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Chapter 49
by
Obedient Lorelei
Which way does Rita turn?
Left, but not for her clothes
"Be right back," she says, slipping through the bathroom door, emerging just a few seconds later, wearing a tiny white dressing gown and a pair of fluffy slippers and carrying a couple of jars, which you recognize as soothing cream and the lubricant you used to prepare for the enemas, earlier. The dressing gown is so small you think it might be intended for a child. The arms stop short of her elbows, the front barely overlaps and it's so short that her bum threatens to peek out beneath the hem. It covers her crotch, but only just.
Once again the only one naked, you continue to feel a bit self-conscious when Rita leads the three of you back into the dining room. The conversation dies down at once, allowing her to announce that Claudia has something to say.
"Um," the embarrassed blonde hesitates, clutching the hairbrush the hostess gave her in the bedroom to her bosom, trying to find the least awkward way of telling her boyfriend she'd like him to start disciplining her. She steps towards him.
"I-I'd like you to spank me, Olly, when you think I deserve it." She holds out the hairbrush. You've not had a good chance to inspect it yet; Rita passed it to her just as you were about to descend the stairs. Now, you can see that it's an old-fashioned style, on the larger side, made of light-coloured unvarnished wood sealed by the application of hundreds, or maybe even thousands, of smacks to the sisters' behinds over the years.
Olly beams with delight.
"Are you sure, Clau? It'd be the same rules as Ricardo: I decide how hard to spank you and if you complain or ask me to stop, I give you extras."
"Yes, Olly. That's what I want." You wonder whether she really believes that.
"There's something else you want to tell him," Rita interjects, "isn't there?"
"Oh, yes," Claudia leans forward to whisper to her boyfriend, but Dora tells her sharply to speak up and, apparently unable to defy her, she does so, announcing haltingly to all present that she's had an enema, in case Olly wants anal sex tonight. You notice Rita, who's now sitting on her husband's knee, murmur something in his ear and he turns to look at you with a quickly-concealed expression of shock, so you're pretty sure he knows about the state of your back passage, although you can't tell whether she also mentioned her own readiness for rear penetration. Everybody else is so busy checking how well Claudia's new make-up conceals her blushes that they miss this entirely.
"I thought you really hated it," Olly replies, attentively.
"Yes, but if I'm being punished, we thought maybe…"
"Absolutely," Olly jumps up and plants a fervent kiss on his girlfriend's lips. "If you're sure."
She nods and he pulls his chair back from the table, before sitting back down and patting his knee. You realize at the same time she does that he intends to spank her right now! After what she's just said, there's no reasonable way for her to back out, so for the second time tonight, the skinny blonde has to wriggle her dress up to her waist and expose her buttocks. She adjusts her top, before realizing the futility of trying to keep her breasts in check when she bends over and resignedly takes her position. Sure enough, her creamy globes immediately fall out and Olly traps her thighs between his own to hold her in place while he thrashes her.
It's all change for the seating arrangements. Dora takes Rita's old chair and moves it beside her husband where the two of them will have a good view of Claudia's behind (and Malc can see her chest reasonably well). Ricardo and Rita place Dora's chair to Olly's left, where they'll be able to watch the girl's face, as long as she keeps her head up. They seem happy to share, Ricardo's hand sneaking under his wife's hem when she sits back on his knee. You quickly stand behind Dora, so you can watch both the spanking and your hosts' responses to it.
Olly takes his girlfriend's right hand in his left and pins it behind her back, then raises the heavy hairbrush and wallops it down, seemingly as hard as he can. Claudia gasps, but he gives her no time to recover, following up with another brutal smack, then another and another. The delicate blonde starts to snivel and you almost wish you'd stood on the other side to see the expression of anguish you're sure she has, but then your eyes are drawn to the movement of Ricardo's fingers inside Rita's dressing gown and you're happier with your decision.
The young man speeds up, positively pummelling his precious paramour's pert posterior into a pulsating purple pulp. She begins to howl and then scream, alternately holding her body up with her free arm and grabbing onto the chair's stretcher so hard her knuckles turn white. Her legs start to drum on the floor and Olly pauses momentarily, but his lover's relief is short-lived.
"Keep your feet still or I'll borrow Ricardo's cane after I've finished with your bum," he warns and Claudia wails in despair, but compliantly pushes her toes to the floor in her thick-heeled sandals. Unfortunately, this is the signal for him to continue brutally battering her blistering buttocks black and blue.
When the blonde's head drops, roaring in agony, Rita uses one slippered foot under her chin to bring her face back into view. From the angle, you're sure she could see right under Rita's robe if she weren't blinded by tears. Your boss is definitely being fingered vigorously and the only thing stopping you from pleasuring yourself in the same way is that it seems disrespectful to the girl suffering so terribly in front of you. Perhaps the thought of how you would be punished for masturbating in public ought to be a deterrent, too, but somehow, it's not.
After what seems like an eternity, Olly finally slows and then stops, shaking out his arm, which gives the impression that he only ceased because he was getting tired, not because he thought Claudia'd had enough. She continues to sob and shriek while he inspects her bruised bottom, mercilessly digging his fingers into her tormented flesh.
"What do you think?" He looks over to his parents, first. "Should I keep going or has she had enough?"
"Oh, she can definitely take more," his mother is the first to reply. "You'd be surprised how resilient girls are at her age."
"Indeed," his father adds. "If you're worried about her backside standing up to it, there are plenty of other places to spank her."
"Remember it's her first time," is Ricardo's advice. "Make sure you keep something back so she knows it will be worse if she misbehaves again."
"I find a cold bottom most sensitive," Rita finally manages, having taken a bit longer than usual to collect her thoughts, presumably due to her husband's attentions, which are still ongoing, albeit less obvious than before. "If you let her cool down for a couple of hours, she'll be even more responsive when you start again."
To your surprise, Olly then turns to you. With four differing opinions (keep going, take a break, stop altogether or change areas) it seems you might have the casting vote. You're soaking with arousal as you imagine yourself in Claudia's place, which you're sure everyone else can tell, but you have to remind yourself she's not you and you really shouldn't just blurt out how you fantasize about being treated, yourself.
What will you advise?
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The Rulebook
You find a Rulebook that lets you rewrite the rules any organization has to follow
A lucky protagonist stumbles across a magic book that lets them rewrite the rules.
Updated on Jun 10, 2026
by Ggnt
Created on Jul 27, 2017
by ashes2ashes
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