14 years ago I posted a couple of stories from my first sexual experience, which…
Leather Punishment
She woke up to the feel of his hands groping her. She was stretched out on her stomach, hands over her head, bound with thick leather cuffs. The cuffs were something she always wore; it naturally was a part of her everyday wardrobe. But she heard a chain jingle and when she attempted to move her arms, found that the chain secured her wrists around a bedpost. She opened her eyes, but the room was dark, a very faint glow from what she assumed was a candle on the other side of the room.
“You’re awake.” His voice was rough in her ear.
“Yes Sir.” She murmured softly.
“Do you know why you are restrained?”
“No Sir.”
“Last night. Do you remember now?”
“I… I came without your permission Sir.” Her voice wavered slightly. It wasn’t intentional, but with the feel of him pounding into her relentlessly, and the intense vibrations on her clit. It had just gone on too long, and she came, screaming and twitching and shaking violently.
“That is correct.” He leaned into her ear and kissed it softly. “Do you believe you deserve punishment?”
“Yes Sir, if it pleases you.” She told him, it was too dark to actually see the details of his face.
“It pleases me very much so.” She felt him dragging the blanket away from her body and shivered at the coolness of the room. It was hot, the middle of summer, and their air conditioner had broken earlier in the week, she was curious how he’d managed to cool the room off so much, but her mind didn’t stay on the thought for long because his hand slapped against her ass, not too hard, but enough to shock her from her own thoughts. “I said get on your knees.”
She nodded quickly, bowing her head. “Sorry Sir.” She pulled her legs up under herself and propped herself up on her elbows. Her pert ass stuck up in the air and he smirked at her.
“Good girl.” Another slap against her ass caused her hips to buck. “Stay still.” He growled at her and heard her take a deep breath. “Now, what do you think would be suitable for doing such a thing? How many slaps against your hot little ass?”
“Fifteen sir?” She closed her eyes tightly, trying to listen to him, to listen to his voice and try to figure out what he was thinking, or planning, or where he was standing.
“Fifteen you say? Well, I think we shall double that today.” She let out a quiet wail. Thirty spanks? A chill ran down her spine. He couldn’t be serious, could he? “And it will not be from my hand.”
“Wh-what do you plan to use Sir?” Her voice was unsteady. Using his hand was one thing, but he planned to use something else in her punishment.
“That my dear, you will just have to wait and find out.” His hand thrummed against her ass again. She listened to him as he moved around the room. What was he doing? Fear had sent it’s cold grip on her spine. She couldn’t move.
“First of all, I have a present for you.”
“A present Sir?”
“Yes.” He smirked and moved back towards the bed. She felt something cold and damp against her anus. And then one of his fingers. Rubbing around the outer ring before slowly pushing inside. A moan tore from her lips and his other hand slapped her ass. “Did I tell you that you could moan?”
“No, Sir, I’m sorry Sir.” One finger became two, gently see-sawing out of her tight sphincter. A third finger was added and he smiled at her sharp intake of breath.
“Are you ready for your gift?”
“Yes sir.” She nodded slowly and felt it pressing against her asshole. Thick soft plastic. He moved it slowly, pushing it in. It stretched her wide. Never had anything penetrated her ass before, and it was causing delicious friction, and shivers ran up and down her spine. The thick plastic grew thicker as it sunk deeper. She began to feel like it would never stop, it would just keep sinking deeper and deeper, stretching her wider and wider until she either came, or died from the excruciating pain/pleasure.
He watched as her ass gripped the plug, he pushed it slowly until just barely an inch was left, then he stopped, pulled his hand back and then slapped her ass hard. His fingers hit the butt plug and it quickly filled her the rest of the way. Her back arched and she cried out.
“Oh fuck! Shit! Fuck!” She cursed loudly, her hips pushing back trying to push the painful invader from her body. Her body quaked. The sensations were amazing. It hurt, but there was a layer of pleasure, just below the pain.
