Anna Kendrick’s Wilde Night

Title: Anna Kendrick’s Wilde Night

Author: TheBigLove126

Celebs: Olivia Wilde, Anna Kendrick

Codes: FF, celeb, cons, toys, bond, oral, drunk

Summary: Anna Kendrick goes over Olivia Wilde’s house

Disclaimer: The following story is fictional. I am not in any way saying that Olivia Wilde and/or Anna Kendrick are into these kinds of things, but they would be the greatest women in the world if they were.

If you have any questions, comments, story requests or other feedback to this or any of my other stories; feel free to contact me at – or chat with me on YIM, I am almost always online.

“Hey Anna, I’ve got a bottle of vodka and Jason is out filming a movie. Wanna hang together?” the text from Olivia Wilde read.

“Sure, I’m not doing anything. Be right over!” Anna Kendrick responded.

After filming their movie “Drinking Buddies”, the two actresses became very close friends. After Anna broke up with her longtime boyfriend, Olivia was the first person she called and ended up living with her for about a week. It had been a month since she had moved back to her own house when Olivia texted her for a fun night. It was the first time, other than the movie’s premier, that Anna had left her house and she was ready for a fun night.

The short brunette changed out the pajamas that she had seemingly been wearing for weeks and into a comfortable pair of jeans and a loose black t-shirt with a picture of a giant purple cat on it before getting into her car and heading to her friend’s house.

Once she arrived, she knocked on the door and was quickly greeted by her friend. Olivia was holding the bottle of vodka, which she had clearly taken a few sips of. She was wearing a long white dress shirt that went past her hips and a pair of short blue shorts that were not visible under the shirt. The taller woman held Anna’s head between her hands and gave her a kiss on the forehead, something that she had done while consoling over her breakup. The kiss caused both girls to giggle before Anna walked in.

“Cute shirt, never seen you in it before,” Olivia said as she poured a glass of vodka on the rocks for her friend.

“I did some radio interview in Richmond and they were handing out free shirts, I thought this one was cute,” Anna said as she swallowed down half the glass of vodka in one sip.

“Someone wants to get drunk,” Olivia said with a smile.

“Edgar dropped off the last of my stuff this morning and seeing his face again…” she pounded down the rest of the drink. “I need this badly.”

She grabbed the bottle out of Olivia’s hand and filled the glass again, drinking yet another large amount.

“Pace yourself sweetie, I don’t want you dying on me,” Olivia said pulling the bottle away. Anna whimpered when she lost control of it and gave her friend a sad-little-girl look. Olivia kissed her forehead again.

Anna continued drinking (at a slightly slower pace) while Olivia slowly nursed her own drink. By nine o’clock, three hours after arriving, the younger girl was starting to get incoherent; she was so drunk while the older girl felt a nice, calming buzz.

“How are you feeling sweetie?” Olivia asked.

“I’m…I’m feeling AWESOME!” she yelled before breaking out in a laughing fit.

Olivia laughed at her before taking her glass away. “I’m going to cut you off right there.”

“I’m…I’m fine,” she said with a serious look before starting to laugh again.

Anna fell to her knees on the carpet and almost hit her head on the coffee table. Olivia picked her up and sat her back on the couch. The drunken girl looked her right in the eyes and wrapped her arms around her friend. She rested her head against Olivia’s chest and started mumbling to herself before passing out.

Olivia smiled and gave her friend a hug and a forehead kiss before picking her up and carrying her to her bed. She gently lay Anna on top of her bed and stroked her cheek, bringing a small smile to the passed out girl’s face.

“So sweet…so pretty…so innocent,” Olivia said to herself. “One of those needs to change.”

She walked over to the bedroom door and locked it before returning to bedside. She bent down and gave a kiss to Anna’s cheek while she ran her hand across her chest, down her stomach and to the zipper of her jeans.

“Tonight’s gonna be fun!” she exclaimed as he grasped the zipped and slowly pulled it down.

Olivia took her time slowly pulling the tight jeans down Anna’s slender legs, keeping her eyes locked on the pair of pink panties in front of her. She bent down and kissed her on the hip as the jeans finally reached Anna’s ankles. Once she fully removed them, she looked back at her chest.

“That is a really cute shirt, wouldn’t want to get it all wet and messy,” she said as she slowly lifted the shirt off and threw it across the room.

Anna, passed out drunk, was left only in her matching black bra and panties while Olivia stood over her with her mouth (and other parts of her body) beginning to moisten. She grabbed on to her bra by one strap and lowered it down her arm before doing the same to the opposite side.

“I’ve always wondered…pink or brown?” she whispered to herself as she pulled the bra off of her breasts, exposing the perky twins. “Pink! I knew it…small, cute and pink,” she said as the tiny pink buds were met by the cool air of the room, hardening instantly.

