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Story 1 - The Very Best Night


Serious Mistresses


The Very Best Night

She hadn’t told him where they were going, but it didn’t take him long to figure it out on the basis of the first few turns she told him to make. Northbound on the interstate, on a Saturday afternoon when Caitlin was clearly in the mood to play, almost always meant that they were going out to the old farmhouse. And Ron, relaxed behind the wheel and driving the familiar route almost automatically, said nothing aloud but permitted himself to slip into a mild reverie of speculation about what his beloved wife and honored Mistress might have in store for him when they arrived. The farmhouse was pretty isolated, cut off from the neighbors by carefully cultivated hedges of trees, and it had a big, deep cellar. Big, deep, and well equipped. In their little condo in the city Caitlin could stretch him out naked on the bed, tethered at wrists and ankles with ropes or leather cuffs, and torment his shaven chest with drippings of hot wax until she had to gag him to avoid alarming the retired accountant who lived next door. But the farmhouse cellar was the place where she could bend him over the custom-built wooden bench and go at him with a cane that made a good, satisfying crack as it came down on his bare ass. And there was nobody on the other side of the wall to hear him squeal, or beg Caitlin to stop, just stop for a minute and I’ll do anything you want...


He blinked. “Yes, ma’am?” That was how he had to talk to her in private.

“You’re getting hard. You’re not anticipating something, are you?” Yes, it was true; the little bulge between his legs had to be pretty obvious. It had been a while since she’d permitted him sexual release, almost a whole week of stroking and licking and penetrating her with dildos while his poor penis went almost completely neglected, and thoughts of dim cellars and swishing canes were guaranteed to get him going.

He glanced at the passenger seat and returned her amused smile. “Somehow I got the crazy idea that we might be going out to the farmhouse.”

“Oh, we are,” she almost purred, crossing and uncrossing her slender, pale legs. “And I’ve got plans for you, of course – but not the same plans as usual. Fair warning.”

“Sounds good,” he laughed. “I usually seem to like your surprises, ma’am.”

She rested her hand lightly on his arm, and her tone became a bit more serious. “I know you do. That’s probably because I usually make an effort to surprise you in ways that I think you’ll like. This time might be different.”

“May a slave ask why?”

“Because this is something I’m doing just for me. I don’t know whether you’ll enjoy it or not. Like I said, fair warning. But until we pack up and drive home tomorrow, I’m not going to be worrying a whole lot about what you like and don’t like. Understood?”

Now that was unusual. If Ron had a complaint about Caitlin, it was that she was too concerned about his sensibilities when she used him as her slave. In their day-to-day married life, that was fine, even essential. But he wished that just once in a while, in the depths of the cellar or even the partial privacy of the bedroom in their little condo, she could bring herself to forget about his pleasure and treat him with the indifferent, selfish sadism he had always craved. Caitlin was wonderful in so many ways, but when she had him naked and at her mercy she was just too damn nice about taking advantage of the situation. But now her face looked as stern and serious as he’d ever seen it, and the way she’d drawn her dark brown hair back into a tight bun made her seem downright severe.

“Understood, ma’am,” he said aloud.

“And you’ll be on your best behavior, or I’m going to make you really sorry. As in no Yankees tickets this season.”

“Yes, ma’am.”

“Good. Good boy.” They were on a nice straight stretch of road, and she didn’t hesitate to slip her arm around him and kiss his cheek, just the way any wife might kiss her husband in the middle of a Saturday afternoon drive. “I’m glad I own you, Ron. And who knows, you might have the time of your life this evening. Now drive.”

He knew that meant she expected him to keep quiet until spoken to, which was fine. He wanted to ask questions, of course, but it was never possible to get much out of her when she wanted to surprise him in any case. So they drove in silence along the interstate for a while as the miles clicked by. Ron would have liked to put in a CD, almost anything with a good, pounding rhythm to it, but decisions like that weren’t his to make. Eventually Caitlin touched his arm.

“I’m going to try to get a bit of sleep. If I’m not awake by the time we get to Galver Springs, wake me.”

“Yes, ma’am.” He allowed himself to smile at her tenderly. “Hope you can rest a bit.”

“Thank you,” she murmured, and leaned back her seat and closed her eyes. Left alone with his thoughts of the cellar at the farmhouse, Ron drove along in a state of taut, eager arousal, and wondered what the love of his life had planned for him tonight. He was pretty sure he wouldn’t like it, or at least not all of it, but somehow the thought didn’t detract from his excitement in the least. The bench, the cane, the hiss of Caitlin’s breath as she laid on a good hard stroke...

Finally they turned onto gravel, and then dirt. Despite his best efforts to keep the ride smooth, Caitlin gave up and straightened her seat with a grimace well before Galver Springs.

“Did you manage to get to sleep, ma’am?”

“Not really,” she replied with a yawning smile, “but it still felt good. Straight on to the farmhouse, dear slave and husband, and prepare for a surprise. And remember, best behavior.”

“Sounds like you’re planning to put me through the wringer tonight, ma’am,” he said hopefully, unable to resist.

“Drive, Ron. And sit up straighter. Best behavior starts right now.” He obeyed, intrigued and excited and just slightly apprehensive. It was unusual for her to keep him on such a short, strict leash, or to give instructions in that peremptory tone. But he didn’t mind, exactly, and he was very much aware of his erection as he took them through town, over the bridge, around the corner, and up the long dirt driveway – really more of a private road – that led up to the farmhouse. Caitlin gave a wide, satisfied smile as he drove through the gate and braked so abruptly that they both jerked in their seats. It had been instinctive. A big blue truck was sitting right there at the end of the driveway, exactly where Ron normally parked. Somebody was waiting for them.

He turned to Caitlin, breathing hard and suddenly very nervous. She had never asked, or expected, him to act as her slave in the presence of other people. Only for her had he ever knelt with bowed head and hands clasped behind his back, or offered his nudity to the cane and the flogger. She had threatened, once or twice, to “introduce” him to old playmates she had known long before she ever met him, but he had always been sure she wasn’t serious. Until now.

He didn’t dare say a word, or do anything at all except wait for her instructions. She got out of the car and stretched, taking a deep lungful of the clean spring air, and cast an irritated glance in his direction when he didn’t move.

“Out, boy. Don’t think I’m going to let you hide in there.”

He obeyed a bit sullenly. She didn’t seem to be in any mood for hearing him explain that he had only been waiting for her command, not trying to hide at all. He hurried to keep up with her as she started for the front door, and as she fished in her purse for the key he began to unbutton his shirt without really thinking about it. On these occasions the rule was that he was never allowed to enter with clothes on. He would strip off right there on the porch, even if it were snowing, and walk into the house as his wife’s naked slave. But today she reached out a hand and caught his wrist as soon as she saw what he was up to.

“Don’t do that,” she told him with a hint of sharpness. “Today you’re going to stay dressed until told otherwise.”

“How disappointing,” said a woman’s voice from somewhere behind them. “I was looking forward to seeing what’s inside those khakis.”

They both whirled around, and Caitlin had to fumble at the keys to keep from dropping them. The owner of the voice had apparently been sitting under the big beech tree in what they thought of as the front yard of the farmhouse, or hiding behind it. Ron’s first impression was of a big, confident woman, not tall but fairly heavily built and broad at both the hips and the shoulders. Something about the way she carried herself, the slow but purposeful stride of her walk and the upright bearing of her torso inside her well-worn leather jacket, suggested an almost unnerving degree of self-possession and natural authority. There were wrinkles around her eyes and gray streaks in her casually tied back dark blonde hair, but it was hard to say exactly how old she was. A fair bit older than him and Caitlin, though. He didn’t know who she was or exactly why she was there, but she looked somehow familiar, as if she were one of Caitlin’s friends he might have met in passing at a party years and years ago.

“You heard her, Ron,” said Caitlin hurriedly. “Take your clothes off.” It occurred to him that Caitlin was deeply intimidated by this strange woman, maybe even a bit scared of her, and Ron couldn’t say that he blamed her. But she interrupted before he could resume his unbuttoning.

“That’s not what I said,” she noted mildly. “I was just expressing regret at having to wait. But it’s your boy, Cait, and your house. You get to decide what he does when.”

Caitlin smiled wryly. “It’s my boy and my house,” she admitted. “But aren’t I still your girl?”

