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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
- 5
- 6
Summary: Still feeling guilty about hiding her threesome with Blake Lively from Og, Anna Kendrick makes it up to her boyfriend by hooking him up with Taylor Swift.

“How was therapy, babe?” I asked as Anna Kendrick came into my apartment, giving a brief rap of the door before entering.
“Oh, you know, she didn’t have to use shock therapy yet so I’m not so fucked up that I can’t be helped,” Anna said, offering a weak smile as she threw herself down on the sofa opposite me.
“Seriously though, you okay?” I asked, noting her unusual worn-out body language.
“Can I tell you something? You can get mad if you want, but my therapist says holding it in isn’t helping and…” Anna said, starting to do her typical stammering as she got awkward. Though she continued to spew words, I more or less drowned them out, worried what I was about to hear.
“Anna...it’ll be okay. Just tell me what’s bothering you,” I said when she was done.
“Okay well, you know how early last year I was away in Toronto shooting a movie,” Anna started, continuing after I nodded my head, knowing she was referring to A Simple Favor. “Well, I sort of, kind of, fucked Blake Lively. Like, a lot.”
“Anna, why would I be upset about that?” I asked, sitting up and stroking her leg.
Though Anna looked all cute and cuddly, the girl was a straight up sex demon. It seemed that no matter how much or how regular we fucked, her appetite was just barely quenched. Don’t get me wrong, I’m not complaining. In fact, I think every guy (and probably girl though I’m only going with my personal experience) would love the fact their girlfriend was constantly horny, especially if their girlfriend was Anna fricking Kendrick.
Therefore, when we first started dating almost 2 years ago, it was a casual affair. I had learnt through conversation that she didn’t like being tied down, which I was willing to forego if it meant getting to fuck and be with her as one of her steady partners. However, after 6 months of casually dating, she came to me and more or less asked to be exclusive. Well, her version of exclusive. Which meant we could both still fuck as many girls as we wanted provided we were willing to share and we always came home to each other. It was a deal I was more than happy to make, but in the back of my mind I knew that Anna was unlikely to ever totally be tied down.
“So while most of the time it was only me and Blake fucking, one time it was with her husband as well,” Anna finally shared.
Even as she spoke the words I could see some of the weight that had been on her chest start to lessen. She had her head down but I could see her piercing blue eyes looking out the side, watching me for any reaction. While I wasn’t super happy about her sleeping with another guy, I would have also have been a big hypocrite to be pissed about it. If anything, I was a little peeved that she felt like she had to keep it from me. However, seeing how tormented she was by keeping this from me, as well as fucking another man while we were together albeit not super exclusive, made it so that the last thing I wanted to do was twist the screw.
“Anna...we’re only human. We fuck up, we make mistakes. All we can do is find someone we want to be in the foxhole with.” I explained.
I was going to say more but seeing the wave of relief wash over the normally reserved woman was enough for me. I got up and went to confront, a gesture she was more than happy to have from me. As I held her in my arms, she added a few extra details since I handled the big bombshell so well, the most notable of which was the fact that Ryan and Blake had taped the threesome, with Anna’s consent of course. Off hand she asked if I wanted her to get a copy of it and I found that I did want to see it, so she said she’d contact Blake soon.
BUZZ BUZZ BUZZ
“What’s that for?” I asked as Anna went to pull her phone out.
“Alarm. Meeting Aubrey to get ready for tonight.” Anna explained. “You still want to go to the party with me?”
“I want nothing else.”
*   *   *
“Listen, you keep hanging out here and I’m going to go grab us some drinks,” Anna said.
I nodded and watched as my stunning girlfriend in her tight-fitting costume sauntered her way to the bar. I’m happy she offered to go because being an adorable female, not to mention a celebrity, meant she would skyrocket to the front of the line, whereas I’d have waited for half an hour. However, I noticed that her course was taking her to an out-of-the-way part of the counter, closer to the VIP, meaning the tiny actress had to wade through more bodies.
I watched in curiosity now and soon realized that her course was bringing her to a collision course with the tall, radiant blonde that was demanding a lot of attention. I swore under my breath as I realized that Anna had cozied up on the bar to Taylor Swift! I know they weren’t friends, as they ran in different circles, but within seconds the two were exchanging words. In fact, by the sentence it seemed that Anna and the girl dressed as Wonder Woman were becoming more engrossed in the conversation.
After maybe another minute, the barkeep came over and took their orders. Anna and Taylor chatted for the 30 seconds it took for their drinks to be brought, at which point the tiny auburn-haired actress and leggy blonde singer said their good-byes. With a final greeting, Anna scooped up what appeared to be two whiskey sours and headed back my way.
