The Harder They Cum Ep. 09

Dianna ran her hand across Conner's shoulders and down his back. She cupped his right cheek and tapped her fingers on his brand thoughtfully.

"How long?" She pulled the sub's ass apart with both hands.

"One week. I need some R and R, away from the unconscious influence my sub has on me when I'm trying to make important decisions."

Siobhan watched Dianna trap Conner's testicles in her hand and tug experimentally on the ball sack.

"Spread." Conner widened his stance to about three feet and arched his back. He had become familiar with the routine. Most women approved of a sub who knew how to act when he was being inspected.

"Anything I shouldn't do to him? Give me an idea of what his limits are." Dianna sucked on her forefinger before working it into the sub's lower dildo hole. Conner grunted but held his pose while Dianna searched for his prostate.

"Hands up sub," Siobhan ordered. The command triggered a conditioned response. Conner laced his fingers together on top of his head, straightened his back and accentuated his arch for Dianna's probing finger.

"Sure, I can look after him. It happens that I am between subs. My last boyfriend didn't work out so I had to let him go." Her finger moved easily in and out of the slut's hole.

Dianna looked curiously at Siobhan. "He's very easy to penetrate. Have you been pegging him a lot?"

"He's been practicing," Shiv replied cryptically. "Anna told me she trusts you to keep him active. I just need some reassurance that you won't damage him while I'm gone."

Dianna laughed. "You're worried I might leave a mark on your branded sub-slut? Relax Siobhan, take a break. You will get your man-whore back in good working condition." Dianna's finger vacated the sub's hole then traced the MW scar on his buttock.

"Stay!" Conner held the position: hands on his head, elbows at right angles to his body, back arched, ass hyperextended, legs spread, cock erect. Dianna ran her hand down Conner's back over his buttocks and between his legs. She weighed the sub's balls in her hand thoughtfully.

"Perhaps he might even come back to you a little more responsive," Dianna mused. "Sometimes they need to be disciplined to remind them how lucky they are to be owned by a caring mistress." Dianna slapped the sub on the ass and stepped back. She glanced at Siobhan. "Any special instructions?"

"I milk him at least once a day unless he's being punished. Keep him caged when you're not using him. If you plan on making him cum for an audience I would advise denying him for a couple of days before." Siobhan reached forward and stroked Conner's erect cock until he started grunting. "Good boy Conner. You're going to be staying with Dianna for a few days. Be obedient and remember, I love you and we'll be together again soon."

"Are you talking to your sub or his cock?" Dianna snickered. "I don't have a problem making that distinction. It's all about cock availability for me."

"All about sub humiliation, you mean. But that's ok with me. As you said, I should get a little more gratitude for how well he is used." Shiv grinned and slapped Conner's boner. It bounced from side to side. Shiv laughed to reassure Conner that she was not upset with him, and to show Dianna how unconcerned she was with sub disobedience. "Bad slut! Show some thanks for how well I have allowed you to become the pussy-licking, ass-fucked, submissive male whore that you clearly always were!"

"Anything Ma'am! Please tell me what I can do to please you Ma'am." The sub sounded so needy, like he couldn't wait to humiliate himself.

"Shut up slut. Is that pre-cum I see oozing out of my pet cock? What did I tell you about that, you depraved, over-sexed sub-bitch. We'll address your insatiable needs and inability to follow instructions when I get back. Meanwhile, you will go with Dianna and do whatever she says. Dianna will be in charge of your discipline while I am away. I expect you to be hard and ready to go when I get back in a week. Grunt if you agree."

Conner grunted as though he had a choice, then blushed. How was that even possible? How could he have any shame left? He was about to be kept as a whore by a woman who gave herself pleasure by humiliating him. Shiv had given him to this woman. The same slim white woman who wanted to dominate him before. But Anna had stopped her. Now she would do what she wanted with him. That probably involved pegging him and making him lick her little white cunt. She would likely spank him to show him his place.

Conner blushed, thinking about his fate, but his shame came from looking forward to it. Beyond even shame now, Conner felt his cock leaking pre-cum again.

"Anna assured me you are the best at creating appreciation for the training we do to our males." Siobhan smiled at Dianna. "See if you can get rid of his complacent attitude. I'm staring to prefer something more like Anna's subs. A sub that is more grateful to be used. Actually, more of a cum slut than a sub I guess."

