The Big Fucking Nerd (Patreon)

The highly voted story of a big titty nerd girl asking her friend to help her lose her virginity. Sort of a big combination of pieces of old ideas, between Geekdom and assorted other characters. Late in the story, I found myself thinking of Gats' red-haired "as your childhood friend" character as a vague mental image. Debated a lot of body types with her, but massive fucking tits that were clumsy as shit on her was always the focus for Annabelle.

She also mainly goes by Annabelle, because that's the nerdiest version of her name. Anna's ok shorthand, and Annie is either too cool or it makes her made that you're referencing the prequels.

“So what did you want to do this weekend?”

It was a pointless question, really. Annabelle never had plans for her weekend. She was the most blatant nerd Matt had ever met. She had bushy red hair, huge thick glasses, braces, and a short, scrawny twig of a build. They became friends after they were partnered up in class. She was into some of the same dorky stuff as Matt, but more extreme about it and way more blatantly. Getting to know her, he found she was sweet enough if kind of obsessive and easily flustered.

It also revealed that she had massive boobs. The brace faced geek wore a lot of baggy sweaters over her nerdy tees, and even then it was mind blowing to learn she managed to conceal them for so long. Her looks certainly didn’t make you think she’d be packing some firm watermelon titties.

“I dunno. Video gamesh, painting shome minish, check on my algae reshearch, check out the new harem anime… y’know. Whatever….”

Anna sat on her bed, lisping out her ideas and kicking her short and scrawny legs off the side. She was in a long skirt and  a tight gray t-shirt with a faded Death Star over the chest. It looked even more faded than it was designed to be with how stretched and distorted it was across her chest. Matt sat at her gaming chair  in front of her high-end computer and desk covered in tabletop and anime paraphernalia.

“Yea, I wasn’t thinking of anything special. You wanna go to the park and try out that new mobile game…”

“Uh! Err! No!” Anna hastily and desperately denied.

It immediately struck Matt as weird. Even when they were arguing about sci-fi hypotheticals, it took her a while to get heated about anything.

“I, uh, thought we could shtay inshide and uh… do inshide shtuff.”

Matt frowned at her suspiciously. The busty toothpick of a young woman blushed and sweated more than usual under his stare.

“Like what?” he pressed warily.

“Like uh… that shtuff I shaid before. Or… try out one of my dating shims or uh… losemyvirginty.”

Annabelle squeaking out the last idea as she avoided eye contact didn’t keep Matt from catching on. He went wide-eyed at even the sheepish proposition.

“Wait, you’re a virgin? I mean, of course you’re a virgin. You’re a nerd who can’t keep spoilers from me let alone secrets.  But still, you’re a virgin?! Look at…”

Matt gestured towards chest.

“You mean theshe pain in the asshes? They keep squishing my minish and knocking over my figuresh.”

Anne frowned and hugged her arms self-consciously over her chest. Her tits squeezed together and bulged out over har arms. She certainly didn’t seem to think of them as a blessing from all the times she’d complained about them bumping into things. Matt was among those things on several occasions when the clumsy redhead tripped into him.

“I’m the nerd virgin to a chad Matt. What’d you expect?” she sighed.

“No way though. What about the last cosplay you did for that convention? Nobody hit on you there?” Matt pressed.

“I chickened out! I couldn’t wear that in front of all thoshe people! I wouldn’t be canon! 2B’s got a big booty! They’d laugh my shkinny assh right out of the con.”

They absolutely wouldn’t have. Annabelle had a lot of glaring flaws and outstanding quirks, but Matt had always thought of her as cute in her own weird way. She had shown him the skintight cosplay and done his best to stifle his boner the entire time.

“I mean… I thought you were cute in it. You’re cute a lot of the time. No way nobody’s hit on you yet.”

Annabelle itched at her mass of frizzy red hair before brushing it out of her face. Her big green eyes looked even bigger behind her large glasses.

“Y’mean it? Cuzsh I’m no cheerleader or shupermodel or nothin’...”

“Who cares? They’re vanilla,” Matt insisted, sitting on the bed next to her. “Remember when everyone was horny over that ‘It’s Not My Fault’ chick online?”

“Tomoko,” Annabelle quietly and curtly corrected him.

“Right. The normies pair up and that’s fine. A lot of guys want somebody who stands out. And you do that. As soon as we met, I knew you’d stand out in a crowd no matter how much you hunched over or aced your science projects or tripped over yourself.”

