Work Text:
“Alright, boys, gather round,” Finn hollers into the frat house, taking a seat on his presidential chair and waiting for the brothers to join him in the living room. Once they’re all seated and giving him their full attention, he holds up the clipboard in his hand. “I just got the list of Kappa pledges, so it’s time for assignments.”
The brothers all whoop in celebration, high-fiving one another as the new pledges look on in confusion. “What’s going on?”
“Every year, as part of Hell Week, the Kappas give us their pledges to use as we see fit,” Puck explains to Rory, grabbing his crotch and tugging, making sure he understands just what he means. “Us brothers each get assigned a pledge, and they have to do whatever we want for the week, or they get dung out.”
“You mean like sex stuff?”
“Isn’t he just precious?” Finn laughs, shaking his head in amusement at the naïve boy. “Yes, Irish, we’re talking sex stuff. This place is gonna turn into a fucking brothel for the next week, so make sure your virgin ass is prepared, because we might even let some of you pledges get a turn.” Turning back to the brothers, Finn clicks his pen. “Now, slave assignments. We have a list of ten pledges here, so some of you are gonna have to share. First up, we have this little hottie, Brittany S. Pierce.”
Finn holds up a picture of the smiling blonde, and Sam immediately throws his hand in air, recognizing her. “Mine!”
“Atta boy, Evans,” Finn laughs, happy to see the boy so eager this year. He had been a bit apprehensive the year before, but he ended up loving it. “Alright, Pierce is assigned to Evans, and you’ll be sharing with Puckerman.” Puck and Sam high five, happy to be sharing a girl again this year. Last year had been a great bonding experience for them.
Finn continues down the list of girls, holding up their pictures and assigning two brothers to each. He’s on the last girl when he freezes, recognizing the name. He quickly flips over her picture and comes face to face with the girl who made his life hell in high school. A wicked grin spreads across his face and he scribbles his own name down beside her, assigning Santana Lopez to himself.
**
“Gather the girls, a Sigma pledge just brought back their assignments,” the Kappa president tells the closest sister, reading over the list as she waits. Soon, the living room is full of pledges, nervously waiting for their first Hell Week task. “Ladies, who is the hottest fraternity on campus?”
“The Sigma Deltas,” one pledge answers, a brunette named Marley.
“That’s right,” president Brooke nods, smiling kindly at the shy girl. “And who’s the hottest sorority?”
“We are!”
Brooke nods. “And in order to be the hottest sorority, we have to be partnered with the hottest fraternity. And we are. The Kappas and the Sigmas have been partnered together for almost a decade, and in order to continue to nurture that relationship, we’ve started up a time honored tradition that you pledges will now participate in.” Turning to her Pledge Educator, Brooke nods at her to take over. “Becca?”
“Hell Week starts tomorrow, pledges,” she begins, taking the page that Brooke hands her. “And while we might have some assorted tasks for you throughout the week, your main task will be servicing the Sigma brothers in any way they require.”
“Servicing how?” Quinn asks, not liking the sounds of this.
“She means sexually,” Santana cuts in before Rebecca even has a chance to answer. “Isn’t that right?”
“Pledge Lopez is right,” Brooke confirms, her face unreadable as her pledges start to mumble their worries. “We sent a list of your names and pictures over to the boys this afternoon, and they’ve all picked out which one of you they want. You will be shared between two bothers, and you will do as they say to earn your place in this sorority, or else you can kiss your membership goodbye.”
Santana glares at her future president, ignoring all chatter from her fellow pledges around her. She holds Brooke’s gaze, not letting her emotions show. She needs to get into this sorority or she can forget about any financial support from her parents, so if she has to suck some frat bro’s cock for a week, then that’s what she’s gonna do.
**
What Santana isn’t counting on, however, is that that dick she’s gonna have to suck belongs to none other than Finn Hudson, the Super Senior she made sure to mock every day for a year. She doesn’t let her surprise show when he steps forward with a shit eating grin and kisses her roughly, claiming her as his slave for the week.
She just lets herself be led to the living room where she’s pulled in front of the entire fraternity, before he pushes her down on her knees and unzips his pants, not wasting a second as he shoves his cock down her throat in front of a room full of cheering assholes.
