Society 1.3: Modernus Castigatio

"This will be your room. You will share it with Erik, and whomever I chose to offer you to. It is fully wired for video and sound, so feel free to open your holes to anyone or anything that is shoved inside. I expect you to be ready for double penetration within six months. That is a very very generous timetable, so of course I would be pleased if you were to stretch out your anal cavity before then.

"However, this training will take time. Take Erik's sweet hole, for example. Erik, come, Position One on your bed."

Erik crawled onto the bed on his hands and knees, then proudly displayed his ass, legs spread wide.

"Look. His ass cheeks are nice and firm, and a little bulbous. They almost hide his hole in this Position. But you can see it, can't you? Get close."

Jason knelt behind Erik at Mistress Elena's urging. She pushed his head close to Erik's ass. He smelled his own come and the heady scent of sex.

"Can you see that tiny flap of skin? That's a well-fucked, stretched out hole. Hidden behind those cheeks. What should you do?"

"Spread his cheeks, Mistress?"

"You could. I can certainly see the temptation. But then your hands would be busy holding them apart, and you can probably think of better things to do with your hands, right?"

"Yes, Mistress. Order him into Position Four, Mistress?"

"Perfect, little one. Do so."

Erik performed his role perfectly. When Jason ordered him into Position, he laid his cheek on the soft comforter and spread his ass cheeks wide.

Jason desperately wanted to shove his face into that ass again. To drive his tongue up that clutching hole. Siena had been amazing. But burying his face in this bear of a man's ass was heady beyond belief. Especially knowing it was his own cock that had fucked Erik wide. His own leftover dribbles of come slicking his face.

Elena saw the desire in his eyes and smiled with delight. He truly was a toy after her own heart.

"See how beautifully that loose skin stretches? But Erik can still grip a greased dime with that tight little hole. He's not ready to take on Master John, at least not yet, but he is the perfect ass for you to emulate at your current level.

"So lick it. Love it. Worship it. Learn it. Find out how many fingers you can put inside. How tight it gets. Get the lube, and use lots."

Elena sat down next to the tray of drinks and pressed the button to turn up the fire. Leaning back, she watched the scene on the bed idly as she sipped her drink.

Jason appeared to be trying to corkscrew his entire face up into Erik's hole. Leading with his tongue. Erik pressed back hard, rotating his hips and trying to find a way to pull Jason's long tongue even deeper into his ass. Elena was impressed that he was taking her so literally. He buried his face between Erik's cheeks and bit them. Then spread them wide again and lapped hungrily at the hole squeezing his tongue.

He finally broke away long enough to lube up Erik's ass properly, shaking a little the entire time. He could feel Mistress Elena's eyes on him. But no instructions. So he listened to her voice in his head and calmed himself. He'd worshiped Erik's asshole, as instructed. Now he was going to test it. He was going to find out exactly what an asshole felt like. Jason slid two fingers into Erik's hole, and tickled the sphincter.

Erik bucked his hips infinitesimally. Jason read that as a subtle hint to get on with it. He knew Erik could take a lot more than two fingers. He began fucking him with those two fingers, adding another one on each inward stroke, until all four fingers were buried in his nicely stretched ass. Tickling Erik's tightening muscles, he felt around, and found his prostate. He tapped against it and watched Erik jerk under his hand on his back.

"Found something he liked?" Elena teased mildly. Her pussy was dripping slowly onto the robe underneath her ass, legs spread wide.

Jason ducked his head to hide his smile as he nodded meekly. "Yes, Mistress."

"Put your entire hand in, but do not tighten it into a fist. Aim it. Like an arrow. I'd like to see how far up his ass you can get your arm."

Jason groaned at the thought and nodded. "Yes, Mistress."

Erik knew what would be needed, and quickly assumed Position One again. He shoved his ass higher in the air and arched his back. No matter what he did, this was going to hurt like hell. But it was a hell he desperately wanted, and so rarely got.

Elena watched Jason spread more lube on his wrist, and going up his forearm. He squirted more on Erik's ass as well, lubing from the stretched hole around his fingers up to the mounds of his cheeks.

Jason felt Erik's excited trembling. Even his ass muscles were twitching hard around his fingers. Erik wanted this. He wanted Jason's arm in his asshole. Jason wondered if he would be this man some day, trembling with want as another toy kneeled behind him, preparing him to be impaled.

