Daddy's Dungeon Bail

A few of my guests giggle lightly at Emily's comment. It's hard not to. "Nah, " I add teasingly, "I've seen it all. Slave has, too." Emily misses it at first, but a half-second later she cringes as it dawns on her that I'm telling her I've done all of that to her father. And he keeps coming back for more of it. Noting how Emily feels about anal violation, I decide right then that if I ever get another chance at Emily, I am so going to poke up her bottom. I half think about making myself a chance, but decide that wouldn't be fair.

With a wink from Ellie, Ellie says, "Emily, I'm Ellie, I hear we have some friends in common. Come join us?" She shoves her companion over, making room on the sofa next to her for Emily. Emily, thankful to get off center stage, takes the seat beside Ellie. "She mentioned it to me," Ellie asks once Emily has taken the seat, shying as far from Ellie's friend as possible, which puts about an inch between them. "Someone is dating someone's sister or something?"

"Oh, like, yeah!" Emily eagerly blurts out, "My BFF, Livvy is dating Kyle. Kyle's sister, Amanda, is BFFs with Roxanne! I've heard so much about you! It's like I know you already!"

"I know Rox pretty well, and I've met briefly Amanda a few times. I haven't meet Kyle yet, though. Rox, however, is a total sweetheart!" I've met Roxanne, maybe twice. She's a hippie, even by 1960's standards. But she is really nice. And I'm pretty sure bisexual.

I just snap my fingers and hold my hand out. "Paddle." Sophie hurries off. She's back in less than half a minute, gently putting the handle of my preferred paddle in my hand. It's 18" long, 4" wide, and a mere ¼" thick. It's made of two layers of soft rubber with a thin sheet of spring steel sandwiched between them to give it a rigid shape and firmness. The handle is wooden so I can get a good grip on it.

I look up at Ken and grin. "Okay, naughty little boy, bring that bottom over here so all these actual people can watch you get spanked like a miscreant toddler.

Ken comes over, his steps slightly hesitant. His eyes anxiously dart around the room, checking out my guests. All of whom glare at him, most with scorn and amusement in their eyes. Especially Andrea's friend, the gay man, who has the most disdain on his face. I see Ken cringe when he sees the gay man looking down on him as if Ken is much less of a man. And clearly, he's no more taken by Ken's little dick than any of the girls are.

I bring Ken over to my right side, then push him down by the shoulders to his knees. With a good grip on his shoulder, I pull him forward quickly, pushing him down at the same time, until his chest and stomach are lying across my knees. As it always does, bending his waist close against my thigh has the added effect of trapping his stiff cock atop my thigh, his pubes pinning it in place.

I wait for half a second. Ken squirms himself into a position where all his weight is on my legs, then stills himself and picks his head up. I lie the blade of the paddle very softly against his cheeks. It has him facing my long sofa where Andrea, Izzy, and their companions are seated, his eyes almost directly at Andrea's friend. I couldn't have planned the seating better if wanted to! He obediently turns his head to look mostly towards Emily. "Miss Porter, I am sorry for being a bad boy. Thank you for taking care of me while I was waiting for my punishment, Ma'am. Will you please watch Miss Rodgers spanked me really well for being so bad, Miss Porter? Please, Miss Porter, I want you to see me spanked like a bad little boy." He tells her obediently before turning his head straight.

"You're ten swats from getting you collateral back, girl." I remind Emily, "all you have to do is see what a spineless worm this dick-less eunuch that claims to have somehow sired you really is." I hold the paddle still across his bottom, making him feel it and think about the sharp sting he's about to suffer. "I hate to insult a woman I don't know, but I can see why your mother left him. There's no way that little thing could satisfy his hand, let alone a pussy. I just can't figure out how he ever sired you! I can't believe she let him touch her with that thing. I wouldn't. Would you?"

Emily shirks slightly, which backs her up against Ellie, which makes her shirk inward a little more. "uh... no, I guess not..."

"Oh, I get it, girl! You want your man to be an actual male, not a eunuch with a little finger!" It gets a good laugh from everyone except for the cringing Emily.

I bring the paddle up high. I snap it down, it's blade cracking loudly and sharply against his hairy cheeks. His cheeks show their age. They're a little bit loose, with a trace of flab to them. They look like he's spent a lifetime sitting on them instead of exercising those muscles! Which he probably has. The looseness, the slight flatness to their tops, just makes the crack ring out that much louder.

