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Caned For Lunch

  • Posted on May 17, 2009 at 9:28 pm

Caned For Lunch
by Mistress Twilight

Jack was alone in his office for lunch. He had locked the door, closed the blinds and told his secretary to hold his all his calls. He was not to be disturbed.

He leaned back in his chair while he downloaded some of his favorite porn pics. His favorite picture was of a red haired woman getting a hard over the knee spanking from her boyfriend.

Watching that chick’s tight ass getting redder and redder was getting Jack extremely hot. Within minutes, he had whipped out his cock and was stroking it rhythmically. He stretched back in his chair and was pumping his hand furiously when his door unexpectedly opened.

His girlfriend Daria walked in and locked the door behind him. He tried to hide what he was doing but her smirk told him she knew exactly what was going on.

She quickly walked around his desk and grabbed his hand off the mouse before he could close out the window. “You were supposed to call me you know.” She looked at his screen and her eyes grew wide.

“We were supposed to go out to lunch together today. But instead you’re sitting her looking at very naughty photos.”

Jack tried to stuff his cock back in his trousers but it was no use. It was too hard to get back into his pants. He was caught and was at her mercy.

Daria looked back at the photo on his monitor. “Hey! That woman getting spanked looks like me!”

Jack gulped. There was no denying it. This was exactly the reason the photos got him so hot. He tried to laugh. “Well, now we know what it would look like if the tables were turned.”

She arched an eyebrow and stared him down. “Funny. But don’t think I’m going to let this slide.”

“What do you mean? Let’s just forget about this and go out to lunch.” He knew it was hopeless to try to get out of being punished. But he had to try.

Daria got up and walked around his office. “There must be something around here that I can punish you with.” Her eyes lingered over one of the blinds.

“And I know just the thing.” She climbed onto the chair and grabbed at the stick that opened the shades. Taking the stick off the hook she stepped back to the floor.

As Daria started walking back to his desk she started smacking it into her hand. This made Jack extremely nervous because it sounded just like a cane. He licked his lips and tried another tactic with her.

“Honey, I’m sorry. You know I feel bad for not calling. We’ll go out anywhere. I’ll take you too your favorite restaurant downtown.”

She smiled. “I think that sounds like a great idea. And we’ll do that as soon as I’m finishing caning you.”

He stood up suddenly. “What?!”

“You heard me. Now take off your pants or I’ll double your punishment.”

Jack knew it was better not to argue when she used that tone. As he was taking off his trousers, she walked over to his computer and clicked on another picture from the porn site.

“You’re going to look at this picture while you take your punishment. I want to make sure you don’t stand me up again.”

She bent him over then and he was looking right at a picture of a red haired woman giving a harsh spanking to a man. Daria chuckled then. She was thoroughly enjoying herself. She leaned down and whispered in his ear.

“Now your secretary is just outside. This cane is pretty quiet so she won’t hear me punishing you. But you better be careful not to yelp. We wouldn’t want her to think I was in here punishing my naughty boyfriend now would we?”

A rush of excitement made Jack shiver. He groaned softly.

“Now Jack, you were supposed to call me at noon. So to punish you, I’m going to give you twelve cane strokes.” He nodded and braced himself for the first stroke.

Daria whipped her arm back and brought the cane down hard across his ass. Jack started to yelp and then clamped his mouth shut. The last thing he wanted was for his secretary to hear him getting punished.

Again and again the cane came down. Lines a delicious pain streaked across his bottom. After every couple of strikes Daria scratched her fingernails over his sensitive skin. Jack bit his lip to keep from moaning. The stinging pain mingled with pleasure every time she brought down her cane. The twelfth stroke was the hardest and Jack couldn’t stop a quick yelp from escaping his lips.

After rubbing his reddened bottom, Daria stepped back to admire her work. Jack sucked in his breath as she raked her fingernails over his now tender ass. He could hear the pleasure in her voice as she told him to get dressed.

Daria smirked while he pulled on his pants. Then she turned unexpectedly and walked away from him. He hurriedly buttoned his shirt as she opened his office door. She told his secretary they were going to lunch. The two women exchanged suspicious smiles and Jack hoped she hadn’t heard him getting disciplined.

