Just Say No To Asscrack

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Santana's new project: taking Rachel Berry's anal virginity.
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Zev95
Zev95
1,580 Followers

Author's note: This is a story based on Glee. It takes place during the later seasons, when both the actresses and the characters in the story are over 18.

*****

Rachel came back from her hourly bathroom break to find her leadership had been missed on the group project. Brittany was now on Santana's lap, and her tongue was in Santana's mouth. If she'd had to do number two, Rachel felt sure her previous thought would've been reversed.

"I left to tinkle with the assurance that you would be developing Austro-Hungary's dancing style? Honestly, it's like you don't even want to catalog the build-up to World War 1 through interpretive dance with every country being represented as a different member of Glee Club with their own individual aesthetic!"

Santana restrained herself to just massaging Brittany's thigh under her red skirt. Rachel should've known something was up when they both showed up at her house in their Cheerio outfits. "Honestly, Ratchet, you're such a control freak, we thought you'd just do all the work and when it was mediocre, as usual, we could send the teacher nudes for a passing grade."

"First of all, my work is outstanding. Secondly, don't call me Ratchet, that word and Rachel are not even from the same root language!"

Brittany stooped to whisper in Santana's ear.

"Please stop straddling her," Rachel insisted. "That couch was designed to only hold one person per cushion. You are stressing its limitations."

Santana grabbed Brittany's ass and pulled her even closer. "Tell you what, Woody Allen. I keep making it with my girlfriend and you watch, then you can do the work for all three of us."

"That sounds reasonable to me," Brittany agreed.

"It was your idea!" Rachel cried.

"Huh? No, I was just whispering to Santana that I miss Digimon. I wish Japan would bring that back."

Rachel crossed her arms. She'd gotten exceedingly good at it. "Ms. Lopez, my fellow student—if I wished to observe you in Sapphic coitus, I would just have to be in the third floor bathroom in the east wing during lunch period."

"Oh, so we're bargaining now? I know you're Jewish and everything, but turning down me and Brittany making sweet lady love to each other is downright Chinese."

"Your ethnic humor won't get me to do this project all by myself!" Some people could double-knot their shoelaces. Rachel could double-cross her arms.

"Alright then. How about we let you join in?"

"Join in? On the coitus?" Rachel got into character so deeply, she actually felt a bead of sweet rolling between her shoulder blades.

Santana pushed Brittany off her lap, splaying her legs in invitation. "Yeah. You. Me. Brittany, if you can handle both of us. What do you want, Manhands? Ready to leave the tribe of virgins?"

"For your information, I am not a virgin. I lost that particular social construct in a very loving, intimate setting during which Finn and I consumed many non-alcoholic beers and professed our feelings at length."

Pinching her hem between two fingers, Santana began to tug one side of her skirt slowly upward. Brittany pulled up on the other. As much as Rachel doubted the feminist implications of the story of the Garden of Eden, it looked very much like there was a certain mythic snake at Santana's crotch, having the material of her skirt pulled over it.

"Yeah, no shit, Rachel. It's the new millennium, everyone's lost their virginity. Even Artie's gotten fucked, and his dong doesn't even have a bone in it or whatever. I'm talking about your backdoor virginity. Only the cool kids take it up the ass."

"I like this plan," Brittany said. "I'm excited to be a part of it."

She got up and stepped over the couch, leaving Santana to pull her skirt over her strap-on on her own. Rachel watched out of the corner of her eye as Brittany picked the camera off the piano and moved it in closer, to capture Rachel's nervous look as she regarded the eight-inch dildo affixed to Santana's crotch by a Gordian knot of dominatrix straps.

She was pleased with her own acting prowess, actually feeling excited as Santana rose from the couch and walked over the coffee table toward her with a menacing grin on what the politically incorrect would dub an exotic face. Rachel backed up, eventually hitting and falling into one of the living room's easy chairs.

Santana stood over her, hands on her hips, subconsciously pointing at the dildo that was itself aimed at Rachel. Rachel felt a fire deep in her sex as she counted each of the strap-on's eight inches off in her head. She was glad that Santana hadn't lied and it really was the smallest one in her collection.

Suddenly, Santana grabbed Rachel's arm and yanked her up roughly from the chair. Then she pushed her over to the coffee table, sweeping away all the Highlights magazines with her supremely flexible leg, and shoved Rachel down so that she was on her stomach across the glass. When she tried to sit up, Santana slapped her across her ass.

"Stay down, Zion! I'm gonna fuck your little virgin ass!" Santana said.

