Punishment and Submissive Pleasure with a Mistress

It was Conrad’s overwhelming lust to submit that brought him to a stranger’s doorstep. For years he’d constrained himself to masturbating to pornographic fantasies, erotic stories, and personal ads from dommes seeking submissive men. Finally, he’d gathered the courage to throw caution to the wind and respond to one of those personal ads.

It was the straightforward nature of the ad that had drawn Conrad to it:

Lifestyle Domme Seeks Submissive Male – I find satisfaction in showing submissive men what it really means to offer themselves to a woman. I will push your limits and show you exactly how deep your submission goes.

I don’t want your money. I don’t want you to grovel. I simply want you to submit. Bonus points if you’re willing to surrender and push past what you thought your limits were.

Mistress Skye

Conrad messaged Mistress Skye over a period of a few weeks, and when she invited him to come to her place for an in-person session, he eagerly accepted. He felt as though he’d gotten to know this seductive domme and he couldn’t deny an ever-increasing need to meet her in person and submit to her desires, whatever they might be.

The woman Conrad knew as Mistress Skye answered her door and stepped back to welcome him to her home. She looked rather conservative in a knee length skirt and a cardigan sweater, though the sweater was buttoned up and tight enough across her breasts that Conrad found them rather fetching. Her hair was pulled back into a ponytail and she wore a pair of black-rimmed glasses. Conrad couldn’t help but conjure a naughty librarian fantasy.

“Welcome, Conrad,” she said as he stepped into her home.

“Thank you for inviting me,” he said.

“I’d like you to refer to me as Mistress Skye while we’re in my home, Conrad,” the elegant beauty said in a firm voice.

“Yes, Mistress Skye. I apologize,” Conrad replied as his gaze turned downward. He slipped into an easy, deeply satisfying sense of submission with ease.

Mistress Skye led him to her living room and directed Conrad to sit on one of the two soft-looking couches. She sat across from him.

“So, Conrad, are you nervous?” Mistress Skye asked as she crossed her legs and subtly leaned forward.

“A little,” he admitted. “As I said, I’ve never done this kind of thing before. I’ve only fantasized about it.”

“And have you fantasized about what today might entail?”

Conrad blushed a little. His first instinct was to lie, but he knew that was unwise. He had fantasized about it.

“Yes, Mistress Skye, I have,” he admitted.

“And what happens in those fantasies, Conrad?” Mistress Skye asked as she uncrossed and crossed her legs once more.

Conrad couldn’t help but glance between her legs. Instinct lured his eyes between them. He was hoping to catch a glimpse of her panties. He looked away as quickly as he’d tried to stare.

“I pleasure you, Mistress Skye,” he answered.

“And how do you pleasure me, Conrad?”

Conrad felt a touch of lust in his loins. His cock stirred to life as he conjured an image of Mistress Skye’s pussy and his tongue licking it feverishly to make her cum. “By worshiping your body, Mistress Skye,” he answered.

“There are many ways for a man like you to pleasure a woman like me, Conrad. Do you understand that?” she asked.

Conrad wasn’t sure he did. “I don’t know if I do, Mistress Skye.”

A devilish smile crossed her face. “Then let me show you.”

Mistress Skye stood and gestured for Conrad to do the same. She led him down the stairs to her basement. He was expecting to find a fully kitted out dungeon. Instead, it was a fairly standard-looking space with a few couches, a plush carpet, a TV hanging on the wall, and a wet bar against one wall.

There were three wooden columns, equally spaced down the middle of the room. Conrad noticed scuff marks up and down the middle column.

“Please take your clothes off,” Mistress Skye demanded as she stood in front of the middle column.

Conrad had prepared for this. Mistress Skye had been very clear that he would need to be comfortable being naked in front of her and that he shouldn’t bother coming if he wasn’t. He was ready, and he stripped immediately.

“Stand here,” Mistress Skye said as she pointed to the ground in front of the column.

