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Dating Anna Kendrick	By : TheChemist Category: Celebrities - Misc > General Views: 9370 -:- Recommendations : 0 -:- Currently Reading : 2
Disclaimer: This is an act of fiction. I do not know Anna Kendrick, Alison Brie, Cara Delevingne, Taylor Swift or Kristen Stewart. I make no money from this story.

Chapter List
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Summary: Continuation of Anna Kendrick Super Bowl Bet and Alison Brie’s repayment. Og is in LA and calls up Anna who’s happy to have him but also has a girlfriend in town, Kristen Stewart.

“We have now landed in Los Angeles, thank you for choosing…”
I didn’t normally sleep on flights and this one was no exception. It wasn’t a long journey as Vancouver and LA weren’t too far apart. I was able to get caught up on a few TV shows that I was meaning to so that my friends would stop potentially spoiling future events.
As soon as I was back on solid ground I powered back up my cell. I had a few messages but those would wait for now as I only had thoughts for one particular person. I scrolled through my contacts until my thumb fell onto her name, Anna Kendrick.
Anna and I had been friends with benefits since the Super Bowl last year. We had met while I was working on set at one of her movies years before and we had always stayed in contact. When she text me and said she was alone in Vancouver filming while her team was in the biggest football game of the season I invited her to the party I was throwing.
That went well by the fact that we had sex that night several times and continued our tryst throughout her time in Canada. When she left we stayed in contact every now and then but now I was being sent to complete a certification that was being held in California, specifically in the city Anna lived.
“Anna…it’s me Og,” I said after hearing her pick up her phone.
“Hey stud! Your plane arrive alright,” she asked in her pleasant voice.
“Yeah for sure. Did you want to grab a drink somewhere? Your town, your choice on pub,” I said while hearing chatter on the other end between Anna and someone else.
“Actually I have another friend here so why not just come straight here,” Anna suggested. She paused for a few seconds, listening to her friend before addressing me once more. “Just come right in, don’t bother knocking.”
“Okay…” I replied. “Text me your address in the next few minutes. I’m just waiting on my bag then I’ll grab a cab.”
“See you soon tiger,” she added before hanging up.
Luckily my plane got in at a perfect time so that it was late enough to avoid rush hour traffic and yet too early for the night-time traffic to clog the streets. Anna’s condo wasn’t too far from the airport as the cab was dropping me off on the curb in front of her condo 30 minutes after our phone call ended.
I took the lift and arrived at her door, raising my hand with a balled fist to rasp on the wood before remembering her earlier instructions left for me. Lowering my arm I instead opened my hand, clutched the knob and spun it. I didn’t meet any resistance as the door swung inside to reveal a scene that very much shocked me.
Directly in front of my line of sight, no more then 20 feet inside her condo was Anna lying flat out naked on her sofa. That alone would have been a happy finding but the surprising part was that between her widespread legs was a slender woman with red hair who was eating her out with vigor…and Anna was loving every minute of it.
“Holy mother of God,” I gasped under my breath.
Though I had said it fairly quietly my words were enough to catch the attention of the woman I presumed was the friend Anna mentioned that was visiting this weekend. It caused the redhead girl to sit back on her heels and show off that she was not only naked but a very familiar face. Her beautiful green eyes flashed towards me as she seductively used the back of her hand to wipe away the pussy juices from my sometimes-girlfriend.
“Oh hey Og. Do you know Kristen,” Anna greeted from her back. “And please close the door behind you sweetie.”
The Kristen she referred to was that of Twilight fame, which is when it clicked to me that they had shared the screen in that awful film series based on the even-worse books. Without the media knowing it, the pair remained close friends for nearly a decade since the first movie and knew that I thought about it, I could understand why…Kristen’s tongue buried in her pussy aside.
Though Anna hid it better from pop culture, she was just as big a stoner as Kristen though the Pitch Perfect star hid it better, not to mention didn’t come off as bitchy during interviews. They both had also hooked up with directors with the small distinction being that when Anna did it he was single meanwhile Kristen had public outrage as a man in position above her seduced her while married…yet she was the bad person in the eyes of everyone.
