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88-special · 3 months

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Female Jeff Winger

Summary: You give Jeff a run for his money when you join the group. Good thing he places all of his bets on you. The slow story of how you, the female version of Jeff Winger, stole the one and only’s heart.

Warnings: swearing, dear God lots of smuttt, elements of sexual harrassment? But Jeff takes care of that.

Word Count: 5k - AKA - too freaking long but so worth it, I promise.

Masterlist

It didn’t take long for the Greendale 7 to become the Greendale 8 when you started attending the community college. As much as the study group acted like they were just another group at school, everyone else knew the school revolved around them. You noticed this the first day on campus when they were in your biology class and made a huge stink about their lab partners. But, unlike the other students in the class, you refused to be a bystander and made a move to be one of the main characters. You remember it like it was yesterday.

*Flashback*

“You know, I really think you guys could use a fourth girl in your group just to even things out,” you said as you put your books in your backpack after class.

“Well, Pierce is hardly in the group anyway so it’s pretty even.” Jeff retorted.

“Hey!” Pierce yelled.

“Jeff!” Annie scolded. You laughed.

“Even if that is the case, I still think I could bring something fun to your table,” you flirted as you left the room, not wanting to beg for acceptance.

“You’re welcome to have some fun with me if you want!” Jeff called out after you as the other six groaned in disgust.

*Present Day*

One semester later and you were still sitting in the once empty seat between Jeff and Annie. You were something refreshing for the group. Someone who wasn’t afraid to be blunt, never hid anything, was always open about your life and your attitude. The way you saw it, too much time gets wasted hiding feelings or trying to save face. So in the moments when Annie and Shirley would go on their own sidequest in the group or when Britta tried to diagnose someone with a mental disorder, you were there to shine a light on the big picture before something big spiraled out of control and it was up to Jeff to make one of his speeches to save everyone’s ass. He would never say it, but Jeff slowly became thankful for your presence. In the beginning, he was a little threatened that you were trying to take his place as “leader” but as everyone got to know you better, you slowly fell into your role as negotiator amongst everyone. However, the flirtation between you and Jeff never stopped.

“What did you guys do this weekend?” Annie asked the group as they sat down at the infamous table.

“Andre and I went to the movies.” Shirley started.

“(Y/N) and I went to Ripley’s Believe It Or Not. We made candles shaped like our hands.” Britta shared.

“I was busy getting laid like a man,” Jeff mumbled, attention fully on his phone.

“Uh!” Annie crossed her arms.

“Gross.” Britta groaned.

“Oh, really? And exactly how does such a manly man get laid? Doggy style? Or missionary?” You turned your full body towards Jeff, hand resting under your chin. You now had Jeff’s full attention, his eyes slightly widened at your words. He quickly reacted, putting his phone down on the table and staring you down.

“Missionary, I like to see the face they make when I fuck them.”

“Really? I would’ve figured doggy. With a narcissistic ego like yours, it’d give you full control.”

Jeff smiled and leaned back into his chair. He opened his textbook then mumbled, “Reverse cowgirl.”

“Ha! Make them do all the work sounds fitting.” You mirrored Jeff and opened your book as well.

“You guys!” Troy yelled.

You and Jeff looked up to see Troy covering Abed’s ears and Shirley covering Annie’s. Britta sat covering her own.

You let out a breathy laugh and looked down.

“Alright, chapter 4!” Jeff announced. He looked down at you, feeling his eyes, you made eye contact with him seeing his side smirk before looking back at your books.

You were never shameful about the information you shared with the group. If anything you think you helped them break out of their comfort zones. Especially Jeff as you two shared your one-night stands with each other. Something Jeff solemnly enjoyed knowing how the rest of the group would respond. While this was a rare occurrence as most of both of your times were spent with the rest of the group, it was still nice to have someone to talk to about your sexual relations. You were someone Jeff has never seen before. He’d become so accustomed to a certain type of woman that he knew what plays he had to make for a quickie. But you weren’t like that. You left Jeff confused.

