Daddys Dungeon Bail

Prologue:

In case this is the first of my stories you've read, there are a few things I've skipped over in this story since there are several other stories I've written about this same sub. I tend to write a story after almost all of my sessions with my toys. But I publish very few of them online.

My name is Pepper Rodgers. I'm a 19-year-old Domme, living downtown Mobile, Alabama. I have a decently well-stocked playroom in the second bedroom of my fourth-floor apartment (most of my neighbors are corporate types who aren't always around, giving me a lot of privacy, even in the halls and elevators). I also have a decently stocked toybox. I prefer my toys to be older than I am, around 30-42 years old. I prefer men for myself, however not for my toybox. When it comes to toys, I find women and couples to be far more amusing. Single men tend to be needier, and often too clingy. But that doesn't mean I don't have a few of them in my toybox. I do. They just don't have the same chances of getting there as couples and single women do.

I'm petite. Actually more "tiny" that petite. I'm 5' 1.75" and 91 pounds. I'm not bony, though, I've curvy, like a small-sized woman. I have blond hair down to my shoulders and blue eyes. Oh, and my chest is the only place I'm not small. I'm a 32-D, and I'm very pert. Which makes me popular with the boys.

I'm also slightly bisexual. I'm attracted to men, not women. I would never choose a female partner for even a date, let alone for sex. But I'm not opposed to masturbating with a female toy. Sophie happens to be my favorite sex toy to pleasure myself with. Her tongue has two big advantages over my vibrator: one, it's very delicate and tender. Two, no matter how much I use it, its batteries never die at the worst possible moment! It's better than fresh bunny batteries, it just keeps going until I want it to stop. And I don't even have to hold it in place!

When I want sex I never use one of my toys. I never allow a toy touch, or even see, all of me. And I never bring a toy to my bedroom. Nor do I chose a woman. I pick a man, usually one I find in a club or cafe, or wherever. I flirt, dance dirty a little and if he meets my standards, I ask if he's interested in a one-time-only, no-names-exchanged, hook-up. I've never been turned down.

I have a few standards for my hook-ups. I never pick a guy I know or even just see around. And I insist on a cock between 7 and 9" long and 1.5" across, plus or minus a small bit. I won't touch a guy who isn't circumcised, either. I hate the way the foreskin feels inside me. I want to feel that fat head. The dirty dancing gives me plenty of time to tease a guy hard and feel for myself what he's got. It's the only way not to be disappointed. Guys always lie about their equipment!

Sophie is my 19-year-old live-in slave-girl. She's slightly petite at 5'4" and 119 pounds. She's pretty, too, with long honey-blond hair, green eyes, and a 34-B chest. Sophie is extremely devoted to me. So devoted, and so happy as my slave, that despite not being attracted to women, she's a virgin with men. She serves and pleasures only me, and those I give her to. And while I use her, even with my male toys, I won't allow any man to touch her pussy or penetrate her bottom. Those are mine. Only mine. I've owned her since she graduated high school, but I've known her longer. Since about two months after her 18th birthday, which was also about two months before she finished high school.

I have three BFFs, (Isabelle, Reagan, and Ellie) none of whom are into my little games. But all of whom occasionally creep into my stories. After all, they are my BFFs so they tend to be around. Luckily they're not offended by anything they happen to see. They're just not eager for me to put on a show on their account.

I also have a circle of five other women friends, all of whom are Dommes as well. Andrea (26), Janelle (35), Colette (39), Diane (43), and Olive (44). we usually get together every couple of weeks for coffee and a little chat about who's doing what to whom lately. We sometimes share, or loan, our toys to each other, but not that often. Sometimes we do a favor for each other, such as providing something different for a toy. Mostly we do what girls do: we gossip.

I get all of my toys through networking. It's almost always either one of the women in our circle who has a toy she doesn't want and offers to point it at another who is interested. Or sometimes one of my toys tells someone, who tells someone, and so on until someone asks my toy to introduce someone to me. Rarely it's someone I don't play with, but who knows what I'm into, who asks me to meet someone. I get plenty of emails inquiring about meeting me, and while I will email and maybe chat with a sub online, I haven't yet met any. I won't rule it out, but meeting online is risky enough that someone would have to convince me before I'd think about it. A girl's gotta be careful!