Ken cries out a squeaky "YE-OW!, OW! OW! OW!" and pants a couple of fast, strained breaths. I feel his hips jerk forward, going nowhere, against my thigh as the strike lands. "One, Ma'am." Ken counts, his voice betraying the strain he feels. "Thank you for spanking me like the naughty little boy I've been acting like Ma'am."

As I lift the paddle off his cheek it glows with a wide pink stripe across the tops of his furry globes. I raise it up just as far and snap it back down. This time Ken screeches out his yelp. He tenses hard again, and I feel his hips snap against my thigh. I also feel his snapping hips as they grind his trapped cock between my thigh and his bushy pubes. I feel it twitching crisply against me, even through my jeans, but not moving. His weight has it to snugly pinned in place. It takes him several seconds to stop himself from crying out and count the stroke. And it's only his second. But it leaves his butt nicely pinkened.

The third gets a screamed yelp from him. And a hard cringing shirk back from Emily. I can see she wants to avert her eyes, to not have to see her father spanked like a little toddler. But I also see the determined look on her face, a look that convinces me no matter Ken suffers, her eyes aren't turning away. Not now, not after all she's done to get that video back.

The fourth makes Ken stiffen up so hard that his back jumps just slightly. He screams again, now falling into a sob as he counts his stroke.

The fifth is the one that does him in. As soon as his scream fades, he falls into a bawling cry. Then he counts out the stroke. As I raise the paddle I can see that his bottom is a bright, angry pink, but barely red yet! What a sissy, I think to myself. Girls take it much better than he is. I hesitate just a second and ask him, "aw, does your naughty bottom hurt?" in my most sugary-taunting voice.

He answers "Yes, Ma'am," through his bawling sobs. Just as he makes it to the last syllable, I snap the paddle again. It surprises him, and he screams out a very high-pitched girly shriek. And now, his bottom a mere light red, he cries like a baby girl. Through his sniffling, squeaky-bawling cries I can barely hear him count the stroke. But I do hear Ellie's friend mumble, "what a pussy, take it like a man!" I just hope Ken heard it. The shudder that runs through Emily tells me she did. The boy turns to Emily and says, "Sorry, that wasn't nice of me."

I swat him again, not easing back on my strokes even a tiny bit. Now he screams a shrieking girly-high cry between bawling sobs. When he counts his seventh stroke off, he blurts out his words pleadingly, more sobbing them than saying them.

It gets him exactly what he deserves. His eighth stroke. As he counts it off, I hear Andrea's friend softly saying to her "what a sissy! He's even all snotty like he's two!" I now really hope that Ken heard the effeminate homosexual man call him a sissy. That has to be humiliating.

He takes his final two strokes just as shamefully. When I'm finished, his bottom glows a bright, but not a deep, shade of red. A shade that I know will fade before he goes to bed tonight and leave not a hint of a bruise. I hear Emily sigh out with relief as I push Ken off my knees and onto his beside me. I hand the paddle back to Sophie so she can put it away.

"You filthy little boy!" I scold him sternly, in prim matron voice. He shirks back from my voice. "Just what kind of perversion has gotten into you! You got your little wee-wee so hard while you were spanked! That's so disgusting of you! Obviously, you haven't learned that your teensy little wee-wee needs to behave, too. Go apologize to everyone for what you did and thank them for watching your spanking. I'd apologize for acting like a girl, too. Then I'll take you to the training room and we'll teach your little wee-wee how to behave! Go one, little Kennie."

Ken gets to his feet. I'm pointing to Emily, so he goes there to start. He kneels in front of her, his legs spread fully to leave his cock jutting out into thin air, pointing up straight and stiff at Emily. He looks her in the eyes. "Miss Porter, I am sorry for being a filthy little boy and playing my tiny pee-pee. I know it's wrong for little boys to do dirty things like that, Ma'am. Thank you for coming over to see me get the spanking I deserved for my disgusting sin, Ma'am. I'm sorry for crying and acting like a two-year-old girl for my spanking, Ma'am. I know I should act like a boy, Ma'am. Will you please forgive me, Ma'am?"

"Fine, whatever," Emily says with plenty of distaste in her voice. I doubt Ken recognizes that her distaste is for having to be a part of this, not for what he did. He thanks her again for forgiving him and moves over to Ellie. He doesn't know Ellie's name. I didn't bother to introduce him to any of my friends. So he simply uses a polite "Ma'am" to address her.

I see his cock snap with a hard twitch as he apologizes to Emily. Then another couple of twitches, albeit not as crisp of twitches, as he apologizes to Andrea's overtly-gay companion who stares down contemptuously the entire time. I even make him apologize to Sophie. Then I go around the room and ask everyone if they thought his apology was sincere and humble enough as if he's truly repentant of his "sinful filthy ways." Everyone says they are.

