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Annie Edison: Script Supervisor	By : TheChemist Category: 1 through F > Community Views: 3982 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I have no association or ownership of Community nor its characters, especially The Dean, Annie Edison and Jeff Winger. I make no money from this story

Chapter List
- 1-Annie/Jeff
- 1
   “We’ve being doing this scene for 12 fucking hours!” Jeff shouted, unable to handle his frustration anymore. “I can’t! I just can’t.”
   “Jeffrey! No!” the Dean shouted as the man who was playing him in the commercial stormed off set. “Damn it!”
   “But we need him!” Annie pouted, equally broken hearted. “What do we do?”
   “First, we get these two,” the Dean explained, flicking his head towards Troy and Britta. “To actually complete the scene. Secondly, we get Jeffrey back. By any means necessary.” With that, Dean Pelton gave his younger and very attractive assistant a good up-and-down look over with his eyes.
   Even a more inexperienced girl like Annie caught the Dean’s eyes roaming over her exceptional body. Her dark hair may have been a little messy in its bun she wore, but the rest of her was looking as top quality as ever. Though the group tried not to sexualize Annie in their first year when she was a ripe 19 year old, Annie was now 22 with more maturity to go with her insanely perfect body. Though a mere 5’1 tall, Annie somehow possessed toned muscular legs, a nice thick ass for a petite nerd and breasts that could only be contain within a sturdy D cup bra. Matched with her flawlessly adorable face and big doey eyes, Annie Edison was a knockout in every sense of the word.
   “What do you mean, Dean?” she asked, though having a good idea already.
   “Listen to me, Annie,” Dean Pelton roared, his psychosis being worn for all to see, except to his assistant that he was currently yelling at. “Jeffrey Winger is the star of this whole show. We need to keep him happy, and more importantly, in character.”
   Annie, unfortunately, had bought fully into believing that Dean Pelton was a genius with his vision for this commercial, instead of correctly assessing that he was fully off his rocker with insanity. It was why she was taking her job as script supervisor so extreme, mainly because Stockholm Syndrome is indeed a powerful psychological effect.
   “Tell me what you need, boss,” Annie said after straightening herself up and taking her silky hair out of its messy bun.
   “Pretty simple. While I light a fire under these two and get the shot we need, you will go find Jeff in my office,” the Dean explained. “You’ll look the door behind you and you will work the stress and unhappiness from that gorgeous man, leaving only the energetic and engaging man needed to play me in my work of art.”
   “Okay, okay,” Annie agreed, rolling her shoulders and preparing herself for her job. “Now the goal is to appease Jeff but keep him in character as you...but I feel like you and Jeff may have very different tastes...in people...physically.”
   “Mouth and butt,” the Dean replied without hesitation. “Any red-blooded male, despite their...other appetites...well, blowjobs and anal sex suffices for ever man.”
   “Oh,” Annie replied, her lovely mouth hanging open in a little surprise.
   “Is there a problem Annie?” Dean Pelton asked with a stern look in his eyes that he had thus far reserved only for Troy and Britta.
   “No, no sir. None at all. I fully support your vision and am committed with all my heart to making it happen,” Annie said, though with a chink in her resolve, which didn’t go unnnoticed by her boss.
   “Star-burns!” Dean Pelton shouted and moments later Greendale’s most notorious drug deal came running towards. “2 pills of your highest concentrated dose of Adderall. Now!”
Like Annie and dozens of other students, Star-burns had been wrapped up in the Dean’s mad vision for this commercial. Without regard for the fact the dean of the community college was watching, nor that the head of security was mere feet away as well, the man known as Star-burns took a bag of white pills from his backpack, pulled out 2 and handed them to Dean Pelton, who in turn offered them to the large-chested Annie Edison. Though she hesitated initially, Annie broke her 3 years of sobriety by throwing the offered drugs into her mouth and dry swallowing them down.
“See you in an hour,” the Dean said with a wicked grin.
“An hour?” Annie laughed. “With this stuff, more like 4.”
*   *   *
KNOCK KNOCK
   “Go away,” Jeff Winger shouted at whoever was knocking at the door into the Dean’s office that he had commandeered.
   “I’m coming in Jeff,” Annie said moments before she opened the door then did as Dean Pelton instructed by closing it behind her and latching the bolt.
