Sissy Punishment Novels & Stories

Something they could no longer ignore. The moment before—the one suspended between desire and action, between restraint and surrender—was over. And what came next… would not be quiet.

“Ass up.” Sophia arched her back, presenting herself. The first sharp smack of his large palm on her ass made her cry out. He spanked her hard — left cheek, right cheek, then again and again until her pale skin glowed bright red and she was whimpering, grinding her soaked pussy against nothing. “You like being punished, don’t you?” Another hard smack. “Answer me.” “Yes, Master! I love it— please—”

"Not at all, babe. I just know that sometimes you like being treated like a nasty, naughty slut. And I can do that because... why?" Sabrina licked her lips and stared horny heat at you. "Because I'm your nasty, naughty slut." You slapped her exposed thigh, the loud clap of the paddle on her skin strangely satisfying. "Yes, you are." You gave her a few more slaps with the paddle on her thighs, leaving them a soft pink but nothing worse, then closed her legs around the dildo and tilted them up and back, slapping the underside of her thighs as well until they were the same shade. The dildo fell out on the last slap.

Instead, he swept everything from the desk—folders, keys, pens, and other items clattering to the floor, filling the room with noise. Nick pulled the leather belt from his pants. “Now go to the desk and bend over.” On wobbly legs, I obeyed, pressing my chest against the cold surface. "Spread your legs wider, show me your little pink pussy." He commanded and I did what he asked. "I love how you look now, your tight pussy on full display for your daddy to enjoy it. But you still have to be punished. You disappointed me today. " He said huskily, brushing my entrance with his finger and stepping again away.

When I feel warm liquid streaking down my thighs, I feel so terrible for taking pleasure in a severe situation. "Hmm! You find this hot, huh? Look at you, your little pink pussy glistening," he mutters and I close my eyes fighting back my feelings. Then, Sin's fingers push into my wet pussy, rubbing my sex softly, I cry out, pushing my ass back, fighting for any kind of friction. "You have been a bad girl, Summer," he states and I nod my head. "Punish me, Mr. Sin. I have been a bad girl," I tell him as he flicks my clit, causing me to jolt.

She whispered, “You said as a punishment you’ll let him fûck me.” I did. And I might’ve even done it in the past. But now even the thought of that makes me want to hurt the most trusted man in my life. I pinched her nîpple and she gasped, her pûssy tightening around my côck. “Would you like that punishment, little slût?” She bit down on her bottom lip and I said, “If you like it how would it be a punishment?” I slipped my hand down to where we were joined and used my thumb to circle her clît. I said, “Maybe, I will punish you by making you take both our côcks in that tight pûssy.”

The head bumped my clit over and over, making my thighs shake. “You want this big cock, baby girl?” he taunted, pressing the head right against my entrance but refusing to sink in. “You want your boyfriend’s dad to stretch this cheating little pussy open?” “Yes!” I cried, trying to push back onto him. “Please, Jeremy—I need it. I need you to fuck me hard.” He pulled back again, slapping my pussy with his heavy cock once more. “No. You’re going to take your punishment like a good girl first. Bad girls who squirt without permission don’t get fucked right away. They get teased. They get reminded who’s in charge.”

"I'm going to punish you like the little slut you are." I rubbed my hand over her fishnet clad legs as she moaned out, "I'm such a dirty little slut. Daddy please punish my ass like a little slut deserves." I pushed one more bead in, and without warning gave her two sharp smacks on the ass with the paddle- whack whack. I heard her gasp, and quickly shoved another bead in. She started writhing as I gave her a succession of blows on each cheek, one after the other. I paused long enough to push in another bead.

“ S-Sir…please?” When I heard Lauren’s plead that is when I was taken back from my thinking. I didn’t expect her to be crying and I had a moment of amnesia when I saw my hand caressing her inner thighs in a softest way that is possible. Like a boy in love with his girl, easing her pain. “ Next time that you disobey me…. I am going to bound you in the tree outside so anyone from your class can fill up your filthy holes.” She stuttered an imminent amount of protest then produce a long sensual moan when my hand leave her body. I made her wear an skirts and throw the pants that she is wearing, completely tearing it in front of her as a remembrance of the punishment.

He prodded my asshole with his fingertip, while his other hand pressed against my upper back and held me down on the table. "Fuçk me harder, please, harder, sir!" I pleaded. He pulled his fingers out of my asshole and spanked my ass cheek real hard. "Shut up!" he growled. "This is your price for failing my subject." "Ye.. yes sir... ooohhhh." My eyes rolled to the back of my head and my words stuck in my throat as he increased his pace, he slammed faster and deeper and harder with his balls slapping my clitoris.