Disclaimer: Community and its wonderful characters are property of Dan Harmon and NBC.

Spoilers: Some for a few S1 episodes, as well as Early 21c. Romanticism, Intro to Poli Sci, Conspiracy Theories, Custody Law and EE Diplomacy and Cooperative Calligraphy...but really would you be here if you hadn't seen those episodes? Probably not, but I have to mention possible spoilers anyways.

This fanfic is very loosely autobiographical.

Mention(s) of fellatio and female arousal, as such this is rated T, for Teen.

Takes place after (alleged upcoming) paintball finale, but has been in the writing process since just after Asian Population Studies. There may or may not be inconsistencies.

First one, reviews appreciated.

-Indecent Proposal-

1) Like Spearfishing with a skipping rope.

Finals Week...

Two hours earlier, the modest classroom had been full of students, including several of his peers who had also taken Applied Calculus (Chang, Annie, Pierce and Abed had also enrolled in the class…Shirley, Britta and Troy took some class called 'German People'). However, math was something that some people just had a knack for, while others had to work hard just to scrape by, and Jeff Winger was definitely in the latter camp.

He only took this stupid class because he figured that Professor Tavares would be generous with his grade, as he had helped him ensure that his wife didn't clean him out in his divorce a few years ago. It was a decision he regretted; Tavares wouldn't budge, and math was certainly not Jeff Winger's 'thing'.

Even still, after some help from Annie and Pierce (who was shockingly math-savvy), Jeff felt confident in his preparedness. The good thing about math, probably the only good thing, was that you were either right or you were wrong; there was minimal grey-area in the subject.

As of this moment, the only people left writing the exam, Jeff's last of the year, were Annie, Garrett, Starburns, Chang and himself; Annie had probably finished a half an hour ago and was riding it out checking over her work. Time was almost running out as well, but Jeff just had to finish one last equation and…there, done. Applied Calculus, you wouldn't defeat Jeff Winger…

Not a minute later, Professor Tavares looked up from his watch and said 'Time!', everyone - even Annie, no doubt having learned from the last time - put down their pencils and raised their writing hands; even if Chang was certifiably insane and Tavares was a reasonable and easy-going (if not a little bland) man, she had learned not to test her professors.

"Bring your papers to the front and hand them in." Tavares said in a slow droll as everyone rose, "And have a great summer!"

Jeff, his mind wholly on the exam and nothing else, left the room quickly, forgetting that before the exam Annie was giving him 'I need to tell you something important...but not until I'm done with the exam, tee hee!' eyes. Normally Jeff would have recoiled into his shell at the prospect of possibly having to hurt his young (though precociously sexy) friend again, but one thing this year had taught him; he and Annie was probably never going to happen.

...Good... ... ...

He was halfway down the hall when he heard the pitter-patter of small footsteps and his name stretched to two syllables, 'Je-fff!' that he turned around to see Annie, wearing her mustard-colored cardigan (the tightest one she had, damn her) and a medium-length grey skirt.

"Was it good for you?" He said with a lascivious smile, to which she smiled and blushed, looking down and playing with her hair.

"I think I did well, it wasn't too hard." She said, knowing well that her copious notes and overwhelming discipline was going to pay off, "You?"

"I have a feeling that Jeff Winger will maintain his sterling C average." He said with a laugh as she did her 'You're cuter than Justin Bieber!' blush and smile, letting out a quick laugh. Chang materialized out of nowhere behind them.

"How are we doing today, study bitches?" Chang wrapped his arms around both of their shoulders, "Nailed it, NAILED it!", he pumped his fist.

"Uh, we're good..." Jeff said hesitantly, "Actually, Annie had something she wanted to ask me, so I'll see you back at the place?"

"Oh I see." He stepped off and regarded them with scrutiny, "You're throwing me a Chang-up because you need me to leave so you can give Lori-Anne her bi-annual tonguedown in private, I get that..."

Annie squeaked and Jeff's face hardened as for a brief second things felt awkward.

"Well speaking of...that." Jeff said with indifferent cool, "You've been staying with me for two months now...is there going to be a Chang in your living arrangements this summer?", and he mentally facepalmed himself with the end of that sentence.

