Date Night

The paddle lands with a loud splitting crack. As the crack rings out, I catch sight of Claire flinching from the sound. "OW!" Jerry screeches, and this time his screech is louder than when I put the spreader in his cock. "oh, EE-OW!" his voice is high and girly.

Jerry's bottom isn't still. Too bad that his cheeks are firm enough not to jiggle. The way his hips are squirming, trying to wiggle some of the sharp sting out of them, those cheeks would be dancing!

The way he's laying has his stiff cock trapped between his pubes and the top of my thigh. With his weight on his steely shaft. His squirming hips grind against the top of his hardness, and that has his cock grinding against my thigh. The stick in his cock does nothing to discourage him.

"You pervert!" I scold Jerry. "What are you a dog? Stop humping my leg like some horny little poodle!... In fact, that's so disgusting, that stroke won't count! Now behave. I know you're already crying like a girl, but try to at least pretend to be a little boy, not a complete dog!"

Before Jerry can say anything, I snap the paddle down again, lading it right atop the already pink and stinging flesh of his globes.

"YE-OW!" Jerry shrieks, his voice as high as any girl's. He tenses up hard. "uh, mm... OW! OW!" Jerry almost starts sobbing already. What a wimp! This is going to be so fun! His knees knock against the chair as he stiffens up. His bottom jumps up a little, easing the pressure against his cock. He slowly relaxes and lies himself back over my knees.

"One, Miss Rodgers. I'm sorry for cumming without your permission, Ma'am. I deserve four more strokes, Ma'am. May I please have another spanking now, Miss Rodgers?" Jerry obediently counts his stroke off. It's the exact wording Colette would demand he uses. She's a little stricter about the wording than I am. It's fine by me.

I give Jerry what he asks for. A third stroke that counts only as a second. And I land it almost atop the bright pink flesh of his cheeks. He has enough cheek for me to mix the strokes up a little. I'm just not in a kind mood. Not after his sin! That was too naughty! Even if I did make it up. He believes it!

The next stroke, the third by the count, leaves Jerry sobbing.

The fourth stroke is the one that gets Jerry crying hard. And I can hear it in his voice.

I can see Claire almost jumping out of her skin with every stroke. It makes me wonder if Colette has ever let her see Jerry spanked before. Or even hear it. I'd think, as long as Jerry has been Colette's toy, Claire should be used to him being spanked by Her now. But his cries are clearly affecting Claire, too. I'll bet they're getting her hot. I'm not sure, but there's something about the way she stands there that tells me Claire's pussy is on fire right now.

The last stroke leaves Jerry crying nice and hard. And that's what I wanted. I lift his shoulders, putting Jerry back on his knees.

And then there's a knock at the door. I was just getting started scolding Jerry to waste the time until it came, too. I'd planned it.

"Go answer your door, fuck stick! You can't leave people waiting! It could be Kathy!" It's not. I know who it is.

Jerry very hesitantly gets up. He glances down, seeing that he's totally nude. I'm sure he wonders why I'm making him answer the door since Claire could, and Claire has her clothes on. But he reluctantly starts for the door.

Jerry stands behind the door, pulling it just barely open enough to see through the crack. "Can I help you?" He asks tentatively, not recognizing the caller.

"I said open the door, fuck stick, not hide behind it! It's not my fault you can't behave well enough to deserve clothes!" I use a very mocking voice. But then I switch to a firm voice that would make a drill sergeant cringe. " Now open it!"

Jerry cringes. He's still got tears running down his cheeks from the spanking. He opens the door wide enough, about ⅔ of the way. But he still tries to stand behind it.

"All the way!" I snap in my commanding voice. And I tap his thigh, just below the bottom of his globes, to remind him that I expect obedience. I don't care about his modesty.

Jerry gives up. He very quickly opens the door all the way. Until the handle touches the wall. It leaves him, fully nude, shaft sticking out of his hard cock with its little pink ribbon, in full view of the caller. A man he's never laid eyes on before.

The man at the door is Kevin. One of my other toys. One I use for a dildo a lot. Kevin is 21 and looks it. He's slightly stock and beefy, with a pretty nice figure. A very young and manly look. He has short blond hair and a fairly handsome face.

Kevin can't help but laugh at the pink ribbon dangling from Jerry's cock. That's something I don't do so often, so it's something Kevin has neither seen nor suffered before.

