Disclaimer: I do not own Community nor any of its characters, specifically Annie Edison and Jeff Winger. I make no money from this fan fiction

Summary: Evil Abed finds a way to get out of his timeline and into one from the night the timeline branched. First goal is sending Jeff to mess with the group.

Pairing: Annie Edison/Darkest Timeline Jeff

Codes: MF, Anal, Oral

Community: Revenge From The Darkest Timeline Part 1
by The Chemist

"Excellent, we are almost ready darkest gang," Evil Annie shared.

"This arm feels like my original," Evil Jeff commented, flexing his fingers to accentuate his point.

"It better. It ate up a good deal of Pierce's inheritance," Britta replied.

"Yeah I'm still not 100% sure why or how we got Pierce's estates and money when he died...but that leg infection was the best thing to ever happen to us in the darkest timeline," Troy shared through his synthetic voice box.

"And you know the plan," drunk Shirley asked with a slur.

"Of course. Get to the original timeline and fuck up their lives," Jeff answered. "Is the room ready Abed?"

"Yes. Now I'll warn you, the machine room is a work of art but it can't be as exact as we'd like. There are literally an infinite amount of timelines, however, I have calibrated for it to find one of the 6 timelines that diverted from that night," the goatee wearing man answered.

"But that's only, like a 30% chance of it being the original timeline," Britta sulked.

"You really Britta'd that math," Annie answered, her crazed eyes wild.

"Okay Jeff, it's time," Evil Abed said.

The two men walked away from the rest of the darkest timeline group and entered into what was Abed and Troy's Dreamatorium. The evil version of the pop culture expert had converted the room for the past 2 years into what would suit his purposes. It took time and considerable energy, but Evil Abed was determined and finally he found a way to slip a person from one timeline into another, specifically from that fateful night.

"Is there anything else I need to know Abed," Jeff asked, still getting use to having his arm back.

"Pretty self explanatory. You'll have all your memories from our timeline but be placed into a different stream. Tried to blend with the group but above all else, mess with them. Your goal is to make their timeline darker so the rest of us can come across. Punish them for causing us to rot in our version of time," Abed explained.

"Didn't need reminding on that last point," Jeff told him.

"We'll try following behind you but the room will need time to recharge," he added.

"What if I see my...other self," Jeff asked.

"Nothing will happen. It won't break the time-space continuum or any other crap like that. But it will ruin all our plans so try to make sure you're not seen by him," Abed finished.

"Great. Let's do it then," the blonde stated.

Evil Jeff watched as his friend went over to the closet, which had been converted into the controls for the room. He didn't know what he was doing, only that he was pulling this, twisting that and making sound effects with his mouth. It had been minutes since he had left and Jeff was about to ask what was taking so long when suddenly he felt funny.

"Um Abed...I think something is happening..."

There was no reply. Jeff tried closing his eyes and blocking out the anguish he was feeling but it didn't help. He felt nausea wash over him as though he was about to hack up his lunch, but luckily he did not. He opened his eyes to address his friend again, but everything was different now.

It took dark Jeff a few moments to get use to his surroundings but Evil Abed had done it, he had sent him into a different stream of time. Looking around, he was in the hallway of his condo building, key in hand. However, before he put it in the door slot, he heard the elevator dinge behind him. Ducking into a hallway behind him, the handsome man watched as an exact replica of himself emerged from the doors.

This version of himself was smiling and happy, something that darkest timeline Jeff hadn't done since that night. Dark Jeff had visions of flames and blood spark through his mind, but with a shake of the head, the only thing that remained were feelings of anger, which he would use. Determined to get back at their happier selves, dark Jeff balled his fist and approached himself from behind.

The carefree version of himself never saw the punch coming as it struck him in the back of the head, rendering him unconscious right away. Remembering his supplies from the transportation, he used the rope and duct tape to bind his hands and mouth before fitting him down the garbage chute without anyone seeing him.

"Now, let's see how he's been living," Jeff said to himself.

