I have masturbated in my diapers since I was 11 as well. But my first orgasm was on a class trip at school when I had to hold my pee about half an hour. I was wearing Depend Undergarments underneath my Sears Nylon/cotton/polyester Golden Comfort gold striped white brief. Over that was my navy blue uniform polyester slacks. I went to catholic School so in elementary school we had navy blue slacks and light blue shirts as our uniform and school tie. The uniform slacks were cotton but some of us kids wore polyester slacks from Sears or Pennys. I wore polyester in case I needed a change after an accident in my undergarment liners or pull ups. I could go to a private room and quickly remove my slacks without taking my shoes off. Also good for gym days for quickly removing slacks where on such days we wore our uniform shorts under and in winter sweats under my slacks.
Anyhow Our class trip was an hour long bus ride. When arriving the need to urinate was bad after holding at least 15 minutes. Still 10 more minutes when we arrived till we could get to a bathroom. Well I made it after letting some spurts out into my Depend Undergarment. I peed and peed and peed. I was moaning "AHHH MY BLADDER..FEELS SO GOOD...AHHH AHHH". Classmates just figured "Thats Chris" though a couple others moaned in comfort as well. After zipping up my bladder felt soothing. I begin to get hard and feel something else is still in my bladder though no stinging. I push to let out what I thought was pee and I GUSHED about a Pint of wetness out but it felt slimy. I thought I peed my pants and was afraid my depend was gonna leak. But it held. I had to piss an hour alter and went in the bathroom and noticed my depend was sticky. When I got home the Undergarment was sticky and stained and dry and out of absporbancy and worn out. My underwear was also stained yellow and light brown in my frontal area. That night when Mom diapered me up in my Abriform thick youth diaper I got hard again and rubbed at the comfort and I orgasmed again. At 12 Mom stopped diapering me and I began to diaper myself. I used to take my glasses off (wore since I was 5) when I was diapered for bed. But since my first orgasm I keep them on till after I cum.
Since 12 I would diaper myself, then put my navy blue or grey polyester slacks on, let any pee out into the diaper, keep my glasses on, hump a pillow laying down on my stomach, and pretend I am urinating in a urinal at school. Some days I pretend to talk to my buddies about my bladder problems as I am jerking off. Other times I pretend I am doing a diaper commercial about my weak bladder. I would pretend to be urinating as I cum dressed in my slacks and shirt and all. After finishing I crash and the desire to jerk off leaves me. I then take my slacks off, glasses off, and fall asleep. In high school I wore Attends Undergarments as well and for slacks wither navy blue polyester, grey polyester, light blue/grey polyester, or light tan grey polyester (all usually levis Action Slacks). Sometimes I orgasmed during class after peeing before.
Today I have a pair of each color of polyester slacks similar to what I wore as a kid and I still jerk off diapered up the same way reliving my school days. I still wet every night and sometimes during the day. Sometimes when jerking off I moan and talk about my bladder problems. Other times I just pretend I am urinating and moaning how good it feels to drain my bladder. Other times I just say "IM A GEEK IM A GEEK IM A GEEK" as I orgasm. I still keep my glasses on when I jerk off...Now I am 30 so i am celebrating 20 years of jerking off in diapers.