   “Listen Annie, I’m sorry that I stormed out but...actually...I’m not apologizing. I was on set 12 hours for one scene…”
   “Shhh,” Annie said, placing her finger against his lips to get the much taller and older man to stop talking. “The Dean and I understand. Which is why I’m here.”
   Jeff didn’t understand what the younger girl meant but he was starting to put the clues together, especially when she used her hands on the armrest of his desk chair in order to spin him around so that he was sitting right in front of her now. This was the first time he really looked at Annie today and once again he was blown away by the 22 year old’s physical perfection. Though she was almost 20 years younger than him, Annie had developed a lot mentally since they had known each other, so much so that now he could masturbate to the image of her in his mind and not feel like a dirty old man.
   “Annie…” Jeff went to say before a finger against his lips stopped him once more.
   “You’ve been really patient about this hectic shoot so far,” Annie explained while she slowly lowered herself to her knees between Jeff’s legs. “And the Dean and I want to show our appreciation.” Annie continued while reaching up and undoing Jeff’s pants with practiced ease. “So please Jeff, will you let me show you how appreciative I am?”
   If several things were different then Jeff believed he could have turned down the offer from the much younger woman. Such as if she wasn’t already kneeling, or if her smooth hand wasn’t already encircling around his throbbing hard cock, or if when he looked down at here he didn’t flick between her big doey eyes and large tits which her blouse allowed ample cleavage to be shown. However, all those things were happening so Jeff felt powerless as he found his head nodding his consent to her question.
   “Good boy,” Annie said with a smirk that likely would have been better placed on her evil doppelgangers from a different timeline.
   Jeff was floored by the whole development of this situation so at this point nothing was left to surprise him. Well except for maybe how comfortable little Annie Edison seemed to be on her knees, staring up at him with her big eyes while she slowly, seductively stroked his fully erect cock. With one last wicked grin up at the ex-lawyer, Annie turned her gaze to the matter at hand as she leaned her head forwards.
   Jeff loved many things in life: a finely aged scotch, a perfectly cooked medium-rare steak, and above all else the first moment of a blowjob when the head of his cock became engulfed in a women’s warm, wet mouth with their lips closing snugly around his shaft. What made today even better, apart from the sleep-deprivation, was the fact that the mouth belonged to Annie Edison, a girl who started out cute-as-a-button 3 years ago when they first met and now was a fully developed (especially in the chest department) bon-a-fide hottie.
   “Jesus Annie,” Jeff groaned as the bookworm set about her task.
   Jeff would have bet the house (or condo in his case) that a blowjob from Annie would have been slow and tenatitive. While it had yet to reach neck-breaking speeds, the studious member of their study group was anything but apprehensive. In fact, as her head bobbed along the first 3 inches of his cock while her hand glided along the remaining 5 inches of his shaft, the sex act was being performed with the utmost professionalism. No better example showed this off was when Annie pulled her mouth from his tip, leaving a few small spit strings connecting his cock to her lips still, all so she could spit a little extra saliva onto his manhood so that her hand could glide smoother and faster.
   “I’m here to please,” Annie replied before lowering her head and taking him back in her mouth.
   And please she certainly did. First she kept at the same rhythm, establishing a solid base to work off of. Her technique was flawless and clean, despite the bookworm periodically pulling her lips from around his cock in order to either lightly spit on his shaft or to lick the sides or tender underbelly of his pole to apply saliva that way. Jeff preferred the licking method, a fact that didn’t escape Annie’s notice whether it be from the extra grunts from Jeff or the tightening of his fingertips against her bobbing head. Regardless, after 30 seconds of her sucking half his length, Annie would pull her mouth from him with an audible pop of the suction being broken in order to caress the entire length of his exceptional long cock with her skilled tongue.
   The girl was well and truly into her stride at this point, now combining several different moves. She still employed her smooth bobs along half his length while working her hand on the other half, and then she would switch to licking up and down his shaft several times, but she was evolving her technique as well. This was done by leaving her hand at the base to hold him steady so that as her lips descended they could go further than before. In fact, Jeff was surprised as he felt his bulbous head poke the back of Annie’s throat, and was further shocked as the studious college senior held him there for several seconds before she backed off, face now red from the lack of oxygen and thick strings roping between her mouth and his dick.
   “You’re incredible Annie,” Jeff managed to groan out after another impressive bout of sucking of his cock. “How’d you get this good?”
