I was in Chicago on business and met a daddy bear type named Dan at a bar. He took me to his house and we had dinner, and then afterward, he told me I was going to get spanked. He bent me over his lap and hand spanked me on my jeans, and then pulled them down and smacked my brief clad hiney as hard as he could. Eventually he pulled my briefs down and walloped my naked ass with his hand over and over again. My butt was burning but that was just the warm up of course. He stood me up and stripped me buck naked, and then led me downstairs by the ear. He stripped to his briefs himself and then made me bend over and place my hands on the seat of the couch in his tv room. He proceeded to bust my ass with every paddle he owned. Small wood ones. Large leather ones and everything in between. My ass was on fire. Then he pulled out a lexan paddle and a steel paddle and began to give me swats with each. I'd never felt pain like that in my life and stood up on my bare toes, wriggling and trying to avoid the stinging spanks. He wrapped his arm around my midsection and I could feel his erect cock through his briefs as he beat my nude asscheeks as hard as he could. By the time it was over, we were both out of breath and my buttocks were black and blue. He sat on the couch and I proceeded to suck his daddy dick until he shot his hot cream in my mouth.
The next day I fucked him in his sling and ate his asshole, but that's another story for a different site altogether :)