She takes it like a champ, setting an example for her fellow pledges as they watch on in horror as she’s gagged by Finn’s massive length. She just locks eyes with the boy and lets him fuck her face, taking as much of his cock into her mouth as she can before she chokes.
“Fuck, your mouth feels so good, Lopez,” Finn grunts, fisting her hair tightly and pulling her face forward, forcing more of his cock into her mouth. “So hot and warm, just like I always knew it would. Ugh, we’re gonna have so much fun this week, you and me.”
Santana holds her gaze steady, not letting Finn get the better of her for a second. Wrapping her plump lips around his shaft, she starts actively participating in the act, licking and sucking the underside of his cock, while she pumps his base with her fist. She works him up nice and good, and it’s not long at all until he’s jerking in front of her, Finn’s cock expanding in her grip before it’s exploding, spilling warm cum onto her tongue. She swallows it down dutifully, drinking up every drop of semen he has to offer, sucking on the tip of his dick to make sure he’s empty.
Once he’s done, she stands up and bows to the cheering crowd. “Sorry for the quick show everyone,” Santana laughs, running the tip of her finger along her bottom lip to make sure it’s clean. “Seems Finn here was in a bit of a hurry.”
The brothers laugh at her joke, ribbing their president good naturedly, not knowing that Finn is secretly seething inside that Santana somehow managed to turn this around to humiliate him. He glowers at Santana, who turns around and gives him a wink before she saunters over to join her friends, laughing off their concerns.
He’s going to make her life a living hell this week. He’s gonna get her to break if it’s the last thing he does.
**
After Finn makes an example out of Santana, Hell Week kicks off with a bang, quite literally. Each pair of brothers take their assigned girl up to their room and breaks her in with a good bang.
"Come on, baby, let me see you," Puck moans into Brittany's mouth as Sam tugs at her shirt. The girl pulls away reluctantly and lets the blonde take her shirt off, leaving her topless in the middle of their room. "Fuck, you have great tits." Brittany's head lulls back as Puck attacks her chest, sucking a nipple between his lips and biting teasingly. It helps her to relax a bit, and soon she's moaning as Sam joins in and starts sucking on her other one.
"Oh yeah, so good," Brittany whimpers, running each of her hands over the boys' hair, pulling them closer. They lavish her for a few more moments, helping her get into the the mood, before they pull away and push her towards Sam's bed, sitting her down on the edge. "Do I get to blow you guys now?"
"You sure do," Sam assures her, dropping his pants and pulling out his cock, guiding it towards Brittany's waiting mouth. She takes his length in one go, easily swallowing most of his shaft without a problem, and Sam's knees buckle. "Oh fuck, you're so good at that." Brittany smiles around his member and keeps sucking, bringing her other hand up to wrap around Puck's thick cock and starts pumping.
Puck thrusts into her hand. "Don't forget me, blondie." Brittany immediately pulls away from Sam and gives Puck some attention, deep throating his cock for a bit while her hand jerks Sam off. She goes back and forth between the boys for awhile, sucking them until they're both at full length and Sam is pulling away.
"Take off your pants and kneel on the bed," Sam instructs her, waiting for Brittany to get into position. Once she's on her hands and knees, he gets behind her and lines his cock up with her pussy and slides inside her. Brittany lets out a yelp as Sam enters her from behind, his large size painful to take.
Puck quickly scrambles into position and shoves his cock into Brittany's open mouth again. He kneels back on his heels and just lets Brittany work her magic, her talented tongue sending shivers down his spine. He runs his fingers through her hair and grabs hold, guiding her head up and down his shaft as he watches Sam pounding into her.
The blonde has a tight hold on Brittany's hips, pulling her body back to meet each of his thrusts, slamming into her cunt harder each time. He lets out loud groans as he fucks the girl, his cock sliding in and out of Brittany's tight core. Her pussy feels amazing around his cock, and he shares a laugh with Puck, raising one of his hands for a high five in celebration of their great choice. They could both already tell that Brittany's a better fuck than the pledge they got last year.