[Note: Mistress Pepper and Sophie are "anonymized" versions of me and my slave-girl. The real me. All of my stories are (or should I say will be) my memories of a session with a sub. Thus, they are true stories, only in this version details have been changed to protect the sub. I do live in Mobile about 10 months of the year (the remaining two I spend in Nizhny Novgorod, Russia, where my father is from and lives), and almost all of my subs live in Mobile or a bordering county. I'm originally from Baldwin County, next door to Mobile. I moved across the bay to attend USA. As is/did Mistress Pepper. But I'm not a blond. And you'll most definitely have to guess at my bra size! Enjoy the story!]

Part I: Naughty Boy

My toy tonight is a 40-year-old man named Ken. It's the fifth time I've had him over to my playroom to serve as my entertainment. He's slightly tall and equally thin. Plus he's an accountant by trade. I hate stereotyping people, but in this case, it fits. He's rather boring out of the dungeon. Or rather his life is. But once in my dungeon, he eagerly serves my whims.

About three years ago, Ken's wife told him he was "utterly boring and pitiful" of a husband, then she ran off with a 25-year-old carpenter. I'm sure he had a much more manly physique. And I'm almost as sure he didn't have half the brains Ken does. Neither Ken nor their then-15-year-old daughter Emily heard from her for several months. In that time, their divorce became final, the courts feeling that his wife's failure to respond to its summons was as good as answering his complaint. Then she popped up, having discovered that her carpenter couldn't keep her in the lifestyle an accountant could. It was Emily who sent her packing, telling her that she chose to leave, and now she was gone. Ken would have welcomed her back. Only Emily stopped him, insisting that if mom returned, she'd leave and find her own way in life. It was an empty threat, I'm certain of that, but she made him believe it. I'm not sure what Ken would have done. But once Emily proved her point by vanishing for a night, mom gave up on coming back. She tried for alimony and only Ken's lawyer prevented her from reopening the divorce and cleaning him out retroactively. She went away and hasn't been heard from again.

I don't know Emily, even though she's the same age as my house-slave and whore, Paige. They went to different high schools. Paige is from here in Mobile. Emily is from a very rural county in Mississippi just over the state line. That's where she still lives, at home with her father. But my BFF #1, Isabelle, is acquaintances with a boy named Terrance. He's twenty, but he went to the same high school as Emily, and despite the age difference, in his senior year he briefly dated the sophomore Emily. Luckily for me, Izzy is nosy and devious about it. Over the last couple of weeks, she's gotten every morsel of gossip out of Terrance and painted me a fair picture of Emily.

Emily is flighty. And she's a bimbo, with all that entails. But she also has a little bossy streak in her. It doesn't sound like dominance, just bossiness. She can be bratty, and especially sassy, too. She's definitely a party girl who likes to have fun. And she goes through boyfriends faster than I go through cups of coffee. She's pretty (I've seen a picture) but not especially beautiful. Cute enough for the cheerleading squad, even here in Mobile, though. She's not the greatest student, but good enough to get somewhere in life. And it sounds like she's known for making snap decisions, then changing her mind two minutes later. And reversing course several times. And not appreciating it when others don't understand her whimsical mind-changes. Yup, a bimbo. Useless!

Ken has been in my dungeon for around an hour now. I have him on a table I designed and bribed a couple of frat boys to build for me. Okay, I bribed them with Shelbie's body. Their payment was to watch as I tied Shelbie to it, the redheaded 35-year-old with her firm body, nude. Then, for three hours, the two boys were permitted to do whatever they dreamed up to Shelbie. They weren't that imaginative. But they left Shelbie sloppy, like the whore I was making her be. I'm sure Shelbie enjoyed it. She always enjoys it when I give her away to total strangers (to her).

This rack is built like a giant Y. It has slats of 1x6 unfinished boards for legs, and a pair of 1x8s, side-by-side, for a stem. Underneath the slats, there's ample welded steel to brace them up. Except at the junction where all three meet. Or used to meet before they cut that part of the slats away leaving just an empty space there. At the bottom of the six-foot-long slats, there are little winches.

Ken lies on the base of the Y, his legs pulled out onto the slats. I've tied a rope around his ankles, the same as I always do. Three coils of rope wound around each ankle, the loops snugly against each other, then tied off. The free ends of the rope, those I laced through the winch. And then I slowly cranked them tight, pulling his legs taut.

