A young boy needs a guiding hand

"Yes, Please guide me." Cassidy whimpers out, each word punctuated by a pathetic sniffle as Cass works to stop crying.

"That's a good boy, Cassidy." Jana responds, her hand still working to soothe his aching sore ass. "That's enough for one day, I'm sorry that I had to do that. Seeing that video upset me Cassidy, you don't want to upset me do you?"

"No... I-I'm sorry" Cass sputtered out, trying and failing to entirely suppress his ongoing tears.

"That just won't do Cassidy, from now on you will call me Jana or Mistress while we're alone together." Her hand possessively gripped his cheek, eliciting a small cry. "Can you do that for me, Cassidy?"

"Y-yes, Mistress."

"That's a good boy Cassidy, my guidance won't all be punishments, I will reward you when you do well." Jana goes and opens a drawer in her desk, rummaging around briefly before returning to her spot behind him. Her hand returns to his ass again but this time bringing with it a soothing coolness that elicits a soft moan in response.

"Doesn't that feel nice Cassidy? See how good it can feel to be rewarded." Jana purrs down at him, continuing to spread blissfully comforting cream over the welts on his butt. Cass murmurs in quiet gratification as Jana mercifully rubs cream into his glowing ass, calming the angry red skin there. Jana continues her kind treatment of his poor bottom, the aching there being reduced from a burning agony to a soft throb. Her other hand kindly but firmly maneuvered his legs, pulling off his shoes and his shorts that had gotten tangled up around his ankles, stripping him apart from the crop top covering his chest.

Cass gasps as he feels Jana's finger tease down between his cheeks to the rosebud there. Her finger softly teases at his clenched hole, moving to spread the soothing cream all around it before returning her to his back passage and begins applying pressure insistently. Cass groans out in pleasure as he feels her finger enter him, eased in by the cream she slowly works her way deeper, her digit gently spreading him out. Once her finger is all the way in she curls it upward pressing blissfully into his prostate, Cass whines in response, his cock hardening at the tingling sensation.

"What a good boy, you're taking my finger so well." Jana praises him, a blush spreading over Cass's face at the flattery. Jana begins working her finger in and out of his grasping hole, whispering down pleasing platitudes into his ear as she does so. Cass feels his body heating up as she keeps applying pressure to his prostate. She pulls her finger out, eliciting a soft whimper at the exit which quickly builds as she presses two back up against his sphincter. It doesn't take much pressure for them to slip in, sinking deeper to hunt out Cass's special spot. His cock quivers with each repetition, Jana steadily building up the pace.

"Are you going to cum for your Mistress?" Jana murmurs sensually in his ear, Cass tries to respond but finds his mouth dry and his mind no longer capable of forming words. The white hot rapture building in intensity as Jana speeds up her **** on his prostate, her fingers making lewd squelches as they plunge in and out of his asshole. Cass's orgasm hits him hard, his entire body shaking, his cock is throbbing beneath him spurting out thin ropes of cum with each wave that rocks over him. His mind goes blank, only able to focus on the intense feelings of his body as Jana milks him dry.

Eventually his orgasm comes to an end, his body collapsing down supported only by Jana's strong hands. She leisurely eases her fingers back out from his asshole, making sure to stimulate his prostate one last time, which sends a shock of pleasure through his body that drives the air from his lungs.

"What a good boy, I'm so proud of you." Jana whispers into his ear. "Wasn't that pleasurable?"

"Mmmmm" Cassidy nods his head mumbling, still struggling to form words with the aftershocks from his orgasm still flowing through him.

"Now, you don't want to be the only one feeling good. Don't you want to pleasure your Mistress?"