Snapping back to reality I had become aware that I had not replied to Anna. Trying to stop looking like an idiot, I picked up my jaw from the floor, wiped the drool from the corner of my lips and tried to use my words like a normal human being.
“Never met her formally,” was what I came up with. “But I know of her of course.”
“Nice to meet you,” the redhead said, still sitting naked back on her heels.
“So…you guys…do this often,” I asked, trying to hide the excitement while also focusing on stringing two words together.
“A few times, last was with my ex-boyfriend. The one that shimmered,” Kristen joked.
“You had sex with a teen heartthrob,” this time failing to withhold a chuckle.
“Sucked him, fucked him, hell was even sodomized by him. A good lay,” Anna summarized before quickly adding. “He had nothing on you though Og.”
“Appreciate you trying to spare my pride but I’m not that insecure,” I replied, seeing a wave of relief crest her gorgeous face.
“I seem to remember that you also let him pis…”
“…ton his cock between my great tits,” Anna cut her off, though I was extremely interested in having a follow-up conversation with Kristen about the actual ending to that sentence.
Looking at both women, naked in all their glory I couldn’t help but compare and contrast their stunning features. Though they were similar in that they had beautiful but slightly atypical faces and bare pussies (except for Kristen donning a thin strip) they had their differences as well.
When it came to their tits, ass and legs, the pair were opposites. They both had great bodies but Anna’s best asset were her sagless C-cup breasts, made to look bigger given her tiny frame. This was followed by her small but plump ass that was oh so biteable, and finally her legs which were slender and smooth but nothing special.
The inverse was true for Kristen Stewart though. The Twilight star had boobs that fit her slim body well, my guess being a healthy B cup, with small pink nipples but they pailed in comparison to Anna’s, as well as her own other features. She had a great rounded ass that was severely underrated until displayed properly in tight-fitting dresses but her star attribute was her gorgeous legs that were long, lean yet had toned muscles that made them look feminine but sexy.
“Now I was kinda in the middle of something so if you don’t mind getting rid of the clothes and maybe making us some drinks I’d appreciate that,” the suddenly stone-faced Kristen said to me.
I shut up immediately and watched on as a backtracked into the kitchen. A quick glance showed me a bottle of tequila on the counter with two used shot glasses nearby. I opened a few cupboards with haste and found an orange juice glass which would do for me just fine.
Only seconds had elapsed since I left for the kitchen and I had hardly missed a thing. Kristen was just finishing her liplock with her friend as her hands clutched Anna’s wrists, pinning them up over her head. It made her breasts heave upwards, a fact Kristen didn’t miss as she leaned down and took turns taking each of her nipples into her mouth.
“Shit,” Anna cooed as the other woman’s tongue swirled around her tits.
Kristen switched sides a few time before continuing her descent down Anna’s slender body, finally arriving at her destination. Her snatch was shaved smooth without even a hint of hair which made the brightness of her pink pussy look even more radiant. The red-haired star must have thought the same thing as she instantly reacquainted her tongue with Anna’s twat.
As I undid my belt buckle and pulled it free from my waistline, the Twilight actress buried her tongue in Anna’s snatch repeatedly. My pants came down to reveal my erection contained in my briefs as Kristen used her nose to stimulate her friend’s clit expertly. I pulled my polo up over my head and my eyes re-adjusted on the action in front of me, this time with the redhead using her flat tongue to lick up and down her slit.
“You are so God damn tasty,” Kristen commented. “And I think your boyfriend is ready for you slut.”
She was referring to the fact that I had stripped off the last remaining article of clothing and had my cock, standing a proud 8 and a half inches, out on full display. Anna rolled her head to the side and her eyes went wide at the sight of the dick that was now only mere feet from her face.
“There’s my favorite penis,” she said. “Uhh God Kristen that’s good.”
