Legally Blonde: An Anal Parody – Celebrities & Fan Fiction

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SUMMARY: Elle teaches Vivian the joys of anal sex.

NOTE 1: This is dedicated to MTL17 who suggested this wicked back-to-my-college-days favourite movie.

NOTE 2: Thanks to Tex Beethoven for editing this story.

LEGALLY BLONDE: AN ANAL PARODY

Elle Woods was perceived by everyone who didn’t know better as a sweet, pretty blonde… and so she was constantly underestimated… seen as no more than a dumb blonde… as a chick with big tits… as a bimbo…

But in truth, Elle loved proving all those people wrong. So her recent victory in the courtroom was perceived by many of her former detractors as her redemption, but for Elle it wasn’t one. It was just another instance of her proving everyone wrong… a frequent practice she revelled in.

Just like she’d been doling for her entire life. From serving as the student body president of her school, to enrolling in Harvard Law College on a whim, to overcoming the judgemental and pretentious Harvard crowd, and of course winning that high account case.

Christ, she even ended up becoming friends… best friends… with her former rival Vivian.

Also, behind Elle’s sweet bubbly persona, was another side of her… well… sort of… she was all the time bubbly… even during sex… but she was also quite kinky… kinky in a way no one who hadn’t slept with her would ever Imagine.

Elle loved anal sex. Even more surprisingly… and more perversely… she loved fucking people in the ass. Both guys and girls.

She had a dozen different strap-ons… all but one of them designed for anal sex… most were for fucking women… all but two were pink… and she’d been pegging Warner for years back when they were dating, and she hoped to be pounding Emmett’s ass soon… his cute ass looking so ripe for the plundering.

At the end of the day of her big victory in court, Elle slapped Vivian’s ass triumphantly and crowed, “You see, Viv? I always win, and I always get what I want.”

Vivian was rattled, both by Elle’s words and the strange tingle in her pussy from getting slapped. Warner was shockingly tentative in bed, easily the worst lover she’d ever had, although she hadn’t been dating him for sex, but for power… the big rock on her ring finger a symbol not of love, but of social status.

She watched in disappointment as Warner went over to Elle after the win… even before they’d left the courtroom… and clearly tried to coax her back, and she then smiled in satisfaction as Elle crushed him in a heartbeat. (She wasn’t close enough to listen in on the exchange, but she didn’t need to… the visuals said it all!) It was then she knew she needed to break free from her parents’ expectations and cutthroat social climbing, and to become herself… instead of what everyone else told her she should be.

So Warner was rejected twice on that day, and was left to wonder what the hell he was supposed to do with a suddenly pointless $9,000 engagement ring.

Elle celebrated her victory by pegging Professor Callahan in his office and he, just like Warner all the time had, finished by spewing his load all over the carpet without his dick being touched. Because she was spiteful for his attempt to force her to have sex with him before she’d be allowed to get ahead… at least according to his claims… she made him eat his cum off the rug.

Over the next few months, Elle and Vivian became good friends… best friends… forming an intimate two-girls-only study group.

Elle, who was an anal junkie and who wore a strap-on and fucked numerous assholes for her go-to stress release, gradually collected a harem of submissive anal pets… both guys and gals… who were at her beck and call.

The same night she’d destroyed Professor Callahan’s ass in a ruthless drilling, she spent the rest of the evening at Brooke Taylor Windham’s upscale condo for a wild night of lesbian activity, including a 69, and Brooke had the best workout of her life with a marathon, multiple-orgasm anal reaming while Brooke’s maid ate Elle’s pussy the entire time.

Not surprisingly, or perhaps it was surprising, Elle was able to seduce and add Professor Stromwell to her stable of anal pets, really getting off by fucking her in her classroom after hours. The Professor was a lesbian and a nasty slut behind her prim and proper persona, and she loved sucking a cock that was just in her ass. The formidable Professor had her own large number of pets, including fellow professors, the wives of some other professors, former students, practicing lawyers, a couple of politicians and more… many of whom willingly became anal sluts for Elle too, because their Mistress, Professor Stromwell, ordered them to. The Professor was a dominant woman, a seductress, but while she was all the time in control of her pets… she mindlessly explored her never-before-tapped submissive side with Elle.

Elle also had her eye on Vivian… but she didn’t want to damage their friendship, so she had to take things slowly.

So as the year progressed, she took lots of sly, subtle steps to start her seduction.

She began kissing her on the cheek whenever they encountered each other.

