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Chapter 50
by
Obedient Lorelei
What will you advise?
It never hurts to agree with the boss
"I find anticipation is sometimes almost as bad as the spanking itself. Serving some corner time lets me really dwell on what's coming up and how much it's going to hurt and how I can't do anything to avoid it. I also get the chance to think about my behaviour and what I can do to be better and not earn any more punishments, although that last part never seems to work! I think Claudia might benefit from a bit of self-reflection before you finish spanking her."
Olly is nodding while you speak, taking on board everything you're saying.
"Thanks for that, Jenna. Thank-you, everyone, for the advice. Did you hear that, Clau?" The wan blonde is still sobbing hysterically, too distraught to answer intelligibly, but he continues anyway. "After we get back to halls, I'm going to make you stand outside the door naked with your nose to the wall so anybody passing by sees what a naughty girl you've been. Then, when you've had a good chance to think about your behaviour and your bottom's cooled down, I'll take you over my knee again and spank the living daylights out of you, understand?"
Claudia still doesn't speak, but from the increasingly animated wailing, it seems she's aware of what she has in store. Maybe if she changes her mind or gets too frightened, she'll just run away when he leaves her outside.
"But before that," he adds, "I'm going to fuck your tight little arse until it feel like I'm going to split it in two. Jenna, would you mind passing me the lube?"
You quickly oblige, picking up the jar where Rita left it on the table and handing it over to the young man. It appears the other jar, containing the soothing cream, won't be needed until later, if he decides she deserves it at all.
Olly uses his middle finger to take a large glob of the viscous slime, more a grease than an oil, then tries to push it into her puckered rosebud. As you found earlier, she's tight enough to make this difficult and so after a while, he tells her to bend over the table and spread her cheeks. She's still too weak to get up unaided, so he helps her and she cries out in fresh pain as she pulls her buttocks apart, exposing her cleft degradingly, much to the delight of most of her audience.
Now, her boyfriend is able to prize her sensitive sphincter open with one hand and insert the lubricant with the other, using two fingers to spread it around evenly and do a little to prepare her for his penetration later. Finally satisfied, he stands back and puts his hands on his belt buckle, as though he's contemplating dropping his trousers and rutting her right there in front of you!
Does he do that?
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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
You can customize this story. Simply enter the following details about the main characters.
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