If anyone else talked to Jeff the way you did, he’d have them pinned against a wall in seconds because he would know it’s what they wanted. But not you. You were so matter-of-fact about everything you said, no matter how dirty. There was a time when you two were having lunch at the cafeteria together and the conversation somehow became about eating a girl out. Jeff automatically claiming to be great at it and you immediately quizzing him on his habits. By the end of the conversation, Jeff was taking notes and you had to leave abruptly to avoid being late to a class. By the time Jeff finished writing and saw you were gone, he was left slightly winded by the things he learned and slightly hard.

These interactions continued every week and slowly Jeff became more enamored with your presence. He would look for you in every room. He would be anxious if you weren’t at the study group. And most importantly, he was having fewer one-night stands. The two of you would steal glances at each other and slowly talk about things more personal. Even though you were very open to the group already, you still had things hidden. It was as if Jeff had access to a hidden flashlight that only you let him use to get to know you better.

You had always found Jeff attractive, even before joining the group. If he came to you one day and wanted to sleep with you, you’d do it with no hesitation. But you’d be damned if you were the one to initiate it. You loved the friendship you had with Jeff and how close were able to be with him. You didn’t want to jeopardize anything by having sex. So instead you flirted, and talked about having sex with other people, leaving out the parts on how you wished it was him. This was something completely contradictory to how you would normally operate. If you were infatuated with anyone else you would’ve boned them by now. But this was Jeff you reasoned. You knew how he operated. He flirts with everyone and you didn’t want to be everyone to Jeff.

That is until things started to shift leading up to one of the many school dances. You had somehow managed to capture the attention of a man named Trey. Trey flirted with you every single day in math class. You were very much not interested and you told Trey every single day. You had even expressed your frustrations to the study group. But there wasn’t much to do; he was stuck in a class with you. Things started to escalate the week of the dance.

The study group had ended another meeting and was walking to their next class together when Trey approached you.

“(Y/N), will you go to the dance with me?” Trey knelt down with a bouquet of flowers in front of you.

“No, Trey. I don’t want to go to the dance with you. I don’t want to go on a date with you. I don’t even want to talk to you. Leave me the fuck alone.” You spoke deliberately, hoping this time he would finally listen to you. You walked around him, the group following you to class.

“Hey!” Trey yelled, he ran up to you and grabbed your arm. “Just go to the dance with me, I’ll give you anything you want, I’ll show you I can be the man you want.”

“She said no dickface. What part of that don’t you understand?” Jeff scolded. His eyebrows furrowed.

“This doesn’t concern you, man. (Y/N), I love you please.” Trey caressed your face with his opposite hand.

“Ugh! Get off of me!” You slapped him and wiggled your arm out of his grasp.

“Hey!” Trey started to move towards you but Jeff dropped his books and grabbed him, pinning him against the lockers.

“You fucker. What the fuck makes you think you can force a woman to date you? You’re a pathetic piece of shit.” Jeff said in a deep, threatening tone, his face inches away from Trey’s.

A few moments later security arrived to remove Trey from the premises where he was later expelled.

“(Y/N), are you okay?” Jeff asked.

“Yeah, I think so. Thank you, Jeff.” You hugged him and let out a deep breath you didn’t know you were holding in.

It had been a few days since the incident with Trey and it was now the night of the dance. You didn’t really want to go at all but Annie begged you to and knowing you would be able to see Jeff in a suit pretty much solidified your decision. You and Jeff spent most of the night standing at a tall table drinking punch and talking about other people.

“What about her? Look how tall her heels are? I bet she’d be fun in bed.” You motioned towards a blonde on the dancefloor. Jeff followed where you were pointing.

“Nah, I don’t think I’m in the mood for anyone tonight,” Jeff revealed, taking another drink.

“Why not? I’ve noticed I’ve been doing all the talking on our relations here. What’s up with you? Erectile dysfunction?”