She described her as her girlfriend not only when they were alone together, but also to other people.

Elle used Vivian’s assistance in the majority of her research since Vivian was excellent at it, but then joked Vivian was her bitch.

At first Vivian wondered Elle was just being silly… yet she kept doing it more and more often.

Unlike Joey, Vivian’s previous boyfriend before Warner, who’d called her names and treated her like a cheap slut, which she hated that she loved, when Elle called her names she all the time did it using her happy voice and tone… so it was hard to take her jibes seriously.

On occasion, when Elle gave her a certain look that wasn’t one of her usual ones, which seemed to reveal just a hint of darkness behind her carefree persona, she thought if Elle had another side of her: a sinister one lurking behind that façade of perpetual happiness…. Part of Vivian hoped so; nobody should be that perfect.

Vivian too wanted to change her image: in her case to be seen as more than just a bitchy Prima Donna, which in fact she’d been successfully changing ever since becoming besties (Elle’s word) with Elle, who was her polar opposite. While everyone had all the time seen Elle as a sex object and most of them still did, Vivian had been viewed as a nerd… even though she had great firm tits and an amazing ass. She also missed the rough fucking Joey used to give her. Face fuckings, facials, handcuffs, and verbal humiliation… as Joey was the only one so far who’d seen through her entitled diva act to detect her natural submissiveness… which she was now naturally beginning to manifest more and more over time for Elle. Doing research for her, fetching her fruit drinks, and she’d even massaged her feet last week for the first time, whereupon she discovered her best friend wore very expensive hosiery, and Elle parted her legs to reveal she was wearing a garter-belt and stockings… the softest hosiery Vivian had ever felt. Adding to her surprise, when she looked up, she saw very clearly that Elle wasn’t wearing any panties, and her pussy was completely shaved.

So now, in addition to Vivian becoming more and more submissive to Elle in nonsexual methods, seeing her friend’s pussy was bringing out another side of her. In the past she’d had a couple of lesbian encounters, on the whole preferring them to men, since it was only on that side of the street she’d ever come from interpersonal sex, and suddenly the idea of getting sexy with Elle wouldn’t leave her head… even though Elle was now dating Emmett… who she had completely wrapped around her finger… just like she had everybody else.

All of which led to Elle inadvertently springing a specific trigger term after all these months of her carefully plotted psychological buildup. Elle slapped Vivian’s ass particularly hard after Vivian had brought her some files. (By this point Elle had been given her own office at the law firm, even though she was only doing pro bono work for them.) And as she slapped that ass she said, “Thanks, bottom bitch.”

Hearing that term sparked an incident from Vivian’s past… since it was the same term that had quickly led to the end of her relationship with Joey. She’d refused to give up her ass to him when he’d declared it was time to mark her as his three-hole bottom bitch. When she’d told him adamantly she was absolutely not into anal, he tried to force the problem, and she’d ended up kicking him in the nuts to fight him off. Whereupon he became hysterical, called her every name in the world, and dumped her on the spot.

Ordinarily she was proud of standing up for herself, but on occasion guilt hit her for not being eager just to give it up for her man so she could keep him. Especially since she hadn’t been fucked by anyone except Warner ever since, who as has been said, was a terrible lay.

Elle noticed Vivian’s face flush ruby red upon being called a bottom bitch… which made her curious as to why her bestie suddenly looked uncomfortable.

“What? You don’t want to be my bottom bitch, girlfriend?” Ella asked.

“It’s just that….” Vivian began and stopped.

“What? You can tell me anything, girlfriend,” Ella said, squeezing her friend’s shapely big booty… which was undoubtedly perfect for some back door hammering, once the time was right.

“It’s just that… you remember Joey?” she asked.

Elle had never met Joey, but she recalled Vivian mentioning he was her boyfriend before the sexual doldrums of Warner, Vivian never having learned he was a sissy bottom bitch who preferred being fucked to fucking… but knew from Vivian revealing a few too many details when tipsy about Joey being quite a stud, which had helped to confirm Elle’s suspicions about Vivian being submissive. “Oh yeah, that stud boy from your past.”

“Yeah, well… I never told you the reason we broke up,” Vivian confessed, having never told anyone. He was a bad boy without much money… who she’d never introduced to her parents… so Elle had assumed he was just a fling.