Of course he would be. His ass would be shoved high in the air, and he'd be biting his tongue to keep from begging for it. Jason slid his thumb into the cradle of his fingers, and pushed his hand the rest of the way into Erik's cavern. He didn't quite bypass his prostate, stopping for a quick fondle, but moved on fast.

He stopped at the inner sphincter, and the curve. He knew from anatomy class what was there, but he didn't really know how to get past it. But he knew what helped him when he was fucked by their huge cocks, so he'd just have to emulate it.

Wiggling his fingers, Jason found the tight hole and tickled against it, easing more lube in and against the muscle. He moved in and out slowly, but kept up the pressure so that his in was always further in than his out. His fingers gently dug their way deeper into Erik's tightened passage until they found their way into the maze.

Elena smiled at Erik's roar of pain and pleasure. Jason's forearm was stretching Erik's channel beautifully. Jason was fucking him slowly, and still going deeper. Nodding in approval, she slipped the clit massager deep into her pussy and found her g-spot with it.

Erik shuddered and pushed back against Jason's arm. More, more, God, he wanted more. Please, now, deeper, harder. Not a word escaped his lips except for screaming thanks. When Jason balled his fingers into a fist, and used it to rub his way another inch deeper, Erik bucked on his arm before settling back into Position with panting gasps and moans.

Jason watched his arm disappear into Erik's ass with awe. About half of his forearm was in that dark tunnel, and he was still boring. He could feel his ribs. Jesus. Erik arched his back, screaming, and Jason adjusted his angle before stopping. But not for long. Only long enough for more lube to be applied, and for Erik to catch his breath.

Elena was surprised by Jason's instinctive understanding. She saw his muscles in his shoulders flex, and knew that he was twisting his wrist deep in Erik's hole. He was allowing the tunnel to slide over him, rather than forcing the folds. When he had reached the absolute limit, she stood and clapped. Pulling the massager off her finger, she slipped it into her robe pocket absently as she approached.

"Very impressive. Just beautiful. Perhaps you would be ready for Master John's cock, after all, dear Erik. I am very pleased. But, of course, this is not truly your training time, is it?"

Erik was sweating and shaking. He was a quarter of an inch away from begging Jason to stop when Mistress Elena had interrupted. "No, Mistress," he gasped. It sure as hell felt like training, though. He'd never taken that much in his ass before. Erik couldn't wait to see the videos. He wasn't even sure how much of Jason's arm was in his tunnel, but he definitely couldn't take any more.

"How does that hole feel around your arm, little one?"

"It feels incredible, Mistress. Alive, pulsing, twitching. I can feel his heartbeat in his ass." Jason was in awe, and barely resisted the urge to stroke Erik's back lovingly.

"I would be very pleased to experience the same sensation with your ass around my arm, little one."

Jason's eyes whipped up to hers in distress, then immediately fell back down to his work in Erik's hole. He gulped hard. "Yes, Mistress," he whispered, both terrified and excited.

Elena laughed. "Not tonight, little one. But some day, I will have you spread out like this for me. Speared on my arm. Your heartbeat pulsing around me. I would enjoy that. Would you?"

Jason worked his suddenly dry mouth and nodded again. "Yes, Mistress."

"Mm... you look a little worried, pet. I can't have that. Here. Look how far in you are. Measure your arm against his back."

He did as she told him, and was amazed again at how deep he'd sunk his arm into Erik's ass. Where his fingers measured, he stroked Erik's shaking back. It was obvious he was in barely-tolerable pain, but he was holding Position perfectly. His ass was even starting to relax a bit more, now that the invasion had halted.

"It's remarkable how much the ass can take. It's a much more flexible toy than a pussy. It's very tempting to stretch your ass all out of shape with every toy, fist, foot, and arm I can find. And I will. Please believe that your ass will take more than you can even conceive of right now. Every one of your fantasies will come true, Jason. And more. Now it's my turn for a fantasy. Pull out of Erik's ass. Slowly. As slowly as you pushed your way in."

Elena abandoned the toys and returned to her comfortable pose on the chair, legs spread wide. She sipped from her drink and languidly played with the hood of her clit while Jason untangled his fist from Erik's hole.

"Very pretty. Just beautiful. Erik's cock is nice and hard. Up, little ones. Position Two, Jason. Position Seven, Erik. Let me see that gape. Right here."

