I went out to the bar with some friends tonight and ended up going home with someone- let’s call him tim. I have hooked up with Tim in the past and it’s always amazing but tonight I was feeling like I wanted more. I started to suck on him while he was laying down and he went and got a toy we bought together a few weeks ago, instantly he put it in my pussy and started rubbing my ass with his fingers. As time when on I was still sucking on his thick dick & he switched from my pussy to my ass with the toy. I never have liked anal so I pulled away, he asked me to relax so I did and soon enough the toy was in my ass. It felt good but he was gentle. Soon enough he was getting up to fuck me in doggie while the toy was in my ass still. He pulled it out and shoved his dick into my ass. He started going fast just like he always does in my pussy & I was wincing in pain. He suddenly shoved the toy in my pussy while still fucking my ass and I realized it made the pain go away, suddenly I was actually enjoying hard rough anal. A few minutes later I squirted and he was so proud because he knows I usually can’t stand anything in my ass.