They looked at each other for a minute, all three of them, and then the woman gave a shrug and an easy smile. “Okay, if that’s the way you want this to work.” She rested a hand on Caitlin’s shoulder as Ron looked on uneasily, wishing he knew exactly what they were talking about. “But the stripping can still wait,” she continued. “You can start by introducing us, for one thing.”

“Of course. Gladys, this is my husband Ron. Ron, my old friend Gladys.” Caitlin gave a nervous smile. “You’re going to get to know her pretty well over the next few hours.”

Gladys didn’t extend a hand to shake, so Ron didn’t either. “Nice to meet you, ma’am,” he said carefully.

She laughed. “Nice to meet you, Ron. Heard a lot about you.”

“But where –“ he broke off and swallowed hard as he suddenly realized he knew where he’d seen Gladys before. The image sprang into his mind with perfect clarity; an old photo Caitlin had once shown him late at night when she’d been a bit drunk and in the mood to shock him. In the foreground had been Caitlin herself, on her knees with her head bowed and her hair tumbling around her shoulders so that you could hardly see her face. She had been wearing a few – a few accoutrements, Ron supposed they would have to be called, but no clothes. Her lean, pale body had been shaven clean from the neck down. And sitting behind her, in a chair, with all her clothes on and a hand tangled up in the hair at the back of the young, naked Caitlin’s neck, had been – this woman called Gladys. “You were Caitlin’s mistress,” he said softly. “Before I met her.”

Gladys smiled and stretched her arms lazily. “I’m glad my reputation has preceded me. Yes, I was your wife’s first mistress – she had a couple of others, before she realized that what she really needed was a man she could dominate and bring to heel. It was so kind of her to offer to share the fruits of her labors with an old acquaintance.” She stepped close to Ron, her eyes never leaving his face, and slowly caressed one smoothly shaven cheek. “I keep a couple of girls at home, but I don’t get to play with a boy very often. I can’t seem to get male slaves to stick around – I think I’m too hard on them, or something. Too demanding.”

Ron took a deep breath and glanced at Caitlin. “You mean you’re – offering me to this woman?” He wasn’t sure whether he liked the idea or not.

“Yes,” said Caitlin shortly, as if she were suddenly having doubts of her own. “It would be inhospitable of me not to share. And besides,” she added in a lighter tone, “I want to show my old mentor that I have what it takes to whip a man into shape.” She swatted him, lightly, across the buttocks, and he lowered his head. Gladys laughed and gave his cheek a rough pinch.

“Is that a blush, slave boy? Ashamed of being shown off like a prize mule? Cait, I think you’ve got him right where we want him. I’m impressed already. And it’s good to see you, girl.” And she pulled Caitlin into a close, tight hug. Ron watched out of the corner of his eye as the women kissed, not quite like lovers but not quite like old female friends either, and finally turned back to him with Gladys’ arm still around Caitlin’s shoulders.

“Do you want to strip him and get him started on dinner?” asked Caitlin.

“Yes, I do. Ron, face forward, legs slightly apart, hands behind your head. Chin up – that’s it.” He obeyed quickly, before he had time for second thoughts. Gladys gripped him by the chin, her grip firm but not exactly uncomfortable, and turned his unresisting head from side to side. Her spread fingertips prodded at his chest, then his belly, then even lower. She was very close to him, and the clean smell of her hair was intoxicating.

“I’ve let him get a bit soft around the middle,” said Caitlin with an air of mild apology. “It seems to be tougher now that we’re in our thirties.”

“Actually, I was just thinking that you had a pretty nice, trim slave on your hands. And eager, too. Just feel how hard he is.” Ron gasped as Caitlin’s hand reached between his legs from behind and grabbed his balls through his pants, teasingly, before exploring further. His wife laughed softly against his back.

“It’s been a while since she let you come, hasn’t it, Ron,” said Gladys coolly.

“Yes, ma’am,” he almost whispered.

“Well, maybe we’ll let you come tonight. If you behave. Would you like that?”

“Of course, ma’am.”

“What if I made you lick it up?”

He started to lower his head, but she pushed his chin back up, mercilessly. “Even if you made me lick it up, ma’am,” he said. Damn it, he was blushing again. But her laughter was easy and not at all cruel, at least for the moment.

“Maybe we’ll have to see about that later. But right now…” She started unbuttoning his shirt, the task he had not been allowed to complete. The chest beneath, like his thighs and his ass and his face, was clean shaven; Caitlin liked the coarse black tufts at his armpits and groin, and allowed him to keep his shins and forearms hairy for the sake of appearances, but everything else had to be smooth for her. He lowered his arms a little so Caitlin could pull his shirt off from behind, and was grateful for Gladys’ smile of approval when he put them back in position afterwards. Caitlin reached around his body and took hold of each nipple, not pinching hard but rolling and kneading them. He sighed and relaxed back against her as Gladys unbuttoned his pants and pulled them down to his thighs.

“Help him out of those, will you, Cait?” And Ron, even though he knew what Caitlin and this Gladys had once been to each other, was amazed when Caitlin obediently dropped into a crouch beside him and drew the pants all the way off his legs, and helped him out of his shoes and socks while she was at it. He was standing there in his underwear in the cool sunlight of early spring, and the stiffness of his erection was only too obvious.

Gladys gave it a playful swat. “I think I’m going to enjoy you, Ron. Let’s see what he’s got under there.” Caitlin was already back on her feet, but she got down again to pull his boxer shorts down his thighs and off. Gladys took hold of his cock, handling it like a curiosity pulled out of somebody’s dusty cabinet, and stroked her fingers slowly along the shaft. He moaned and pressed against her, and she swatted him across the mouth with her other hand. Not hard enough to hurt at all, but a definite warning.

“Ron. Hold still and shut up.”

So he bit his lip to keep from moaning again as she played with his cock a bit more, and kneaded his balls in the palm of her hand, very gently at first but then hard enough to be just a little bit painful. Caitlin got bored with teasing his nipples and drew her nails down each of his unprotected flanks, and then back up so slowly and firmly that he had to bite his lip again. Finally Gladys gave him a cool smile and slapped his balls with her open palm, a lot harder than she’d hit him across the mouth. He gave a grunt of pain and jerked forward, not quite doubling over, but he kept his hands in place on the back of his neck – that was something, at least. But hell, that had really hurt, and he hadn’t been ready for it at all. Gladys’ smile hadn’t changed a bit, and he wasn’t sure whether or not she was going to hit him again. He was surprised, though, when she grabbed him by the hair and kissed him full on the lips. But hey, it beat being slapped in the balls, and he kissed back eagerly. She rolled her tongue around the inside of his mouth a little before pushing away.

“Yeah, I’d say you got a nice one,” she told Caitlin over his shoulder. “Cute, well-behaved, just a little bit scared – exactly the way I like them. Why don’t you go in and figure out what he’s going to make us for dinner? Slave and I will be along in a minute.”

“Oh, it’s taken care of.” Cait sounded flustered. “I mean, I already –“ Gladys raised her eyebrows, and she broke off. “Oh, okay,” she said meekly, and disappeared into the farmhouse. Gladys gave Ron another of those gentle slaps on the mouth when he started to turn his head to look after his wife.

“Ron. I want your attention.”

“You’ve got it, ma’am,” he replied fervently.

“Good.” She hesitated for a moment with pursed lips, and then met his gaze evenly. Her eyes were almost disturbingly blue, like polar ice. “Are you sure you’re okay with this, Ron? If you’re having any misgivings or second thoughts, I want to hear about them now.”

He started to look down, but she pushed his chin up a bit more roughly than before. “I won’t pretend I’m not scared, ma’am,” he said carefully. “But yeah, I’m okay with it. If my Mistress trusts you, then so do I.”

“Tonight I’m your mistress, Ron. And I’m glad you’re scared. You should be.”

“May I ask a question, ma’am?”


“Were you serious when you said you were too hard on male slaves to be able to keep one around?”

She looked surprised for a minute, then laughed, a gusty belly laugh that Ron couldn’t imagine coming from Caitlin. “Let’s just say that when a guy invites me to tie him down and hurt him, I take him at his word. And if he really meant that he wanted me to wrap a silk scarf loosely around his wrists and give him a few gentle love taps, he’s in for an unpleasant surprise. You can think about that while you’re serving our drinks and making dinner. Any more questions?”

He tried to think of one and couldn’t. “No, ma’am. I’m ready.”