Anna continued to say that she was excited to see it and had been thinking about my dick but that was all drown out the second she reached out and grabbed hold of my member. She gave me a few strokes as she licked her lips, all while Kristen kept licking her. She moaned as I guessed her friend hit another sweet spot in her, all while she tilted my cock skyward to run her tongue up my underside.
The second her tongue touched me I was lost in a blissful moment. Ever since the first time we hooked up I became obsessed with her oral skills and craved them. Every woman since Anna was average or good at blowjobs but Anna was the best. I was reminded of that as soon as she opened her mouth wide and took the head of my cock into her mouth.
“That’s what I’ve been craving.”
I closed my eyes shut and savored the feeling of her talented tongue swirling small concentric circles around my crown. From her position flat on her back with legs spread eagle she wasn’t at her best, but she compensated for that with more effort. Twisting her upper body towards me she wrapped her arms around me, clutched my naked ass and used that to guide more meat into her mouth.
“That is a gorgeous cock,” Kristen said, appearing on top of Anna’s supine body.
I’d completely forgotten about the redhead though that may seem ridiculous since I knew that she was eating out my quasi-girlfriend. However, this was my first threesome and I’d lost track of her the second Anna’s hand then mouth touched my member.
“Want some of this,” Anna said to her friend lying on top of her.
I looked down and noticed that Kristen’s eyes never strayed from my cock whatsoever as the question was posed to her. They began moving together, making me wonder if they had done many threesomes in the past other then at least once with Kristen’s ex. Anna pulled her mouth off my cock and moved south to lick my balls as the redhead leaned in and engulfed my cock, freshly coated in her friend’s spit.
This time I kept my eyes open with determination to not miss a moment of this amazing encounter. It allowed me to spy Anna multitasking, using her tongue and mouth to take turns on each of my nuts while sliding a hand down Kristen’s back. If the Twilight noticed then she didn’t care as the only thing on her mind was sucking my cock and trying to milk me as soon as possible.
Anna caressed her friend’s surprisingly plump naked ass while they still worked in tandem to blow me. Her arms were short so it meant that she could only get a finger between the other girl’s cheeks and I watched as it began to make circles.
“Anna! I didn’t know we were going for anal fun tonight too,” Kristen practically celebrated.
“It’s a special occasion,” the other replied as I kept watching Anna rub Kristen’s asshole.
“You really do like this guy,” the redhead countered, sticking out and licking my pee slit to emphasize who the guy in question was. “But you know what I would much prefer.”
“I’d love to toss that salad,” I jumped in, licking my lips.
“No way. Her tasty booty is mine,” Anna retorted. “Plus this way Kristen can have some more of that cock she’s drooling over.”
I was disappointed when Anna’s mouth left my sack for good as she squirmed herself out from the bottom of the sandwich we had made. Kristen reacted by using her hands and knees to support herself now with the new position able to have her thick ass pointed up for the Pitch Perfect singer to have better access.
“Man this thing is a beauty,” Kristen commented.
The redhead didn’t wait for her friend to start servicing her before she gave me attention. Opening her mouth wide she took me between her lips before creating a seal halfway down my shaft. I could feel my tip poke her in the back of the throat but she checked her gag reflex and didn’t even cough.
She repeated the trick several times, me reaching down and holding her shiny hair out from her face while I watched. Her head moved up and down with good speed and I saw her cheeks hollow as she applied enough suction that I thought she’d succeed in literally sucking the cum straight up from my nuts.
“Fuck you’re good,” I groaned, my fist tightening in her hair.
She really was good, not as good as Anna but in the next tier beneath that God level. It also didn’t hurt that her tongue that was gliding along the underside of my tool was moaning and vibrating as my kinda-girlfriend chose that moment to start eating out her asshole. I looked down Kristen’s pale body to see her with her adorable face buried in her best friend’s thick cheeks.
“Uhhh…I love that tongue in my ass,” Kristen cooed.