“Why are you smiling so brightly,” I asked as Anna came back towards me, beaming. “Taylor ask you to become one of her girl squad?”
“No you dummy,” Anna said, giggling at my joke. “I’m smiling because tonight you are totally gonna fuck that goddess.”
“Wait!? What!?” I was actually I was able to get out any words.
“Not a guarantee but, I mean, she’s as close to a for sure lay after our convo,” Anna added before recapping their brief but apparently productive conversation.
*   *   *
“Oh my God, I love your costume,” Anna said. She had arrived at the bar and slowly inched her way over until she was right next to Taylor Swift. “I guess it helps having those legs to pull off the tiny booty shorts.”
“Thanks...oh! You’re Anna Kendrick! I loved you in...everything!” Taylor said, reaching down and giving the girl near crushing hug.
“You’re so sweet,” Anna said before using the line that would shift the conversation to where she wanted it to go. “Too bad you can’t use that line on C-Diddy.”
“You know Cara?” Taylor asked, referring to one of her best friends Cara Delevingne.
“Yeah. She dated my bestie Kristen Stewart for awhile. My boyfriend even took her anal v-card,” Anna said with a little laugh.
“Oh my God!” Taylor nearly snorted out her drink. “I remember Cara telling me about how some guy totally turned her into an anal loving whore. Her words.”
“Yup. That’s my guy...well not exactly just my guy,” Anna said, continuing to lay her trap for the 29 year old singer.
“You mean you aren’t dating anymore?” Taylor asked, unable to keep the note of curiosity from her tone.
“You’re dating. In fact he’s here tonight. It’s only that we aren’t exclusive. Great guy and all, and magic cock for sure, but we prefer an open relationship,” Anna described, bending the truth a little.
“Interesting. Very interesting,” Taylor replied, pondering.
“And another crazy thing about him...his cum.” Anna stated, baiting the hook further.
“What do you mean,” Taylor asked.
“Tasty. Not in a way that is unnatural or anything but even for girls with super-sensitive taste buds, his cum is at worst neutral tasting,” Anna shared. This was the truth, which was one of the reasons why Anna had him finish in her mouth so often. Less clean up and a yummy little treat.
“That is wild.” Taylor said, smile plastered on her face.
“Anyway, I should bring him his drink,” Anna said, picking up the two whiskey drinks.
“Why don’t you come join me and the squad in the VIP? I’ll tell the bouncer to admit the tiniest archaeologist and a guy with her that has a magic cock,” Taylor offered, bring a laugh from both women.
“See you soon.”
*   *   *
The rest of the night passed in a blur for me. After Anna had caught me up on everything about her conversation with Taylor, she added the fact that Taylor was currently in between boyfriends. I took that to mean she was available, but Anna went on to explain that when Taylor was dating someone, she was super loyal. However, when single like she was now, Taylor would sleep around, or as Cara Delevingne described, Taylor would totally whore out.
We went up to the VIP and hung out the rest of the night with gorgeous people and A list celebrities. It was surreal, even for someone like myself who was used to rubbing elbows with Anna Kendrick and some of her friends. However, there was just something larger than life about Taylor Swift, so I found myself getting nervous just with the idea that I could fuck her tonight.
“Just remember not to put her on a pedestal,” Anna reminded me as the night was winding down.
“I don’t think that’s a worry. She already left,” I replied, noting the lack of tall, gorgeous, blonde singers around.
“I wouldn’t be so sure about that,” Anna replied, seeing a large man in a suit headed my way.
“You Og?” the man’s deep, booming voice asked.
“Yeah,” I replied nervously.
“Ms. Swift has left a car for you to attend her at her house,” the man said.
“Told ya.” Anna said with a smile. “Now go have fun. And remember, I want every last detail.”
*   *   *
Og wouldn’t have traded Anna in for anyone, therefore he was more than happy with their arrangement for tonight. He loved Anna’s mixture of cuteness, quirkiness, personality, atypical beauty and, of course, her amazing rack. That being said, Taylor Swift was something else entirely.
Part of it had to do with her aura, how she had become larger than life while also picking up a well deserved reputation for having a healthy appreciation for sex. Not to Anna’s hardcore degree, but Taylor was known for hopping to bed to bed for a good reason. Of course, she had an amazing body to back up her sex positive attitude and worldwide reputation.
Taylor’s body had changed a lot in the last couple of years. The constant touring meant she found working out to be more paramount, and you could tell the gym work paid off. The barbell had completely blasted her glutes, added inches to her thighs in all the best ways and flattened her stomach. Combined with that, Anna had shared that her bra size had grow almost a couple to be a full B cup. Those changes were magnified by the fact she also showed a willingness to show off her amazing body more and more, whether it be in super skimpy costumes or bikini pictures on social media.