“It wasn’t because your Mommy and Daddy saw those pictures you showed me and didn’t like him?” Elle asked, having assumed that was the reason. Joey had numerous prominent tattoos and worked as a mechanic, not the sort of guy who’d be welcomed into the hoity toity world of the overly privileged.

“No,” she said, having all the time resented people assuming that, even though it would have become a issue eventually, and the break-up had eliminated that upcoming hurdle.

“Then what was it, you silly goose?” Elle said, slapping her ass again.

“He dumped me because I wouldn’t let him fuck me in the ass,” Vivian blurted out.

“Oh, I see,” Elle said, remaining behind Vivian, and this time she used both hands to caress the perfect and, she now assumed, virgin booty.

“What are you doing?” Vivian asked, even though she didn’t move away from this gentle yet firm caressing of her ass cheeks.

“You didn’t allow that hot guy to fuck this amazing ass of yours?” Elle asked, ignoring the question.

“No,” Vivian shook her head while her best friend squeezed her ass and made her upper cheeks flush. “It’s dirty.”

“Not when it’s done right,” Elle contradicted, her breath hot in her friend’s ear.

You’ve done anal?” Vivian asked, astonished.

“Oh yes, I do anal a lot,” Elle said, stressing the word. “There’s nothing more thrilling than a good, hard ass fucking!”

“Elle!” Vivian gasped, as she felt her friend’s hand reach under her skirt and touch her directly between her pantyhose-clad ass cheeks.

“What, bottom bitch?” asked, poking a finger against the puckered virgin hole through the pantyhose.

“I’m not a bottom bitch.” Vivian denied angrily, as she felt Elle ripping a hole through her pantyhose.

“Given the uneducated attitude you’ve just expressed, you certainly aren’t. Not yet, anyway,” Elle said, enlarging the hole wide enough for easy access.

“What are you doing?” Vivian asked again, when Elle spun her around and bent her over her desk.

“Making you an actual bottom bitch,” Elle said as she slapped the big booty, “My bottom bitch.”

“Elle, this isn’t funny,” Vivian objected, even though she could feel wetness leaking into her panties from the firm spanks. She’d enjoyed it when Joey had spanked her, and also loved Elle’s increasingly evident dominant side… so she didn’t try to withstand or to stand back up, but remained accommodatingly bent over.

“You’re right; your being an anal virgin is no laughing matter,” Elle agreed, deliberately missing the point, and she reached for some scissors lying on her desk and warned, “now don’t move for a moment.”

“What are you doing?” Vivian asked for a third time, looking back to spy Elle brandishing the scissors.

“Getting rid of this inconvenient underwear,” Elle said, as she snipped the thong into three fragments and tossed them away haphazardly.

“That was expensive,” Vivian gasped… the most expensive thong she owned.

As Vivian was still bent over, Elle spanked her ass again, saying, “My pets don’t wear underwear, and they never wear pantyhose.”

“Pets?” Vivian asked, her ass burning a bit as was, inexplicably, her pussy. A pussy that hadn’t gotten any action since Elle had won that trendy case six months ago. Certainly it had hosted some toys… but not any living dick… or not even any willing first-year pussy lickers… it had been enduring quite a dry spell.

“Yes, I call people who service me and obey my every whim my pets,” Elle said in her trademark casual cheery matter-of-fact fashion, as she pried the big booty ass cheeks wide aside to take a good look at the rosebud she was about to deflower, and then to destroy… the latter action all the time following the former.

“You have a few girls who service you regularly?” Vivian asked, each new revelation shocking her more than the previous as she felt Elle’s hands on her ass cheeks pulling them aside. “And you mean sexually?”

“Yes, and quite a few of them by now, plus a few guys,” Elle said, as she leaned closer to get an up close and personal look at the puckered virgin asshole. “As you’re about to begin learning first hand, I have a very active sex drive.”

“You do?” Vivian asked, feeling her bestie’s hot breath between her ass cheeks… this entire episode feeling totally surreal.

“I know…” Elle said, well accustomed to witnessing the shock of a new pet while she processed the outwardly sweet, innocent, bimbo-like Elle revealing herself as quite the seductress while she transformed them into lesbian pussy-licking, ass-taking sluts. “…everyone thinks I’m this sweet, almost virginal, prim and proper gal… but….”

“But whaaaaaat?” Vivian moaned in astonishment, as she suddenly felt a stiffened tongue probing against her butthole.

“…butt… for example, I love eating sweaty assholes just like yours,” Elle revealed, as she swirled her tongue around in the salty sweat of the pretty, puckered, inviting hole.

