My parents loved to find reasons to leave me with my grandmother. I think it's so they could still party and try to be social climbers. My parents lived in a city. . .my grandmother lived 2 hours away in a big old house in a very rural area. Every weekend, they'd drive 2 hours each way to drop me off, and pick me up, so they could have fun on the weekends without me. During the summer they'd take me to my Granny a day or two after the last day of school, and bring me back a few days before school started, meaning I spent a couple of months with my Granny and would only talk to my parents by phone all summer long.
My grandmother lived alone, when she wasn't with me. My grandfather was killed in the Korean War, when my mother was an infant. My mother was the youngest child of 4 daughters, all raised by my grandmother. Then, all the grandchildren (that my granny actually saw or dealt with) were girls. It basically meant she'd had decades of experience at raising girls, and was from that Great Depression generation that never threw anything away.
That meant she had a huge collection of girls clothes, everything from baby clothes through teenage clothes, of fashions from the '50's and '60's, and that my grandmother only had experience in raising girls.
It also meant that my grandmother was in her 60's at the time of my childhood in the '80's, and we didn't know it at the time, but she was getting the onset of some kind of senility. I'm not sure if it was clinically Alzheimers, or some other form of dementia, but her sanity was slowly eroding.
I had my own problems. I had a severe bedwetting problem as a kid. I basically wet the bed every night of my life until I was about 7 years old, and still wet fairly often until I was about 11 or 12, when it tapered off to being something that would happen two or three times a month. I didn't completely become dry at night until about the time I was 17.
My parents just washed the sheets often, and figured I'd grow out of it. They really didn't like the idea of using drugs, and an alarm didn't help (it just meant I didn't sleep well most nights when they used it), and attempts to restrict fluids before bed were only modestly successful. My grandmother's solution was that she had lots of cloth diapers and plastic panties from the childhood of my mother and my aunts. I realized somewhere along the way I was literally wearing the same diapers my mother wore as a baby.
Since she diapered me for bed from before I could remember, I was just used to wearing a diaper to bed at night when I would stay over there. I came to like it, I came to prefer wearing a diaper to bed because it meant I could wake up in a dry bed. My parents knew, they didn't entirely approve of it, but they knew. I asked if I could wear a diaper to bed the rest of the time, but they disapproved, saying that they didn't want their son wearing a diaper to bed, that somehow that would be "condoning" my bedwetting. To be honest, I resented the heck out of that, since it's not like I was choosing to wet the bed, but I had definitely come to like wearing a diaper just so I could get a good night's sleep and not wake up in a soaking wet bed, just with a soaking wet diaper.
Somewhere along the way, when I was in grade school, I got too big for even the biggest cloth diapers and plastic panties she had. She apparently tried to go to a drugstore in town to buy bigger cloth diapers. I guess that in the '40's and '50's you could just buy cloth diapers at the drugstore, but not by the '80's. The pharmacist apparently helped her special-order some "youth" sized disposable diapers, so one weekend I showed up to disposable diapers awaiting me. Exactly what you'd expect, they were just like baby diapers, except sized up for me. Somehow I'd gotten used to cloth diapers, and the disposables felt far, FAR more babyish. I guess that since I didn't wet the bed every night, I could on many nights delude myself that my cloth diapers were just rather bulky underwear, since it was still cotton cloth against my skin.
The crinkle of the plastic diaper (which seemed far louder than my plastic panties), the fact she was very unabashed about leaving the pack of diapers out, the whole experience just seemed to be very infantile. I was in grade school, and my granny was diapering me for bed every night like a toddler. . .and the disposables just seemed to make it much worse. Then I realized that I'd never really even been entirely dry at night. I was so used to wetting the bed, and my Granny had been diapereing me my whole life, that I never really thought about it until that first time I was being taped into a disposable diaper that in one way I guess I'd never even been fully toilet trained. . .I still needed to wear a diaper to bed at night. My parents wouldn't diaper me, but that didnt't mean that I didn't NEED a diaper.
That would have pushed me in a sissy direction, being diapered every night throughout my childhood and teenage years.
. . .the dresses sealed the deal.
You see, my grandmother was definitely slowly losing her mind. She'd raised girls, she knew how to raise a girl, she had girls clothes and toys. . .and when I was an infant or toddler being left with her, it was nothing to just put me in a dress and let it be, but she kept doing it. Basically when I'd go to stay with her, she'd pull out one of my mother's (or my aunts) old dresses and that would be my clothes for the time. She had old panties and slips and nighties for me to wear too. . .and in later years there were training bras waiting for me too. She loved to dote on me as if I was a little girl, and I came to just get used to the idea that when I was with Granny, I was a girl, and when I was with my parents, I was a boy.
Granny taught me how to paint my nails, and do my makeup. While my parents kept my hair short, my grandmother had me grow it out during the summers. She'd play with me with all the various dolls and other girls toys that she had saved up. I took lots of bubble baths. I learned a lot about modesty and decorum, about how to dress, sit, walk, talk and carry myself like a proper young lady.
In retrospect I realize that all that upbringing in how to be a good girl left an impact on me the rest of the time. I was definitely not a bad boy, I was shy, timid, passive, and submissive as a boy. I think it carried over to my body language, the bullies always loved to tease me and call me a "sissy" even when I didn't have a stitch of girls clothing on, like they could just tell. . .and girls never seemed interested in my as someone to date, just as a friend.
If there was any doubt on me loving diapers and girly clothes, having my first orgasm in them sealed the deal.
I was about 12 or so, a few years after my granny switched me to disposable diapers, and around the same time she started insisting that I wear a training bra during the day. I woke up in the middle of the night with a mighty erection and feeling very aroused. I liked the feeling of the slinky nylon and lace nightie I was wearing, and had woke up to my diaper being recently wet. I'd wet the bed again, and the warmth between my legs let me know it. I started to play with myself, feeling my body, I realized I loved the feeling of touching my nipples, and touching my erection. . .and before long I had one hand down my wet diaper playing with myself and another hand teasing my nipple, and I felt that huge rush of pleasure of my first orgasm as my first load of seed went into my wet diaper. I had no idea what it was, other than it felt good. . .and it forever cemented an association in my mind between dressing girly and diapers and arousal.
It was also around this age that I got large enough for the nylon panties my Granny had saved up, so I went from plain cotton panties to nylon panties with a lace waistband. . .and realized how they felt so incredible. It wasn't long before I was pleasuring myself most nights in my diaper, or when I could through my panties.
When I was in disposable diapers, my Granny checked my diaper every morning to see if it was wet (and if she'd have to wash the diaper), but since I was in disposables now, I could just throw it away in the morning. She didn't see that I'd come in my diaper, and for that I'm thankful.
This would all go on until my teenage years, when I went off to college right before my 18th birthday was when this would stop, because I ended up going to school on the other side of the country. It's where I got a full scholarship. I was just thankful that my bladder was finally under control. . .I didn't want to deal with the possibility of wetting the bed in college. I did miss being granny's nice little girl though. I'd come to like the feeling of diapers, even if I didn't really need them anymore, and I came to miss wearing dresses and skirts, of being a good little girl. I realized that in my heart I was basically a little girl with a very weak bladder, who wants to be in cute dresses and a nice diaper, playing with my dolls.
. . .I still am that little girl who belongs in diapers at heart.