   “You may not like to sexualize me, but the others here in Greendale didn’t have such a problem,” the kneeling bookworm replied with a wicked grin.
   This time rather than build up to the deep throat technique, Annie went right back to it. Jeff had reached down to bundle up her silky dark hair and hold it out of the way so he could look down and watch as 3-quarters of his lengthy 8-inch cock disappeared into Annie’s hungry mouth. The small Dean’s office was filled with the noise of Annie gurgling on the shaft in her gullet, but to her credit she never once looked like gagging, even though she held it there for a good 10 seconds before surfacing.
   With thick ropes of spit adorning his veiny cock, Annie’s hand was like a blur as she adopted her initial pattern of blowjob once more. The only difference was the speed from both the handjob and her lips as her tiny fist and lips seemed to be rocketing up and down his manhood. And if that wasn’t enough, at random intervals Annie was press and hold as much of his cock in her mouth again, holding anywhere for 3 to 10 seconds before resuming her rapid blowjob.
   “Jesus Christ Annie,” Jeff groaned with what sounded to Annie like urgency. “Slow down or else…”
   “Just cum for me Jeff,” Annie assured him. “I want to taste you.”
   Jeff wished he would have lasted longer than the first time he hooked up with the gorgeous Annie, but it wasn’t meant to be. He could only hope that the next time, presuming there was a next time, that he could withhold more like his usual sexual stamina allowed, but then again he likely wouldn’t be sleep-deprived and driven half mad by the psychotic Dean.
   Despite what Jeff knew, Annie had given many a blowjobs by now at her time at Greendale and so fell into the rhythm of making him cum quickly. Which was to say she stopped varying her technique and instead focused on short bobs of her head and hand at a medium speed until he was busting a nut. Which, it so happened, was only 5 seconds in the future. With a final grunt of primal desire, Jeff reached his climax with the next heartbeat Annie felt her reward for her good work filling her mouth. Jeff pumped a healthy 6 strings of cum into her waiting mouth, pooling all along her tongue and allowing Annie to savor the taste of Jeff Winger’s semen, which was mostly salty but with a touch of sweetness, making it rather palatable.
   Jeff was thankful when Annie’s bobbing and stroking slowed before ultimately stopping, her lips being pulled from his slick cock though her hand remained holding his pecker. Knowing he was looking down at her, Annie gave him a little show by opening her mouth and revealing the large mouthful of gooey white cum in contained. Giving the thick fluid a little gurgle, Annie closed her lips and did an exaggerated swallow, taking it all down into her stomach before opening her mouth back up to show Jeff that she was a good girl and eat every last morsel of his cum.
   “Holy crap,” Jeff huffed, torn between feeling more pleased and surprised by the turn of events. “I can’t believe that finally happened.”
   “Maybe it can happen again,” Annie said with a wry smile, her hand starting to stroke the dick in her hand lightly, halting it from going flaccid.
   “Oh?” Jeff asked, lifting a single eyebrow. “What did you have in mind?”
   “Well I want to keep you in character and the Dean gave me very particular instructions about what he liked.” Annie commented, feeling his dick getting a little more erect.
   “And what did he say?” the tall ex-lawyer probed, his interest well and truly sparked.
   “He said he really likes blowjobs,” Annie answered, making her point by leaning in and giving Jeff’s cock a lick, sucking up the drop of cum that she didn’t manage to suck out moments before. “But he loves anal sex.”
   “God bless you Dean,” Jeff thought as his cock sprang to full life once more. “Well, I’d hate to disappoint Craig and give a shitty performance for his commercial by not being deep enough in character.”
   “No! That can’t happen with his genius vision,” Annie shouted with the single minded purpose that only Adderall gave her, which was also why her blowjob was so perfectly performed.
   “Then let’s give the Dean, and me, what is required,” Jeff said with a smile he couldn’t hide even if he wanted to.
   As Annie got to her feet, she decided to give him a look at what most men would die to see from her. For the past 3 years that Annie had been at Greendale, she was no stranger to showing off her amazing tits with a number of low cut shirts, blouses or dresses. In fact, her tits alone was why Greendale was seeing an enrollment boom due to word-of-mouth and several social media pictures taken of Annie’s legendary cleavage that had gone viral. And now, Jeff Winger was finally privy to looking at them in the flesh as Annie pulled the straps from her shoulder and pushed down both her top and bra to bunch around her flat stomach.