Conrad moved into place and watched as Mistress Skye opened the top drawer of a small dresser that sat against one of the walls. She pulled something shiny out, though he couldn’t see it.

“Put your arms around the column and clasp your hands,” she ordered.

Conrad hugged the column and was greeted by the feeling of cold steel against his wrists. Before he knew what was going on, he was handcuffed. He instinctively pulled against the cuffs. When it became clear he was now stuck in Mistress Skye’s basement until she released him, Conrad briefly panicked.

He thrashed against the handcuffs. He pulled hard, banging them into the wooden column over and over until his wrists hurt. When he took a moment to breathe, he understood why the column was scuffed. He wasn’t the first man to end up cuffed in Mistress Skye’s basement.

By the time he gathered his wits and looked around him, Conrad saw Mistress Skye holding a long black riding crop with a thick leather tip. His blood ran cold.

“What are going to do with that?” he asked.

“I’m going to show you one of the ways you can pleasure me,” she answered.

Mistress Skye stepped behind him and the whooshing sound of the riding crop moving through the air filled Conrad’s ears before he cried out in pain. The leather bit into his flesh and sent waves of agony up and down his body.

“Please, don’t,” Conrad begged. It was just one stroke but the pain was far too intense. He didn’t want more. He couldn’t take it.

Mistress Skye said nothing. Instead, she struck his ass once more with her riding crop. She hit a different spot on his sensitive ass. More pain rippled through his body.

“Do you understand, Conrad?” Mistress Skye asked.

“What? I don’t…what do you mean?” he said. His voice quivered as he spoke. His ass throbbed.

“Your pain, Conrad. It brings me pleasure. It turns me on to see you suffer. It turns me on to see the agony on your face as I beat you with my riding crop.”

As the pain receded, Conrad once more felt a sense of panic. What had he gotten himself into? He’d never met this woman, and yet he’d agreed to go to her place to submit. He’d agreed to get naked. He’d agreed to let her cuff him. Now he was stuck in her basement and unable to escape.

“Do you understand, Conrad?” Mistress Skye asked.

“Yes, Mistress Skye,” he answered.

He did understand. Conrad’s explorations of domination and submission had educated him to the notion that there were women and men that found pleasure in inflicting pain and suffering on a submissive. He didn’t think of himself as the kind of guy that wanted to be on the receiving end of that, but now he didn’t have a choice.

The whoosh of the riding crop filled the air once more as Mistress Skye struck Conrad’s ass. He cried out and she beat him again, this time on the other ass cheek. He heard her moan. There was no question she was turned on.

Instead of delivering another blow, Mistress Skye stepped in front of Conrad and leaned the riding crop against the column. She unzipped her skirt and let it fall to the floor, revealing a pair of black lace boyshort panties he found irresistible sexy. She slowly unbuttoned the cardigan next, revealing a matching black lace bra.

“Do you like what you see, Conrad?” Mistress Skye asked.

“Yes, very much, Mistress Skye,” he answered.

“Would you like a chance to worship me, Conrad?” she asked.

He nodded vigorously. He would have done anything for that chance. “Yes, Mistress Skye.”

“There’s a price to pay for such a privilege, Conrad. Do you understand that?”

Conrad hoped he’d just paid the price, that suffering through the extreme pain of having his ass beaten with a riding crop was enough to earn him the chance to worship the woman standing in front of him.

“Yes, I understand.”

“Very good,” Mistress Skye said.

As she moved closer, Conrad was certain she was going to unlock his cuffs and push him to his knees. Instead, she stepped next to him, grasped his testicles in a painfully tight grip and said, “I’ll be back in a little bit, Conrad. You wait here.”

She squeezed his balls even tighter and he groaned in pain before she released them. Conrad listened to her walk up the stairs and shut the basement door behind her. Once more he felt a sense of panic. He had no idea when she would return. She said she’d be back, but there was no reason to believe it was going to happen anytime soon.

Without a clock in the room, Conrad was unable to measure the passage of time. When the doorbell rang, he had no sense of how long it had been. Thankfully, the basement door opened a few minutes later and Conrad heard two people walk down the stairs.