I wish I could have watched as Anna’s skilled tongue danced about her puckered opening, probing every crinkle around the center. I felt a bigger grunt from Kristen, some noise escaping from her mouth filled with my cock and imagined that was when Anna made her tongue pointed and pushed inside her anus. Anna’s small hands were gripping her friend’s ass cheeks, pulling them apart to help create a gap within her tightest of holes.
“Your bum is soooo yummy,” Anna told her best friend before adding. “And I’m not just saying that to kiss your ass.”
Anna followed up that statement by literally planting a kiss on each ass cheek before placing her lips directly against the other girl’s backdoor. Kristen deserved heaps of credit because while she was receiving Anna’s best rimjob, she didn’t falter in swallowing my cock or at least the first 5 inches of it.
“Mhmm…so good,” Kristen purred before biting her lower lip.
As if being on the business end of a great blowjob wasn’t enough, I also got to watch the Pitch Perfect star continue to toss Kristen’s salad. Then there was all the gurgling noises coming from the redhead as she continuously took me as deep into her mouth as possible. The throaty sounds and extra spit she coughed up on my rod only added to the great experience.
“Hearing you suck my boyfriend’s cock is making my pussy so wet,” Anna moaned from behind her friend.
“Then how about I take care of that for you,” I proposed with a predatory smile.
“Yes please,” Anna said.
The auburn-haired actress gave Kristen’s asshole one last good lick before slapping her bottom playfully while getting to her feet. The redhead released her lip lock on my cock and allowed me to walk over to Anna, who I immediately embraced in a passionate kiss for the first time that night.
We broke the kiss when I felt her hand close around my very wet cock, courtesy of Anna’s best friend. Her hand slide along my pole with far greater ease then before, helping to keep me hard, not that the circumstances alone wouldn’t have worked. Opening my eyes, I became aware that Kristen had also stood and was now directly beside the fellow actress.
“I can’t wait to watch him fuck you,” Kristen told her, following up her slutty words with a tongue-filled kiss.
“Bedroom,” I blurted out.
“This way,” they replied in unison.
Anna clutched Kristen’s hand as they started off towards Anna’s bedroom. It was only a one room condo so I had a 50-50 chance of picking it but I figured that they could lead. I followed shift on their heels as the auburn-haired singer turned right and opened the door. Her bedroom was nothing special, a large king bed in the middle of the floor but it would fit the bill perfectly.
While I watched Anna crawl onto her plush bed Kristen grabbed the back of my head and pulled me down for a kiss. I realized just how small she was given how low I had to stoop to press my lips against hers, but I banished that thought when our tongues started mingling.
When he separated less than a minute later I found the auburn-haired actress on her back with her knees bent so her calves dangled over the edge. I couldn’t wait any longer but before just slamming into her I squatted down and ran my tongue through her folds and confirmed she was gushing just like she had said earlier.
“God yes,” she moaned as he entered her.
This time I grabbed my cock around the base, climbed on top of the much smaller girl and buried myself inside her in one push. Kristen had done a great job prepping her which allowed me to ramp up to pounding into her tasty snatch with raw power. Anna was powerless to do much other than arching her neck and back while her loud screaming echoed around what I hoped were soundproofed walls.
I didn’t want Kristen to think I forgot about her but she had read my mind. As I looked over at her she jerked my head towards her and our lips met with yet another explosion of passion, which coincided with her pussy getting wetter once again.
I had risen up higher onto my knees to draw level height with the slutty redhead, however it didn’t mean that I neglected my duty with Anna. The slight variation on missionary position still allowed me to penetrate her just as deeply, albeit at a loss of some speed.
“Shhhhhit,” Kristen groaned as two of my fingers entered her snatch.
The fiery redhead began moaning repeatedly into my mouth while Anna’s screams were still ringing out around the room. It seemed like the more passionate I kissed Kristen I would respond by spiking my dick as far as possible into Anna’s mound.
“Oh…mhmmm…feels so…amazing,” Anna cried out as I continued to plow into her from behind.
“Let me taste her from your cock,” Kristen begged, already in position.