Brittany really starts to get into it, and when she starts rocking her hips back into Sam, the boy doesn't stand a chance, and he's coming before he knows it, shooting thick ropes of cum into Brittany's throbbing pussy, bringing her over the edge with him. Brittany moans around Puck's cock as she comes, his thick member choking her as she convulses around Sam's coming cock. She's just coming down from her orgasm when Puck starts gushing into her mouth, his warm cum sliding down her throat as she drinks it down eagerly.
The three of them collapse on the bed together, sated and satisfied, and Brittany is kind of confused about why this is considered a punishment.
**
If Brittany were to ask her, Santana could write her an entire book. While Brittany is loving her experience as a slave, Santana is hating every second of it.
Finn uses every chance he gets to humiliate the Latina: he makes her ride him while he's watching television in the living room, makes her hang off his bed so he can fuck her face until she gags, and gets all the pledges to jerk off into a cup and makes her drink their cum. Any sick, demoralizing thing Finn can think of, he makes Santana do it. She feels sick to her stomach anytime she's near him, but she doesn't break. She knows exactly what he's trying to do, and she'll be damned if she gives him that satisfaction.
So she does what he wants without complaint. She gets on her knees and sucks him off while he's doing his homework, lets him finger her while she's on the phone with her father and puts her four years of cheerleading to good use by fucking him in all kinds of crazy positions. She does everything she can to prove to him that he can't get the better of her.
It frustrates Finn to no end, but then he figures it out one night when they're on round two in his room. He's sprawled out naked on the floor, and orders Santana to sit on his cock backwards, leaning over so her elbows are on the floor between his legs. He grabs a hold of her hips and pulls her back harshly onto his cock, burying his entire length inside her pussy. "Fuck me, bitch. I wanna see you riding my cock until I'm coming inside of you."
Santana bites her tongue and does as she's told, slowly rolling her hips on his dick and creating friction for the both of him. She pushes herself flatter against the carpet so she can arch her back up more, gaining more leverage to sink deeper onto Finn's cock. She puts her all into their fucking, because the faster she can get him off, the faster she gets it over with. And if she manages to get herself off too, at least there's one bright side to this.
Finn lifts his head to watch his cock disappear in and out of Santana's snatch, and when he trails his hands down her ass cheeks with the intention of spreading them to get a better view, he feels Santana freeze. It's not for long, but just enough for him to notice. At first he's confused but when he brushes his thumb over her asshole and she freezes again, it all clicks. He smirks to himself and slaps her ass, the perfect plan forming in his head.
**
His plan has to wait though, because the next day a bunch of the brothers want to have a blowjob competition, each one positive that their slave is the best at it. So everyone gathers in the living room and gets naked, and they face off in pairs of two, the winner getting the night off.
Brittany faces off against Quinn in the first round, her skillful tongue making Sam come down her throat before Quinn can even get Mike fully hard. Brittany gives her a proud smile, licking globs of Sam's cum off her lips, before they move aside and let Marley and Tina have their turn. Tina wins, and then it's Rachel and Kitty, the latter bringing Ryder to orgasm first. Sugar beats Mercedes, and just when Santana is getting ready to take her place, determined to win this so she doesn't have to be at Finn's mercy for a night, the boy grabs her arm and stops her movements, letting her know she's not competing.
"What the fuck, that's not fucking fair!" she argues, glaring at him. "I have a huge essay due next week and I haven't even started it because you won't give me a minute of peace!"
Finn smirks and shrugs his shoulders in indifference. Santana huffs and is just about to sit back down on the floor when his big hands grab her and pull her down on his lap instead. "The show is making me horny, though," he tells her, shifting her to the side so he can unzip his jeans and pull out his already hard cock. "Hop on, Tana. Keep it nice and warm while we watch." Santana snarls at him but does as she's told, reaching down to push her underwear to the side (she's taken to wearing skirts all week, since Finn likes to stick it in her at a moment's notice) before she slides back over and guides his cock inside her pussy. She starts to rock back and forth, but Finn holds her in place, stopping her movements. "Nah uh, just sit there. I just wanna be inside you."
Santana holds in a groan, hating when he does this. Sometimes he just likes to make her sit on his cock so he can be inside of her while he's just sitting around and watching television, like she's some kind of cock warmer or something. It's fucking annoying, and boring, and does nothing to get her off. This time however, Finn reaches around her and shoves his hand up her skirt and into her underwear, clumsily finding her clit and rubbing it in lazy circles. She involuntarily buck at his touch before she catches herself, and tries to keep her composure as they watch.
