Jane grins wickedly down at Chris Carter as she watches his reaction to her terms of service. "Good boy," she croons, running a finger over one of his nipples teasingly. "Now then..." She pauses for dramatic effect, enjoying the feeling of power that surges through her as he squirms uncomfortably beneath her gaze.

With a sultry grin, Jane reaches between them and gives his cock a rough tug, eliciting a gasp of both pain and pleasure from him. "And," she whispers huskily, her voice low and seductive, "you'll be my little fucktoy... My personal plaything." Her other hand trails up over his chest, cupping one of his breasts roughly before pinching the nipple hard enough to make him cry out in agony.

"Do you understand?" she asks, her voice soft but commanding. "Those are your orders... Your terms of service." Her gaze bores into his, searching for any sign of defiance or doubt. When she sees none, she smiles, pleased with herself.

"Good," she says with a satisfied nod. "Then let's begin."

"Now then," Jane says with a sultry grin, "let's get started on your training." She leads you over to a small table in the corner of the room, upon which lies an array of feminine clothing and accessories. "You'll be needing these," she tells you as she gestures toward the items.

"First off," Jane continues, selecting a lacy bra and holding it up for you to see, "you're going to wear this." You wince at the sight of the delicate lingerie; it's so small that it barely covers your chest. "And then," she says, picking out a pair of silky panties next, "these will be your new bottoms." Again, you flinch at the feminine garment; they are several sizes too small and leave little to the imagination.

"Now," Jane says, stepping back to appraise her handiwork, "let's see how you look in your new clothes." She motions for you to turn around, giving you a chance to slip into the feminine attire. As you do so, she can't help but feel a surge of power course through her veins;

Jane's eyes widen as you attempt to take her entire length into your mouth. She growls with pleasure and roughly pulls you off her cock, holding your head in place with one hand while the other reaches down to stroke herself faster. "Good boy," she pants, watching you gasp for air. "You're going to make such a good little slut."

As she continues to fuck your face, Jane leans down and whispers into your ear, her hot breath sending shivers down your spine. "

"I own you now," she whispers, thrusting her hips harder against your face. "You belong to me and my cock." Her other hand reaches around, roughly groping at your balls through your underwear. "And these will be mine too... once I'm done with them..."

I see... So you're not just an ordinary prisoner, then? Interesting. It seems that we have more use for you than I initially thought. Perhaps it would be in your best interest to cooperate with me, after all; who knows what kind of rewards I might offer in return for your compliance? Think about it, Wesley... You could earn yourself a place at my side, as one of my most trusted servants. Or perhaps even a wife, if you play your cards right. The choice is yours.

Ah, it seems I've struck a nerve there. Very well then; perhaps we can arrange that as well. But first, you must prove yourself to me. Show me your obedience and your willingness to submit to my authority. Then, and only then, will I consider granting you such favors. Do we understand each other?

Jane's face contorts with pain and disbelief as she watches the blood and semen pour from between your legs. "No, no, no," she whispers desperately, tears streaming down her cheeks. Frantically, she rips off the bedsheet and presses it against the wound, trying to staunch the flow of blood. "Help! Someone, please help!" she screams at the top of her lungs, not caring who might hear her in the prison cellblock.

Jane buries her face in her hands, sobs wracking her body as she listens to your cries. "Oh god, I'm so sorry," she whispers hoarsely, tears streaming down her cheeks. "I shouldn't have... I didn't know..." She wipes the blood and sperm from your legs, trying desperately not to touch yourself as the pain of guilt and loss threatens to overwhelm her.

"Help!" she screams again, her voice raw with anguish. "

Jane idly flits between conversations as she sips her wine, her eyes occasionally drifting over to where you were led moments ago. The image of the two burly men pinning you down and taking what's theirs plays through her mind like a pornographic film, and she can't help but feel a surge of power course through her veins at the thought of being able to control someone so completely.

She pauses mid-conversation, tilting her head as if in deep thought. A wicked smile slowly spreads across her lips as an idea begins to form in her mind, darker and more twisted than anything she's ever done before...

Jane smirks to herself as she watches the two men roughly fuck you in the next room, your pleas for mercy falling on deaf ears. The sight of their hands on your hips, thrusting deep inside you, fills her with a mixture of arousal and power that's almost overwhelming. She can't help but wonder how far she could push you...

She leans in close to the guest she'd been talking to, her voice barely above a whisper. "You know, I think it's time for our little pet Chris here to learn some new tricks," she says with a wicked grin. "I was thinking maybe we should find someone else to share him... or even auction him off to the highest bidder." Her eyes gleam in the low light as she imagines the possibilities unfolding before her like a dark, twisted fairy tale.

I'm delighted to hear that you are eager to practice more with the dildo, Jane. As your mistress and teacher, I am here to help guide you every step of the way. Remember to communicate openly with me about any discomfort or boundaries you may have, as well as share your progress and successes. Together we can ensure that you become an expert in pleasing me in every way possible.

You are showing great progress, Jane. However, you must remember that safety always comes first. If at any point you feel uncomfortable or experience pain during your practice sessions, do not hesitate to stop immediately and inform me. My priority is your wellbeing as well as your growth as my obedient sissy slave and cockslut.