Anna ran a hand through her long shining hair and nodded her head to me as if giving me the go ahead to pull out. I wasn’t really looking for permission but I stepped back from her and turned to the side where Kristen pounced on my cock with her mouth once more. I looked down and saw her savoring the juices coating my member, clearly loving every drop of Anna that remained on my cock.
“My turn,” Kristen said after bobbing on my length a few more times.
“Wanna fuck you now,” I huffed in confirmation.
Kristen gave her best friend a look and it seemed like Anna knew exactly what she wanted from her as she pushed up the bed until her head rested in the pillows. Kristen was up next on the mattress as she crawled so her head was in between Anna’s spread legs, a position she seemed to love to be in.
Though my vision of them was being blocked for the moment, I could tell when Kristen started licking my girlfriend when her beautiful face contorted into that of pure pleasure. Standing up tall I was now able to look over the redhead’ body and watch a her mouth sealed around Anna’s pussy and ate her out expertly.
“Yes…mhmmm….ohhh,” Anna moaned. “Such a good carpet muncher.”
I enjoyed the show but looking down Kristen’s skinny but curvy-in-all-the-right places body made me need to snap into action. Not wanting her to feel left out I leaned down to lick her twat to be sure she was prepared for me. After a few swipes of my tongue I realized that the Twilight star was a fountain between the leg and ready for me.
At the risk of sounding cocky, I was concerned with giving into my animalistic side right away and pound her as hard as I did with Anna right away mainly due to the hugeness of my manhood. She was also tiny so I decided it would be best for to start at a lower pace, at least to start with.
It was tough to rein myself back but I accomplished the goal until after a minute I was stroking my entire length into the slender actress. However the second my hips met her surprisingly curvy ass, she flash me a look that portrayed she a ready to go.
While yet to ramp up my speed, I was able to watch the redhead I was fucking eat out my girlfriend. After enjoying the Anna’s impressive oral sex from earlier in the evening, Kristen didn’t hesitate to repay the favor, not that she ever need a reason to eat out her gorgeous best friend. I could watch as she ran her tongue through the Pitch Perfect star’s folds, which made Anna shudder and moan in appreciation.
Kristen used her fingers and pulled apart the other girl’s labia. I could tell that she got such a thrill seeing how pink her hole was especially in contrast to her hairless white skin around the opening simply because it evoked the same sentiment in myself. After taking another moment or two to marvel at the beauty, Kristen dipped her tongue into Anna.
“Mmmppphhh,” Anna mumbled deep into the pillow she pressed against her face.
“I think she said ‘thank you,’” I translated to Kristen.
I also used that moment to crank my rythym up to full speed as to actually start fucking the movie star hard. She moaned sharply, surprised by my new tactic, but settled into it as illustrated by the fact she was rocking her petite body back against my pistoning hips. Her meaty cheeks rippled under our combined force as we both seemed pleased with the faster pace.
I had the urge to reach down and pull the slutty girl’s hair but I noticed how much she had Anna squirming. Since we had been hooking up for over 6 months I knew when my girlfriend was getting close to coming so I didn’t want to slow her pending orgasm. However that didn’t stop me from giving Kristen’s curvy hips a death lock as I slammed her backwards to skewer her gushing cunt on my rod.
“Fuck you’re a good lay,” Kristen complimented, pussy juice slathered around her lips.
As I felt the compliment wash over me and perk up more energy to maintain my current pace, I saw Kristen putting the finishing touches on her friend’s pending orgasm. She moved her mouth back up to Anna’s clit and lashed it with her tongue all while her two slim fingers blasted deep and repeatedly into her snatch,
“Yesssss…..MMMHHHMMMMMM,” Anna screamed into her pillow once again as she climaxed.
Kristen had just made her best friend cum and now she was after another orgasm, this time her own. She removed her fingers from Anna’s twat and brought it between her legs and used the vast amount of cum on them to smear around her clit. The stimulation of her sensitive nub combined with my thick cock pounding her relentlessly was enough to have her orgasm as well.