With the first round done, Brittany and Tina face off, their partners switched out for their other owner, and when Puck spills onto Brittany's tongue before Joe does, Brittany advances to the final round. Finn laughs at just how proud she is of herself, and he bets she's probably the only pledge that will still hang around tonight even if she wins. Finn rubs in tighter circles as Kitty and Sugar take their places, loving the way Santana's pussy clenches around his cock as he massages the hooded nub. He doesn't want to get her off, though, so he makes sure he's just teasing her, pressing hard and then pulling away when she starts visibly responding to his touch.
After Kitty wins their face off, Brittany and Kitty take their places. "Alright ladies, this is it," Finn calls from his spot, and the brothers turn around to look at their president. Santana tenses under their gazes, their knowing smirks telling her they all know Finn's got his cock buried inside her right now. She tries her best to ignore them, and instead focuses on Brittany at the front of the room, noticing the sympathetic gaze directed her way. Brittany knows how much Finn is torturing her, and she's offered to ask Puck or Sam to talk to him, but she immediately shut that down. She nods at the blonde, trying to let her know she's okay. "You have to blow both of your partners this time, and the first girl to make both guys come wins, do we understand?" The girls nod and turn back towards their brothers, each wrapping a hand around their cocks and waiting for the signal to begin. "And, go!"
Brittany immediately starts pumping Sam's cock with her hand, taking his tip into her mouth and sucking. Her tongue swirls around his head and then licks up his slit, and she giggles when he bucks into her mouth. She smirks up at him, knowing just how to get him to explode after all their practice, and doesn't waste anytime this round. She swallows his entire length, deep throating Sam's cock, knowing how much he loves it when he can feel the back of her throat. She bobs her head up and down at a rapid pace, the cheering of the crowd urging her on, and when she starts to gag due to Sam's frantic bucking, she knows he's close. It's not long until he's shooting in her mouth, his delicious ropes of cum sliding down her throat with ease. She wishes she could stay and savor every last drop, but she quickly gulps down as much as she can before she snuffles over to Puck on her knees and takes his thick cock back into her mouth.
With Puck, she knows to focus on his balls. So after wetting his cock with her tongue, she licks down the underside of his shaft until she reaches his testicles, and immediately sucks one into her mouth. She brings her hand up to stroke him with as she tongues his balls, wrapping her lips around the fleshy sack and sucking endlessly on it. She teases it with her tongue before letting it pop out and sucking the other one into her warm mouth and giving it the same treatment. She just barely notices Kitty finishing with Ryder and moving onto Jake, and it spurs her on. Brittany speeds up her pumps and trails her other hand up the back of Puck's thigh, running her palm up and down his skin before trailing her hand up to cup and squeeze his ass cheek, teasingly running her finger over his asshole. He hates to admit it, but Puck is totally into ass play, and she's been slowly working him up all week, hoping to get the chance to fuck him with a strap on before their assignment is done.
"Oh fuck, Britt, yeah, fuck," Puck cries, his balls tightening in Brittany's mouth. "I'm gonna come!" She quickly abandons his balls and moves to take his tip back between her lips so he shoots his load into her mouth. "Oh fuckkkkk yeah."
The crowd goes wild as Puck starts coming in Brittany's mouth, and then Finn shoots off into Santana, her clenching pussy and the blowjob show enough to get him off. Santana cringes as she feels Finn's warm cum filling her up, and just when she thinks she can't hate Finn any more than she already does, he pulls his fingers away from her clit before she can come herself, and pushes her off his lap, leaving her on the floor to leak his cum as he stands up and tucks his cock back in before making his way over to congratulate Brittany on her win.
**
After the events of the day, everyone decides to have a relaxing evening in, brothers spread out around the living room, their pledges heads in their laps lazily sucking them off as they watch TV.
Finn looks down at Santana bobbing up and down on his dick, before his head lulls back and his gaze moves around the room. He smiles when he spots Brittany on her knees in front of Sam, eagerly sucking on his cock while she strokes Puck beside him. She opted not to take the night off, obviously enjoying her assignment this week as much as the guys.
