He looked up at me, his eyes seemingly more piercing blue than I’d noticed before. Perhaps it was the desperation making his eyes shine more brightly. He murmured something. If he was begging to be set free, I couldn’t understand him due to the gag in his mouth. He’d made me so wet earlier just by kissing my neck, so I’d fastened my panties snugly in his mouth. I knew the taste would make him desperate for me, and it seemed to be working. He murmured something again.
“Are you begging for more?”
He nodded yes.
“Oh I’m sorry, I didn’t hear you. Say, ‘More please, Miss Molly.’” I teased.
Four muffled words barely escaped his mouth before I struck him across the face. “That’s better. Maybe next time you’ll do better to remember your manners,” I chided. I believe the next thing he attempted to say was, “Yes, Miss Molly.”
Before allowing him more of the pain he desired, I stood back to take it all in. He looked so sweet and helpless there, kneeling with his wrists bound above his head. The rope from his wrists was strung through a pulley hanging from the ceiling, with the other end tied around his cock and balls together. The idea was that he’d do most of his own torture – if he began to lower his hands or sit down on his heels, he’d feel the pleasantly unpleasant tug on his cock. This had happened several times already, as he’d begun to weaken with each blow. This is why I was allowing him a short respite before the ‘more’ he’d been begging for.
I knew that my standing there observing him was some of the worst torture I could give him. In addition to the anticipation of the impending pain, the idea of me just looking at his naked body was difficult for him. I adore the sight of him, though. His dark hair, still ruffled from me tugging on it earlier, his beautiful eyes that looked at me so pleadingly I almost gave in, his torso, trim and covered in tattoos that made him look all the more exciting, his back, red and marked from what was now nearly an hour of punishment, and his small but perky ass, which was reddened already but was my next target nonetheless.
I selected the riding crop and plucked it from the pile of equipment on the table next to me. I dragged it across his shoulders, then across his chest, down his spine, between his legs. Every time I picked the crop up off his skin, I could see him brace himself for its impact. I loved toying with him like this. It almost made me want to tease him forever and never actually strike, but the snap of the crop on his bare skin was too tempting. Additionally, if I teased him long enough, he’d stop bracing himself for impact, expecting only more teasing. But his fear of the pain is essential, so just when I could see him begin to relax into the teasing – SNAP. I struck him on his left butt cheek. It was loud, but not particularly hard. Just enough to remind him of the reality of the pain. Just enough to bring him back to the present and keep him from drifting away. Just enough to ensure his attention was on me. I dragged the crop across both his cheeks again. When I lifted it off his skin, I saw him tense once more. Excellent, I thought. This was exactly what I wanted. I hovered the crop off of his skin for just a moment, and then dragged it down his spine again. I wasn’t sure if he enjoyed the sensation of the crop dragging across his skin, but I didn’t really care. It was all part of my fun.
I dragged it up and down his back, and then without giving him a chance to steel himself for the blow, I cracked the crop against his right butt cheek. He winced with pain, and giving him no time to recover, I hit the left and then the right one again in quick succession, slightly harder this time. I watched him squirm, both physically and mentally. I could almost hear his inner dialogue begging him to ask me to stop and also begging me to continue. I circled him now, dragging the crop around his torso, the steady clack of my heels against the hard floor. I wondered for a moment if his knees hurt more than the blow of the crop. I couldn’t have that. I circled him once more, tapping his nipples lightly with the crop. Watching him discover how sensitive his nipples are has been a particular delight for me lately. When I was behind him again, I let the crop pause on his right cheek. I waited. I felt his whole body begin to tense, anticipating the pain of another blow. I lifted the crop away and watched him visibly tense further. Not yet, I thought, and began to make another lap around him.
—
After maybe 10 more hits to his ass, I could tell he was beginning to weaken. His arms drooped ever so slightly, and I saw the rope pull at his cock. He flinched and re-adjusted. I watched him writhing as he tried to find the balance between letting his hands lower as much as he could and keeping the rope from tugging more than he could bear. This is a particular pleasure for me – watching him do his best to endure the situation I’ve put him in. He was trying so hard to be a good boy for me, but I could tell my love needed me to release him soon.
Source: reddit.com/r/Erotica/comments/c5otl0/simple_machines_f_femdom