Rachel argued as if she were in a classroom debate, even as Santana pulled down her tartan skirt. "You can't do that, Santana," she said, quite logically, "your dildo apparatus is simply too big. It would injure me."

"Hey, super-bitch, you think Brittany keeps an economy-sized bottle of Vicks VapoRub in her purse because she has the black lung?" Santana held out her hand. "Give it here, Britt."

Brittany tossed it to her, still filming, and Santana caught it smoothly, digging up a big wad of the cold smile and slathering it on Rachel's ass from cheek to cheek, even shoving it into her hole with her fingers. Rachel's face contorted and grimaced, feeling a sensation that would be entirely new if she hadn't sat on her aunt's potato salad when she was twelve. Those were her rebellious years.

"I love popping cherries, Mom Jeans, and I'm good at it. After I did your little girlfriend Quinn, she could've moved ten keys of coke in her nonexistent white girl ass. The only problem is, just fucking my cheerleader bitches and their tight little asses gets old. I wanna fuck your great, big, rap-video ass now. See all that kosher meat fly while I jam my cock in!"

"Firstly!" Rachel roared. "Quinn and I are just good friends!"

Santana pulled Rachel's asscheeks far apart and shoved her huge, eight-inch strap-on into a virgin asshole.

"Secondly, HOLY SHIT!" Rachel screamed in pain and shock as Santana took her anal virginity mid-sentence. She couldn't even feel the tip of the dildo, just the unrelenting pressure behind it. Solid want made physical—it needed to get inside her. She screamed as Santana tried to plunge the entire rigid dildo inside a body that was only meant to take in artistic greatness and vegan food.

"Oww! OWWWWWW! No, don't, you're killing meeeee!" she whimpered, rather convincingly. Meryl Streep should act so well.

Rachel raised her torso, desperately trying to shake Santana off her, but the cheerleader had her pinned face down to the coffee table. Santana got a rough hand on the back of her neck and shoved Rachel's face down into a Reader's Digest. She cried tears of pain and rage into Humor In Uniform.

"Oh, God, Santana! Stop, please stop! It hurts soooooo fucking much! You're tearing my ass apart!" Rachel screamed. Method acting. It felt like there were a pair of fingers in her asshole, pulling her open from this angle and that as Santana worked the dildo around, prying Rachel open.

Santana chuckled huskily. "What do you think, Britt? Should I stop fucking her ass?"

Brittany was sitting down again, madly finger-fucking herself as she taped the sodomy with her free hand. "I don't know... when you first ass-fucked me, I thought I'd sat on a bowling pin again. I begged you to stop fucking me too, remember?"

"Yeah, I remember all right," Santana grinned, shoving more and more of her strap-on up Rachel's little ass. "And I didn't stop for you, did I?"

"No, you fucked my ass even harder!" Brittany giggled. "But you said that before long, I would begin to enjoy it. And you were right. After a few minutes, I really liked my first ass-fucking. It's a precious memory, like when I got Lord Tubbington."

"Hear that, Adam Sandler, star of the hit film Jack & Jill?" Santana asked as she ground her strap-on into Rachel's asshole, feeling her muscles hugging the dildo tightly. "Brittany loves getting ass-fucked. And look at her tight little ass. She has way less room for a cock than you do!"

"Yesssssss, but it just hurts so muuuuuuuch!" Rachel wailed. She could feel her ass clenching, the muscles working as one to push out this intruder, and the steady pain as each failed in turn.

"Stop whining!" Santana yelled as she slapped Rachel's ass. "Tell her again, Britt! Someone wasn't paying attention!"

"It's a precious memory, like when I got Lord Tubbington. It was my third time taking sixth grade—"

"About the sodomy!"

"Oh. Well, all I know is that you just have to relax, Rachel, and then you'll start loving it too! Just as much as getting it in the vag... but not as much as the mink gloves." Brittany said it still plunging her fingers in and out of her pussy.

"You hear that, Simon Cowell? Just relax and let me fuck your ass!" Santana yelled.

Rachel groaned, knowing that she was entirely at Santana's mercy. There was absolutely nothing she could do. She couldn't get away and no matter how much she begged Santana to stop fucking her ass, she wouldn't. It was as if Santana wouldn't stop until she had dumped a load of cum right up her asshole, as impossible as that was.

