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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
- 1
- 2
Part 1: The Wager
“The bet is simple Og. I win and I get to experience your apparent world-shattering eating out,” the woman proposed.
“And if I win,” I asked the gorgeous actress.
“Simple. I know you’ve heard of my reputation so if your team wins then you get the best blowjob of your life,” Anna Kendrick answered.
* * *
3 hours earlier
It was finally here….Super Bowl Sunday. The day only came around once a year and the big day was finally upon us. What made it extra special this year was the fact that my favorite team, the Seattle Seahawks were competing for the Championship. They had done so last year and proceeded to go on and win their first title in their history, I was a big believer that they were going to do it again.
Like most of North America, I was going to be glued in front of the screen, taking in all the action as it went down live in Arizona. I was throwing a party at my modest house in Vancouver in Canada, though modest for Vancouver standards still meant a house worth half a million dollars.
It was three hours before the big game and I thought I had everything taken care of. I was expecting about 15 friends over for the game, but that number usually expanded as a friend would bring their new boyfriend or girlfriend. I was ready for this and made sure that the keg was tapped,and extra pizza and wings were ordered. Hell, I even had a small generator standing by, in case we lost power so that we wouldn’t miss any of the action.
I thought I was prepared for everything until my phone rang and I could never have foreseen this occuring.
“Hello,” I asked into the receiver of my cell phone.
“Og! It’s me Anna, Anna Kendrick.”
I was happy that this wasn’t a video call because at the mention of her name my mouth went slack jawed. Before continuing with my narrative I should give background information on myself. I was named Ogden by my wealthy parents nearly 30 years ago and most of my friends shortened that and simply called me by my nickname Og. Naturally that drove my parents crazy, especially my overbearing mother, but thus I digress.
So how do I know one of the hottest (both in terms of work and looks) actresses in Hollywood right now? Well remember when I mentioned my wealthy parents? Well it turns out they got into the film producing business awhile back and I took advantage of this by getting jobs on some of their productions. I was busier when I lived in Hollywood but when I got an offer to take over one of my parent’s smaller companies in Vancouver I jumped at the chance and headed to the rainy city.
I know, I know, I still haven’t answered how I know Anna. Well, just because I got jobs on movie sets due to nepotism doesn’t mean I’m not good at my job, or even personable for that measure. I’m both of those things in spades, so when I was working on the set of a small indie film called Twilight, I was introduced to the talented actress. She didn’t have a large role in the film series, but that was a good thing, as it meant lots of time waiting around on set between shots, and that is when our 7-year friendship started.
“Anna! Shit, long time. I guess you’ve had an excuse with your occasional film scheduling,” I jested, knowing she’s been shooting films for nearly 4 years straight with little downtime.
“Well I’m kinda a shitty friend too…oh and I don’t like you that much,” she replied, not missing a beat.
“Friendly as always,” I laughed. “So what prompts the call to a guy you are revolted by?”
“Well you see, I’m hoping to use you,” she answered.
If it was anyone but the super cute, super sexy actress I would have probably made a joke about using me for sex. However, I haven’t talked with Anna for over half a year, and even then it was only through text, so I went with a standard reply.
“Well as I’ve told you in the past I’m out of the murdering hobo game but I can probably get you contact with someone still active,” I joked.
“I’m so pleased that you escaped, I was growing concerned that the business would corrupt you,” she laughed. “Actually I was hoping to use you for your big screen TV. I’m totally gonna sound like a stalker but I saw you post a pic of it on Instagram a while ago…and I may or may not have done the same on Facebook and saw you were throwing a Super Bowl party.”
“I didn’t know you were so creepy. So does that mean you are in my neck of the woods,” I asked, my interest very much peaked.
“Yeah, I landed here the night before last to do a week of shooting. So I either watch my Patriots kick ass here in my hotel room alone like a loser or hang at your party and feel like slightly less of a loser,” the actress joked.
“Several problems with that. First of all my party is not for losers so I’d have to make an exception for you. Secondly, I’m a Seahawk fan so you will have to check that attitude at the door,” I replied.
“Well seeing as I’ve already invited myself to your party, me celebrating as the sexiest man in the world crushes your pathetic little birds is something you’ll have to live with,” the talent girl shot back with.