He can't watch for long because he's about to come himself. He turns his gaze back down to Santana, and places a hand on the back of her head, keeping her in place as he starts to buck up into her mouth, moaning as he feels his tip hitting the back of her throat. She gags on him and tries to push at his hips, but he doesn't stop, and soon he's gushing into her mouth, shooting his cum down her contracting throat. He forces her to take all of his load, only letting her go when he's empty, and laughs when she pulls back gasping for air and wiping at her mouth. He smirks at the obvious disgust on her face, only giving her a moment before he motions back down to his crotch, ordering her to start getting him hard again. Santana bites her tongue, swallowing her scathing remark down with Finn's cum, and leans forward, wrapping her hand around Finn's softening dick and working it back up to full length.
**
Hell Week is quickly coming to an end and Finn still hasn't put his plan into action. But when Santana doesn't show up in the mens room to blow him between classes after he texts her, he makes his decision. He's sick of Santana thinking she has the upper hand, seeing that smug look on her face every time she leaves for the night. This was supposed to be torture for her, payback for all those times she humiliated him, but it's not retribution when she doesn't break. Sure, he knows that she really does hate it and all, but it's not as satisfying if he doesn't get to see that shame and humiliation himself. But that ends tonight.
**
Santana enters the frat house with a sick feeling in her stomach. After she missed Finn's text earlier, she knew she'd be in trouble. Normally she wouldn't care and would tell Finn to fuck off, but ever since that night in Finn's room and she tensed up when he got near her ass, she knew he had figured her out. She's been waiting for him to finally go there, to be the first guy to stick it in her ass, but he hasn't. She knows it's coming, though, and as heads turn to watch her walk in, something tells her that the time has come.
"Santana, so good to see you," Finn greets her with a big grin, waving her in. She drops her bag by the door and hesitantly walks passed the crowd, ignoring the leering from the boys and the worried expressions from the girls. Once she's in arms reach, Finn roughly tugs her up and pulls her into his side so they're addressing the group. "I've gathered you all here tonight to witness a very special event! It has come to my attention that little Santana here has never taken it in the ass," he informs the crowd, and they all voice their surprise, while some cheer in excitement, already knowing where this is going. "And since Hell Week is very near and dear to all of our hearts, I can't think of a better occasion to lose your virginity! Who's with me?"
Santana gnaws at her lip as the crowd goes wild, her eyes scanning the huge group of frat brothers cheering for her to get fucked in the ass. It's not like she was saving it for anything special, but she's always been afraid to let anyone back there, and as the crowd gets louder and louder, it does absolutely nothing to quell that fear. "Stick it in her, Finn!" Sam yells with glee, pumping his fists in the air in encouragement. Brittany elbows him in the side, frowning at the terrified look on Santana's face.
"Ah, not me, Evans," Finn says, smirking at the way Santana's head whips around to look at him in surprise. "No, I think it's time we let our pledges get in on the fun, don't you?" Santana's eyes widen and she looks over to the row of boys with lustful, eager expressions on their faces, and the idea of all of them fucking her ass in front of all these people makes her sick.
"Please, Finn," Santana pleads, letting her mask fall for the first time that week. "Come on, wouldn't you rather be my first? I'll do whatever you want."
"You already do whatever I want," Finn grins down at her, the pleasure of Santana begging him feeling better than he ever thought. This was all going perfectly. "This is pay back for everything you said to me in high school, bitch. Now get on your fucking knees and get ready to get your ass ripped apart." Without another word, Finn grabs her wrists and tears her hands away from his shirt, then spins her around and shoves her to the ground. He looks over at the pledges and grins when he spots his Little Brother. "Pledge Irish, get up here!"
Rory isn't sure how to feel, but he knows to always follow Finn's orders, so he makes his way to the front of the room, smiling nervously as all his future brothers cheer him on. "Hiya, Finn."
"You ever fuck a girl in the ass, Irish?" Rory gulps and shakes his head, flinching a bit when Finn slaps him on the back. "Well, this is your lucky day then, because you, little bro, are gonna get the honor of taking my little Santana's anal cherry. How does that sound?"