I stand. "Now we'll teach your disgusting little wee-wee to behave itself!" I reach over to his pubes, cupping my hand over his tight scrotum and gently, but firmly, gripping his balls in my hand. "Come." I don't wait. As I start heading back for the playroom, Ken follows his balls. Which I used for a leash.

Five minutes later I have again tied to the table, just as he was Friday evening. Sophie lets Paige out of her kennel, and I send her to tease Ken until his "little wee-wee learns to be good." I leave him with Paige teasing him and return to my guests in the living room.

Once I'm back in my seat and Sophie has freshened up everyone's tea, A snap of my fingers is all it takes to cue Sophie. She goes to my desk and gets the envelope with Emily's video in it. She carries it over to Emily, kneels down, and offers it out politely. "Miss Porter, here is your collateral, Ma'am. My Mistress is very pleased with your attentive guardianship of that filthy worm, Ma'am."

Emily all but snatches the envelope off of Sophie's hands. She runs her hands over it, feeling that the card is still inside it. She takes a few seconds to check the seal, seeing that it hasn't been opened. She folds it up and stuffs it in the front pocket of her jeans. Then she breathes a sigh of relief. "Am I done now?"

"You can be." I tell her softly, "or you can hang out and have tea with us."

Emily can't resist the offer. She instantly falls into her gossip-girl bimbo persona and very eagerly joins the conversation. She happily pumps Ellie for every morsel she can. By listening to them, I learn that her companion doesn't hang out in a lot of the hippie places Ellie does. He doesn't know Roxanne, and thus no one who knows Emily. Ellie chose her companion well. I only wonder if Emily is going to end up telling on herself. I know Ellie won't give anything away. She'll probably mention the afternoon, but without names or anything else that would hint at who is on my table. Emily, however, might well boast of this afternoon to Roxanne, who I'll assume is smart enough to put Emily's story together with Ellie's and figure it out. Or maybe Emily is smarter than she looks. Izzy asks her what the collateral in the envelope is, but Emily steadfastly refuses to answer that one. I see the impish smirk on Izzy's face, telling me Izzy (and probably everyone else) knows what's in there. Emily just doesn't have a clue they've all seen her rather enthusiastic orgasms, and our little chat afterward.

We chat for close to an hour. After two minutes with Paige, Ken is moaning loudly and sweetly, but also even more pleadingly urgent. His moaning doesn't seem to distract anyone from a nice conversation, though. Certainly not me, I can ignore it easily. Emily seems to as well, or at least she's so enthralled with the conversation that she doesn't care even a bit if her father is suffering in the next room while she chats.

Finally, I sigh and suggest "I guess we ought to take care of that whiny boy now..." In my bubbly happy voice, I add "Hey, why don't you all come along! Dick-less won't mind!" I'm on my feet in a snap. Andrea is up just as fast. Izzy just rolls her eyes before gets up, her companion following her. Then Ellie and her friend are up. No way is Emily allowing herself to be left out. She's up with our herd, and soon everyone is following me back to the playroom.

Paige is in the same place, wearing her chains and nothing but. Then again, I have the only key to Paige's chains, so wearing them isn't much of a choice for her. She very eagerly licks and nibbles Ken's cock.

Ellie's companion immediately notices Paige. His eyes spend several seconds roaming over her youthful, lean, and curvy body, taking all of her in and clearly appreciating it. He manages to survive about ten seconds of that before I see Ellie's elbow tap his stomach and we all hear him grunt. Looks like he's in trouble! I'll bet Ellie is going to give him hell for ogling my skanky whore.

Emily takes a place up near Ken's shoulders. She stands there but pays him no attention. Instead, she's focused on us.

I move up to Ken's head and reach down. I lightly stroke his cheek as I ask him in my sweetest and most taunting voice, "has my naughty little boy learned that he has to behave with his little wee-wee?"

"Yes, Ma'am!" Ken shrieks, his voice high-pitched, girly, and desperate. He lies, squirming powerfully against the ropes and ratting the chains on his cuffs. His mouth hangs open as he pants his long moans.

"Does my little boy want to cum like a big boy?"

"Yes, Ma'am! Please, Ma'am!" Ken shrieks out.

"I'll bet you'd really like it if one of these ladies here was super nice to you and took care of that for you, wouldn't you?"

