Date Night

"Oh, Ow! Ow!... Please, Miss Rodgers!" Claire pleads, her voice both pained, and sultry deep. "Please, don't whip me there, Miss Rodgers, it hurts too much! Please, Ma'am, please!"

"EE-OWW!" Claire shrieks out as the crop taps so lightly atop her pussy mound again.

"I didn't say you could speak, slut hole! I said behave. Now behave, slut hole, while I see just how trashy of a gutter whore your slut hole is." I think Claire just earned her new name. Slut hole. I hope she likes it. I'll tell Colette later. I know she'll like it!

Claire falls limp, sobbing very lightly, and mostly nervously, not from the pain. Her pussy weeps a little more honey into her slit, covering the tips of her folds and starting to cling nicely to her lips.

I put the feather back, hearing Claire whine a faint "oh, nooooo..." under her breath. As if she knows she's going to be a bad girl.

She's a very bad girl. I barely get the feather moving before her hips are snapping up and thrashing hard. Or before I hear the creaking of the bedposts as her arms and legs thrash against the taut ropes. Or before I hear her scream out another "OOH-EE!" It seems like her voice grows both throatier and squeakier with each cry.

I'm sure Claire knows what's coming. After all, fair is fair, isn't it? I snap the crop. And it leaves a light pink welt atop her tender pussy lips.

Claire screams, loudly. She screeches, her body shuddering and thrashing wildly. Her honey weeps again too. Actually, it more flows this time. At least half of her lips are covered by the time I think about putting the feather back down.

By then Claire is sobbing hard, but still nervously, not from the pain. It doesn't hurt that badly yet. I'm not even trying to hurt her. I can just see the effect the strokes are having on her, so I'm more teasing her with them than punishing her. I'm sure she's nervous that one of them is going to really hurt. It won't. I don't know if she'll like that or not. Colette can figure that out later.

I start teasing her slit again. Claire doesn't even last as long as she did last time. She jumps the instant the feather touches her, shrieking loudly, and very urgently. And thrashing those hips around.

I snap the crop, this time searing an angry, medium bright, crop print onto her milky white lips. It's just enough of a stroke to make those lips glow bright and hot pink. And it's enough for Claire to cry out a loud, and panicked, "OW!... Oh, OWWW!!"

Claire's body starts trembling hard. Almost vibrating it trembles so crisply and fast. That has her nipples dancing atop her mounds. And it has her pussy weeping a river of honey. More so, it has the edges of her folds quivering even with the edges of her lips holding them.

Claire pants very nervous, sobbing "Ooh, OW!s" as she lies there, listening to me scold her pussy for acting like "the filthiest gutter whore," and just waiting for the last stroke she knows is coming.

That stroke almost sends her over the edge. Over the edge into an orgasm. I can see it. One more would finish her off. It's the way her body quivers so energetically. It's the strain in her sultry, throaty, and squeaky, voice. The deep, fast pants of her breath. The way her nipples strain to stiffen even more. It's everything. The flowing honey from her slit.

"Obviously this slut hole is far too slutty!" I loudly announce to everyone. Then I turn to Jerry. "I don't know what you've been doing with this slut hole, but it's very clear to me that you haven't come close to actually satisfying it. Surely you can see how horny that slut hole is! There's no way that it's had a satisfying orgasm in a decade!

"And you try to call yourself a man?" I grab hold of the straw of the cock stopper, pinching it just above the flag. That way, my fingers aren't touching his cock. His very stiff cock. A cock that I know is weeping its own cum, only that cum is welling up behind the cork, unable to weep out of his cock.

I give the straw a sharp little wiggle. His cock wiggles with the straw. I'm sure I have his attention now. "You clearly have no idea what to do with a woman! You can't even take care of a piece of filthy gutter skank like this slut hole! I'll bet you've never even seen an actual woman naked before, let alone been allowed to touch one! But even the dirty little whores you have seen should have taught you to take care of something this disgusting and slutty."

I sigh again. "Time to learn. Go ask this bitch's husband to show you how to fuck a slut hole. Go on, he can fuck his wife and you can watch."

