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Chapter 52
by
Obedient Lorelei
Why has he chosen this position?
To distract you
"Look Rita in the eyes while I paddle you, Jenna," Ricardo says, handing his wife a realistic vibrating dildo. Your jerk your head up, blushing at the realization you've been caught inspecting your boss's pudenda at close range. Without breaking eye contact, she grabs a couple of pillows from behind her and uses them to prop herself up so that she can lie back in a semi-sitting position and fuck herself with the dildo, whilst still watching you. The buzzing and sounds of rapid penetration just a few inches beneath your face are distracting, but you can cope—for now.
"No screaming or swearing, please Jenna," he continues, preparing to begin the punishment. You're confident you can manage to moderate your language, but if the implement hurts as much as you suspect it will, screaming may be out of your control.
You're about to ask him politely to commence when he smacks the board sharply against your glowing cheeks at what feels like a slightly upward angle. The swat is even harder than the four Rita gave you in her office this evening and makes you gasp and groan. You arch your back and brace yourself against the foot of the bed to keep from falling over, but thankfully manage to avoid earning any extras this soon into proceedings.
As soon as your breathing returns to normal, he hits you again, sending pain blazing through your posterior and threatening to bring tears to your eyes. It's not far off how the mail room paddle felt, even though that was much heavier.
The third swat makes you grunt and by the fourth, you're no longer able to fully calm down in between, although he waits more than ten seconds before number five. Your eyes become heavy with unshed tears on the next and you're breathing heavily, but your nipples are hard and your sex is dripping. You may regret the extra bruising when you're getting your next morning spanking, but right now, Ricardo's dominance is satisfying you in ways you've not felt for too long.
After the first six, he pauses and gives you a chance to recover—a consideration he did not show Claudia, you recall, although she was getting only a dozen in total, so that might be the reason. Rita doesn't stop, however, continuing to fill herself with vibrating pleasure through the break. After a moment, Ricardo continues, at a slightly quicker pace.
You can't help moaning a little through the next half a dozen and towards the end, the first tear runs down your cheek. Your bottom is absolutely on fire and already hurts more than after any spanking you've received since finding the Rulebook, with thirty more still to go.
Another short break lets you study Rita more closely. She's flushed and breathing almost as heavily as you and although you keep your eyes on her face, you're aware that she's masturbating more vigorously. You're not sure which of you is enjoying this more right now, though you have little doubt that by the end, she will have had the lion's share of the pleasure!
The paddle is just about large enough to cover both cheeks with each swat, so there's not much variation between smacks, the pain building to a relentless crescendo that has you starting to sob by about the fifteenth. Two swats later, Rita climaxes powerfully and she's still twitching when you get your third break.
"Enjoying yourself, darling?"
"Yes, thank-you, my love."
Ricardo walks round the bed to kiss his wife while you gasp for breath and try to stifle your sobs. Just twenty four more to go. You can manage it, although you could really do with rubbing your bottom for a bit.
"Is there anything we can do for you?" Rita asks her husband, when they break the kiss. "You know Jenna's ready for you, however you want her."
"Maybe I want you, instead." They kiss again and you wonder whether you can get away with cupping your throbbing cheeks for a moment without disappointing either of them.
"You can have me whenever you want me. Jenna's there for the taking. I know you're attracted to her. Who wouldn't be? She's young, sexy, so submissive and that bottom!"
"I don't need anybody except you."
You decide to risk it and reach back to soothe your aching buttocks. They're hot to the touch and you groan as you gently comfort them. It might be nice to stroke somewhere else, as well, but decide that would be going a little too far.
"I want you to enjoy her. I won't be jealous, really. Envious, maybe, but never jealous. I know you love me. I love you and I want you to have this pleasure from my friend."
"Alright, but on one condition."
What is his condition?
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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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