"Isn't that a manly looking stud!" I blurt out appreciatively. Kevin has been my toy long enough to recognize my voice. I'm taunting Jerry.

"Yes, Ma'am," Jerry reluctantly admits.

"Well, since you're such a naughty little boy, and clearly you have no idea what to do with your wife's pussy, invite that man in. Politely. Introduce him to your wife. He can be her man for supper tonight, since you're being a dog, you can spend the evening in the doghouse! You will humbly ask him to stand in for you. Now, fuck stick."

Jerry's voice is pure shame. And it's hushed. He cringes. "Sir... please come in..." Jerry invites him.

Kevin steps in.

Jerry very quickly shuts the door, almost slamming it lest his neighbors see something he'd prefer they didn't. Like his cock. He steps over to Claire.

I tell Claire to turn around.

"This is my wife, Claire, Sir... Since I've been such a bad boy, I can't spend our date night with her because Miss Rodgers has to punish me. Will you please take my place and be her... man, while I'm in the doghouse, Sir?"

Kevin, like any man would, quickly looks Claire over. He decides that she's cute enough for him. Not that it would matter. Kevin has instructions, and he knows what awaits those who disappoint me. A night with his balls in my vise. Literally.

"I can do that."

"Oh, good!" I squeal excitedly. "Supper will be here soon! Take your new wife to the table for supper! Like a polite man."

Kevin turns to Claire. "Hi, Claire. It's nice to 'marry' you." He says with a touch of amusement in his voice. Enough for Claire to get the hint that he's just playing along with me. "I'm Kevin." He reaches out and takes Claire's hand, holding it. "Shall we, honey?"

He starts leading Claire towards the dining room. He notices that Claire is shuffling her feet, her steps short. Even though he doesn't know why, or even that her panties are still around her thighs, he slows down. He even pulls her chair out for her.

Chapter Three - The Delivery

I clip a leash to Jerry's collar. This way he'll follow me. I wait until Kevin and Claire are seated at the table, and then I walk over to them. Kevin doesn't need much in the way of instructions. He already knows that he's here to be Claire's "date" for the night. It's a role he's filled several times before.

He doesn't know what I'm going to tell him to do with Claire. As far as he knows, Claire is just Jerry's wife. That's all I knew about her when I called Kevin earlier. A vanilla wife. But that doesn't mean I won't loan Kevin to her. And he knows that from experience. The only difference is that a vanilla wife gets a choice to use him.

"Claire," I begin firmly, just to make sure that I have her attention. She has this kind of... dazed look on her face. As if she's stunned by the latest turn of events. She might be. A lot tonight has been different from what Colette does. Colette never pays much attention to Claire, seeing Claire at most as an audience for Her show. That's Claire's fault, it's what she told Colette she wanted. Colette doesn't usually bring Her other toys around either. That's a very rare thing for Colette. She told me that She's never brought one to play with Jerry. Or Claire. I, on the other hand, enjoy mixing my toys up! It's like sending my Barbie doll on a date with GI Joe - while Ken had to watch! I guess my inner imp was just as evil when She was a baby inner imp.

"While I deal with fuck stick and his obscene naughtiness, Kevin here will be your husband for the evening. After all, it's not fair that you miss your date night just because this fuck stick can't stop cumming all over everything. Well, I guess he will now since I stuffed a cork up his cock!

"You are going to be nice to Kevin. Just pretend he's that fuck stick, only better behaved. And younger. And cuter. I expect open, honest, and personal conversation over dinner. The very same conversation you'd be having with fuck stick. I expect you to treat him as if he were fuck stick, just in a better body.

"You are also going to mind your manners like a proper lady bitch. You will be very sweet to Kevin. And very humble and polite to me and my slave... And everyone else. Except for fuck stick, a naughty dog like him doesn't deserve the politeness you show a cockroach. You do not want to disappoint me. Not after I've been so nice and found you not just a stand-in, but a stand-in that's clearly a superior partner. I know you've been married to fuck stick for a while now, but try to remember what it was like to date a higher life form, such as a garden slug. Be very sweet."

They definitely make an odd-looking couple. Kevin is dressed nicely, but young. Like a college guy, which is what he is. He's not wearing a fancy suit, just khaki slacks, and a pullover shirt. Claire's dress... I'd bet that's worth about a grand. It's cut like it's going to have some designer label in it. They look more like a mother and son having a meal than a couple. I do hope Claire can manage to channel her inner cougar tonight.

