So yeah.
I had played with a plug a few times before and liked it, so when a guy I was seeing kept pressing for anal I eventually agreed. He took me out for two fancy drinks and then I took him home. The bed was set, lube and a towel laid out for the deed, and he slipped my clothes off and found my plug firmly in.
I sucked him off for a few minutes and then he pushed me onto the bed and rolled me over. I was wearing crotchless fishnets and he carefully un-plugged me. I was really wet and really anxious by now, but he lubed up and then skipped right into my butthole. I whimpered but it didn’t really hurt, I just felt kind of … full and a little pressure on the “wall” between my ass and VJ. It didn’t really feel good or bad at first but after a little bit I realized I was getting really wet and starting to enjoy it. As I relaxed and he started to push deeper and harder I could feel a little pressure like I needed to pee when he went deep.