Dianna attached a leash to Conner's collar. "Hands behind your back." The cuffs clicked shut and Dianna pulled on the leash. "Don't worry about a thing," she tossed over her shoulder to Siobhan. "Let's go man-whore."

"Be good Conner." Siobhan called after her sub. She wondered if she was doing the right thing by leaving Conner to the dubious mercy of Dianna, as she watched her naked whore stumble along after his new handler. Oh well, how fucked up could he get in a week? Shiv thought.

Dianna led her new man-whore down some stairs into the basement. After ushering him along a short corridor she opened a metal door and pulled the sub into a tiny room.

A mattress lay on the cement floor under a small barred window set high in the wall. There was a toilet in one corner. Dianna unlocked and removed the handcuffs. She unclipped Conner's lead and replaced it with a six foot chain, attached to a ring bolted into the wall over the mattress.

"You will live here. If I want to use you someone will fetch you. Disobedience will not be tolerated. Any hesitation or refusal to obey commands will result in a whipping. Bend over."

Conner bent forward from the waist and put his hands on the floor of the cell. Dianna kicked his feet impatiently and Conner spread his legs apart. She played with the ball sack briefly, just enough to begin stiffening the hanging cock. Dianna squatted in front of the sub and pulled his head up.

"Open." Conner opened his mouth obediently and Dianna filled it with a butt plug.

"Suck, bitch." Conner licked and sucked on the rubber plug. He knew where it was going and wanted it to be as lubricated as possible.

"Enough." She pulled the ass plug out of his mouth and stood up. Dianna walked casually to the back end of her bent-over bitch then separated his buttocks with her hands and inserted the wet plug into the sub's other whore-hole. Conner grunted as his tightly stretched asshole gradually accepted the over-sized plug.

"Make sure that ass plug stays in. Failure to do so will result in a whipping. There are closed circuit TV units in all four corners of the room so I can see what you are doing at all times. Get some sleep while you can bitch, you're performing for a few of my close associates this evening."

Dianna contemplated the nude, shackled sub-man. He was probably still too shocked about recent events to bother caging his control stick. Still, better safe than sorry.

"Stand," she directed.

Conner unbent until he was erect. He knew enough to keep his hands behind him, away from his cock. That belonged to her now. Dianna slapped him across the face, hard.

"I expect you to know enough by now to present your cock to me whenever the opportunity arises, she chastised him. "Failure to present the cock again will constitute an insult to your Domme and will be punished by a whipping!"

Abashed, Conner snapped his hips forward and thrust his stiffening cock into Dianna's waiting hands. She snapped a metal ring around his genitals, forced the semi-erect cock into it's cage and locked it in place. She wanted him extra needy tonight. Without another word Dianna slapped the sub's ass and shut off the light.

Conner knelt in the gloom then crawled onto the mattress. The plug jutted out and forced him to lay face down with his ass slightly extended, as though waiting be used.

Sleep? He was exhausted but sleep was the last thing on his mind. It didn't really concern Conner that he was being observed. What was there to see? He was caged, tethered and butt-plugged. Removing his plug meant being whipped, so he wasn't doing that. Although Conner was certain Dianna would come up with some excuse to whip him anyway.

No, the purpose of the cameras was primarily to keep Conner focused on knowing he was being watched. Besides satisfying her voyeuristic tendencies as a bonus, Dianna knew that over time, the sub would become accustomed to the scrutiny and

accept being observed by others.

That would render him highly susceptible to the suggestions of others. The ideal circumstances in which to maintain control of one's sub-slut.

He would need to be available anytime. He had to learn to be accessible at her whim. That meant he had to relinquish any sense of routine and learn to respond to her irrational impulses. Ultimately that meant stiff cock, penetrable ass and extended tongue whenever she wanted.

She would vary his milking times so he would not be able to predict rest periods. Very soon she would train his cock to get hard whenever she touched it, regardless of how often she made him erect, or how long he was forced to endure the celibacy she imposed. He would learn how to cum three or four times in a row for her. He would learn to beg for it. She would make his cock belong to her.

One week. Seven days to train Conner to respond to her hand. Challenging, but she was sure she could use that time to teach Shiv's pet cock a few new tricks. Shiv would appreciate her handiwork and recommend her services to Anna.

