One step further

You dismiss the idea of whipping Sandra immediately. Even though her sketches all had strong masochism themes to them, you decide to go with the sexuality aspect of the poses.

"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. Sandra is now dressed as skimpily as her Lawful Good cleric in the Overlord's dungeon, and it is all you can do to keep your fingers from slipping under the thin elastic of her last remaining defense. Even though your hand is rubbing her through the sheer layer of her panties, you assure her that Rae is not so lucky.

"The guard's fingers find the passage between Rae's sex and push roughly up into her." Her underwear prevents you from actually doing this, but you press your fingers hard creating a crease that penetrates just enough to give her the sensation of what Rae is feeling. "Unlike the bailiff's careful examination, this man is using his fingers to punish her for her resistance."

Sandra's eyes open wide as she bends her knees until almost all her weight is hanging from the chains around her wrists and her sex jerks against your hand. "Oh, Holy Father, 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. The chains above her head rattle as Sandra moans softly. "He's going to ruin her?"

"Well, he can't risk rupturing her hymen, but he can still make her pay for her defiance." You warn her as you push her even harder against the wall so her breasts bulge out like water balloons, "and there's nothing poor Rae can do to stop him." Based on the graphic pictures in her notebook and the way Sandra has responded to the ERP'ing so far, you're pretty sure that this is what the repressed conservative Jewish coed is hoping for. Of course, if you've gone too far there will be Hell to pay -

"Rae thought she was ready for the brutality she saw the other prisoners had to go through, Stephen." Sandra's response confirms you're on the right track. She twists her head back until 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. "But I don't think, she is ready for the feeling of sexual arousal. Until she was brought before the Ballif earlier, she'd never ever been touched by a man - not like this."

"Is it awful?" You ask, stepping back to open the draw of desk. "Being groped 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 as she presses her forehead against the wall, is all the encouragement you need to turn this up another notch.

"The guard puts clamps on Rae's nipples." You explain as you pull open a large paperclip and slip it onto her puckered teat, "cruel metal devices designed to break the resistance of even the proudest captive." She moans softly but lets you pinch her other nipple without a word of protest. Once both paperclips are in place. you spin her around, so her face is once again pressed against the wall and your thighs grind against her ass.

"When the guard slides his hand down to Rae's sex like this." You ask as you cup her sex again, "do you think Rae is already slick and ready for his fingers?"

"Yessss," Sandra's moan is low and needy. "Rae is mortified, Stephen, she doesn't know why her body is responding to the man'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. 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 ..." You press even harder against her, pinning her tortured nipples to the wall as your fingers continue their ****. "Do you think your Lawful Good priestess will surrender her last remaining bit of dignity as she is groped in front of the other cheering guards?"

"Rae is trying to fight this, Stephen," the stressed tone of Sandra's response indicates that she too is fighting the unfamiliar sensation, "but she can feel her body responding. The combination of pain and pleasure together with knowing that there are the other guards waiting their turn .... it's too much ... ." Sandra eyes are closed and she's grinding her teeth, but you can hear her clearly even through her clenched teeth. "Even though she's humiliated, perhaps because of it, she can feel the heat in her core building ... oh Saint Cuthbert, not that ... Oh please not that!"