To keep him from simply being dragged down the Y by his legs, there are two inch-diameter wooden dowels sticking up a few inches. Those fit in his armpits. His hands are pulled up under the base of the Y, bound together with handcuffs, and the chain of those cuffs is firmly attached to the underside of the boards. It holds his hands in place, roughly where the small of his back is, keeping him from getting to anything, or from moving his hands enough to get free of the pegs.

To keep him from simply raising his chest up, and thus his arms off the pegs, he's wearing a training collar. I have them in both baby blue and pastel pink. His is baby blue for a boy, but it's also a rather feminine shade of blue. The collar is turned around, its buckle in the back, and its buckle is locked to the table.

It keeps his body taut on the table. And that keeps him from moving while allowing him to squirm around a little. The missing section of the table leaves his bottom hanging out in the air, nothing at all under it. The wide-angle of the leg-slats leaves his cock and balls hanging out too. Or rather now just his balls dangling down. His cock is far too stiff. It stands up, or when left alone lies up along his stomach.

It's not being left alone. Ken is here to accept his punishment for being a bad boy between his sessions. I have all of my toys keep in touch daily. When I got Ken's email this morning, he confessed to masturbating last night. And the naughty boy didn't ask me for permission to play with himself! For that, he's suffering greatly now. And has been since I got him tied down to this table.

Ken isn't a fortunate man. To start with, he's a little on the hairy side. His pubes aren't dense, their hairs short and curly. But those hairs, without thinning out much at all, flow out to cover close to half of his thighs, the bottom edge of his stomach, and the bottoms of his cheeks before they quickly to thin away leaving him "averagely" hairy on the rest of his body.

But that's why I call him unfortunate. The average size of a man's cock is just over five-inches at its full stiffness. Believe it or not, we covered that in one of my nursing classes. Ken's is barely four inches long. Nor is it thick. I know, I watched Sophie measure it. It's a hair over 5/8th of an inch across, even at its pink-purple head. The only thing it has going for it is that it's circumcised.

His balls aren't better. They're just slightly on the small side of proportional for a man his size. But his sack holds them close to his body, instead of leaving them dangle, making it look like he barely has much of scrotum at all.

I'd never date him, let alone marry him. There is no way I'd condemn myself to a life of just that little dick. I like good sex far too much. I suspect, or maybe guess, that his ex-wife's carpenter was much more manly-endowed, and that was a good bit of his allure for her. Then again, he does have enough to make a daughter.

As soon as Ken arrived here I had him strip. I'm sure he expected that, I always make my toys get naked first thing, and stay naked while they're here. Clothes are a very rare exception for my toys that I save for the equally rare times I take them out of my playroom. Then I put him on his knees and spent ten minutes deriding him with a continuous scolding for "abusing himself."

I told him that he would be spanked for playing with my cock without my permission. He's my toy, so I own him. And if I own him, then I own his tiny cock as well. I didn't feel like having my cock played with last night. And I don't care what he thought he wanted. I don't care if my cock throbbed and ached to be played with. I didn't feel it.

But I decided that I didn't feel like spanking him right that instant. So he could wait on the rack until I felt like spanking his naughty bottom. Then I brought him in here and tied him to the table he's on.

I wouldn't want him to get bored while he waits around. It could be a while until the whim to spank someone strikes me. So I decided my house slave, "skanky whore" could use my tiny cock for a practice dick while he waited.

"Skanky whore" is what I call Paige, my house-slave. It's her name, at least as far as I'm concerned. A name I ensure she lives up to. She's 18, about 5'5" and at 120 pounds thin and lean. But she has some proportionally nice, very pert 34-B breasts. They're firm, standing straight off her chest and tapering with more of a cone-shape than a roundness up to wide, light pink nipples that swell up like half marbles when they're stiff. Which they seem to always be.

I've told Paige to "tease" his cock. She knows what I mean for her to do. "Tease" is a specific term for what I want her to do, something I've taught her to perform on command like a trick for a dog.

It has Paige start at the tip of his cock, flicking her tongue over the tip once. That always gets a sharp twitch that makes his cock jump. From there she licks her way down his cock with a single, long stroke of her tongue, caressing it along the underside of his shaft all the way until her tongue has massaged its way over his small sack. Then, her tongue motionless atop his sack, Paige closes her soft lips to completely surround his entire sack. With his balls now captive in her mouth, she flicks her tongue as rapidly as possible, dancing it over all of his sack.