Olivia took a few minutes to softly massage her unconscious friend’s breasts, occasionally stopping to lightly tug on her nipples. She could feel her own pussy beginning to get very warm and very wet, which got her wondering how Anna’s was reacting. She giggled before slipping two fingers under the waist and of the black panties and lowering them. She was met by a nicely trimmed bush above a very red, very wet pussy. The smell of her friend’s essence only drove Olivia even wilder.

Before Olivia could continue, she reached under her bed and pulled out a small tackle box. She opened it up and pulled out four foot-long ropes and started tying them to the four bedposts.

“I don’t know if you will like this or not when you wake up…I’m not letting you run off my sexy little bitch,” she whispered to the sleeping girl before tying the other ends of the rope to Anna’s hands and feet.

Anna was bound tightly, her nude body fully suspended in the air just two or three inches from the sheets below. She had still not made a sound or movement throughout the whole experience.

Olivia stood over her friend/toy and giggled before pulling her shirt up over her head, exposing her own breasts as she was one to rarely, if ever, wear a bra. She yanked her shorts down and, again with no underwear, was fully nude. She placed her hands on Anna’s stomach and crawled onto the bed. She planted her ass down above her pussy and slowly bent forward until her lips were just inches away from Anna’s.

“Your forehead is nice but I want to taste that cute little mouth of yours sweetie,” she said before pressing her lips onto Anna’s, slipping her tongue between them.

Olivia’s tongue wrestled with Anna’s for several seconds before the first sign of life showed and she started kissing back. She was still passed out but her tongue was too happy to stay still. Olivia caressed her cheek as they twirled each other’s tongues around. After a few minutes, the kiss was broken and Olivia sat up. A small smile came to Anna’s face as Olivia started lightly pinching at her own nipples.

Olivia reached behind her and pressed her hand against Anna’s red hot pussy. She could feel the heat being created before her hand got anywhere close. Once her fingers made contact, they easily slid right in. Anna easily took two fingers between her lips and started squirming around as soon as contact was made. Olivia looked at her face and smiled as her smiles turned sexy. In her drunken state, she was instantly and unknowingly enjoying the contact.

Slowly, Olivia slid off of her friend and stood next to the bed, her finger never leaving the pussy. She started moving them in and out, causing Anna’s juices to drip down her ass and down onto the sheets. She reached into the tackle box and pulled out a large red, rubber dildo and let out an evil laugh. She looked over at Anna’s face again and noticed that she was starting to come to. She pulled her fingers out and walked next to her head, slowly stroking the dildo in Anna’s juices.

Anna slowly started to regain consciousness and opened her eyes. She was instantly concerned when she tried to move but, could not. Once her eyes were fully opened, she stared up at Olivia, naked and stroking a dildo that was at least a foot long.

“What the…what’s going on?” she slurringly said.

“Shh…” Olivia said, placing her wet finger on the girl’s lips. “You know what my finger tastes like?”

Anna slowly drew her tongue out and made contact with the finger. Her eyes quickly went wide and she tried to move again.

“Is that yours?” she asked, assuming it was Olivia’s since she was unaware that she herself was naked.

“Look down,” Olivia whispered.

Anna looked down and saw her body completely uncovered with her legs tied to the posts. She looked over her head and saw her hands bound.

“Why are you…,” she was again cut off by Olivia, who stuck both wet fingers into her mouth.

Anna had no choice but the taste her own juices again. She stared up at Olivia and started slowly sucking the womanly essence from the fingers in her mouth. After a few seconds, she closed her eyes and started sucking harder. In her drunken state, she was enjoying this probably more than she typically would.

“That’s a good girl,” Olivia said before kissing her on the forehead. Anna looked up at her and smiled. “I think someone likes this. Are you?”

Olivia pulled her fingers out of Anna’s mouth to allow a response. “I…I taste my pussy after I play with myself all the time…I love it.”

The two girls smiled before Olivia bent down and shoved her tongue into Anna’s mouth again. This time, she was met with instant response as Anna tried to take control of the kiss. They made out for several minutes before finally breaking the kiss.

“Why did you tie me up?” Anna asked.

“I didn’t know if you’d be into this and I wasn’t letting you get away. I’ve waited a long time to fuck you…that’s why I let you do most of the drinking,” she responded, holding the rubber dildo against her chest. “Still drunk?”

“Very,” she said giggling.

“Sweet. Bet you’ve never had a girl fuck you with a dildo before,” she said laughing.

“I’ve never done it with a girl…or with one of those,” she responded.

“You’ve never used a dildo?” Olivia asked, shocked.

“Nope. I’ve only had a real cock or my hand in there,” she said, staring at the toy.

