There are many, but probably when my babysitter diapered me back in the early 1990s when my mom was away on another business trip.
I was six years old and after we had our bath time, I followed my babysitter into my sister's room to watch her diaper my three year old sister. Our babysitter was a cute young woman in her 20s. She had long dark brown hair, brown eyes, and an easy smile.
My babysitter saw my little stiffy, and asked me if I wanted her to put a diaper on me too. I said yes, so after she was done diapering my sister, she put me up on the changing table.
My babysitter seemed to be having fun with this because she started to tickle my bottom. She rubbed baby lotion on my bottom, then spread my legs and rubbed baby lotion on my little boner. That felt incredible!
After that came some baby powder, and then she diapered me with a pink Luvs diaper for girls. I could hear that wonderful plastic baby diaper crinkle sound as she unfolded and then slipped the diaper under me. When she pulled the diaper up between my legs, I couldn't believe how hard I was and how good it felt as she taped the diaper on me. My babysitter thought it was cute too.
I wore my diaper to bed that night and humped it until I had a couple of dry orgasms, and then wet it on purpose before I fell asleep. I may have wet my diaper even more during the night because when I woke up, it seemed soggier than what I remember.
The next morning she noticed my wet diaper and asked if I wanted her to change me. Of course I said yes, and I got to wear diapers for the rest of the day and had fun wetting and playing with myself.
I played outside in the backyard wearing nothing but a diaper, and my babysitter would occasionally check my diaper and change me when I needed it. My sister thought it was funny at first, and we both laughed about me wearing diapers too.
That night I wore a diaper to bed again and humped my diaper and wet it before falling asleep.