Molly's Date Night

His eyes snap wide open. I start tapping my foot. His cock stiffens up, what little softness he'd managed to get in it, gone. I give it four taps of my foot. He already got one before that last swat. But that swat wasn't for the stiffness.

I swat his cock again. He yelps. I start tapping.

It takes eleven swats of the ruler for Ken's cock to reluctantly soften up about halfway. It's enough to leave his eyes wet. It's enough that his squeals have gotten rather girly. It's enough that his cock has shrunk to under the four-inch mark.

"That's better." I grin. "Now make sure it behaves from now on. When I want it hard, I will tell you. Otherwise... don't be thinking about girls you have no chance of ever seeing, much less touching. Now sit."

The instant his bottom hits the chair, the same chair Renee used, I'm scolding him to sit properly. To sit up straight. To spread his knees and feet wide. To keep his hands behind his back. And his eyes on me, which is likely the last place he wants them. It's hard not to think about a pretty blond when you're staring at her. And that's what I want. I want it to be hard for him to "behave."

I start with the mundane questions. I learn little. I learn that Ken is 48. I learn that Renee is his fifth lover. I already know that he is only Renee's third lover. And that Molly is the only child they've had. I just assume that Ken looked far better in his youth, to land a pretty woman such as Renee.

Then I start with the more embarrassing questions. He confesses to masturbating about twice a week, which is also about twice as often as Renee does. He tells me he usually does it in the bathroom, alone, sitting on the toilet. How... not exciting.

I don't let it rest. I ask him when Renee doesn't take care of his needs for him. He tells me the same story as she did. They both have busy lives, and more often than not one of them is more interested in sleep than sex. In my mind, that's the same as saying that the sex between them has grown boring. And that explains something else to me: why both have been so eager to play. Both obviously have that submissive streak in them, but it's more than that.

Now I want Ken to misbehave. So I ask him so questions that will make him think about Renee's attractive body. "How tight is Renee's pussy on that needle dick?" is the first one. "Does it get wet for that little thing?" I know that Ken has never gotten to try anal sex, and wants to, so I ask him what he thinks Renee's bottom would feel like. He tries to say he doesn't know. I push, reminding him that I asked what he imagined. He starts telling me that he thinks it will be tight on his cock.

That's the question that makes his cock start stiffening backup. I don't let it get hard. Instead, I flick my wrist, sending the tip of my crop soaring through the air as it arcs downward toward his shaft. It moves so fast Ken doesn't even see it coming. The leather tip of it snaps lightly down on the bulbous soft head of his cock, shoving it down against the seat as it cracks.

Ken screeches a very girly, and pained, yelp. His eyes pop wide as he looks back at me with nervous eyes.

"Bad Boy!" I snap sternly, my voice matronly, like maybe a strict librarian would use. "Mind that horny little dick!" I start tapping my foot again.

Ken might listen to me. But his cock doesn't. The firm stroke on its tip only made it stiffen up fully. As Ken obediently sits with his thighs parted, it leaves his balls resting on the seat, fully exposed now that his cock is standing out again. With every tap of my foot, Ken looks even more nervous. Clearly, he knows what's coming after the fifth tap.

But that doesn't stop him from getting another stroke on the head of that cock. He yelps louder this time. Now that his cock is back to full rock hardness, I'll bet it hurt slightly more this time. I start tapping my foot again, noticing that the head of his cock is already more a shade of red than of its normal pink.

It takes three more strokes of the crop before his cock starts to soften up again. Ken sits there through all of his strokes, leaving his cock bared for my cane. Tell me that's not subservient!

I wait until Ken's cock is fully soft. Now it's under three inches long, and no more than half an inch across. Well, maybe a hair more. As it hangs limp, it doesn't even reach the bottom of his balls. So under-equipped. I can't help but wonder if Renee regrets the size of his cock, and if she misses the feel of a real one. A big one that will tightly stuff her pussy and feel so good.

I tell Ken to stand up so that I can "inspect what little cock he has."

Ken quickly stands up, keeping his hands behind him. His cock twitches just the slightest bit as he rises. But mostly it hangs limp in front of his balls. His eyes look down, watching me. I don't bother to get up from my seat. It puts his cock at eye level for me.

