It had been a good session so far. I’m very into arse work and Derek was one of the best I knew at it. With some tops it’s just a question of piling it on with paddles, whips, or canes before fucking me blind but Derek really seemed to understood how things work better than most.
I’m not actually into pain as such, at least not the way most guys apply it, but every time I had a session with Derek he would expand my horizons in some way; and many of those ways included pain. But the way he did it, encouraging the endorphins to build up at the same time, meant that although I was often at the edge of not being able to take it, I always could - just. And fuck, was it good.
In this session he’d spent a long time using a single small paddle on me in his hands it was capable of everything from the lightest, teasing touch, to an unbearably painful sting that made me yell, and my eyes water. He had me restrained bent forward over a bar between two vertical posts, my hands inside thick leather fingerless mitts and cuffed to a board that sloped down to the floor beyond. I was hooded, and my ankles were cuffed to the bottom of the posts. A wide leather strap over my pelvis kept me from moving to avoid anything, and the bar kept my cock pointing downwards. It had been hard and dripping precum for ages.
This time he’d setlled into a cycle: he’d work on my arse cheeks, first one and then the other, using the paddle with slowly increasing force over the period of a minute or so until my face was screwed up and I was on the verge of screaming for him to stop but at that point he would stop. How did he know? I had no idea. Then he’d stroke my reddened skin lightly hardly touching with his leather-gloved fingertips. Carressing, soothing, teasing. My cheeks, sensitised beyond reason by the paddle, would respond with what felt like a golden glow. It was beautiful. After a couple of minutes of this, he’d start lightly with the paddle again. Each time he took me further, and each time it was more heavenly.
Then he did something he’d never done before and which I’d never experienced before in my life: he parted my cheeks with the thumb and fingers of one hand, exposing my hole, and started to beat it with something very thin a small cane, I suppose, or something like that. He was accurate: the cane struck directly on my arsehole it never once touched the sides of my cheeks. Fast, light strokes at first, but soon getting slower and harder. He must have positioned his hand very carefully because not once did it make contact with my coccyx.
The feeling was new to me and it was intense as, I discovered, the arsehole is very sensitive indeed - at first I worried that I wasn’t going to be able to take it for long but I should have had more trust in him; he knew exactly what he was doing. The pain began to build; a much more acute and specific pain than the paddle on my cheeks had produced, and soon I was on that verge again, ready to yell. But then it stopped getting any worse. Derek kept it at that intensity for several minutes, and I found that I was riding on a cloud of endorphins that felt amazing. It felt like I was flying.
Some part of my mind realised that I needed very badly to cum, but every bit of my concentration was being forced onto what he was doing to my hole.
Eventually he stopped, and began to tease the rim of my arsehole with his fingertips. That was un-fucking-believable. I was moaning inside the leather hood, and moving my body sensuously in my restraints, loving every moment.
We’d been at it for a few hours so far, and when he stopped and patted my bum I assumed that was the end of the session. Sometimes he made me cum, sometimes he didn’t. I waited for him either to wank me off, or to release me. He did neither.
I heard him moving about in the playroom, and wondered what he was doing. Then I felt him take up position again by my arse. More paddling? I wondered. It was a while before anything happened, but when it did I screamed. It was partly the unexpectedness, and partly the tiny but intense pains that I suddenly felt.
It was like pinpricks at first, but then each one seemed to grow and and to evolve somehow into a different kind of pain. More came. They were all over my arse cheeks now, and he was slowly getting closer to my arsehole.
When his fingers parted my cheeks again I shook my head in fear. No. Whatever it was, I was not going to be able to take it there. But he ignored my protesting body language and then I felt the most intense pain sting the already sensitised rim of my hole. I yelled I couldn’t stop myself. Then I realised exactly what it was: stinging nettles.
He was making soothing noises, but he continued to stroke the evil leaves over my arsehole. And then the endorphins started to do their thing again. The pain was still there, still every bit as acute, but now those wonderful chemicals in my brain were overlaying a feeling of intense pleasure on it. My entire arse was on fire beautiful, hot, glowing fire and it felt like there was a halo around my hole.
He stood up. I continued to burn with pleasure.
Then I felt his fingers gently close around my rigid cock. No! If he makes me cum now, I thought, it will be fucking unbearable afterwards. But his hand didn’t start to wank me. Instead it carefully pulled my cock further back and held it there by the base. A new, dreadful possibility occurred to me but before I could begin to protest I felt it: something soft dabbing repeatedly and slowly right on the tip of my cock head and leaving excruciating points of pain in its wake. His hand pressed the leaf very carefully onto my piss-slit, then lifted, changed angle a tiny bit, and did it again. He even put several stings onto the inside walls of the slit itself. I was yelling and struggling fit to bust. When he was satisfied that he’d nettled the slit completely, he put a concentrated ring of stings around it, on the very end of the bare glans. He didn’t touch the rest of my cock head.