Jerry stands there, frozen. As if this is something he never imagined. His eyes dart everywhere, more nervous than I've ever seen them. The look to the stern, icy look on my face. They look to the eager look on Kevin's face. They look at the panicked, nervous look on Claire's face. And they keep darting back and forth across all of our faces. As if Jerry is trying to decide what to do. Or more likely, trying to decide what Claire wants him to do. Or rather how Claire would handle either of the choices. Option one being Jerry asks Kevin to fuck her. Option two being they're both punished. I doubt he's considering that option two means that after their punishment, he'll just have to ask Kevin anyway. He looks like he's more worried that Claire will freak out. That Claire might leave him or something. That nervous look on her face hides her true face now. It lets him have no clue whether she's nervous that he will allow Kevin to fuck her, or nervous about something else. Like that she will act like a complete whore if Kevin touches her.

I give Jerry about half of a second to hesitate. Then it's time for me to teach him that I don't tolerate hesitation. Only obedience. I know there's no way Colette would let him hesitate. He knows that, too. Besides, how is Claire going to learn to trust her Mistress and turn her body over to me without reservation, if Jerry, the experienced sub in the couple, hesitates to obey?

Jerry deserves a harsh reminder of his place. I have no problem giving him one. I snap my fingers for Sophie. I yank hard on Jerry's leash, snapping his head down, and starting him bending over. I use my other hand to push down sharply on the back of his shoulder blades, bending him over. His reflexes kick in, bringing his hands around front to block his fall. If he were actually falling. "slave, number 8," I tell Sophie.

I keep pulling Jerry's head down by the leash. He grabs the chair, quickly lying his forearms on its seat to stop himself. Reflexes save me so much work! You just have to know what someone is going to do and use that against them. Like they teach in Judo! Jerry's head comes back, bringing his eyes up from the seat. Now he's looking forward. It has his eyes at about the level of Kevin's crotch. And about six feet from it, staring in that direction. Not staring at Claire.

Claire just lies there, quivering and purring slowly-fading little "Umm!s" as she ebbs back from the edge of climax. She's not paying much attention to Jerry.

Sophie puts the number 8 in my hand. It's a dildo, shaped to look like a giant black penis. It's eight inches long, hence its name. Its' also 1½" inches across, and slightly wider than that at the bottom of its stiff head. This one is solid plastic with a rubbery layer of latex over it for feel. And Sophie has already put a tiny drop of lubricant on the very tip of it for me. She knows what I'm going to do with it.

"What are you, fuck stick, shy about a fucking?" I start moving the dildo towards Jerry's bottom. Quickly the slickened tip of it is pushing between his cheeks. "All pussies love a good cock rammed into them... see, pussy?"

I can already feel the firm resistance of the fat head of the dildo as it presses firmly against Jerry's asshole. And just as firmly against everything around his asshole, even the valley of his crack. That cock head is far wider than his tightly clenched asshole.

I push harder.

"OW!" Jerry screeches. His voice is loud and panicked. Strained as well. The dildo forces his asshole to stretch wide, and it does it suddenly, straining his muscle. His muscle feels like a toe hit with a hammer, throbbing with a nearly unbearable ache. He flinches, his hips trying to shoot forward away from the cock. My hold on the leash keeps him from doing anything more than arching his back up, and that only lets him move an inch or so.

The dildo presses forward, gliding over the now-taut flesh atop his ring. It slips deeper and deeper into his bottom, stretching his asshole wide. And stretching his insides out taut as well. It fills him almost to the limit. It stuffs his bottom full. And I am not trying to be gentle. I'm teaching him a lesson. I keep pushing hard and fast, driving the dildo uncomfortably into Jerry's bottom.

I push about seven inches into his bottom. Jerry screeches the entire second or so it takes. Good. It leaves about an inch of the dildo sticking out beyond his cheeks.

I use his leash again to jerk him hard, standing him back up. That has the dildo shifting around inside his body as the angles change with the motion. And that gets another strained grunt from him.

I grab his balls, squeezing them just firmly enough to make sure he feels it and I have his full attention. "See, pussy, pussies like cocks in them. Now be a good fuck stick and go ask this man to fuck his wife and show your worthless butt what to do with a cheap slut hole. Now, fuck stick."

"Yes, Miss Rodgers..." Jerry says. I've noticed something about Jerry. He addresses me as "Ma'am" when he's excited and as "Miss Rodgers" when he is completely humiliated into a heightened arousal. The "Miss Rodgers" always comes in a very humbled and sheepish reluctant voice. I love that cowed tone.