"Actually yeah..." He said, "I've been talking to my wife lately as you know, and she agreed to take me back. I'll be out of your place in a few days and back to having Changry sex with the Senorita within the week."

"Good…for you…I suppose…don't forget to take your crabs with you." Jeff said he looked down.

"I told you that you'd fall in love with them, you can keep Jeff if you want...but anyways I have to go have a chat with the Dean before he leaves for the furry convention...adios gaywads!"

With that slightly homophobic signoff he left, waving behind him without even looking. Annie now regarded Jeff with a pained expression, like someone told her that she had to take Old Yeller behind the shed for one last walk.

"Wow, living with him must have been excruciating." She said empathetically.

"You have no idea." Jeff reminisced; secretly, other than the kidnapping incident it wasn't that bad. Chang was fairly clean, cooked four nights a week and kept his wearing of Jeff's clothes to a relative minimum (though he did notice that he was missing three pairs of expensive Burberry boxers), but most of all he was company; not always good company, but company nonetheless. He turned his attention back down to Annie, "So, what did you want to ask me?"

They began to walk together through the slowly emptying halls of Greendale, "What are you up to this summer?"

Nervous small talk...how Annie of her, "I'm going to do some consulting for my old firm, work out, maybe go see a friend in Cali and de-Chang my place after he leaves, nothing much, what about you?"

"I'm actually moving back in with my parents, we've reconciled!" She said as she practically hopped up and down in front of him.

"Well that's good news." He wanted to pat her on the head and tell her 'Good job', but he didn't like to demean her like that. He had gotten to know Annie a lot better this year. She was the total opposite of Britta, who put up a tough front to hide her deeply vulnerable and insecure true nature. Annie came off sweet and vulnerable, but in reality was a very strong and independent person.

"Yeah, and I'm taking some summer courses, too...you know...always working Annie!" She gushed again.

"I wouldn't have it any other way..." Jeff said lovingly.

He could hear Annie cooing as she colored.

"...how would I ever pass my courses?"

Her expression turned mock serious, though a trace of a smile still remained on her face as she slapped him in the arm.

"Annieways..." She started before covering her mouth and flushing. Jeff regarded her with an aghast stare.

"Please don't…"

"Sorry..." She straightened out her dark skirt and looked at him again, "Anyways, one of the classes I'm taking is...Human Sexuality…"

Jeff raised his eyebrows, "How un-Annie of you..." He said with his mouth, but his mind realized that it wasn't such a reach; beneath her prim and proper exterior, Annie was very sensual and curious, which he secretly loved.

As he had gotten to know her better, Jeff had seen that there were really two sides to Annie; the innocent and super-feminine side that liked kittens and rainbows and cheesy rom-coms; she was what most people saw every day. The other was a dark, sexy side that liked tattoos and motorcycles and risky sex in public places, as if just seething below the surface of her conservative exterior was a bad girl just aching to be let out of her cage; she was the side of Annie that only came out in extraordinary circumstances, such as when she realized some hippie asshole wasn't good enough for her or she was getting tired of losing her pens.

Jeff both thought and tried not to think this.

"Can I sit you down and ask you a few questions? It won't take long." She askmanded, a term that he had coined, where Annie asked Jeff a favor and used her big, sad eyes, squeaky little voice and petite-but-voluptuous figure to render him unable to refuse her. Normally her askmands were more painful and or embarrassing, so Jeff was happy that this particular one was just a few questions.

"Sure...coffee?" He said, totally unaware of what was happening.

"Yeah, but somewhere off campus?" She preened.

"Alright, let's go."

Twenty minutes later they were at the coffee shop just around the corner, seated with their coffee in front of them in a secluded corner booth. Annie removed a notebook from her backpack and one of her signature purple pens and placed them side-by-side. Jeff had noticed that this particular notebook was blank; a fact which Annie tried (and failed) to hide by flipping to the middle of it.

"So..." She blushed and faded. She wanted to smile but to Jeff it looked like a mix of jittery nerves and fear had drained the color from her face.

"So..." He said inquisitively.

"How old were you when you had your first sexual experience?" She asked, hushing her voice when she said 'sexual'.

"What do you mean by 'sexual experience'?" He asked, lowering his voice when he said 'sexual' to mock her. She smiled and rolled her eyes.