“Twenty-seven years old and never played with a rubber cock…bad girl,” Olivia said before lightly slapping Anna across the face with the toy.

Anna was shocked at first but felt some of the juices on the toy roll into her mouth. The second her juices were in her mouth again, she smiled.

“I guess I am a bad girl,” she said.

“A very bad girl,” Olivia said, again slapping her with the toy, this time on the chest. “Bad!” she said slapping her stomach. “Bad!” slapping her hip. “Really. Fucking. Bad!” she yelled as she slapped her pussy hard, causing Anna to squeal. “Ever had a cock this big inside you?”

“The biggest was eight inches,” Anna responded.

“Add five and that’s what you’re about the get,” she said. Anna was too drunk to properly do math, so she gave a confused look to her friend. “Thirteen sweetheart, this thing is thirteen inches long.”

“I don’t think I can take thirteen,” Anna said, with a nervous look.

“I guess we will find out, won’t we?”

Olivia crawled on the bed, facing away from Anna. She sat down on her stomach and held the toy against her hot opening.

“You have a nice ass,” Anna said.

“Thank you, I’ll let you get a closer look in a few minutes,” she said smiling, looking over her shoulder. “But first…get ready honey.”

Anna bit down on her lower lip and her eyes shot open as the wide head of the toy stretched her vaginal walls like nothing before. She let out a hard moan the rocked her whole body. Olivia laughed as she was almost bucked off the smaller girl. She slid the toy in farther and farther, taking eight inches almost with ease. She pressed a finger against the girl’s clit, hoping to make her wetter with more contact.

Anna had a look of pure ecstasy on her face as her pussy got slicker and slicker. Olivia put some pressure on the toy and continued to insert it. Anna cried as the ninth, tenth and eleventh inch of the toy enters her. Between the tears rolling down her cheek dragging eye-liner with it and the sweat beading over her entire face, she was a soppy mess.

Olivia looked back and gave a devilish smile before pushing the dildo in for the twelfth inch to clear her entrance. The moans from Anna were getting higher pitched and closer together while her pussy was getting hotter. Olivia spit at her pussy, determined to fit the thirteenth and final inch of the rubber dildo past her pussy lips.

“Ready?” Olivia asked.

Anna was too lost in her own lust to even hear the question. Olivia took this as a yes and forced the last inch of the toy deep into her stretched pussy. Anna exploded in a massive orgasm that forced the toy about half way out of her. She shot her head back and bucked wildly, almost knocking Olivia off of her.

“Anna, that looked like a monster orgasm,” Olivia said, laughing.

“Yeah…oh my fucking god…that was awesome,” she said, panting and sweating heavily from the mass jolt of pleasure almost caused her to pass out.

“Let me help you out,” she said before sliding her ass up Anna’s body until her ass was pressing against her face.

Olivia lifted herself up so that her pussy was within an inch of Anna’s mouth. Before Anna could make contact with her friend, she felt Olivia’s warm tongue slide between her pussy lips. She gasped before sticking her own tongue out and making contact with her clit. Olivia squealed at the touch and lowered herself down about, burying the drunken woman’s face deep into her pussy.

Anna’s nose was pressed firmly against the wispy trimmed pubic hair that sat above Olivia’s red hot pussy. Her tongue was shoved as far up it as humanly possible. Olivia’s tongue was doing the same to her pussy. The two women were completely lost in each other, having the times of their lives.

The girls remained locked in a suspended 69 for several minutes before Olivia started to feel her own orgasm creeping up. She slowly lifted herself up enough to give Anna some room. She reached behind her and untied the younger girl’s arms from the bedpost. Now with her hands free, Anna grasped onto Olivia’s round ass cheeks and pulled her tongue off her pussy. She reached forward and flicked at her clit as hard as she could.

Olivia turned around and placed her hands against the wall. She pushed herself forward and lifted her body up off of Anna’s face. She let out a long moan as she sprayed her womanly juices all over the drunken girl’s already-wet face. Anna closed her eyes and held her mouth open, allowing every drop that sprayed out of Olivia to end up in her throat.

Once Olivia had come down from her sexual high, she slowly lowered herself onto the bed and tossed an arm around Anna, who quickly sat up and untied her legs from the bed before rejoining her friend for a close embrace.

“That was amazing,” Anna whispered.

“Yeah it was,” Olivia said before kissing her neck. “Sorry about getting you pass-out drunk first but I wasn’t sure how you would feel. I’ve wanted to taste your pussy since the first time we met.”

“Don’t worry, I’m not mad. Next time, just ask and I’ll be over as fast as possible. I never thought sex with another girl would be so fun.”

The girls shared another long kiss before Olivia kissed Anna’s forehead one last time and rested her head on the girl’s soft chest. They both fell asleep with smiles on their faces.

To be continued if people ask for a second chapter…

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