They went out to Daria’s favorite restaurant. All through the meal he squirmed in his chair. He could feel each stroke throbbing. Daria looked very pleased with herself. She smiled and told him that she was confident he wouldn’t stand her up again. Jack couldn’t agree more.

Shoe Store Submission

  • Posted on April 25, 2009 at 3:02 pm

Shoe Store Submission
by Mistress Twilight

Carol was by her very nature a dominant woman. She knew what she wanted from men and she always knew how to get it.

Thursday evening she went shopping at her favorite shoe store downtown. A sale was going on and the store was crowded with shoppers.

Carol soon spotted a pair of high heels that interested her. All the clerks were busy so she found an empty seat to try them on herself. Sitting down she noticed a man walking towards her down a nearby aisle.

As she tried on the heels she could sense this man’s eyes upon her. Instinctively she pointed her toes while glancing up to meet his eyes. As suspected he was staring at her feet and licking his lips.

He must have felt her looking at him because he quickly looked away. His cheeks flushed deeply and he started to turn away.

Carol coughed softly and he turned back around. With a crook of her finger, she motioned for him to come over. Like a puppy he came and sat down besides her, looking at her for another command.

She took his chin in her hand and directed his gaze towards her feet. Purring into his ear she whispered, “These heels don’t suit me.” She held out her right foot expectedly.

He looked back at her, a hopeful gleam in his eyes. Carol told him what he longed to hear, “Take these heels off and bring me back a pair that are higher and that have ankle straps.”

The man’s voice was barely a whisper. “Yes ma’am.” He delicately took one foot in his hands and removed the shoe. For a moment he held her stocking coated foot lovingly. He licked his lips and looked up at her, begging permission with his eyes.

Carol knew he would suck her stockinged toes right in the store, in front of all the customers and employees if she commanded. While she would enjoy making him perform in public, she wanted to toy with him first.

She removed her toes from his hand and replaced it with the other heel covered foot. “Tell me your name.”

“Richard.” He dutifully took the other shoe off, placing it in the box next to its mate while simultaneously holding her foot with his other hand.

“I prefer to call you slave.” She slid her foot out of his hand and brushed her stockinged toes across his mouth. His lips parted and he closed his eyes.

Carol sat up and sat her feet on the floor next to his knees. “The ankle straps-” she reminded him.

Richard bit his lips in an attempt to stifle his moan. He obediently nodded his head. “Yes ma’am, right away.” He stood up and walked down the aisle he had come, taking the unwanted heels with him.

Carol smiled as she watched him shopping. He was carefully studying all the heels in her size, trying to find the perfect pair, the ones that would please her most.

Selecting a box he returned to his spot in front of her, sinking down on his knees again. She held out her foot and he lovingly held it in his hands, sighing with pleasure.

Carol placed her other foot between his legs and was pleased to feel the hardness of his cock. He closed his eyes and moaned again, louder this time.

“Put them on me.” Carol snapped out her order and Richard’s eyes snapped opened. He picked up the right heel and carefully slid it on. He tenderly buckled the ankle strap and set her foot down. She could see his hands trembling as he removed her foot from his crotch. He put the second heel on, again treating her as tenderly as possible.

Carol removed this heeled foot from his hands and stood up slowly. Richard was transfixed on the floor, whimpering softly.

She looked down at her new toy. “I think I’ll just try these out. You can stay right where you are.” She turned and walked away from him, deliberating walking slowly, knowing very well Richard would be watching her every move.

When she returned to her chair he was in the same spot. He hadn’t moved from the floor.

Wordlessly she slid back into her chair. She held out one foot. This time she didn’t need to command him. He obediently took off these shoes and put her original heels back on.

She stood up as if to go. Again she cupped his chin in her hand. She smiled at him and whispered, “You’ve pleased me tonight.”

Then she reached into her purse and handed him her card. “If you would like to please me again, you will bring those heels (her eyes drifted to the pair she had just tried on, now sitting in their box besides Richard’s leg) to the address on the card next Thursday evening. I will toy with you at 7. Leaning down she whispered in his ear once more. “You’d like to be my slave wouldn’t you?”

Richard moaned out a yes and Carol chuckled to herself. Leaving him like that, kneeling on the floor of the store, she turned and left. She knew he would be worshiping her in those heels the following week.