“Daniel, this is my toy for the day,” Mistress Skye said as she walked into the basement with a tall, well-built man.

Conrad felt small as Daniel stepped closer and began to strip. The man had exceptionally muscular arms, an impressive six pack, and big pecs.

“He’s beautiful, isn’t he?” Mistress Skye said as she ran her fingers over the now naked man’s chest.

“Yes, Mistress Skye,” Conrad agreed.

“Good. Then you won’t mind sucking his cock for me,” she said as her fingers encircled Daniel’s growing erection and stroked him.

“What? No. I can’t do that,” Conrad replied.

“Of course you can. You have a mouth, so you’re perfectly capable of being a cocksucker and fluffing Daniel for me.”

“But I don’t want to,” Conrad said.

“We haven’t known each other for long, Conrad, but you should know by now that I don’t care what you want. You’re going to suck Daniel’s cock because it’s what I want you to do. You’re going to stop complaining and do as you’re told.”

“Please, don’t make me do this,” he pleaded.

“Good behavior will be rewarded, Conrad, but you’ll have to suck Daniel’s cock to have any chance at claiming your reward.”

Conrad looked from Mistress Skye to the man standing next to her. His eyes traced down Daniel’s muscular body and between his legs. His cock was almost fully erect now and it was exceptionally large. Quite a bit larger than the erection Conrad was sporting between his legs.

A deep, surprisingly satisfying sense of submission came over Conrad as he sank to his knees and said, “Okay, Mistress Skye.”

“Does that seem like what I want to hear, Conrad, or should you rephrase that?” Mistress Skye said in a stern voice.

Conrad looked up at her. She was impossibly beautiful and from his angle on the ground she looked exceptionally dominant.

“May I suck his cock for you, Mistress Skye?” Conrad asked.

“Yes, you may,” she said.

Mistress Skye released Daniel’s erection and the muscular man stepped forward. He placed his cock in Conrad’s mouth and the submissive did his best to give his first blowjob.

To his surprise, the head of the cock felt soft against his tongue. The shaft was stiff and Conrad could even feel the veins as the dick moved deeper into his mouth.

It wasn’t long before he gagged, and when Daniel didn’t pull his cock out Conrad panicked. His hands were still cuffed and he could only move so much, meaning the muscular man in front of him could literally choke him with his dick.

Thankfully, after Conrad choked and spit up around the dick in his mouth Daniel pulled out. A few moments later his cock was against Conrad’s lips once more, eager to push into his mouth for more oral pleasure.

Mistress Skye picked up her riding crop and moved behind Conrad. She gently struck his ass, causing only small waves of pain as he sucked cock.

“Your service pleases me, Conrad. To see you submit to his superior cock thrills me. To see you embrace your natural place as a cocksucker for an alpha male makes me tingle with desire. You’re a very good boy,” she said in a sweet voice while peppering his bottom with the leather tip of the riding crop.

“Now you’re going to watch him fuck me,” she said.

Daniel pulled his cock from Conrad’s mouth and Mistress Skye pulled off her panties, leaving her wet pussy exposed.

She moved to the floor next to Conrad, giving him a remarkably good view of her pussy as Mistress Skye’s legs parted.

“Fuck me, Daniel,” she said.

The muscular alpha male moved between her legs, slipped his cock inside her, and quickly found a rhythm that made the beautiful dominant woman moan.

Conrad couldn’t keep his eyes off of the beautiful sex unfolding in front of him. His cock throbbed with desire and he periodically tried to pull against the cuffs. He badly wanted to masturbate.

“You want to play with your cock, don’t you Conrad? You want to pull on your dick while you watch a superior man fuck me, don’t you? You’re quite the little cuckold,” Mistress Skye said as she took the hard, fast pounding. “Don’t worry, you’ll get your reward soon enough.”

