Daddy's Dungeon Bail

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Emily giggles. It kind of surprise me, since she's been so uncomfortable so far. But it's an honest, girly giggle, that I know Ken hears. His cock jumps, and I watch a tiny drop of his cum weep from the tip of his cock and cling to its head. I guess he enjoyed the humiliation of having his barely-adult daughter giggling at the sight of cock. And it was a laughing giggle.

Sophie hands me the chastity device. It's an eight-inch long piece of clear, but heavy, plastic pipe. Its inside diameter is one inch, which is plenty wider than his cock. At the tip of it, there's a mesh-like chicken wire covering it. He can easily pee through that mesh, but it will stop him from reaching in to get at his cock.

A snap of my fingers is enough for Paige to step away. I lift his cock to stand up straight. "If you had two of these, they'd add up to man!" I tease, and Emily giggles another laugh. I lower the tube over his cock. It covers the entire shaft, leaving enough room around it that his cock will only lie against it; no matter how stiff and swollen it gets, it will only touch that narrow sliver at the bottom. He barely fills half the tube's length, and the clear tube shows how far his cock comes from "measuring up."

The tube has little slits in its base end, the end against his hairy pubes. Through one of those on each side, I lace a thin leather strap, bringing both ends of it under his waist, doubled over, before lacing one through the second slit and securing them with a shiny brass padlock after pulling the tight. A similar strap goes around the top of each thigh, lying in its crease and pulling slightly up against the bottom curve of a cheek. Those are locked as well. The final strap is at the very bottom of the tube. It cinches snugly around the top of his sack, pulling his scrotum snugly against the edge of the tube. On his small sack, it just barely pushes his balls down to hang in partly taut skin beneath the strap. If he had a large sack, instead of one that's proportional to his cock and holds his balls close to his body, they dangle under the strap freely.

Now that his cock is untouchable, I have Sophie release the ropes and cuffs holding him to the table. I send her to fetch his things. Then I tell Emily, "I have a rule in here, no worthless, or dick-less, naughty boy is allowed to roam free. Take him by the hand and lead him out."

Emily tries very hard not to look at, or anywhere near, his cock. She just takes his hand, her unease showing and follows me out to the living room. I suggest that she have him sit on the sofa and explain to him the rules of his bail, so there will be no confusion later. She seems to think that's a good idea and leads him to the sofa. The farthest end of it from where she just sat.

I hand her the list of rules he has to live by. I tell her to read them to him, explain whatever she thinks needs explaining, and make sure he understands them. He can accept her guardianship until his punishment or return to the table and await it there. I see a cringing shudder sweep over him as I suggest that she can return him to the table.

"Number one." Emily begins. She stands confidently in front of her seated father, looking down on his nakedness with a cool, hard glare on her face. "I have posted an extremely high bail for you. You may never, ever, ask me anything about it, or what it is. You are so totally going to follow these rules because if you make me lose my bail, I swear, I will kill you in the slowest, most agonizing way I can possibly dream up!" Her voice is definite and stern, and I hear the bossiness I'd heard about in it. That wasn't one of my rules. Emily has added it. I don't see any reason to contradict her. She recites the rest of the rules only very slightly less firmly.

Then she asks him, "are you going to follow them?"

"Yes, Ma'am." He answers in a voice that's pure shame.

"You'd better!" she says, "now get up and put our clothes back on."

"Yes, Ma'am," Ken answers her before getting to his feet.

Part III: Daddy's Punishment

I had no plans for a Sunday "tea" with my friends, even though I told Ken and Emily I did. It took me all of twenty minutes, and a few phone calls to make plans for one. I invited my BFFs, Izzy and Ellie, telling both to bring a guest. But I warn Ellie that some girl she "hangs" with, who doesn't know me, is gossiping down a chain that reaches to Emily. She assures me it won't be an issue. I'd have invited BFF #2, Reagan, but she followed her boyfriend to a college only slightly less reputable than the "Mail Order University of Somalia." It's called Florida State University. I don't know anything about it, but my Gator fan slave-girl Sophie knows all about it. Okay, it sounds like there some intrastate rivalry going on there. I'll accept Sophie's version. It's also about three hours away, which means Reagan doesn't get back to Alabama nearly as often as we want her to! That's reason enough in my book. Then I invite my friend Andrea and her guest, whomever she wishes to bring.