Annabelle was already hunching her shoulders, fidgeting with her fingernails as she glanced at the floor. Her feet shuffled over the carpet before glancing up at him.

“Do you real… aw, slag!”

They both realized her glasses had fogged up from her heavy breathing and made them almost completely opaque. Matt had to snicker as Anne blushed and pulled them off. She hastily pulled up on the bottom of her already drawn tight shirt, flashing Matt her underboob and dark purple bra as she rubbed her glasses clean. She barely bothered to fix it in her haste to look back into his eyes through her glasses.

“Do you really think I’m cute? A hot guy like you?”

Matt sighed and took her by her shoulders. It mashed her expansive bosom against his chest and inner arms just to do so.

“Ann? You’re cute as hell and any guy would be a total asshat not to want to help you get rid of your v card.”

Ann squirmed a little in his grasp but made zero effort to move away. It wiggled her huge tits around between them.

“You promishe?” she asked uncertainly.

Matt rolled his eyes and met her lips with his, kissing her as best he could over her huge rack. He had to squash her chest back against her chest and she let out a muffled squeal. Even with her boobs and braces in the way, it still felt… nice. Anna’s wide nipples hardened enough to prod at his chest. When he pulled back from the gentle but drawn out kiss, she was bright red between her freckles and her glasses were freshly steamed over.

“Wowzersh,” she lisped.

Anna didn’t bother cleaning her glasses off, taking them off just so she could see. Which defeated their purpose but she couldn’t think too clearly with her desperate virgin sex drive firing up.

Her brown eyes fluttered before puckering up and leaning in for more. Matt swallowed, surprised that their quiet weekend had suddenly gone this far. He wasn’t about to back down from such an offer from his geeky friend and met her lips again as their first kiss turned into their first makeout session. The occasional brush of her teeth and braces against his lips made it a little awkward but nothing he couldn’t quickly shrug off as Anna being Anna.

His hands reached out to his nerdy friend’s sides, wanting to work his way up to her tits like they were dessert. He underestimated the size of her wiggling bust as they bobbed into the way of his hands, filling them with the fat warm flesh behind her stretched out shirt. Annabelle squealed nasally at the touch and bit down on his lip, raking the braces of her front teeth against his face.

“Fucking jinkiesh,” she hissed, panting as her parting lips drooled a little over Matt’s mouth and shirt.

Her heavy breathing puffed her breasts in and out, bumping them against his hands and chest. They swayed enough even within her bra that the hard nipples rubbed between his fingers. Matt pinched them curiously and watched as Anna’s eyes went wide and her mouth hung open even wider.

“Ohmigosh! Ca-careful! I’m gonna…”

Matt smiled. The squirmy virgin’s overreaction was honestly adorably overrated.

“Nah, trust me. It gets better than just teasing your nips.”

He still enjoyed her response, so he kept massaging his overflowing handfuls of her tits. He slid his hands under her Star Wars shirt and lifted it up over her head. Anna’s awkward grunts and squirming actually helped get her out of her top, going for her painfully plain bra next. The huge, pale, freckled-spotted flopped out and the direct contact with his hands and her hard nipples and wide areolas made her let out a long and warbling mewl.

“Ohhhh gosh that’sh good~!” she whined, biting her thick front teeth into her lower lip to flash her braces in mindless pleasure.

“Oh yea? You think that’s good? Let’s see how you like this?”

It felt hard not to tease Annabelle when she clearly liked it so much. Matt lowered his head to cup her tits and set his mouth on one of her nipples. He ran his tongue over the hard nub, making sure she could see it as she stared wide-eyed at his oral handiwork. He pinched his lips around her tip, sucking noisily while he pinched the other. Anna broke into another nasally squeal as she tensed up and shuddered aggressively. Her huge boobs bounced around against his face like he was being bumped by a pair of boxing gloves. She kept up her nasally moan until she flopped forward, flopping her heavy tits into his face limply enough that he had to catch her.

“Fucccck that wash amazing… jusht like in the hentaish,” she cooed as she slumped her arms over his shoulders.

“Wait… on fucking way,” Matt insisted to the ragdolling nerd as soon as he had the room to breathe outside her cleavage.

