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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
- 3
- 4
- 5
Summary: In order to get her lesbian lover Cara Delevingne on board with anal sex, Kristen Stewart brings her to a man she knows is exceptional at it.

I yawned as I rose from bed before stretching my arms high and back. I had another good sleep, albeit lonely with Anna Kendrick, my girlfriend, out of town filming yet another movie. We were getting more and more serious, with me even going to visit with her on her various movie sets, however I had work on my own set this weekend.
Unlike Anna, I work behind the scenes. I like the work, it keeps me connected and in frequent contact with beautiful women and in the field that I love. I’m not an actor as I’ve never been comfortable in front of an audience, but as an assistant learning the trade of a filmographer I completely thrive.
BUZZ BUZZ
“Who’s texting me at this unGodly hour of…9am,” I said aloud to no one.
Company coming in 15. Be awake and showered. Trust me and play along.
I had thought when I heard my cell buzz that it would be the adorable actress I was dating, instead it was her bitchy but hot friend Kristen Stewart. I hadn’t seen the fiery redhead in months, not since she, Anna and I shared my bed for a steamy threesome. But why she would be coming over to my place when she knew Anna wasn’t here made little to no sense.
“Shower time,” I said, raising from the bed.
Even as I had a quick cleaning I still couldn’t figure out why Kristen was coming over. And why I had to play along with some scheme of hers. She must have company with her was the only thing I could reason.
I had time to shower, get dressed and make a quick breakfast burrito. It was Saturday so I normally would have slept in a bit later after working long hours all week before doing typical weekend chores like tidying the house, grocery shopping and the like. Hell, I wouldn’t even have time to watch Sports Center!
KNOCK KNOCK
It was good enough timing as I had just finished boiling water and grinding my coffee beans, combining them in my French Press to brew for 10 minutes. I didn’t look through the peep hole knowing who it was already, but instead of just Kristen Stewart, there was a second recognizable girl with her.
“Sup Og. Anna around,” Kristen asked, already showing herself in.
“Hey to you too,” I said to the somewhat pushy redhead before turning to address her friend. “Hi, I’m Og.”
“Cara,” the leggy blonde replied, shaking my hand.
I had just seen Suicide Squad plus hadn’t been living under a rock so I had instantly recognized the model-turned-actress as Cara Delevingne. Just like on screen, the girl had a gorgeous face, fit body and the longest, most perfect legs I’d ever seen on a girl in the flesh. And despite being a model she had curves complete with a more-than-decent rack and a surprisingly bubbly ass.
“Oh right, Cara that’s Anna’s boytoy. Og, this is my girlfriend,” Kristen said, getting around to introducing us.
“And Anna is away…”
“Shit she got called in to set,” Kristen said, interrupting me and adding in a lie.
“Yup. Total last minute thing. I guess she didn’t warn you,” I added, remembering her text message.
“Such a forgetful slut,” the redhead replied. “Shit…I’m getting buzzed. Gonna use your room.”
Kristen was pulling out her cellphone as she disappeared into my bedroom and closed the door behind her. Cara and I shared an awkward look of two people who were just meeting for the first time and suddenly left alone without having a single thing to say. Realizing I should break ice, I cleared my throat.
“Loved you in Suicide Squad,” I said, that being the first thing that came into my mind. “And Paper Towns.”
“Thank you,” she said, her English accent bleeding through. “I was nervous and the CGI was crap…but that’s just between us.”
We talked a little more and I found her in stark contrast to Kristen in some ways, but similar in others. Even after a short time I could tell she was sweet and playful, but she was also self-confident like her girlfriend, as well as direct and unapologetic. It also took all my willpower to not try picturing the two of them together…in bed…with Cara’s long legs wrapped around Kristen’s head.
“You look lost in a thought,” the model observed.
“Suddenly was trying to recall the lineup of the 1994 New Jersey Devils’ Stanley Cup winning team,” I answered truthfully as that tended to stop my growing boner from getting noticeable.
“Fuck fuck fuck,” Kristen swore as she stormed out of the bedroom.
“What’s the matter love,” Cara asked.
“Seems like getting called to set and ruining a perfectly good Saturday is contagious today,” the lesbian answered before sharing she got called into a meeting for her upcoming picture.
“That’s shitty,” I replied, very confused.
“Og, can I ask you a favor? Would you mind entertaining Cara as I run off to this meeting. I shouldn’t be any more than 3 or 4 hours total,” Kristen asked.
“I’m cool with it if you are,” I answered looking over at the Suicide Squad star.
“Better than sitting at the studio, bored to tears,” Cara added. “Thanks Og.”
“Og, can you go pour Cara a coffee that I can smell,” Kristen commanded more than asked. “Two sugars, one milk. Thanks.”
I still had no idea what was happening but I continued to trust the actress for a little while longer. Why was she trying to pass Cara off on me? Was she trying to create distance between them? Not wanting to hang out with the model anymore? These were just some of the questions I thought as I poured to mugs of coffee. But after getting the milk from the fridge, I heard the two lesbians talking.
“Seriously Cara, don’t,” Kristen said in a more authoritative tone. “I know we don’t care about monogamy but he does, and so does Anna. Og is completely hands off.”