“Good job babe…Kristen doesn’t cum easy,” Anna congratulated me.
“Ever had that big cock sucked by two girls at the same time,” Kristen asked me, looking back over her shoulder after they had both recovered somewhat after cumming.
“No. Never,” I answered honestly.
“Then it’s your lucky day, big boy,” Anna cut in.
In the blink of an eye both beautiful women had sprung off the bed and onto their knee in front of me. This time, Kristen didn’t let Anna have the first go around with me like she had been doing the rest of the night. Opening her mouth, she picked up where she left off earlier and allowed half my dick in one go.
Much to my pleasure her bobbing on my length was as intense as ever. Though she didn’t take me all the way don like Anna could, she made up for it with pure energy. Her effort burned bright for a minute before she pulled away from me and angled my cock toward the auburn-haired singer.
“Yeah…suck his big dick Anna,” Kristen encouraged.
Anna didn’t need the instruction but it appeared that both of us got excited by the dirty talk from the stoner. The Pitch Perfect star rose to the occasion in being in essentially a head-to-head competition with her best friend by loosening her throat and taking me all the way inside, which I responded by releasing a torrent of grunts.
Yet it didn’t take the Twilight star long to show off her dominance. Shortly after turning me over to Anna, the redhead sent a trail of kisses up along the deep-throating girl’s neck until following along her cheek. By the time she made it to the edge of of her mouth, Anna was returning the kiss.
“Oh my God,” I groaned at both the sensation and show on display.
With her lips still partially around my bulbous head, Anna and Kristen were making out. The two girls each had part of their lips on each other’s mouths but also were both on my penis, making me a very happy person for obvious reasons. Their tongues were wagging wildly as they alternated from wrapping around each other and also dancing along the sensitive tip.
Kristen was more aggressive then her best friend so it didn’t take her long to edge the singer away from the prize. The red-haired stoner was now assertively in control of my long dick and taking a healthy portion of it into her mouth. Not wanting to be left out in the cold, Anna wrapped her lips around the last few inches of me not occupied in the other girl’s mouth.
Kristen wasn’t wasting her chance in the driver’s seat as she energetically sucked on my long cock. She kept alternating between super-fast, shallow strokes using her lips but then would take me deeper into her mouth so that her lips would butt up against Anna’s.
“You like having your fat dick pounding the back of my slutty little mouth,” Kristen seductively asked as she allowed Anna another turn blowing me.
“I think he prefers actually going all the way down my throat more,” Anna cut in, fresh from doing what she had just described.
“It’s normal to have a gag reflex,” the naked redhead spat in response.
“How cute. I remember when I had one of those…in grade 8,” Anna laughed.
“Okay as much as I love the friendly banter I really want to fuck on of you again,” I urged.
“Since my whore of a best friend got you all lubed up well with her spit, how about you fuck my tight little ass,” Kristen offered.
Before I had even agreed the redhead was getting into position on the large bed. I joined Kristen on the mattress with the two of us laying on our sides with her much smaller frame against my powerful chest. My dick was glistening in the dim lighting due to Anna’s spit covering it but to make sure she was prepped the redhead transferred a lot of her own saliva to her fingers before reaching back and smearing it around the outer ring of her anus.
“Come on…it’s not going to fuck itself,” she said with a cocky grin.
I didn’t waste a second of time as I gripped my base, placed the tip against her crinkled entrance and pushed until the first third of my thick cock was planted in her ass.
“Oh God you’re huge,” Kristen groaned as I slowly worked myself in and out.
“Yeah you won’t be sitting comfortably for a few days,” Anna said from the corner of the bed.
I continued to slowly work into Kristen’s rump mainly because I knew that going too fast too soon was asking for trouble. However when I felt the redhead push her ass back towards me so that she was taking half my dick in her booty I figured she was ready for more.