None of my friends would lightly pass up the chance for a meal here. Even lunch, the lightest meal of my repertoire. I'm too good of a chef, and I've taught Sophie everything she knows. She's almost as good as I am by now. Thus all three quickly agree to come over. And none mind that I have a little show planned for their amusement after lunch.

My guests arrive around eleven. We begin with a private screening of Emily's bail video. For a teenager, Emily is surprisingly tech-un-savvy. She didn't even think to consider that my video camera has WiFi built-in! All the good cameras do. Or that my laptop was recording a second copy of her little show, which is automatically stored on a server in Moscow. Oh well, what she'll never know won't hurt me. This copy will be only for my private collection unless Emily forfeits her bail.

Izzy brings a girl friend named Tiana, whom I've met a number of times before. She's a student at USA with us. While I don't know her well enough to consider her a friend, I do know that she's a member of a sorority known for "anything-goes party girls." Ellie brings a guy I don't know. He's around 20, decent look, except that he's slightly scruffy and hippie looking. Then again, Ellie is pretty much half a hippie herself, so they should get along well. Andrea brings another flight attendant. A male one who looks to be in his mid to late twenties, as is Andrea. He also looks very effeminate and sounds it. I'd guess he's gay, and certainly the feminine half of any couple. I have no clue why anyone picked the "plus-one" they did. But I know Izzy likes to tease other girls with a trip here, Ellie likes to see how guys she likes handle it, and Andrea tends to bring either those she's considering as toys or those she's close friends with. I'd guess these companions all fit that bill.

I being by telling them what the after-lunch entertainment will be. "A middle-aged male accountant, completely spineless and just about as dick-less, who disobeyed my wishes will be coming for his punishment. His punishment will be a good spanking. After which he will be placed on the table where skanky whore will see that he doesn't lose interest. If he behaves he may be allowed relief."

"He misbehaved Thursday night. Friday evening I was going to punish him, however decided that he could wait for it. I allowed his 18-year-old daughter to bail him out of the dungeon until time for his punishment. She will deliver him promptly at one. As bail, she made and left with me this very cute video. If she follows all of the conditions of his bail agreement, she gets the video. If she disappoints me, I keep it and might just post it free online.

"And now, for my special friends and guests, we will screen the little slut's collateral." My TV is a 60-inch smart TV. It has built-in WiFi. A few clicks on my laptop, and the video clip, edited only to start when Emily starts, appears on the screen.

The clip is almost half an hour-long, even though less than four minutes of it is Emily's diddling orgasms. I have Sophie serve coffee while it's playing. Everyone watches intently. Especially Ellie's male guest. Men. I see a huge smirk on Andrea's face. I know she loves the shyness Emily shows, and how fully I stripped away her modesty and dignity. I like how submissively she allowed me to.

Then Sophie serves a leisurely lunch. It brings up to around twenty minutes to one. We retire back to the living room, Sophie serving tea, and chat away as we wait for Emily to bring Ken back.

I do find out that Andrea's guest is "mostly gay," as he describes himself. Seeing that no one here really minds that, he willing elaborates that he likes it when a strong, "beefy" man "nudges" him to go down on him. However he thinks girls are pretty as well, and if the right woman, meaning one who was physically strong and somewhat masculine in her ways, would "nudge" him to go down on her, he would so love that as well. He's been after Andrea for ideas of what he might do with his long-time boyfriend to spice it up a little. Andrea, knowing the amusement would be male, invited him to "see if likes something." Emphasis on see. I welcome him and tell him that I'm bi myself. I'd have no trouble "nudging" a "properly equipped" male, or a female, to her knees to service my pleasure. Sophie grins very wide, I'm sure thinking of the countless times I've nudged her to her knees. I just think "nudge" might have a different meaning here than to him.

The knock at my door comes ten minutes early. Emily not taking any chances of being tardy, and thus forfeiting her bail video. I didn't tell her that she had to be precise. I'm sure her father did, but I'm just as sure Emily isn't listening to anything he says now. She's too worried about that video being seen. Sophie answers the door.

