Anal Pleasure

As I removed the plug from my ass it hurt quite a bit again, (maybe because as I've said before the head of the plug is a lot thicker). But i was still very curious and decides it was time for the dildo.
I put on a lot of lube in the dildo and in my ass as slowly started to insert it. However, after pushing just a little it in, not even the full head in, the pain was just to much.

I decided to power through it and slowly work the fake cock into my ass. I hurt like hell so I decided to go back to the plug. I reinserted the plug and i stared pushing it in and out and trying to go faster as if i was getting fucked by the plug. it really hurt a lot but I thought it would expand or dilate my butthole enough so that i could put in the hole dildo.

It worked! after doing this for a while and pushing through the pain I felt that my ass was open wide enough to take the dildo. I put on more and more lube and started to push the dildo into my ass again. I managed to go deeper but the pain was almost unbearable, I started jerking of again to try to help with the pain but it didn't work. At first my dick was not hard, and as I jerked more and more to try to get it harder and I started to feel pleasure from the jerking, the more i felt like my but was closing up and couldn't take the dildo.

So, I stopped jerking and decided just to push through once more and after a while of slowly shuving the dildo up my ass, I was able to put it all in or al least most of it in. ( I got the head of the dildo dick inside, which is the thickest and hardest and most painful part to get inside.) I don't think I was getting any pleasure from having the dildo fully inserted up my ass, but I know I was getting a lot of pain for it. Nevertheless, even though it hurt like hell, i still wanted it in, it was a bit bizarre but i kind of thought that eventually the pain would stop and the pleasure would come. However, this was not the case, after give or take 10 mins of having it it i got no pleasure and the pain continued. It did feel kind of funny and in a weird way kind of like taking a shit but in a good way. But the pain was just to much and a took it out.