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Monica 51: INSIDE JOB

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Paying the Devil his Due. Jimmy Newton is THE MAN.
9.3k words
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Part 51 of the 63 part series

Updated 06/13/2023
Created 04/04/2017
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"Well done Editors."

Teacher Edna Devereaux congratulated her journalism class on another successful year of yearbook coverage. This school year, thanks to Monica Gift and her Braless Brigade, hell everyone in school pretty much, the book was flooded with well orchestrated behind the scenes pornographic photos. It was a good thing Edna had poor eyesight. Additionally, now with Principal Lloyd Janson turning his head the other way to their perversions in light of his own pleasures, they had the yearbook of the century heading off to the printers. Monica had Lloyd by the balls now that he had let it be known that his secret lifestyle as a male submissive seeking her as his dominant was out in the open. He had recently bought her at the Slave for a Day charity, Monica presuming she would be his slave never saw what was coming. Once Lloyd let her in on what he knew about her antics in school she considered her upcoming graduation to be moot. How very wrong she was.

Lloyd begged Monica to control him, to treat him as a worthless piece of shit. Funny, considering he was the leader over some 3,700 students in High School. His power was on the outside, his switch now off, his inner most demons sought to be abused. She needed the experience so Monica managed to bluff her way into being his Mistress of BDSM. A sworn oath between them, Lloyd had now lost all control over himself, in honor of Monica the Magnificent. She made Janson her bitch, the remainder of the school year was going to be awesome. Now, if she could just do everything she wanted without getting Lloyd fired.

Luckily for Janson the male Teachers at least knew of some things he had done, just as he knew of things they had partaken in. Everyone had a guilty mark in their career, so nobody wanted life to be any harder than it already was. With a vast majority of the student body backing Monica and her brigade of beauties those that had seen or taken part were loyal. One slip it was game over for everyone. The trouble is, everyone involved even by saying nothing were associated, so if one falls, so falls the empire. A little under two months more and everyone could sigh with relief.

Now that the yearbook was off to press, there were debts to be paid. A certain class photographer was calling said debt due. Jimmy Newton was still a virgin. Although nervous, he was ready to end that reality in spades.

"Let's do this." Jimmy threw his overweight bulk against the lockers next to Monica making her jump and drop her books. Catching her breath she just bulged her eyes.

"Scare the hell out of me why don't you?"

"Sorry! It's been two weeks now. The auction is over so there's no reason to use that as an excuse anymore. I did everything you guys asked of me. I want to get laid."

"We both know Sonya would give it up to you, just ask her."

"I like Sonya. I reallllly like her, but I know me. If I get with her first I'll wanna be faithful. I need to be a playa first, while I can. Please tell me the Brigade won't let me down, I have faith in you Monica." He looked worried that he himself was being played.

"Obviously, I can't force any of them, but they did swear to me they would keep their word. Loyalty among ho's."

"They hate me don't they? If I make them go through with it I'll be on their boyfriends shit list." He grew panicky, "I'm dead I just know it."

"Let's find out if you need to be fitted for a body bag." She looks to her blind side to spot her friend Toby at his own locker, just closing up. Seeing Monica look his direction made the boy smirk and move in for the kill. As Monica calmed Jimmy, Toby eased up behind her and gripped Monica by her hips, pressing his body into hers then dry humping her ass over her skin tight leggings for better effect. Laughing at Toby she winked at Jimmy, "And, here's our first verdict."

"What's up slut?"

"Toby? How do you feel about Jimmy having sex with your girlfriend Lindsey?" Hearing her Toby stopped humping her in favor of a temper tantrum, nudging her aside he doubled up a fist sharing it's threat with Jimmy.

"YOU'RE DEAD MEAT NEUTRON." As Jimmy cringed expecting to be punched, Toby changed his tune laughing, "Chill out Nerd. Lindsey likes being spanked, so bend her over your knee."

"Y'you're good with...?" Jimmy swallows dryly.

"Yeah! We're open like that." Toby then leans closer to whisper, "Nibble her earlobes and she goes crazy."

"Wow! I-I'll do that. What will she think? I mean I'm not a stud like you...not that I'm looking at you..." He begins sweating heavily.

"Relax Buddy. I'm cool with this deal you and Monica made. The girls all agreed so tap all those bitches. I know I would...well I've had a few of them already, such as Monica here, which I want again. Hint fucking hint!" He grabs Monica yanking her into his side, his hand draping down over her shoulder to squeeze her breast.

"Your birthday's coming up right?" She moves her own hand over to cup his hard on, his attention lowering to see her pinching his erection through his jeans. A few onlookers found them amusing.