Anna must have been reading our minds or our body language because she was on the same page as well. Leaning herself downward so used her skilled mouth one her best friend, wiggling her tongue up and down her pink slit no more than a few inches away from where my cock was spearing into her bowels.
“Fuckkk…you two know how to treat a lady,” Kristen moaned.
I also let out a groan as I felt my dick bury further in her tight anal walls and once I had a taste (so to speak) of her asshole there was no way my urge could be satisfied. Blocking all other thought from my mind, I relentlessly pounded into the Twilight star’s backdoor. To Anna’s credit, she had selected a high caliber slut for a best friend as Kristen seemed to take the plowing and kept encouraging me to go harder and faster.
“So tight,” I announced while continuing to work more cock into her hole.
“It feels so good,” Kristen cooed, still enjoying mine and Anna’s dual efforts.
“Slut,” the Pitch Perfect actress said to her friend, having taken a brief break from eating her twat.
“I may be a slut but I’m the slut that your boyfriend is fucking right in front of you,” the redhead bantered with Anna.
I was curious what Anna was going to do about that comment but she simply laughed about it. These two clearly had a unique relationship, not that I cared since it allowed me to be balls deep in her best friend’s asshole while she ate her out like a submissive whore.
“I’ll make you pay for that later,” Anna replied to her quip.
“Yes my clit! Lick my clit,” Kristen instructed Anna before turning her head to address me. “And you keep that dick deep in my ass.”
The two of us listened to the bossy star’s orders and carried them out to the tee. I was pleased that the girl was close to cumming, which seemed to re-vitalize my fleeting energy to some degree. As I kept plowing the deeper reaches of her bowels, Anna copied her best friend’s earlier oral work by clamping lips around Kristen’s clit and combining motions of sucking and licking.
Kristen’s fine ass was rippling with the force of my every thrust each time my cock disappeared past her muscular ring. It was such a surreal sight seeing the speed at which I made my cock impale her asshole given how tiny the actress truly was, not to mention that she was loving every minute of the sodomy.
“Make me cum in your girlfriend’s mouth. So close,” Kristen spewed at me. “Go back to my pussy now.”
Anna listened to red-haired girl and quickly moved her lips off of her clit and back down to her hole. By the time she reached her tongue back inside, I felt Kristen start to jerk before she unleashed the loudest scream of the night.
The Twilight actress gasped loudly then seemed to begin chanting some unintelligible babble as she came. Her juices flowed down right into Anna’s mouth, where my auburn-haired beauty seemed to greedily drink down each drop of the other girl’s cum.
“My turn,” Anna exclaimed after finished licking all the cum from Kristen.
I wasn’t going to turn that offer down but I had barely pulled out of Kristen’s ass when Anna had stepped over her exhausted body and rolled me onto my back. I had no problem with her energetic attitude as she swung her slender legs on either side of my muscular body and sat on my lap.
I pulled her head down and kissed her passionately for the first time in what seemed like a long time. As our lips stayed locked together I felt her dainty fingers close around my ass-soaked member as she lined me up with her hole and sank down. To my surprise and delight, it was the second asshole of the night that I had penetrated.
“Always forget how great your cock feels in my ass,” Anna cooed as we got started.
“Ditto,” I grunted as her tighter backdoor squeezed my dick with all its strength.
We didn’t have the added benefit of my dick being wet from a sloppy blowjob like when I first ass-fucked Kristen so Anna and I had to go a little slower. We’d had anal sex before so it wasn’t like she couldn’t handle my thickness in her tiny little ass, but the lack of lube meant I wasn’t thrusting my hips upwards to fast until she loosened up more.
Luckily Anna was relaxing more by each passing short thrust into her booty. Little by little her dirt road opened further, allowing me to get over half my length up into her ass without difficulty. I placed both of my strong hands on her small cheeks and pulled them apart with as much strength as I had, which did the trick.
“Holy God. It’s all in there,” Anna exclaimed as I was buried to the hilt in her backdoor.
“You like my cock in your ass? Want me to fuck you harder,” I asked.
“Yes baby…fuck my ass,” Anna replied.