“We’ll see about that. Hands down, and get inside. It’s time to put our slave to work.” She held the front door open for him, like a guard taking some hapless prisoner into custody. And he wasn’t really surprised when her free hand came down good and hard on his ass as he walked past her, like a promise of things to come.

* * *

Maybe three hours later Ron found himself seething with impatience, frustration and something like jealousy as he loaded up the dishwasher and cleaned out by hand the pots and pans that were too big to fit. The women had been talking and relaxing together all evening, and essentially ignoring him except when they wanted a glass refilled or a dish cleared away. First had come the before-dinner drinks, a beer for Gladys and white wine for Caitlin, which they sipped on the porch as they watched the sunset. He had been sure they would call him out there to tease him or smack him around a little sooner or later, and he had been half looking forward to it, but they’d seemed quite happy to keep each other company while he played Naked Chef in the kitchen. Their cheerful voices had drifted in to him from outside, along with a lot of laughing, although at one point he’d thought he heard smacking noises followed by whimpers of pain that sounded like they were coming from Caitlin. Half fascinated and half horrified, he’d just been working up the nerve to sneak into the living room for a bit of eavesdropping when a sniffling and tear-stained Caitlin had marched in on her way to the bathroom and caught him hovering around the kitchen door. She might not have slapped him quite so hard, Ron reflected, if she hadn’t noticed his erection and no doubt realized that the image of Gladys working her over was not one that he found entirely unappealing. After that he’d stayed in the kitchen like a good slave, even asking permission when he had to go urinate.

Then it had been time for dinner. Again, Caitlin had given him reason to get his hopes up, this time by telling him to make enough beef stroganoff for two – but generous portions, so that they could feed him scraps if they wanted. Despite the humiliation, he had rather looked forward to kneeling naked by the dinner table, accepting the occasional mouthful from the women’s forks. Attention was attention. But when he’d had everything served and arranged just the way Caitlin liked it, they’d still been too absorbed in their own conversation to want him around, and he’d ended up eating a meagre portion alone in the kitchen after they’d taken what they wanted and sent him away. Sure, their dismissive attitude made him feel enslaved and humiliated, but it also made him feel ignored and taken for granted. Couldn’t Gladys see how eager he was to serve her, to suffer for her, to show that Caitlin had made him into a good slave? But the worst had come when they’d gone down into the basement without him. As far as he knew, they were still down there now. The floor was too thick for him to hear anything, but he was almost sure that Gladys was playing with Caitlin down there, reliving old times while he went neglected. Hell, he wouldn’t be surprised if Gladys and Caitlin spent the night in the master bedroom (or mistress bedroom, as Caitlin liked to call it with one of her mischievous grins) and made him sleep out in the old barn. He’d be cold, alone, frustrated, and he’d have to think of Gladys’ strong hand roaming over Caitlin’s breasts, her lips pressing down hard on Caitlin’s as blonde and dark brown hair tumbled together on the pillow –

“Hurry up,” said Caitlin from behind him, and he jumped and almost dropped his grandmother’s best platter. When he glanced over his shoulder he saw to his astonishment that his wife was almost naked, dressed only in a little red halter and a matching thong he hadn’t seen her put on in years. Not since the first year of their marriage, actually, when dominance and submission had just been a game they played once in a while. But she had it on now, her hair was long and lustrous and unbound, and she looked sexy as hell. She was carrying a leather collar and a pair of handcuffs.

“What on earth are you wearing!” he exclaimed, too astonished to address her properly. But she let it go.

“I’m dressed the way Gladys wants me to be dressed. Just like you, slave. Now finish with the dishes. We’re ready for you downstairs, and believe me, she doesn’t like to be kept waiting.”

He returned a share of his attention to the platter. “You mean you were setting up down there, ma’am?” he asked with a glimmer of hope.

“Naturally,” she replied with an amused smile that said she knew exactly what he’d been worried about. “We’ve got plans for you tonight.”

“Is she as tough as she says she is? Demanding, I think that was the word.”

Caitlin shrugged, which made her taut little breasts do interesting things inside the halter. “When I belonged to her she handled me the way I try to handle you – firm, but affectionate, and lenient as long as I was showing some basic respect. When she was working me over, she was usually pretty playful, and always careful about not laying it on too hard and making me take more than I could deal with. But that was with me, and her other girls. I’ve never seen her with a man, but I hear she really gives them hell.”

“And you don’t have a problem with that?” he asked quietly.

Caitlin stepped close and put her hand on his shoulder. The other still held the cuffs and collar. He could feel the warmth of her bosom and the smooth fabric of her halter against his naked back. She was tall enough that it wasn’t hard for her to speak almost directly into his ear.

“Ron,” she murmured gently, “It’s not just that I ‘don’t have a problem’. I’m looking forward to watching her give you a taste of hard, ruthless domination, and I’m going to help. And don’t pretend that you aren’t looking forward to it just as much. Or are you erect just because you need to piss again?”

“Touche, ma’am,” he laughed. “I’ll admit to a certain curiosity.”

“The minute you finish the dishes, Ron.”

“Actually, that platter was the last thing, ma’am.”

“And you’re ready?”


“Okay. Here, turn around a minute.” She set the restraints down on the kitchen table and pulled him into a close, tender embrace. For just a moment, as her arms twined around him and the softness of her nearly naked body pressed deliciously against his own bare skin, he could almost forget that he was her slave. What was it about the scent of a woman’s hair that always drove him so crazy? He pressed his mouth to hers, impulsively, and she returned his kiss with the kind of warmth and ardour that usually meant she wanted him inside her. His penis was sandwiched between their bodies, hot and hard against the taut smoothness of her belly.

“I love you, Ron,” she whispered. “But I’m going to hurt you.”

“I love you too, ma’am. And I can’t wait.”

She pushed back and eyed him at arm’s length with a small, amused smile, still holding his elbows. “You wouldn’t be so eager if you knew what Gladys has planned for you down there.”

“Maybe not. But I don’t, so I am.”

“It will be a pleasure to show you what happens when a slave rushes in where angels fear to tread, Ron.” A note of command entered her voice. “When you’re ready, you can turn around, and put your hands behind your back.”

He obeyed at once. He swallowed hard and bowed his head as he felt her long, deft fingers take hold of one wrist and lock cold metal around it, then move to the other. Caitlin usually preferred rope or leather to the unyielding steel of handcuffs, but even so the sensation of being restrained by her was familiar and almost reassuring. He pulled against the cuffs, reflexively, and of course found that he was inescapably held. She moved in front of him and drew one fingernail up from the root of his penis to somewhere in between his nipples. Being touched like that felt so much more exciting, and dangerous, now that he couldn’t move his hands to protect himself even if he wanted to.

“Chin up,” she prompted, and buckled the collar around his neck. That was something else she didn’t use very often; she had pointed out to him more than once that she owned a slave, not a dog. But it made him feel very helpless and subservient to be led toward the cellar stairs by the neck, erect and nude and utterly docile in the restraints Caitlin had put on his body. He let his eyes drift across the smooth expanse of her back and the lean curves of her thighs and buttocks as she drew him after her without a backward glance, her hand firm on the leather grip at her end of the leash. There was a moment’s pause as she opened the cellar door, and then they went down.

He had braced himself for the usual chill, but tonight the cellar seemed warmer. It took him only a second to see why. Among their preparations had been the suspension of a big, bright lamp from a rafter, so that it shone down like a spotlight in the middle of the large open space that served as Caitlin’s private torture chamber. And the light wasn’t the only thing hanging from the ceiling there. Two steel manacles dangled at the end of heavy chains, roughly above two of the steel rings that Caitlin had set into the concrete of the floor a long time ago. She had pinned him down spread-eagled on the floor, a few times; but now a prisoner could be led into that circle of blazing illumination and chained with his legs spread wide and his arms stretched up above his head. He would be exposed and vulnerable from both the front and the back.

Gladys stood near the hanging manacles with her arms folded across her chest and a wide, pitiless smile on her face. He had half-expected her to be decked out for the occasion in some fantastic costume of studded black leather, but in fact she was wearing the same casual clothing she’d had on outside, except that – ironically enough – her leather jacket had disappeared as a concession to the warmth of the room. But her sleeves were rolled up, a long-handled riding crop was stuck through her belt, and she looked ready for action. At a peremptory signal of her hand Caitlin led Ron forward, into the light.