“Okay, okay. No need to get all bitchy about love,” the model-turned-actress agreed.
“Alright, my bad,” Kristen replied before I heard a soft kissing sound. “He’s a good guy and cool so I’m leaving you in good hands at least.”
“Your coffee,” I offered the mug to Cara as I re-entered the room.
“Thank you,” the model said, accepting it.
“A word Og,” Kristen said as she picked up her purse and headed towards the door.
“Kristen, what was that about? It’s not like I would actually try to fuck your girlfriend but you didn’t have to lie to her to get her to keep it in her pants for your benefit,” I told the redhead.
“Oh Og, so handsome and yet so dumb,” she said, completing the patronization by patting my cheek. “I did that for your benefit. By telling her that you had off limits, it’s making her so horny that she’s gonna throw herself at you.”
“Okay…but why? I didn’t even get the feeling you liked me…at all,” I followed up, trying to make sense of it.
“I don’t, not really. However, I can appreciate your talents,” Kristen looked over her shoulder to make sure Cara wasn’t around then continued. “We can use each other here in a mutually beneficial way. You get to anally fuck my hot, lesbian girlfriend and in return I get back Cara who is willing to experiment with butt stuff now.”
At this point my head was spinning. Not only did Kristen Stewart want me to plow her girlfriend, but sodomize her as well. She went on to explain that she’s been dying to play with Cara’s asshole, especially with her favorite strap-on, but the leggy model has rebuffed her at every chance.
Then she thought back to how great of an anal lover I was. In fact, with the way she remembered it fondly plus the way Anna gushed about it, Kristen knew I’d be perfect. Anna was a lot of things but she wasn’t known to withstand a hard fucking, but Kristen had vivid memories of me laying wood to her ass fast and deep…and her loving every second of it.
“So just return her loving anal…or else I’ll come back here in the middle of the night and crush your nuts with my bare hands,” the fiery ginger added.
“So let me get this right. I’m to seduce your girlfriend then be her anal trainer,” I replied, still in disbelief.
“Yup, couldn’t have put it better myself,” Kristen replied with a cheery smile. “By the way, I left you some goodies in your sock drawer to help when it’s time.”
Within minutes Kristen was out the door and going God knows where. Maybe she actually did have a meeting that she scheduled behind Cara’s back in order to get me and the model alone. I have no idea how her devious mind worked, but I knew what I had agreed to so I racked my brain as to how to start.
“Cool, you have Smallville. Mind if we watch some,” Cara offered.
“Yeah of course,” I replied, figuring it would be like research for her.
“Is my character Enchantress in any of them?”
I racked my brain as I thought back over the 10 season show before answering in the negative. However season 8 had some Suicide Squad storylines so I suggested that to the leggy actress and she was more than happy to settle for that. She had fallen in love with the character and team during filming and now wanted to absorb all source material.
We both sat on the sofa as I flipped through the episodes until finding Suicide Squad centric episodes of the corny yet genre defining show. IT had some members from the film like Rick Flag and Deadshot, but sadly I was right and there was no Enchantress. Throughout the few episodes we moved closer and chatter easier, getting to know each other better and even flirting some if I detected right.
“Can I use your bedroom for a moment,” Cara asked, already standing up.
“Um…yeah, of course. Right through there,” I said, pointing the way.
I couldn’t help but watch her tight ass as she rose from the sofa, grabbed her purse and swayed her way to the room. Her legs really did go on forever I noted as they emerged from under her short sun dress.
I continued to watch the movie but after a few minutes I began to wonder what happened to the leggy model. She was probably just on the phone, probably with Kristen. Maybe she was pleading with her girlfriend to cancel the meeting and come back. Maybe she was bored. Was I boring her?
“Og. Can you come here,” Cara called from my room.
Wondering what she was up to, I rose from the couch and opened the bedroom door to a sight I most definitely wasn’t expecting. Changed out of her casual dress, Cara was laying on my bed with one of my dress shirt completely unbuttoned but just covering her breasts. Her only other remaining clothing was a pair of long black socks that went to her mid-thigh, meaning I had an unobstructed view of her hairless pussy that looked as pink and inviting as I had ever seen.
“Cara…wow,” I gawked slackjawed.
“Well don’t just stand there silly. Come on in,” the model instructed.
Like a mindless idiot I walked into the bedroom, my eyes never leaving her body. I glanced at everything from her face that wore an expression that begged me to take her right then and there. Then continued down to stare at her naked breastbone, the hint of her inner tits just visible before my shirt covered the rest. And of course that bald cunt!
“What…um…are you doing,” I asked, slowly recovering.
“Seducing you,” she replied matter-of-factly, her hand between her legs and playing with her pussy.
“I can’t” I forced myself to say, putting trust in Kristen.
“Why? Don’t you like me,” Cara replied.
“It’s just that…well I kind of have this girlfriend…and we are, well, together,” I stammered, that not being an act.
“I don’t want you to think about that right now. I just want you to think about this.”
She had sat up straight so that she could reach up and take my chin between her thumb and finger. With being both firm and gentle at the same time, Cara guided my face down towards her. She gave her lips a lick to wet them before she pressed her mouth to mine as we kissed for the first time.
