A punishment has to hurt

"Punishments are supposed to be painful, Stephen, I'm sure a vicious bastard like that guard wouldn't think twice about making Rae beg for mercy." She's not wrong, and without meaning to your fingers pinch even harder on her puckered nipple until it turns even darker and harder. Based on Sandra's answer, you explain how once her cleric is chained tightly the guard rips the tunic from her hips and tosses it away leaving her wearing only the tiniest triangle of linen covering her sex.

Sandra's eyes open wide as she bends her knees until almost all her weight is hanging from the chains around her wrists. "Oh, Blessed Saint Cuthbert, please not this!" It is easy to put yourself in the role of the musclebound guard admiring the nearly naked figure of the helpless cleric. Perhaps you look too intent on defiling her because Sandra breaks character for a second to remind you of your earlier words. "You said he couldn't **** her."

"Well, he can't take her virginity, but he can still make her pay for her defiance." You warn her this time pinching both her nipples at the same time, "and there's nothing poor Rae can do to stop him." Based on everything you've discovered about this outwardly conservative sophomore, you're pretty sure that this is what she is hoping for, but if you've gone too far -

"Rae braces herself for the brutality she saw the other prisoners had to go through, Stephen. She's not going to submit easily." Sandra's response confirms your assessment. For just a second as her eyes meet yours you wonder how far she wants you to take this, but then she goes back into game mode. "I'm guessing Rae's early training with the Church of Saint Cuthbert involved exposure to pain and discomfort much like the martyrdom of their holy founder." You hadn't really thought much about what clerical training for initiates might entail, but it is a reasonable assumption although you doubt the new initiates of the church had to endure what you have planned.

The eighteen-inch drafting ruler from your dad makes a perfect tool to whack her breasts and Sandra squirms and whimpers as the heavy maple lands on her breasts again and again. You don't hit her at full strength, but hard enough to turn her breasts red and, more often than not, right on her sensitive nipples. With each smack Sandra cries out, but in spite of the significant pain, she shows no sign of breaking.

"Is it awful?" You ask, pulling away for long enough to open the draw of desk. "Being beaten by that scar-faced henchman, as she squirms helplessly in that dark cell?" Really, what you are asking is if Sandra is OK with what you are doing, and her soft whimper of surrender is all the encouragement you need. "The guard tosses aside his paddle and reaches into his pouch with a grin on his face." You explain as you pull open a large paperclip and slip it onto her puckered teat, "he pulls out small clamps with sharp teeth. Cruel metal devises designed to break the resistance of even the proudest captive." She moans softly but lets you pinch her other abused nipple without a word of protest. Once both paperclips are in place. you spin her around, so her face is pressed against the wall and your thighs grind against her ass.

"There's more than one way to break a proud prisoner." You chuckle coarsely doing your best crude henchman voice. "Especially if she's a pure little virgin like this one is." You move your hand downwards from her breasts between her soft belly and the cool wall towards where her long skirt is tightly belted around her waist. It is just as well that there is this extra level of protection, because if Sandra had been dressed as skimpily as her Lawful Good cleric was, you doubt you could have kept your fingers out of her pussy. Even though your hand is rubbing her through the thick material, you assure her that Rae is not so lucky.

"The guard slides his hand down to Rae's sex like this. Do you think Rae is already slick and ready when his fingers reach her treasure?"

"Yessss," Sandra's moan is low and needy. "Rae is mortified, Stephen, she doesn't know why her body is responding to the guard's brutality, but there's no doubt that she's as excited by this as she was when the bailiff first fingered her." You take this as a license to continue and as your fingers press hard against her sex you continue the erotic narrative.

"Rae's inexperience with men has left her poorly prepared to fight her body's treasonous response." You explain, and when you feel the moist heat radiating from the normally reserved religious young woman as your fingers press even harder into the cleft. "The combination of her nakedness, the pain from the clamps and knowing that there are four other men watching her **** all somehow add to her sexual excitement."

"Yes!" Sandra's needy response could be her playing out the scene, but you are pretty sure it that that is no longer the main factor in the way her body jerks under your groping hands. There is a thick seam in the front of her skirt that you press against what you hope might be her clit; judging by the way she shudders in your arms you feel confident it is.

"The guard wants her to break ... he'll probably turn his attention to Rae's perfect ass next." You press even harder against her pinning her tortured nipples to the wall as your fingers continue their ****. "Do you think she'll lose her last remaining bit of dignity as her backside is paddled in front of the other cheering guards?"

"It hurts ... Rae wants the brute to stop, Stephen." Sandra eyes are closed and she's grinding her teeth, but you can hear her clearly even through her clenched teeth. "But even with the pain and humiliation, she can feel her body responding to his rough hands." To your mind, it's an invitation to continue groping her, but she is so close to cumming that you hate to wait any longer.