He left me there for a few minutes, while I squirmed and moaned, and then I felt his hands undoing the hood. When he’d released me from the restraints I collapsed on the floor. He stood there smiling down at me. I didn’t know whether I wanted to beat him to a pulp or hug him.
“The acute pain is already subsiding,” he said. “In a few minutes it’ll be a warm itch. Histamines and acetylcholine injected into you by the little hairs, which are actually hypodermic needles. Fascinating, don’t you think? That’s what does the business.”
I was not able to concentrate on a chemistry lesson at that point, I’m afraid.
He passed me my jeans, and I turned them over in my hand looking for my underpants. They weren’t there.
He smiled again. “No underpants today. I’ll give them back to you next time.”
I looked up at him, frowning, but then I nodded in resignation. Knowing him as I did, I should have expected nothing less. The bastard was making sure that there would be nothing between those stings and the rough denim of my jeans.
It felt strange to wear tight jeans with no pants. My cock was still fairly hard I still needed to cum and as I tucked it into them and pulled the zip up I could feel the denim moving over my cock. Strange, but interesting. Slutty, somehow, I thought.
I don’t drive, so I use the train when I visit Derek. The carriage was crowded with commuters, and I didn’t manage to get a seat. As I hung from a strap more people filled the train. The doors closed and it began to move.
Usually I like travelling by train I find the rhythmic swaying restful but not today. I was continuously and acutely aware of my cock, and each movement of the carriage caused my jeans to brush over my nettled arse and cock head, and I was getting a hard-on again. It felt like there were tiny fingertips teasing it under my jeans, and there was no way I could get away from it. There was nothing I could do about it I tried thinking of the most un-sexy things possible, but it made not the slightest difference. A blond teenage boy with a skateboard was standing next to me, looking down at my crotch, and my face began to redden as I realised he could see the growing erection in my tight jeans. I tried to turn away from him but there just wasn’t room, and wherever I moved he still had an excellent view. I couldn’t even get my hand down to cover it.
The nettle stings were not exactly pain any more. I actually couldn’t feel the ones on my arse very much (those right on the hole were a bit more noticeable) but the tip of my cock head was tingling and buzzing and demanding attention. And every little movement made it worse; my cock got harder still. I thought about re-positioning it, but was afraid that even the touch of my own hand would make me cum apart from the facts that there was nowhere I could put it where things would be any better, and with the press of bodies around me I couldn’t get my hand to it anyway.
I was biting my lip, fighting to control myself. I’m not into teenage skateboarders but at that moment even the thought of that one seeing me shoot my load uncontrollably was turning me on. I was on the edge of cumming and there was not a single thing I could do about it and that damned boy would not take his fucking eyes off the bulge in my jeans.
We went over a set of points, and I lost it. It’s a strange thing: when a guy is right on the point of cumming, everything else ceases to matter. Suddenly I couldn’t give a shit what anybody saw, or what anybody thought. Even the humiliation and I’m not usually into humiliation was indescribably horny. My spunk jetted out of my cock - and it was one of the most amazing orgasms ever: as the spunk shot out it seemed to re-energise every one of the stings in and around around the slit, and they made it unbelievably fucking intense. My knees buckled but the press of bodies around me kept me upright. The skateboarder’s mouth dropped open as my cock bulge visibly throbbed in my tight jeans and a dark, wet stain quickly grew at my crotch. His eyes lifted to mine and I realised I was looking at him directly. What on earth must he have thought? I wondered. His hand went to cover his own crotch but not before I’d seen that he had an erection too in his shorts.
When my orgasm subsided the full weight of humiliation now not horny at all descended on me, and the stings went back to being pure pain.
Thankfully the next stop was mine. Avoiding the skateboarder’s eyes, I fought my way out of the train and stood breathing hard on the platform. The next time I saw Derek, I intended to kill him. I laughed. He was a bastard I bet he’d known exactly what would happen.
“Want to come back to my place?” The voice was soft, boyish.
I looked over my shoulder. The skateboarder was stood behind me. I turned round. A good-looking boy, but far too young for me. I smiled. “Thanks, but I’m afraid not.”
He looked disappointed, but then he nodded, lowered his board and rolled off.
I watched him disappear into the station, and then realised that people were looking at my crotch as they passed. I lowered my eyes and saw the huge wet patch. Time to make a hasty exit, I thought. My cock was getting hard once more and the nettle stings were becoming worryingly pleasurable again.
‘Sado-botany’. I’d heard the expression, but until now now I’d had no idea exactly what it meant.
In the next few days, I thought, I might possibly do a little gardening.