"You know…Intercourse?" She whispered.

"Okay Annie." Jeff locked eyes with her and noticed her eye contact failing, "How do you plan to pass a class when you can't even talk about the subject matter without lowering your voice and blushing?"

"I didn't think there would be too much oral work in the class..."

"A sexuality class with no oral work, I'm glad I'm not taking it." Jeff laughed to himself as Annie colored like a tomato, "But even if there isn't a lot of...oral work, you don't think the cute young A-student who sits at the front of every lecture will ever have to answer questions? There won't be any presentations? No dioramas? No group work? That is an egregious oversight for you, you study and dissect course descriptions a month in advance before you decide which classes to take."

Annie looked shocked, as if she had been hit by a big revelation, "You're right!" and she rose ready to grab her bag, "The deadline to drop summer classes is eight P.M, I can still make the admissions office if I leave now...", but she was stopped when Jeff gently grabbed her hand, and she sat down once again. How did he do that? She wondered. How did he always make her feel stronger than she was?

They sat in discomfort, or at least Annie did for a full minute, before Jeff looked at her again. "Say Sex, Annie..."

She looked at him for a second, "Sex..." she whispered and blushed.

"Say it louder or I swear I'll turn this car around..."

She looked startled at this idea, before sitting up straight (and sticking out her ample chest), "Sex?" she said more loudly.

"A little better, a little better" Jeff said with encouragement, "Now say Penis."

"Je-fff!" She pouted, "I'm not saying the...p-word.", and what was adorable was that she even lowered her voice to say 'p-word'.

"What? You think anatomy isn't going to be part of the curriculum?" He laughed as he said this, "A penis is pretty important with regards to sexuality...Abed has one, Troy has one, Vaughan has one, I have one, Pierce probably even has one."

She covered her ears and flushed an even brighter shade of pink, right as he said his name; he had to wait a second before she removed them to continue, but Jeff definitely picked this up, "I'm not here to judge you, Annie, you asked for my help. Consider it a privilege, because you're one of maybe four people who I would even bother to help in the first place."

She realized he was right and took a second to regain her composure, before looking him in the eyes, "Penis?" She said in a voice above a whisper.

"Now Vagina..."

"Vagina?" She said, louder this time. She smiled and adjusted her posture proudly.

"See? It's not so bad, you'll be fine, Edison."

"Yeah...I will be." She said, before writing something in her notebook, "So are you ready to get back to the questions?"

"Bring it on."

"Okay, so, the age that you first had sex?" And she said it without lowering her voice.

"I was twelve" He answered her.

"Gross!" She made a 'yuck!' sound.

"I developed sexually at a very early age, Annie. When I was twelve I was five-foot eleven and I weighed 160 pounds. I was ready, I could handle it."

"When I was twelve I was four-foot seven with a backbrace and no boobs." She said with remorse, while at the same time wondering what Jeff was like when he was twelve; he was probably cute and popular and well-loved by all, like Troy only white and with a triple-digit IQ.

"And even though you didn't get any taller, you have wonderful posture, and…" He unwittingly cast a brief, sly look down at her chest, where a small bit of cleavage beckoned him. Annie noticed and made a shocked gasp but hardly moved to cover herself, "You developed pretty nicely…"

She colored once more and was visibly awkward, but at the same time she smiled a flattered grin and brushed a strand of hair aside, "Okay, question two; have you ever had an experience with a member of the same sex?"

Jeff looked at her incredulously, "Pierce put you up to that one?"

"This is strictly confidential; Pierce is the last person I'd tell...well the second last after Shirley."

"Well it's not a big deal, there's nothing to tell; I've never had a homosexual experience and plan to keep it that way."

She jotted his answer down, "I was 99% sure on that one but I had to ask. Are you ready for the third and final question?"

"Hit me with it."

"How many sexual partners have you had in your lifetime?" She asked innocently...or did she? He used his lawyer-sense to see if there was some sort of ulterior motive behind this question, as their often was, but Annie was getting very good at covering her tracks; he came up with nothing, so he went to his default mode.

"Pass." He dismissed the question as he took a sip of coffee.

"Je-fff!" she prepared to askmand him once more, but he stopped her short.