Anna was where the real action was. She had her fingers in dozens of decadent situations around the city. Anna could hook her up with wealthy women like herself; women who would pay to have their men's attitudes adjusted. Giving males an attitude adjustment was what Dianna excelled at most.

Watching the CCTV from her study upstairs, Dianna noticed that the sub was still awake. She considered injecting him with a sedative, but that might dull his senses too much. She wanted him sharp for the others.

If she milked him now, would he still be able to cum later for her friends? Silly thought, of course he would, assuming she allowed him that privilege.

Dianna started toward the basement. The milking would make him drowsy afterward. Post-coital tranquility was more energizing than sleep anyway. At least that's what she told her subs.

The metal door creaked open and Dianna looked down on her most recent acquisition. Piled in a naked heap on the mattress, he was well past any consideration one might give a man, Dianna thought. Anna and Siobhan had shaped his deviant tendencies into a full-on addiction that they fed judiciously. He was always compliant, got hard quickly and above all, lived to please his female owners.

Dianna pulled a chair from the shadows and sat down facing the sub. She hiked her skirt up to her waist and spread her legs wide. Conner watched her movements furtively, like a dog waiting to be fed or reprimanded. With Dianna, it was impossible to know what to expect.

"See my pussy man-whore? If you're a good pussy licker and I cum in the next 15 minutes I might let you squirt too. Get busy bitch." Dianna leaned back expectantly. Conner crawled across the floor. He ran out of chain about eight inches from her. Dianna smiled and shifted her hips enough to let the sub almost reach her with his tongue.

"Try harder sub, fourteen minutes left." Conner struggled to lick the pussy just inches away. His tongue protruded and the chain grew taut. Out of compassion Dianna allowed the tip of his tongue to reach her slit. She watched him struggle for a few moments, desperately trying to reach her pussy. She was fascinated by how horny watching him struggle made her, then she sighed and allowed the pathetic sub full access.

The sub buried his face between Dianna's almost anorexic thighs. She closed them around his head. Her hips tilted upward and she shrieked when he found her clit.

"Lick bitch! Oh my god, I knew you could lick pussy! Use your tongue. Faster slut! Lick it faster! Stick your ass up!"

Conner raised his ass in the air and licked the shaved, milk-white pussy. Acting on intuition, he sealed his lips around Dianna's slit and sucked. The thin blonde woman jerked and squealed with pleasure.

Dianna shoved Conner away impatiently. "Cock!" She demanded. Conner leaned back and thrust his caged dick forward. In a minute Dianna had the cage off and the stiffening cock in her mouth. She didn't understand why, but sucking cock always made her wetter.

The fuck-tool thickened in her throat. Her tongue traced its length back and forth. She could feel the head in the back of her mouth as the boner sluiced in and out. Her lips nestled at the bottom of his erection then tightened along the shaft, sucking the stiff prick from base to tip.

Conner felt it coming. There was no way to stop the massive discharge that had been building in him for days. Without permission, Conner's cock exploded into Dianna's mouth. Cum drooled from the corners of her lips but she did not swallow.

Instead Dianna held the cum in her mouth. She grabbed Conner's head in both hands and tilted it back. She forced his lips apart with her tongue, and opened his mouth wide. Conner's own cum flooded into his mouth and he had to swallow.

"Good cock," Dianna observed. "Now get some rest. I need my whore alert and able to follow instructions." Exhausted and at least temporarily satiated, Conner crawled back to his mattress and collapsed.

Dianna shut the light off and locked Conner's cell. She would let him sleep for a few hours. Her guests would want time to mingle and catch up on some hearsay before exploring the new sub in detail.

..........

Siobhan and Anna checked into the small island hotel. Everything in the foyer seemed to be made of bamboo or coral. They were booked into a suite overlooking the ocean for seven nights. The beach extended for kilometres and was available exclusively to the guests of the hotel.

"Follow me please," a young Caribbean man wearing only a red satin thong scooped their bags and set off down a well-used trail. He moved easily, the muscles in his back and buttocks flexed and relaxed as he led the women toward their accommodations.

"My name is Jason, I will be at your disposal during your stay with us. The rest of the staff will be pleased to assist you in any way they can, but I am assigned to you personally. I am available for anything you might want. Anything, anytime, day or night."