“Haha okay fine, you win.”
“Thought you’d see it my way. Text me the address, when I can show and what I should bring,” Anna said.
We exchanged pleasantries again before you hung up. I stood in utter shock for another few minutes as the realization that the woman I’ve had a crush on since we first met was coming to my party. Despite the fact that I always felt that we had a flirtatious bordering on sexual chemistry when we hung out, nothing actually happened. Whenever I had the courage to ask her out on a date she seemed to have a boyfriend, a while a noted hints of jealousy when l brought up a girlfriend around her.
It felt like it took forever for the game time to finally arrive. I tried to occupy myself with busy work, making sure the keg was on ice and that there was enough food and everything like that, but all I could think of was Anna. He always had a thing for petite woman, and Anna fit that description to a tee.
Of course that wasn’t the only of his sexual preferences that the talented actress checked off for him. He was really into redheads, and though she was a flaming ginger, her light auburn locks was close enough for him. Then there was the matter of him being a boob guy, and boy was that an area that Anna was definitely up to task with.
Despite the fact that she was so short and skinny, Anna was truly blessed with an absolutely jaw-dropping bust. In fact, her tits were always assumed to be fake by most who knew her given how perfect they were, however, her great boobs were all natural and just hung perfectly in front of her thin body.
Luckily when people started to show up the afternoon seemed to go by quicker, though his thoughts still would drift to the attractive actress/singer. With every new friend that entered my house I would have hope that it was Anna, but with each passing person it was not her.
Finally, with the national anthem being song there was a knock on the door but I was off doing other hosting duties. I didn’t realize that Anna had arrived until she stepped into the living room and the place feel near silent as all my friends observed the celebrity.
“Anna, you made it,” I said probably too excited. “Oh everyone, this is Anna Kendrick. Anna these are the guys.”
“Hi everyone,” she said with a warm smile and awkward wave, both very characteristic of her.
I got up from the sofa that I just had gotten comfy on for the first time since everyone started arriving and crossed the living room towards her. The auburn-haired beauty wore her locks down, cascading down her tiny frame to about her mid-back. Given why we were all there she wore a tight-fitting woman cut New England Patriot jersey and jeans that looked like they were drawn on.
“Find the place okay,” I asked.
As we approached I opened my arms for a hug which she seemed more than happy to reciprocate. I didn’t want to come off as too creepy and hold the lock too long so I broke contact after 3 seconds and looked at her again. She wore minimal make up as usual, always seeming to get by on her natural beauty, but today she wore some black eye liner which made her green eyes pop even more than usual.
“Yeah totally dude, though the cabbie may have taken longer than I’d have thought,” she replied.
“Beer?”
“Would love one. I brought tequila,” she said, holding up, which got a cheer from my onlooking friends.
I walked her into the kitchen, at which point she filled a cup up to the brim with beer while I tracked down every shot glass I owned, which seemed to be just enough for everyone at the party. We both made ourselves a small plate of food as we chatted about our lives the last few years. When we had finished we headed to the living room and I made room on the sofa with the best view of the TV for both myself and Anna.
“So are you all Seahawk fans,” Anna asked, looking around and seeing most of the guys and girls in some form of Seattle gear.
“I think you’re the only Pats fan here tonight,” I shared.
“Yeah, you Tom Brady groupie,” one of my friends uttered, drawing laughs from everyone else.
“Firstly, Tom Brady is more than a man, he’s a God. Married to Gisele, going to win his 4th ring and is one of the elite QB’s of all-time. I’m no groupie my friend, just an admirer of greatness. Secondly, I was born just outside Boston…ass,” Anna snapped back, eliciting her own set of laughter.
The game was just about to kick-off then a commercial came on for prop bets again. This brought about fresh chatter from some of the partygoers, ending in a few guys asking to use my computer to make a few last minute bets. I told them where it was and focused back in on kickoff…and talking with Anna of course. We continued to banter back and forth for a little while longer as Seattle won the toss and elected to kick.
“You seem pretty damn cocky,” I finally told the beauty.
“I really am,” she said, taking another sip of her beer.
“Care to make it interesting,” I said.
Part 2: Halftime
“So what happens with a tie,” Anna asked me.