I walk Jerry back to his bedroom. Colette told me about the one thing she makes him keep available, right in the front of his half of their shared closet. She makes him keep a pastel pink dress, with all the accessories. Like stockings and a garter belt. That's all in light pink as well. She told me that she makes him wear it about one session in ten. Sometimes he needs a reminder of his place. As her toy.

I just want to degrade Jerry as much as humanly possible. I'm sure I could do better if I hunted through Claire's things, but Claire is about five sizes smaller than Jerry. I can tell that much just looking at the pair of them. I'm sure Colette could, as well. I'm sure that's why she made him order the outfit in his size. But it does limit my choices to one.

I get out the stockings and garter. Then I watch as Jerry blushes lightly and pulls them on. It's immediately clear to me that Jerry loves the outfit as much as he hates wearing it. It's giving me a mental picture of the kind of man that Jerry is. He's manly, and it's important to him that others see him that way. Nothing is going to humiliate him more than emasculating him. I'm sure Colette has figured that out too. Thus the outfit.

I give him the shoes to go with it. Those are pastel pink as well. With pointy toes. And high heels. Luckily for him, they're not also too spiky heels. Spiked high heels are a beast to walk in! These shoes will be uncomfortable enough that he won't forget what he's wearing.

Then there are the panties. Colette has picked some cute, tiny ones. Ones that have narrow ribbons for the sides that tie in cute bows at his hips. And won't cover more than half of his bottom in the back. I hold them up. But then I see on Jerry's face a tiny tinge of relief. A very embarrassed relief, but enough to let me know he'd prefer to wear the panties than to walk around with his hard cock jutting out and waving its pink flag. I slip the panties over his cock, draping one of those tiny ribbons over the base of his steely hard shaft. The panties dangle from his cock, hanging down with the fabric that should cover his pubes and bottom dangling just beneath his balls. I decide they look better there, just dangling from his stiff cock.

Now, Jerry is dressed for the night. He looks ridiculous in pink stockings with a garter and heels. More ridiculous with pink panties hanging off his cock.

I walk Jerry back out to the kitchen. I have him turn the oven on. That will make a nice warmer to keep the supper hot until it's served, course by course. Then I walk him over to the table where Kevin and Claire are sitting. Both are clearly watching Jerry. Kevin giggles a little at the sight of Jerry. And I can see that Claire wants to as well. She just manages to put her courtroom face on. I'll bet it's the same face she uses to urge a jury to acquit a client she just "knows" did it. She is a lawyer after all! I just hope she's not as sleazy as the defense lawyers on Law & Order. Or worse, as sleazy as the average ambulance chaser around Mobile, an especially slimy breed that I love getting my whip on.

"Hello..." Jerry begins once I've brought him over to the table. "My name is fuck stick and I'll be your waitress tonight. May I get you something to drink?" I've told Jerry he's to be a good waitress for them. That I expect him to act just like a waitress. Because that's all he is now. He's not Claire's husband anymore. He lost that position when he came without permission. He's just the waitress I brought to serve Claire and her husband Kevin on their date night. Should he forget his role, he can go back over my knees and be reminded of it.

Both ask for a glass of iced tea. But I can hear the faint hint of amusement in Claire's voice. As if she finds being waited on by her husband, while she's sitting with another man, entertaining. I'll bet she's finding it arousing, too. And praying that I won't notice.

And then, exactly on time, the doorbell rings. I take Jerry to answer it. Along the way I warn him that's he's not to try and hide behind the door like he did last time. He's to answer it as a proper servant would. Or else. And I remind him that I won't be the least bit humiliated. I'm not the one dressed like a "porno circus clown." And I don't care one fraction of an iota if he's humiliated. But my paddle would love another workout tonight. It just can't get enough naughty bottom!

Jerry gets my message. He sucks in a deep breath and opens the door wide. Immediately he cringes hard, shirking back, and blushing to a bright red.

There's a woman standing there. Her name is Hailey. She's the GrubHub delivery girl. She's also my delivery girl. As in she's another one of my toys. I told her to make sure that she got the delivery for this address tonight, and that I'd order from O'Charley's. She should be here at ten till six. She already knew I meant for her to be here exactly on time. But beyond that, I only gave her one other instruction.

But all Jerry can see is a woman he's never met. A 20-something woman. She's 5'5", and about 130 pounds. She has short, dirty blond hair that's straight and cut close to her head. It hangs down only to the bottoms of her ears. And covers her ears. She has green eyes. A slightly wide nose. A wide mouth framed with fine, light pink lips, and a huge smile.