Jason carried their bags inside and stood waiting by the door. Siobhan tucked a twenty dollar bill into his thong and ran her hand along the obvious boner Jason had grown during their short walk. She continued to trace its outline idly with her fingers while she spoke.

"Thank you Jason. That will be all for now. Bring us a bottle of descent champagne now, then come back later this evening. We may have a use for you by then." Shiv smiled and stopped petting Jason's hard-on.

Jason stood erect, his hands clasped behind him, respectful and not overstepping his rank in the social order of the resort. "Thank you ma'am. Please call the pager number you were given at checkin whenever I can be of service. I will be close by and available for anything."

"Yes, I believe you will be able to provide the kind of services we are accustomed to, Jason," Shiv replied.

The women watched Jason's muscular ass depart. Shiv resisted the impulse to smack it. There would be lots of time for that amusement after she and Anna had their priorities straight.

"You didn't tell me this was a sex resort," Anna accused Shiv. "I'd have packed even less if I'd known." Anna smiled and pressed her body against Siobhan. "But you didn't allow me to bring much anyway. Just a couple of thongs and a T shirt. Are we going out anywhere while we are taking this well-deserved break?"

"The resort will supply everything we want, and you may not even need the things you brought." Shiv kissed Anna full on the lips and stood back. "In fact you won't be wearing anything at all most of the time."

"Take your clothes off baby. I want to see you naked as much as possible during our stay here." Anna stripped on the spot and left her clothes in a pile. Jason could pick up after them later.

"Stop! Leave the thong on. I'll finish unwrapping you when I want to," Shiv grinned. "Come."

Anna drew closer to Shiv slowly, a little apprehensive now that she found herself on the bottom end of the Domme/sub divide. Shiv watched her former mentor approach. Barefoot, tits quivering, Anna's hips swayed seductively with every step she took. Her adoring eyes never left Siobhan's face. So much had changed since she sat with Anna that first day discussing the most effective way to train Conner.

"Stop. Spread your legs and stick your ass out." Anna turned and spread herself for Shiv. Her shapely ass curved invitingly. With her hands braced on her knees, Anna's swollen pussy was just discernible through that special space that some women have where their thighs meet their asses.

Siobhan slipped her hand between Anna's legs and felt the sudden wetness that signalled her girl was ready. Anna moaned and pushed back against Shiv's searching fingers. With two fingers buried to the knuckles in the soaked pussy, Siobhan used her free hand to reach around Anna and harden the sensitive nipples that protruded from her large breasts.

"I think I don't want you wearing anything for the rest of the week," Siobhan whispered. "Just watching you walk around naked is making me wet." Siobhan pressed herself against Anna's jutting ass and slid her hands down the taut stomach to her pussy. Anna leaned her head back and groaned. Shiv was making her feel things she had only guessed about before; things she imagined her subs felt.

An emotional wave of gratitude washed over her. Anna felt lucky and privileged to be the object of Shiv's affection. There was nothing she would not do for Shiv. Any act of servitude was a pleasure for her to perform. This must be some of what her subs felt for her. She was both vulnerable and secure in Siobhan's arms. Anna had finally found her own mistress.

........

Back at Dianna's spacious country house, guests were arriving. A few of her closest collaborators had been invited for an evening of social and sexual intercourse. Word had spread among the loose network of women that a new sub would be on display.

As the evening moved into gear, the music changed from subdued classical ambiance conductive to conversation and reflection to a louder, distinctly sleazy beat more suited to stripping.

A spotlight snapped on, revealing a nude man crouched on the floor, arms hugging his bent knees, chest folded against his thighs. The man uncurled as the music played. His arms rose above his head and his body swayed slightly to the bump and grind stripper music. A long chain connected Conner's collar to Dianna's wrist. She tugged abruptly on the chain.

"Dance, whore."

Conner pumped his ass in time to the beat, turning slowly to display his erect cock and butt-plugged hole to the audience. The stiff cock bounced invitingly as Conner kept time to the music.

Conner knew he had to ingratiate himself to his handler. He sank to the floor and slithered on his stomach toward Dianna, ass in the air, mouth open suggestively. She enjoyed humiliating him. Surely she would take pleasure in humiliating him in front of her friends.