"Annie that is such a loaded question." Jeff began one of his patented speeches, "If you were Troy or Abed, I would give you an honest answer and then we'd high-five and laugh, I might even tell a few stories, but you're..."

"A Unicorn..." She said in shame as she lowered her face to the table.

"A girl, Annie." He said, "And this isn't the first time a girl has asked me that question, and in my experience there is no right answer, so I deflect it with whatever means are available...usually sex, sometimes flowers and gifts, and actually once with a weekend trip to Cabo."

"I'm not trying to do something underhanded with you Jeff." She squeaked, finally looking up, "It's just for my research."

"How do you know I won't lie?"

"You would lie?"

"Well as I said; no right answer. If it's too low you think I'm a loser. If it's too high you think I'm gross. What's my recourse here?"

"I can assure you that your results are confidential...and I'm not judging you..." She stammered, putting on her formidable face, "And if you must know, I'm doing some pre-emptive research so I can get some rough numbers, I'm going to be asking Troy, Abed, Pierce, Britta, Shirley and some other people after I talk to you."

"Well I'm so glad I could be your first." Jeff said in his normal voice; cocky and smarmy with just a hint of subterfuge and sarcasm. Annie blushed noticeably and looked at the ground for a second.

"Je-ffffffffff!" She pouted adorably.

"Alright, alright, just give me a second." He laughed and raised his hand, before locking up inside his own head...so many memories, so many girls...mostly beautiful, some average and a very few less than average, he tried to block most of those out as he came up with a rough number.

When he was young he kept score, but the older he got, the more it seemed like it was unnecessary; what exactly was he trying to prove? How immature he was?

Of course he remembers certain milestones; he lost his virginity at 12, but Annie didn't need to know it was totally a lucky bounce. He was staying with his aunt when his 15-year old cousin had a party, and he didn't even try, or even have to...it just happened.

He had his first threesome with his sexually-curious type-A ex-girlfriend Claire and her bisexual, busty friend Allie when he was 24, but that had ended horribly; he dumped Claire and was with Allie within a month.

He slept with his (estimated) 100th woman when he was 29, a young, redheaded intern at the old firm, but he was the type of guy who remembers his sex life by the experience more than by which number she was.

"The real and honest answer, are you ready for it?" He asked, building up her suspense.

"I am..." She said timidly.

"About 130, plus or minus a few" He answered with a smirk...the ladies love Jeff Winger and he gets more play than Dark Side of the Moon.

A shocked and almost disgusted look came across her face as she curled her mouth and he smiled, "Jeff! Gross! That's like a third of the female population of Greendale!"

"It's not that bad, Annie." He assured her; why was it bad? "I first had sex at 12, I'm 33, that's just over six women a year for twenty-one years, one every two months. I've been at Greendale for sixteen months, and in that time there was 'Mommy', Tube top REM concert, Slater, Amber, Britta, that annoying kid's mom, Quendra and Rebecca…If anything I'm at least consistent."

"I know all of those except Rebecca.' She asked, writing something down.

"I met Becky in the health center when I found out I had high cholesterol." He confirmed for her, "We went out a few times after Nurse Jackie tried to give her a pap smear, she was very nurturing and adventurous...but she has a boyfriend."

"Well even still...gross!" She crossed her arms...but for a second, just one second, he swore that he saw a devious smile creep across her face and vanish into the ether. He wondered what she was thinking; her feelings to him hadn't fully died (after finding out about him and Britta, he was 'gross' for all of twenty minutes) and they may have even been mutual...

Or was she just realizing that two of those girls, Quendra and Rebecca, were around the same age as she was which would make his objections null?

In reality Quendra is 25 and Rebecca is 23. Annie is still just 20...and Annie.

They both simultaneously took a sip of coffee as tension began to swim in the air. When they both placed it down and looked everywhere but at each other, Jeff was the first to speak.

"What about you?" He asked.

"What about me what?" She asked in mock ignorance, but Jeff's head-tilt told her exactly what he meant.

She hesitated for a second; should she be honest with him, as he had with her even as much as it pained him, or should she lie? She hated being branded a Unicorn, hated always being thought of as a little-girl; innocent little Annie, prudish and Jewish, repressed and constantly upset.

