My First Flogging

B first contacted me on Recon. We had a lot in common, he described himself as a top bear perv, and one that enjoyed a little abuse and kinky play. I said “hi” back and we got to chatting.

What he’s really into, it turns out, is just being a selfish brute (in a good way). A little beating, a little flogging, a lotta roughness. He was also artsy, and enjoyed movies and good television. He was an all-around well-versed, nice guy. In the bedroom (or where ever), it was all about him as a Dom Top, and he didn’t even care if his sub got off. He enjoyed it rough – leather, a good beating, some scratching, a lot of nipple play, and flogging. I was a little intrigued, a little scared, and a lotta hooked. I knew I could into serving this guy.

He suggested a meet before a session, which very much puts me at ease and is something I prefer all the time – for friendship, for vanilla hookups, for whatever. We ended up at Barracuda – a popular enough gay bar ’round here that on the night in question, was almost empty.

We sat and chatted and drank. We chatted about all sorts of things from TV to life-stories. As I drank more scotch and he drank more vodka, I moved over next to him because as loud as the music was I could barely hear him. Our positioning worked out that I had to put my arm around him. When I got back from a bathroom trip, he repositioned so his would be around me (the proper place for a boy). The rest of that night his hand worked his way into my shirt, mine over his cock. He pinched and flicked and tortured my nipple so much it was bruised and was super sensitive to the lightest touch later. He scratched my back so hard I thought he’d cut points into his finger nails. I was drunk, and happy, and having a good time.

Soon after we arranged a late afternoon meet at his place in Jersey City. I was nervous as all hell. We didn’t really have a plan; I knew we’d try flogging primarily. That was something I’d never done, and something he was happy to introduce to me, along with the requisite rough and tumble.  When I arrived I was almost jittery. He told me to put my stuff anywhere. I wasn’t sure if he meant my backback or my clothes too. Just my backpack … I just needed to relax a bit.

We chatted, he gave me a tour of his place, we sat down on the bed and chatted a little more. He told me to go ahead and take my clothes off. I did and he changed into a pair of leather chaps that outlined his jockstrap well. Later I found he also had his Prince Albert in and a nice metal cock ring on. He put a collar and heavy metal leash around my neck where it stayed for the rest of the session.  Our time had begun, and I was ready to serve. He had me lick his boots. He had me suck and slobber on his cock still in its jock. He spat on me and in my mouth. He tortured my nipples again so, so very hard.

He put me down on my knees and gagged me on his monstrous cock. It was a nice, veiny cock of way-above-average girth. It felt like a soda can. Fucking wasn’t on the agenda but I knew I wouldn’t have been able to handle it. He gagged me, he pulled back. He beat my chest and back until I nearly collapsed. He attached an alligator clip to my nipple and the other end to his, and then pulled. I cried out in pain. He knew when to relax the pressure and when to dial it up again.

But the capstone was the flogging, which took place somewhere in the midst of all the rough stuff. Before meeting B, I never imagined I would enjoy being flogged. I knew it was something I’d probably have to try, and God knows I enjoy the porn, but to actually do it was another thing entirely.  I didn’t know what my limit was, I didn’t know what to expect. I never thought I had a high pain tolerance, and to willingly get flogged or whipped … just seemed crazy. I pretty much thought flogging wasn’t for me.

He showed me all the different kind of floggers he owns (and he has a ton) – paddles, soft ones, long ones, short ones, cat-o-nines, etc and so forth. He had me bent over on his bed, ass towards him, feet on the ground, face in the covers, hands above my head. Then he started in. He used most of his tools, flogging and whipping me with a wide variety, letting me experience it all. Sometimes he spanked me or flogged me and had me count off, “1 Sir, Thank you Sir. 2 Sir, Thank you Sir.” Sometimes he just checked in with how I was doing.

When flogging was done, we went back to the sucking, beating, licking, flicking, scratching, and all around raunchy play until he came. I didn’t. Then we cuddled watching a beautiful animated movie and eating pizza.

During the flogging, I was surprised to find myself enjoying it. Even the memory of it is a warm memory, in a way. I enjoyed myself. Yeah, sometimes it hurt and I didn’t want it anymore. But sometimes it just felt kind of freeing, or at least I could see how it would be. Different floggers, different feelings. The only thing he didn’t have was a single-tail whip or a cane – and that was fine by me! It would be a different experience if I was tied up, or chained to the equipment he had bolted to his doorway, and its an experience I’d be happy to have. I want it to happen again. Who knew? Flogging me be for me after all.

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