Elena motioned to the floor in front of her. The men woke from their sensual daze and rushed to do her bidding. While Jason knelt at her feet, Erik turned and showed her his gaping hole. Elena wanted to run her tongue around that huge circumference, but satisfied herself with a quick fist. Luckily there was still plenty of lube in his ass. Jason had been very thorough.

"Beautiful. Master John could fit in there. Tight squeeze, though, and he prefers a comfortable ride. You'll have to start taking two cocks more regularly when you are with Mistress Ray. Only so much can be done with dildos." Elena slapped Erik on the ass and leaned back.

"Now, Position Twenty, Erik. Face one another, my pretty pets."

Jason turned to face Erik, and was fairly sure what was coming next. He resisted the temptation to open his mouth, and waited for instructions.

Mistress Elena pulled the clit massager out of her robe pocket again and slipped it on as she leaned further back in her seat.

"I do enjoy watching you suck cock. I believe that you enjoy it. Do you, little one?"

"Yes, Mistress. I love hard cock sliding down my throat."

"Erik has been very sweet to you so far. Do you think that you can take a rougher ride? Different guests will have different needs, and I would be pleased if you could assist in assuaging the vast majority of them."

"Yes, Mistress." Jason's throat felt raw from the thorough pounding of both Erik and Master Jacob. But he opened his mouth obediently and tilted his head at an angle, trying to make a straight line with his throat. He heard the buzz of the massager get louder then muffled, and knew that she was rubbing it somewhere on her flesh.

"Very nice Position. Hold it. Erik's going to use that hole hard until he's ready to come."

Erik took Mistress Elena's instructions to heart. He pounded his cock into Jason's newly trained throat. Jason gagged and choked at the rough invasion, but Erik didn't let up this time. Taking a better grip on Jason's hair with one hand, he used the other to cup his jaw and widen his mouth even further with his thumb.

Jason groaned at the addition of Erik's thumb in the corner of his mouth. He slid the tip of his tongue against it. At the same time, he continued to rub the base of his tongue against the rest of the massive cock shoved into his mouth and down his throat. Gripping his hands behind his back tightly, Jason allowed his head to be angled and turned, then invaded again.

Although he appeared to be passive, Elena could see the muscles moving in his throat, and his fingers turning white where they gripped together. Once Erik got the angle just right, he began seriously pounding away at Jason's face.

Elena hummed in approval. She loved a good face fuck almost as much as an anal cocking. And her new pet was taking to both like a pro. Tossing one leg over the arm of the comfortable chair, she leaned back and began rubbing her clit harder with the massager.

Jason worked his throat against Erik's slamming cock. When choking bubbles of spit and precome threatened to overwhelm him, he allowed them to dribble past Erik's stretching thumb and down his chin onto his chest.

Erik knew that she wanted a long show. She wanted Jason's chest glazed with spit and juices. Then she'd probably want him to come on Jason's face and chest. Then she'd have Jason rub it all in.

He was right on at least two counts. Elena wanted a long show. She watched Erik fucking Jason's mouth avidly. Each drop of froth from his mouth was testimony to the pistoning action down his throat. The toy held Position perfectly, taking the oral abuse with admirable strength. She knew his jaw had to be hurting, and his throat raw. But he took the massive cock over and over, until his chest was finally glazed.

"Perfect," she murmured under her breath. Her clit was twitching, and Erik was shaking with the need to come. She realized that he hadn't had all that many opportunities yet. Besides, that fit in with her plans just perfectly.

"Erik, are you ready to come?"

"Yes, Mistress," he panted through clenched teeth.

"Come on my pussy. Not too close. Let's see how good you are at shooting. Aim from my knees," Elena directed, an amused smile on her face.

Erik's cock slid out one last time, and he let go of Jason abruptly. Turning, he took one step toward his Mistress before grabbing his cock, aiming, and firing. He shot off globs of come that clung to her thigh, her lower belly, and finally her pussy. Two fat globs landed on that tender flesh that she'd spread open in invitation.

"Impressive. Jason, clean up Erik's mess."

Jason's heart leaped into his throat, and he could barely get out the required response. Nodding frantically, he stopped himself from diving onto her come-laced pussy. He started instead with the come spot on her thigh. Scooping it up with his tongue, he showed it to her before dropping it onto her pussy. He figured that was where she'd wanted it. That was where it should go. He lapped up the remnants on her thigh, then moved on to her lower belly. He scooped up that gift, and offered her proof of his devotion before dripping it onto her clit.