I had never tricked a girl into giving up her anal virginity to me so I was playing everything here by instinct. Therefore, I allowed us to kiss for awhile longer, letting her anticipation build while also giving her the impression my will was all but broken. As our tongues began to dance in the interspace between our lips, I pulled back suddenly.
“I can’t do this Cara. I love Anna,” I acted though meaning the second part.
“She doesn’t have to know,” the leggy model replied, kissing my neck.
“But I would.”
“Og, I’m so horny and want a cock. Please! Fuck me, I’m literally begging,” Cara pleaded, grabbing my wrist and placing my hand between her legs to feel her very wet pussy.
“I…don’t think so.”
Cara seemed out of ideas, I no doubt believed she didn’t think anyone could have withstood this amount of pressure. We both knew she had one last card to play but I wanted her to play it, not for me to prompt her. I realized I was still stroking her velvety folds so I stopped and was starting to pull my hand away when she broke.
“What will it take,” she asked, looking me right in the eyes. “I’m willing to do anything.”
That was the ticket I was waiting for and she finally gave it to me. Instead of pulling my hand away, I left it between her legs but instead of rubbing her snatch once more, I went even lower until the pad of my middle finger could reach out and rub her crinkled starfish. To the model’s credit she didn’t flinch at all as I began making small circles around her asshole, just holding my stare the entire time.
“Is that what’s it gonna take,” Cara questioned, the intensity in her eyes making my dick harder.
“Yes. If I’m going to cheat on Anna…you have to give up your ass,” I replied, hoping (correctly, I found out later) that Kristen had told the girl about my prowess with giving girls pleasure through anal.
She fixed me with a long stare as if weighing if that was worth it. Finally her hand went to my crotch and began rubbing my already hard cock. “Wow. No, no anal. You are way too big for my little ass. And just think how tight my pussy will be, I’m a lesbian after all. It’s practically untouched.”
I couldn’t help but grow even harder between my legs at her last comment. Her snatch would probably be the tightest I would ever experience based on the fact a cock wasn’t a frequent visitor inside her. Plus she was so thin and yet athletic. Plus it looked so tasty! But no, I had a deal with the devil…errr Kristen in place.
“But you said I could do anything I wanted. And that is my condition. You clearly wanna have fun and I can guarantee that not only will you like it, but I’ll make you cum,” I pleaded, hoping that I could back everything up.
“I don’t know. I haven’t done anal before,” she reconfirmed.
“How about just a finger? Look how small it is,” I said as I showed her my thumb.
“You think I’m so foolish? It’ll start with just your thumb then you’ll get caught up in the moment and go too far,” she claimed. “First it’ll be one finger then you’ll add a second then you’ll ask if you can see if the tip fits. So no anal.”
“Just one finger and I’ll stop pressuring you,” I retorted.
I saw that there was a weakening of her will so I pressed on, wanting to break down that wall altogether. Keeping her mind flooded with sex I started to really rub her pussy and kiss the side of her neck. I could hear her moan with this so I upped the ante further by using my free hand to push my shirt from her body and grope her firm, perky tits.
After a bit of thinking, Cara finally answered, “Okay but just a finger.”
I could tell that Cara was concerned, but how could I not be overjoyed that she had actually said yes. Needing to make sure I kept things moving along before she thought twice about the arrangement, I got her quickly set up on hands and knees with me directly behind her plump, rounded ass.
I no doubt believe she could hear me wet my thumb since I could, but I had to be sure to transfer as much spit onto the digit as possible. She couldn’t help but jump a little bit when she felt my palm contact the top of her ass. I slowed down and just rested his hand there until noticing that the model had calmed herself. Slowly lowering my thumb downward, I stopped when it was pressed against her tightly clamped butthole.
“Just be gentle,” she pleaded softly, looking back over her shoulder with her gorgeous eyes.
Nodding in agreement, I started to apply pressure. I knew she was still rather tense, but the combination of my urges and her not backing out made me press on until I saw that the hole was starting to gradually expand until finally the first part of my thumb disappeared inside her backdoor altogether.
“Ugghhh…awww,” Cara moaned as my thumb slowly was worked into her virgin hole.
“See. I told you it wasn’t that bad,” I said to her after a few more moments of pushing the thick digit into her rear and getting very positive groans as a result. “In fact, I knew you’d like it.”
“Mmm…yeah I like it,” she admitted honestly with lust in her eyes as she looked back at me. More than her confirming words and sexy look, it was her wide smile that was so telling.
“How much do you like it,” I asked, burying my thumb all the way into her asshole.
“A lot…ahhh,” she groaned.
“Enough to let me try something…similar,” I proposed.
When Kristen had pulled me aside, she had mentioned she had left a bag behind in the room with all types of toys including something I recognized from when she and Anna fooled around. Pulling the red beads from the bag, I held them up so that the leggy actress could get a good look at them, then I placed my thumb next to it as a size comparable. It was true that the beads were slightly larger, but not by a lot.
“Og! You naughty boy. Beads,” she continued to exclaim. “You want me to put these in my ass?”
I did and I told her as much before handing her the toy that consisted of 4 spheres all connected by a string running through the center of each. I wanted her to hold them and see how non-threatening they were, while also serving a purpose. While it was true I really wanted to see them buried in her tight little ass, it would also loosen up her bowels for when I tried putting my larger dick in her.