"Yes, Ma'am! Oh, Please, Ma'am!" Ken shrieks very hopefully and eagerly. I'm sure he expected to get his relief by masturbating. That's almost always how he gets his release here. I'd never touch him, not like that! Nor would I allow Sophie to, not that she'd have any interest in doing so. Even though she's strongly attracted to men. I would tell Paige to do it. She's my whore, and that's what whores are for! But Ken's not worthy of even the sweet attentions of a skanky whore - like Paige. Unless he's dumber than my goldfish, he should know that my friends know what a man is built like, and it's not like his little thing. They wouldn't want it either. And apparently, even his barely-18-year-old daughter prefers better (or at least adequately) endowed men. Thus, he should know that his only options are his hand and the hole in my wall.

"It's just been so long since a female actually touched that tiny dick for you, hasn't it? Go on, little boy, tell my friends who last touched it and when."

"Yes, Ma'am. It's been almost three years, Ma'am. My ex-wife, Tammy, was the last girl to touch my little pee-pee, Ma'am." Ken's shame is long gone. Out the window. Replaced by his desire to please me and thus earn the release his cock is killing him to afford it.

"Did she touch it a lot for you?"

"No, Ma'am! She'd only do that for me if I was extra special good for her, Ma'am!"

"Did she use her hand?"

"Sometimes, Ma'am, but not much."

"Did she use her mouth?"

"No, Ma'am."

"Did she let you use her pretty pussy?"

"Yes, Ma'am, if I was very good."

"Did she let you touch her bottom?"

"Oh, no, Ma'am! She'd never let me near that, Ma'am."

"Did she let you use your hand?"

"Yes, Ma'am, but only when I was a good little boy, asked, and she watched me to make sure I behaved myself, Ma'am."

"Has a girl ever sucked that cock?"

"No, Ma'am... Miss Tammy would never put something so filthy as my little pee-pee in her mouth, Ma'am."

I stroke his face a little more, tenderly. I already knew all of that. I'd long ago made him tell me all about what he's done before. So I knew that "Miss Tammy," mom to Emily, wasn't much of a Domme. She was more of a control freak, and she quickly figured out that sex was the perfect stick to control Ken. So she used it, playing along with his hidden fantasies to get her way. But she never did much else, such as spanking him. She just allowed him sex when he did what she wanted him to, and denied him when he didn't. It worked. Ken wanted, craved more, but never dared to say anything for fear of losing what he had. I only make him tell everyone now because Emily is here and I want her to hear it. I want her to know her father. Especially the little part he's trying so hard to hide from the whole world, most especially from her. It doesn't hurt that my guests get to hear it, too.

I go around the room, starting with Andrea, and ask her if she would like to "help Ken with his little problem." As I knew Andrea would, she laughs hard and long before firmly saying "I only touch men. Men have dicks. That stub doesn't come close to measuring up." then she laughs again. Next Izzy, and then Izzy's friend Krystal less insultingly say the same thing: not me. I ask Ellie's friend next he very politely tells me "sorry, I don't swing that way." I ask Andrea's friend next. He giggles and says "Sorry, I prefer my men manly." I so hope Ken heard the slightly-flamboyant man call his cock less than manly. Ellie declines as well. And there I stop. Sophie and Paige don't get asked. Both are my property. Both will eagerly do it if I tell them to, or not if I don't tell them to. They're good girls. I don't ask Emily either. I don't see any reason to put her on the spot.

"Well, I guess that's it. No one wants to touch you. I didn't ask your hand, but I'm sure it doesn't want to touch that tiny dick either. And I know my wall doesn't want it anywhere near the hole in it!" That gets a little chuckle from the crowd. A deep blush from Ken. And a slight blush from Emily, which I attribute to her seeing the obvious shame and humiliation on her father's face.

"Do you like that skanky whore's mouth?"

"Oh, Yes! Ma'am! Her mouth is wonderful, Ma'am!" Ken shrieks out, his enthusiasm back full force as he thinks, or at least prays, that he might finally get a blow job and a very slutty-good one at that.

"Do you think it's skanky pussy might be good, too?"

"Oh, Yes! Ma'am! I'll bet it's the best pussy I'll ever get, Ma'am!"

"How about her hand? Would you like to feel her soft hand loving stroke that tiny thing?"

"Yes, Ma'am! Please, Ma'am!" Ken is just as eager for her hand as anything else. He's just eager for the very rare treat of having it done for him, something that hasn't happened for him since his ex-wife ran off.

I laugh. "Nah, I don't think I want to dirty up my skanky whore by letting it touch a filthy little boy who can't stop abusing his little wee-wee." I get a laugh from Andrea, too. Her laugh is contagious and gets a few of the others laughing as well.