Hidden Camera Ch. 02: Jacksons Education

As soon as he was in his apartment Jackson took a hasty shower, uncomfortably aware that his cage made it harder to urinate and he had ended up having to sit on the toilet just to manage before wiping himself clean. As soon as he had toweled off Jackson picked up the putt plug and turned it over and over in his hands.

"Shit!" Jackson finally exclaimed and opened his cabinet to pull out a bottle of KY.

After spreading a generous dollop over the entire toy Jackson squatted down and placed the pointed egg against his anus. He began to twist the toy left and right while pressing in, his anus slowly stretching to allow more and more of the egg inside of his body. When the widest part of the toy passed his tight sphincter Jackson couldn't help but gasp as his ass sucked the toy into place.

"I can't believe this shit..." Jackson gasped with the toy pressing firmly against his prostate while giving the sensation of being full and ready to go to the bathroom.

Jackson stood carefully and grabbed his boxers from the bathroom counter before hesitating and then tossing them aside. He was pretty sure Susan wouldn't mind if he went sans underwear and stepped into his cargo shorts before pulling a tight fitting Under Armor shirt over his head. After a final quick glance in the mirror Jackson put on his Teva's and headed out the door. At almost eleven at night on a week day Royal Court looked to be nearly deserted with most people already inside watching late night television or asleep, Jackson's steps the only sound besides a passing car on the main road two blocks away. As he reached Susan's apartment he saw that the curtains had been closed but he could still see light shining around the edges.

Jackson didn't hesitate as he walked up and knocked on the door and after nearly a minute the door opened to reveal Susan wearing a black leather harness covered in pointed silver studs. Black straps draped over Susan's shoulders to plunge down before dividing into two diamonds to frame each one of her slightly saggy C cup breasts. Another leather diamond framed her stomach with her navel perfectly centered and her mound covered by a tiny slip of shiny black leather. Even Susan's feet were encased in black leather straps with Roman style gladiator sandals that came up to just below her knee. Jackson could only stare at Susan's exposed, tanned body as she stood in her doorway for anyone who happened to be in the parking lot to see until he jumped when she snapped a riding crop she held that he hadn't noticed.

"Well, 'Good evening, Mistress' would be a very good way to start," Susan said tartly while still just standing in the doorway.

"Ahh, good evening, Mistress," Jackson parroted.

Susan continued to only stare at Jackson while standing in the doorway and he wondered if he had forgotten to say or do something as he shifted from foot to foot and glanced out towards the dark parking lot.

"Did you put your plug back in?" Susan finally asked while tapping the riding crop against her thigh.

"Yes, Mistress," Jackson instantly replied.

"Ummm, so my spoiled little brat is capable of learning," Susan said with a slight smile, "Come in, Jackson, I've been anticipating your training all day."

Jackson stepped inside to kick off his Teva's and after another moment of being perfectly framed in the light spilling out of her living room Susan closed the door and followed him. Jackson immediately spotted the video camera on its tripod with the red record light blinking as he walked to the center of the living room and turned to face Susan, his eyes once more crawling over the dark tanned skin of her exposed breasts and tiny leather thong.

"When you come inside my home from now on Jackson you will immediately take all your clothes off," Susan instructed as she stood and watched him.

"Ok," Jackson replied and began to pull his shirt over his head only to flinch when Susan snapped her riding crop against her thigh.

"That's not how you're supposed to answer me!" Susan said severely.

"Yes, Mistress," Jackson quickly corrected and then finished pulling his shirt over his head.

Susan nodded while watching Jackson toss his shirt aside and then gave a small smile when she saw that he hadn't bothered to wear anything beneath his shorts. Jackson's dick was already straining inside his cage as he stood naked and Susan began to slowly walk around him as if inspecting him. She reached down to fondle his caged penis for a moment before her fingertips stroked lightly over his hip and around the curve of his ass.

"Bend over," Susan demanded.

Jackson bent at the waist and grabbed his ankles and then cried out in shocked surprise as he felt the riding crop smack across his ass.

"What did you forget to say?" Susan demanded.

"Yes, Mistress!" Jackson gasped as the stinging across his ass cheeks lingered.

"Better," Susan said and Jackson again gasped when he felt her give the butt plug he had inserted earlier a gentle tug, "Do you like your ass filled?"

"I... I don't know, Mistress," Jackson confessed, not wanting to admit how good the pressure against his prostate felt.