“I think you could take off the cuffs and collar. He’ll behave without them, won’t he?”

“He’d better.” Caitlin unbuckled the collar, and went around behind him to unlock the cuffs. He kept his hands clasped behind him anyway, not knowing what else to do with them. Gladys looked him up and down consideringly.

“Hi there, Ron. Scared yet?”

“Yes, ma’am. And turned on.”

“We can see that,” giggled Caitlin. “Not that we’re planning to do anything about it for the moment.”

“Right,” Gladys confirmed. She pulled the crop out of her belt and slashed it through the air, hard enough to make Ron wince at the menacing whistle. “First things first. Anything you want to say before we get started, boy?”

“I think I’m ready, ma’am,” he murmured, looking down at her boots.

“If that’s the best he can do, I don’t know why we’re letting him talk at all,” Caitlin pointed out, archly.

Gladys shrugged. “We don’t have to. Why don’t you pick out a gag for him?”

“My pleasure,” Caitlin purred. She only had a couple of gags, which she kept hanging among what Ron thought of as her small and diabolical tools of domination – the clamps, the ball stretchers, the thumb cuffs. She lifted down what they both knew from experience was the more effective of the two, a leather band with a big red ball to go in his mouth, and extended it toward him. “Here, put this in. I want to watch you do it yourself.”

Ron hated gags. He got scared, almost panicky, when he couldn’t talk about what was happening or even moan properly in pain. He glanced uneasily from one woman to the other and decided to risk a respectful protest. “Please, ma’am, you know that I –“

He was looking at Caitlin, so he saw Gladys’ hand come up at only the last second before it smashed across his cheek – not a little warning smack like the ones on the porch, but a real full-armed slap with a lot of her strength behind it. He yelled in surprise and pain as Caitlin moved behind him and grabbed his elbows, not so much holding him in place as reminding him to keep still and not try to pull away or defend himself. Gladys hit him again and then grabbed him by the hair.

“I think there are a couple of things we need to get straight, Ron,” she hissed.

“Please, ma’am, I didn’t mean –“

“Shut up and listen.” He swallowed hard and fell silent. “Good,” she continued, though her voice was still harsh. “First thing. From now on tonight, Cait is Ma’am and I’m Mistress, as far as you’re concerned. Got it?” She slapped him again, as if for emphasis, and he cried out and felt tears well up in his eyes.

“Yes, Mistress,” he gasped.

“Good. Second thing. When either of us gives you an order, you carry it out immediately. No hesitation, no questions, and especially no backtalk. Got it?”

“Ow! Yes, Mistress.” But she slapped him again, and again, and then grabbed his nipples in her two hands and gave them a hard, sudden twist. His body jerked involuntarily, and he felt Caitlin’s hands tighten warningly until her nails dug into the soft skin of his upper arms.

“Please, Mistress!” he whimpered. “I understand – I’ll do what you tell me –“

“Damn right, Ron.” Her fist drove into his belly with considerable force.

“Ow, please! I’ll put in the gag – I’ll do anything…”

“Yeah? You ready to prove it?”

“Yes, Mistress!”

“Okay. Let him go, Cait.” Again, he kept his hands behind his back as he stood there naked and trembling, now really frightened. It wasn’t so much that Gladys had hurt him – he’d taken worse from his wife in this very cellar, plenty of times – as that she had handled him in a cold, relentless way that shook him to his core. Even when Caitlin was making him literally scream in agony under her cane or her flogger, she never quite let him forget the love and affection that went along with her ownership of him. Gladys just wanted to make use of a convenient male toy.

“First, you can go ahead and put in that gag.” He crouched down to pick it up and slipped it into his mouth, hating everything about it – the taste of the rubber, the uncomfortable spreading of his jaws, the undignified drooling. Caitlin buckled it behind his head, tighter than he remembered her doing it last time.

“Now, if you’d just done that in the first place, we’d have gone ahead and strung you up,” Gladys explained conversationally. “But you seem to need a little lesson about obedience first – isn’t that right?” He nodded, afraid to do anything else. “Clever boy. Go pick out some clamps for your nipples. A pair that will be good and painful.”

Caitlin loved nipple clamps, and she had an extensive array of them. Big and small, light and heavy, with serrated jaws and smooth. But there were only a few sets that she actually used on him more than occasionally. He went without hesitation to the ones she usually selected when she was in the mood for severity, unpleasant little things in which a small screw pressed the captive nipple against jagged metal. With the screws fairly loose, the clamps were merely quite uncomfortable, but they could be tightened until the pain was agonizing. Ron took them in the palm of his hand and went back to stand before Gladys.

“Put them on,” she said coolly, as he’d expected. He braced himself and screwed the left one into place, then the right. He hesitated only a moment before tightening each of them a couple of good twists beyond the loosest setting that would hold, though he whimpered into the gag as he did so. Gladys inspected them critically, and lifted one with her finger only to drop it again a second later. He groaned and bit down hard as his nipple took the sudden weight.

“What do you think, Cait?” His wife came around in front, not hurrying, and tugged experimentally at the other clamp.

“He can take worse than this. Three full turns worth of worse, I’d say, ma’am.”

Gladys smiled briefly at the formal address, though it seemed to have slipped out without Caitlin noticing. But her attention never really left Ron. “Then I’ll give you a choice,” she told him. “We can make it only two turns, but you have to do them yourself. If we have to tighten them, it’s going to be three. You have to decide right now, of course.”

Three wouldn’t be a lot worse than two, and being made to inflict pain on himself possibly ranked a step or two below being gagged on his list of submissive delights. Ron very deliberately put his hands behind his back, though the gag couldn’t stifle his moans as the women took hold of the clamps and twisted the screws tighter, Caitlin’s fingers gentle and deft and Gladys’ rough and firm. Sweat was trickling down his sides, from the heat and the fear and the pain. Gladys slapped him again, though not as hard as before.

“There, Ron, you like that? I think they suit you – honestly, a boy’s nipples aren’t good for much else. But the next part you have to do all by yourself. Go get the biggest of those butt plugs. Cait, I’m surprised you don’t have anything even larger, to really stretch him. He might regret it later.” Ron wondered what she meant by that, but decided to ignore it as best he could and concentrate on doing what she’d told him. He walked over to the shelves, slowly and carefully so as not to make the clamps swing, and picked up the butt plug. At Gladys’ impatient nod he covered the smooth black rubber with lubricant from the bottle sitting nearby.

“You know where it goes, slave.” Indeed he did. He bent over, turning his ass toward them so that they had a good view of the proceedings, and slipped the greased up plug inside. Caitlin made him take it routinely enough that it went in easily, and the sensation of being filled and stretched was too familiar to be really disconcerting. He straightened up and put his hands behind him.

“See?” Caitlin laughed. “You can be a good boy when you try. Is that enough, ma’am?”

“Yeah, I think we’ve made our point. Ron, that’s my approach to discipline. You hesitate when I give an order, and I’ll make you do the same damn thing only worse. If you won’t put in the gag, then you get smacked around until you’re ready to put in the gag, clamp your nipples, and stick a plug up your ass. Understood?”

He nodded.

“Then we’ll get on with the program. Get over to centre stage and cuff yourself to the ceiling – not because I’m still making a point, you understand, but because Cait and I can’t reach.” That had almost been a flash of humour. Ron was amazed – but not so much that he wasted any time about stepping into the spotlight, reaching up above his head, and closing cold steel around first one wrist and then the other. It was almost a relief to be restrained like this, since it meant he couldn’t be told to inflict any further torments on his own body. They had judged it almost perfectly: with his arms fully extended, he could rest his feet comfortably on the floor. Except – yes, he could feel Gladys’ crop slip in between his thighs from behind, slapping gently, forcing his legs apart until his feet were close to the steel rings in the floor. This was harder to take, since he couldn’t quite rest his heels firmly on the ground. Caitlin crouched down and locked his ankles into place, then stood up and kissed him. His erection rubbed tantalizingly against the crotch of her little thong.

“This is where we get serious, Ron,” she murmured. “I hope you’re ready.” She stroked the hard shaft of his cock, slowly, with one finger. “You feel ready.”

