Darkest Desires Vol. 01

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Olivia Wilde tries anal.
1.4k words
4.42
5.8k
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Darkest Desires Inc.

That was what the card said, the gilded font shining in the midday sun.

Olivia Wilde picked it up, studying it with narrowed eyes, her thin lips pursed. Turning it over, she found a phone number on the back, underneath it a single sentence:

WE MAKE YOUR FANTASIES REAL.

"More junk mail..." she muttered to herself, throwing the card on the side as she headed for the shower.

Attending the set, she made her way through hours of tedious reshoots, the only bright spark the flirtatious advances of her co-star Natalie.

Returning to her flat, she settled in with a glass of wine as she watched Peaky Blinders. As the wine poured down her neck, her thoughts drifted to the card on her side table.

"Oh, what the hell... it's probably a scam." She muttered as she crossed to the table and picked it up.

Phoning the number, it rang twice before a deep, masculine voice answered.

"Darkest Desires Incorporated. We make your wildest fantasies a reality."

Summoning her courage, Olivia smiled a little.

"Hi... I'm Olivia. What kind of services do you offer?"

"Well, miss, we offer discreet services to select clients, enabling them to fulfil their innermost desires in a safe, private manner."

"Innermost desires?"

"Yes, ma'am. Simply leave your name, the desire you wish to experience and your location. We will handle the rest."

Pausing, Olivia looked over at the near empty bottle of wine, a slow burn in her pussy as she bit her lip.

"Okay. My name is Olivia Wilde, I'm on Baltimore Wharf, and I would like to experience..."

Her last words following this were barely a whisper.

"I'm sorry ma'am. I did not catch what you wish to experience."

"I wish to experience anal for the first time." She mumbled.

"Yes ma'am. We have an employee half an hour away. They will be with you in an hour, and we hope you enjoy your darkest desire."

The man hung up.

Olivia returned to her sofa, draining her glass of wine. Her body was on edge, her foot tapping nervously.

A shower and two glasses of wine later, and there was a knock at the door. Tightening her robe around her, Olivia answered the door.

On the doorstep, dressed in a blue dress so tight it clung to her curves as if she had been poured into it. Full, pouty lips gave her a beaming smile, and shining blue eyes sparkled with warm arousal under a blonde bob.

"Miss Wilde, I'm Liana. I'm from Darkest Desires, and I will be your guide this evening."

"Guide?" Olivia asked as she invited the stunning woman inside.

"We are called guides, as it is our job to guide you through experiencing the most pleasure possible during our time together."

"Oh... umm, how do you intend to fuck my ass...? You're a woman..."

"We will get to that. Tell me, why do you wish to try anal? Have none of your past partners tried it?"

As she spoke, Liana demurely sat on the sofa.

"No... they wanted my pussy, just to say they had filled me with cum. No one was interested in it."

"I doubt that. Your ass is one of the most exquisite things I've ever seen. I cannot wait to fuck it for you..."

Turning bright red, Olivia shifted, the matter of fact tone of the woman making her hornier by the second.

"Umm... I've never been with a woman..."

"Well, trust me, Olivia... I'm going to slide my fingers into your ass... slowly, softly... I'm going to savor the sensation of your ass clinging to my fingertips as I open it up, preparing for my dildo. I'm going to taste you, my tongue slowly fucking that tightest of holes as I make you beg for me. Then I'm going to ease the dildo in, your beautiful body under mine as I stretch this exquisite ass and watch you quiver, hear you moan, and finally savor that soft groan of surrender as you feel my cock deep inside and realize another woman is owning you."

With every word, Liana leaned closer and closer, until she pressed her lips softly to Olivia's.

Moaning a little, Olivia returned the kiss, letting Liana lean her back against the sofa, the woman's fingers trailing up her thigh until she slid a finger into Olivia's dripping pussy.

"Oh, fuck, Liana..." Olivia groaned, opening her legs wider. "Please..."

Liana slowly fingered her, slipping the robe open to suck gently on Olivia's stiff nipples.

Olivia couldn't believe it. The pleasure Liana was bringing her was beyond what she had expected from the blonde, her experience with lesbian activity evident.

Easing the finger out of Olivia, Liana held it up to her.

"Suck."