Conrad wondered what kind of reward she had planned for him. Would he get sloppy seconds? Would he be allowed to masturbate? Would she give him a handjob or perhaps even a blowjob? Some seemed more likely than others, though Conrad admitted that it was possible she had no intention of offering him pleasure.

Before long it seemed clear that Mistress Skye was going to cum. Her eyes were closed and she was moaning louder. Her legs wrapped around Daniel and he fucked her harder.

Just as she seemed to be approaching her orgasm, Mistress Skye reached out and grasped Conrad’s balls. She squeezed them tightly enough to make him cry out in pain. The closer she got to cumming, the harder she squeezed. Conrad experienced agony as she experienced the joyous bliss of orgasm.

Only when Mistress Skye finished climaxing did she release his testicles. They throbbed in pain as he closed his eyes and breathed deeply. His cock was still stiff, though. His arousal could not be denied.

When Conrad opened his eyes once more he saw Daniel pounding Mistress Skye. The beautiful domme had her eyes closed once more and she looked to be caught up in the pure bliss of having a big cock inside her.

Moments later, Daniel grunted and held his cock inside Mistress Skye. He was cumming. Conrad was sure of it. It struck him as exceptionally beautiful.

When Daniel pulled out, Mistress Skye turned and smiled at Conrad. “Are you ready for your reward?” she asked.

Conrad nodded and watched as Mistress Skye retrieved the key to his handcuffs and unlocked them. He felt a genuine sense of joy at once again having his freedom. He rubbed his wrists and looked at the beautiful naked woman in front of him.

“For a submissive cocksucking pain slut like you, it should be considered a great reward to be given permission to worship my cum-filled pussy. To clean the cum of a superior man from my cunt is exactly what you should crave right now,” Mistress Skye said as she turned to face Conrad and spread her legs.

He looked between them and saw the cum leaking out of her. Her words wormed their way into his brain and took hold. He felt an unexpected urge to do as he was told.

“Do you want your reward, Conrad? Do you want to be a good boy and clean Daniel’s superior cum from my cunt? Do you want to secure your place as my submissive?”

Conrad looked at her. Was she offering him a chance to come back and do this all over again? Was she going to take him on as a regular submissive?

“Yes, I want to clean Daniel’s superior cum from your cunt,” he answered.

“You may do so, though you will refrain from masturbating,” she said.

Conrad moved between her legs and licked the other man’s cum from her pussy. He devoured it. The taste was a little unpleasant, but he’d already sucked cock and didn’t feel any need to be shy about embracing the consumption of another man’s cum.

When Mistress Skye moaned with delight it filled Conrad with joy. It made him feel like he was doing a good job, like he was pleasing her in ways he hadn’t imagined possible. He was finally getting to worship her pussy, too. He was finally getting to taste her, even if she tasted like thick, salty cum.

“Eat it all, Conrad. Submit to my cunt. Submit to his cum. Submit to me,” she said.

Conrad did as he was told. His hard cock rubbed against the carpet. He no doubt stained it with his precum. He feverishly devoured the thick, rather large load of cum dripping out of her. He wanted to stay between her legs as long as possible.

“Very good,” Mistress Skye said when he was finished. She gently pushed Conrad away from her pussy, denying him further pleasure.

“You may get dressed and go home, Conrad. I’ll get in touch when I want you to serve me once more,” she informed him.

Conrad felt disappointed, but only because he wanted to stay in submission to Mistress Skye forever. A handful of hours didn’t feel like enough. He knew she would invite him back, though, and that pleased him.

“Yes, Mistress Skye. Thank you for letting me serve you,” he said.

“You’re welcome,” she said before caressing his face and giving him a soft kiss on the cheek. “I’ll see you soon.”

With that she took Daniel’s hand and led him upstairs. Conrad got dressed and when he ascended the stairs the two lovers were nowhere to be found on the main floor. Instead, he heard the sounds of sex coming from the second floor. Mistress Skye was getting fucked again.

Conrad let himself out and walked to his car with a smile on his face. It had been a truly spectacular day and he hoped to repeat it again as soon as possible.