Jeff stifles a laugh, refusing to make eye contact, “No, I think I have my eye on someone else.”

“Oh, alrighty then. Well, I hope I get to meet her. Hey, what do you think of him? He’s a little short but looks strong.” You quickly changed the subject, flexing your arm muscles to mimic the man you were referring to.

“What for you?” Jeff asked.

“No for you, yes for me, unless you have something you’re not telling me.”

“Very funny. I just didn’t realize you were looking tonight.” Jeff still refused to make eye contact with you.

“I need something to get past Trey, he freaked me out a little and I haven’t felt like myself. I need to know I still am myself even just for a one-time thing.” You admitted.

There was a moment of silence between you two. Both of you looking at the man you brought up in discussion. Before Jeff spoke again, he sighed.

“I think you’re capable of whatever you put your mind to. Just be safe okay?”

“I promise.” You tapped his arm and made your way over to make your acquaintance.

When Monday arrived, you appeared slightly happier as you walked into the study group. Feeling more like yourself after the previous week’s events, you were excited to go to class knowing there was no more Trey.

“Hello (Y/N), how was your most recent escapade?” Pierce asked.

“Delightful. Thanks for asking.” You sat your stuff down before sitting next to Jeff and waiting for the usual banter to commence before actual work got done.

“Okay, so we’re on chapter five right?” Jeff asked, opening his book to your surprise.

“What did you not do anything fun this weekend?” You asked.

“I just want to be ready for our test tomorrow.” Jeff shrugged, never looking up at you since you arrived.

“Okay, then.” You mumbled, opening your textbook too.

At lunch, you noticed how Jeff decided to sit on the other side of the table from you as opposed to usually sitting next to you with his arm around your shoulders. You pretended not to feel hurt by it and continued to participate in the group’s discussions, glancing at Jeff every once in a while, trying to figure out what was wrong.

By the end of the day, Jeff had hardly spoken to you and you had had enough of it. You were determined to know why your best friend was giving you the cold shoulder. So, after your last class of the day, you walked out to Jeff’s car, knowing he wouldn’t be there for another 10 minutes after his class. You leaned against the driver’s door, arms crossed, and waited.

“You better not have scratched the paint.” He called as he approached you, his keys in hand. “What do you want?”

“I want you to tell me what the hell your problem is! You’ve hardly spoken to me all day.”

“Right now, my only problem is someone standing in the way of my car.”

“Jeff.” You sighed, not wanting to fight. “Please. Did I do something wrong? Something is different and I don’t know what it is or how to fix it. Did something happen with the girl you were talking about the other day?” You noticed a slight change in Jeff’s demeanor when you mentioned the other woman.

“No, (Y/N) you didn’t do anything wrong, this is something I have to deal with myself.”

“But it does have to do with that woman! What happened? Did she turn you down? Tell me who she is and I’ll talk to her, tell her what a “great guy” you are,” you mocked.

“No, (Y/N),” Jeff said sternly as he tried to get past you to unlock his car.

“Why not?” You pressed, stepping in his way again.

“Because you’re the woman I was talking about!” Jeff yelled frustrated. Your smile left your face and your eyes widened. “For fucks sake.” Jeff groaned. “Look, I really like you (Y/N). I don’t know when exactly it’s just-” Jeff sighed, his eyes focused on his feet as he tries to figure out what the hell he’s doing. “ We’ve gotten really close since you joined the group and yeah I thought you were hot when I first saw you but now it’s like- I don’t know you’re not like anyone else I’ve ever been wi-”

“Oh, gross please. You did not just use the ‘you’re not like other girls’ line on me.” You interrupted.