“I was beginning to wonder if you were coming or not,” Taylor said when she opened the door for me.
“Sorry about that,” I apologized though traffic was out of my control. “Great place though.”
“Thank you,” she replied, though I got the distinct impression she was sizing me up. “Can I get you a drink? You’re a whiskey man if I remember Anna correctly.”
“Good listening. I am indeed. Neat or on the rocks. I’m flexible,” I replied, knowing that if anyone was likely to have good calibre alcohol, it would be Taylor.
Taylor turned and started walking down the hallway to her right. I got the impression I should follow so I did just that. Given the way she was swaying her hips, it was clear to me she was doing that on purpose for my benefit, which I appreciated it. This was more or less confirmed when she turned her head back to look at me and gave me a toothy grin, having caught me looking at her ass.
“See something you liked,” Taylor asked in a soft, seductive tone as we entered her kitchen.
“Sorry. That was not cool of me to be checking you out like that,” I confessed.
“Nothing wrong with looking,” Taylor said as she quickly got down two glasses and filled them rather generously with whiskey.
“Cheers,” I said, raising my glass to clink with hers.
“Cheers,” she replied, touching glasses then both of us took our first sip. “So you’re an ass guy?”
“Tone of surprise?” I shot back with my own question.
“Just surprised is all,” Taylor answered. “You’re seeing Anna Kendrick for a long time now. She’s got a cute butt but her tits are obviously the showstopper on that pint-sized hottie.”
“Totally fair assessment. I think her legs are a little underrated as well,” I added, still in disbelief that I was in Taylor Swift’s kitchen for a nightcap. Remembering Anna’s words from earlier, I took another sip and tried to drown my nerves. “But yes, though Anna has tempted me with her great boobs, especially for a spinner like her, my first love has always been booties.”
“We all have our preferences,” she said with a naughty twinkle in her eye. “So how does mine stack up?”
“Your butt? Well, maybe its the whiskey talking or your straight forward approach but I’d say it receives top marks,” I replied honestly. When I saw the pleased but eager for more look on her face, I continued my assessment. “I remembered it being...smaller before from pictures but seeing it tonight...wow!”
“Oh?” Taylor asked, downing the last of her drink and starting to walk around the counter to be in front of me.
“I mean, it seems like everything on you has filled out in the best way possible. Your hips look wider to give that perfect hourglass figure. Your legs have always been a traffic stopper but now they seem thicker, more muscular and yet so feminine and sexy. Your aforementioned caboose changed from small and cute to big and tight. More muscular like your thighs.” I replied, knowing for sure it was the alcohol making my lips so loose.
“Wow! That was super descriptive.” Taylor laughed as she stood right in front of me. “A girl might get the impression you found her attractive.”
“Good...because that was the exact impression I was trying to give off.” I retorted, matching her playful banter like for like.
I saw my opening so I went for it. Reaching an arm around her tall frame so my hand could land on the back of her head in the soft curls of blonde hair, I simultaneously pulled her towards me while I leaned forward. Our lips touched with a soft smacking sound at first before we both opened our mouths and pressed our tongues against each others. The softness ended their as we greedily pressed our lips together while our tongues battled one another for supremacy.
As much as I wanted to continue the intense makeout session going with the gorgeous leggy singer, after another minute of kissing I broke it off. As good as it felt to tongue wrestle with Taylor, I had much more fun ways of spending the night with her. Standing up I put my hands on Taylor’s waist. Leaning her back against the counter I bent my knees and pressed my body against hers.
“Bedroom,” Taylor said, breaking the kiss to wave her hand in the direction of where another hallway exited the kitchen.
“Sure,” I said, lifting her up and setting her down on the counter instead.
Putting my hands on her knees I pushed them apart so I could slip between them. Leaning in to kiss the pop singer, I slid my hands up her thighs which were soft and unending until they disappeared underneath her dress. As they moved closer to her sex, Taylor spread her legs even wider to grant me more access and pressed her chest against mine.
When my hands reached the tops of Taylor’s thighs I extended my thumbs and rubbed them against the front of her panties, just above her snatch. Hooking my middle fingers in the waistband of her thong, I slowly tugged them down. Wrapping her arms around my neck, Taylor used me to help lift herself up so I could pull her panties down over her ass. If I thought she had long thighs then I was in for a treat as the thong just kept sliding down and down. Finally the tiny undergarments crested her slim calves and went over her feet, still contained in her black high heels.