* * *
1 hour earlier
Now the bet with sexual implications may have come from left field to most, including myself, but a smaller part of me wasn’t too shocked about the news. When Anna first invited herself to my party a few hours ago, I spent the time researching her by asking some mutual friends we shared. I learnt that she always, sorta had a crush on me and that the time she wanted to hooked up I had a serious girlfriend.
However, I also learnt that Anna was single now, and not only that, but that she hadn’t gotten laid in a while. I hoped that would mean that she was sexually fueled and given how quickly she resorted to a sex bet, turns out I got my wish. Of course she didn’t jump straight into oral sex as the prize, but we had rejected the money bet or the loser having an embarrassment punishment offers in the first place. Her devious mind then went to sex and there was no fucking chance I was turning that down.
We had stayed seated together on the sofa throughout most of the game. Even when one of us would go grab another beer or more food, we seemed to migrate right back to each other. Sure, she was probably doing it because I was the only one at the party that she knew, and I did likewise because I found the petite star to be devilishly attractive, but I’ll take it.
“Another drink,” I offered during the next commercial break, getting to my feet.
“Lead the way good sir,” Anna replied as she followed me into the kitchen.
“So you said I gave world-shattering pussy licking,” I asked her as I filled her cup. “Now correct me if I’m wrong, but we’ve never hooked up.”
“Well that part is definitely true, but let’s just say that Hollywood has no secrets. You’ve worked on a bunch of sets and I guess you’ve hooked up with a number of actresses and well…they talk. You have quite the reputation Og, it’s a good thing.”
I knew of the way Hollywood worked. It was how I knew when Anna mentioned how good her head was that it was the truth. A friend of mine, well more of a work collague had hooked up with Anna once at a party then went and told everyone how great she was in the sack, including how he thought she could deep throat, though that detail was hazy given how drunk he was at the time.
“Works for me,” I said with a grin. “So who gave me the glowing recommendation, if I may ask.”
“The two hot vampires,” Anna said as she accepted the beer.
“Kristen and Ashley,” I guessed, knowing I had fucked both the stars of Twilight years ago.
“And Anna Camp before she got hitched,” she added, referring to her Pitch Perfect co-star. “You kinda are a slut actually.”
“Hey, I take it where I can get it. Besides, I think you were the one who came up with the terms of our wager tonight missy,” I bantered back.
We continued to chat in between plays, though some friends would interrupt us to ask the celebrity questions. Anna was a great sport and answered all their inquiries with honesty and never seemed bothered by the attention. She was actually really cool, not like the impression you get from a lot of other famous people.
The game was going okay. Seattle was struggling offensively like they do on occasion, however their defence had limited damage to only 7 points despite our QB not completing a single first half pass. Finally we pulled our shit together and tied the game, but it was short lived as Brady marched his time down the field and took a 7 point lead once again.
“Shit,” I swore as they went to commercials after the touchdown.
Then something happened that was unforeseen, as if the bet in the first place didn’t come out of left field already. As Anna started to rub in the lead, a commercial for some type of cell phone game came on the TV. The Super Bowl is known for epic commercials and this one was no different, as it cast the gorgeous supermodel Kate Upton.
As transfixed as I was on the TV, so too was Anna. I couldn’t believe it as a subtly looked over at her to see her beautiful eyes glued on Kate, more specifically Kate’s enormous tits as they bounced as though gravity didn’t apply to them within her low cut top.
I kept watching the auburn-haired beauty from the side of my vision and noticed that she all of a sudden began pressing her thighs together…hard. I recognized the maneuver at once, she was turned on and was trying to use the friction from her inner thighs to rub her pussy. I raked my brain and tried desperately to find a way to use this tidbit to my advantage, however it was unneeded.
“So sailer, let’s see how much faith you have in your team,” Anna said to me before the next kickoff.
“What did you have in mind,” I asked, giving her my full attention.
“How about we move up our bet, that way we aren’t bombed at the end of the night and you lacking coordination,” the redhead told me. “I want your A game and this way you can service me at 100% capacity plus drink to forget Seattle losing the Super Bowl.”
“So Kate Upton really did get her all hot and bothered,” I thought to myself. “Well that isn’t the best chance for me now is it? We’re down a touchdown with only half the quarter to go.”
