First time having anal sex and it was at work with my boss
I was 20 and working at a mobile phone store. The manager was a old perv, he seemed somewhat normal but was always making crazy remarks about the customers after they left. It was long before he started talking dirty to me about what he likes. At first I was like chill dude but it just became normal and I would listen and laugh. He came into work one day and he was like man I’m so fucking horny today I’d lick your ass. I was like wtf, I said you lick ass? He said hell yeah. Then he asked me a few hours later, so you going to let me link your ass? I never even thought about being with a guy and I wasn’t then. End of the day after we closed he said come on man let me lick your ass. I told him I doubt you’ll lick me ass lol. He said show it to me. Jokingly I turned around and bent over and mooned him. As I was pulling my shorts back up he grabbed them with 2 fingers right by my Crack, I felt his fingers touch my cracked. He tried to pull them back down as I pulled back up. He got on his knees never letting go of my shorts and kept pulling. He got them down about 3 inches and quickly started licking the top of my ass Crack. I struggled a little more then let him pull them down. He didn’t say anything, he immediately took a long deep lick from the bottom of my Crack to the top. Then he started locking my hole. It felt real good, I liked it a lot. After about 10 minutes of licking my ass he stood up and said you have to let me fuck you. I said no fucking way. He kept lick and begging. He stood up and said I’m just going to rub my dick on your ass since it’s so wet. I let him. I felt his dick slid between my cheeks and touch my hole. That felt great, he kept doing that until he suddenly try to push it in. I pushed back a little but he had the head in and came instantly. Once I felt the hot cum and he was no longer pushing I let him leave it in as he finished pumping his cum in me. He cleaned me up and now we do that every now and then.