He wanted to explain that he was responding to her proximity, not the prospect of pain, but the gag wouldn’t let him. And surely she understood anyway. His eyes followed her nervously as she went over to the rack of bigger toys, took down a cane, and flexed it between her two hands. At least this was a familiar part of their play, almost ritualistic. She started off in front of him, prodding his thighs and his balls with the tip of the cane, gently at first and then harder and harder. Gladys was still behind him, an unseen but menacing presence. He began to gasp and flinch away from the cane as Caitlin’s sharp little jabs became uncomfortable, and then painful. A hard jerk of his body shook the clamps, and he gave a high yelp of pain around the gag. Then, as if that first cry of anguish had been a prearranged cue – and Ron supposed it probably was – Gladys hit him from behind with her crop, right across the buttocks. He clenched hard, reminding himself not to expel the plug whatever happened, and braced for a second blow. But it didn’t fall, or not immediately. Instead, Caitlin put down her cane, and stepped forward. And kissed him again.

Gladys moved around to the front, her crop held casually in one hand. She stepped close, and again Ron braced himself, but it was toward Caitlin’s body that her free hand extended. Gladys unfastened Caitlin’s little halter and drew it away, leaving her small, firm breasts to spring free and brush teasingly against her husband’s chest. Caitlin kissed Ron and Gladys kissed the back of Caitlin’s neck, before giving her ass an affectionate little smack – but hard enough to hurt just slightly, Ron was sure – and prowling back around, out of Ron’s field of vision. Caitlin dropped a bit lower, grabbed one clamp in her teeth, and shook it until he gave his first full-throated scream of pain. That was the kind of half-playful, half-cruel thing she did all the time when they were down here. But now she was going lower still, until she was kneeling before him. And she leaned forward and closed her lips around the very tip of his penis, gently suckling and driving him crazy with the warmth and wetness of her mouth. Gladys’ hand caressed his back, firmly and possessively, as he pulled convulsively at his chains.

“That feels nice, doesn’t it, boy? And she promised me earlier that she’d keep doing it as long as you want, too – as long as you be a gentleman, and don’t go moving around on her. No trying to poke in deeper.” Oh, Ron had no intention of poking. Not when Caitlin’s mouth was working the head of his penis in exactly the way he liked, and slowly, ever so slowly, moving up the shaft to enclose more and more of him. No, he’d brace himself and hold still, and take the delicious sensation as it came, and try to forget about the stretching in his anus and the pinching at his nipples. And, for that matter, the increasing soreness of his arms and legs – but it all receded into irrelevance as Caitlin began to use her tongue in earnest, circling around and around until he was moaning in pleasure rather than pain for the first time that evening. And then Gladys hit him.

The crop came down across his shoulders, and he yelled at the sudden, surprising sting. But he didn’t move a muscle, and certainly didn’t buck his hips forward into Caitlin’s face. She kept sucking and licking, at her own pace, and he knew he was going to come if she sped up just a little. For once he was grateful for the gag, since it meant he clearly wasn’t expected to ask permission. He began to breathe faster, through his nose and around the gag – and then another blow, a really hard one, right across the back of one thigh. And then another. Damn it, couldn’t Gladys leave him alone for just a few more seconds? And of course she could, but of course she wouldn’t. Caitlin picked up the pace at his groin, leaving the shaft for a moment to cup his balls in one hand and kiss and suckle them with wonderful delicacy, but now he had that awful, relentless stinging from behind to keep him from concentrating properly on his wife’s attentions. Caitlin’s tongue wasn’t the only thing that was starting to move faster. The crop smacked his calves, then his thighs, then his ass before beginning to work its way back down. He moaned in pain and sheer frustration, and tears began to trickle down his clean-shaven cheeks. He couldn’t help it – he was so close to what he’d been waiting for all week, and yet Gladys and her damn riding crop were holding him back even though Caitlin was practically devouring him with her mouth, sucking and kissing and licking as if she really meant to bring him off. But it was getting difficult to hold still, under Gladys’ harsh rain of blows – and then he really screamed as the crop came back up to his ass suddenly, without warning, and hit him six or seven times in a hard series of blows without a moment’s pause between. He didn’t think Caitlin could have laid it on that hard and fast to save her life – Gladys had to be even stronger than she looked, underneath that plain white shirt. But the thought was disjointed, irrelevant, and the only thing that mattered was the pain. The only thing. With a yell of defeat he threw himself away from the next blow of the crop, and straight down Caitlin’s throat. And the crop, of course, hit him anyway.

“That,” said Caitlin cheerfully as she disengaged, “was not like a gentleman.” And he could have wept with frustration, if he hadn’t already been weeping with pain, as she stood up and gave him one final kiss on the face, her bare breasts still swinging free in front of her. Gladys had eased up a bit with the crop, but she certainly hadn’t stopped, and her blows were coming just as hard though not as quickly. She was concentrating almost exclusively on his thighs and ass now, and he was sobbing and twisting ineffectually away from every stroke. What did it matter now? But Caitlin grabbed his head.

“I want to hear him scream for mercy. We can’t really do that in the city.”

“Go for it,” panted Gladys, and whacked him across the left thigh. Caitlin reached around and unbuckled his gag, and tossed it to the floor. Sure enough, his scream echoed off the walls with the next blow of the crop, although he was determined not to actually plead for mercy if he could possibly help it. Actually, it wasn’t so difficult, not with the pain so overwhelming that he didn’t feel capable of formulating coherent syllables anyway. Caitlin flipped both his nipple clamps at once, drawing a loud moan of agony, and then picked up her cane and moved behind him. Oh, no. The crop hit his right and left buttocks – wham, wham – and then he heard the sounded he’d been dreading, the unmistakable authoritarian swish of the cane. It descended right across the welts Gladys had just made, and Ron screamed. Caitlin gave one of her delighted laughs as the crop went back down to his thighs and the cane followed.

“Ow! Mistress, ma’am – please, please stop hurting me! I can’t take – oh, ow! Oww!” And they were speeding up, too, collectively beating him much faster than a single person could have done alone. Crop, cane, crop, crop, cane. The hisses and slashes and swats became an indistinguishable cacophony, the pain melded into a fiery blur that seemed to cover his whole ass and spread a good part of the way down toward his knees. Like sitting in lava. Gladys got him really hard on the inner thigh with the crop, at a diabolically precise angle, and Caitlin laughed again at his cry of anguish. The butt plug had slipped half out, but he didn’t care. He just wanted to get away, to make them stop, to make them pause, to give him just a couple of minutes – he wasn’t sure whether or not he was screaming his pleas out into the room or merely in the privacy of his own mind. But then, blessedly, they stopped.

He was hanging in his chains, not standing. He seriously wondered if the cold liquid that trickled so copiously down the back of his legs was sweat or blood. He could hear the panting breath of the women as his own groans and sobs subsided into stillness, then a noise that sounded like it might be the two of them kissing.

“This,” said Gladys laconically, “is why I told you that it was okay for you to be scared. Here, let me help you with that plug.” He felt her firm hand push it back inside him, back into place. “Now, how are you feeling, slave boy?”

“It hurts, Mistress.”

“Yes. You’re handling it pretty well though, so far.”

“Thank you, Mistress,” he gasped, pathetically grateful for the note of mild approval in her voice.

Caitlin laughed, not unkindly. “For the beating, or the compliment? Maybe both?”

“Both, ma’am,” he replied. “And the oral sex.”

“Oh yes, the oral sex.” She came back in front of him and took his cock in her hand, just holding it. It had gone soft when the pain was at its height, but her touch and the proximity of her naked body – she’d lost her thong at some point, and he could see moisture glistening in the dark tangle of hair at the junction of her thighs – was enough to make it stiffen again instantly. She gave another soft laugh and slapped it gently back and forth. “There might be a bit more of that later. We’re going to give you a little break now – but first, a change of position.”

Gladys, still fully clothed, hauled over a chair for her to stand on – Caitlin would sometimes recline in that chair and give languid instructions as Ron did things to his own body for her amusement – and Caitlin stepped up to unlock his wrists. Gladys grabbed his arms immediately and pulled them behind his back, holding him in a tight, uncomfortable grip, as Caitlin bent to release his ankles. Caitlin took hold of one arm, and together the women led him over to the corner where Caitlin kept the high padded bench she liked to put him on for a good caning. It was very sturdy, and deceptively comfortable – lying face down on its soft upper surface, wrists and ankles held in place by soft leather cuffs attached to the sides of the bench, was almost pleasant, until the real fun started. Gladys pinioned his arms again while Caitlin took the clamp on his left nipple in a delicate grip.

