I had a cousin who slept over at our house often when we were growing up and she was especially attached to me at the time.
She is 6 yrs younger and was rambunctious as a kid.
On one sleepover, we shared a bed while my sister and another cousin shared another bed in the same room.
My cousin was a heavy sleeper who would also take up a lot of the bed.
I often had to move her back to her half of the bed and was surprised she slept through the jostling.
I was very horny that night so when i realized she would not wake up I decided to try my luck at sliding my hand under her panties.
I was able to (very carefully) slide my entire pinky in her anus without waking her up.
I've never told anyone this.