“Ohhhh my,” Vivian moaned, as she remained bent over and allowed Elle to lick her asshole. She was stunned this was happening… and equally stunned by how good it felt to feel this tongue bathing her butthole.

“Such a delicious ass you have, my dear,” Elle purred, sounding vaguely like Red Riding Hood’s wolf, as she licked and probed.

“I can’t believe you’re doing this to me,” Vivian said, almost whining, but not quite.

“Oh, this stage is only the means to an end. I’ve got to get this asshole nice and ready for my strap-on,” Elle explained, all the time keeping a couple of them in her desk, and at least one in her carry bag for emergencies… and Elle encountered a lot of such emergencies.

“For your whaaaaaat!” Vivian cried out, her eyes going wide.

“Oh my sexy newest bottom bitch, your asshole was just made to be fucked,” Elle crooned, and she stood up and ordered in a firm voice, “So don’t move a muscle, my sexy slut.”

Vivian was overwhelmed. She mindlessly obeyed, remaining vulnerably bent over while she watched Elle step around to the opposite side of her desk, pull out a bottle from a top drawer and return. Elle had just warned her about exactly what she was about to do. Which in the past she’d all the time considered a non-negotiable dealbreaker. So why was she allowing this scene to continue? And why was she so turned on?

“You see, Vivian,” Elle explained, as she returned to the company end of her soon-to-be bottom (the person, not the body part, although that too), “Men aren’t equipped to understand the complexities of a woman’s body. They don’t understand our tits, they sure as fuck don’t understand our pussies, and they haven’t a clue about our assholes. To them, tits are for fucking, pussies are for fucking and assholes are for fucking… all of which can be true, but only after the woman’s body and her mood have been properly addressed.”

“I don’t believe my asshole was remotely made for fucking,” Vivian argued, even though the tongue licking had been very nice, relaxing, and subtly erotic.

“Oh, trust me my pet, as I’m about to demonstrate, your asshole was definitely made to be fucked, pounded, and even destroyed,” Elle said, and the way she asserted this foreign concept so casually and in her ubiquitously cheerful voice made it sound both nasty and logical.

“I don’t know,” Vivian said, as she felt some warm, oily liquid being trickled between her ass cheeks.

“Ah, but I do know,” Elle said. “I know exactly what you need.”

“And exactly what do I need, Mommy?” Vivian asked sarcastically, getting rather annoyed again. She’d all the time hated when people tried to dictate what she wanted or needed. Past boyfriends, her parents, teachers or professors. She was the only one with an inside scoop to her inner self!

“Don’t give me that tone,” Elle said. “I’m not telling you in a condescending or parentally biased way, I’m telling you as another woman, as your best friend, and as your experienced and knowledgeable Mistress.”

“Mistress?” Vivian asked.

“Yes,” Elle said, as she pressed her lube-coated index finger against Vivian’s delicious asshole, “you’re now my pet, and I’m your Mistress.”

Maybe I’ll be willing to be your pet. But what does a pet doooooooo?” Vivian asked, feeling curious, turned on and confused by all her conflicting feelings and inclinations, which included an abiding trust and affection for this irrepressible blonde, which were complicated greatly when she felt that finger slide smoothly into her ass.

“Simple. You obey your Mistress unconditionally,” Elle explained succinctly, as her entire finger disappeared inside her bestie’s tight asshole.

“Ooooh,” Vivian moaned, becoming aware of a very subtle pain inside her ass, and yet also a strange and unfamiliar wave of pleasure cascading through her body that mostly numbed the pain.

“And you’ve pretty much been obeying me unconditionally for a while anyway,” Elle added, as she wiggled her finger around inside her friend’s ass to initiate the gaping process.

“Oooooooh,” Vivian moaned involuntarily, feeling Elle’s finger exploring her ass in a way that felt strange, and yet oddly pleasant… to the extent that it distracted her from denying the idea that she all the time obeyed Elle… which, once she wondered about it, was sadly true. Or perhaps not so sadly, for behind her heretofore stuffy, bitchy persona was a woman born and raised to be an good and obedient daughter who did exactly what she was told… especially by her mother… and who’d followed her family’s expectations without any outward resistance… although as has been said, occasionally with some inner resentment… and the process had occurred so naturally and perpetually that without her even knowing it, she’d been trained to become a perfect submissive… or at least one to the right person of the feminine persuasion… such as Elle.

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