   “Oh. Dear. Lord,” was all the experienced ex-lawyer could get out at his first sighting of her majestic breasts.
   Jeff was tried not to sexual Annie over the last few years but he was only human at the end of the day, thus had taken more than his fair share of glances down her low cut tops. Therefore he knew that the nerdy girl possessed a pair of tits that had few rivals, but that wasn’t enough to prepare him for their heavenly appearance. Large and well rounded, with eached capped by a perfectly sized pink nipple, Annie’s tits hung before her proudly, suspended without even a hint of sag that only someone in their early 20s could have.
   “And the big fella roars back to life,” Annie commented, referring to the rock hard cock sprouting from Jeff’s lap.
   “Need to fuck you. Immediately,” Jeff demanded.
   “Yes sir,” Annie cooed with a grin.
   Jeff went to stand but a small hand against his sculpted chest kept his ass firmly planted in the Dean’s leather desk chair. Annie had already decided on a plan of action of how she wanted to take her first cock in her ass, which involved the tall man sitting and her with the control. Knowing it would sting some, as Annie turned her back to Jeff and started to back up towards his lap, the bookworm pulled another two pills from the small bottle Star-Burns had provided her and suddenly all her worries and anxiety melted away.
   “Ah, that’s better,” she commented quietly.
   “What’s that?” Jeff asked, not able to make out what she had said.
   “I said just go slow and let me ease things in,” the bookworm retorted, lowering her ass until his tip was against her asshole.
   “Of course. Let’s take things...oh fuck that’s tight,” Jeff gasped, for at that moment his tip was pressed past her sphincter and buried in the first 2 inches of Annie Edison’s rectum.
   “Oh! You’re telling me,” Annie replied, pausing at that point to grow used to the feeling of having her virgin asshole shoved wide open.
   Though she had never taken a dick up her ass before, Annie had been prepped for this moment by a couple of other dates over the last year who enjoyed sticking a finger of her butt. While nowhere as big as Jeff’s healthy-sized cock, it thought the studious girl a number of things about her body, such as relaxing made her sphincter expand easier. The fact that the Adderall was starting to cause a firework show up in her brain at this very moment also helped considerably.
   Jeff was going to be as patient as needed since he was getting a chance to sodomize such a fresh-faced hottie. Much to his surprise though, after only a few breathes little Annie Edison began moving up and down his cock. Not in large motions, but she was pushing down an extra inch of his veiny cock before riding up so only his purple-colored tip remained implanted in her booty.
   As Jeff started to grunt due to the tight seal riding up and down his cock, his gaze got caught on a small orange bottle that must have spilled from the riding girl’s pocket. Unable to stop himself, Jeff questioned the girl he was currently ass-fucking. “Is that adderall?”
   Jeff noticed an interesting thing when he mentioned adderall to Annie. For the booksmart girl, the drug commonly associated with intense studying was a hot-button issue for her since an addiction to adderall made Annie snap back in high school. She went a little crazy in all departments and needed to be hospitalized, making her lose her academic scholarship to all reputable colleges and universities, thus making her end up at Greendale. It also made her lose her virginity and became the slut of her high school as well, a fact Annie rarely talked about. Nonetheless, when Jess mentioned adderall he noticed that Annie immediately started riding him a little faster and deeper, which in turn made her moan in pleasure.
“What was that name they called you in high school?” Jeff asked as the younger girl bounced her asshole along half his length. “Annie Adderall?”
Jeff was testing his hypothesis and wouldn’t you know, he was correct. With a grunt of frustration Annie rode her impeccable tight ass a little further down his cock, taking more than half inside her rectum now. She was also showing much less restraint, as somehow the anger of her past was fueling her colon to relax and accept more dick or the rage was just blunting the pain sensation from making it up to her brain.
“Ugh! Don’t call...ugh...me that,” Annie huffed while going even faster now.
“Call you what? Annie Adderall?” Jeff asked, purposefully provoking her and immediately feeling the reward of having a previous untouched part of his cock suddenly enter the bookworm’s backdoor. “Was is Adderall Annie instead?”
And with that final mention of her nickname from the past, Annie thundered her petite but still bubbly ass all the way down so her cheeks landed in Jeff’s lap. Jeff couldn’t help but feel a shudder of pleasure course through the entirety of his body as innocent Annie Edison rested with all 8 inches of his thick cock stuffed up her asshole. When the gorgeous 22 year old planted her feet on the ground and propelled herself up, Jeff audibly moaned as he felt the elasticity of her backdoor grip his manhood along the entire length before she reached the top, reversing course at this time to crash back into his lap once more.