“Ready, my slave?”

“Yes, ma’am.” He braced himself, but even so he couldn’t suppress a yelp of pain as the clamp came off and blood rushed back. She detached the right clamp immediately, not giving him time to catch his breath, and he was still gasping as they seized him and bent him forward over the bench. The leather cuffs felt nicer than the steel ones, more forgiving, but he was just as effectively confined. There was a little indentation at the back of the bench to let his genitals hang free, and he felt very vulnerable with his cock dangling in empty space and his ass sticking up in the air. Caitlin slapped it, hard – she could almost never resist. And then they released the brake on the bench, and wheeled it over into the spotlight. He could feel the heat on his naked back.

Gladys ruffled his hair, as if to remind him of his helplessness. “Okay, break time, like the lady said. Take a few deep breaths and try to pull yourself together. We’ll be back for you soon. And you,” she added, turning to Caitlin, “are coming with me.” Ron lifted his head to watch, aroused and just a little jealous, as Gladys took his naked wife in her arms and kissed her full on the lips. They held it for a good long time before Gladys disengaged, slung her arm casually around Caitlin’s shoulders, and led her away and up the stairs. Minutes ticked by, and he imagined the two of them naked together on the bed he normally shared with Caitlin, laughing, Gladys’ firm hand slipping down between Caitlin’s thighs as his wife moaned and writhed in ecstasy and he himself waited alone and helpless in the cellar…

He might have fallen briefly asleep with that erotic, distressing image still in his mind – he wasn’t sure. But his head jerked abruptly upward as he heard a commotion at the back entrance of the cellar, the one he and Caitlin always used to move heavy objects in and out. It was much easier than trying to go down the twisty stairs from the upper floor of the house. And sure enough, his two captresses appeared at the cellar door hauling between them a bench much like the one he was presently tethered to, only perhaps a bit smaller and lighter. Gladys must have brought it in her truck, but why? There wouldn’t be any reason to move him onto it, unless it had some diabolical secret property that he would discover painfully in due course. But he forgot all about it as the women pulled the second bench up more or less alongside him and turned to face their prisoner. They had both grown penises – or at least, they were wearing big, thick dildos of black rubber, accurately sculpted from circumcised tip to slightly wrinkled scrotum. Only their jet black colour, and their slightly disproportionate size, detracted from their realism. Caitlin was still naked apart from the leather harness that supported her new appendage, and even Gladys was bare to the waist. Her breasts were full and pendulous, a fair bit bigger than Caitlin’s but not so firm. She took Ron by the hair as they both walked up to him, standing so close that he could smell the fluids of arousal that were slick on Caitlin’s thighs.

“Coffee break’s over, slave. You can start by greeting us properly.” She pulled his head toward her dildo to show him what she meant, and he planted a small, tentative kiss on the tip. He wasn’t sure if it would be enough to satisfy her, but it was. She turned his head so that he could repeat the ritual with Caitlin.

“Thank you, Ron,” his wife laughed. “I think it’s about time you got some firsthand cocksucking experience. It might make you appreciate what I’ve been doing for you all these years.”

“But I don’t understand, ma’am,” he temporized, though his curiosity was genuine. “What’s in it for you?”

“Oh, it’ll rub nicely if I fuck your face hard enough. And then there’s the thrill of making you do it, of course. You can start right now.”

“Not quite,” Gladys interrupted. “Over here, little girl.” She took Caitlin by the arm, not roughly but with a certain firmness, and turned her so that she was facing off to the right, her left flank turned toward her husband. “Down,” said Gladys softly, and slapped Caitlin’s ass. Caitlin blushed, spread her legs, and bent over and grabbed her ankles.

“Good girl. Now hold still.” Ron watched in rapt fascination as Gladys positioned her dildo at the lips of Caitlin’s cunt and pushed in hard, holding Caitlin’s hips to steady her. Caitlin groaned and bucked and started to rise up, but Gladys’ hand came in sharply from the side and slapped her breast, reminding her to get back down. When Gladys pulled out, after only a couple of strokes, her dildo was wet and glistening.

“Please –“ Caitlin gasped. “Just a little more –“

“Not till you’ve earned it, my little orchid. You’re frustrated?”

“Of course, ma’am,” said Caitlin, a bit resentfully.

“It’s all right. You’re supposed to be. But you can take it out on slut boy there.”

“Yes, ma’am,” said Caitlin fervently, and slapped Ron across the face before dragging his head roughly to the tip of her cock. “Start slow,” she told him. “I’ll be coming in at my own pace, so be prepared.”

He made what he hoped would be interpreted as an affirmative noise around the thick, menacing black rubber shaft. Caitlin held him by the hair and stroked his face from time to time as he licked and sucked her, rocking gently back and forth and gradually pushing deeper and deeper into his mouth. He was going to gag when she got to the back of his throat, he knew he was, and he began to sweat and tremble in his restraints. He hadn’t realized sucking cock was such hard work, either – his jaws were getting sore from the strain of wrapping around that thing and working it with his mouth. So this was what it was like to be penetrated, to have to give oral pleasure without receiving anything in return. “Good boy,” Caitlin purred, as she sighed following a particularly hard push. “Good cocksucker.” That made tears of shame and frustration well up in his eyes. But he didn’t feel scared, exactly, until he felt Gladys’ gloved hands on his buttocks. They spread him wide, and he felt her fingers reach in deep for the butt plug, which he’d almost forgotten was there, and draw it out. He felt a moment of blessed, wonderful, relief, but then she spread him again. Panic welled up, and Caitlin had to give his hair a hard jerk to remind him to keep up his sucking and licking. Surely Gladys wasn’t going to… but yes, she was.

She didn’t bother to break him in gently. With his ass well stretched by the butt plug, and her cock good and lubricated with Caitlin’s juices, she didn’t have any problem pushing all the way in on the very first stroke. But God, it hurt – not nearly as much as the cane, he supposed, in absolute terms, but there was something awful about pain that came from the inside out. Suddenly he was really crying, with humiliation and the horrible sense of vulnerability as much as with the pain, and he tried desperately to squirm away from Gladys and her big, savage cock. The restraints at his wrists and ankles did give him enough slack to shift forward a few inches, but she caught him around the waist and dragged him back, holding him firmly as she drove in for another, even harder and faster thrust. He groaned around Caitlin’s dildo, wanting to plead with them, wanting to offer to stand back up and take another round of caning if only they would stop raping him like this. But he couldn’t say a word, not with his mouth full of black rubber. Gladys impaled him and rubbed around a bit, groaning in pleasure and making the dildo move uncomfortably inside him, and Caitlin drove hard into his mouth as if inspired. He felt the tip of her dildo at the back of his throat, hurting him and choking him, and sure enough he gagged and gasped around it.

“Not good, Ron,” she panted. “Going to have to see – that you get – ah – more practice.” She backed off just enough to let him take a quick gulp of air, and then pushed in even harder than before.

“Please!” he moaned, as she pulled away a second time, but she paid no attention. Gladys was going at him really hard, too, moaning and gasping, until suddenly she stopped moving and threw herself down on his naked back. She screamed and sank her teeth, hard, into the flesh of his shoulder. Had she really got herself off, just from the rubbing of that thing through her jeans and whatever she had on underneath? It seemed hardly possible, but then again, her dildo had gone still and quiescent inside him, and he could hear and feel her panting breath in his ear.

“One,” she gasped. “Cait, we’re trading.”

Caitlin pulled out, with a sound almost like a snarl, and slid into his anus as soon as Gladys was out of the way. She was a bit gentler than Gladys about entering him, but on the other hand his saliva wasn’t much of a lubricant. He hoped desperately that Gladys would at least wash the dildo before sticking it in his mouth – but in fact, she unbuckled it from around her waist and tossed it aside as she stood before him. He watched, almost forgetting about Caitlin’s slow, steady thrusts, as Gladys unbuttoned her jeans, pushed them down her legs, and stepped out of them. Her plain white cotton panties followed a moment later.

Her pubic hair was brown, a fair bit darker than the hair on her head, and it grew a lot thicker than Caitlin’s. Her smell was different, too, a bit stronger and sharper. He extended his tongue without being told as Gladys stepped up and took the familiar grip on his hair, and he drew it slowly up her labia in a way that he knew Caitlin, at least, really liked. But Gladys yanked his hair and ground herself forward into his face.

