I stood naked, apart from a leather belt, facing the whipping bench in the dungeon. The door at the top of the stairs was half open and the sunlight lit the side of his boots as he came down the steps. I liked to see that black leather shine, especially as I put it there. I quickly lowered my gaze and waited. No shackles, no rope. This time he simply pushed me over the side of the bench and told me to grasp the legs as he kicked mine further apart. I waited for the lash. It's the same feeling you get when you think someone is watching you but you don't know for certain, a sort of itch at the back of your neck. Well this time the itch was in my arse and I felt my cheeks clench and unclench as I looked at the concrete.
Several seconds later all I felt was a lubed latex finger rubbing round my hole before the pressure increased enough to part my sphincter and fully enter me. My eyes closed with the pleasure the feeling brought. His finger played with my prostate sending rivers of electricity up and down my thighs until he slowly withdrew to a quiet whimper from me. A drop of precum glistened as it very slowly oozed from my cock.
I felt one of his hands reach over my back and hold my shoulder, pulling it back slightly, as at the same time a new pressure was put on my hole. Cold and harder than a finger it pushed it's way slowly into me. I felt Sir pushing the plug in whilst pulling me back from sliding over the bench. It started to hurt as the diameter grew and forced my muscles apart. I waited for that pleasant moment they could close over the neck of the plug, securing it inside me but at least not stretching me further. I cried out as the pain increased. He let go of my shoulder and slapped my face, no words, I knew. More pressure brought tears to my eyes, I clenched my teeth trying not to protest further but felt the sound rise in my throat. He had his feet inside my ankles now as I automatically tried to bring my legs together, more pressure on my shoulder kept me from struggling. My hole felt like it was being pulled apart. The pain was red hot, it went up my spine like a spear. Just as I was about to scream he pulled me upright. Breathless I stood, legs apart and slightly bent. He held the plug in place with one hand and pulled on the leather straps that were attached to it up to my belt where they clipped on to the studs already there.
"That's not going anywhere in a hurry" he said sternly.
I felt round my backside. The plug was new, at least it hadn't been in me before. It must have been the shape of a traffic cone and felt twice as big, there was no "nice" neck for me to grasp and relax on. The neck was the widest part and it made me ache like nothing else. I felt like I was about to take a dump whilst the top must have been several inches inside me and rubbing on the same sweet spot that his finger had found only minutes before. Simply moving my weight on my legs made that feeling rise in my thighs, walking would be an assortment of pain and cock hardening eroticism.
He turned back to me and gave me a pair of leather shorts, not my usual ones. These were also new to me. Thicker, they had straps and buckles around the bottom of each leg as well as the waist. The front was a double zipped pouch which ended under that wide waist belt. I soon realised they were chastity shorts and I was about to be locked into them. When I had pulled them up to my waist he pulled each strap tight and locked each buckle with a small padlock which snapped shut in a very final sort of way. He pulled my cock down inside the pouch, it was still semi erect, and zipped it up, closing each one under the belt before locking that too.
I was plugged, quite hard now and still had that combination of arse ache and being fucked feeling.
"Ok boi, off you go. Lawn needs a bloody good mow. You know where everything is, I'll be up in a minute."
I knew where everything was all-right. The mower was a cylinder push mower with a 16 inch cut. The blades were as sharp as razors but he kept the mechanism dry and ever so slightly rusty. This meant I had to push hard to even start it moving, but at least it didn't harm his precious lawn. Once out of the shed you could see it was like any other rather dated mower apart from the handles. They had been adapted with a cross bar and a pair of shackles that were riveted in place. Once you held on to the handles these were locked on around your wrists. They were about 2 inches wide and a quarter of an inch thick making it difficult to bend the wrist, you simply had to keep pushing with you arms held in one position.
I knew the drill, I snapped the left one over my wrist and waited for him to come and do the same with my right. When he had done that, all the time telling me the usual things about how straight I had to make the lines and not to go too close to the edges, he gave me a thorough rubbing all over with sun screen. The one and only time he had forgotten that I burnt my back and shoulders, which he was then unable to whip for over a week. Actually he tried it but the skin split with the first stroke, I collapsed screaming and he put me to bed where I stayed for the rest of the day.
Glistening from the lotion I started to push. The plug made itself known immediately. As I made my way up and down the lawn each step shot charges up and down my legs. I had to bend slightly forward which made the point of the plug stroke my prostate which in turn gave me a hard on which in turn rubbed against the inside leather of the shorts, it was a blur of pleasure and pain. The blur ended when he shouted at me. I'd strayed off the straight and narrow, at least the straight and green, and he stood at the top of the garden pulling the single tailed whip through leather gloved fingers. I now had to slowly push the mower back up the lawn towards him knowing that when we met I'd get a stroke of the plaited leather tail. Each excruciating step drew that particular pain closer. I got to the top, turned and started to mow the next stripe. I knew what he would do, he was an expert in this. Too close and the whip would hit me full on but with very little speed. Too far and he'd miss altogether. The right distance was where my shoulders would be within about 6 inches of the tail when extended from his arm. It would crack on my skin with the maximum speed and efficiency, leaving a line where small pin pricks of blood would ooze from the surface and mix with the oily sweat. It looked worse than it was although the pain seared through me with no less effect.
It was like a bolt of electricity when it hit. I yelled but dared not stop. I desperately wanted to rub my forehead, to straighten my back, to wipe my eyes which were tearful from the whip but carried on mowing. One stripe was enough for now.