This story is more than 15 years old but it is still cristal clear in my mind.
I started playing with my ass in my young years and got more and more into it as the years passed. When I left home for college at 19 I was able to spend more time gradually wrecking my ass with my fingers and various objects. I quickly got obsessed by being able to fist my ass.
In my second year at college I wasn’t able to go home for Christmas and had to stay at the college for the holidays. It quickly turned into one week of me wrecking my ass for most of the day.
On the third day, after another session I went to the shower as I was all sweaty. But in the shower I still was horny as fuck so I stared fucking my ass again. I could feel it getting looser so I grabbed the lube and put it on my whole hand and went for it. My ass was resisting but I could feel stretching and at some point…pop my whole hand went in. The mixture of pain and pleasure was just pure bliss ! I cum almost instantly, and i felt my ass squeezing on my wrist. I was so horny that I was still hard even after cumming. So I started moving my hand again, I was able to take it out and put it back in before cumming another time. After that I took me several minutes in the shower to gather myself and I went for a nap just after that.