Using his key, the darkest timeline version unlocked the door and pushed it open. So far the set-up of the condo wasn't exactly like it was before that night, as it was...well more lived in. There was more personality and color, less like the sterile-looking place he kept in his past.

"Babe! I'm in here," a familiar female voice rang out.

"What...are you doing," he asked, trying to act normal.

"I'm running the bath."

Annie's smiling face greeted him as he entered the open doorway of the washroom.Apparently in this timeline, not the original timeline he sought but another from that night, the brunette and himself were an item. Or at least he believed they were, or why else would she be here without him, about to have a bath...and standing to give him a quick kiss on the lips.

"Oh...ok," he replied, more than a little stunned.

The cheerful Annie wore her shiny brown hair down over her shoulders, looking adorable yet sexy all at the same time. She was in athletic clothes, a tight-fitting aqua tanktop and an even tighter pair of short red shorts, looking as though she came straight from working out. His version of Annie was driving crazy from the fire that night, looking feral and never having the thought of going to a gym.

"Anything wrong? You seem a little off," Annie asked, scrunching up her face.

"Just curious if there was room for me in there," Jeff replied, thinking of something her version of the man would have said.

"Stop it Jeff, you're so bad," she said with a smile and a playful slap to his chest.

"So is that a no then," he asked, channeling his former smooth self.

"Well...after my bath," she blushed, returning to her seated position on the edge of the tub as the water filled. "But while you're here, one of the jets isn't working."

"Really? Which one," he replied, not knowing if this was something he had fixed in front of her in the past, thus about to give away his secret.

"This one, in the back," Annie reached to the opposite side of the white tub.

Thinking quickly, a perfect mini plan popped into Jeff's mind at that moment. He wanted to dodge the question and any repair he may need to perform on the broken jet in case she had seen him do it in the past. With Annie reaching her arm over the water, Jeff sprang and pushed the curvy girl into the mostly filled bath.

"Are you kidding me! Babe!"

Annie was still smiling and laughing, despite the fact that she was now soaked from the neck down. She had managed to keep her head and shoulders above the water but nothing else. Jeff laughed as well, the dodged her attempt at flicking the bath water at him.

"Come on, that was hilarious," he pointed out as the shared in laughing.

"You're just lucky these clothes were already dirty," Annie said, still standing in the pool of water.

"Well you're a dirty girl so the clothes are perfect for you," he replied, his darker timeline personality coming through a bit.

"Pass me a towel at least you naughty boy," Annie answered.

Jeff reached behind him and found a large white towel then tossed it to the pretty brunette. As she talked about how her bum had gotten a little sore from the unexpected landing, Jeff couldn't help but gaze over her body. Her large tits looked even more amazing pressed together tightly in her spandex shirt, a massive mound of cleavage formed plus the cold water made her nipples hard.

Of course, the girl's beautiful face and amazing tits weren't the only thing she had to offer. Though usually hidden under sun dresses that she loved to wear, Annie rocked a solid caboose out back, it being plump and round. The kids these days called it a bubble butt, but all Jeff knew about it was that it was a grade A behind.

"I can't apologize for making you all wet," he said with a wink.

"You're so bad," Annie faked anger. "I knew you were gonna make a comment like that."

"Good. So this version of Jeff and Annie are a little dirty," dark Jeff thought. "Since you fell, pull down the shorts and let me look for a bruise."

"I know what you're doing Mr. Winger...but I guess I can give you a little show," Annie answered playfully.

Jeff simply smiled widely at his placement in this timeline, as he was going to do everything in his power to give this happier and saner version of Annie Edison the pounding of her lifetime. His thought was interrupted when the beautiful coed turned her back to him and pulled down her shorts over her rounded ass.

"Mhmm," he moaned, seeing her thick cheeks separated by only the thin strip of her white thong.

"Jeff," she said in hushed tones. "Are you washing me?"

She already knew the answer, how could she not as a cloth was rubbing over the exposed skin of her ass and it was clearly not by her own power. Jeff couldn't help himself, running the cloth rag over her sunkissed skin. Her legs were thick but very feminine, and her ass was just as round and nice to touch as it looked.