Virgin Slut Hole

  • Posted on February 27, 2009 at 2:25 pm

Virgin Slut Hole
by Mistress Twilight

Bill rode the subway home. It was a late night and a chill was in the air. He, however, felt very warm inside. Holding the hand bar as the subway rode along, he remembered the events that led him to tonight, returning home after a session with his Mistress.

He had always had submissive tendencies, but had never found a woman who desired that in a man. Finally, he worked up the courage to go to a support group. The people were friendly and supportive and while he remained hopeful, he had yet to find someone. There was a holiday play party at Christmas and he went, dressing up for the occasion. He wore black spandex and a leather harness he had bought himself as a present.

At the party he felt shy and couldn’t work up the courage to strike up a conversation. He kept to himself, quietly sipping his punch. He watched as a woman flogged a man across the room, wishing that it were he.

Then a sultry voice whispered into his ear, “I can see you’re looking for something. Guidance perhaps? Instruction?”

He turned and saw a beautiful woman, the sight taking his breath away. She was tall and voluptuous, wearing a black leather corset and short leather skirt. Her long black hair framed an enchanting face. Her lips moved sensuously as she spoke with intense eyes focused upon his.

He stayed by her side the rest of the night. He confessed his submissiveness to her and his newness to the lifestyle, but he could tell she had already guessed these things. After that night she began to train him as her slave. Over the winter he went to her condo across town at the end of every week.

He was to wear a leather cock ring during these visits. He put it on before work and wore it all day. After work he rode the subway to his Mistress. One Friday he woke up late and forgot the cock ring. The day was hectic and he didn’t remember until he was walking to the subway station. He didn’t have time to run home and get it; that would make him late for her and she did not tolerate lateness.

He arrived and duly apologized. She punished him anyway. She placed him over her knee and gave him a thorough hairbrush spanking. After she had finished she began stroking his ass cheeks.

“And what do we have here slave?”

“Nothing Mistress,” Bill replied nervously.

“Nothing? Why it looks like a slut hole to me.” Mistress ran her finger over his opening, causing him to shiver.

“Mistress, I’ve never been touched there before.”

“A virgin slut. Mmmm, I like that.”

And that was all she said. She rubbed his tender ass and soon dismissed him. He wondered about her actions. She had been pleased to learn of his innocence but had done nothing beyond questioning him. All week anxiety and expectation plagued him.

Another Friday came and he went to his Mistress as usual. She opened the door with a devilish gleam in her eye. As was expected he began to undress and knelt on the floor when fully disrobed.

Mistress began to pace back and forth in front of him.

“Now you promised to do anything for me. Is that true?”

“Yes, Mistress.”

“You promised to give anything to me. Is that true?”

“Yes, Mistress.”

“You swore to hide nothing from me. Every part of your essence belongs to me. Is that true?”

“Yes, Mistress.”

Her heels made clicking noises as she walked slowly in front of him.

“Today I will test these promises. I want you to prove your obedience to me. Do you understand”?

“Yes, Mistress.” Bill was shivering now. Not knowing what to expect but eager to prove himself, he waited patiently.

She sat upon the sofa and beckoned him silently with one finger. Bill crawled across the floor and kneeled before her.

She pulled him over her knees and began to spank him with a studded leather paddle that lie beside her. The spanking was long and sensual. The intensity slowly built until his ass was stinging and he writhed against her thighs.

Mistress set aside the paddle and began to fondle his behind, scratching her fingers against the skin and squeezing his asscheeks.

“You will deny me no part of yourself will you slave?”

“No Mistress.” Bill felt her part his asscheeks and run a finger over his asshole.

“Even this little slut hole, this most private part of yourself is mine isn’t it?”

“Yes Mistress.”

Her finger withdrew for an instant and then returned to rubbing the rim of his asshole. It was now wet and cool and slid into his tightness easily.

“Yes this is embarrassing,” Bill thought. It even hurt a bit. But the pleasure of being entered was intoxicating.

Mistress stroked him with her finger. This made him lift up to met her and moan, with each curve of the finger.

“You will take whatever I give won’ t you?”

Bill could barely utter the words “Yes Mistress” between moans of pleasure.