“Hey, if we were reversed I would have enough faith in my team to pull off the bet but if you think your team is so inferior then…”
She was baiting me, I knew it and so did she. But fuck did it ever work. And hell, even if Seattle didn’t pull it out then I could still say that I got to hook up with one of the biggest crushes I’ve ever had. Plis, I was going to try to parlay the bet further.
“Okay, on one condition,” I added.
She smiled, satisfied that New England would hold out Seattle’s sluggish offence from the endzone and thus get to be eaten out to a great and overdue orgasm.
“And that is…”
“If I lose then we have a bet available for the second half as well. New terms but same bet…some type of sex for our own team to win.”
“Hmmm…I guess I can live with that,” she said as we shook hands again to make it official.
The rest of the half went by fairly quickly. Anna was smirking and smack talking twenty people all at once, though seemed to always have time to throw in an extra sting in my direction. Seattle wasn’t faring too well in the game, and with only 31 seconds left in the half they were still down 7 and 80 yards from the goalline.
“Better warm up that jaw of yours,” Anna said so only I could hear her.
I wish I had a snappy comeback for her, but I didn’t. Seattle was resigned to going into halftime losing, which meant I didn’t get to receive Anna Kendrick’s amazing blowjob. Still, being forced to be between her milky white thighs, licking every inch of her twat wasn’t exactly a punishment either.
However, Seattle started to march. A long run by BeastMode followed by 3 passes by the quarterback had my Seahawks only 10 yards out from the goalline. We all watched on as with 2 seconds left on the halftime clock, a receiver who hadn’t caught a pass all year rose high above his marker to make the grab and score the tying touchdown.
We hadn’t thought of the event of a tie game, as when we first conceived the bet we meant for it to stretch for the entire game where there was always a winner. But now that it was all square at the half, we had definitely both won, or loss, but I chose not to think of it like that since I wanted something, anything, to happen between the two of us.
“Would you care for an actual tour of my place,” I suggested to Anna, loudly so everyone could hear.
I didn’t really give a shit about showing off my house to the beautiful girl that I was able to call a friend for the past bunch of years. However, the guise of a tour would be enough to allow us to slip away from the pack of people without them asking too many questions about our hopefully prolonged absence.
“Yeah I guess I was kinda shitty and only showed up right at gametime,” the actress replied.
I helped her to her feet and then we walked around some people as we made our way out of the main room. She’d seen the kitchen already so I showed off the backyard, though didn’t go outside given that there were some smokers out there and I didn’t want to be delayed.
“And is this where the magic happens,” the redhead asked with a grin.
“I would never be so corny as to ever use that line,” I replied, bringing a laugh from her.
“So what’s the verdict Og,” she asked me.
“Well in my opinion, there are no losers out there. I saw we both get what we want,” I proposed.
“Normally I’m not a fan of giving every kid a ribbon even for participation but I like that I’m hearing. Continue.”
“We could 69 I suppose,” I suggested, but my heart wasn’t in it.
There were several problems with that idea. Though it would feel great to have a cock in Anna Kendrick’s mouth regardless of the circumstance, she would be distracted, thus I wouldn’t get the true experience. Based off what word around film sets and Hollywood in general was, Anna could really suck a dick. Not like most girls who were good at it, but Anna had a massive reputation when it came to hummers and I wanted the fully monty, not a half serving.
“Meh,” she replied with a grimace on her face. “Sure it’s probably the act that makes the most sense given the game, but you won’t get my best and I won’t get your best so really, what’s the point?”
“Hmm…I got it,” I said after a few seconds of reflection. “I will graciously go downtown on you first…”
“Such a gentleman,” she joked.
“If you have boobs out during your turn.”
“Interesting,” Anna said as she thought over my offer. “I can except those terms.”
Anna was now seated on my bed, which I was happy that I had the forethought earlier to make when I got out of bed this morning. She extended her hand out to me to seal the deal like we had been doing all evening with bets and deals, but I had something more intimate in mind.
Stepping towards my bed I bypassed her outstretched arm and got right up close to the large-chested woman. Anna’s eyes went wide for a moment in surprise with my sudden action, but she got past the moment and licked her lips in anticipation.