“God, you’re unbelievable,” I grunted as my hands rubbed up her lengthy and smooth legs.
Standing there with her panties in my hand, I looked at Taylor with what could only be described as an evil grin. She cocked her head to the side in question, wondering what my thought process was. We both knew that from the position of a pantie-less woman sitting on a high counter with legs spread, there were a lot of possibilities. Knowing I couldn’t just stand there and smiling down at her like an idiot, only one option came to me that I knew I had to do first.
Stepping up to Taylor, I gave her a quick kiss before sinking to my knees. She moaned as I put my hands behind the backs of her knees and pulled her forward until her ass was right at the edge of the counter. Draping her flawless legs over my shoulders, I flipped the skirt of her dress up, exposing her bare pussy to my hungry gaze. I didn’t know what to expect I’d find with Taylor Swift’s pussy but I was pleased that it was shaven bald, meanwhile her pussy lips were bright pink, already glistening faintly in arousal and just looking the prettiest little snatch I’d ever seen.
“So fucking hot,” I breathed as I drank in the sight.
Once more, I remembered Anna’s warning to me of not being to awed by the mega pop star and her celebrity fame. Therefore, I decided a little teasing would be perfect and set me apart from her many other suitors. Therefore, reaching under her to grab hold of her thighs, I lightly blew a stream of air across her pussy. Taylor moaned before making a motion to grab the top of my head in response. As she tried to pull my head closer to her wanting sex, I stiffened my neck and refused to budge as I exhaled against her pussy again.
“Please?” Taylor groaned, grabbing a handful of hair to pull me closer.
I don’t know why it felt so good to make such a massive celebrity and known sex fiend like Taylor Swift beg for me to eat her out, but that didn’t change the fact that it felt pretty damn good. Therefore I finally relented by leaning in and ever so lightly ran the tip of my tongue along the length of her slit. I was pretty sure that it wasn’t what she was looking for though because she let an anguished grunt at my teasing.
“Want me to lick you?” I asked, looking up at her.
“Yes please,” Taylor begged, using her powerful legs on my shoulders and her hands in my hair to try to lift herself off the counter and get her pussy a couple inches closer to my tongue.
“Tell me what you want,” I said, using my hands on her thighs to hold her down on the counter.
“I want you to lick my pussyyyyyyyy,” Taylor moaned, her body twitching as I finally let my tongue dart out to flick at her clit.
I decided that actually making Taylor Swift beg me to eat her out was enough for me to stop delaying. Done teasing, I moved a hand between her legs to spread her pink lips with my fingers so my tongue could lightly pummel her clit with rapid but soft bats. When she started to gasp for air and her fingers in my hair threatened to rip it out at the roots, I changed tactics by moving my tongue down to slither through her folds, collecting moisture.
“Ohhhh, fuck me,” Taylor gasped, her grip on my hair tightening as she bucked her hips against my face.
Hearing the notorious good girl Taylor Swift swore kind of spun me for a loop but I quickly recovered. Moving back up to her clit, I wrapped my lips around her sensitive nub. When I gave it a suck, Taylor stiffened like she’d been shot, her hand in my hair twitching hard enough that it felt like she could’ve pulled out a whole chunk of hair.
Keeping one hand on her thigh to keep her from bucking me off, I moved the other one up to where she was trying to scalp me. I groped around until I could find and grab her hand, at which point I was able to pry her fingers loose from my hair. Giving my genetics I was unlikely to keep it all forever so I wanted to maintain it for as long as I could, though if there was a reason to lose some then Taylor Swift ripping it out while I eat out her pretty pussy would be a good reason. As her hand wrapped around mine instead I brought it to her flat stomach where I lightly pushed, urging her to lay back.
“Please keep going,” Taylor begged once more.
As if we reached a compromise, as the popstar leaned back her hands went back to my hair but the grip stayed loose enough for me to deal with. Of course, with her back against the counter it gave her leverage to buck her hips, which made it more difficult to hang on. Rather than continue to suck on her clit, I changed again and flattened my tongue against it. Bringing my right hand down between her legs, I circled the slick opening with my index finger for a few rounds before slowly pushing my digit into Taylor’s tight cunt.
“Ohhhh,” Taylor moaned, her body jerking involuntarily as I kept her on edge.
Sensing that I had megastar Taylor Swift on the ropes, close to having her cum, I went in for the kill. Holding her as still so I could use my tongue to flick at her clit once more, this time in a frenzied, rapid-fire fashion, all while my finger continued plunging the depths of her snatch. However, I figured the slender singer could do with extra thickness filling her so I added a second finger to the one in her pussy and started to pump them in and out of her.