"Hmmm," Susan said speculatively and then brought the riding crop down across Jackson's ass again.

"Oww!" Jackson cried in surprise, his ass still stinging from the first time Susan had smacked him.

"Let's talk about you filming unsuspecting women, Jackson," Susan said pleasantly and brought the riding crop down again.

Jackson cried out as Susan suddenly began to use the riding crop to strike him in quick, sharp, stinging blows, his knees almost buckling in his shock.

"You will not!" Susan said severely as she smacked her riding crop across Jackson's ass cheeks, "Ever! Film! Women! Without! Their! Permission!"

Each word was punctuated with another sharp blow, snot and tears running down Jackson's face as he tried to not cry until he flinched when he suddenly felt Susan's hand caressing his stinging ass.

"Do you understand, Jackson?" Susan said pleasantly, "You will never, ever record someone without their permission again?"

"Yes, Mistress," Jackson gasped and tried to wipe the snot from the tip of his nose.

"If I ever catch you again I won't be so nice," Susan said as her fingers gently tugged at the plug still buried deep in his ass, "Now stand up."

"Yes, Mistress," Jackson said and quickly stood up, his ass still burning as he imagined all the red welts Susan had left behind.

"Good," Susan purred and then pressed her body against Jackson's back as she reached around to take his caged penis in her hand, "Did you enjoy your cage today?"

"I... ah... no, Mistress," Jackson said and closed his eyes as he felt the tips of Susan's fingernails playing with the flesh of his penis straining through the brass bars of the cage, "Can you take it off, please?"

"Oh, no," Susan purred and bit the back of Jackson's shoulder lightly, "I don't think I can.

"Come on."

Jackson turned to follow Susan back to her bedroom, her hips swaying with each step and the leather strap of her harness hidden between the cheeks of her ass.

"You did a wonderful job this morning for me Jackson," Susan said as she walked slowly down the hall, "But I do have to admit, I really missed having something nice and long and hard stretching me open.

"So I have another job for you."

"Do you mean..." Jackson began hopefully, his penis swelling painfully inside his cage, "Are you going to take this thing off of me and let me fuck you, Mistress?"

Susan glanced back over her shoulder with a smile before shaking her head, "Oh no, nothing like that."

Susan stepped inside her bedroom, the covers and sheets on the bed already turned then turned to face Jackson. He watched as her hand reached down between her thighs and after only a moment the leather piece covering her mound fell to the floor exposing her already moist inner lips. Susan let Jackson look at her for several moments and then climbed up onto the bed and spread her legs wide apart.

"Come here, Jackson," Susan purred.

"Yes, Mistress," Jackson said and tried not to whimper at the pressure of his penis constrained in his cage, tried to ignore the burning sting of his ass cheeks and hurried over to stand at the edge of the bed.

Susan slowly and languidly reached over to her pillow and then brought a large purple dildo out from behind it to show Jackson.

"Since you did such and amazing job this morning devouring me you are going to eat my pussy again Jackson," Susan purred and held out the dildo for Jackson to take, "But you're also going to fuck my pussy with one of my favorite toys while you suck on my clit."

Jackson glanced from the dildo in her hand down his penis still confined inside the hateful cage and then back up into Susan's hard, gray eyes.

"Yes, Mistress," Jackson said and climbed up onto the bed and between Susan's legs as she handed him the dildo.

Jackson took the dildo from Susan when she handed it to him and then leaned down to blow lightly across her already exposed and swollen clit.

"Ohhhhh, that feels exquisite, Jackson," Susan moaned, "Are you trying to tease your mistress?"

Jackson grinned and blew across Susan's clit again, her inner lips opening to reveal her juicy vulva contracting each time his breath caressed her button.

"Ohhhh, yessssss," Susan moaned again just as Jackson lowered his head to slip his tongue into her vulva.

Susan's strong, pungent flavor filled Jackson's mouth but with a hint of something flowery added. Jackson pressed his face down, his tongue questing deep inside of her as he licked her silky smooth flesh while her legs squeezed down on either side of his head.

"Use the toy!" Susan gasped, her hips giving small little jerks until Jackson pulled away.

Jackson took a moment to look at the dildo in his hand which was much bigger than his own dick, caged or not, prominent veins running along the shaft and hard ridge circling the purple glans and then ran the tip up and down between Susan's wet folds. As soon as he had the head lubricated he pushed the glans slowly into Susan's vulva, marveling as he watched her body stretch open to accept the full circumference of the shaft.