“Shhh.” He hushed her, letting his fingers run up and down her spine. “Good girl. Be quite now.” Her curses subsided to whimpers which after a few short moments dissipated, and she was silent again, except from her harsh breathing.
“Now, your punishment begins.” He moved away from her again and she laid her cheek back down against the blankets. Seconds later she felt the first lick of the small leather whip against her rump. “I would like you to count my dear. All the way to thirty. If you miss one, or loose count we will begin again.”
She nodded quickly, and managed to speak. “One, Sir.” He hit her again. “Two, Sir.” Halfway through she let out a quiet sob. The pain was horrible, but tolerable, but she couldn’t help but cry. “Twenty-nine, Sir.” Her throat was corded with the urge to scream.
Her thick wetness dripped from her pussy, coating her inner thighs in the heady arousal. The final strike came in contact with her bare pussy. Her hips bucked and her whole body jerked. “Thirty, Sir.” Her voice was just barely a whisper. The pain was so powerful. Her head was swimming, she couldn’t see anything all she could hear was a loud static in her ears, and his breathing.
“You handled your punishment well, Love. I think you deserve a reward, what do you think?”
“Yes, please Sir. A reward would be greatly appreciated.” The bed shifted as he climbed up behind her.
“Can you hold out for me this time? Not come until I tell you to?” She nodded quickly.
“Yes Sir. I will obey you sir. ”
“If you don’t we’ll have to go to sixty next time.”
“I will obey you sir!” She cried, not wanting to displease him.
“Good girl, you will come when I tell you to, and not before.” Then without another word he entered her dripping went passage, and began to move quickly, grunting at the feel of her tight pussy gripping his throbbing cock.
He let his hands rub and knead her ass, occasionally slapping his palm against it, causing her to buck. Then he fixed his eyes on the plug. Bright pink, a color that fit her personality so well. He used one hand to grip the base and began to pull it out slowly before pushing it back in.
Her inner walls clenched and she bucked. The reaction pleased him so he repeated it, again and again, until he heard her saying something quietly, over and over. “Speak up Love.”
“Please let me come! Please I want to come!” She threw her head back and pushed her hips into his.
“Not yet.”
“Please!” She wailed. His hips thrust continuously against hers, his cock disappearing into her dripping passage over and over.
One of his hands slid over her hips, up her back, then back down, before curling around to manipulate her clit. She shrieked, and nearly came at the contact.
“Keep begging.” He grunted feeling his own end drawing near. He pushed deeper, barely slipping out an inch before thrusting in again. His pelvis pushed against the plug deeper.
Her pleading ran together, incoherent words left her mouth as she felt the swirling growing in her belly, her inevitable orgasm teasing her, tempting her to come without permission.
“Come.” He whispered in her ear and she cried loudly. Her body jerked and convulsed, her pussy clenched around his cock, squeezing and milking him as he came spurting inside of her body. Their orgasms seemed to last for hours, he kept his fingers on her clit, trying to keep her coming, to keep her on that edge, to keep her pussy clenching on his dick. The twitching of her inner muscles was intoxicating.
But in reality minutes passed, they collapsed onto th
e bed in a sweaty heap of tired limbs. “Fuck.” He grunted pulling out of her and falling onto his back. She curled her body towards his and sighed softly.
“Hmm wow.” She couldn’t help but smile a little. When she moved the plug shifted, causing her to wince, and whimper.
“You were a good girl, handled your punishment well.” He let a hand trail down her spine, tracing the curve of it. Then he cupped her ass, pulled her body on top of his before slowly pulling the thick plastic from her ass. It fell onto the bed, discarded, and then he reached up and unhooked the chains from her leather cuffs.
“So did I please you then?” She asked snuggling into his chest.
“You did.” He let his hands roam over her back before yanking a blanket over the top of them.
“Does this mean I get to be in charge tomorrow night?” Her voice was laced with sleep, exhaustion trying to take over her mind and body.
“We’ll see.” He told her, pressing a kiss to her forehead before letting his own eyes slip shut.