Jerry steps over to Kevin, only now he's walking slowly, taking short little steps. I should spank him for it! But it's just so adorable to watch the wide black base of the shaft wiggling at me as it sticks out of his firm globes that I let him get away with it.

"Excuse me... Sir... would you mind... please... will you please fuck your new wife so that I can see how a real man pleases a... dirty slut hole, Sir?" Jerry asks in the most humiliated voice I've heard from him yet.

"Sure, dude, why not?" Kevin answers a wide grin on his face that tells me he's been eager to fuck Claire. "I'll show you what to do with that wet little thing." Kevin grins.

Kevin drops his pants quickly. Kevin's cock, long since stiff and ready, jumps out. It stands out straight for Jerry to see. It's the second reason I picked Kevin for this assignment. His cock. It seems to dwarf Jerry's. It's close to two inches longer, making it just short of seven inches. And it's at least ⅓ thicker than Jerry's. Slightly over an inch and a half thick. It has a light pink head that's spongy and soft. And it's circumcised so every bit of that head is on display. His shaft is lined with some thick, dark veins for texture, and those are visible through his skin.

Jerry stares at Kevin's cock. At first, his glance is envious, as if he wishes he had a cock that big. Then a nervousness creeps onto his face as he thinks about that fat, long cock pushing into Claire's pussy. I'm sure he remembers the fat, long shaft pushing into his bottom a moment ago. HE has got to still be feeling the burn in his asshole from that.

Kevin pulls his shirt off, letting Jerry see the toned and defined muscles on his chest. A build better, and harder, than Jerry's older body can manage. Kevin steps out of his pants, kicking his shoes off and aside as he does. Then Kevin start crawling into the bed over Claire.

I still have hold of Jerry's leash. I use it, a sharp jerk on it, to pull Jerry back over to the chair. I grab his shoulders and push him down as I order him to sit and watch. Jerry sits and then freezes with his bottom just above the seat of the chair. Right at the point where the end of the dildo touches the chair. That's the point where Jerry realizes that sitting down is going to have his body weight pushing his body down onto the dildo. Driving the dildo deeper into his bottom.

I snap his leash hard. Jerry grits his teeth and lowers his bottom with a strained grunt that he can't manage to mute. I immediately scold him for sitting improperly. Since he's being such a pussy, he should be sitting like a little girl. I make him cross his legs fully. And put his hands behind his back, leaving all of his weight on his bottom. And the dildo. Then I make him stare at Claire and watch everything closely.

I watch Jerry mostly to make sure he doesn't avert, or worse close, his eyes. He's to watch Claire fucked by Kevin.

Chapter Five - The Proper Use Of A Slut Hole

Jerry sits in his chair. Even with his legs crossed like a lady, his cock is standing up straight and eagerly stiff. It's now rising on an angle from his pubes, waving its little pink flag high. Jerry tries to sit still, but I can see him fidgeting slightly. It's kind of hard to miss. Every time he shifts, even the slightest bit, his bottom moves against the thick dildo in his bottom. That makes him grunt hard. It makes him sit still, too.

But every time I see him fidget and still, I also see a light twitch run through his cock. That's enough for me to know that he is liking this. And I know that his cock is weeping tiny droplets of cum. Those are just welling up behind the cork, unable to flow to the tip of his cock and out.

Kevin is definitely enjoying his new wife. Before he came over tonight, I gave him instructions. I wanted him to know what to do, if and when I allowed him the chance. I didn't know if I would be able to offer him the chance. I couldn't know how far Claire was willing to go. I was rather pleasantly surprised to discover that in spite of everything she's said, Claire was willing to join in the fun. It just took a little prodding to get her over that shyness.

I didn't want to have to be giving Kevin step-by-step instructions. I'd expected, or thought, that Claire would go along with the date part of the evening. I was less sure if she'd go along with having sex with another man. Especially with an audience. I'd planned on her being the vanilla wife who liked to watch her husband degraded, as Colette told me she seemed to be. I didn't think that vanilla wife would appreciate her lover being told exactly what to do with her. I figured she'd prefer to think that Kevin wanted her body. It wasn't until I was standing there with my finger in her bottom that I knew the truth.

Kevin is following his instructions diligently. I'd told him not to just fuck her. I told him to start with some good foreplay. I thought it might help a vanilla wife relax and melt into the new sex. Now I know that's not going to happen. Claire is far too antsy and aroused. It's just another torturous tease for her. And that's even better in my opinion!