"Ms. Edison...what's that hand doing," Jeff smirked, observing that it had slid into the front of her shorts.

"Oh I think you know," she said.

When Annie turned around, her arm had pulled the waistband of her shorts down so that it gave him a view of the bare skin right above her pussy. It didn't look like she was fingering herself, just in the middle of trying before she had spun to face him. He didn't know which timeline he was in, but he was hating the version of Jeff that got to occupy it here with this more sexually liberated version of Annie Edison.

"God you have me so horny now," Jeff told her. "Let's take this to the bedroom.

"Let's go then," she answered in more serious tone.

Jeff watched her as she stepped out from the bathtub, giving her his hand to make sure she didn't slip. As she quickly dried off her legs and lower body, the handsome man from the other timeline reached across and shut off the running water. When he turned back to her, she was leaving the room, him right behind her.

"Mhmm...I missed you," she said, turning to face him when they got into the bedroom.

She leaned into him, pressing her full lips against his slightly surprised mouth. He recovered quickly and gladly returned the kiss, taking the moment to appreciate her. For him, he hadn't had his lips against hers, nor his tongue thrusting into her mouth, since the night at the end of first year, nearly 3 years ago now.

"Whoa," he grunted, finding himself pushed onto the bed.

Annie didn't give him time to recover, flashing him her adorable smile before climbing on top of the mattress, and him in the process. She crawled up his body to have her legs straddling his hips, sitting her plump ass down right on his crotch. Instantly his cock began to stiffen, but her focus was more on his hands reaching up to fondle her rack.

"Such a boob man," she groaned, his hands roughly kneading her.

"Don't worry baby, I'll get to this as well."

To drive his point home Jeff lowered one hand, leaving the other to continue massaging her great tits, and pulled down her shorts as much as they would go. Her pussy was everything he was hoping it would be as he looked at it, bright pink, hairless and already glistening with wetness. Just to confirm his visual inspection, Jeff dipped two fingers into her hole, feeling the velvety walls grip him tightly but still allow him to slip inside.

"Ohh...awwhh," Annie screamed.

"Here, taste now," Jeff said, seeing how she reacted.

With only a slight hesitation to the somewhat odd request from her boyfriend, Annie seized his wrist with her hands as he brought the digits towards her face. Guiding them the rest of the way, the brunette parted her lips and placed his two fingers into her mouth, sucking on them and tasting her sweet juices in the process.

"Tell me how horny you are," he demanded.

"So horny," she moaned.

"Then let's do something about that," Jeff retorted. "Get those clothes off."

Annie grinned at him before rocking back onto the soles of her feet and getting into a standing position. Jeff tucked his arms behind his head like a pillow to prop up, watching as Annie pulled her tight shorts off her full ass and great legs before tossing it aside. She made similar short work of her aqua tank, but she only teased pulling off her underwear instead of actually removing them.

"Had something else in mind first," her eyes flashing down to his tented pants.

"Then get that mouth to good use," he told her sternly. "And show me how dirty you can be."

Annie only gave him that look she used to portray boldness and yet some disbelief but Jeff knew that his actions weren't yet making her suspicious. He was correct and watched as the brunette sank herself low, her large, still covered chest resting on the mattress while behind her the plump ass he loved so much was still visible. She even gave it a sway for him all while taking his right nut between her lips and sucking on the oval.

Some girls may have backed away and avoided sucking on balls as best they could but this timeline of Annie was not one of those girls. Jeff was soon learning that this version of the girl was much more of a sexual freak then original Annie had been, though yet to prove she was as sexually charged as the one from his dark timeline.

"I seem to remember you like when I go to town on these fellas," Annie said with confidence.

The coed managed a quick smile up at him while she traded on of his nuts in her mouth for the other. Pulling deep with suction, Jeff groaned as a result as Annie seemed to thrive on massaging his tender balls with her tongue. Looking down between his legs, the one-time armless man could see as the as the girl with the adorable face pulled his nut with her mouth, stretching the sack in the process.