Stay in character, Rachel thought. At this point in your emotional journey, you're thinking that you're entirely at Santana's mercy, that there's nothing you can do, that you can't get away and that no matter how much you beg, Santana won't stop fucking your ass. It's just like your character's grandparents in Croatia, during the terrible wars. Take strength from Babushka and Pop-Pop. There's no use in fighting, just try to relax and maybe it won't hurt so much.

Santana slipped her cunning hands under Rachel's soft body and pinched her nipples. "Owwwwww!" she yelled.

"That's it, Santana!" Brittany giggled with excitement. "Fuck her ass and pinch her tits! It's a rave! An ass-fuck rave!" Brittany was in the middle of a gigantic orgasm and knew what she was saying even less than usual.

Santana grunted and continued to fuck Rachel, savoring the feel of her virgin asshole giving way before the monstrously large strap-on. The singer writhed in pain, still trying to escape the fire in her ass as the Cheerio's huge dildo tore her in two. She tried to relax—force herself to relax so it wouldn't hurt so much. She wanted to surrender to that awful strength propelling solid latex rubber inside her anus, but her body wouldn't answer to her.

Until, somehow, it did. Through the magic of Stanislavski's System, Rachel began to feel a little turned on. That feeling grew rapidly. In a few seconds, she was actually beginning to enjoy Santana taking her asshole!

She moaned and clenched her ass hard, gripping Santana's raging strap-on as it slid smoothly in and out of her hole. Santana was fucking her ass furiously now and Rachel began to instinctively thrust her asscheeks up to meet the thrusts of that mammoth strap-on.

"Look, Santana! It's just happening just like I said!" Brittany cried, another orgasm ripping through her. "She's starting to like it! Just like I liked getting Lord Tubbington!"

"Yes, yes, you were right for once, Santana!" Rachel shouted, her entire body flushed with desire and excitement. "I'm finding anal intercourse very enjoyable indeed!"

"See, Strawberry Dykequiri?" Santana laughed triumphantly. "I told you!"

"Shove it all up my ass, Santana! It's very wasteful, environmentally speaking, to manufacture that much rubber and not use all of it!" Rachel lectured, growing hornier by the second.

"About another inch to go." Santana grunted. "You're real tight, Girl Moustache. Big surprise there. Shoulda shoved a piece of coal in your poop chute during freshmen year, I would've had a diamond by now."

"You could've asked me to marry you!" Brittany cheered.

"Fuck your whole strap-on up inside me!" Rachel wailed, literally acting her ass off. "Don't worry about hurting me! I love it! Just fuck meeeee! I have to feel all of your big hard strap-on shoved up my little asshole!"

"Okay, Treasure Trail! You asked for it!" Santana cried.

Brittany paused in her finger-fucking and leaned forward, her eyes widening as she watched the action before her. She had to see it when Santana shoved her entire eight-inch dildo into Rachel's virgin asshole. She wanted to make sure Santana really put the entire thing in Rachel, and didn't hide it up her sleeve like a stupid magic trick.

Santana pulled her strap-on out of Rachel until only the tip remained inside. Then she plunged her strap-on forward again with all her cheerleader strength until the full eight inches of latex rubber were buried up Rachel's ass.

"AHHHHH! So big! So hard! Oh, God, it feels sooooo good! I love it! No wonder lesbianism is such a valid alternative lifestyle!" Rachel cried. Her body no longer resented the fierce intrusion. A second without it had felt like an eternity.

"Can you do that again?" Brittany asked, now thrusting one hand in and out of her cunt while her other hand held the camera up high. "I was thinking of something else."

"You got it, baby," Santana grunted as she pulled her strap-on almost all the way out of Rachel's asshole. Then, tearing back, she plunged her dildo quickly back in again.

Rachel hit a high note, her eyes rolling back in her head. Her cunt throbbed and flowed, bursting so wet it turned her panties white.

"What do you say now, Rachel? You want me to stop fucking you?" Santana asked with a knowing laugh.

"Nooooo! Oh, God, no, Santana! Please don't stop fucking me, whatever you do!" the girl cried, sobbing with pleasure.

"Don't worry, baby! I wouldn't have stopped even if you wanted me to. I can't! I can't stop fucking your little ass until I shoot my wad right into it!"

Rachel moaned with lust. She loved Santana's words. She wanted exactly what Santana wanted: a bigger bust and for Santana fill up her asshole with hot jism. She just wished Santana actually could. She blamed society's failings for the inability.

She tapped on the coffee table and Brittany, somehow able to remember the signal, brought the camera in close. Rachel looked right at the lens.

"I voted for George Bush," she said, then hung her head, holding the pose as she imagined the Fin caption being splayed across the haunting final image of their student film.