Then she allows his sack to slowly slip from her mouth as her lips move back to his cock. As soon as his lips are on the very base of his shaft, the instant they can feel its stiffness, Paige closes her teeth gently clamping the shaft in place. She closes her lips around the sides of his cock, then sucks very gently as she flicks her tongue over the underside of it. Paige's mouth creeps up the shaft all the way to the very tip.

Once Paige can go no further up the shaft, she uses her head to lift it up, loosening her grip on it just enough that the cock swivels in her mouth until it's pointing straight into her mouth as if she were going to suck it. Paige stretches her mouth wide, taking all of the cock's head into her mouth and closing her lips softly around it. Then, with the head of his cock fully inside her warm, wet mouth, Paige will swirl her tongue around the purplish flesh as excruciatingly slowly as she possibly can. Once that's complete, her tongue having circled fully around the bulbous head, she gently lowers his cock to lie against his stomach. And repeat. And repeat.

On every tenth repetition, and only on those tenth repetitions, Paige will skip the tongue-swirl. Instead of that, and moving just as slowly, she'll take all of his cock into her mouth for a single blow-job stroke. She'll do that just as slowly as she possibly can. And it doesn't matter how much cock he has. Ken's shortness is easy for her. But a giant cock would be just as easy. I've taught Paige to swallow whatever a man has to offer.

Paige will keep on doing that, repeating the ten-repetition sets, until I tell her to stop. While she does that, her hands are very tenderly exploring his chest, caressing him sweetly.

It's not enough to make him cum. Paige obediently stays far too slow to bring him to orgasm. But it is as good as a blow job at stoking up his desire, his urgent need to cum. I've found ten or fifteen minutes of lying there and suffering it, especially with Paige's very loving, tender, hot, and moist mouth, which is more than most men care to endure without release. A half-hour is usually plenty to drive a man mad, at least with Paige's skillful attention.

Ken has been here an hour now. A single stroke was enough to have him purring moans. A second started him squirming, testing the ropes that leave him with no choice but to feel the sweet agony. By the time his cock was fully inside Paige's mouth for the first time, he was gone. He squirmed hard against those ropes, and his moans had risen to an almost-girly-high full of an urgent plea.

Now I have Ken where I wanted him - absolutely desperate for release, and thinking of nothing but the pounding ache in his over-stiff cock. He even has little tears welled up in the corners of his eyes. And all the other obvious signs of the sweetest of agonies, like curled up toes, and his hands clenched into tight fists.

I stand beside Ken's ears and ignore the loud, high-pitched, fast-paced moans he's crying out. "Are you listening to me, dick-less?..." I say it my most taunting, mean-girl, bully voice. "I've decided that, since you snuck off and hid to paly with that little thing, you must like privacy. So you'll be spanked publicly. I have friends coming over Sunday afternoon for tea. You can be spanked then. They won't mind watching your hairy butt go over my knees. And since my friends are girls, they should get a very good laugh when they see how little your dick is."

I sigh out deeply, drawing it out. Then I do nothing. I just stand there for a couple of minutes, letting it sink into Ken's brain just how badly I am going to humiliate him. Like many subs, Ken openly hates being humiliated, but it also arouses him powerfully. And he knows it. It gives him time to ponder the disgrace of it, and think about how aroused it will make him, and how that will only add to his shame as all my girl friends will get to see that it's turning him on faster than a switch would.

"I guess you'll just have to wait here until it's time to spank your naughty little boy-butt." I tease him. Then I wait another couple of minutes. It's time Ken spends crying out moans that are nothing but erotic and desperate pleas for release. And testing my rope-work a little more enthusiastically. But not getting any play from the rough hemp ropes holding him taut.

I sigh again, just as deeply. "But I guess you could have bail... would you like to beg me for bail, dick-less?"

"Yes, Ma'am!" Ken cries out urgently, his voice more anguished erotic moan than words. "Please, Ma'am, may I please have bail while I wait for my public whipping, Ma'am? I swear I'll be back whenever you want me to so you can whip my naughty bottom in front of all your friends, Ma'am! Please, Ma'am, please allow me to have bail!" His voice grows desperate as he begs. Desperate not to suffer any more of the teasing agony of Paige's sweet mouth.