Dan's Conditioning Ch. 03

Dan followed Miss Kendra out of the store with his eyes pinned toward the ground. He sighed as he limped and staggered across the parking lot toward Kendra's car. Popping open the door, Dan awkwardly eased himself inside, letting out a long deep breath and a mumbled groan as his swollen and raw ass contacted the leather seat. "She got a little rough with you today, huh Danny?" Kendra asked.

"Yea, just a little bit Ma'am," Dan mumbled sarcastically.

"Well, I am sure you learned a valuable lesson then." Remaining silent, dan simply nodded his head in agreement.

Before long, they arrived at Dan's house. The car pulled into the driveway, and it's engine revved up a bit as she shifted into neutral and applied the parking brake. Dan quickly popped open his door and began limping away toward his house. About halfway there, He heard the other car door slam shut. He slowly spun to see Miss Kendra staring back at him over the roof of her car. Dan's eyes rolled, and he tilted his head back, staring up into the late-night sky.

"What's wrong, Hun? I can't leave without tucking in my Babe," she teased. Dan's head fell back down to see Miss Kendra playing on her phone while leaning over the hood of her car. Her skirt rode up, allowing him to admire her garter belt. Flipping her hair, she shot a subtle smirk toward dan.

He stared up again at the sky as he smiled and shook his head. Kendra quickly strutted up beside him, grabbed his hand, and wrapped it over her shoulder. "Come on, Hun lets go inside," she purred. As they walked toward the house, Kendra slipped her hand down into Dan's back pocket, giving his ass a gentle pinch.

When they reached the front door, Kendra positioned herself behind dan and rested her hands on his shoulders, massaging them. While he did manage to get the key into the lock, he remained frozen, unable to keep his eyelids open as he rolled his head around. After allowing Dan a few moments of comforting bliss, Kendra rested her chin on his shoulder and began to nibble at his ear. His body fell limp.

Her hands slid down from his shoulders, wrapping one arm across his chest, she seductively caressed him. The other hand slid down his side and around his hip, onto his now swelling bulge, where it remained, gently massaging Dan's swollen cock. "Come on, Hun, let's go inside, and find out how big of a load you have worked up, thinking about me all day," she whispered into his ear. Then She gave his bulge a playful tap. Dan's eyes popped open, and his head shuttered as he finally finished unlocking the door. They both continued inside the house through the hallway to the base of the stairs.

Miss Kendra rushed in front of Dan and promptly sat on the stairs facing him. Leaning back with her elbows resting on the stairs, she stretched out one leg and rested her foot on Dan's shoulder, subtly applying pressure with the point of her stiletto heel just below his collarbone. "Down my pet," Miss Kendra commanded. Dan instantly dropped to his knees as the command rang out in his head. "I guess you have learned something today then," Kendra joked, letting out a little chuckle.

Kendra rested her feet over Dan's shoulders and used them to flip off her heels. She then pressed the ball of her foot just below Dan's chin, rubbing her toes inside her satin pantyhose over his lips. "Now, my pet stays on all fours, right Danny boy?" Kedra purred. Dan slowly nodded his head in agreement with toes still pressed to his lips. "Good boy," she reassured him.

Spinning herself around on the stairs, Miss Kendra lingered, bent over for a few moments with her ass inches from Dan's face, before standing upright. Seductively cocking her hips with each step, she strutted up the stairs. "Here boy," Kendra playfully commanded, and dan crawled, remaining on all fours up the stairs behind her. He continued to crawl, following her as she sauntered down the hallway and through his bedroom door.

Once inside, Kendra sat down on the edge of the bed with her legs crossed. Dan crawled in front of her, remaining on all fours as he gazed up into her eyes. Snatching Dan's chin, Kendra lured him upward into a kneeling position before grasping the bottom of his shirt and drawing it up over his head, tossing it to the side. "Up, my pet," she commanded. Dan obeyed, Standing upright directly in front of her. She ran her fingers around inside the waistband of his jeans before undoing the button and dragging them down to his ankles. his cock was rock hard and straining the hot pink panties which Kendra had ordered him to wear earlier that day. she licked her lips as she stared straight ahead at his cock. "You can try to pretend, But that cock of yours doesn't lie, Danny. Your loving every minute of this." Kendra purred. Dan remained frozen.