“Oh God! Fuck, fuck,” Taylor hissed, her thighs clamping tightly against my ears as her hips started to buck.
She had strong thighs so I hoped she wouldn’t use them to pop my head like a grape. Blocking that from my mind so I could focus all my attention on keeping track of her sensitive nub in all her bucking, I curled my fingers inside her snatch. Finding her G-spot with expert ease, I stroked it with my fingertips and was rewarded with a loud scream as her whole body tightened up. Knowing I had my range, I kept my fingertips in the same spot and rapidly brought them off and back onto the sensitive spot, tapping them repeatedly.
“JESUS CHRIST! I”M CUMMING,” the singer hollered at the top of her vocal range.
As my twin efforts of finger blasting her G-spot and flicking her clit with my tongue paid massive dividends, Taylor soaked my hand with her cum. Wanting her to stay at this bliss point for as long as possible, I kept flicking my tongue against her clit to prolong her pleasure, but as her orgasm wore on her dance training came to the forefront with her muscular thighs gripping my head tightly and with each twitch it felt like she was going to snap my neck.
Between the neck-breaking thigh squeeze and bucking her hips in tune with every one of my flicks to her clit, I relented my twin assaults on her snatch. Pulling my fingers from her pussy and, after one last flick, I unlatched my lips from the top of her cunt as I put my tongue back into her mouth. After a couple moments without stimulation, Taylor finally started to calm down enough to unlock her legs from around my head so I could regain my feet.
“Oh god,” Taylor gasped as her mental faculties started to return.
“Bedroom now?” I asked. The bedroom would be more comfortable but staying here would mean I could start fucking her as soon as I dropped my pants.
“Bed for sure,” Taylor said, sitting up. As she slid off the counter she had to lean against the edge for a moment until her knees stopped wobbling.
“Bedroom, it is then,” I said, reaching out and pulling the zipper down on her dress as I followed behind her. “That was going to need to go sooner or later, so I figured sooner was better.”
“I bet,” Taylor laughed.
Between her walking and me actively trying to pull it down, Taylor got tired of having to deal with it so stopped to let me pull it down her body and leave her in nothing but her bra. Though her tight-fitting dress left little of her body to the imagination, seeing her legs and ass in the flesh was a sensational sight. Her legs really did seem to go for miles, being a perfect mix of slender in the calves and thicker in the thighs, especially before they gave way to her underrated booty. Though not in the same category as a Jennifer Lopez, Taylor’s hard work in the gym had paid off in providing herself a nice juicy ass that was tight, firm and fairly thick for her thin frame.
“Now the bra,” I said.
Before I could reach out and try to unhook it, Taylor looked over her shoulder and gave me a sultry look that got across her passion level. With a naughty smile, the leggy singer took off down the hall, making me give chase, my eyes locked on her cute ass the whole way. As we reached the door to her bedroom I finally caught up to her by way of wrapping my arms around her, clutching her slender body to me, my cock pressing against her back through my pants. Lifting her off the ground, she screamed playfully as I carried her the rest of the way to the massive bed.
Still clutching her to me with my chest pressed against her back, I leaned forward until Taylor was laying on her stomach on the bed with me on top of her. Making sure her arms were pinned underneath her, I moved to straddle her waist so I was sitting on her butt, though I made sure to keep as much weight on my knees as I could instead of on her. I was far from fat, but even still I wasn’t looking to crush her, only playfully dominate the leggy blonde.
“That bra is coming off,” I said, dragging a finger along her spine as she squirmed under me.
Reaching her bra strap I deftly unhooked it with one hand while the other one set about unbuttoning my own shirt. When my shirt was undone I lifted up and rolled off of her. As she started to roll over, I grabbed a hold of her bra and pulled it down her arms, stripping the last stitch of clothing from her body long, curvy body.
“No fair, now I’m naked and you’ve still got all those clothes on,” Taylor observed.
“Then I guess we should do something about that,” I said as I took off my shirt.
“Definitely,” Taylor said, going for my belt.
Between the two of us we made short work of my clothes. When I tried to push her down onto her back though, Taylor merely smiled and slipped off the bed completely. Sinking to her knees she reached out and ran her fingertips along the shaft of my cock from tip to base and down further to my sack before wrapping her hand around the bottom of my manhood. Looking up to stare at me with her pretty green eyes, Taylor flashed me a grin before she lifted my cock until it was straight up and down. Leaning her head in, she blew a stream of air across the shaft, obviously trying to pay me back for teasing her earlier.
“Not funny,” I grunted as she smirked up at me.
“A little,” Taylor smiled before sticking out her tongue and licking the underside of my cock from base to crown.