“But you said just a finger,” she threw my words back at me from earlier.
“Just put them in your mouth, it’s really no bigger than my thumb,” I retorted.
Even as I was saying the words I was grabbing the end she wasn’t holding and bringing it up to her face. Like the submissive girl she was she parted her lips and let me place the ball onto her tongue before closing up again. Seeing the little grin on her mouth as she spat it out, I asked if she could fit more than one inside.
Cara may not have been an anal-craving slut, but she was sexually confident and very playful. Seeing it as a fun little challenge, she took back control of the toy and surprised me by fitting a ball on the inside of each cheek and a third on her tongue before closing her mouth. She decided to have some fun and slowly pulled them free, going slowly so I could see her plump lips sexily slide over the surface of all three.
“See. It’s no big deal.”
“Yeah well my mouth is a whole lot bigger than my butt,” Cara replied, slapping her ass to make her point. “You saw how tiny it was.”
“But the elasticity…”
“Ugh! Men! Just go get me a bottle of the cheapest liquor you have,” Cara groaned though I doubted she was that upset.
I couldn’t believe my ears. The plan to gradually work her up to allowing me to put my cock in her ass was actually working. I guess it was aided by the fact that the gorgeous model appeared to be a sex-craving whore, but that shouldn’t have surprised me given she was dating Kristen Stewart of all people.
Not wanting to push my luck with the beautiful girl, I got up from the bed and left the bedroom to go into my liquor cabinet. There were a few options, in fact more than a few given how Anna loved getting drunk, but I ended up picking a pint bottle of whiskey. Rye in fact from a visit to Canada but it would easily do the trick.
“How’s this…”
I cut my words off in a hurry when I saw that Cara was now laying on her side, legs pressed together and ass towards me. While the sight of her naked little booty and cute dimples on her low back were enough to make me blush, what made my jaw drop was the red string dangling on one cheek and the rest obviously hidden behind her sealed tight sphincter.
“Still can’t believe I’m doing this,” the slim actress commented as she reached her hand towards me. “Give me that.”
I handed off the bottle of amber-colored fluid and before I settled on the bed behind her she had the cap off and a healthy mouthful swallowed down. With both hands free I grabbed the string that was dangling out of her and held it firmly as my eyes never left her ass…more specifically her insanely tight asshole. How she managed to get all 4 balls in before I got back was a mystery.
“Just go nice and slow,” she told me before choking back another mouthful.
“I’ll be gentle. You just pull your cheek apart,” I urged.
I wasn’t surprised at how much effort it was taking to overcome her muscular ring especially with how slowly I was going. Maintaining steady pressure backwards I switched my gaze between her asshole and face before I saw my efforts rewarded. Cara’s face started to contort with her brows furrowing and her mouth gaping as her asshole did likewise and the faintest hint of a red ball could be seen inside her.
Still pulling in a smooth motion, I kept going and watched as her asshole continued to expand and more red came into view. I think I told her to spread more as I saw the veins in the back of her hand pop but it did the trick. Her sphincter opened to its new limit as a lubed-up red sphere came popping out from her backdoor.
“Hhhh….ahhh,” Cara moaned as the first bead left her ass.
“That’s one,” I celebrated, taking a break from pulling. “Ready for the next part?”
“Wow. Okay, not horrible. Yeah…ughhh…yeah,” she groaned as the next part was slowly withdrawn from inside her rectum.
I hadn’t waited more than a heartbeat after she said yes and had pulled the second ball loose with less effort than the first while still being sure to be gentle. But as it came free of her backdoor, I couldn’t help but smile in surprise since the slutty model was clearly liking it as much as she was.
“Here we go again,” I warned before slowly starting to rear back on the string.
“You like that? You like watching it come back out of my ass you dirty, dirty boy,” the model dirty-talked. “Awhhh…oh my God…ahhhh!”
This time I went even slower, but only once I saw the third red ball start to open her asshole. As she slowly expanded I practically crawled to a stop so that she could really feel me opening her tightest of balls with the lubed-up toy then held it steady as it reached it’s apex, gaping her more than an inch before pulling it out and watching her seal back up but less quickly this time.
“Last one,” I said as I pulled.
This time we were both aware of what I was playing at so as I nearly stopped with the ball holding her ass as far open as it could go, Cara pulled back hard on her ass cheeks. The 4th and final sphere slipped out of her loosened butt and fell to the bed below.
Wanting to show her what she had just accomplished and to be proud of it, I lifted the string of 4 anal beads up towards her face. I was once more shocked by the model as she clutched my wrist and kept guiding my hand towards her face until she was close enough to take the first bead in her mouth. Like before, she ended up with 3 between her lips…3 anal beads…fresh from asshole…seconds before hand!
“Have any more cool toys in your goodie bag down there,” Cara asked after spitting out the beads that had just been down her dirtroad.
As a matter of fact I did spy a toy that would be perfect for the model before graduating her to my cock, which would now definitely be happening. Reaching inside once more this time I revealed a bubbly black dildo for her to see. It was roughly 6 inches long with each inch bigger than the first with it beginning the size of his thumb and bubbling larger as it went back until it was the size of an egg.