I take his soft cock in my hand. Instantly I can feel the blood start to flow. The cock starting to stiffen. "Behave!" I warn him firmly. It doesn't seem to do much good. I can tell that Ken is struggling to keep himself from getting aroused, but with my hand, even gloved, touching his cock, he's quickly losing the battle. His cock seems to have a mind of its own.

While it's still soft, and smaller, I wrap my hand around it and squeeze it tightly. Now I can really feel the blood straining to swell that cock up to its full eagerness. And I can feel my muscles working hard to keep it squished snugly.

I release my squeeze, again letting the shaft lie atop my flat palm. It immediately starts growing and stiffening. Sophie hands me the ruler. Ken winces hard, knowing what I'm going to do with it. Then he winces even harder and yelps lightly as it cracks down atop the length of his mostly hard shaft. I start tapping my foot again. It takes Ken four taps, and four swats, before his cock, now throbbing with both its ache and the pain, starts to soften back up. One more swat and it's back to its almost fully limp state.

I leave it where it is. I set the ruler across my thighs, where it won't be far from my reach should I need it again. With my other hand, I cradle his balls.

His balls are pretty big. They're hanging loose in their sack, giving me plenty of room to gently push them around. I know he feels them moving. I want him to. I want him to feel me "examining" his balls.

Ken doesn't seem to mind. Then again, I'm being tender with those sensitive eggs, so I'd bet he likes it. I can hear a light groan in his breathing, but it's not from me playing with his balls. It's from trying hard to keep that cock soft while I do. I don't think that cock minds the spankings it has been getting nearly as much as Ken does.

I spend at least half of a minute teasing his balls. He manages to behave, but it's obvious that it's a struggle for him. With them still cupped in my hand, I pronounce his balls to be swollen up. I add that's a sure sign of "long-term neglect" which I take to mean that he's not been fully satisfying himself with his hand. And maybe not with Renee's skanky pussy, I add.

I'm still holding his balls and his cock. "Now, let's see how neglected that prostate is. Bend over the table," I say in my all-business voice. I only tell him what's next because I know what sissies boys are about their butts. Isn't that so ironic? It seems like they all want to put their cocks in my butt, but whine if I want to put a little finger in theirs!

Ken does not look thrilled with the idea. He moves slowly and reluctantly as he turns to face the table and lean over it. I have to instruct him to step back from it, putting his elbows on its edge and getting his back flat with the floor.

His cheeks are covered with the same sparse fur that covers the rest of him. They're moderately loose, but not flabby. They do meet fully, the soft globes flush against each other to completely close his crack. I just use the finger of one hand to push those spongy cheeks apart.

It bares his dark purple-brown, dime-sized asshole. His crack has its own coat of the light fur, which leaves a few hairs surrounding the ring of muscle. But not on it. Not where the countless, and slightly prominent wrinkles flow into a tightly cinched pencil-point of darkness. I've never been a fan of hairy assholes. This guy is so going to be shaving his crack if I allow him to hang around my toybox.

I squeeze another tiny dollop of lubricating gel atop my finger and lie my fingertip against Ken's asshole. Instantly I feel the muscle clench even tighter. As if that's going to stop anything! Not! "You will stay still and quiet," I tell him, still using that all-business voice.

Then I press lightly. Immediately I feel my finger starting to push into the funneling of his ring. I can feel the tension in his resistant muscles as well. It doesn't stop me. My finger slowly inches forward. As it does I can feel his ring yielding just enough to allow my finger to slip into its thickness. It squeezes snugly around my finger. My finger glides over the greased, wrinkly flesh as it keeps inching further into his depths.

Ken grunts hard as my finger stretches his muscle the little bit it takes to allow me through. He stands there, his legs and back tensed, and grunts soft, panting, breaths as I continue slipping deeper into his bottom.

He's still panting those grunts when I run out of finger to push into him, the webbing of my fingers flush against the outside of his asshole. I can feel his asshole clenched tightly around the base of my finger. I can feel the paper-thin wall of smooth muscle around his rectum lightly squeezing against my finger, too, as if trying to push me back out of his bottom.

In order to feel his prostate, I have to curl my finger into a U-shape. Ken feels that. He grunts hard as he feels my finger pulling up tight. I put a couple of fingers against the narrow strip of flesh between his dangling balls and his asshole. Then I lightly massage my finger against his insides. It doesn't take any time for me to feel the hard gland that's his prostate.