“No! Would you just shut up for a second? It’s just I can usually read people and tell if they’re interested in me or not and you’re unpredictable. You take my shit and throw it back in my face, you’re someone I can talk to and I’ve never felt like that before. I don’t know how to explain it because I don’t have my shit together but I don’t like seeing you with anyone else. I stopped seeing other woman because I kept imaging they were you. And I don’t want to fuck things up with you. So I’m sorry I’ve been a dick today I just-”

You grabbed Jeff’s collar and smashed your lips against his. It wasn’t pretty. In fact it was very messy. Both of your lips moving against each other’s in some form of hunger. After a few seconds you pushed him away leaving him confused for a second. You had his attention now. Jeff was no longer looking at the ground but was searching for your eyes to figure out what the hell that was. Except you weren’t looking at him now. You were staring off into space as you briefly touched your lips with your fingertips as if to make sure that really happened. After a few more moments you finally made eye contact.

“I’ve wanted to do that since the first day I saw you.” You admitted. Jeff let out a small, breathy laugh, his lips curving at the edges. “Jeff, I don’t like seeing you with other people either.”

“Are you serious? You never said anything! You always have something to say when you have feelings!”

“Because you flirt with everyone! And I don’t want to be everyone to you. I can’t just have sex with you and go back to normal.” You crossed your arms and leaned back against his car, no longer looking at Jeff, closing yourself off. You just let your biggest secret out in the open to the one man who’s opinion actually mattered to you.

“Hey,” Jeff whispered, “look at me.” Jeff set his books down on the roof of his car and placed his hands on your shoulders, leaning down so he was eye level with you. “You are not just like everyone to me. I like being around you. I like talking to you. I want to keep you safe. And I really want to fuck you.”

“Jeff?” You looked up at him with wide eyes. “I really want you to fuck me.” You whispered, tilting your chin up towards his, he could feel your breath on his lips. Jeff leaned dow the rest of the way, pressing his lips back on yours a little calmer than the first time but no less hunger. His left hand settled in your hair, his right one on your hip pulling you closer to him where you could feel his hips against yours. Jeff pulls away slightly but continues to kiss down your neck.

“My place or yours?” He asks.

“Mine’s closer.” Jeff reluctantly pulls himself off of you and finally unlocks his car. You run around to the passenger side and let yourself in. Jeff throws his belongings in the backseat and you give him directions to your apartment.

When you arrive to your apartment you had a difficult time unlocking your door with Jeff pressing himself against your back. His arms reached around your body, one grabbing at your breasts as he turned your neck into a work of art. You decided two can play at this game and pushed your ass into his crotch eliciting a low groan from him as he halted his advancements.

“Naughty girl.” He whispered. You laughed as you finally got the door open and let him inside.

The two of you continued your making out as you guided him to your bedroom. By the time he pushed you down on the bed you were both stripped down to your underwear. Jeff took the moment to stare at your body spread out on the bed waiting for him. You bit your fingernail in anticipation and took the moment to stare at Jeff’s muscles as well. You could see the outline of his hard cock in his underwear.

“God, you’re so hot.” Jeff said as he knelt between your legs and placed himself above you. He leaned down to kiss you, his left arm holding him up while his right arm held your hip. Your arms loosely wrapped around Jeff’s neck and your legs around his waist. Your tongues meeting and mixing different tastes causing you to moan. Jeff moves his kisses down your neck to the tops of your breasts that sat above your bra. He leaves marks wherever he travels.

“Can I take this off?” Jeff asks, sitting up to look at you.

“Yes.” You lean up on your elbows so Jeff can reach around your back and unclasp your bra. He quickly throws it off to the side and you lay back down.

“Fuck.” Jeff mutters to himself making you laugh but your laugh is cut short and turns into a moan when Jeff starts to suck and lick your nipples. Whatever isn’t receiving attention from his mouth is receiving it from his hand and within minutes your breasts are covered in purple and blue markings.

When Jeff is pleased with his work he continues to kiss down your navel, stopping at the top of your underwear before he leans back on his knees and looks down at you.

“Is it okay if I take these off?”

“Yes.” You breathe. Still in disbelief that Jeff is going to see you naked. You lift your hips enough for Jeff to easily move your underwear down your legs and he tosses them in the general direction of your bra. He kneels between your legs and starts to kiss up your inner thighs. You stare at your ceiling, trying to control your breathing as Jeff Winger gets closer and closer to your pussy. Before he advances further he looks up at you and notices how you’ve closed your eyes and your chest move up and down with each breath.

