby who still wears diapers!

Ye, welcome to the forum, and quite a lovely introduction to yourself. I am sure there are plenty of people on here who wish they had as a supporting family member as you growing up(even if it was only until puberty), but, still very lovely introduction nonetheless..
Sorry to hear your princess days came to an end in such a sudden, rude fashion. Here you can always be a little girl princess. Here, expression of femininity will never be frowned upon. Welcome to our club!

I look forward to seeing you around!

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