So, a while back, during my senior year in HS, I started to experiment with anal insertions. I started with a pen or marker, and found it to be an amazing feeling. I wanted more, so when I was in the shower, I started with my fingers. I got some sort of lubrication...prop was conditioner, and started going at it. I got one finger in and my dick got so hard. I had never felt that good. I needed more, so I went to two and three fingers... the pleasure went up and up. then I had a shampoo bottle about 1.5 inches in diameter, and started to stick that in my ass. when I got that in, I started to rub my massively hard dick, and  before I knew it, I was cumming. I came so hard, it practically shot across the room. I had to take a break.

The next day, I knew what was possible, and how good it felt. I was ready for more. I needed more. so, that night, when I went to take a shower, I went back at it. I got up to 2 and 3 fingers, and the bottle again, then i got 4 fingers in. oh god, I was ecstatic. I said, what the hell, I would try 5 fingers. I got all the way to the knuckles, but it wouldn't go any further. I grabbed my dick and jizzed all over the place again.

Then, the next day i wanted my fist in my tight asshole. I knew that it would fit. It had to fit. I was so turned on all day as I thought about what I was going to do that night. when I got home, I was so horny, that I had to blow my load. I then did some homework and after that....shower time. Or, maybe it should be called fisting time. I got in the bathroom, and was already hard. I worked up to 5 fingers again, and to the knuckles, but it just wasn't quite going in. I got on my knees and tried that position. it was better, but it was obvious that it was going to take some workin'

As I worked more and more in, ever so slowly, i got really excited. I thought about what it might feel like. I figured it would hurt a bit, but I didn't care. I wanted my asshole to get stretched to the limit. I pushed and pushed more and more, then....finally, POP. my fist popped into my ass. I felt so full, and never had felt so good. I was amazed that even tho it hurt, i loved it. I came so hard but left my fist in my ass. I pumped it in and out for a few minutes, then made a big fist and pulled it out. I put more lube on, then slammed my fist back inside. I started punch fisting and came again. I was exhausted. I took a really fast shower then went to bed, dreaming of the possibilities of fisting my asshole.

That was a few years ago, and have been fisting my self since then. I even got my girlfriend to fist me, which was even more amazing then when I fist myself, but that story is forthcoming...