Should Jimmy proceed to the logical conclusion?

Of course!

Chapter 5 by blueroseknight

As if it was responding to his lusty desires, the HUD began to change. The display was replaced by a menu that appeared on the left side of his field of vision. At the top of the menu was the word “Position”. Jimmy was all too familiar with the available options that were listed. “Blowjob”, “Cowgirl”, “Missionary”, “Bent over” and many others appeared before him. Next to the text was a small picture of what each position entailed, acted out by generic, faceless models.

Jimmy often jerked off to thoughts of Maggie on her knees. This was his chance. Just as an unconscious sneer brushed his lips he saw the word “Blowjob” light up. Shockingly Maggie, who had been eying him suspiciously with her hands on her hips, let her arms drop to her side and lowered her gaze. Emotionlessly but not quite mechanically she approached him and dropped to her knees. Before Jimmy knew what was going on he felt one of her soft fingers begin to pull at his zipper.

“Maggie, what the f….?”

“Just shut up and enjoy your blowjob dipshit,” she snarled as she pulled down his zipper and began to reach towards his very erect penis.

There was a sharp disconnect between Maggie’s actions and her demeanor. She was still the boss he knew and loathed but she was eagerly and enthusiastically displaying the kind of affection that was quite uncharted in Jimmy’s life thus far. As she pulled him free of the confines of his pants she began to move her face towards him. Everything was moving so fast. Minutes earlier Maggie’s lips had been curled into one of her patented sneers but now her lips were….

“OH FUCK!”

Maggie’s lips had quickly engulfed his shaft and were viciously working it back and forth. Jimmy couldn’t help but utter a guttural scream of pleasure as she sucked and slurped. Her eyes never left his; even in this moment she was deriding him with her gaze. Even as he fucked Maggie’s mouth she was in charge. She swirled his dick with her tongue with such a high degree of finesse that he wasn’t sure how long he would be able to stand such an intense wave of pleasure. Suddenly the HUD changed again. A few words appeared before him

Free Mode—Command at Will

Jimmy was far from thinking clearly but, amidst the pleasure he was feeling he knew that he wanted to control Maggie further. He wanted to put her in the same state he was in. He wanted her to…

“Touch yourself Maggie,” he breathed. “Masturbate for me. Don’t hold back but don’t cum either.”

“SLLLUUUUURP,” was Maggie’s only reply as she reached one hand gingerly between her legs. Slowly he could see her fingers begin to work their magic on her newly moistoned slit. Soon her eyes lost their controlling glare and became unfocused and vulnerable. Soon, she pulled away as a tiny moan escaped her lips.

“Ahhhh” “nnnnn” she mewled, no longer focusing on him.

“Did I tell you that you could stop sucking?” Jimmy smiled, knowing he had successfully assumed control of the situation. Maggie resumed her oral responsibilities but continued masturbating.

“Mmmph!” ShhlrrmmmmmMMMM”

Jimmy was closer now than he had been but he knew that he still wanted to bury his dick in Maggie’s pussy. He’d wanted to do it for years. Seeing her so vulnerable, so animalistic as she played with her clit while moaning and grunting made him want to violate her in every possible way. Still, he thought, it would be awesome to plaster her face. This was a serious dilemma to consider. As he mercilessly thrusted into Maggie’s mouth he thought of how he could have his cumshot and fuck her too.

Grunting and writhing Jimmy fumbled for a bottle of mayonnaise from the counter. His eyes sparkled as he fondly recollected Maggie’s distaste for the opaque, white spread. Unfortunately for her, opaque and white were exactly what he needed to paint his dream into a reality. She seemed blissfully unaware of his dastardly machinations. His boss had two fingers buried in her fuzzy mound; her eyes were closed while she purred and hummed around his dripping shaft.

“mmmmSHLRP!”

“Hey Maggie,” Jimmy commanded with as much authority as he could muster, “Open your mouth and close your eyes!”

Happily Maggie withdrew her lips from his dick and opened her mouth. Her bubblegum-pink tongue sticking out expectantly. Jimmy savored the site briefly before squirting the tube of mayonnaise all over the girl’s face. The goo got everywhere, having the desired effect and then some. Her pale skin was immediately sullied by the viscous sandwich sludge. Her forehead, her nose, her mouth, her eyelashes and even her hair were covered by his enthusiastic squirts. She was a gooey mess. Maggie screamed.