Annie loved how she had the bigger man in the palm of her hand, making him groan and wiggle about on the bed they shared for most of the past 2 years. She could tell that Jeff was slightly upset when she stopped playing with his very full sack, but she knew he would prefer it more in a moment.

She bent down even lower to run her tongue along the main vein running on the underside of his massive cock, which was resting on his ripped stomach. Her hand closed around the base when she neared the top, angling it upwards to suck on the tip before descending lower. She bobbed on the first several inches, swirling her skilled tongue at his pee slit when she reached the top to elicit extra groans from the muscular man.

"Tell me how much you like my cock," he said, a hand holding her shiny brown hair atop her head.

"Your dick is nice and hard," she commented before swallowing half his length.

Evil Jeff could only grunt his approval as the curvy brunette continuously sank and rose on his member, taking 5 inches between her lips at a time before coming to have only the tip remain inside her wet mouth. Whatever she couldn't get in her mouth, Annie would use her hand to stroke, working in perfect unity with her mouth.

Annie had learnt that variety was the key to a truly great blowjob so she took her own advice. After bouncing her mouth on his cock for upwards of 30 seconds, she would slow it right down and force as much cock between her plump as she could, suppressing her gag reflex in the process to swallow 7 inches.

"Glllcckkk," she coughed before repeating the feat.

"Fuck," Evil Jeff swore.

Pulling him out to get a quick lungful of oxygen, Annie went back to her quicker pace but taking only half his length in her mouth. Her hand worked with her mouth, but after another half minute she stopped that to run her tongue from his tip down to his base, first on one side of his wet cock then the other.

Her mouth on his cock felt better then he had ever dreamed of it in his own timeline. Her mouth was so wet and surprisingly skilled. He imagined that the Jeff in this timeline loved blowjobs as much he did, so likely began to mould Annie into a cock-sucking champion to suit him. Apparently she had been receptive to his intentions and now dark Jeff was on the receiving end.

However, the drawback was that she was also pushing him towards cumming. He had fucked girls regularly in his own timeline, but not at the frequency he would have liked. After all, it had been nearly 2 weeks since he ruthlessly sodomized Britta, the blonde loving every minute of it, but that did give him an idea.

Licking his middle finger and spitting lots of saliva onto the tip, Jeff got into more of a seated position while Annie's mouth continued ascending and descending his cock. Sliding under her thong, Jeff didn't go down to her pussy like she was probably thinking, but instead rubbed the spit around right on her puckered asshole.

It was a risk, a calculated one but a risk all the same. Maybe this version of Jeff and Annie had a talk about anal play in the past and it was an absolute dealbreaker. However, he was hoping they hadn't and that worst case would be an interruption of the blowjob, maybe a scolding then they'd get back to it except he would have had a break and not cum too early.

"You gonna let me play with your asshole," he asked.

"Yeah," she answered with a toothy smile, popping up to look at him from sucking on his dick.

"Well fuck," Jeff thought, realizing that it was probably something she'd been thinking of for awhile now. "Then bend over."

Jeff wasn't happy to not have her skilled mouth bobbing on his cock any longer but after 5 minutes he needed the break and this was the best way possible for him to have it. Annie got immediately onto her hands and knees and Jeff was behind her in an instance, pulling her thong to the side to give him a full view of her pussy and her tightly constricted asshole.

"Careful," she said, with the faintest amount of worry.

Jeff didn't bother to reply, instead he had his laser-like focus set on one thing and one thing only. Pushing a great deal of his saliva onto his finger, he brought it into Annie's crack and smeared it directly over top of the girl's crinkled asshole. She jerked slightly with the contact, but Jeff was prepared and didn't let it affect his concentration.

He didn't push it too much right away, instead he did small circles of her asshole without dipping inside. With each pass around her hole she seemed to loosen up more and more, realizing that it wasn't painful and actually was making her feel...curious to say the least.

