A flogging

Author's note: Credit for this whipping scene goes to pornia. I changed the setting from the overlord's dungeons to the **** ship, but other than that the descriptions are pretty much all his.

“The captain orders you to be hung by your wrists from the main mast so you have to stand on the balls of your feet. In this position your breasts are lifted and they jiggle with every attempt you make to move.” You do your very best to keep your neutral DM tone as you explain what is going to happen and then pause for a second to watch Sandra's reaction. She just listens her eyes wide with excitement, so you continue. “He grabs you by your hair and forces your head back so you can see him out of the corner of your eye. 'Are you saying you're not guilty?!' He growls.” You stop and look at top-heavy sophomore whose breathing has become a bit erratic.

Sandra's eyes dart away, avoiding contact, but when she realizes you're waiting she meekly answers, “No.” Looking at the floor in a defeated manner she mumbles, “I'm guilty. I deserve this.”

With that answer, you now resolve to play this through to the end, no matter how much Rae the character might object in-game. “The captain directs the boatswain to give you a dozen lashes with the flogger. The burly man strides around to your front swinging the flogger with practiced ease.” You confidently return to full DM mode.

“The brute of a man in a coarse vest made of sailcloth carefully looks over your sweat-covered naked body. He uses the handle of the flogger to brush your hair off your shoulders so your tits are completely exposed before chuckling wickedly. 'A tit-whipping always breaks them, capt'n.' He traces the braided leather tails of the flogger against your breasts with a lewd smile. 'And the bigger the tits, the greater the pain.' He adds. 'Cunt, this is a lesson, you ain't never going to forget.' With that he shakes out the flogger with a flourish and steps back to the ideal whipping range right in front of your exposed breasts.” You pause the narration and point to her dice as you explain. “The flogger is designed to inflict pain without damaging the skin, because the target is your breasts, you'll need to roll over a seven to stay in control of your response.”

“A seven?” Sandra hesitantly asks, “this is going to be bad isn't it?”

“The ship's captain isn't bluffing.” You answer as a devious idea comes in your mind. “Stand up.” You order.

“What?” Sandra gives a perplexed sheepish look.

“I said stand up. I want you to sit in that chair.”

“But, I don't . . .” When the top heavy priestess sees your uncompromising demanding look she averts her eyes and stands. Putting her folding medal chair aside she walks over to the other end of the table where Brian usually sits. The old Adirondack spindle-back chair has no arms and is made of rough, unfinished wood. The top of the front legs rises up about an 1/2 inch above the seat, effectively making two knobs on the front corners of the chair, the place where Sandra has been grinding herself down against.

Her head whips around looking at with terrified knowing eyes.

“The whip-master did say 'you're never going to forget' this punishment.”

Sandra responds by shaking her head in a negative fashion too afraid to speak. “Bring the chair over and sit down.” You will have none of her ****. “There is no way Rae can escape her punishment.”

The condemned cleric looks back down at the chair and shudders while picking it up and moves it to her place at your right hand. Before Sandra can sit down, however, you twist the chair forty-five degrees so the that the right front corner is facing the table. The busty sophomore slowly sits down, spreading her legs in order to straddle the seat right before the knob.

“Please, have mercy.” Sandra again pleads with you.

“Rae's begging is met with dismissive chuckles.” You use her statement in game against her. “Cruel cries for justice are shouted out from the jeering sailors: 'Shut up whore, you're getting what you deserve!' 'Lash the bitch harder!' 'Make the cow's udder bounce!' 'Teach the cunt a lesson!' 'Let's hear her scream!' 'Whip her!' Several begin to simply chant, 'Whip her tits!' “Whip her tits!' Whip her tits!'”

“The boatswain reaches back with his powerful arm and lets the leather fly. It viciously hisses through the air and the leather tails slash diagonally across the upper part of your right breast down across the lower inside of your left tit. Roll your d20.”

Sandra runs her fingers through her hair with one hand as she rolls her pink dice with the other.

“Even with a successful roll of a 10 you still scream out, because being whipped in this part of your body is far more painful than anything you can imagine. Roll again.”

“Nooo.” Sandra whimpers as her dice stops on a 5. Her hand instinctively covers her breasts pressing against the small tent formed by her hardening nipple.

“This time the whip lands horizontally,” you waste no time in explaining her failure, “across the peaks of your breasts and cuts into your left nipple. Your howls of agony are greeted with claps of approval. Remove a Hit Point from your character sheet.” You order.

“Oh fuck that's hard.” The top heavy brunette gives a guttural gasps as she raises up in her chair and then lowers herself on the wooden knob. Thrusting her hips down, as her doom requires, Sandra's body shakes as she fumbles about with her pencil trying to make the notation.

After much effort the tortured priestess sits back in her chair and rolls a 4, another failure.

“No, no, no.” She shakes her head in disbelief. “Not again, not so soon!”

“Once more, the whip strikes horizontal, across the center of your tits, slashing into both of your nipples.” Though you cannot help but notice Sandra body is still quivering, you continue without a break, “The hatch to the lower decks has been left open so the other slaves can hear your screams. Lose another Hit Point.”

“But this brings me down to one.” Sandra squirms about in her chair as she complains.

“That's not my problem.” You flatly answer. “Now get going.”

Biting hard down on her lower lip Sandra slides forward, pushing her sex onto the knob.

“Damn it!” She swears as a long groan is **** through her clenched teeth. “Rae's body is responding to the sensation of the whip on her breasts, she doesn't want to but she is getting aroused.” She grieves, not being able to control her tongue, let along her body, as she jerks up and down a few times, humping the chair.

“The boatswain notices the change in your response and he uses the rounded knob on the handle of the whip to separate your legs even more.” You strangely feel compelled to stay in character. "the ****-ship's crew bursts into laughter at your disgrace and mockery descends on you from all corners. 'It's true, look how swollen her pussy is!' 'You can see her juices coming down the inside of her legs!' 'What a whore!'”

Gasping, Sandra collapses forward, her elbows thud onto the table, as her face falls into her hands. While her hips still grind away she makes a crude scratch mark on her character sheet and forces herself to sit back up with much effort.

Breathing heavy, her chest rhythmically heaving up and down, she takes her dice and rolls again: A one, a fumble.

“Oh no!” Sandra moans softly, clearly having trouble concentrating. “What's it mean?”

“Rae's body betrays her.” Her moan tells you that this is exactly what she thought it meant. “After those last two nights at the hands of the night-guard your resistance is already weakened and the pain of the flogger on your most sensitive area is too much for you to take.” In spite of your better judgement, you find you cannot stop. “Somehow, the boatswain senses how close you are, and once again he uses the knob of the handle to press against your sex. This time when you cry out, the screams are unmistakably cries of pleasure.”

“Yes, Stephen, I hate it and try to hold back but I can't...” she pauses no longer even pretending to disguise the way her sex is grinding against the knob of the chair, “... I can't ... Ooohh Fuckkk!!!”

The way her body jerks against the chair leaves no doubt that she is in the midst of a truly spectacular orgasm. With this cathartic climax, you realize with a start that you have gone way too far.