“Holy crap! That’s so big,” she gawked, grabbing hold of it. “And heavy! You really think I can fit this?”
The fact that she asked the question instead of outright refusing was the only encouragement I needed to hear. I nodded and smiled wide as she went about comparing the anal beads to the dildo, the first rung of the toy being roughly the size of a sphere before getting larger and larger.
“See, about the same size,” I added.
“Are you blind?” She was right of course, as even the first bubble of the dildo was bigger than the bead…which was bigger than my thumb. “Og, what are you doing to me.”
“Here, I’ll put on the lube,” I suggested, already smearing the toy before rubbing a healthy dollop over her backdoor. “And you try with the dildo. You have complete control.”
“Well I guess I could try at least,” Cara said. “But there is no way I can fit all that in this ass.”
“One way to find out,” I said.
Cara was already set back up on her hands and knees with her chest resting on the bed and her booty way up in the air. I loved the fact that her asshole glistened as the sunlight hit the copious amounts of lube on its surface and she looked so sexy naked except for a pair of thigh-high socks.
“Okay…okay,” she said as she placed the rounded tip against the crinkled surface. “Just gonna go nice and slow.”
She started pushing as I could see her forearm tense before transfixing back on her ass. Sure enough, the anal beads had loosened her up as it was only after seconds before her hole spread and the first bubble of the dildo disappeared inside her ass. To my shock, she didn’t just hold it in but instead slowly fucked her own ass with the initial tip of the toy.
She was a smart girl and understood that momentum meant a lot so she kept the toy sawing slowly in and out. I was so hard and found my hand stroking my cock as her asshole constantly widened and shrank until she got to the tapered end of the first bubble. Without breaking stride she tensed her forearm again and pushed until the second part disappeared in her ass as well.
“God! Uhhhh,” Cara screamed as she had over 2 inches of a thick toy buried in her virgin asshole.
“You’re doing amazing,” I said as my free hand closed over the dildo. “Let me take it from here.”
The model had no issue giving up control as she released the toy into my stead and I immediately continued her good work. Pushing with steady force I didn’t relent until a third bubble pushed into her behind which was met with louder cries, but none were of pain. But as soon as it was in, she reached back and took control, apparently only needing me to get over that last bump.
I didn’t mind as I watch while she fucked herself with the new thicker inch in her ass. The English model was nothing short of a mystery and I was stuck happily in her web, waiting to see what was next. With a firm grip she pulled the third bubble out, then the second before completely removing the toy and I saw her asshole seal as tight as if nothing had ever been permitted inside.
“My bum still pretty,” the model-turned-actress asked with a confident smile.
“Oh yes,” I replied as she thrust the toy back in, easier than ever.
First one bubble then a second went inside without issue before backing out the toy completely once more. Apparently with new found anal confidence, Cara fucked herself with the first two rungs before building speed and thrusting the third level inside next. I was transfixed as I watched the skinny model fuck herself faster and faster while my hand rubbed my own dick with increasing speed.
“Oh my God,” Cara screamed as she pulled the glass dildo from her ass. “How far down did I go?”
“Right here,” I said, pointing to the spot.
Her face was of pure elation as her thumb moved along the groove of the third and fourth bubble. Without hesitation she stuck out her tongue and licked the portion of the toy that had been wedged in her own ass, starting at the third bubble and going to the top. At this point she opened up wide and sucked clean the first portion of the toy for a few bobs before lowering herself further and doing the same to the dirty second and third parts as well.
“I got one more thing for you,” I told the model.
“What’s that,” she asked with a knowing smile.
“Undo my pants and I’ll show you,” I replied as we stared deep into each other’s eyes.
“You gonna be good to me,” Cara asked, that smile never faltering for a moment.
* * *
Kristen Stewart actually did have a meeting but it wasn’t for a studio but rather a monthly meeting with her agent. It was a fluid thing that could have been anytime, but the redhead wanted to make herself scarce as Og did his thing with her girlfriend. It irked her that she needed to use the man to get Cara to do something sexually, but if it meant getting to peg the gorgeous model then she was willing to swallow her pride and arrange the deal.
Her meeting with her agent lasted roughly an hour, which meant she had several more to kill before showing back up at Og’s apartment. She didn’t know if the handsome man would call or text when they were all finished up so she planned on just going back around 4pm. Bored, the fiery redhead pulled out her cellphone and dialled a familiar number.
“Hi sugar tits,” Kristen spoke into her phone.
“Back at you sweet ass,” Anna Kendrick replied with a giggle. “What’s up.”
“Nothing, just chillin as the kids say,” the redhead replied.
“Chillin huh? Or freaking out as my boyfriend sodomizes your girlfriend while she screams out his name,” the Pitch Perfect star got to the point.
“Bitch,” Kristen swore. “Maybe we gave him too much credit and Cara will call any second in tears, saying what a jerk Og is.”
“I’d take that bet,” Anna retorted.
“Yeah…I know.”
* * *
I decided against jumping straight into pummelling the girl’s virgin asshole. Even though she had exceeded expectation with the toys, I could still sense some nervous energy from the blonde so I went to something she was more comfortable with.
“You yes Og…lick that pussy,” Cara moaned as my tongue swiped up and down her bald cunt.