The pledge glances down at Santana's terrified expression, and then back up to noisy crowd. He swallows thickly, torn, until the crowd starts to chant. "Fuck her ass! Fuck her ass! Fuck her ass! Fuck her ass!"
Santana whimpers, Finn laughs and Rory nods.
"Alright, looks like we got ourselves a show, ladies and gentlemen!" Finn announces to a rousing applause. Noticing Rory's hesitance, Finn takes charge, roughly grabbing a fist full of hair and pulling her towards Rory's crotch, waiting for him to get his cock out before pushing her forward and stuffing his cock in her mouth. "That's my girl," he smirks, pulling her head back and forth so she's deep throating Rory's rapidly growing cock. He glances up and chuckles at the awed expression on the pledge's face. "She's good, huh? Got a great little mouth, this one. Perfect for sucking dick."
Santana tries her best to ignore Finn's words, just lets him guide her head up and down Rory's member. He's actually a lot more hung than she thought, and he's not even fully hard yet. He's difficult to take all of in her mouth, she can't even think about how much he's gonna hurt in the ass. Her hole clenches at the thought of the intrusion, just as Finn pushes her particularly hard on Rory's dick, getting a gag out of her. Finn helps Rory fuck her face until he's at full length, and then pushes Santana onto her hands and knees, pulling her skirt and panties off of her so she's exposed to the whole room.
"Check out that prime pussy, boys," he laughs, turning Santana so her ass is facing the crowd. He steps over her and leans forward, spreading her wide open for the group. "Been fucking this for a week, fellas. Nice and tight, and feels so fucking good coming on my cock." He gives her ass a slap. "But that's not what tonight is about. No, tonight is about this gorgeous ass. An ass this good shouldn't go to waste." Finn runs his finger up Santana's ass crack, stopping at her hole and teasing it. "You know how to prep a girl, Flanagan?"
Rory shakes his head, not tearing his eyes away from Santana's exposed pussy. "No, sir."
"Guess I'll do the honors then." He circles her hole a few more times before moving back to her pussy and running his fingers through her folds. "Oh, look how wet you are, Lopez. You're fucking loving this, aren't you?"
"Shut up," Santana whimpers, shame spreading through her body. She thought she was strong and that she could handle anything, but being this exposed to a room full of cheering assholes, having them all know how turned on she is despite herself, she feels completely humiliated.
Finn ignores her, of course, and coats his fingers in her juices before going right back to her hole, and pressing inside. He's actually a bit less rough than he's ever been with her (he wants to humiliate her, not hurt her), but he's not exactly gentle either, and she lets out a sharp yelp as he enters her. "Come on, Tana, relax or this is gonna hurt." He pauses for a moment and waits for her to stop clenching enough to continue in. It takes a bit of work, a lot of groaning, and even more cheering before Finn has Santana's asshole stretched enough to take Rory's cock. "You think she's ready, guys?"
"Hell yeah!" Puck shouts from his front row seat, his hard on poking Brittany's ass as she sits on his lap and looks on with distress. She cringes every time Santana cries out and really wants to help her friend, but Puck is holding her in place. "Destroy that ass, Irish!"
Finn smiles at his friend and spins Santana around so that her side is visible and the crowd has the best view. He slaps Santana's ass and steps away again, giving Rory full access. "Have at her, big guy. Give the audience what they want."
Rory eyes Santana's stretched hole and gulps, nervously stepping up to her. The crowd seems to hush down as he gets into position behind her and copies Finn's earlier actions, running his fingers through Santana's sopping pussy and collecting some of her juices to spread over his aching cock for lubrication. Once he's ready, he uses one hand to grip Santana's hip, and the other to guide his cock towards her hole. He takes a deep breath and presses his tip against her hole, feeling her tense up immediately. He actually feels a bit bad for Santana, even though he knows how horrible she was to his Big Bro, but when he sees Finn's encouraging nod, he shakes it off and presses forward, pushing passed Santana's tight ring of muscles and popping the head of his cock into her asshole.
"FUCK!" Santana cries out the second Rory enters her, searing pain spreading throughout her body. It hurts just as much as she thought it would, and feels tears springing to her eyes. She risks a glance over at Finn, and the second she sees that smug, satisfied look on his face, she knows she can't let herself react like that again. No matter how much this hurts, no matter how humiliating it feels to be mounted like a dog by some virgin loser in front of a room full of cheering douchebags, she can't let it get to her. Santana gulps down and sucks her lip between her teeth, determined to power through the pain.