“What the fuck asshole! I wanted you to cum on my face, not this!”

Even Maggie looked momentarily suprised by her vocalized desire for Jimmy’s semen. He smirked as her face switched from disgusted rage to puzzled confusion to undisguised lust. The most amusing part was that she was still fumbling between her legs to pleasure herself while she admonished him for painting her face with mayonnaise.

“Taste it slut,” He commanded.

Maggie licked her lips and made a satisfying choking noise as she cleaned the sludge off of the outside of her mouth with her tongue.

“Gross,” she breathed.

Jimmy jokingly adopted a doctoral tone, mimicking the voice of his family dentist. “Now, open wide for me. As big as you can!

Maggie obeyed without question despite herself. Jimmy thrusted the dripping bottle into her mouth and squeezed as hard as he could. The choking noises she made were music to his ears. Jimmy guffawed appreciatively.

As his diminutive boss cleared her throat of the hated substance Jimmy thought about the HUD position menu again. Neither of them had orgasmed yet and there was no time like the present. He eagerly willed the menu into view.

I’m getting the hang of this, he thought.

He quickly selected the “bent over” option and Maggie rose to her feet. She was dripping from two different sources and he did not know which pleased him more. She walked purposefully to the counter where the sandwich fixings were displayed and bent at the waste, sticking her ass out slightly towards him. She turned back to face him and said nothing. Her face was a mixture of anger and lust. She wanted him but did not want to want him. Jimmy sauntered forward.

“Kissing a girl before sex would be the gentlemanly approach here but I don’t want to get any of that disgusting stuff on me,” he laughed.

He grabbed maggie by the waist and positioned himself. He did not know if he was her first but he knew she was his. He was not graceful by any means but knew roughly where to aim his aching dick with only a mild amount of repositioning. Without any more forethought he plunged into her.

“AAAAAAAuggggg!”

The noise she made as he fucked her was music to his ears. The boss he had dealt with for so long, his jailer and his unashamed tormenter, was now a mewling slut at his beck and call. He pumped her pussy joyously and she fucked him back. There was no rage in her actions, only submissive desperation as she bent further forward in an effort to let him fuck her deeper and deeper. Occasionally more droplets of mayonnaise fell from her face onto the counter. Jimmy swatted her ass happily as he increased the speed of his rhythm.

“Ngh” “Ngh” Ngh”

Her grunts matches his thrusts evenly. The carnal dance came surprisingly naturally to him. He wondered if it was some other feature of his new glasses or if he was just a natural born sex machine. As he fucked and pondered he nonchalantly grabbed the bottle of mayonnaise and smothered Maggie’s mousey brown hair.

“HeyOOOOOOOOOOOOOOOOOOOHFUCKYES!!!!” Maggie’s protest quickly turned to pleasure as he redoubled his thrusting speed.

“Heyo Indeed,” he proclaimed.

Jimmy didn’t know if it was the warm wetness of her pussy, the humiliating goo on her hair and body or the sweet scent of sex but he could not control himself any more. He needed to cum. He grabbed a fistful of her slimy hair, spread the mayonnaise around her scalp and grunted enthusiastically as he let his own secret sauce escape into her pleading hole. It was the best feeling of his life. Cum spewed forth into Maggie. He was filling her and she wanted every drop of it. Her moans and squeals may as well have been pleases and thank yous. Her bucking hips welcomed him into her. His juices flowed in a seemingly endless cascade into the head supervisor of The Sandwich Shoppe.

Jimmy’s eyes blurred as he finished and he listened to Maggie’s mewling and panting. The menu had disappeared from site and had been replaced by another unfamiliar prompt. Tinting his field of vision was a picture of what appeared to be a smiling balloon. Confetti fell from above the dopey face and under it, in neatly printed hiragana, read:

omedetou gozaimasu

Congratulations to me indeed, Jimmy thought. He had no idea though exactly what his new eyewear was actually congratulating him for.

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