I focus my caresses on his gland. There's nothing between my finger and it except for the thin membrane of his rectum, and that does little to dull the sensations. It takes about five or ten seconds for Ken's stressed grunts to start turning into sweetening purrs. That's the same point when I see his little cock quickly explode to its full hardness as it hangs down between his thighs. As I pressed into his bottom, I couldn't even see his cock behind his sack. But now I can see the head of it twitching below that sack. And I have no doubt the shaft is at its full hardness.

"Oh, you shameless horny little boy!" I scold Ken. "That little cock can't even behave long enough for me to poke around up your butt! I swear, that cock likes it up your butt!" I go one stroking the tip of my finger over the swollen gland of his prostate for a few more seconds. As I do I feel his asshole squeezing even tighter around my finger.

"Now I'm going to have to spank you! That cock is just going to have to learn to mind its owner. Me!" I straighten my finger out, earning me another strained grunt from Ken. I very slowly inch it out of his bottom, giving him a minute to feel that and think about being spanked.

I pull my gloves off and have Sophie hand me the hairbrush. I summon Ken, telling him to come over to me and get his spanking. I have him kneel down at my right side. "Over you go, bad boy," I command him, pointing for him to lie himself over my thighs. Ken moves hesitantly as he stretches his chest over my legs. As he does, I use the back of my hand to just knock his cock up. Then, as he lies, it traps his stiff cock between his pubes and my thigh.

"You get six swats. Three on each cheek. You will be a big boy for your spanking. Lie still. No talking. And definitely, no trying to protect that flabby bottom. Just lie there and accept the spanking you deserve. Maybe next time you won't be so shamelessly horny!"

I swat his cheek. I give him a fairly hard stroke, not my hardest, but a good one that leaves a medium pink brush-print on his hairy cheek. He grunts, hard, and stiffens up. I guess he wasn't expecting a real spanking, just a little playful one. That wouldn't be a punishment!

I swat his other cheek, getting just as pained of a grunt from Ken.

I land the second round of swats about half atop the already stinging pinkened flesh, and half atop the neighboring virgin flesh. Those strokes get me nice "OW!s" from Ken. They get his hips squirming around a little on my lap, too. I can feel them. And I can feel how they're rubbing the cock trapped between us. Now there no chance it won't be stiff after his spanking!

The third set of swats gets me louder, and slightly girlier, "OW!s" from Ken. They get him squirming pretty good, too.

As I could feel it would be, his cock is fully hard when I put him off my knees. His face is a little red, too, and it's not a blushing red. I'm paying more attention to that very stiff cock sticking straight out.

I scold him for the hard cock, scornfully adding that his spanking was punishment, and how shameless of him it was to try humping my leg while I spanked him. I start tapping my foot as Sophie fetches my crop for me.

I don't wait for the full five taps. As soon as Sophie hands me the crop I stroke the leather tip of it along the length of the cock, caressing it softly. I keep tapping my foot. "That cock just can't seem to behave, can it? How are you ever going to stand in the corner like the naughty boy you've been? Hard cocks aren't allowed in the corner!"

As my foot makes its fifth tap, I give the head of his cock a good swat with the crop. It's light, I'd never put too hard of a stroke there, but it's enough to leave a crop print that covers one full side of the soft head. It's enough to get a loud, girly, squeal from Ken and moisten his eyes. Unfortunately for Ken, it also gets a pair of crisp twitches, the excited kind, from that cock.

It takes six of those firm swats for the cock to go fully limp. But then, there's no denying that the head of it has to be stinging like he'd stuck it in a hive of angry killer bees. The tears coming from his eyes tell me that. As did the loud, very girly, shrieks he made with each swat.

Once his cock is completely limp, I have Ken stand up. Then I have Sophie fetch me a heavy, wide zip tie. Ken watches me with very nervous eyes, not understanding what I'm doing to him. At least not at first. I take hold of his limp cock and bend it up in a U, lying it against itself. Then I wrap the zip tie around it, just beneath the head, and cinch it down fairly tightly. Tight enough to ensure his cock stays fully bent in that U. And that will ensure that it can not get stiff. It might try to, but all that's going to happen is that it will strain against itself, rather unpleasantly for Ken, until it gives up.

I leave his cock bound up and walk him to a corner at the opposite side of the house from where Renee is still standing in her corner. I tell him that he has 47 minutes to serve there, and remind him of the rules as well. Then I leave him there. I have time for a quick cup of coffee before Renee's time is up.