“Better,” I said, leaning back on my hands as Taylor took the head of my cock into her mouth.
Unbelieving my luck that I could now say I’ve gotten a blowjob from both Anna Kendrick and Taylor Swift, I soaked in as much of this occasion as possible, especially since I knew Anna would want the full blow-by-blow. Swirling her tongue around the crown of my dick, Taylor slowly bobbed her head, taking a little bit more of me into her mouth at a time. When she had about half my cock in her mouth she stopped, took a breath, and reversed course until only the head was still between her lips.
“Much better,” I grunted as her tongue worked wonders on my knob.
Ignoring my comments, or maybe even inspired by them, Taylor started to push her head down but staying at the slow, sensual speed she initially started with. I didn’t mind whatsoever, in fact a slow suck from the popstar was probably preferred since it would mean my staying power would be all the better for it. When she got to the halfway point of my dick where she’d stopped last time, she kept on going, seemingly as if on a mission to take as much of me into her mouth as she could.
Feeling the head of my cock bump against the back of her throat, I thought that was it but instead Taylor kept pushing. Not surprising giving her vocal range, but Taylor tried and succeeded in relaxing her throat, thus allowing me to feel as my cock started to push even further into her mouth. Her adorable nose almost touched my pelvis but she started gagging so she used that as a cue to pull off me completely, a thick strand of saliva running from her lips to the tip of my cock.
“Glllkkk….ggaawwkkk,” Taylor sputtered.
Reaching down I brushed a lock of hair out of her face as her eyes watered, however Taylor was unaffected from her first try at deep throating me. In fact, as I stroked her cheek with my thumb and smiled at her, her hand started to beat my cock faster, using the generous amount of spit now coating it. She then stared back up at me and sucked hard, pulling the thick spit string right from my cock and into her mouth, a twinkle in her eye and a wicked grin on her lips.
Leaning back down, Taylor took me back into her mouth, but not before circling the tip of my cock with her lips and what could only be best described as making out with the head of my manhood with her eager tongue. This last a good few seconds before her face started to descend down into my lap, but this time when I bumped against the back of her throat, Taylor stopped and let her tongue caress the shaft as she worked her way back up.
“So good,” I mumbled as she expertly worked my cock.
The thickness of my dick was proving just a little too difficult for her throat to handle taking me all the way to the root, with her nose buried in my trimmed pubic patch and her chin touching my balls, but Anna had also struggle with that. Fortunately with Anna, she had enough practice at it now that my dick was a regular occupant of her gullet, and given the expert way Taylor was handling my manhood, I no doubt believed that with a little more regular fucking, she too would get to that level in no time flat.
Focusing back on the gorgeous blonde, Taylor was redoubling her efforts on her oral servicing of my manhood. The leggy singer cupped my sack and began to fondled my testicles as she increased the suction she was applying to my cock. The twin motions meant she gave up on her quest of choking down the entirety of my dick, but the attention she was giving my balls and the speed her lips moved up and down the portion of my dick in her mouth more than made up for that fact. Grunting, my head rolled back on my shoulders and my hips bucked as she seemed determined to drive me towards the edge.
“You should probably slow down,” I told the energetic popstar after another handful of minutes of her going down on me.
“You can cum and keep going?” Taylor asked, taking her mouth off me just long enough to speak. “Or are you a one and done guy?”
The question caught me off guard, as most of the time after a guy came they were out of commission. After all, it was the way our anatomy worked. However, there were times, either it be with help from a little blue pill or a cock ring, or if you were able to stay aroused intensely enough after cumming that would allow you to keep fucking. Since I got to fuck Anna whenever we wanted, I never had to try going back-to-back, at least it had been awhile. With Taylor still rhythmically sucking my suck with pleading eyes, I knew the answer she wanted to hear and I felt our combined motivations could make it happen.
“I can go multiple rounds,” I said with as much confidence I could muster.
“Good. Then I want you to cum in my mouth,” Taylor demanded before resuming her intense blowjob.
Eager to confirm Anna Kendrick’s earlier comments about Og having tasty cum, Taylor got comfortable on her knees and got to work. Shortening her bob so her mouth only worked the top two inches, her lightly held fist gripped the remaining half and stroked her hand and mouth pressed tight together and working as one. 10, 20, 30 strokes and I was able to hold out. I felt and watched as Taylor broke her lip contact with me, though her mouth and my dick were still touching via a lengthy rope of spit, as the popstar took a deep breath of air before going back in.