“Damn it, Ron, don’t fuck around down there. Find my clit and suck it.” Well, Caitlin had shown him how to do that, too. He worked his way quickly up to the top of her cleft, found the hard little nubbin, and wrapped his lips around it fervently. Gladys gave a gasp that was almost a shriek and pulled him in even deeper, smothering him in her wet, hairy folds. And damn it, Caitlin was pushing harder and faster into his ass, her motions becoming almost painful for the first time, and she was beginning to gasp and claw at his back and flanks. She had picked up Gladys’ trick of shoving in deep, using him to hold the dildo and stabilize it, and then rubbing hard against her end.

“Can I come, ma’am?” Caitlin moaned.

“Not yet, dearie. I – ohh – I want you to stay right where you are. Close to the edge.”


“Right where you are, or else. Reach around – around – and play with him if – ah – you want him to share your frustration.”

Caitlin did, with a vengeance. It was awkward for her to get her hand down between both their legs, but she took his scrotum in her hand and massaged it with her fingers as she fucked him. Ron moaned and gasped into Gladys’ cunt.

“Faster, damn it,” Gladys growled. “Suck and lick me like you mean it.” And he was all too happy to oblige, realizing – somewhat to his own surprise – that he genuinely wanted to please her. It wasn’t just a matter of trying to satisfy her enough to get her to stop, and make Caitlin pull out of his poor abused asshole. He worked her as deftly as he could with his lips and tongue, and was almost immediately rewarded with a scream of pleasure, a literal scream that echoed off the walls just like his cries of pain during that awful beating. Her two hands tightened in his hair hard enough to bring fresh tears to his eyes, but he accepted the pain and kept right on licking, trying to make it as good for her as he possibly good. She shrieked again and stood shuddering for a long moment before she stepped away, her naked body slick with sweat. Her pubic hair was full of his tears and her own juices.

“Two,” she panted. “Thank you, Ron. You obviously learned that at a good school.”

“Can I get off now?” Caitlin pleaded. Ron had never heard her say anything in such an abject tone. “Please, ma’am, it’s killing me.”

“I know you can take this, Cait. This isn’t the first time you’ve been right at the line and begging me to let you step across. But you’re really desperate? You feel like you can’t wait another five seconds?”

“No, ma’am!”

“Okay. If you want to get off tonight, here’s what you have to do.”

“Please, ma’am – I’m listening – ohh –“

“First, pull out. Right now.” Caitlin did, but with a sob. She was crying, Ron realized with excitement and alarm – desperate, in tears, just as if she had somehow become a slave again.

“There,” said Gladys soothingly. “You see, that wasn’t so hard. Now get rid of that cock.” Ron heard her unbuckle it and drop it to the floor.

“That’s good. I think I like you better as a girl, my slender beauty. Now, you really, desperately, want to come?”

“Yes, ma’am! Please, I told you!”

“Then come here, and climb up on this other bench. And get ready to earn what you’re asking for.”

For a minute she stood where she was, naked and trembling and in tears, an inch or two taller than Gladys but somehow looking much smaller. Ron literally held his breath as he watched her look from Gladys, to the bench, to him, to – amazingly enough – the stairs that would take her back to the safety of her own bedroom. But in the end, Caitlin simply bowed her head and walked over to the bench. Gladys watched silent and unmoving as she straddled it, got down on her belly, and extended her arms and legs to be restrained.

“I’m ready, ma’am,” Caitlin whimpered.

“Yes, you are. That was very brave of you. I haven’t softened up over the years, believe me – quite the opposite.” She walked over to Caitlin, not hurrying, and stroked her thighs and her buttocks and the small of her back. Caitlin sighed and shuddered, her eyes falling shut under Gladys’ touch. She gave a low moan as the other woman’s fingers moved between her legs and stroked the length of her labia.

“Oh, Mistress…”

Gladys laughed softly. “You are ready, aren’t you? Another caress or two – just a little faster – but not yet. First the hardship, then the reward.”

“Yes, Mistress. Please, I’m ready. For whatever you want to do to me.”

“Well, we’ll see. Hold still.” And she bent to fasten Caitlin’s wrists, and then her ankles, into the leather cuffs at the sides of the bench. Her touch, on another woman, was so different – just as firm, perhaps, but infinitely more gentle. And yet, when she was finished, Ron could see that the restraints were good and tight around his wife’s wrists. Caitlin’s eyes were still closed, her face tense and expectant. Ready for whatever Gladys wanted to do to her.

First she wanted to reposition her, apparently. Gladys took Caitlin’s bench and wheeled it over beside Ron’s, leaving the two of them parallel. Caitlin’s head was turned away from him, and she didn’t seem to have any intention of moving, but if he rested his face on his left cheek he could at least see the cascade of her hair, the lean curves of her flank, the side of one breast.

“I think,” said Gladys musingly, “that this is the first time I’ve had a married couple both tied up like this. For better or for worse, as they say – in good times and bad – in mastery, I guess, and in submission. I’m going to remind you what submission feels like, Caitlin my dear.”

“Yes, Mistress,” she sighed.

“And as for you, Ron,” – her voice was coming from the back of the room, as if she’d gone to get something – “don’t think for a second that this compromises her authority over you. The minute I let her up, she owns you again.”

“She owns me now, Mistress,” Ron managed to reply. “As far as I’m concerned.”

That made Caitlin turn to him, finally, and give him a rich, warm smile. Which became a grimace of pain as Gladys brought something – a multistranded flogger, from the sound – down hard on Caitlin’s ass.

“You can think of it that way if you want to, Ron,” said Gladys, giving Caitlin another casual stroke. “But even if she owns you, I’m the one you have to worry about right now. You didn’t think you were just going to get to lie there and watch me make her squeal, did you?”

Actually, he’d kind of assumed that would be the case, and he’d been looking forward to seeing how Caitlin would take it. But now he felt Gladys’ flogger prod the small of his back, getting her distance, and he only just had time to brace himself before the first blow landed. It wasn’t nearly as bad as the cane, or even the crop, but on tender, already welted skin it was enough to make him grit his teeth. And then, suddenly, Caitlin gave a harsh cry of pain, just as another stroke stung his own naked flesh. Gladys was thrashing both of them at once, a flogger in each strong hand. Her voice rose above the swishes and smacks, and the moans and gasps of her victims.

“That’s it. Sing for me, both of you. Cry for me.” And they did. Caitlin broke first, if only because she was taking her strokes from Gladys’ right arm. Ron wished he could hold her, or at least reach out and touch her, as she burst into tears and began to pull hard at the leather cuffs that tethered her to the bench, rocking and bucking with each relentless blow of the flogger.

“Please, Mistress!” Ron gasped, though he could feel the tears welling up in his own eyes as the heat in his thighs and his ass got worse and worse. “Stop hurting her – use them both on me –“

Gladys laughed. “So chivalrous. But hell, if that’s what you want…” And she obliged him. The flogger than had been torturing Caitlin’s ass moved up to his shoulders, and now she was standing beside his bench making him take all the pain she could dish out. Almost as soon as she found her new rhythm, Ron began to wish he’d just kept his stupid mouth shut. It really, really hurt, and he started to squirm and pull at his cuffs just like Caitlin had been doing a minute ago. And then there were the tears, trickling down his cheeks, soaking into the soft leather of the bench. But he could hardly tell Gladys he’d changed his mind, and anyway he supposed he was glad to spare Caitlin the pain. Glad to spare his Mistress – but it hurt so much! Gladys only laid on harder as his moans became hoarse cries, and then full throated shrieks. Somewhere, incredibly, he could hear Caitlin’s voice – “Mistress, stop, stop hurting him, it’s my turn!” – and then the pain suddenly stopped increasing. The scream he’d been getting ready escaped as a low, relieved groan.

But Caitlin was catching it. Oh, yes. Gladys was thrashing her just like she’d been thrashing Ron a minute ago, one flogger on Caitlin’s shoulders and the other on her upturned ass. She was sweating and gasping with the exertion of beating her helpless captive, her arms rising and falling like the arms of a diabolical marionette and her breasts bouncing just a little with each stroke. Caitlin pressed her forehead to the bench and sobbed and groaned beneath the hail of blows, not struggling now but somehow pulling into herself, bracing her body and trying to accept the agony that Gladys was giving her.

