I never understood what painful anal was until I tried it with my last girlfriend. She pretty much turned me off of anal altogether within a matter of a few seconds. I guess I should have been a bit more prepared for what was going to be happening but she never once clued me into the fact that she would be doing it to me. That is a very scary situation, if you aren’t prepared. Thinking back on it, I should have been more careful in my attempt to be pleased that she wanted to try anal with me.

Now, painful anal to me is not what it meant to her, which is evident in the fact that I wasn’t aware that she was going to be strapping on some huge ass dildo and ramming it in my butt. I thought maybe it was going to be me fucking her ass with no lube or something, but that wasn’t what she had in mind at all. In fact, it was the exact opposite of what she was thinking. That made me pretty happy that she decided plenty of lubricant was going to be needed so she wasn’t dry raping my ass all night.

The worst thing about the painful anal experience is that she didn’t even tell me that it was going to be me getting it in the ass until she was just about ready to push it in. I thought she was going to do something that was going to make me extra hard for fucking her. She had me up on my hands and knees and put a blind fold on me telling me that it was the surprise that made it worthwhile and that I was sure to enjoy what was going to happen to me. Why did I forget that women lie?

I know that if she would have told me what was about to happen I would have put a stop to that painful anal thing immediately, but not knowing it was coming I was in total shock when she said “Relax” and slid that monster part way into my ass. I screamed and tried to crawl away but she just forced it even farther in. I think that is where I partially passed out. I came back to the world when she started ramming it in and out and that was all I was going to take anymore. I got up, dressed, and never looked back.