"Damn straight. You my present?"

"We'll talk about it when it gets closer. Can I let you know next week? Lots going on right now."

"That works."

Keeping her free time sacred in case her friend and occasional Master Ryan Quinones needed her. He wasn't even at the auction, and had missed school a few days in between. She had promised his girlfriend April time to get everything sorted out. Which meant a true Doctor's appointment to define her pregnancy and to let Ryan meet her family. If she really was pregnant like she said, and really did want to be with Ryan then she had a lot to atone for. Monica worried, but knew after their confrontation that she needed to stay out of it. She had already given them plenty of time to talk. If it were bad, Ryan would most likely tell Monica. Still, she needed to be open if he required a shoulder.

"So Toby?" Jimmy tried to keep calm, "Do you think all the other boyfriends will be as cool as you?"

"Naaa! You'll be sporting a couple black eyes by the weekend." Toby moved behind Monica and dry humped her again. It was fun to see their audience admiring him getting away with what he was doing. Not to mention seeing him tug her leggings down over her bare bottom in order to rub his erection along her ass more intimately had the drool flowing like a broken dam. Only her books hid her puss from their visual appetite.

"Stop scaring Jimmy." She laughed, "You have to stop humping me like that, I'm getting really turned on."

"You're up Neutron. I got Monica ready for ya." He nudges her toward Jimmy until she ends up smothered against his body. Meeting eyes Monica shrugs at Jimmy with a grin. Sitting her books down she took him by the hand and led him through the gauntlet of students, her leggings still crumpled down to her butt pucker, her pussy hidden behind the soft leggings curled up state. Toby casting a thumbs up at Jimmy led to a flurry of support. Seeing him be straight with Newton, other classmates offered their own thumbs up to bolster his confidence.

Tugged along at an accelerated pace Jimmy found himself almost humiliated, yet enthusiastic all the same, "W-where are we going Monica?"

"We've had phone sex James, now it's time for a reality boost. Once I get those balls on a roll the other girls will come looking for you. They just don't know it yet."

"Hard to imagine that, I'm so not their type."

Stopping cold in her tracks she points a finger at his chest, his pudginess squishy beneath her dagger like nail, "Opposites attract. It's all in how you sell yourself Jimmy. We're calling you Black Friday."

"Black Friday?"

"Yep! Everybody wants what you're selling and they're willing to fight for it. If that means a few bruised egos...the seller always wins."

"Umm? Yeah, okay. I don't get it."

"Neither did the people who lagged behind."

"Still don't get it."

"No worries. You will." Switching tactics she leaps into poor Jimmy's arms, her body crushing into his. He nearly fainted as her breasts pressed into his fluffy pecs in competing awareness. Her perfume made him hard even though fear derailed him into a tug of war to remain erect. Then came the kiss, her lips were like honey, passionate and expectant of him to return the favor. Jimmy fell right into her ambitious approach. All around them students were praising him for getting the hot girl. He knew deep down that they were mocking him but biting their tongues to keep Monica from biting theirs even harder, drawing blood. Sure she had made it clear through the grapevine that Jimmy Newton was not to be ridiculed going forward. The fact that he helped the entire student body in some small fashion during the yearbook fiasco gave him a pass to be a man. Strangely, some girls found it fairytale. Others? Not so much, still hiding in the shadows for safety.

Murmurs were heard even as the next period bell rang. Gaining confidence as the students lessened up around them Jimmy's hands found Monica's butt cheeks beneath her ruffled leggings which had risen a bit unattended. Some students remained until the last possible second, enjoying the awkwardness of the couple, Jimmy was a goofy lover for certain. Her ass hanging out some was hard to break away from. Only Monica's hotness kept the comments to a minimum of ridicule. It was enough to relax Jimmy that he and she were in good hands. His in particular unintentionally prying her ass cheeks wide for guys and girls alike to witness her pucker and her whistler. Good enough for the masses in passing.

It wasn't as if Monica was truly enjoying herself making out with Jimmy, or he pawing her up, but she was a woman of her word. She made this crazy deal, she would honor it. All she could hope for was that her Braless Brigade could act the same. A few she knew would, having seen Jimmy's dick in the men's room, it was amazing what a big dick could do to change an outlook. Amber Welch came to mind. If Amber would follow behind Monica the rest might gain the courage to hold their own.

With her hands all up in Jimmy's hair like a possessed stalker, his glasses fogged up, and slipping from the bridge of his nose neither Monica nor Jimmy had heard a distinct, "AHEM!" until the third exhale. Each time it was spoken the voice grew louder. Nobody wanted to go to class but eventually the halls cleared out at the very presence of a certain voice of authority.