Of course I didn’t leave her bum alone for very long. Breaking briefly to suck on my middle finger, my mouth immediately went back to her pussy while the digit pushed against her sphincter. After being used for the past 30 minutes, she was relaxed enough to let my finger glide right in and I built on that momentum, fucking her fast as my lips latched to the top of her box and my tongue darted at her clit.
Since Cara’s ass had no trouble eating up my first, I decided it was time to add a second. Her screams died down as I stopped my oral assault on her clit, but her moans took on a new sound as I pressed the new wettened digit with the first and wiggled into her virgin butthole. It was tight and I couldn’t fuck her as freely, but it was still progress.
“Mhmmm…yeah,” the Suicide Squad moaned, her own finger taking over clit-rubbing duties from me.
With Cara laying on her back, I had her use her hands to pull apart her cheeks so that I could get faster in finger-fucking her tiny ass. Of course after a minute or two of this a pulled out and replaced the digits with my tongue, able to reach as far into her dirtroad as I could. Of course the model reacted so loudly I feared my neighbors would complain, but I was rimming a gorgeous Victoria Secret model so I could care less.
I kept munching at her adorable butthole while my hands worked furiously to rid myself of the jeans I wore. When it came time to remove my shirt, which required me to pull my tongue away from her asshole for the first time in minutes, I was pleased to see that the actress was using her own fingers to alternate between rubbing over the rosebud and actually fingering her own ass.
“You want it? You want this small ass,” she asked, dipping inside the tight hole. “Finish losing the clothes and get on your back.”
As Cara moved over on the bed so that I could lie down when naked, I saw her pick her head up when she was sure I was stripped bare. She soaked in my naked form but her eyes came to rest on my thick, 9-inch pole. She was actually bisexual since she’d been with men in the past, but not for awhile so seeing my monster made her eyes bulge in nervous excitement.
I climbed atop of the soft bed and laid down facing the ceiling in the middle with my head nestled in the pillows. Cara didn’t give me a chance to settle as she already had her leg swung over my powerful torso with her hips dangling over my lap. Descending slowly, the second she felt my unsheathed penis brush her folds, she sank down further on her knees and popped me into her pussy.
“Fucking hell you’re tight,” I grunted as she enveloped the first several inches of my cock into her velvet-feeling hole.
I didn’t know how long she and Kristen had been together, or more importantly when the last cock she took was but judging from how tight she was, I was willing to bet it wasn’t for a long time. It was a good thing I went down on her earlier and got her good and wet or else there was no chance I could fuck her this quickly.
“Thanks,” she muttered as she took the rest of his massive dick into her pink hole. “Damn that feels so good.”
Smiling, I sat back and allowed the sexy model to do the work above me. Her pace, which had started slow, had picked up considerably. Raising quickly before slamming herself down into my lap, the horny girl was doing her best to get off quickly so that I could have my way with her anyway I saw fit.
“Oh shit…fuck…yes, yes, yes,” Cara shouted, her orgasm building. “Make me cum and you can put it anywhere.”
“Anywhere,” I asked knowingly.
“Fine! I’ll spell it out for you Og. Give me my orgasm and you can shove that fat cock in my tight, virgin asshole. That clear enough for you,” she asked.
I had my doubts at the onset of Kristen’s challenge to me earlier in the day but hearing the model state that promise so clearly gave me crystal clear focus. All I could now think about was giving Cara the orgasm she so badly wanted so that I could fulfill my own (and Kristen’s) deviant fantasy.
With her still sitting in my lap bouncing along the entire length, Cara freed my hand from clutching her breast and brought it towards her face. Opening her mouth, she isolated one of my fingers and moved it into her mouth, simulating a blowjob in order to get my middle finger coated in her spit. Once sure it was sufficiently wet, the horny actress guided it down and around her body until it was resting on her curvy ass.
I instantly knew what she was playing at but wanted to give her some control, making her essentially beg to get her booty played with. I took over from there and placed the wet digit on her constricted asshole, rubbing it around but never penetrating, not this time.
“Once I cum you can do more then rub your finger,” she whispered into my ear, thudding her ass continuously into my thighs.
“Then I should make that happen,” I replied with a cocky smile.
No longer holding anything back, I pushed my hips forward so that they crashed into Cara as she was descending on my tool. The collision made a loud wet slap as flesh crashed against flesh but it achieved penetration deeper than the model had experienced.
“Fuck…I’m so close,” Cara screamed. “Keep fucking my tight like twat!”
I knew that she was a woman who liked her ass played with so I slid the wet finger into her backdoor the next time she plummeted in my lap. Cara squirmed at first, but she was so lost in her own pleasure that she barely noticed after the initial penetration. Seeing that she hadn’t had her screaming orgasm just yet, I pushed a second digit inside her asshole so that both of her holes were being stretched and probed.
“OHHHH….YESSSSS,” Cara shouted at the top of her lungs as she gushed her juices onto my fat dick.
Losing control of her bodily function for a moment after her intense orgasm, the sexy model collapsed down onto my chest so her perky tits pressed against me. Stroking her hair, I let the leggy star recover rather than push her into more sex, especially when at the beginning of the day she made anal sex a clear no.
“That was hot Cara,” I complimented from beneath her.