“Adderall,” Jeff grunted, rewarded with the faster stroke of her anal sphincter on his cock. “Annie.” Once more she thundered down against his lap. “Adderall.” This time Jeff could hear the snarl escape her lips as he reminded her of the darkest time in her life. “Annie.” Again she threw herself down his cock, taking him balls deep.
Jeff realized he may have created a monster with the name calling but since the genie was out of its bottle, he may as well take advantage. His hands weren’t needed on her hips anymore to help guide her so instead they shot a few feet higher in order to corral her massively swaying tits in his grasp. Firm, large and bouncing in front of her like only those of a 20 year old can, Jeff kneaded the heavy tits like his life depended on it, even rolling her silver dollar-sized nipples between his thumb and forefinger to keep them hard. However, after another minute of the intense riding, Jeff was unable to handle anymore given the familiar tingling his balls were sending up to his brain.
Jeff couldn’t take anymore of the constant riding of his dick by Annie’s extremely tight but accommodating asshole. In fact, the only reason he lasted this long was because of the surprisingly expert blowjob that the nerdy girl had given him right before she begged him to butt fuck her. However, all good things must come to an end, including the sodomy of Annie Edison. But Jeff needed to go out with more of a bang, so to speak, really driving himself past the edge of his climax. He needed to fuck Annie harder, faster and with more intensity, which meant a change in position.
Wanting to fuck the innocent-seeming Annie doggy style, Jeff waited until the dark-haired girl rode to the top of his cock again before crashing back down onto his lap. This time, instead of encouraging her upward flight along his shaft with his hands on her hips, Jeff clutched her against him as he used his powerful legs to propel himself from the Dean’s chair. With them both on their feet, Jeff continued his swift re-positioning by spinning them around and bending Annie down at the waist so her ample tits were pressed against the wooden desk with the much taller man standing fully erect behind her, dick still firmly in her once-tight asshole.
“Oh Jeff!” Annie cooed with the sudden movement.
Whereas the sodomy at the beginning of this tryst was tender and somewhat slow, the thrusting into Annie’s backdoor was anything but now. Instead, their lovemaking had a much more feral intensity to it, with Jeff’s powerful strokes into Annie’s ass only matched by the dark haired girl pushing her booty backwards to met his hips.
“Oh my God, Annie!” Jeff grunted, lost in his primal need to cum, which was nearing.
“I know! Just a little more! That dick feels so good in my little ass,” Annie encouraged, surprising Jeff with how she too was on the verge of an orgasm.
Jeff has half a mind to slow down and gaurentee that Annie get to orgasm, but it seemed like the bookworm was getting off on the hard ass-fucking so he continued on. The busty girl felt his large hands tighten further onto her womanly hips and somehow his thrusting got faster, something she didn’t think possible.
“So soon,” Annie screamed, on the verge.
“Quick. Play with your clit,” Jeff demanded. Though normally selfish, Jeff wanted the younger girl to cum as well for all her good work tonight.
“Oh dear God!” Annie said, summiting her climax after a few seconds of rubbing her clit as Jeff instructed. “Now cum for me in my little ass.”
Jeff needed no help in that department since the moment Annie came, his was practically on its heels. With several last hard thrusts, Jeff threw back his head and roared in primal delight. Annie felt his thrusts slow to a crawl at that point, still pumping into her backdoor but with none of the zeal as moments before. That’s when the bookworm felt splash after splash of Jeff’s cum painting the inside of her bowels, a sensation that almost made her cum again mere seconds after creaming herself.
“Fuck me,” Jeff groaned, head hanging low as the unloading of his second deposit of semen into one of Annie Edison’s holes had depleted him of all energy.
“Actually, I think you fucked me,” Annie corrected, drawing a little giggle from both of them.
Jeff held his cock in her tight little ass for another minute before summoning the last of his reserves and pulled his slowly deflating tool out. It left them both feeling somewhat disappointed, but they both took solace in the fact that finally the sexual barrier was broken between them. And based on the chemistry they had in the Dean’s office while exhausted to the point of psychosis, they both figured it would only be better from here.
- 1
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Annie Edison: Script Supervisor