"Now, where are those clothes you picked out for me today?" Kendra asked.

"Oh shit, I left them in the car."

"well, I think you better go get them."

"yes, Ma'am."

Dan reached down to pull up his pants, but Kendra quickly stepped on them. "Did I say to put your pants back on?" Kendra questioned

"Uh, no, Ma'am," he stuttered.

"Well, what are you waiting for? I want to see what you picked out."

Dan didn't reply. He simply stepped out of his pants and walked down the stairs to the front door, pausing for a moment as he grabbed the handle. His heart began to pound uncontrollably, and his breath became heavy. His head rolled around on his shoulders. Letting out a long heavy breath, before A soft "Fuck it" escaped his lips.

He yanked open the door and darted outside, down the walkway toward the car. When he was only about ten feet from the car, it let out one loud honk and two flashes of light. Frantically grabbing the door handle trying to yank it open, dan realized it was locked. In a panic, he dashed to the driver's side door and found the same dilemma. Abandoning his mission, Dan ran back into the house, slamming the door behind him. He staggered back up to his room, where Kendra was waiting. " It's locked," he gasped between panting breaths.

"Oops, shit, my bad," she giggled before picking up her keys lying on the bed and clicking the unlock button. Dan could hear two honks come from the car and saw the headlights flash through the window as he tried to catch his breath. "well, I'm waiting, hun," taunted Kendra.

Dan grabbed his hips, letting out a few more deep breaths before staggering back downstairs to the front door. Once there, he paced in a circle a few times before finally yanking the door open again and running toward the car. This time the door opened with no difficulty. But as he looked for the bag, it wasn't to be found. He ruffled through the car quite a bit before bending over to check under the seat, leaving his ass outside and exposed in a pretty little hot pink thong. As he dove in deeper to inspect under the driver's seat, the car alarm triggered, letting out deafening honks from the horn and bright flashing lights.

Dan's head quickly bounced up. Watching in the rear-view mirror, he noticed lights illuminating in the windows of the house across the street. He promptly threw his whole body into the car and slammed the door behind him. Curling himself up behind the passenger seat, Dan peered over the headrest at the house across the street as the car alarm rang out. After a few moments, the alarm ended. And Dan remained quiet and hidden in the car, still staring across the street at the now illuminated house. With his heart pounding, he watched a silhouette as it opened the curtains and peered out of the window towards the car. It swapped between windows, and Dan could feal its investigation overlay the car. After what seemed like an eternity, the silhouette appeared to depart, and the lights in the house began to turn off one after another until it was finally cold and dark again.

Dan's search for the bag continued but to no avail. When he finally abandoned the mission, he stepped out of the car slowly. He gently closed the door before hastily tiptoeing back up the walkway and into the house. As dan walked through the bedroom door, Kendra immediately asked, "Where's the bag, hun?"

Dan twisted his foot and stared down at the floor as he murmured, "It's not in the car. I guess I must have left it at the store. I'm sorry, Ma'am, I really thought I took it with me."

"Oh, crap. You know what, I forgot. I grabbed the bag and put it in my purse when you rushed out of the car." Miss Kendra revealed as she pulled the bag from her purse and laid the outfit out on the bed

"Oh, wow, that's fucking hot! You really know me," she reassured him, sitting on the edge of the bed with her knees held tightly together.

"Now come here," Kendra commanded, snapping her fingers, and pointing at the ground directly beside her. Without hesitation, dan quickly strutted over and stood exactly where she had indicated. reaching up, her hand grabbed the back of Dan's neck. "Down," she commanded, pushing him downward, forcing him to bend over her knees. Dan's body began to shake and shiver. He wasn't sure if his ass could take any more spanking after what Miss Natasha had already delved out earlier that day.

Kendra examined his battered and bruised ass. "Oh wow, she did go hard on you. Is that a fucking bite mark on your ass?" Dan quickly shook his head, yes. Kendra reached into her purse and pulled out some medicated lotion, then began to rub it on Dan's swollen ass cheeks, helping relieve some of the soreness.

"She went a little too hard on you today. I'm going to have a talk with her," Miss Kendra comforted.

Dan's head perked up, and he shook his head again In agreement. "Discipline is one thing, but she can't be roughing up my new pet like this."