Kevin started by kissing his way up Claire's stomach and chest. All the way to her lips where he kissed her for close to a minute. It took about half of a second for Claire to melt into the kiss and kiss him back with every bit of the hunger burning in her pussy. Claire kissed him very eagerly. Very passionately. It was the kind of kiss where her tongue had to be exploring every last bit of his mouth. It was the kind of kiss that says "fuck me now."

It was the kind of kiss that I'd bet Jerry almost never gets from Claire. And hasn't gotten in a while now. It was a hungry kiss, one full of desire and loaded with unfamiliarity. As if Claire was soaking up the newness of this "new husband." As if Claire was starving hungry to explore more of him.

Then Kevin moves his mouth down, slowly kissing his way to Claire's full breasts. Like any man, he licks his way straight to her nipples. He puts his tongue to a nipple, slowly drawing it around the side of her tall nub.

Claire lies there. It's the only thing she can do. The ropes won't let her move. And it's not for lack of trying. Since Kevin's lips first touched her body, Claire's hands have fought the ropes hard, trying to get to Kevin. Not to push him away. To hold him tight. To explore his body instead of lying bound while he helps himself to explore hers and she gets only the tiny bits of his that he gives her. Claire's body quivers constantly. But with every touch from Kevin, it shivers hard, as if hit by an electric current. Claire purrs softly, deep, throaty, and very hungry little "Um!s."

There's nothing still about Claire's body. Every bit of her squirms eagerly. She's not fighting to get out of the ropes now, she's fighting to get to Kevin. As if all her body wants to do is devour this man.

Kevin tries hard to ignore Claire, but I doubt any man could totally ignore a woman while making love to her body. Especially when the woman is as eager for him as he is for her. There's no mistaking how eager Claire is. We all saw that with the feather.

Usually, I'm not this nice to a toy. I usually just have them used shamelessly as the sex toys they are. But this is working out well. It might be incredible for Claire. It might be exactly what she likes and wants. But it's also killing her. She can't stand to wait. She's already insane, and her over-eager lust is showing. It's about as obvious as an alligator in a swimming pool. (I stole that line from Sophie, my Florida girl!) If Claire could move, or even get just one hand free, she'd jump on Kevin and take him. But she can't. She's learning what it's like to be helpless, to be fully under someone else's power. To be at the mercy of her lover. To only be able to lie there and pray that she'll get the sex she's throbbing and aching for.

I love seeing Claire squirming so energetically. I love seeing her so needy. But the best part of it is watching Jerry. With me standing over him, crop in hand, he has no choice but to sit there and watch every bit of it. To watch his wife so eagerly dying for another man's touch. To see the hunger running through her body for it. I'm sure he's remembering long ago when he was new to Claire and she openly lusted for him the same way. Long ago. Now he can only watch her show far more passion for Kevin than he's used to seeing for himself.

It's clearly killing Jerry. I can see it on his face. He's hating it. He's absolutely humiliated to see Kevin driving his wife to heights of arousal that he doesn't. He hates seeing the hunger on Claire. But his cock is loving it. It's twitching so hard that it's almost jumping around. And I know it's worse for Jerry to have to sit still. I'll bet, if he could, he'd be touching his cock right now and not even knowing that he was doing it. That cock has to be aching almost as badly as Claire's pussy is.

Claire's pussy is on fire. Or hotter than that. By now her honey has covered every bit of her mound, especially the outside of her lips. I watch as Kevin just shifts his body around, working the tip of his cock over to Claire's waiting mound. He keeps his strong, toned body snuggled lightly against Claire's softer body, Claire's hard, long nipples pressing against his firm chest.

"IT'S TOO BIG!" Claire blurts out. I can hear a slight nervousness in her voice. Slight. Mostly her voice is throaty deep and very breathy. Very sultry. Very hungry. The soft head of Kevin's cock easily slips into her slit, her slippery, hot honey greasing the way for it. His stiff shaft starts to follow. Claire's lips and folds guide the spongy head right to the narrow entrance of her tunnel. And then it starts slipping into her body.

Kevin's cock must be thicker than anything Claire's had before. Her eyes go wide for a second, telling me that she can feel the firm muscles of her pussy being stretched taut around the thickness. "OOH!" Claire purrs out as the wide shaft begins slipping into her eager tunnel, teasing the countless nerves lining her soft walls. "OH, YES, SO BIG! OOH!"