Olivia instantly and greedily tasted her own pussy off the slim finger, moaning in delight at the crude act.

"That's it, Olivia... make it dripping wet..."

Olivia did as asked as Liana moved down and began to fuck her pussy with her wet, warm tongue.

Her hips writhed as Liana ate her, moaning long and loud in pleasure. The finger slipped from her mouth as Olivia cried out, her orgasm coating the woman's face.

Liana smiled, and - after meeting Olivia's hungry, wanting gaze - she slid her finger up to the first knuckle into Olivia's virginal ass.

"Holy..." Olivia groaned, "it feels bigger than it should..."

"Hush, baby... just let me work..."

Olivia nodded, letting herself be owned as Liana eased the finger in and out as she focused her oral attentions on the small bud of nerves at the top of her pussy.

Orgasm after orgasm lit up her body, her hands on Liana's hair, her body shaking and quivering as she realised she was a sexual puppet under the skilled direction of this beautiful woman.

As she came, over and over, the finger in her ass went deeper and deeper, slowly opening her, stretching her, invading her.

"Liana... my ass... please..."

"Beg, Miss Wilde..."

"I need to feel you in my ass... I need to feel you fuck me... please... I want you to take my ass..."

Liana smiled, sliding a finger free and replacing it with Olivia's own.

"Keep yourself open... I'll be right back..."

Liana left the room, heading for Olivia's bedroom. Doing as bidden, Olivia used two fingers to keep her anal passage open.

Liana returned a moment later, and Olivia gasped. The woman was naked, completely smooth and perfect. Around her waist, though, was a long, thick, intimidating strap on dildo.

She slowly turned Olivia over on the sofa, gently tugging her fingers out before she placed the tip of the dildo at her ass.

With a small shove, she popped the tip into the gaped hole, making Olivia cry out in pained pleasure

"Oh, FUCK!!"

Liana leaned down, stroking Olivia's hair as she kissed her cheek.

"Hush, baby... I've got it... I've got you... its mine. Let me fill you... I'll be gentle, and slow... let me own this beautiful ass.

Olivia whimpered, but gave a small nod, gripping Liana's hands as she prepared for the invasion of her deepest recesses.

Liana eased in, inch by inch of the stiff, unyielding rubber opening and possessing the tight tunnel.

Olivia felt Liana's hips press against her ass, and realized her favourite toy - a twelve inch long, three inch thick dildo - was completely inside her ass.

"That's it... I'm all the way in... how does it feel...?"

"It feels... odd... like you're not supposed to be in there. But at the same time, I feel like you were designed to take it... that you are meant to be in my ass..."

"I am, honey. I was meant to fuck your ass, and I'm going to..."

She fondled Olivia's pert buttocks, Olivia herself gripping the sofa.

"Please.. my ass is yours... fuck me..."

Liana began to move, the rubber shaft slipping almost out, before it slid all the way back in.

Over and over, Liana plundered Olivia's ass, gaining speed and force until she was pounding Olivia's rectum with brutal strokes.

"OH FUCK! OH FUCK! OH FUCK! OH FUUCCKKK!!!" Olivia screamed as her ass was utterly and thoroughly owned by the talented blonde.

Involuntarily, Olivia came.

A gout of pussy juice erupted all over the leather, her pussy aching as she orgasmed over and over.

Liana gripped her hair and pulled her tight against her, fucking her hard as she kissed Olivia.

After minutes became an hour, and an hour became two, Olivia meekly tapped her hand.

"Please.... No more... I can't take it..."

Liana immediately stopped, slowly moving to spoon Olivia on the sofa, pulling a blanket over them.

"So... how was your darkest desire, Miss Wilde...?"

"I have... no words... no, wait... I do..."

"Oh?"

"Be my girlfriend?" Olivia chuckled.

With a wry smile and a deep laugh, Liana whispered in her ear.

"I'd be delighted..."

Olivia smiled and gently kissed Liana, snuggling into her embrace.

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2 Comments
AnonymousAnonymousover 2 years ago

A finger and then a three inch wide dildo next? In an allegedly virgin ass? There a few pages missing in between.

AnonymousAnonymousover 2 years ago

A woman with a strapon? Really lame! Should have be two or three black guys fucking the shit out of her ass.

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