"That was a great performance, Rach. I really thought you didn't want me to take your backdoor cherry on camera," Santana said.

"Thanks, San." Rachel raised her head, looking at the camera. She could just imagine college admissions looking at her now, looking around at each other as if to say 'how can one eighteen-year-old actress be so brave when Jessica Alba won't even go topless?' "But I'm willing to do whatever it takes to support my director's creative vision, and to draw attention to the underreported issue of lesbian anal virginity loss. Brittany, did you know that seventy percent of teenagers that have anal sex with strap-ons report that they're dissatisfied or regretful of their first time being penetrated in the rectum? It's because of scenarios like the one we've just depicted that anal sex isn't fun for everyone."

"But what can I, an average or below-average teenager, do to help?" Brittany asked.

"That's a good question, Britt. But first, Santana, do you think you could remove your strap-on from my posterior?"

If Santana had balls, that was how deep her strap-on would be buried in Rachel's tight, clenching asshole. The tender walls of her asshole were stretched to the breaking point around Santana's hard strap-on, and though she quite enjoyed it, Rachel didn't think it was appropriate for a discussion of this magnitude.

Slowly, Santana eased her dildo almost all the way out of Rachel's asshole again. Then, pausing for just a few seconds as she hovered above the singer's trembling ass, she plunged her strap-on in deeply to the hilt, her muscular thighs slapping wetly against Rachel's asscheeks. Those well-rounded asscheeks jiggled like Jell-O, doing a little dance for Santana.

"Oh, fuck, that was good, Santana! That was really good!" Rachel moaned as she humped her ass back toward the Cheerio's plunging strap-on. "But we really should stop, now that we've shot your film. We wouldn't want Brittany to get jealous."

"I love watching Santana fuck other people," Brittany announced. "Quinn's another blonde, so when Santana fucked her, I pretended we were twins having a threesome. I was the evil one. I thought things."

"I want to do another take," Santana drawled in Rachel's ear. "Brittany, sit over there, let's get another angle."

"You're so right, Santana." Rachel struggled to speak as she was repeatedly hilted. Over and over, Santana rammed her asshole. In and out. In and out. Each time she buried her dildo its full eight inches up Rachel's small, tight asshole. "I am, of course, wholly devoted to this project and my professionalism is such that I would never dream of shying away from my duty as an actress."

Santana groaned with the sheer pleasure of taking a black cherry. She had never fought such a tight asshole before and it thrilled her beyond belief. Her face took on an expression of utter depravity and lust, like she had just watched a K-Stew interview, as she continued to thrust her strap-on into Rachel.

She could tell from the girl's moans and wiggles that she was enjoying her first ass-fuck every bit as much as Santana was enjoying giving it to her. Rachel was writhing and moaning in need and she had to know that her orgasm was only minutes away.

"Ohhhh yessss, Santana! Fuck me good! Fuck me hard! I love it so much! Ohhhhh, shove your big strap-on up my ass! All the way, all the way! This feels so much better, knowing your dildo is biodegradable!" she yelled in a frenzy of lust and social awareness.

"Quinn's gonna owe me a bouquet of flowers after this. She's gonna be able to fist your ass no problem for a week!" Santana yelled, hardly recognizing her own voice, it was so thick with lust.

Rachel gasped with joy as the Cheerio continued to plunge her strap-on in and out of her clinging tightness. She concentrated on constricting and loosening her limber muscles, giving Santana's strap-on a massage like it was a real dick.

Santana groaned with pleasure and lust. "You squeezing that dildo, baby? Squeeze it tiiiight!"

Rachel moaned and continued to clench and unclench her tight ass, feeling Santana's huge strap-on throbbing deep within her. It was like a living thing inside her; she could've sworn she heard it purring in contentment.

"Your ass is so fuckin' tight! I wish I could feel it, baby, I just wish I could feel it!" Santana panted. Sweat was pouring down her face and running onto Rachel's naked back as she continued to fuck her madly with all eight inches. "Brittany, are you just getting the close-up of her raising her ass to make it easier for me to penetrate her? Not anything but my dildo slamming into her little ass?"

Brittany nodded. Both Santana and Rachel heard the wet, squishing sounds and groans of pleasure coming from the chair where she sat, once again finger-fucking herself. The wet sounds of her masturbation mingled with the naked flesh slapping sounds of a virgin asshole being fucked, arousing all three of them more and more.

Zev95
Zev95
1,580 Followers
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