Rory meanwhile, is just trying not to bust his nut already. Santana's ass feels so fucking tight and amazing, easily the best thing his dick has ever been in, and as he slowly slides further inside, it takes all of his concentration not to blow. The brothers would never let him live that down. Finally, he bottoms out in Santana's ass, and he looks down where Santana's cheeks are flush against his hips, amazed that his entire cock is in her ass right now.
"Go Irish!" Sam calls out. "Now fuck the shit out of her!" The rest of the crowd howls in agreement, and it's all the encouragement Rory needs. He slowly starts to pull out, feeling Santana's asshole clenching and unclenching around his shaft, before diving right back in.
Santana manages to hold in her yelp this time, but it's no less painful. She squeezes her eyes shut as Rory starts to pump into her, slowly but steadily picking up his pace until he's pounding her ass roughly. She's jolted forward each time he slams against her, and she eventually falls to her elbows so she can arch her back, the pain finally starting to make way to pleasure. "Jesus," she mumbles, one particular thrust hitting her in a nice spot. She starts slamming back into him, trying to take some control of the situation and maybe find a way to get off on this after all, but she barely gets a chance to before she feels a hand roughly pulling her head up by her hair.
"I was getting bored," Finn smirks down at her, unzipping his pants and pulling his erection out. "And hard. No use wasting that pretty little mouth of yours, now is there?" Santana barely has time to register the situation before she has Finn's cock stuffed in her mouth, the boy making quick work of thrusting into her face. It takes her a moment to gather her barrings, and she pushes herself back to her hands, positioning herself better to take both cocks as best she can. Finn still has her by her hair and he's guiding her head up and down his cock, so she just has to kneel there and take it from both boys. "That's a good girl," Finn coos, fighting the urge to lull his head back as he feels Santana's hot mouth sucking his cock. No, he's enjoying the show far too much. "You're gonna swallow my load like a good little slave, and then I'm gonna open the floor up to volunteers, how does that sound?" It sounds fucking awful to Santana, but she's not in the position to protest.
"I'm not gonna last much longer, mate," Rory huffs out, tightening his hold on Santana's hips so he can fuck her harder. He leans further over her, slamming down into her at a steeper angle, and all it takes is one more clench from the girl and he's exploding, shooting his load into Santana's ass. "Oh fuck!" Santana moans around Finn's dick as she feels Rory's warm cum filling her up, his stilled movements keeping it stuffed inside of her. The crowd erupts in applause as Rory keeps still for a moment before he starts to pull out, watching in awe as Santana's pulsating asshole slowly starts to leak his sticky cum. "Wow, that's so hot."
"Maybe you can come back for second," Finn tells him, noticing one of the other pledges eagerly awaiting his turn. "But don't hog the slut, let your fellow pledges have their turn." Finn watches as Rory quickly moves out of the way, making room for the next pledge to take his place behind Santana. "Look at me, Santana," he orders, tilting her head up until her watery eyes lock with his. "I wanna see your face when he sticks it in you."
He's filled with absolute glee when Santana's eyes bulge out of their sockets as the pledge buries his cock in her ass.
It still hurts at first, but this dick is actually easier to take. Her ass is already stretched, this guy's cock is thinner and a bit smaller, and Rory's cum assists in his thrusts. She thinks he might be a bit more experienced too, because he's not as clumsy, and she's actually getting off this time. He's fucking her hard though, and each time he slams into her, she feels Finn's cock hit the back of her throat, and it's not long before he's coming and filling her mouth up with cum. She tries her best to gulp all of it down, thankful to finally get Finn away from her.
The joy is short lived though, when his cock is immediately replaced, and she looks up to find Puck kneeling in front of her, a huge grin on his face as he shoves his dick into her mouth. She reluctantly takes his unbelievably thick member between her lips, and immediately gags on its size. She has no fucking idea how Brittany's been taking this thing all week long. He's just as rough with her, and she's so busy trying not to choke on Puck's cock that she barely registers when the second pledge comes, adding another load to her ass.