I took her up on her request and withdrew until only my head remained in her anal canal. This time I thrust into her in one sudden swoop so that I could feel my hips pressed against her plump cheeks. Anna let out a quick gasp but by the time I repeated the action two more times she was now emitting long, low moans.
It had been a long night sexually and I could feel my own orgasm approaching but for now I was doing my utmost to simultaneously hold off my release as long as possible while making Anna cum for a third time tonight. I was gritting my teeth due to how good it was feeling to stroking my entire length into Anna’s tight backdoor. We had built up to a steady penetration rhythm as the slim girl’s asshole repeatedly was impaled by the biggest cock that she’d ever had inside her.
To help distract myself a ran a hand up from her plump ass cheek over her taut stomach to knead one of her bouncing tits. They felt heavy in my hand as my fingers dug into soft flesh before a focus my attention on rolling her nipple between my thumb and fore finger. It served to make Anna moan louder, as well as grind her hips back and forth on my cock next time she sank right down onto my lap.
“Jesus…won’t last much longer,” I admitted.
“Little more…so close,” my favorite sex puppet replied.
My endurance was almost ebbed completely away but I was the determined sort and was going to make it happen. Remembering again what would get her there, my free hand rolled from her hip to between her legs and instantly found her clit. I rubbed her snatch so quickly that I feared it was painful, but Anna only felt pleasure.
“Cream inside her,” Kristen’s voice dictated.
The stars must have aligned because my stubborn endurance was on the verge of maxing out as well. And luckily for Anna, as I edged closer to release my nipple play got harder too and that turned out to be exactly what she needed in tandem with my nearly frictioning off her clit.
“Yes baby…fuck my ass…fuck my ass…fuck my ass,” she screamed in steady encouragement.
To keep up with her demands, which detailed pistoning my cock in and out of her asshole at ridiculous speeds, had finally reached its breaking point. I did a thrust into her one last time then stayed buried inside her vice-like sphincter closed tightly around the base of my cock just as Kristen instructed.
“Awwh….shittttt,” I grunted while cumming deep into her bowels.
As the first streak of cum plastered itself on her rectal walls, Anna came again. With my grip on her small but very hard nipple nearly doubling as I came, the auburn-haired girl was pushed past her point.
“Shhiiittt….I’m CUMMMINNNNGG,” Anna screamed.
I could tell Kristen waited until we had both cum before she sprang back to life, albeit much slower then before. The redhead pulled my cock smoothly from her best friend’s booty and placed it right into her mouth as she bobbed a few times with deliberate motion before taking it out and licking up both sides from base to tip.
“Your dick tastes so good though,” Kristen commented.
“Actually I think that’s my asshole you’re enjoying so much,” Anna chimed in, her exhausted body pressed against me.
Kristen shrugged her shoulders to concede the point to her friend before descending her head back onto my sensitive tip. I shuddered from her wet attack but it didn’t last long as she moved from me onto Anna.
With my cock free from her asshole Kristen twisted her neck so that her lips were pressed around the outside of the Oscar nominee’s rectum and waited patiently with her mouth held open directly underneath the gaping hole. It only took a handful of seconds before Kristen moved out from under the other girl’s ass with the prize she sought.
However, rather than swallow the mouthful of cum she had collected from the deep recesses of Anna’s ass, Kristen held it in her mouth and went in to kiss her gorgeous friend. Anna dipped her head towards the redhead to kiss her back, all this while still laying on top of me.
The Pitch Perfect was surprised, but in a good way, when my cum was spat into her mouth. With a flash of her large eyes to Kristen, I watched as Anna swallowed down the salty load in one big gulp.
“Yum,” my girlfriend purred.
I’m not too sure what happened the rest of the night. I remember getting to my feet at some point and stumbling into the washroom to piss before returning to the bedroom. I barely remembered to set my phone’s alarm for my early wake up call tomorrow before passing out sandwiched between the two gorgeous women.
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Dating Anna Kendrick