“Mmhmm,” she agreed. “So how do you want me?”
“I think you’ll do best with doggy,” I replied.
I felt the model take a few more breaths atop of me before she pressed herself up while swinging her leg off of me in the process. Like the position she was in during feeding her own ass the dildo from earlier, Cara got onto hands and knees with her head up by the head board. In one smooth movement I was on my feet, bottle of lube in hand and smearing both my dick and her virgin asshole.
“Mmmm,” she moaned in response to the cool, wet touch.
“You ready,” I asked, kneeling behind her, tip already brushing her rosebud.
“Just be nice to it,” she pleaded.
I nodded then took a breath to steady myself. Never in my wildest dreams did I ever think that I’d be taking Cara Delevingne’s anal virginity. Then again until last year I didn’t think I’d be dating Anna Kendrick, or have fucked Alison Brie or had a threesome with Kristen Stewart. I was either the luckiest mother fucker in the world or I had a sexual guardian angel looking out for me.
“AAWWWHHH YEESSSSSS,” Cara screamed as my head popped into her.
“It feels so small,” I groaned from above her.
“I can take it,” the model insisted. “Just slide that wet dick in my ass.”
“It’s so fucking tight,” she swore in agreeance.
I would only find out later as we talked about her experience that Cara wasn’t consumed in pain like she expected or like so many girls had during anal sex. We had done a thorough job stretching out her elastic hole so that even though it didn’t feel great, it was only some minor discomfort as I first stretched her asshole around my giant cock.
I normally would have started a lot slower but just from reading her body language I knew the leggy lingerie model was ready for more. Not stopping at the tip, I slid more of my lubed up cock until I sensed her tighten up. I sat still for a moment and looked down to find that more than half my length was in her ass!
“Good girl…taking that cock so well,” I congratulated as I began pulling my hips back.
Now knowing where her limit was, I stayed within it, constantly pushing in and out only half my length. I didn’t go very fast but now wasn’t the time for speed, it was the portion that she got comfortable with anal sex. Deciding she was ready for more, I grabbed her wrist and placed it between her legs and let her instincts take over.
Like I expected, the lesbian began to rub her clit and the rest of her folds and I could feel the shift in her muscles. More relaxed, I opted for pace rather than trying to cram inside deeper and was rewarded for my decision. Even though it was only 5 inches in her butt, I was plowing her just as fast as I had done to her pussy minutes earlier.
“You like fucking my little ass,” she asked him. “Working that fat cock in my ass?”
“You fucking bet I do,” I answered. “And you’re doing so good. I’m already halfway in.”
“I can take more. Give it all to me Og,” Cara demanded greedily. “Stuff your whole cock in my small ass!”
Delighted to hear that she was so into the anal sex, I slowed my pace to about half speed but started probing deeper. After every inch or so I would speed up and stay at that depth for awhile before plunging down again. Finally deciding now was the right time, I gave Cara what she wanted and pushed the rest of my shaft into her until hips slammed against her curvy ass cheeks.
“Oh shit,” she groaned in a combination of pain and pleasure as I stayed balls deep in her tiny hole.
“You okay Cara,” he asked after hearing her sharp yelp.
“I’m good. I can take it,” she told him confidently.
I would have stopped if she wanted, but I was over the moon that she didn’t ask that. Unhurriedly, I pulled most of my shaft from her bowels before slowly working it back in. My hips touched her ass cheeks at a much lower speed then the last time I fully entered her ass, much to her liking.
“You like having a cock worked into your asshole,” I asked, engaging her in the dirty talk she started.
“Yeah I do. I’d like it more if you took the training wheels off and really gave me a ride,” she replied, catching me by surprise.
Pulling out almost completely, I crashed my hips against her ass, causing it to ripple. It drew a sharp scream from her again, but when she looked back at me, her glance told not to stop fucking her. Listening to her silent instructions, I did the same thing and smiled with glee as my dick disappeared within her asshole.
I was finding my stride now and I wasn’t looking back or stopping for anything. I just seemed to tune everything out, including the burning feeling in my balls as it just felt like I could sodomize this skinny model all day and night. I slapped her ass, first the left cheek then the right all while looking down and watching as my entire dick would disappear then reappear every second or less.
“Such a dirty slut. Only sluts take it in the bum,” I told her, demeaning her further.
“Then I guess I’m a filthy anal whore,” she replied. “Now really fuck this big slut in her tight ass!”
“It won’t be this tight ever again, not after I’m done with it tonight,” I told her while slamming into her asshole again at a quicker speed.
“Yes! That’s it! Fuck that ass! You know I fucking love it,” Cara continued her encouragement.
Even with my cock gliding smoothly in and out of her ass, I was content. Giving her cheeks a firm squeeze, I pulled back my right hand and let it come crashing down onto her backside. Instantly her creamy white skin started to turn red and she let out another yelp of pain mixed with pleasure.
“That cock feels so good in my ass,” Cara told me while continuing to rub her sensitive clit with her finger.
“Good…because that’s a lot of dick up your ass,” he replied. “Now I want you to taste it. Suck your own ass Cara. Be a good ass slut.”