"Wait your turn." Monica whimpered , kissing Jimmy harder as his face turned beet red. He knew the voice well, panic was slipping into his sensibilities. Still, he trusted Monica. All it took was Principal Lloyd Janson to stand behind her and slobber at her ass cheeks, Jimmy swore he heard a low level, "Yes Mistress."

With no further words to discourage them the make out session continued. Lloyd grew nervous as he leered in all directions for prying eyes. Sweat pouring he watched her maul poor Jimmy, the boy nearly losing balance and colliding with a set of lockers with a metallic bang. Janson worried the noise would attract attention but fortune struck and all classrooms remained vigil, his troops were good Teachers loyal to their trade. Still, the kids were a hallway pass away from having to be shut down.

Now that Lloyd had shown Monica how to express her dominant side Lloyd wanted nothing more than to worship this young adult. She had eased into her Mistress role as if it were there all along. Maybe it was. Yet, she preferred being the giver not the Alpha. The Alpha was pure adrenalin. If it served her purposes in getting away with murder, Monica Gift was going to channel her inner Bitch for all she was worth. Rich indeed.

Letting Monica continue was a huge risk for Lloyd, but his newfound loyalty defined his perverse desires to the point that saying no was forbidden. Continually, he found himself wanting to touch her butt right along with Jimmy's lucky palms, yet, afraid to interfere and be scolded by his Mistress. Janson was putty to be molded. For such a wise man he was stupid beyond measure. Monica counted on that. It was likely that they all needed therapy. Someday.

Jimmy facing reality opens his eyes to see Janson still behind them, even as Monica maintains her dedicated kisses. One panic attack later, he breaks away from their kissing in a nasally whine. Reacting to Jimmy's haunted expression, Monica leers over her shoulder and scowls, "Why are you not on your hands and knees Janscum?"

"Forgive me Mistress." Lloyd drops to his knees and folds forward, palms at her heels, eyes lowered for respect.

"Don't make me go behind you and kick you in the balls." She snaps as the Principal quivers at her aggressive tone.

Jimmy Newton exhaled a dramatic, "Whoa!"

"Don't let this big pussy scare you James. Where were we?" Her arms wrapped Jimmy's neck and she hurled herself forward for more kissing, storming Jimmy's nervous lips for another three minutes of passion. He was slowly giving in. Frenching Jimmy was like a dog licking her hand, certainly sloppy. Abandoning Jimmy's still wagging tongue she pats his puffy cheek with an expectant glare forcing his gaze. "Lay me over Janson's back."

"WHAT?" Jimmy's voice raised just as she palmed his mouth to quiet him.

"You heard me Jimmy." The boy nearly pissed his jeans.

"Invite me Lloyd. Show Jimmy he has nothing to worry about."

"Please lay upon my back Mistress." Lloyd begs, "You have my blessing Young James."

Swallowing with trembling eyes, hell every part of his body sharing in the quakes, Jimmy looked around both sides of Monica, "W-which direction?"

"My ass on his neckline, nudge me all the way back, he won't let me fall off. WILL YOU LLOYD?"

"Absolutely not Mistress. My hands request touching to keep you positioned."

"Only if I start slipping, otherwise forbidden."

"Yes Mistress."

"Guide me back Jimmy."

"O-okay! S-sorry Mister Janson." The pudgy young man felt faint, yet he did assist her into sitting down on his Principal's shoulders, he heard Lloyd mumble, "Yessss." As Monica lays back slowly for a comfortable spot, her legs rise up toward Jimmy, feet poised before him, "Take my shoes off." James swiftly removed her pumps. She in turn lowered her bare feet over Janson's face smothering his feature with the sides of her heels. "Lick my toes Lloyd. Doggy treat Bitch Boy." Jimmy watched Lloyd's persona becoming a slobbering canine, his tongue licking her feet and even between her toes at her insistence, "Eat my toe jam." ,until she pulled them away. Lloyd's feasting frenzy terrified Jimmy, Jimmy's mind was blown as Janson whimpered missing his treats. Another ramble of, "Dear God Woman." was heard by all.

"Jimmy? Take my pants off."

"W-what? Over Mister Janson?"

"DO IT LAD." Lloyd belted out excitably, "STRIP HER NAKED."

"Who's in charge here, you or me?' Monica jabbed Lloyd in the ribs hard with her thumbs.

"You Mistress. I beg forgiveness for my lust."

"This is unreal." Jimmy commented at their acts. Turning pale he pauses until Monica plants her toes over his erection rubbing it.