And right now, that huge smile is laughing. Those bright green eyes are locked on the pink flag sticking out from his cock as well. She's laughing hard. So hard that she almost drops the bag in her hands.

Hailey has a good body and she knows how to flaunt it. She's wearing a light yellow-green and sleeveless top. It's just snug enough to show off the ample mounds on her chest. She's paired it with a short white skirt that covers her only to mid-thigh. It flaunts her lithe legs. According to her, the attire helps her tips considerably.

'Uh... your supper delivery..." Hailey finally manages to get out over her laughs. She never takes her eyes off of Jerry.

Jerry cringes harder. I'll bet he'd love to run right now. Instead, I tell him to "show this nice girl where the kitchen is."

Jerry's voice is very hushed and completely humiliated, as he politely asks her if she'd mind bringing it in. That's something most delivery girls wouldn't do, at least not for a man. Especially a naked man. But Hailey can see me, and she knows that I expect her to bring it in. So, like the good toy that she is, she brings it in.

Jerry wants to run to the kitchen. Anything to get Hailey gone quicker. Too bad he's still on his leash and can't. I walk just slightly slowly as I lead him back to the kitchen. Hailey follows him. I'm pretty sure she knows that I've ordered for two. I think the drivers know what they're picking up. And I know she can see the couple sitting at the table.

Kevin and Claire are eagerly watching the show. Watching Jerry, in his outfit, lead Hailey into the kitchen. Kevin, obedient boy that he is, gives Hailey only a brief glance, even though she's far more his type than Claire is. Hailey isn't 16 years older than him. Hailey has a nicely toned body, too. He's never seen Hailey before, so he doesn't know that she's one of my toys. So he can't give it away to Claire.

Jerry hurries to get the food out of the bag and into the oven where the hot courses will stay hot. Then, with Hailey still waiting, I tell him to quickly serve "the cute couple" their salads. But not in the cheesy Styrofoam containers. He can move them to real bowls. And he can put the dressing on them. Like a good waiter should.

Hailey just watches his cock bounce around as he hurries to get the salads on the table. I can't blame her. His cock bounces. It waves the little pink flag around. And it stays as stiff as ever, holding the dangling panties up nicely. I'll bet Hailey is thinking of all the mileage she could out of a picture of Jerry.

Once the salads are served, and Claire is enjoying her meal with Kevin, I have Jerry lead Hailey back to the door. I'm pretty sure Jerry's used GrubHub, or Uber Eats, enough to know that she's already been tipped. It's in the charge.

Hailey does exactly what I told her to do. She waits until Jerry gets her to the door. "Would you mind if I used your bathroom?" Hailey asks politely, "I really have to pee!"

Jerry cringes at the thought of her being here any longer. At her having the extra time to look at the humiliating display I've turned him and his cock into. But he can't refuse. That wouldn't be polite. Just in case he was thinking of being rude, my icy glare tells him not to dare to refuse her.

"I guess that would be okay..." Jerry says very reluctantly.

I don't want to give Jerry time to realize what I'm going to do. I just pull hard down on the leash. At the same time, I use a foot to tap the backs of his knees hard enough to jar them forward and buckle his knees. The combination of the two drops him hard onto his knees.

"Uh!" His mouth hangs open as Jerry gasps in surprise. His eyes go wide, startled by both the sudden violence of it and the fact that I'm putting him on his knees when he's expecting to show her where the bathroom is. He clearly hasn't figured it out yet.

I keep the tension on his leash, putting a hand to his shoulders. I feel the resistance of his strong muscles as I pull him to sit back and kneel properly. Then I grab hold of his head, letting his short hair lace through my slim fingers. There's almost enough hair for me to get a good grip on it. Almost. I have a grip on his head, my hand at the hairline on his forehead. And I have a half-grip on his hair. I jerk hard, yanking his head back so that Jerry is staring up at the ceiling.

"She was asking me, you silly little fuck stick!" I scold him in a very mocking, bullying voice. "No one would ask you anything! No one cares what you want or think, fuck stick!"

I put my foot on the leash, using it to hold the tension on his leash. Jerry scrambles to get his hands behind his back again, where he knows they belong. I keep going, leaning him back a little until he has no choice but to use his hands to keep himself from falling over backward.