Spanked With Ruler Novels & Stories

The pain in my scalp mixes with the heat between my legs in the most delicious way. After hitting me ten times with the ruler, he rubs it between my thighs, making my breath heavy. I close my eyes, press my face down on the desk, and lose myself in his sweet torture. As I do this, my feet lift into the air because the end of the rope is tied to my ankles. Damn, this tied-up position is so intense. “Are you dripping wet from getting tied up and spanked like a disobedient little professor?” He asks, rubbing my clit with the ruler, driving me crazy.

The ruler run up the inside of my left thigh until the width tapped gently against my bare, exposed, soaked pussy. Oh no! I was about to speak when the ruler pulled back quickly. THWACK!! It hit, hard, directly onto my bare pussy. "FFUUUUCCKKK!!" I shouted. "You didn't do as you were told, so that doesn't count." He told me and gently tapped my pussy with the ruler. I could hear and feel my wetness coating the ruler as some strange pleasure coursed through my body. And then... THWACK! He slapped my pussy directly with the ruler again.

The searing heat of it had me gasping. "Drifting in the class and not concentrating is not allowed." He swung the ruler again. I hissed out a breath as it struck a new spot. "What do you say to that,?" he asked, striking again. The sting was sharp and hot, but not overly painful. In fact, it only made me wetter. He had to be able to see the effects the spanking was having on me. He dropped the ruler onto the desk with a clatter. This time, when he spanked me, it was with his bare hard hand.

My grip tightened around the gun, my knuckles turning white. Lina suddenly leaned out from behind him, her voice sickly sweet. “Consigliere, if you’re so attached to this place, you’re welcome to visit anytime. When Drake and I have another child, they’ll call you–” Before she could finish her sentence, I slapped her hard across the face. The force sent her crashing into the dirt, one side of her face swelling almost instantly. Silence fell over the entire site. Drake’s expression changed sharply. He rushed forward and grabbed my wrist.

"Yeah, just give her a few whacks with this. She can tell you to stop if she wants to." Of course the guy never knew that I couldn't "just" say stop. I could, but it would mean stopping a lot more than just a few hits with a ruler. And I did get kind of turned on. OK, a lot turned on. I stayed there, bent at the waist, because I knew if I rose without direct orders I'd get a real whipping later. I'm sure my pink, puffy slit was on gorgeous display as the client hit me again and again with the ruler. I could feel myself starting to cum, and Master Oliver could tell, too.

Catherine said, turning her head to speak to him. “I’m Sir to you, not professor. The second rule is no talking. Now I’m going to have to spank you harder.” Before she could protest, down cane the ruler on her ass in three quick successions. She knew for a fact that her butt would be super red at that point, especially after being hit with a ruler. Catherine felt it as he expertly slipped her panties down to her ankles, sliding them off one leg, to leave them dangling on the other.

His tongue speared deep, lapping her walls with sloppy fervor, the wet schlick echoing. She rocked, clit bumping his nose, juices coating his chin in glossy sheen. But when his hips bucked, cock seeking friction, she snatched the ruler and cracked it across his ass cheek stinging crack, flesh blooming red instantly. "Don't you dare touch yourself. Edge for me."

The pain was sharp, but it mixed with the throbbing in my clit, making me even wetter. He set the whip aside and picked up a small wooden ruler. He brought it down hard on my pussy. The flat edge smacked my swollen lips, the sting exploding across my sensitive flesh. I screamed again, my body jerking against the ropes. He spanked my pussy over and over, the ruler landing on my lips, my clit, the tender skin between. Each strike made my pussy swell more, turning red and puffy. Tears streamed down my face, but the pain only made me hornier. My clit throbbed, my hole clenched around nothing, desperate for more.

he spat viscously at me. “I won’t, your majesty, I swear it. I won’t go there again.” He stepped back, and turned his back to me. My body started to relax, assuming he was done with me, when, without warning, in a split second, he turned back to me, flung his arm around and grabbed me by my neck. His face was almost touching mine as he looked at me through gritted teeth. “You better hope I find use for you, you pathetic wrench, there better be a prince out there that’s willing to marry you, or I’ll ship you off on the next boat as a fucking slave!”

His jaw was clenched so hard his knuckles turned white against his desk. I turned my attention back to our teacher, whose eyes were practically burning holes through me. She slammed her palms flat onto the desk. "Watch your mouth, Miss Flynn," she warned, her voice laced with venom. "I'm just joking, Ma'am. I'm sure someone as prim, proper, and professional as you would never do something like that," I deadpanned sarcastically. I shifted my gaze down to the guy sitting in front of me, practically vibrating with restrained rage.