Miss Kendra dug through her purse again. This time she pulled out a bottle of lube and squirted some into her hand. Pulling Dan's thong to one side, she Used her wet hand to apply lube to Dan's ass, sliding her fingers up and down between his cheeks. Her middle finger pressed firmly against his hole with each swipe.

"Now Danny, I want to talk about your training. We both know your obligation to follow along or deal with the consequences. But, I think you're going to need some positive reinforcement as well," Kendra professed, as she slid her middle finger, knuckle deep, into Dan's hole. A long, grumbled moan escaped his lips. Curling her finger inside him and with firm pressure, She began to massage his prostate. Louder moans and panting breaths rolled out of him as the sensation of silky pantyhose against his throbbing cock seemed to instinctually provoke him to hump Kendra's thighs as if he were a horny puppy

"Oh my god, what a little slut you are... you needed that, so fucking bad, didn't you?" chuckled Kendra

"yes, thank you so much, Ma'am," Dan gasped.

"Now there's a polite little slut. I See, you've learned something from your time with Natasha today." Kendra cackled before adding her ring finger into Dan's hole, stretching it just a bit fuller. Another breathy moan came from Dan's mouth. he pushed his ass back, grinding it against her hand forcing her fingers deeper inside him. "And, so fucking eager, you are too. I can tell I'm going to have a lot of fun training you." Kendra purred before continuing, "Now I know you understand the consequences of disobeying me, but I need to give you something to strive for as well. I need you to not only be petrified of being disciplined, but you also need to be eager to please me.

"So I have a little idea to help motivate you. When I'm done training you and you have completed all my tasks, to my satisfaction. I'm going to get all dressed up to the nines, In That outfit you picked out for me today, And I'm going to let you actually fuck me.

"I will give myself to you completely, the way you are giving yourself to me now. Nothing will be off-limits. You can fuck my pussy, my ass, my mouth, hell I'll let you fuck my belly button if that's what you're into," Miss Kendra chuckled.

Dan continued humping away, furiously massaging his cock against Kendra's pantyhose. "I thought you would like that," she purred. A slight whimper of pain came from dan as she slipped her pointer and pinky finger into his hole, stretching it even further.

"Now, I've got some tasks for you to complete tonight. Each one will help you get closer to the reward at the end of this rabbit hole. So, what do you say, Danny? are you up for it?" Dan nodded enthusiastically, yes.

Booming moans between gasping breaths for air came from Dan. Kendra was vigorously finger fucking his ass hard and fast now. Loud, sloppy wet clapping sounds reverberated through the room with each thrust. "Good boy," she reassured him, giving one last forceful thrust against his prostate before slowly withdrawing her fingers from his hole. With a whimper and pouted face, Dan let out a long sigh. Miss Kendra reached in her purse to obtained a ring gag. "Open wide, my eager little slut," she purred. Prying Dan's mouth open, she inserted the ring and secured its leather straps tight around his head. With his jaw strained and wedged open, saliva leaked from his bottom lip, running down and dripping off his chin. Kendra gave Dan's ass a gentle, playful little slap.

"Now up slut!"

Dan quickly sprung up, turning to face Miss Kendra, still sitting on the bed. His cock was at full mast, pitching a strained tent in his panties. With her face just inches away, she gave a harsh flick to the tip of his cock, causing him to wince as she let out a sharp giggle. Leaning back on the bed, Kendra seductively slid her hands down her sides, along her hips, and up under her skirt. Her hands gradually slid back down along her hips, bringing with them her panties. Stopping at her knees, she released her panties, allowing them to fall to her ankles. Dan's face lit up like a Christmas tree.

"Don't get too excited, Danny boy. You don't get to fuck me yet. Now lose your panties," she barked. He instantly obeyed. Leaning back again, Kendra spread her legs wide and massaged her thighs while staring up into Dan's eyes. He tried desperately to get a glimpse up her skirt but couldn't achieve the proper line of sight.

"Ok now, listen up, Danny boy. I want you to do a handstand right here between my legs." Dan's eyes revealed his obvious confusion as he remained still pondering whether the command was genuine.