"Ohhhhhh, yessss, suck on my clit, Jackson," Susan moaned.

Jackson took another moment to watch Susan's lips spread open as he slowly pulled the toy out of her body before closing in an intimate embrace when he pushed it back in, her vulva stretched tightly around the shaft already coated in a creamy white honey. Jackson had to make himself look away from the erotic view of a woman's pussy being fucked from only inches away, a sight he had only seen in online porn before and then leaned down to let his tongue flick across Susan's prominent clit.

"Ohhh, just like that, Jackson!" Susan moaned, her hips lifting off the bed and her hand pressing Jackson's face down against her clit.

Jackson let Susan's hand on the back of his head guide him, his tongue flicking and licking across her clit with the constant pressure of her forcing his face down. Susan's hips began to buck up each time he forced the dildo into her body, the smell of her musky aroma growing stronger as he began to suck hungrily on her engorged clit.

"Ohhh, god... ohhhh, don't stop!" Susan moaned, her hips bouncing up off the bed as Jackson fucked her with the dildo.

Suddenly Susan's body stiffened, her hips shuddering as she held her ass high up off the mattress. Jackson hummed against her clit with her fingers twined through his hair and pulling painfully as she forced his face down. Almost a minute passed before Susan gasped and collapsed back on the mattress, her hand stroking the back of Jackson's head.

"Oh, my god, that was good," Susan managed to gasp after recovering for several moments, "I want you to pull my toy out of my pussy and lick them both clean for me Jackson."

Jackson blinked, the idea of licking Susan's pussy that had a thick white cream dripping down from her vulva still stretched around the shaft of her toy not bothering him in the least, but having to lick the dildo...

"What do you say, Jackson?" Susan asked a bit more severely.

"Ahh, yes, Mistress," Jackson quickly replied and then slipped the dildo slowly out of her body.

Jackson eyed the purple shaft covered in milky cream doubtfully before leaning down to lap up the flow that had gushed out of Susan the moment the dildo had slipped free. Susan's pungent flavor was just as delicious as he remembered from this morning, his penis straining painfully inside his cage as he sucked each of her lips into his mouth.

"Mmmmmm," Susan moaned contentedly with her legs spread apart, her hand stroking the back of Jackson's head as he continued his efforts.

After several quiet minutes Susan shifted enough to glance down at Jackson who was licking the insides of Susan's thighs.

"I think you've forgotten my toy, Jackson," Susan said with a smile.

"Ahhh, yes, Mistress," Jackson said with a wide eyed glance up to meet her eyes before reaching over to pick up the dildo.

After another glance at the veins along the length of the shaft Jackson took a quick breath and began to lick the soft, rubbery surface.

"You don't know how hot that is, Jackson," Susan purred as she watched him lick the dildo clean, "So many memories of having two young men to train together in how to perfectly please and pleasure me."

Jackson froze at the thought of having to spend time with another guy, his eyes flicking up to meet Susan's who laughed in delight.

"Oh, don't look so worried," Susan said and then began to sit up on the bed, "I'm enjoying myself way too much training just you to share.

"Well, for now at least. Now, how does your dick feel, Jackson."

Jackson glanced down at his caged penis still straining to achieve and erection which was equal parts pleasure and pain.

"I... ahhh, when are you going to take it off, Mistress?" Jackson said plaintively.

Susan only smiled and got up off the bed to stand over Jackson.

"I want you to get a toy for me, Jackson," Susan purred, "You'll find it in the bottom drawer of my night stand."

"Ahh, sure, yes, Mistress," Jackson said in confusion and got up off the bed.

Jackson hurried over to the drawers Susan pointed to and opened the bottom one, his heart slamming in his chest when he saw the large black strap on dildo.

"Take my toy out and bring it over to me so you can put it on me," Susan instructed.

"Ye... you're not..." Jackson began before hastily starting over at the glare Susan gave him, "If I may, Mistress, you're not going to use that... on me... are you?"

"Yes, Jackson, I am," Susan responded with a smile, "Now hurry up and bring it over here."

Jackson glanced down into the drawer again and then picked up the strap on toy by the leather belt. He felt a little reassured in that the phallus was only half the size of the one that he had just been using to fuck Susan with, but still, the idea of Susan using it...