Anna pursed her lips and shifted her legs, rubbing her thighs together. He ran a hand down her thigh and felt under her skirt. Her panties were soaked and warm with her tits-only orgasm. He smiled at the implications, even as she wriggled and her crotch rubbed against his hand like she was looking for more attention.

“Wow… you are SUCH a virgin,” he laughed.

“Shtaaaahp! Like I’m not awkward enough about it! Sheesh!”

“Nahhh, it’s cute! You’re seriously that horny for me? Or is your clit just hardwired to your nipples?” Matt insisted with a massive grin on his face.

He slid his fingers past her panties, spotting the moistened Spider-Gwen face on the crotch of her underwear. He rubbed at her mound underneath, feeling the thick and untamed red bush poking out at the edges. A big swollen clitoris poked out between her pussy lips and she nearly jumped when he touched it. Her hands shot down to cover herself up in a fumbling grasp.

“EEEP! EASHY! It getsh touchy after I shquirt!”

“You do know squirting’s just in pornos, right?”

“What?! No way! It’sh real!” she insisted, getting red faced with enthusiasm rather than embarrassment.

“I jusht need a shec to cool off… ooh! I alwaysh wanted to try thish!”

With her top already off, she eyed Matt’s crotch and started to run a curious hand along his bulge. She just started to fumble with his zipper before he gladly helped her out.

“I got it,” he assured her, undoing his pants and popping his cock out.

He was fully hard from their fooling around, and he caught Anna licking up some drool too late. It dribbled onto her breasts as she tried to fix her glasses that weren’t even on her freckled nose any longer. She tried to brush it off as she leaned forward on her knees, dropping her tits into his lap. Matt grunted heavily as the soft but heavy funbags surrounded his member. She adjusted them to fit it more comfortably, but even that just meant her rubbing around his cock.

“That good? You aren’t jusht teashing me again, right?” the meek geek asked, looking up at him through her messy hair and brushing some out of her eyes.

“Definitely not. You’re so hot. The hottest nerd I’ve ever met by far,” he moaned, rubbing the top of her head softly.

Anna cracked a toothy grin, clearly appreciating the comment. She tipped her head lower into his lap, sticking out her tongue and clearly trying to suck his cock. It was just adorable to watch her struggle and fail to reach it with her big tits in the way. They swallowed up his dick and left none for the rest of her, awkwardly trying to push her big clumsy boobs out of the way. She only managed to push her face into her own freckled, sweaty cleavage and plant a smooch on the tip, which still got a grunt out of Matt as he thrust up to meet her. It popped into her mouth and her lips latched around it, sucking like a piece of candy for a moment before he sank back into her boobs. Her awkward titjob mixed with her awkward blowjob, both endearing, amusing and arousing as she did her best to please him on all fronts. She kept glancing up to make sure he was still moaning and enjoying her sloppy BJ, grinning now and then at him. It brushed her teeth and braces against his hardon in the process but he was too hard to care as they brushed off the firm flesh.

He ran a hand through her hand, stroking her head and face as she did her best. What she lacked in experience she made up for with enthusiasm, a not-so closeted perversion, and giant tits. She slurped his cock as his hands roamed over her body, exploring his friend’s bony body. He started to tug down her skirt and Marvel panties as she rubbed and clapped her boobs around his erection. With most of her pasty freckled body exposed, he only had to squeeze her hips out of her skirt and wet panties until she was fully naked on the bed with him. She moaned and mewled, even mooing a bit with his dick caught too deep in her mouth to speak clearly (if her lisping could be considered clearly). She finally popped his drool-coated cock from her mouth and boobs to wipe her mouth. Matt spotted a hand had snuck between her legs, rubbing her bushy pussy.

“Starting to get back into it too, huh?” Matt asked.

“Mmhm,” she squeaked, giving another meek lick up his cock.

The flick of her tongue happened to hit a sweet spot right below his cockhead. He groaned and arched his back, pressing his dick into her face and pulling at his handful of her messy hair. Annabelle gasped and jerked in a strong response to that, going beat red as he felt her heart racing through her huge tits.

“Wowshersh~! I didn’t know you could be shuch an alpha chad, Mattie,” Anna muttered, batting her eyes up at him.

Matt ran his hand along her ass curiously. He could feel the heat radiating off her pussy and the wet arousal dripping off her. With her skinny but busty body on all fours in front of him, he couldn’t help but want to deliver on her horny hopes now that she was ready for another orgasm.

“Oh sure. If you’d wanted, you should have just asked.”