But Jeff was different; more than anyone else in the group, he saw her as an adult...sure, they couldn't be together because of their age (his choice, not hers), but he was always mostly respectful of her and always listened to what she had to say, but most of all, he never let her have it both ways; She couldn't demand to be treated like an adult while still enjoying the perks of childhood with him, and at times this got messy (such as the time she told the Dean that Chang was a fraud and he screamed at her), but still...it felt nice to be seen as a peer and not a burden, even if it was just with him.

Even now, he and she could speak relatively frankly about sex, without him judging her (like Shirley), advancing on her (like Pierce), comparing her to a TV character (like Abed), totally missing the point (like Troy) or treating her with kid gloves (like Britta).

"I've never had sex before..." She finally revealed a revelation which made Jeff's pupils dilate.

"I thought I heard about some gay boyfriend from high school, what was that about?"

"Well...It was a week after I got out of rehab. I lost 40 pounds and my skin cleared up, and my high school boyfriend Lance called me." She started, blushing on queue like clockwork as she did, "His parents were out of town so I went over, and I knew...I mean, I suspected he might have been gay before, but then before I knew it we were on the floor of his walk-in closet, kissing and embracing, Madonna playing on his iPod, and he pulled off my panties and his boxers, and...and...and..."

Jeff had the weirdest boner; she was being surprisingly detailed and unabashed about her one sexual experience, he should take a picture because this was like finding Bigfoot, "Yeah, and then what happened?"

She looked at him and was aware of his state, "And...nothing..."

Jeff took a second to glean her blank, melancholy expression, as well as his knowledge of the human sexual act, a look of realization crossed his face. "Like spearfishing with a skipping rope, huh?"

She slapped him on the shoulder again, but she started to slightly smile, "Jeff, it's not funny!"

"Like going on safari with a water gun?" He said with a snicker, "It's a little funny, Annie."

He regretted saying this as soon as she seemed hurt, "Because of that experience I had no confidence; after rehab I was a changed person, but I was still Little Annie Adderall, still the loser that none of the boys liked. It was a very tough time for me."

Jeff, a man who rarely felt sympathy or empathy...and it seemed ever only for Annie, reached out and clutched Annie's free hand in his as tears started to form in her eyes. "Annie, you aren't a loser and you aren't Little Annie Adderall anymore...I see the way guys look at you. You're a pretty cool girl."

"Really, you mean it?" She said as the tears she had on deck started to shrink.

"I do."

"Thanks Jeff!" She reached across and kissed him on the cheek, to which he smiled.

"Now you're Little Annie the Unicorn!"

She playfully slapped him for what was at least the tenth time that night as they shared a laugh. When they stopped she spoke. "Don't tell the group, please? They already treat me like a little girl, I don't want them knowing that I'm really a virgin."

"I won't." Jeff nodded his head.

Three fairly uneventful Weeks Later...

*Knock knock knock…*

"Ugh..." Jeff rubbed his eyes with his hands as the sun through his window mercilessly assaulted his eyes, "I'm coming!"

There were a series of rapid, successive knocks at the door, quiet knocks, but he could still hear them even better than usual; it sounded to him like someone was hitting his door with a sledgehammer. He walked through his modest living room, looking over at the couch half-expecting to see Chang asleep sucking his thumb, but remembering that he moved back in with his wife last week; even still, his hangover was horrific, and he made a mental note to never mix scotch and gin again. He heard another knock at the door and reached for the lock, unsealing the deadbolt and turning the handle.

"Jeff!" He heard his name in a girly, high-pitched voice and instantly moved to cover his ears. He looked down on Annie; but it wasn't Annie, or at least not the one he knew. Her hair was wet and tied into a ponytail; she was wearing black Lululemon pants and a tight baby-blue Adidas t-shirt that hugged every curve of her body. She smiled at him with her rows of beaming, white teeth that were whiter even than her immaculate Reebok tennis shoes. She looked fresh and chipper, but most of all she looked very pretty...and not in the typical, subdued 'Oh I just want to pinch her cheeks!' way, in an 'I want to pull you in here by your hair and send you out haggard and drained three days later…' way. Certainly not what Jeff needed to be exposed to at the moment.

"Annie...ugh...do you have any idea what time it is?" He said groggily as it felt like there was an illegal dog fighting ring going on in his head.