“Hey, are you okay?” He reaches up to grab one of your hands in his.

“Yes, yes oh God. I just, can’t believe this is real.” You laughed, making eye contact and grasping his hand tighter in yours. Jeff smiles and squeezes your hand back.

“Tell me if you want me to stop and I will.”

You nodded, smiling at Jeff and watch him lean back down to his previous position, his hand still holding on to yours. He has your legs spread wide enough for his shoulders to fit between them. He has the perfect view of you. Without further ado, Jeff licks up between your folds. You sigh, pressing your head back against a pillow, closing your eyes, and relishing in the pleasure of Jeff’s tongue. Jeff continues to explore your pussy and runs his tongue along the sides, around your hole, and back up to your clit where he gives it a couple of swipes making your hips move up and a moan escapes your lips. Jeff smiles and uses his free hand to hold your hips down.

Jeff focuses all of his attention on your clit. Sucking, licking, moving his tongue in circles, he explores other sensitive areas until he finds the exact spot that makes you cry out and focuses all of his attention there. He never moves, never stops, you’ve never experienced someone as persistent as Jeff was at making you come from his tongue alone.

“Oh my God, Jeff fuck.” You whined, your hand still squeezing Jeff’s, the other one pulling in his hair. Jeff groaned at your noises and picked up his pace feeling your hips move against him.

“Jeff, I’m close. Fuck don’t stop.” You were a mess. You could feel yourself teetering on the edge of euphoria and finally the dam broke. You cried out and Jeff let you move your hips against his face and slowed his pace as you came down from your high. Jeff crawled up your body and kissed you, softer this time. You could taste yourself on his lips and tongue.

“I like how my name sounds when you say it.” He confesses in a whisper.

“Who taught you how to do that?” You smirk.

“You did.” He matched your smile, reminiscing of your conversation about eating girls out.

“I must be a fantastic teacher.”

“One of a kind.” Jeff pushes off of you, rolls off the bed, and walks to your bedroom doorway where his jeans lay. He pulls out a condom from a pocket and walks back to you.

“How many do you usually keep with you?” you inquire. Jeff hesitates for a moment, trying to read in between the lines of your question. Do you actually care and this is an insecurity talking? Or are you just making fun of him? He looks at you and sees you with your hands folded behind your head. You give him a soft smile and raise your eyebrows in a suggestive way. Jeff laughs.

“Just the one. What did you expect?”

“I’m surprised you don’t have a rep from Trojan following you around at your beck and call.” Jeff lets out a huge laugh making you smile proudly.

“I tell you what,” Jeff pulls down his boxers, “I’ve never laughed this much during sex.” He rolls the condom onto his cock and looks back up at you. All signs of jokes and playfulness have left your expression and you just stare at Jeff’s cock.

“Do you like what you see?” Jeff poses, hoping to make you laugh again, not entirely sure what you’re thinking. You bite your lip and make eye contact again. You nodd at Jeff, truly at a loss for words at his naked appearance. Jeff smiles and returns to his original position above you but you place your hand on his chest to stop him.

“Wait, I want to be on top.” A glimmer shown in your eyes at the idea. Jeff lets you push him over with little hesitation and now his arms are folded behind his head and your legs are spread on either side of Jeff’s waist.

“If you want to do the work, be my guest princess.”

“I just like the idea of having Jeff Winger under my control.” You whispered in his ear and kiss below his earlobe. You continued to move your lips across his neck and up to his mouth again. Your hands grab onto Jeff’s and pin them by his head. Jeff groans, his body slightly tense but nevertheless, he lets you take the lead. Whatever makes you happy.

You pull back into a sitting position and slowly lift yourself up to hover over Jeff’s cock. You wrap one hand around him and pump it a few times. Jeff quickly inhales and sighs at the feeling. You run his tip between your lips and shudder as you pass your clit. Jeff groans in response and your legs shake slightly.