Taylor gave one side of my dick a sloppy lick, catching some of the dripping saliva she generously applied before giving me a full blowjob experience with all her techniques on display. 10 bobs of each technique should do it, she thought. She used her mouth and fist in unison first, then deep throated his small offering for nearly a dozen seconds. Pulling off to capture some air, Taylor beat my shaft furiously for 10 strokes then went and did 10 bobs with only her mouth. As her hand and mouth went back to suck me off together, I had to give Taylor a jittery tap on her head and neck, the international sign I was about to blow my load.
“Cum in my mouth,” she practically begged me.
Taylor went into her finishing posture, with the first thing she did was make holding eye contact with me, though I was soon screwing my eye close as the wave of pleasure washed through me. I still felt as her hand lengthened it’s stroking distance as her mouth only sucked on the tip of my cock in fast bobs, pleading for my cum. With a mighty grunt I felt the orgasm hit me like a powerhouse, before feeling Taylor only use her hand to beat me off after feeling the first blast of my cum squirt into the roof of her mouth. Circling her fist and lightly stroking me still, I emptied a good 6 or 7 streaks of cum into Taylor’s eager mouth, feeling as she used suction o felt speed my seed’s departure from my sack to her tongue.
Her second hand had dropped between my legs in order to lightly fondling my balls as she gulped down my cum in two swallows. Rather than pull away from me, Taylor kept her lips around my dick and slowly started to bob her head up and down once more, albeit much slower than moments before. It felt good, but my head was still so sensitive from having cum only seconds ago so it started off almost as torture, but after a minute of her blowjob it felt normal, and more importantly, I was still hard.
“Good boy,” Taylor cooed, reaching to her nightstand and taking a big gulp of some drink she had there.
The leggy singer immediately moved to straddle me, not wanting to give my dick any excuse to wilt after so recently cumming. Throwing her leg over my hips, Taylor sat down on top of me she shifted her hips, dragging her pussy along the underside of my cock and causing me to twitch, seeing as how I was still a little oversensitive from her blowjob.
Smirking at me apparently still getting even with me for the light teasing I performed before eating her out, Taylor finally got to business. Raising up on her knees, she reached down she grabbed a hold of my cock before aiming it at her hole. The leggy blonde rubbed the tip along her slit as if to let me know that she wasn’t quite done teasing me yet before finally lowering herself enough to let the head slide between her labia. She stopped with only my head just pierced inside her, maybe to make sure I wasn’t still too sensitive after my recent orgasm. I answered her by taking a hold of her narrow hips and when she started lowering herself onto me again I pulled her down while lifting my hips to drive myself all the way into her in one smooth thrust.
“Fuck,” the wholesome singer gasped, her head leaning forward and her eyes fluttering shut at the sudden penetration.
I didn’t know the last time Taylor had sex, but as we both took a moment to get used to having my cock inside her tight pussy, I couldn’t believe how snug her lips gripped me. She had a reputation for being, for lack of a better word, a slut, which Anna had confirmed earlier. However, though she was far from feeling like a virgin, she apparently had kept her pussy in excellent condition.
“God, you feel good,” I pointed out as she raised up about halfway off my cock.
Both of us were done speaking as she started to ride up and done the entire length of my shaft having properly stretched herself out. I held back from just pinning her hips steady and thrusting wildly up into her for now, letting the singer have a few minutes to work herself on me first. When she moaned and leaned forward with her hands on my chest, I took it as a good sign that letting her have control was warranted at this time.
Still leaning forward, Taylor slowly lifted up about three quarters of the way before pausing. Biting her lower lip she suddenly dropped, taking me all the way into her cunt in one swoop. Moaning she immediately rose up again, apparently having loved the feeling of taking me balls deep.
With my hands still on her hips I let my eyes rove first to her pussy where my cock was sliding in out before moving up her tight flat tummy to her breasts. Even though they were on the small side, especially compared to Anna’s pillowy large set, they still looked amazing and I made sure to spend an extra moment or two memorizing every little detail before letting my eyes continue their journey.
“So gorgeous,” I groaned, reaching around to squeeze her bubbly ass.
As Taylor started to increase the pace of her bounces on top of me I studied the way her lips quivered and curled in concentration. I let her ride me at this slow speed for a little while before I got to eager and wanted to stretch my legs, so to speak. The best part was, my dick was feeling slightly numb from cumming down Taylor’s throat minutes ago, therefore I knew I could go hard and fast without fear of spilling my seed in the star’s womb.
Moving my hands to her back I pulled her down until her perky chest was pressed against me. As she leaned down to kiss me, I realized her breath tasted of red wine, the mystery beverage at her bedside table. Holding her ass, I gripped a surprisingly beefy cheek in each hand before pushing my hips skyward, making Taylor take the entire pole but slow...at first anyway. Digging my heels into the bed, this time when I lifted my hips and drilled up into her, I used as much power as I could.
