We’d been going back and forth about it for months: I’d gotten it into my head that I wanted to have my first flogging, and I wanted it to be a good one. I’d made it to nearly fifty without being flogged and there was only one person I could think of getting it from. My friend Stan.
Stan is what I’d have to call the über top. The first time I heard of him was when a pain pig bottom friend of mine, the guy who provoked the first flowering of my own sadism, talked about the only other man he’d let “do anything, just anything” to him. Stan was that man. I heard about him for months before I met him and then once I met him I knew the reports were not bullshit: Stan has what I look for in a top: looks, grace, humor and heft. By which I mean that his authority is palpable, so much so that he rarely needs to assert it. He walks into a situation and people look to him to direct what’s going on. The first time we ever got together sexually there was no question in my mind but that I should be seated at his feet, nuzzling his boots, eagerly awaiting what ever his cruel, subtle mind had cooked up for me.
Over the years Stan has intoduced me to any number of pleasures (he’s a great researcher), and he became the first person that I could confess any fantasy to without fear of judgement or recoil. In fact, every I told him about some kink I thought was hot, I would usually receive several images of it, or links to websites for it the next day. Much of what I do now in bed or out of it is directly due to Stan’s encouragement and guidance. A couple of months I was talking to him on the phone while he was at a Leather Swap Meet and he picked out something for me saying “I know you’ll like this” without telling me what this was. It turned out to be one of the meanest rubber paddles I’ve ever hefted and absolutely love to use it on people. He was right once again. So of course he was the logical one to beat the crap out of me. I just made him promise that he wouldn’t use any rubber floggers
Our only trouble was timing: between one thing and another, our schedules and the spacial restrictions of New York City apartments we couldn’t seem to come up with the right moment. Then we were both invited to a mutual friend’s country house for the weekend. The friend was going to be hosting a fetish party, most of it out doors, so we knew there’d be room to swing the floggers.
As the weekend approached I grew antsy. I like pain and I’d been hit with a lot of things, so that wasn’t what was getting to me. Finally I realized that I wanted to be a good enough bottom. We’d waited so long that the scene was taking on that oh god what if something goes wrong vibe. What if I couldn’t take enough? Stan always has that effect on me. I had to just put it out of my mind, and reassure myself that whatever happened would be fine.
When we finally got to the event, there was a big St. Andrew’s cross set up on the patio and a lot of guys milling around the house drinking beers, looking to get up their courage. The weather had turned chilly so we decided that even though it was still fairly early we had better get right to it rather than wait and have it get colder. I was in my NY Sanitation uniform, smoking a cigar. Stan gestured to his toy bag, and I carried it over to the cross, pulling out a few ropes . He stripped off my shirt and positioned me in front of the cross, swiftly tying my wrists to the uprights. He reached in front of me, plucked the cigar out of my mouth and brought its glowing tip close to my nipple. I began to relax into the heat and the bondage while Stan continued to work my nipples with the cigar and his gloved fingers. Soon he had me grunting and rubbing against the cross.
At that point he stepped back and I braced myself for the first blow. But when it came, it was a caress. Stan brushed the tails of the flogger across my back, easily, flicking back and forth. It was maddening. “Fucking Sadists” I thought, “always torturing!” At that moment the flogger thudded hard across my back, shoving me into the wood. Warm up was over; Stan laid into me, building stroke on stroke. The heat spread across my back and I began breathing into the pain, surfing the rising wave of endorphins. It felt so right to be hit again and again. This was what I had been waiting for! He paused for a second.
And then I heard a strange jingling noise behind me.
The next thing to hit my back wasn’t warm like leather, it was cold metal. I jumped in surprise and then Stan was right behind me, chuckling “You said no rubber, but you never said anything about chain”. That was when he started working me over with a short cat that ended in five light steel chain tails, each tipped with a short leather tongue.
By this point we had drawn a bit of a crowd, even though I was largely oblivious to it. The only things going on in my mind were the bite of the chains and the electric spark of each stroke. I began to yell at each hit, growling and shouting my way through the pain. I was back at animal level, dragging air into my lungs, hanging from the ropes, moving my back out to meet the flail.
Finally Stan began to slow down and I could feel my own pleasure cresting. I was light headed, beyond words, and when he asked me if I wanted to be untied, all I could do was nod. A couple of minutes later I was sitting inside with a bottle of water, grinning stupidly as my back throbbed. I slid to the floor, wrapped my arms around Stan’s boots and thanked him for being such a good freind. He handed me a cigar and told me not to mention it.