Then he settled down between her thighs, and buried his face in the slippery heaven. He knew better than to try to tilt her hips up, or to dive his way into her sweet hole. He behaved as if this was the sweetest, most amazing treat of his life. Because it was.

While Jason slowly painted his face with Erik's come, using Mistress Elena's pussy lips as brushes, she melted back into the armchair and spread her legs further. Maybe she should allow herself to come this way.

Yes, that would be an excellent way around her little self-imposed moratorium. She'd been planning on just using dildos to come during Jason's training, at least if Master Jacob wasn't around. But that seemed like a very long time to wait for a lovely orgasm. Besides, every one else in The Society would be using him during his training. They would all come on him and in him.

Grabbing Jason's hair, she pulled his head back until his glazed face was raised to hers.

"Look at me, little one."

He raised his eyes to hers, trembling with desire and exhaustion.

"Everyone starts out as the House punch. Some toys love that. That's where they want to stay. They want their ass fucked day and night and back into day again. Some toys hate it, and work their asses off, so to speak, to get out of that position. Some toys love it, but want more from their time in the Society. I think you fall into that last category. Is that correct?"

Jason nodded, speechless. Mistress Elena was incredibly insightful.

"One must work one's way up the ladder. Next up from House punch is come sucker. Do keep in mind that just because one's title and primary duties may have changed, that does not mean that one should forget one's roots. Take, for example, Siena. She is acts as punch three days per month. They are on a rotation. I will be expecting all of my boys to be able to do the same."

"Yes, Mistress," Jason nodded again. Where was this going?

"So you will now be the House punch, and come sucker. To perform your duties, you must know how to lick a pussy properly. You were doing well, glazing your face. Do not look so hurt, little one. I did not give you permission to lick me yet. I am pleased at your restraint. But now you will show me any skills you may have acquired in this field, as well."

Adjusting herself once more, Elena spread her legs and let go of Jason's hair. He immediately got to work.

Suckling her labia, he thoroughly cleaned them with the flat of his tongue. He twirled along her smooth skin and sucked the opposite lip deep into his mouth. All of the fantasies that had been so cruelly shot down by semi-frigid females were coming to life under his teasing lips.

Mistress Elena allowed him to do anything he wanted. He dug his tongue into her steaming pussy and pulled out streams of slippery, clean juices. Swirling those juices around her folds, he worked his way back up to her clit and slid his tongue under the hood.

Elena jumped and smacked him on the head lightly. "Never under, for me. Some love it, but use it judiciously. You can suck on the hood like it's a cock, though. I like that." She offered him the hint to make up for the sharp cuff and relaxed back again.

"Yes, Mistress. Thank you for your loving guidance." There wasn't even a hint of sarcasm in his tone as he lowered his mouth to her clit hood and began suckling it carefully. His tongue naturally wanted to slide into that loose fold, and find her hidden secret. But he flattened his tongue instead, and lapped at the flesh as though it was a come-flavored lollipop.

Jason found out that his Mistress more than liked it. She went over the moon for his nuzzling, sucking, and lapping. Lifting her hips over and over, she shoved her tiny little cock against his mouth and rubbed, mashing his lips against his teeth. He continued to suck and lick at the flap while she ground on him.

Her thighs wrapped around his head and her hands pulled him even closer. He doubled his efforts, opening his mouth wide to suck more of her sensitive flesh. His tongue slipped under the hood and brushed her clit again.

Mistress Elena exploded under his mouth. Her back arched, and her hips lifted high off of the chair. Grinding her clit against his teeth, she gasped and screamed louder when he bit her clit hard. She bucked against his face, deep in the grip of the most mind-blowing orgasm she'd experienced in years.

It both infuriated and thrilled her. She went with the fury first. Kicking Jason away from her, she stood and shook the folds of her robe into place. She grabbed the end of his leash and walked out of the room. Jason scrambled to keep up, terrified.

He knew that he'd pushed it too far. He knew it even as his teeth had clamped over her clit. But he'd also known that it would give her incredible pleasure. At the time, it had seemed like a good trade off. A nebulous punishment for her pleasure. Easy decision, in the split second timing, with his nostrils full of sex.