"Hurry up, Jackson," Susan said again.

Jackson jumped when he realized he had just been standing there staring at the strap on in his hand and hurried over to Susan who held her arms out wide.

"Put it on me, Jackson," Susan instructed.

"Yes, Mistress," Jackson said and felt his face flush at the sound of his voice breaking in his nervousness.

It took Jackson only a moment to run the belt around Susan's waist as his heart thundered in his chest. Susan reached down to stroke her phallus as if she were jerking herself off while she checked and tightened the belt while staring into Jackson's eyes.

"Bend over the bed for me Jackson," Susan said huskily once she was satisfied with the fit.

"Ahh, I... I don't know about this," Jackson stammered.

"To bad you don't have a choice," Susan replied, "Now turn around and bend over and the next time you forget to include Mistress I'm going to strap your ass again!"

Jackson stared into Susan's eyes for several moments, his breath coming in quick pants before finally giving a slight nod.

"Yes, Mistress," Jackson said and turned around to lean down onto the bed.

"Good," Susan purred, Jackson flinching when he felt her soft hand stroking the flesh of his penis still straining between the bars of his cage, "Very good, Jackson."

Jackson flinched again when he felt Susan's other hand stroke up and down between his ass cheeks, a fingertip toying with the butt plug inside of him while still teasing is caged penis.

"Ohhhhhh!" Jackson cried out when he felt Susan cup and squeeze his aching balls.

"Poor baby," Susan cooed, "Your, poor, tiny little penis is fighting soooo hard to break free isn't it."

Jackson closed his eyes and bit his lip when he felt Susan tug at the plug still inserted in his ass and then gasped when she pulled it smoothly out of his body.

"Are you ready to be violated Jackson?" Susan asked as he felt something press against the sphincter of his ass, "Just like you violated all the women you filmed?"

Jackson panted for breath and then cried out when he felt Susan's phallus press into his asshole, her hand still cupping and squeezing his balls. Jackson opened his eyes and peered down between his legs at the sight of his caged penis and Susan's hands, her long, slender fingers playing with his sack as he felt her press deeper into his body.

"Does that feel good, Jackson?" Susan purred when she had her belly pressed firmly against his ass cheeks.

"I... I don't know... Mistress," Jackson panted even as he felt the pressure building in his balls that meant he was close to an orgasm, "Ohhh, maybe."

Susan began to rock her hips, her phallus slipping in and out of Jackson's tight asshole and he couldn't help but moan as she squeezed his balls tightly.

"Oh, Jackson," Susan cooed, "It certainly sounds like you're enjoying yourself.

"Does it feel good to you?"

"I... no... Mistress," Jackson panted while trying to ignore the sensations tearing through his body.

"Tell me the truth Jackson," Susan said softly, "Tell me if you like me fucking your tight virgin ass and maybe... just maybe I'll let your poor, tiny little penis out to play."

"Ohhhh, shit! Yes! It feels good, Mistress," Jackson blurted, his face a bright red at letting that honest admission slip out.

"Umm hmm," Susan said and began to pump into Jackson's ass faster and faster.

Jackson placed his forehead down on the cool sheets, the pressure of his orgasm building as Susan fucked him and fondled his balls until she suddenly pulled her phallus out of his body.

"Turn around on the bed for me Jackson," Susan panted, "Hurry!"

Jackson turned around and looked up to see Susan taking a thin silver chain from around her neck, his eyes drawn to the small key dangling from that chain.

"Climb up on the bed and spread your legs for me, Jackson," Susan demanded as she brought that key down towards Jackson's crotch.

Jackson's eyes never left Susan's hand as he spread his legs apart, never realized he was biting his lip hard enough to draw blood as she inserted the key into his cage, never paid the slightest head to his moan of pleasure as his dick was finally released and he instantly swelled to a full erection.

"Ahhh, god, that feels so good!" Jackson exclaimed and then only watched as Susan stepped up to the bed between his legs.

Jackson had only a moment to realize what she was doing before she pushed her phallus into his ass again while using a free hand to reach down to start stroking his hard dick. The constant sexual arousal from having been forced to wear the cage all day, the teasing and denial of having been made to go down on Susan without any reciprocation, the feel of her strap on in his ass and her hands squeezing his balls combined now with the pleasure of Susan's hand moving up and down his length while she thrust into his ass with her strap on was to much for Jackson.