“Please, Mistress!” she cried, in almost the same tone she’d used to beg for an orgasm a few minutes ago.

“Please what?” asked Gladys casually. “Please leave you alone and go back to beating your slave boy?”

“Oh, no! But it hurts – I’d forgotten what it was like –“

“That’s why you need to be reminded.”

“Yes, Mistress,” Caitlin sobbed, but Gladys continued for only another few seconds before she lowered the floggers, breathing hard.

“There. You’re so beautiful when you cry.”

Caitlin smiled through her tears. “You’re beautiful when you’re making me cry, Mistress.”

“Well, I remember another way to make you cry, one I think you’ll like better. Are you ready?”

“Oh, yes, Mistress, if it pleases you!”

“It does. Here.” And she put her hand between Caitlin’s legs, cupping her vulva. Ron couldn’t see exactly what Gladys was doing back there with her fingers, but whatever it was it took only a second. Caitlin moaned and curled her body like she had under the flogger, and sure enough she burst into fresh tears as she took her reward from the hand of her Mistress. Gladys watched with a faint smile on her face as Caitlin writhed and bucked and ground herself into the bench, her eyes closed and her expression remote. Finally she quieted and lay still, sniffling and smiling. Gladys turned away and put the hand that had been between Caitlin’s legs under Ron’s nostrils.

“Smell that, slave boy. Whether you get any closer to it tonight is up to her.”

“You’re finished with us, then, Mistress?”

“Yeah, for all intents and purposes.” She began to unfasten his wrists and ankles. “You can clean our cocks, and pick up our clothes, but it’s almost time for Cait to take you upstairs.” He stretched his sore limbs and obeyed as Gladys knelt beside his wife, stroking her and whispering in her ear. Caitlin started to answer, and then they both turned to Ron, who had piled everything neatly and was awaiting further instructions.

“Slave,” Gladys said.

“Yes, Mistress?”

“Go upstairs and wait for your real Mistress in her bedroom. She’ll be up shortly. You can go to the bathroom on the way up, if you need to.”

“Wait on your knees, Ron,” called Caitlin languidly. “By the bed.”

“Yes, ma’am,” he gasped, and hurried off.

* * *

He wasn’t sure how long Caitlin kept him waiting. It had become difficult to keep track of time. What he knew was that he wasn’t the least bit sleepy, despite the stiffness of his muscles and the soreness of his welted body. Gladys had really put him through the wringer, and Caitlin too. He wasn’t quite sure how he felt about that. But his cock stiffened as he played through the memory of his wife moaning and squirming under Gladys’ floggers, and then again at the gentle touch of her hand. Gladys’ orgasms first, and then Caitlin’s, which seemed right and proper – but surely Caitlin wouldn’t leave him erect and desperate like this tonight? It sounded like it was going to be her decision, thank goodness.

Finally the door opened and she walked in, naked and flushed. Even with her cheeks stained with tears, and the welts on her ass red and angry as she turned to close the door behind her, the familiar air of command had returned to her carriage. She looked down at Ron silently for a minute, and then snapped her fingers.

“Get into bed. Stretch out on your back.” He obeyed instantly, and watched out of the corner of his eye as she hunted around in the top drawer of the bureau and came out with what she called his “sleeping cuffs” – comfortable, fleece-lined leather. He stretched his arms above his head and waited with barely disguised eagerness as she buckled the cuffs around his wrists and ankles and fastened them to the frame of the bed, pinning him down. She reclined on the bed beside him, but didn’t reach for him right away.

“So?” she asked. “How was it?”

He sighed and looked up at the ceiling. “She’s terrifying, ma’am. And magnificent. It’s a wonderful place to visit, but I wouldn’t want to live there.”

Caitlin laughed. “That’s about what I figured.” She took his penis in a casual, familiar grip. “You didn’t feel like we were pushing you too hard?”

“Once in a while, ma’am. There were plenty of times when I was scared, and hurting, and wanted to stop. But isn’t that part of being a slave?”

“Well, I never thought it had to be. But Gladys and I had a little talk down there, after she let me up.”

“About how to handle your abject slaves?”

“About how to handle you, mostly. About how you’d reacted to things.” She stroked her hand up and down his shaft, slowly, then was still again. He gave a shuddering gasp of pleasure. “I would have been afraid to take you that far on my own. You know how I play – I try to be careful with you, and I try not to let myself forget about your needs even for a second. But based on what she saw tonight, Gladys thinks you’re ready for something that’s much stricter and more serious. She thinks I could hurt you more, keep you on a tighter leash, and worry about what you need and want a whole lot less. She thinks, I guess, that you’re ready to graduate from slave-husband to just plain slave, except of course on paper. Is that true, Ron?”

“Oh, yes.” It wasn’t easy to talk – her fingers were moving again. “I’ve been trying to tell you for months, ma’am.”

“You could have just come out and said it. But that’s really, honestly, what you want? To give up even more control to me? It wouldn’t just be a matter of playing harder, when we play – we’re talking about major restrictions on your ESPN time, for one thing.”

“I want to be yours as completely as possible, ma’am. Really and honestly – especially after tonight. But how do you feel about all this?”

She laughed and moved her hand down to his balls. “After seeing what Gladys did to you – after helping her do it – I’m starting to realize that I haven’t been pushing you nearly as close to the limit as I thought I was. I could sink my claws in a whole lot deeper, and it would still be perfectly safe.” She suited action to word, until he gasped and squirmed at the pressure of her nails digging into the soft flesh of his scrotum. “If you’re really ready to give me even more power over you, I’m ready to accept it.”

“Deal, ma’am,” he gasped, as her hand settled into a regular, even rhythm on his cock.

“Okay, slave. But there are going to be quite a few changes, and some of them you aren’t going to like. I was serious about the ESPN thing. There’s every possibility I’ll get a mark of ownership tattooed right on your sorry little ass. And that place we visited tonight – we’ll be going back there lots, on our own and sometimes with Gladys. You can take it as a compliment that she’s interested in seeing you again. Maybe I’ll even whore you out to her for a week or two.”

“Sounds good, ma’am.” He pumped his hips, pressing himself into her hand, and then subsided. She gave him a faint, indulgent smile, and he glanced down at his cock. “And to seal our bargain…”

She laughed. “To seal our bargain, slave, I’m going to stop.” And, to his consternation, she did. She moved her hand away, quite suddenly, and left his penis sticking stiff and forlorn into air that suddenly seemed very cold and empty indeed. “I’m going to stop, and make you go to sleep just like you are. Fewer orgasms is going to be one of those changes you won’t like very much.”

“Please, ma’am! It’s been a long week – and a long night.”

“Ron, do you want a wife, or a mistress?”

“A mistress, ma’am. But even a mistress can be kind to her property!”

“Yes, she can. But she doesn’t have to be. Up to now, I’ve almost always been kind, when it was anything halfway important to you. Starting tonight, it’s going to be different. Kindness from me is something you won’t be able to take for granted anymore, if you really want to stick to our deal. So it’s your choice – I can get you off, and I’ll even use my mouth if you want, and I’ll uncuff you before we go to sleep so you aren’t uncomfortable, and in the morning things will be just like they were when we arrived here. Or I can leave you exactly where you are, aroused and frustrated and tied down – and in the morning, you’ll wake up in bed with your new mistress instead of your wife. It’s up to you.”

“Then leave me just like I am,” he said, without hesitation.

“Okay. But I don’t want to hear any more pleading or complaining about it. It wouldn’t be safe to make you sleep with a gag in your mouth, but I’m fully prepared to take you back downstairs and let you spend the night on one of those benches.”

“I’d much rather be in bed with you, ma’am,” he replied. “So no more complaining, I promise.”

“Good slave. And thank you, Ron, for the decision you made. I love you, and I want to own you. All of you.” She leaned over and kissed him, delicately and tenderly, pulling away when she was ready to pull away.

“I love you, ma’am,” he gasped. But she reached over, with a wry smile, and gave one of his nipples a hard twist that made him yelp in pain.

“Now that’s one thing I’ll always punish you for, from now on. Starting tonight, you’re going to call me Mistress.”

“Yes, Mistress,” he said happily, wondering how long it would take him to get to sleep with that unsatisfied erection nagging at his consciousness. It was the very best night of his life.

Copyright ©MVI 2006


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