"Come on, Danny, I'm waiting." Kendra taunted, tapping her fingers on the bed. With a shrug of his shoulders first, Dan put his head down at the edge of the bed and flipped himself up into a handstand. His back was against the bed and his ass in the air facing Kendra. She viciously kicked Dan's hands out, causing him to collapse against the bed with his neck and shoulders pinned to the floor. Without hesitation, she swiftly forced his ankles down toward his head and wrapped her legs around his. While Pinned in this pretzel-like pose against the bed with his ass in the air and legs over his head, Kendra pulled her ankles back toward Dan's head. The panties still around her ankles stretched across his face. The scent of her wafted through his nose as he felt the warm moisture of her panties against him. It was intoxicating.

"Pretty vulnerable spot I got you in, huh Danny," Kendra taunted. She dragged her fingernails over his ass hole then up his taint until she reached his sack, which she gave a gentle but firm tug, digging her nails in slightly. Dan's body trembled under her. "I love how I can make your whole body quiver with just a few fingers. You're just so simple; You couldn't even possibly imagine the depraved expectations I have for you."

She grabbed the bottle of lube and briskly jammed its top into Dan's hole, then violently squeezed it, squirting a thick heavy stream into his ass, emptying most of the container. Unable to contain the massive amount of lube, his sphincter began to gush and overflow. As she removed the bottle, lube rushed across his taint, around his balls and flowed down his cock. Where it dribbled from the mushroom head tip down onto his chest and chin. "wow! That's a wet little boy pussy you got there," Kendra announced playfully, slapping Dan's hole, letting out a loud wet slapping noise and a splash of lube.

She reached into her purse and pulled out a shiny pink vibrator. A loud buzzing hum filled the room as she twisted its base. Before dan had time to ponder the source of the noise, Kendra gradually slid it deep into his hole, then began to methodically fuck him with it. Pure ecstasy ran through Dan's entire body with the intense vibrations inside him, along with the tip of the vibrator poking at his prostate.

"Now, dan, for the first real step of your training. I'm going to begin conditioning you to associate the sensation of being completely covered in cum, with the most mind-blowing orgasms you have ever had."

Her words couldn't be properly grasped. In Dan's current ecstasy filled state, he was barely listening and only retained that he must nod his head in agreement for this sensation of euphoria to continue

Miss Kendra gripped Dan's cock and began gently stroking it as she continued to infiltrate his ass. Dan turned his head to the side, letting out a gargled moan as the saliva that had been building in the back of his throat dribbled out through the ring gag.

"Awh, you've been aching for this all day, haven't you?

"You have been aching to cum ever since the car ride this morning. I know my little slut needs to cum.

"Don't worry, Danny. I plan on allowing my little slut to cum as many times as he wants tonight."

Dan's body quivered in the relief that he would be allowed to finally cum. Using her foot, Miss Kendra pushed Dan's head back straight again.

"Butt... before you get too excited, Danny boy, why don't you look where that little cock of yours is pointing."

Dan's eyes widened as his gaze focused upward at his cock being stroked by Miss Kendra. It was aimed straight at his face. He attempted to turn his face to the side, but Miss Kendra quickly pinned it forward between her feet. His jaws instinctually clenched down on his gag as he now grasped why his mouth was wedged wide open.

"Oh, come on Hun, don't struggle. You can't have your cake and eat it too... oh well, I guess you can," Miss Kendra chuckled.

"Ok. I'm going to give you a choice Danny. I wanna see just how badly you need to cum. So, I'm going to count down from ten as I stroke this little cock of yours and fuck your tight little boy pussy. You can either give in, letting yourself go and spilling that hot sticky load of yours all over your face, or you can try to fight off your orgasm. If you make it all the way to zero, you won't have to cum on your face, but you also don't get to cum tonight. You'll just have to wait until whenever the next time, I'm feeling generous, is.

" So let's see what you really want then.

"Ten," she barked out as she started stroking faster.

"Nine! You know I can make you cum at any moment I want, right? you're never going to be able to hold out."

"Eight!" She slid her hand to the tip of Dan's cock, squeezing At the base of the head, rolling her thumb around the backside. This cause dan to start to convulse and shutter beneath her.

"Seven." Kendra purres with a smirk, "oh, is that the spot?

"Six!" She yelled as she abruptly stopped rubbing his head and started stroking his shaft furiously

"Five. You know it's not so bad, right? What's so bad about a little cum on your face? It's just your own cum anyway."

"Four. Besides, your gonna love the taste. I remember the first load I took in my mouth. So warm and salty. It's so satisfying. put a big smile on my face."