“Ohhhh,” Taylor moaned into my mouth as I pounded into her.
I opened my eyes and made sure she wasn’t in pain from the sudden shift to aggressive thrusting, but when I saw only pleasure on her face I decided to lengthen my thrusts without slowing down. Stroking my cock in and out of her snatch, I set a tempo much faster than I would normally dare due to fear of cumming. Thus, within a handful of upwards thrusts I could both hear and feel my ball sack bouncing up and slapping the underside of Taylor Swift’s ass.
I was preparing to slow down and let the popstar catch her breath, but when she started to moan with more volume and regularity, combined with clutching at the sheets, I realized that she was closer to cumming again than I’d thought. Though I was tiring physically from the less-than-advantageous body position, I continued to give Taylor the best of my thumping thrusts upwards until my tank ran dry.
“Hold on,” I warned.
Putting a hand on her lower back, I used the other to push off the bed so I could roll over. With me now on top of Taylor, I put my hands on the bed on either side of her and straightened my arms. As her thighs gripped my waist and her heels dug into my ass I set about making the final push towards making Taylor fucking Swift cum a second time tonight. Arching my back I drove the length of my cock deep into Taylor. Before she even had a chance to moan I was pulling back. With almost the full length outside of her pussy I lunged forward slamming back in to the hilt once more, drawing a low guttural moan from Taylor.
“Fuck me,” Taylor gasped as my cock slid in and out of the velvety folds with authority.
As I drove into her we locked eyes for a moment and I could see the burning need for release again in her otherwise green eyes. Since this was our first time having sex with one another, I had no idea how Taylor liked to get off. However, when I made her cum when I ate her out earlier, it was from going deep, fast and stimulating multiple regions at the same time.
With a gameplan in place, I continued my thumping rhythm, driving my entire dick into the depth of her pussy. However, I wasn’t just using brute force because while I was balls deep inside Taylor, I tilted my hips upwards and pushed just a little deeper in order to drag the tip of my cock against her G spot, just like I did in the kitchen to make her cum hard.
“Keep going,” Taylor begged.
“Rub your clit,” I ordered in answer.
Once I saw that Taylor was reaching with her right hand to attack her clit, I shifted my weight to her left and lowered onto my elbow. With her right arm having squirmed between our bodies and her fingers eagerly rubbing her sensitive nub, I used my lower position to drive with more power while maintaining the same technique. Thrust, tilt, push, withdraw. Thrust, tilt, push, withdraw. I lived by these 4 actions until Taylor came, which given the noises being emitted by the singer would be quite soon.
“Cum with me,” Taylor encouraged, rocking her own hips now.
I was getting ready to tell the leggy singer that I wasn’t close to cumming again, but she must have been a God damn mind reader because I was practically ready to pop. In fact, with a few last thumping thrusts, not only was I winning the race, I was crossing the fucking finish line. Since she had begged me to cum with her, I assumed that she wanted me to actually unload inside her womb, despite the fact I wasn’t wearing a condom. I thought of pulling out but the thought of disappointing Taylor Swift and possibly denying her an orgasm just seemed wrong. Just as I was reaching the point where I was going to be unable to hold on any longer, Taylor arched her back and grabbed hold of my shoulders. Taking that as a sign that she was close enough for my orgasm to trigger hers, I drove forward one last time.
“Here it comes,” I grunted as I felt the cum erupt from the end of my dick.
“Oh god,” Taylor moaned, the feel of my seed spurting inside her causing her to go off as well.
As her pussy clamped down even tighter on me it squeezed rhythmically, trying to milk every last bit from my balls it could. Of course I was more than happy to let her have anything and everything I had left, which wasn’t nearly as large of a load that I unloaded into her mouth at the beginning of the night. When I’d finally emptied my balls I dropped down onto my elbows, both of us panting and gasping for air as my cock started to shrink and fell out of her.
“Wow,” Taylor said, her skin glistening both from the thin layer of sweat and the afterglow of the sex.
“Wow is right,” I sighed, rolling off of Taylor to lay on my side right next to her.
“Anna wasn’t lying when she said you had a magic cock,” Taylor shared. “And telling a cock addict like me that a guy has a dick like yours, well, I was powerless but to seduce you.”
“You’re only human,” I consold.
“Thank you for acknowledging,” she giggled. “Anyway, shower is right through there. Your choice to stay with me tonight or I won’t be a lovesick puppy if you decide to leave.”
- 5
- 6
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Dating Anna Kendrick