"Pants Jimmy." She persists lifting her hips using her shoulders as support over Lloyd. Jimmy with sweaty palms leans in and begins peeling her leggings from her lower body, dragging them inside out until they left her painted toes. No underwear beneath, Monica Gift was nearly nude. Frozen in time the boy stared at her freshly shaved peach in its bright pink glory.

"Guess what's going in here Jimmy." She pries her pussy lips wide to reveal a succulent tunnel of love. Her beguiling gaze awaited his eyes to focus, those damned glasses of his were steamed up to the point of being blind. "Lean down here for a second Jimmy." She curls her foot like a hook beneath his balls and guides him toward her. Once he bends forward she removes his glasses and lets him squint at her, he really did need those things to see. Frowning Monica chose the next best thing and used her finger to etch a tiny heart in each of his lens before putting them back on his face. He chuckled seeing them and felt his heart beat faster at her intentions.

"YESSSSSSS!" He rears upright and pounds his fist over his opposing palm. He then tilted his glasses just enough to let fresh air clear up his fogged over optics. Seeing more clearly than ever he did his best to ignore the fact that Lloyd Janson was right there with them. He had Monica halfway nude over him as if he were a horse and she Lady Godiva.

"Unbutton my shirt and take it off of me Jimmy." Responding to her request Jimmy Newton started to move to Janson's side when Monica's foot again was used to reel him back. "Ah! Ah! Ah! Face me and do it." Her soft voice had Jimmy and Lloyd both nurturing raging hard ons.

"But, that means..."

"Grow some balls Newton. Hurry it up or the next bell will ring before you cum inside me." She raised her voice slightly with a look of yearning to agitate his desires.

Seeing her appeal Jimmy gnashed his teeth together and moved in for the kill, forced to literally plant his crotch over Janson's face in order to lean in better and begin unbuttoning her shirt. No bra beneath it of course Jimmy fell in love with every ounce of soft flesh that exposed. Janson had to wince at feeling Jimmy's dick growing right up against his brow. Uncomfortable indeed, yet Janson was loyal to Mistress Monica. He would not waver even if it cost him his job.

"How are you doing down there Knave?"

"I live to serve you Mistress. I shall remain your most loyal of bed chambers."

"Good boy Knave. You are rather comfy."

"Thank you Mistress." He replies as Jimmy unfastens her final button and parts the material to both sides for a full frontal thrill, her nipples harder than usual. Even this event seemed to be making Monica more in tune with her newfound authority. It was good to be Queen. Lifting just enough to pull her arms from her shirt Monica found total release.

"Get those jeans off Jimmy, and put that big boy between your legs to use right here." Again she pries her cunt wide and uses her index fingers to point at her interior runway. He could see her wetness forming droplets all around her fingertips. Excitably Jimmy Newton began to unfasten and drop his pants, the second his erection popped out Monica wiggled on Lloyd's neckline, "Look at how big he is Knave. Have you ever seen such a magnificent cock?" She laid it on thick, mainly because it was pretty thick, there was no denying that fact. For an overweight young man he was pretty well endowed. Not that Lloyd Janson cared to look, even if he did obey her. With Jimmy's dick dangling before his nose Lloyd held his breathe and replied, "Yes Mistress. Young James is...quite remarkable." A retaliation hidden behind his breath said differently, "Get that monster away from me." Regardless Lloyd endured the moment, knowing it was about to get far worse. He knew that Monica was testing him as much as she was Jimmy.

"FUCK YES! FUCK YES!" Jimmy grew eager, "I'M GONNA LOSE IT. FUCK YES!" The boy was determined to become a man. With Monica luring him in with soft verses of, "Take it Jimmy! Take my pussy." James Newton shuffled forward with an obsessed glint in his eye, the whole stress over Lloyd was fleeting. Uncaring of his environment he zeroed in and touched Monica's hole, she prying it even wider watching him close in. She was definitely hot in every sense. Forced closer in order to penetrate her Jimmy slid his crown in to royalty, the moment she felt him enter she released her pussy and let it mold around his girth, the rest of the insertion made Jimmy roll his eyes back. He had never felt such a warm welcoming feeling in his entire life. Sinking deeper the boy nearly toppled poor Lloyd over beneath his weight.

Holding firm as best he could Janson found his worst nightmare in the form of bulbous hairy balls pelting his forehead. He wanted to vomit but survived when he felt Monica's nails dig into his ass cheeks, her arms over her head and running fingers beneath his beltline. She knew just how to make Lloyd respond to her control over him. He was more determined than ever to stay firmly on course for his Mistress, her pleasure his priority.



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