Without needing another prompt, Cara spun around when she felt I withdrew from her ass. It felt weird to not have my dick filling up her rectum, and I felt that she was probably feeling empty and missing it as well. Grabbing my cock at the base, Cara shoved the first half into her mouth and started to noisily suck on my offering. It was the third time that night she licked something that had been lodged deep in her bowels, and for a third time, she liked the taste.
“Yes. Taste that dick with your ass all over it,” I demanded. “Suck your own ass!”
She did as I asked by giving me the sloppiest and probably loudest blowjob I could have imagined. She was not in Anna’s league, no one was actually with her ability and preference to deepthroat my cock, but Cara was thorough. Only able to bob on half my length at most, she emitted loud gurgling noise with more spit decorating my dick each time she bobbed downward.
“How about we get this cock back in my ass,” the sexy model said as she pulled her mouth from my manhood.
“Thought you’d never ask,” I replied with a wide grin. “But I want you to ride it this time.”
“You want me to fuck my ass then I’ll ride the shit out of your dick with my tight little ass.”
Crawling upward on the bed, Cara hovered above me for the second time this night. This time, as she lowered herself, she took the cock towards her further back hole rather than her pink one she had done earlier. With me pressing against her puckered bum, she sank down on her knees further until I re-entered her butt.
“Such a tight ass,” I commented as I slid back inside. “Come on Cara. Fuck your own ass.”
“Oh I’m going to fuck it so good you’ll be cumming in no time,” she retorted as she started to rise and descend on my entire length. “Fuck! Right there.”
With each pass into her rectum Cara seemed to gain speed until she was a blur atop of me. I had no idea how she could bounce so quickly, especially since we had been having sex for quite some time already but she showed no hint of fatigue. Her body was covered in a layer of sweat that made her creamy skin glisten in the sunlight.
Normally I wasn’t such an animalistic lover, in fact with Anna I was a lot more tender but for whatever reason Cara Delevingne was bringing out the savage in me. Not content to have her do all the work I was viciously pumping my cock up into the first-time anal lover, driving into her ass deeper and faster than either of us thought possible.
“God you are taking this in your asshole so fucking well,” I commented without skipping a beat.
“Holy shit I think I’m cumming,” Cara screamed as she continuously rode my massive cock.
I was completely flabbergasted and said the first thing that came to my mind. “No. Only huge anal sluts can cum with a cock in their ass,” I teased.
“Then I’m a giant slut because I’m so close,” she warned, not picking up my tone of joking. “Ohhhhhh….yesssss!”
“Would it help if I slapped your ass again,” I asked before smacking her slim yet perfectly shaped cheek.
“Yeah…Ughhhh….getting close,” she moaned. “It might help if you pulled my hair too.”
Loving the fact that Cara was getting off by being disgraced like a common whore, I kept slamming my dick into her ass. Still slapping her ass, I reached up, twisted my hand in her wild hair and wanked it downward as hard as I could. It was something I never would have even thought to do with the more fragile Anna, but with Cara she was urging me on.
“Ahhhh. Oh my fucking God! Awwwhhh,” she grunted in pure elation. “Ughhhhh. I’m cummingggggg! I’m fucking cumming! Don’t stop fucking my ass!”
I was happy she came when she did because I was in desperate need of release as well. I let her ride out her orgasm, which she did but sitting deep in my lap and grinding against me, my manhood as far into her bowels as it could go. Her screams were ear piercing but thoroughly deserved, surprising herself by cumming from anal sex.
Once I was sure she had cum and was done, I pulled her off of my lap and let her fall onto her back. Climbing atop of her so that I was straddling her small but perky chest, I stroked once or twice until the familiar feeling of cum starting to migrate from my balls overtook me. Knowing that the last act of degradation would be to cum all over the model’s perfect face, I took aim and waited.
“Cover me,” she said through exhaustion but still upbeat. “Cover my fucking nasty face.”
“Oh shit,” I shouted before doing just that.
Like most girls, Anna wasn’t the biggest fan of taking a cumshot to the face so since they were rare I kept my eyes open this time as I climaxed. I watched as the the first rope of cum propelled itself and streaked across Cara’s nose all the way up to the forehead. The second streak hit the same target then I decided to paint another area of her pretty face. This time I splattered into her closed left eye while the fourth jet hit the side of her head and nestled into her dyed blonde hair. The last remaining squirts didn’t have the same quantity as the earlier ones, but there was still enough left to coat the rest of her face.
“Oh my God,” I cursed.
“Glad you enjoyed yourself big boy,” she told him before sucking on his sensitive tip, tasting herself for a final time.
“Tissue or the bathroom and shower are straight through there,” I offered.
“With this much cum I’d better go shower if you don’t mind,” Cara answered before disappearing into the on-suite washroom.
Once I heard the water of the shower turn on, I pulled out my cell phone from my discarded pants and dialed up Kristen’s mobile. I figured it would be on silent if she was still in her meeting but after it rang once it was immediately answered.
“It’s done,” I told the redhead. “And might I add you got a real dirty one on your hands.”
“Yeah? How’d she do,” Kristen asked.
“Well, at one point she demanded I bend her over and fuck my ass like a dirty whore,” I said, giving her girlfriend the direct quote.
“Thanks…I guess. Be there shortly,” Kristen answered before hanging up.
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Dating Anna Kendrick