"Oh, there you are!" I say as Sophie leads the pair into the living room. Emily leads Ken along by his hand. Yep, this girl isn't going to chance anything. I didn't think she would. Especially now that I've seen the seven emails she sent me, telling me everything Ken was doing, over the course of about 40 hours. Or should I say 24 hours, once the 16 he was asleep are taken out? That's about one every three waking hours. She is so not taking a chance.

"Here he is," Emily says firmly. She glances nervously around the room, seeing that my guests are both male and female. Counting every life form, there are now ten humans and one Supreme Goddess (Lilly the foster dog) in the room, all of who will see her video if screen it. And none of whom hint that I have already screened it for them. I notice Ellie's friend's eyes taking Emily in rather eagerly, but Emily doesn't notice him. Just all of those eyes on her, however, is enough to get her fidgeting slightly. Her voice turns edgy and anxious as she coyly asks, "can I have it now?"

"No," I tell her. Emily trembles, her eyes almost popping out of her head. "You may have it after I am done with this naughty dick-less boy. You still have two things to do. That's not how you got him. And you have to hand him over to me exactly as he was when I gave him to you. That means completely, utterly naked. Second, you did agree to witness the execution of his punishment. Do both of those, and your collateral is yours."

Emily relaxes a little as she realizes that she just might get it back. I pretty much came out and told her that she's done acceptably so far. She turns quickly to Ken. He's six feet tall, so she's looking up at him, her eyes about even with his neck. "Dad, strip, now." Emily snaps rather firmly. Her tone leaves no doubt that she's demanding it.

"Yes, Miss Porter," he politely answers her in shamed voice. He starts taking his clothes off. When Emily doesn't hold out a hand for them, he makes a very neat pile on the end of the coffee table in front of him. He's wearing a Polo shirt and jeans, with sneakers. It doesn't take him long to get most of it off, baring his body to all of these eyes.

He hesitates for a fraction of a second when it's time for his boxers to come off. With them up, the hard tube pokes out a defined bulging outline, making him look well-endowed. He pulls his loose-fitting boxers down, and immediately his cock juts to stick straight out, proudly showing off the clear tube locked over it. And embarrassingly showing of how little of the tube his stiff cock fills. He stands with his hands behind his back, obeying my house rule.

I reach into my pocket and get out the tiny key. It's on a little keyring with a small rubber fob maybe four inches long. The fob is shaped like a hot pink phallus. I hand the key to Sophie and she takes it to Emily. Emily gets the hint and takes the locks off. She pulls the straps out enough that they hang free, and slides the tube off of his cock. His cock still sticks out at us. Emily gives the tube and key to Sophie who puts them on the table.

To one degree or another, all of my guests laugh. Ellie's friend mutters "poor guy..." and Izzy coyly asks her friend (Krystal) "how does he ever get laid with that?" Laughing, Krystal answers "definitely not by me!" Ken stands there demurely, blushing a deep beet red as we all honestly laugh at his cock.

I hold up a pair of latex gloves, showing them to Emily. "I never trust naughty little boys, especially when they're here to be punished for sneaking around to play with their little pee-pee. Would you care to check him yourself and be certain that this boy has nothing anywhere or would prefer to gamble your collateral on his being naked when I check his disobedient little butt?"

Emily stares at me for a split second. It's plenty for her to see the no-nonsense look on my face and know I'm serious. If I find anything, I'll keep her video. As I'd hoped it would do, it motivates Emily to very quickly agree "I'll do it." Then, as Sophie brings her the latex gloves, Emily reluctantly asks "what do I have to do?"

As Emily is pulling on the gloves, I tell her that she has to "look at every single cell of skin she can possibly make a way to see, as well as run her hand or at least a finger over it. "And if I were you, I'd look, and feel, very diligently, lest you miss some tiny thing..."

Emily looks very uncomfortable, and just as unhappy about it. But she does it. I tell Sophie to "help" Emily, so Sophie stands beside Emily and tells her what to do.

The rest of us stand back and watch as Sophie has Emily start at the soles of his feet, running her gloved hands over them and looking at them, one by one, her eyes a scant six inches from his skin. Sophie lets her move up his body steadily and suggests that she save the "more intimate" places for last. When Emily gets to the very top of his head, running her fingers through his gray-brown short hair, Sophie finally tells her "here, use this light and peek behind his ears. Boys are just so untrustworthy!" Then it's peeking in his ears. Up his nose. In his mouth, under his tongue, between his cheeks and gums, just everywhere.