“Fuck, I guess I’m still sensitive.” You smirk.

“I must be a fantastic student.” Jeff retorted about his handiwork. Finally, you line up Jeff’s cock with your hole and slowly lower yourself onto him. You fall forward, your palms pressed against Jeff’s chest to hold yourself up. Jeff’s hands automatically find your hips and follow them as they lower all the way down until you’ve fit all of him inside of you.

“Oh my God.” You breathed staring down at Jeff.

“Fuck sweetheart.” Jeff groans, “you feel so fucking good.” His voice deep and raw causing your pussy to flutter slightly making Jeff flinch. You slowly raise yourself up and down, gaining a rhythm and speed. Jeff’s hands never leave your sides.

“Holy shit, you’re so fucking sexy (Y/N).” Jeff groans. His hands run up your back and pull you down to be level with him. His hands return to your hips and he moves with you, meeting your pace but hitting even deeper inside you.

“Oh fuck Jeff, yes!” Jeff groans a low guttoral moan at your noises and picks up his pace. It doesn’t take much for you to let him take over again and he’s pounding his cock up into your pussy, hitting all the right spots to make you feel dizzy. Your hands are running through Jeff’s hair, you’re face down on his shoulder as he slams his hips up toward yours.

“You’re mine (Y/N).” Jeff spanks your left buttcheek making you cry out.

“Jeff please, I’m so close.”

“I’ve got you (Y/N).”

Jeff continues to hit your favorite spot until he feels your pussy start to convulse around him. You let out a string of moans and cries of Jeff’s name as he makes you come. With a few more thrusts Jeff is groaning too and his hips still inside you. He thrusts a few more times before finally relaxing and calming his heartrate.

Jeff wraps his arms around your back, your chest pressed against his, your face positioned towards Jeff’s but you’re too tired to open your eyes at the moment. Both of you breathing heavily, sweat sticking your bodies together. After a few minutes, you lift yourself up and slowly raise your hips off of Jeff before rolling onto your back.

Jeff rolls off the bed and walks to your bathroom to dispose of his condom. He cleans himself up a little and puts his boxers on. He taps on your thigh to get your attention.

“Hey.” He gently whispers. You look up at him and see a washcloth in his hand. You spread your legs a little with as much energy as you can muster and he gently cleans you up as well. Once he’s done, he pulls your covers over you and joins you in your bed. He starts to wrap his arms around you to spoon you but you surprise him by turning around and wrapping yourself around him like a koala while he’s flat on his back. Your head lies on his chest and you can hear his heartbeat if you’re quiet enough.

“What does this make us?” You ask. Jeff tenses below you making you laugh. “Relax, I know you. I’m not looking for a boyfriend girlfriend label I just… want to know where I stand with you.” You explain.

“I promise you’re the only girl I have sex with.” Jeff offers. You smile.

“Likewise. But is that dating? Or friends with benefits?”

“We’re seeing each other.”

“We’re seeing each other.” You repeat.

“You’re more to me than a friend with benefits.”

“But dating would mean boyfriend girlfriend?” You ask.

“I don’t want to rush whatever this is. I don’t want to complicate it with labels. I just want it to simply be.” Jeff explains in a rush. Feeling as though he finally got something off his chest yet, still worried about how you’ll react.

“Okay.”

“Okay?”

“Yeah, okay.” You tilt your head to look up at Jeff and see him already looking down at you. You raise your left hand to run through his messed up hair. “We’re exclusive together.” You shrug. “I can do that. And when you decide you want a label, let me know.” You confirm.

Jeff feels as though he might cry. He’s never met someone so understanding of who he is and doesn’t push him into anything he doesn’t want. But instead, he opts to kiss you and hope that you can feel his appreciation than way. You return to laying against Jeff’s chest and Jeff lays back on your pillow, both of your arms wrapped around each other as sleep takes over.

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