My first experience with diapers was when I was fourteen. Even though I was old enough to stay home alone, my parents felt it best if I stayed with a relative while they went on a second honeymoon. I was sent to stay with my mom’s aunt Rose, who I had only met twice before and lived two states over.
She was a bit of a clean freak and spent most of her time cleaning house. No shoes were allowed inside and she had covers on all of her furniture.
The third day I was at her house, I was outside playing with some neighbor kids and the urge to pee hit me. I ran back to the house and headed straight for the bathroom. I forgot to remove my shoes though, and my aunt grabbed me by the hair when she saw the muddy footprints I left on her carpet.
(It’s important to know that I have always been very small. Even at 36 years old, I am only 5’ 6” and 120 pounds.)
Anyway, she dragged me by the hair back to the entryway and bent me over the table that sat by the front door. Then she pulled off one of her slippers and began spanking me with it. She hit a lot harder than I thought she could and as much as I fought it I was soon bawling my eyes out. I tried to cover myself with my hands, but she just smacked them as well. Right after I started crying, I also lost control of my bladder and pissed my pants(and her floor). When she noticed that I pissed myself, she called me a disgusting little shit and spanked me even harder.
When she finished spanking me, she pushed my face into the corner and told me to stay put or get another beating. I stood there, still crying my eyes out, rubbing my butt for probably twenty minutes. My pants were now cold and clammy and I was completely ashamed of myself for allowing this to happen.
Aunt Rose came back with a wet wash cloth and stripped off my jeans and underwear as I still stood in the corner. I wanted so badly to stop her, but I didn’t want another spanking. I must’ve turn ten shades of red when she began cleaning me as I stood there naked from the waist down. When she finished, she took a handful of hair again and dragged me into the living room. There was a box sitting on the floor and on top of it was a pile of cloth diapers and a pair of old rubber pants.
(Another side note. I later found out that she had diapers and rubber pants, because she raised a disabled daughter that had passed away before I was born.)
Next to the box was a towel laid out on the floor. She told me to lay down and I knew what she intended to do. I told her there was no way I was going to wear a diaper, but my argument was short lived when she pulled a slipper off her foot. I couldn’t believe how fast I dropped down onto the towel just to avoid that slipper.
Aunt Rose piled up three of the diapers and slid them under my butt. They were already thick, but three of them was massive. She was clearly trying to make a point. She pulled them over my crotch and used four diaper pins to secure them. Then she pulled the milky white rubber pants over up my legs and over the diapers. I felt ridiculous.
She left the room for a moment and returned with a bucket of soapy water and a sponge and told me to clean up my piss puddle in the entryway. I had to waddle through the living room and get down on my hands and knees to scrub the entire entryway floor. She watched me the entire time as she used a special brush and cleaner to get the muddy footprints out of the carpet.
I sat in the living after that, humiliated beyond belief. Aunt Rose made dinner and then she made a show of changing my diaper before sending me to bed. The diaper was still clean, but it was clearly meant to embarrass me further. As she sent me to bed, she told me if my diaper was dry in the morning I could go back to my regular clothes. I had never wet the bed before, so I knew it was just another jab to teach me a lesson.
Being 14, I would masturbate at bed time almost every night and this night was no exception. The difference was that I realized how amazing the diaper felt when I got hard. I rubbed myself through the thick cloth for about five seconds before I had the most powerful orgasm of my life. It felt so amazing, I rubbed myself to orgasm three more times before I fell asleep.
In the morning, I got up and headed for the bathroom. As soon as I walked out of the room, Aunt Rose looked down the hallway from the kitchen and told me she would check my diaper in a few minutes, because she was in the middle of making breakfast. I almost fainted at the thought of her checking the diaper, simply because it must’ve been full of cum. I tried to come up with a way to hide it and contemplated using toilet paper to wipe it clean or something, but in the end I realized the only way to hide what I had done was to wet the diaper. It took me a minute to relax enough, but once the flow began I flooded the diaper all the way through. Then I just sat on the edge of the bed and waited.
When Aunt Rose finally came in, she could clearly see the diaper was soaked. I expected some sort of punishment, but instead she told me to go take a shower, get dressed and come to the kitchen for breakfast.
The rest of the day was pretty much the same as the first couple days. I was very careful not to mess up anything in her house and I avoided the slipper. Then, at bedtime, she asked me if I had a bedwetting problem. I told her no and she asked why the diaper was wet that morning. I told her it was only because I was afraid to get up and use the toilet. She actually laughed for the first time since I had been there, because apparently it’s funny for a teenage boy to be afraid of an elderly woman.
That night I found myself wanting the diaper. I missed the feeling as I masturbated and even wanted to experience the warmth of peeing in the diaper. I had to resign myself to fantasies though. That is until three days later, when I was dreaming about being in a diaper and wetting it. I woke up just in time to find myself peeing the bed. I ran to the bathroom as quick as I could to finish and used half a roll of toilet paper to clean up the wet spot in the bed.
My running around woke up Aunt Rose, who came to see what was going on. I tried to explain that I had a dream I was using the toilet, but she just ignored me. Turned out she had put waterproof covers on the mattress and just replaced the sheet. Then she went and got the diapers and rubber pants and put them on me as I lay on the bed. She didn’t say much the entire time and just went back to bed after sorting me out.
As much as I wanted to masturbate, I didn’t and went back to sleep. In the morning, the diaper was dry and I wore normal clothes after my shower. Aunt Rose didn’t mention it at all, but for the remainder of my three week stay I was put into diapers and rubber pants for bed every night.
To this day, diapers and humiliation have been my kinks. My wife loves it, surprisingly. She was a little iffy about it at first, but when she realized she could use it to lay down the law and get me to submit, she began incorporating diapers more and more. Now I wear them to bed every night and often through the weekend. She even occasionally puts me in a diaper for work, although that is a risky endeavor that requires certain factors to work out.