"I'm gonna put my finger in now," Jeff warned

Annie turned around to look at him, giving him a warm and brave smile as she nodded her head. She watched as he spat a glob directly onto her asshole before his finger went back to working the fluid into the muscular ring.

"Ugh," she groaned as the first inch of his middle finger dipped into her rear.

"Good and tight," Jeff observed. "Mhmm...and warm."

Annie smiled at he updated her, all while Jeff's finger venturing deeper inside. For Annie, it didn't hurt as his finger was well lubricated and he didn't push her. However, he was continuously pushing in and out of her rear, able to fit the whole digit into her ass without difficulty.

"Awww...mhmmm....oohhh," Annie moaned. as her finger was worked in and out of her virgin hole.

"God that's sexy," Jeff said, practically drooling with a raging hard-on.

"Suck me off again," he demanded, changing gears again.

Annie was obedient as ever and spun around to face him once more. Dark Jeff groaned in pleasure as the horny and eager to please coed tilted his cock up and popped his nuts back in her mouth, doing one at a time. They made an audible noise as she sucked on them before spitting them out so she could use her skilled tongue to lick up his mighty shaft before taking his head back into her mouth.

Jeff from the darkest timeline was thoroughly enjoying the blowjob that this version of Annie was doing. He reminded him a lot of the Annie that would have happened if not for the fateful night years before, a lot more innocent and a hell of a lot more sane then the one in his timeline.

"Wow...getting so much friskier today," Annie commented after Jeff thrust his hips up towards her face.

Jeff only smiled but felt confident that he wasn't pushing her boundaries too much. In fact, she seemed to be game to everything so far, including taking his middle finger knuckle deep inside her virgin asshole. Testing her out more, Jeff went back to thrusting his hips up into her mouth again, his spear getting to the back of her throat as she sucked him off noisily.

"Now let that spit fall on my cock," Jeff told her.

"Like this," she asked as the thick drool string dropped onto his tip.

"Now push it down with your lips," Jeff said as she bobbed down several times, pushing her drool down further. "Now lick it up."

The saliva was down to the side of his shaft, and with eager eyes he watched Annie slide her tongue down his pole. Before licking over the thick string, Annie opened her mouth and wrapped her lips around that part of his cock, slurping up the spit and ending with a kiss. Being so close to his balls, the brunette moved lower and took turns with each round structure in her mouth before returning up.

"Can we..." Annie asked, eyes flashing down to her sex.

Jeff nodded and watched as the horny brunette got to her feet once again. She hooked her fingers into the waistband of her thong and pulled the white undergarments off her body. He smiled at her as she went back to her knees, this time straddling his waist then sank deeper. Jeff had lined up his saliva-drenched cock with her pussy, and even though she was remarkably tight, her pink folds engulfed him.

Dark Jeff had fucked Dark Annie many times in his timeline but getting to have sex with innocent Annie Edison from the best timeline was special. He thought about savoring the moment but his animalistic side kicked in. By the time she rode him to his base he was already lifting her back up so that she could fall down his whole length once more.

"Need you tits out," Jeff demanded.

She used one hand on his chest to steady herself as she rose and crashed down on his thick pecker while her other arm snaked behind her back and undid her bra. She throw it aside and he watched as her long brown hair flowed down to frame the greatest pair of tits he'd ever encountered. Large, perfectly round and not even the suggestion of sag, they were the stuff of legend...and all his.

"You have the most impeccable set of tits I've ever seen," he told the younger woman 15 years his junior. "And I think that every time I see her huge cannons."

"Mmmm," Annie moaned again as he graze over one of her sensitive nipples. "Thank you."

Needing to suck on her great tits immediately Jeff bent her towards him while crunching his abs to meet her halfway. The position was favorable as it allowed him more control to drive his hips relentlessly up into her snatch while his head was buried in her cleavage. Rotating his neck to one side he enclosed her nipple between his lips and sucked hard.

Annie moaned again, whether due to his fiendish pace slamming his cock into her pussy or his oral assault on her boobs he didn't know or care. He freed that nipple and replaced it with the other and give it the same treatment as Annie arched her back to offer her pillowy tits more to him to do as he wished.