She took a second to look at her watch, "Its 1:15 in the afternoon. I've already been shopping and to the gym."

"Those are your workout clothes?", he gave her a rapid top-down look; he shouldn't be doing that.

"Actually just yoga." She blushed, turning on her feet.

"And there's no chance you can't come back later? Like...six hours from now?"

"Jeff!" She pouted, bringing a sharp pain to his head.

"Fine, come in...", he let her in and closed the door, taking a second to ensure that no one saw Jeff Winger let a teenage girl into his place...well okay, a near teenage girl.

Annie skipped in and sat on his couch quietly as he moved to the kitchen to prepare coffee. Once he had placed the grinds in the filter and pressed the black 'Start' button, he entered the living room and saw Annie smiling at him from the couch.

"So how's the sex class?" He asked still standing, surprised when she didn't even recoil at his brazen attitude and boozy breath.

Annie looked down and bit her lip as she sat on the couch, "Not good…"

"Why's that?" Jeff asked, though really it was a formality; in his current state he didn't really care.

"I'm still having trouble…saying certain things." She answered him back.

"But you did so well over coffee a few weeks ago." Jeff said, "Didn't the lesson take?"

Annie looked up at him quickly and looked down again, "That day was different, that was just…"

"Just…?" Jeff attempted to finish the sentence she was struggling with, but failed.

"With just you, it's fine, but it's actually a fairly large class and I really can't say it." Annie said, "and what makes things worse is that the deadline to drop summer courses has already passed."

"So what then? You're going to stop going and take the zero?" Jeff said with a small smirk, but instantly put it away as Annie shot him a venomous glance.

"Really Jeff, does that sound like me?" She asked him, and he nodded in agreement, "I actually came here to ask you for another favor."

Jeff rolled his eyes and sighed; he hated helping others without getting anything in return, but somehow with Annie, who had helped him with his studies so many times, he kind of felt like he needed to help her. This in itself wasn't a bad thing; it was that she knew it and knew how to exploit it that made it deadly. He took a seat beside her on the couch and focused his eyes on her; she was visibly nervous, even moreso than usual.

"I was wondering if…maybe you could come to class with me?" She flashed her biggest and bestest Disney smile at him. Even still, she looked like something else was on her mind, but Jeff felt too crappy to prod her.

Jeff sighed, "You know my policy, Annie; I only spend time at Greendale when I absolutely have to, that means no summer or night credits."

She bit her lip and once more looked down, "Actually…it's too late to get a credit, I was just wondering if…no…"

"Please stop doing that, you're getting entirely too good at it." Jeff said, referring to Annie using anticipation to manipulate him. It's a shame she wanted to go into something like…whatever field she wanted to go into, nursing? She'd make a fine prosecutor.

"If you sat in with me, just a few times, it would really help me." She looked up at him again, "Shirley's there too, it'd be fun!"

Jeff rested his massively swollen head on the back of the couch and let out a deep exhale, "Annie, you know I'd love to…"

She looked at him with excited and anticipatory eyes.

"Actually no, I wouldn't." He started one of his trademark speeches, "I know for you summertime is about My Little Pony and picking posies and learning, exclamation point…but for me it's about making a bit of cash so I can keep my apartment, having fun and…well really anything to remind me that I don't have to go back to Greendale in the fall."

"Oh you'd miss us." She teased.

She readied her tears for him, but he locked his darkened eyes on her, "True, but technically irrelevant. Look, you want so badly to be treated like an adult, well part of being an adult is understanding that there isn't always going to be someone there to hold your hand. Normally that lesson comes with a retainer."

He expected a tantrum and tears from her, so imagine his surprise when she rose and looked at him not with anger or guilt, but understanding, "I understand, I figured you wouldn't anyways." She started, before moving to the door and putting her shoes on, "I need to go run a few more errands; I'll call you later, okay?"

"Sure." Jeff said dejectedly; now how did she do that? Not at all trying to make him feel like crap and yet so brilliantly succeeding? Before the thought could even materialize and disappear into his head, he looked up and heard the quick sound of his front door closing quietly behind Annie. A 'Beep!" sounded from the other room; his coffee was finished. He moved to his barren kitchen and poured himself a cup and took it black, walking back to his room where he would try to sleep off his epic hangover.