Sophie suggests Emily kneel in front of Ken, to get a better view. She has Emily run her gloved hands over the entire length of his stiff shaft, which makes his shaft jerk hard as eager twitches shoot through it, and then over his balls. Finally, Sophie tells her to very gently pinch the head of his cock to make it's "little hole" open up and look there - using the light - too. Emily looks, but I doubt she sees anything. My guests watch intently, more seeing how uncomfortable this is making Ken than anything.

At Sophie's suggestion, Emily has Ken turn around, spread his feet wide, and bend over to brace his hands on his knees. It puts Ken's backside to us, the audience for this strip search that's far more thorough than any jail's. It also puts his butt a few short inches in front of Emily's eyes. Sophie tells Emily to use one hand to "push those ugly, hair cheeks as wide apart as she can manage so that his filthy asshole can really be seen." While I can see Emily cringing hard, as I'm sure the others can, she obediently follows Sophie's advice.

She pushes his cheeks wide, first baring his penny-sized dark purple ring in all its wrinkly glory. As she spreads them wider, it pulls the wrinkly flesh, partly folded over on itself, fairly taut, stretching out most of the wrinkles and showing us that he's too hairy here too. His butt hair runs almost all the way up to his ring. She holds those cheeks wide, his asshole stretched tautly, but not open, the little dark funnel of it maybe six inches from her eyes.

Sophie tells Emily to run her fingers over everything she can now see, making sure there's nothing there. Emily does it, quicker than she's done anything so far. Done, Emily glances up, expecting Sophie to tell her she's done now. There's none of Ken left for her to look at. Instead, she sees Sophie tearing the corner off a single-use packet of lubricating gel.

Emily cringes so hard we all see it. Sophie tells Emily to give her a finger. Emily very hesitantly, and more slowly, brings up her free hand, her fingers generally toward Sophie. Sophie casually squirts a dollop of lubricating gel atop Emily's first finger. "Now just put the tip of that greasy finger right against the center of that dark little tight hole... aim it for his navel...now just push all of that finger in there. All the way until you can't get any more into that filthy little hole."

Emily pushes gently. I can see the ring of muscle there push in a little, but not give. Her face shrivels up tight as her eyes avert. She pushes harder. Unskilled at this, almost certainly never having to do it before, she pushes a little too hard. Her finger shoves through his ring, stretching it as it slips into the ring.

Ken grunts hard, letting us all know that Emily isn't doing this nicely or comfortably for him. I can see she's doing it clumsily, but so what? It's her first time! As he grunts, I see his cock twitch so hard that it snaps up and slaps against his stomach. It returns to its place, hanging down between his spread thighs, but still twitches.

I signal Sophie to draw it out. Emily sees nothing, trying hard not to. Sophie tells Emily to "use her finger to feel around up that dirty butt," and to "make sure your finger glides over just everything it can reach up there." I watch Emily closely. I can see the tendons on the back of her hand showing me that her finger is moving.

Ken grunts again at the first tiny movement. And his cock jumps again. He purrs a drawn-out, groaning "UH!" as Emily's finger feels around. "Go slow! You don't want my Mistress to find anything you miss up there!" Sophie warns Emily. It makes Emily slow down. Ken grunts with a tiny bit more strain to it as Emily more diligently pokes around up his sensitive butt. His cock twitches sharper with every passing second, too. After about fifteen seconds I see that Emily's finger stops moving.

"Emily, do you feel anything inside his filthy bottom?" I ask her teasingly nicely.

"Just a giant turd I really want to get my finger out!" Emily answers, blurting her words out as pleadingly as they are hopeful and disgusted. I tell her she can take it out now. She yanks it out as fast as she can, which gets another grunt, and about half a dozen good cock twitches, from Ken. She hurries to pull the gloves off, unhappily moaning "EW! Gross!" as she does.

I have Ken stand back up and turn around. As he faces us, his cock still has stopped twitching eagerly, although its twitches have ebbed almost fully. Emily hops up to her feet, turns her back to Ken, and pleadingly asks me, "Are you going to check him now? No way are you going to find anything!"

I grin. "Nope... I'm confident you would have found anything that naughty boy was trying to hide."

"Duh." Emily groans out, "you made me check places I'd bet no one has ever seen before in his life!"

1...345678