"Ugghh," she nearly screamed out in pleasure as he played with her sensitive breasts.

Jeff straightened her back up while he groped and kneaded the heavy and large C-cup sized tits for quite some time while making her do more of the riding. However, as good as this timeline's Annie felt around his cock with her pink folds, Jeff had another hole in mind for the sweet girl.

Still leaving one hand to grope her big breasts, the older man moved the other down her flat stomach until he found the top of her slit. More specifically he was after her clit, which in his Darker timeline never ceased to make the girl cream herself in record time. Pushing her to lean back even further, it really opened her sex to him, allowing them both to crash to meet each other as she took it harder and harder from her dream man.

"Oh my God Jeff...if you don't stop I'm gonna cum," she warned through moans.

"Cum for me," Jeff demanded.

The apartment was filled with the sounds of Annie's panting and the sloppy, squishing sounds that happened as Jeff's cock flew at record speeds into her very wet twat. The repeated thud of flesh on flesh reverberated around the walls of the bedroom as well as he fucked her harder and rubbed faster, determined to get the pretty girl off as soon as possible.

"Oohhhh....yesssss....ugghhhhhh," she screamed at the top of her lungs as she had another intense orgasm brought on by her usual partner albeit from a different timeline.

Jeff bit his lip and rode out her orgasm as her pusyy clamped down on his cock in an effort to milk him of his seed. On a different day or universe it would have worked, but Evil Jeff had his mind set on anal fucking the brunette to help make this timeline darker, starting with putting it in her brown eye.

"Go on your knees," Jeff instructed.

Annie couldn't believe how quickly she had cum and would have been embarrassed by it but she didn't have time for that. Acting with haste, the brunette was eager to listen to her man and did as she was told. Rolling onto her stomach, she lifted up onto all fours like instructed.

"Like this," she asked, looking back over her shoulder.

Evil Jeff didn't answer instead he got his hands onto her ass and was sure to cover every inch of her booty with his touch, his fingertips gliding over the curved surface while he licked his lips in anticipation. Her tushy was perfect and felt so smooth under his touch. He was going to have to make sure he tempered himself when he finally got inside her and didn't cum too quickly though that was probably a pipe dream after barely surviving her active riding earlier.

"I'm gonna stick my finger in your ass now," he told her.

"Mhmm," she moaned her consent.

Annie wiggled for him and was enjoying herself so he upped the ante by taking a hand from her ass towards his head before he took his index finger straight from his mouth to her brown eye. She was ready for him this time and barely flinched as he rubbed her crinkled starfish, though she did moan in actual pleasure as he inserted his digit into her asshole up to the knuckle.

As he slowly moved his finger in and out of the busty brunette, Jeff waited for her to relax a little more and when that happened he buried the length of his finger in her ass. She yelp in some discomfort but he didn't allow her to focus on it as he pulled back, added a second finger and pushed that into her asshole now as well.

She groaned in more discomfort as her sphincter was spread further then ever before in her life but surprised herself and the evil Jeff when she moaned 'yes' after a short time. Buoyed by her enjoyment of being finger banged in the ass, jeff bent down and spit directly into her gaped hole before plowing the digits back inside her to loosen her up further.

"Such a champ," Jeff grinned.

"Oh my God," Annie said, running a hand through her dark hair.

"That's it Annie. Now you stick a finger in your ass," Jeff told her.

Annie didn't have time to think as Jeff seized her wrist of the hand she wasn't using to hold herself up and pulled it behind her. When her hand touched her curvy ass, Annie went into autopilot and did as she was told. Extending out her middle finger, she pressed it against the center of her backdoor and pushed in, feeling the tightness of her backdoor for the first time ever.

"Mhmm...awhh," she moaned around biting her bottom lip.

Annie had never even pleasured herself in her twat let alone fingered her asshole before yet here she was doing it for the man she loved. She had no idea that this wasn't the real Jeff but that didn't matter to the evil version. He watched the girl with the perky ass continuously slid her finger in and out of her asshole because he told her to, but he couldn't wait any longer.