There's hardly any time between pledges, and her ass doesn't get a moments rest. This third pledge is definitely experienced, and she wishes she could look behind her to see which one it is, because as he thrusts into her, he reaches around and rubs her clit, finally giving her some release. She comes around his cock, her asshole clenching and pulsating around his member as she spasms between the boys.
"Ugh, fuck, Lopez, you're gonna make me come already," Puck moans, even able to feel her vibrations from his position in her mouth. He pulls out of her mouth and fists his cock, pulling it up. "Suck my balls, baby," he orders, and Santana cringes but does it anyway, reluctantly tilting her head to the side and sucking one of Puck's testicles into her mouth. She tongues the loose skin, ticking it with her tongue, not really sure what he's looking for. It seems to do the trick, though, because before she knows it, Puck is shooting ropes of cum onto her face, his thick stream covering her. "You look so fucking hot with a Puckasaurus facial, baby." He leans down and kisses her roughly before he moves out of the way and lets Sam have his turn.
Santana loses track of how many guys she blows and how many pledges fuck her from behind. It's all a haze of cum, orgasms, cheers and a lot of shame. It seems to go on for hours, Finn making Quinn and Rachel lick her clean before they start all over again. Eventually Santana's ass is too gaping to get anyone off, so Finn makes her get on her back and offers her pussy to any brother that hasn't had a shot, or who just wants seconds. She remembers Brittany trying to step in sometime around then, but Puck and Sam held her back, forcing her on her knees to suck them off herself
Santana's completely wrecked by the time Finn finally decides to give her mercy and end it, spread out naked in the middle of the frat house, aching and oozing multiple loads of cum from all of her gaping holes. She can vaguely hear the clicking of cameras going off, and she cracks an eye open to find a bunch of guys taking pictures with their phones. She feels a brand new wave of shame hit her, and she can only imagine what they're going to do with those.
"Don't worry, baby," Finn coos, kneeling down beside her as the crowd slowly starts to trickle out of the room. "I'll make sure the guys only use those pictures and videos for their personal collection."
"Videos?" she croaks out, horrified.
Finn laughs. "Oh, you didn't notice everyone filming it? I bet we could put together a full length film with all the ace footage we got tonight. Make some big bucks"
"Please, please don't." This is what Finn has been waiting for. Santana is finally broken, completely miserable and begging him. And yet, it's not enough.
"Mmm, we'll have to see what it's worth to you," Finn muses, reaching down to finger her overflowing pussy, laughing as more cum is pushed out of her. She immediately jumps at the touch, her cunt beyond sensitive after being fucked all night long. "You see, I wanted pay back for all those times you humiliated me in high school, and I just don't think a week is enough time to make up for it. No, you made my life hell for a year. Doesn't seem like a fair trade to me."
Santana feels panic creeping up, knowing that Finn wouldn't hesitate to spread those videos and pictures everywhere to ruin her life. "Please, no, please, please, please, please don't," she sobs desperately.
This is more like it. This is what he's wanted, Santana broken, desperate, terrified and exposed. Just like she used to make him feel every day. "Calm down," he shushes, running a soothing hand through her tangled hair to falsely reassure her before he roughly shoves a second finger into her sore pussy. "I'm a reasonable guy, I think we can work something out. Why don't you take the weekend to rest and we can talk about it next week."
"Next week?" Santana whimpers, her stomach coiling as Finn fingers her sensitive hole. "But Monday..."
"You didn't think I was really gonna let you go after just a week, did you?" Finn laughs, his thumb slipping through thick cum to find her clit. He presses down and immediately feels Santana clench around his digits, coming for what might actually be the fifteenth time or something. He lost count somewhere around the second time she squirted.
"Fuck!" she cries out with a sob. Her body is so fucking sore, she can't take any more.
He leans down to whisper in her ear as he forces her orgasm out of her. "You made my life hell for a year, Santana," he snarls. "And now that I have all those great pictures and videos of you getting used and fucked by countless guys? Well, something tells me we'll be able to start evening that score now." Finn adds a third finger and picks up his pace, not giving her a second to recover, already eyeing the sixteenth orgasm. "Welcome to Hell Year, bitch."