“Good. Relax slave and you will take more.”

He relaxed his muscles and waited. Her finger withdrew halfway and stopped. Another cool, wet finger slid inside and he shuddered in ecstasy. All embarrassment had melted away and he gave himself to the intoxicating sensations. He was hard and rubbed against Mistress’s lap.

“You are such a slut. This little hole is sucking up my fingers.” She plunged deeper inside of him. “You want more don’t you?”

“Yes Mistress, please.”

“Beg for it. Tell me what you crave.”

With this prompt, Bill began to beg in earnest. “Please Mistress. Please fuck my slut hole. I long to be filled. Please fuck me like the slut I am.”

She withdrew her fingers as he pleaded. At once he stifled a cry, the empty feeling surprising him.

“Go to my dresser and bring me back the cock that’s in the top drawer.”

Bill crawled to her dresser and stood before it. His hands were shaking so badly with anticipation he could barely open the drawer. Inside nestled among her lacy panties sat a dildo and leather harness.

Instinctively he knew he was to crawl back to her. The humiliation of what would follow was overwhelming. He couldn’t relax while she put it in his…

But it wasn’t his anymore. It was her slut hole now, hers to do with as she pleased. With this in mind he placed the dildo in the harness and the head in his mouth. He crawled back and waited for her to begin.

“Very good. But you took too long. You were wavering weren’t you?”

Bill nodded a yes.

“You will take twenty for doubting. Present.”

He instantly laid the dildo on the coffee table and bent over, spreading himself for her. Clicking heels told him she had left the room. She had returned with her slapper. It was made of thick leather and wielded a nasty sting. As promised, she delivered twenty strokes, each one giving him a sharp sting and rocking him on his feet. Bill thankfully kissed the slapper and apologized earnestly for his doubting.

“Lean over the back of the sofa.” Nervousness returned as he followed her instructions. She came up behind him and firmly grabbed his rear. It was sensitive from the beating, causing him to wince slightly.

The coolness of her finger slid inside him again. Anxiety melted and he arched his ass into the air.

“You want this don’t you?”

“Yes Mistress, please. I’m such a slut. Please fuck me like a cheap whore.”

During his pleadings she had slipped another finger inside his tight hole causing him to moan these words. Fingers withdrew and the cold wet head of Mistress’s cock pressed against his puckered slut hole.

“I want you to relax your entire body. Open yourself up completely. Breath slowly now…”

“Yes, Mistress.”

The head slid inside of him and his body stretched to receive it.

“Take a deep breath.” As he inhaled she slipped the cock deeper within and his well-lubricated hole widened, sucking her in eagerly. She worked the cock in and out until she could easily slide all of it inside.

Mistress pulled almost out of him then and shoved back in, filling him completely. Bill whimpered from the pleasure and the pain. Ecstasy rippled through his body.

“You like this don’t you slut?”

“Yes, Mistress. Thank you… Thank you.”

She fucked him long and hard. Sensations began to build and his cock strained for release. Unable to stroke himself because his hands were pinned behind his back, Bill softly moaned into the upholstery.

Her thrusts intensified and he groaned loudly in response.

“You can come from me fucking you, can’t you little slut.”

“Yes, Mistress. Please may I cum while you’re inside me?”

“Let me hear how much you want it.”

Bill begged and his cock began to throb. Pleading always brought him to the brink of orgasm.

Reaching around his thigh, she grabbed his balls and squeezed them hard, digging in her nails.

“Cum now slave.”

The orgasm overtook him and he spurted in rhythm as she thrust into him, pounding him against the upholstery. The only sound to be heard was his exhausted panting as she slowly pulled out of him.

“Thank you, oh thank you Mistress.” Bill’s voice was just a whisper now.

“You made a mess all over my sofa. Clean it up.” Her nails scraped his scalp as she grabbed a fistful of hair and pushed his face into the cum soaked spot. He licked up his cum gratefully, so eager to please her.

She excused him shortly afterwards. Bill went to his pile of clothes, dressed and thanked her once more. Then he caught the subway and rode it across town.

Riding home, swaying slightly as the subway rumbled along, he smiled at these memories. His ass tingled, his hole still throbbing from her cock. He cherished these sensations and knew he’d never be the same again.