By throwing him in the deep end

"That first time I had you in here, I think I overwhelmed that poor little brain of yours with pleasure and now your body can't help but seek it out." She continued to talk down to him as he heard her moving around once again.

"Your failings are not purely your own, Cassidy. They also weigh heavily on me, after all you belong to me now and to guide you. So any time you stray, it is a failing on my part too."

Finishing up whatever she was doing at the cabinet, she moves behind him once again, one hand gripping at one of his plump cheeks and holding it open so that her saliva slicked hand can press insistently at his puckering rosebud. He groans into the gag as her fingers tease at his sensitive ass, he had felt so empty inside ever since she pulled the toy out, not used to the feeling of having nothing in there after being plugged up for so long. After softly stroking with her fingers, they retreat and then come back grasping a small hard object, pressing it forcefully against his hole, he can't fully tell what it is but it is much smaller than the plug he had just been filled up with.

"Another saying that I'm fond of is, 'an ounce of prevention is worth a pound of cure'"

With the last word, his ass opens up and accepts the small thing inside of him, as well as two of her relentless fingers, another lance of sheer pleasure shoots down his throbbing cock at the sensation of his ass being filled up. Her fingers are persistent and drive on deeper, his hole eagerly letting them in, having been thoroughly stretched out by the plug. He struggled to figure out what she was pushing inside of him, his mind far too focused on the pleasurable sensations of his stimulated tunnel to worry too long about that. All too soon her fingers slipped back out, leaving a hard lump pressing lightly against his prostate in their wake.

"You shouldn't worry your little head too much about what it means, just know that I will take you firmly in my hands and guide you."

Cassidy's knees buckle and his legs give out as his mind goes blank, searing white hot pleasure overwhelming his body as the object Jana had pushed inside of him begins to violently vibrate, rubbing up furiously against his prostate. Almost as soon as the vibrations have begun, they stop, though it takes him far longer to recover from the effects, his breath coming hard and fast around the ball plugging up his mouth.

"Ohhh, I think you liked that didn't you?" Jana says as she reaches down with a hand to tease away at one of his achingly erect nipples, pinching the sensitive teat between two fingers and eliciting a muffled moan in response.

"Well, lucky for you, there's more where that came from, much much more." He could hear her chuckling to herself but paid it no heed as the toy in his ass vibrated again, this time mirrored by a toy pressing up against the delicate nipple held by her hands. The dual sensation was heady and intense, his hips bucking at the motion trying to get any amount of relief but completely unable to. She quickly secured the toy in place pressing insistently up against his nipple, her fingers moving deftly to strap it down before moving and doing the same to the other nipple.

She torments him like this for a little bit, activating the toy long enough to make him squirm but not nearly long enough for him to find any satisfaction. Her hands reaching down occasionally to stroke his hair, or rub lovingly along his back, each touch unexpected and sending shivers down his spine. He tries desperately to beg for release but is unable to make anything except muffled groans around the ball in his mouth, his frantic sounds only met by another despairingly blissful vibration.

"Now this, I think you're really going to love." She punctuates this by wrapping his little prick up in her lithe fingers, thumb and forefinger forming a small ring and rubbing smoothly up and down while her other hand fondles gently at his dainty balls. Her hands tease at him like this for a little bit before he feels one of the toys pressed up against the poor swollen head of his cock, it is quickly joined by another and wrapped up to hold them in place. Each of the toys is squeezed forcefully up against the tip of his meager cock, and he knows if she were to set them off now that it would be far too much for him to bear.

He moans pleadingly for mercy which quickly turn to muted wails of pleasure when Jana activates the toy once again, the tip of his cock, his nipples and his ass, all his most sensitive spots are assaulted with bliss, the vibration of the toys taking away his breath and flooding his mind with delight. They stop all too soon and he's left stupefied for some time, his brain taking several long seconds to recover from the mind-blowing ****.

"Well, Cassidy, I have a meeting I really must get to, I am a very busy woman after all." Jana says, laughing haughtily at the joyful misery she is leaving her toy in. "I trust that you'll do fine in my absence, don't have too much fun now."