Matt caught her by surprise, reaching under her and grabbing her by the legs. Anna gave a surprised squeal as he flipped her onto her back, the top-heavy and very unathletic girl going down with laughable ease. It was just as easy to lift up her scrawny lower half and raise her legs until her feet were nearly down by her head. That sent her tits flying up after her, flopping up and slapping herself in the face before the drooped into either direction. They dropped apart in his grasp, spreading out her tight virgin pussy as best they could.

“Oh gosh! Careful, dude! I get dizzhy eashy! Ohhh~!”

She moaned as Matt rested his leaking erection on top of her slit. That alone sent a pulse of pleasure down through her spine, licking her lips as she watched him set her up.

“Ish that a mating pressh? Like from that Shaber doujin I shent you?” she asked quietly.

“You know it,” Matt said as he lined up to push down into the skinny redhead.

It wasn’t like he had ever done this position before, but there was no way uber-virgin Annabelle would know the difference. He slid his dick inside her, taking care at first knowing how tight she’d be. That just made it more intense for the both of them. As soon as his cockhead pushed against Anna’s clit and slid inside her, she moaned and bit into her knuckle to vent some of her overwhelming arousal. It was such a hot sight that Matt couldn’t help but thrust the rest of the way inside her. She fit like a glove, both of them moaning now as he fucked his nerdy virgin best friend.

The first thrust alone made her eyes roll back, her body shaking enough that her tits wobbled like they were two fleshy mountains in an earthquake. They bounced around on either side of her face as Matt kept pumping into her. She was tight but wet and willing from her previous orgasm, lubing up her friend’s thrusts as he helped relieve her of her virginity.  Anna gawked and wrapped her skinny legs around his waist, trapping him inside her and shaking her head to toss around her wild hair.

“Yesh~ ! Shhhit~! Morrrre~!” she moaned, her lisp even tainting her dirty talk.

Her spittle peppered Matt’s face and chest, but he was in a lusty frenzy at this point. Watching the skinny and somehow jiggly nerd getting plowed by him, his thrusts trailed by the wet squish of her tight snatch, he leaned in close and kissed her firmly on the lips. Her tangled hair tickled his face as his tongue ventured into her, plugging up two of her orifices at once. Annabelle clumsily clawed at him until she had her arms around Matt’s neck and her fingers in his hair. As he fucked her faster, the busty redhead rapidly squeaked into his mouth like a mouse riding a jackhammer. Her freckled face beat red, Matt grunted back heavily and came inside her. The rush of creamy heat flooded her snug pussy and made her vaginal muscles tense around him excitedly. Her excited grip hugged his cock briefly before she shook again, eyes rolling and mouth hanging open came harder under his pinning position.

Anna sputtered breathlessly into his mouth before she fell back, wheezing heavily as she laid limp on the bed in his grasp. Matt’s mind fluttered with post-nut clarity and he reached for the dresser, passing Annabelle her inhaler. She took a couple puffs before she let out a wheeze that whistled through her teeth.

“Shhit, dude… way to crit my clit like a champ!” she panted, wiping some sweaty hair from her face.

Matt just chuckled and kissed her breathless lips, getting them to break out in a weary smile. He eased himself back down to his haunches, letting Anna lay down in a more comfortable position.

“Glad to help. So how’s it feel now that you’re not a virgin?”

Anna puffed a sigh that blew more messy hair from her face. “Kinda… like I want shome more,” she said with a meekly impish grin.

Matt ran a hand lazily over her crotch. Her clit was even bigger than before, excited to a peak. So when he brushed across it she hooted and shuddered.

“Okay okay! Nevermind! I’ll cool it! Jeesh!”

She flopped back to the bed, shivering a little longer as Matt cuddled up against her, feeling her huge boobs cushion him from the rest of her boney body.

“Though… shince you mentioned the cosplay, you think we could get shome coshtumesh into thingsh next time. Or shome roleplay like I ushed to do on shome shervers…”

Matt laughed at her already geeky ideas leaking into her newly budded sex life. Still, her already talking about a next time warmed his heart a little and excited his erection back into motion.

“If it’s with you? Anything you want, you big fucking dork,” Matt mused to her, planting another light kiss on her lips. That alone triggered another excited shiver in the inexperienced nerd girl.

“Emphasis on the ‘fucking’ part,” she sighed a bit proudly.