Chapter 04: His Choice

When Kent returns Molly from their date I'm ready for them. It's all of five minutes before the 10:00 pm curfew I set for Molly. That alone tells me that Kent had a decent time with the girl. It's simple "date math." The more fun a boy has with the girl, the closer to curfew he brings her home. The five minutes is negligible. That's just Kent ensuring that Molly does get in trouble for being late. Clocks can be a few minutes off. And if she's late, she might not be allowed to date him again.

As I asked him to, he has Molly leashed when he brings her through the door. I'm sure the leash came off the instant he got her in his car and didn't go back on until he was parked in the driveway again. He's not the type to have his date on a leash. But I hope the snug collar around Molly's neck served as a constant reminder to her that she is now my property.

As he leads her through the door, Molly walks demurely behind him. As she should. She holds her head up, apparently not ashamed for us to see her leashed. She wears a big smile on her face, too. That tells me that she had fun with Kent. I hope she had a lot more fun with him than she was planning to have with "Nate the loser." I wanted her to. Slave lesson number one: her life will be much better if she selflessly devotes herself to my pleasure.

I meet them just inside the front door. I ignore Molly, instead of asking Kent "was this baby bitch a good bitch for you?" I want Molly to get the impression that I don't care if she enjoyed herself. I only care if she pleased Kent, as I told her to do. I want Molly to stop thinking of herself as a girl and start thinking of herself as my property. As a thing, not a person, that I will use as I wish without regard for it.

"Yeah, she was awesome," Kent tells me. The grin at the corners of his mouth tells me he means it. So does the little sparkle in his eyes. The eyes that are still shooting little glances at Molly's so ample chest. I'll bet he's wondering what she'll look like naked. The fairly skimpy dress I put her in shows a lot of her body. Enough for him to see that she has a pretty good figure. Even if he can't see every last curve of it.

I ask Kent what he did "with my bitch" on their date. He tells me they went to a place near campus, a place I know well, for burgers and some dancing. They ran into a couple of people Kent knew there, and he introduced Molly to them as a girl I'd loaned him for the evening. I'm not miss famous or anything, but I do have enough of a reputation around campus that I'd bet most students there have heard something of it. Most, or all, of which was made up. But enough for them to guess what Molly is. I'm sure Molly enjoyed meeting Kent's college friends. College friends are a big thing for high school girls.

Molly stands quietly smiling from ear to ear as Kent recounts the highlights of the date. Obviously, she had fun. More obviously, she's hoping Kent will want to ask her out again. And even more obviously, she has forgotten that Kent won't ask her. If he wants to see her again, he'll ask me. I'll decide if she goes or not. Not her. And now that I know she wants to go, she'd better be a very good peasant bitch if she wants any hope of being sent with Kent again.

I don't ask Molly if she had fun. I can see that she did. Instead, I try to give her the impression that I don't care if she had fun. Only that Kent did. "Molly, be a good bitch. Give him a nice think you hug and kiss. A very nice one."

Molly's smile grows. Enough that I'm pretty sure this is going to be their first kiss. Why am I not surprised that Kent helped himself to a few before bringing her back? Oh, yeah, he's male.

Molly puts her lips to Kent's. She wraps her arms around him. She kisses him passionately. It's a long kiss. A kiss that Kent returns just as eagerly as she gives. A kiss they spend hugged together snugly, Molly's breasts pressed firmly against his chest.

Before Molly breaks the kiss, I put a hand on Kent's wrist. I nudge his hand to glide down over the curvy cheek of Molly's behind. When his hand is on the bare flesh of her thigh, I nudge it back up, this time pushing it under the hem of Molly's dress. I don't need to nudge it up. It goes right up to where I wanted it to. Molly's bottom. And it explores that cheek rather enthusiastically. It gets Molly kissing him even more eagerly.

I allow them to kiss for a couple of minutes, Kent clearly enjoying the kiss as much as he's enjoying the feeling of Molly's panty-clad bottom. Or maybe her partially bare bottom. The way his hand is moving under the bottom of her dress tells me that he's trying to slip a few fingers under her panties. And Molly isn't objecting. It saves me spanking her for it. She doesn't get to object to anything. Only I do, and I don't mind if Kent plays with her bottom.