"I'm gonna stick it in now, okay," he asked, though sounding more like a statement.

"Yeah...okay," Annie groaned, drugged in her post-orgasm bliss still.

"Here we go," he said hungrily.

"Oh My God," she swore as his tip pierced inside.

Darkest timeline Jeff didn't hesitate further as he pushed forward firmly yet without malice. The combination of the wetness of his shaft, relaxed attitude of Annie and how he had loosened her with his fingers had helped significantly. The adorable coed still grunted as his tip disappeared into her dirt road, but it was minimal with all things considered.

This not being his first time sodomizing someone, Jeff knew the proper thing to do was wait for Annie to make the next move, which luckily happened in short order. No sooner had he penetrated her bowels was when the girl 15 years his junior leaned her weight backwards to take the next few inches into her booty.

"Fucking tight," he grunted.

With her seal of approval achieved, Jeff took control back. With two hands now holding onto her hips to still her motion, the lanky man began making more progress into the depths of her anus. Though it was slow he didn't mind as his small strokes kept getting more of his fat cock inside her.

Always thinking of more, Jeff started to push more inside and go faster almost at the same time. This caused the curvy brunette to groan more and he noted the pillars of muscle running up her spine tighten. He figured that it may be too much too sooner so he slowed his thrusting down but kept it so that it was three-quarters of his length sliding in and out of her ass.

"This is how you like it in your bum," he told her confidently.

"Yeah...just like that," she replied in a soft tone. "I like that."

"You like my big cock in your tiny asshole," he asked grinning widely.

"I really do," Candace smiled.

Annie was telling a white lie but she always liked to please Jeff so if he wanted to fuck her ass and it didn't hurt too much then there was no harm in that. She told him what he wanted to hear and continued clawing the bed sheets as his thrusting slowly got faster and deeper into her virgin asshole.

"You wanna go faster now? Ohh...yeah. Fast feels good now, doesn't it slut," Jeff told her while he degraded Annie.

Even with 6 inches of his shaft continuously knifing into her ass, Annie continued to voice her satisfaction which became muffled when she began biting the blanket beneath her. Over and over again her expansive asshole stretched to what had to be her limit in order to accommodate his eager probing. The smile on her face and the way she looked up at him while he drilled into her only helped to elevate the lust he felt for the submissive girl, and also made him think how sweet it was to corrupt her so completely.

If she was in pain from the relentless ass fucking he was doling out to her, Evil Jeff could never have known it. With each time the full length of his cock slid out of her bowels only to pierce them once more until he was balls deep, she moaned. In fact, as she bit the flannel blanket on top of the bed, the studious girl demandingly urged him to keep fucking her ass without words.

As he held steadfast onto the curves of her hips where her narrow waist bellowed out to create the great curves, she wiggled her booty enticingly for him. He took up the invitation each time by rearing back before spiking her on his spear in her rectum without fail. Well he was until in one swift motion he pulled back and completely vacated her ass with an audible pop as the seal was broken.

"Suck on it now," Jeff instructed.

Annie started to move and was soon aided by Jeff who rolled the beautiful student onto her back as he kneeled over top of her chest. His cock protruded out from his hips and was nearly smacking her in the face, standing directly in front of her mouth.

Annie started to open her mouth and getting her face lined back up with his cock before something went off in her brain. "Wait, that just came from..."

"I know. Do it," he ordered, his darker personality bubbling more to the surface.

The sternness in his voice shocked Annie, as did much of his actions this day but the submissive girl only ever wanted to please the man she was so happy to have landed. Forcing the gross image of where his dick had just been, Annie opened wide and allowed Jeff to put his throbbing cock into her mouth, straight from her own asshole.

The taste wasn't too bad, her imagination the worse offender. In reality it had an odd flavor to it that was neither bad nor good. She bobbed her head on his length, forcing herself to take more of his rod into her mouth as he wanted.

"Spit on it. It's going back in your ass so get it all wet," Jeff told her.

Annie did as she was told once more, gathering her spit in her mouth then spilling the saliva onto his eager cock. This time when he returned himself to her mouth he grabbed the back of her head and he directed how much and how fast he crammed into her. He got forceful at times and pushed too far, making the submissive coed gag and spit more up on his manhood, though it would help when he sodomized her again.

Seeing the innocent looking coed subjecting herself to his every dirty desire made the need to fuck her once more too great to resist. Jeff walked back down her body and got to his feet at the edge of the bed, pulling her laying body closer to him. Her tits bounced from yanking her closer and could feel his orgasm would not be too far away now.

Annie knew what he wanted so she spread her legs wide and brought her knees to her chest to give him all the access he wanted. She was a little surprised though she realized she shouldn't have been when his bulbous tip poked against her ass once more. His push succeeded in getting inside her backdoor and he had to be satisfied starting at square one once more with short thrusts at slow speeds until she loosened back up.

"You want my ass again," she said with a smile that still looked pained.

"Of course I do. So do you. Anal whores always want it in the ass, don't they," darkest timeline Jeff told her.

Using a different approach Jeff cranked up his speed be fucking the large breasted college girl hard and fast but with only the first several inches. It worked well as his relentless thrusting helped to desensitize her and spread her out, all while she used her fingers to rub her clit and help herself enjoy the relentless sodomy.

After a bunch of fast pokes into her ass Jeff would go much slower but drill deeper into her booty, watching as her adorable face made a wide O and went silent until he pulled back and resumed his shallow assault. Annie had hooped her arms around her legs to hold them spread out which made her tits jiggle more freely, a sight to behold and made the evil man push closer to his inevitable orgasm.

"You're gonna cum, aren't you," Annie said, both her Jeff and the darkest timeline Jeff having the same tell.

"Yeah," he grunted while drilling Annie harder albeit with less rhythm.

"Cum in me..give it to me," Annie begged, though she was used to him filling her twat up, not her ass.

Her slutty words combined with the tightness of Annie's backdoor was too much for Jeff to withstand any longer. He pumped into her a few last times before burying his cock completely in her asshole, causing the coed to scream out as he shot his load deep in her asshole. Annie could feel his cock throb and pulse within her most sensitive of holes as his seed coated her inner anal walls before he pulled out.

Little did Annie know that he had one final thing left in store for her before he was finished. Bending down over her sex, he watched her asshole gape and periodical quiver as it attempted to tighten back up to it's pre-sodomy state. Wanting what he left behind, Jeff stuck his finger as far into her tushy as he could and rubbed around her walls, collecting his sperm from her.

"Oh My God," Annie shrieked at the digital intrusion into her ass.

"Thought you'd miss this since a creamed in her booty," he told her.

Annie saw his finger come quickly towards her face so she opened her mouth and allowed him to put his digit into her mouth. The cum tasted warmer and more bitter then ever before having been squirted deep in her bowels before hitting her tongue. She sucked hard on his finger like he wanted, Jeff watching with a satisfied smile.

"So how was that," she asked rhetorically, believing to know the answer.

"If I can be honest...not great," Evil Jeff told the younger coed. His words were like a slap to her face, an expression Evil Jeff wished he could photograph and share with the rest of the group.

"Wha...what," Annie asked in disbelief.

"No offense and you always want honesty. But you were...meh. Could improve a lot. I'm only telling you this because I believe in the truth," he continued.

"What did I do wrong," she asked so insecurely.

"It could just be a lack of experience thing. Listen, I'm going to be busy the next week doing my own business so while I'm away I need you to sleep around with as many people as possible," Jeff explained.

"Seriously," Annie questioned.

"I want us to be perfect and for that to happen you need to improve vastly. The failsafe way for that to happen is for you to fuck around...a lot. Like multiple times a day with as many partners as you can manage. Can you do that for us," Jeff said with a sincere look on his evil face.

"I...I guess I can," Annie said.

Jeff could already feel the timeline darkening as he smiled and left the girl alone in the apartment as he strode away to continue his progress.


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