I leaned in and hoped I didn’t push things too quickly with her, but as I neared her, Anna pushed her head forward. I was worried that the moment would have revealed that we lacked chemistry, but we both twisted slightly our heads to opposite sides so our noses didn’t butt against one another. Our lips pressed against one another and held, allowing us to get a feel for the other. Though I was the first to initiate the kissing, it was Anna who was the first to open her lips and push her tongue into my mouth, which I eagerly accepted.
“Fuck, should have realized you were a good kisser too,” Anna complimented, a good minute after we had started.
“Right back at you sexy,” I quickly added.
We caught our breath for a few moments before I leaned back down and kissed her hard again. This time we were more familiar with one another, not to mention more sexual hormones were flowing now, and we hungrily and passionately kissed each other. My hands immediately went to the side of her head, lacing into her hair as her’s did likewise.
With her sitting low on my bed, I hunched over more to give my hands better access to roam her tight body. As we continued to mingle our tongues in the space created by our lips, I moved the palms of my hands downward only a short distance until arriving at her insanely large tits and gave them a firm squeeze. This seemed to bring a squeal of pleasure from the redhead so I gave them another hearty knead before running them down further over her flat stomach.
We continued to kiss with emotion that I didn’t know two people could experience so strongly. It wasn’t just because she was a celebrity, but because I had wanted this girl for 7 years, whether I was fully aware of that fact or not. And now knowing that anna had felt the same about me made it even better.
Over course I didn’t leave rubbing her tits just to feel her stomach, as my goal was clutching the bottom of her tight football jersey. She knew exactly what I had in mind so as I lifted her shirt upwards, the talented singer rose her arms straight above her head to allow it to be pulled free. I made equally short work of her bra in order to reveal her large tits for the first time since knowing her.
They were even better then she had been imagining for the past 7 years. Huge for her size, perfectly round and suspended firmly in front of her with the cutest pink nipples, I had to remind myself to swallow and not drool. Having stopped making out with her to observe the fine specimens, I leaned back towards her, taking her left tit in my hand and began sucking. Anna wasn’t surprised by his focus being solely on her tits now, most men she had been with did the same, but what did catch her by complete surprise was when I bit down on her now erect nipple.
“Aawwhh,” Anna screamed sharply.
It was a risky move to pull on someone when we just started to hook up, but with Anna I felt like I needed to be different and live up to my apparent lofty expectations. I knew it would hurt her at first, but then I could feel her relax again, allowing me to sigh as now I knew it felt good after the initial shock.
I released my grip after a few more second then slide to the other boob and did the same there. She yelped again then followed it up with a chorus of moans. I could tell that she was upset slightly when I unclamped my lips and teeth from her impressive mounds but it was only so that I could wrap my arms around her petite frame and lift her off my bed.
Out of reflex I imagined, she immediately wrapped her jeans-clad legs around my waist to make sure I didn’t drop her, which would never happen. It helped that she weighed maybe just over 100 pounds, but it had to do with the fact that I was a monster. I stood roughly 6 foot 1 inch, but I was bulky and enjoyed working out, making me look like I played professional football for a living.
I didn’t intend on holding her for very long either as I only planned on laying her at the top of the bed with her head on the pillows. As I got my knees on the bed and lowered her down again, laying her flat on her back, she unhooked her ankles from behind my back and found my mouth with her tongue again.
“My God you’re sexy,” I said, having broke the kiss and looking down on the topless girl.
She reached up and took my head in her dainty hands as she kissed me again, though I didn’t intend to stay in this position for long. Still propped up on my knees and hands, I steadied my weight on one arm while my other went down her body, squeezing her massive tits of course, until my fingers found the bottom of her jeans.
“I’ve wanted to for so long,” she moaned.
Anna knew exactly what I wanted to do as she hiked her hips up, lifting her slender but cute little bum off my bed. I took advantage of her assistance by using both hands to grip the top of her pants and pull them down. They were practically painted on her slim legs but my gym-carved strength was easily enough to overcome that and they were off her altogether.
“Me too,” I breathed.
Now finding myself sitting back on my knees, I realized I had pulled her thong down her legs with the pants. Now completely naked, I looked over and observed the sexy actress. Her legs were slender, making her petite frame look even smaller, matching well with her narrow hips. Her stomach was flat and led into her bright pink snatch, made all the more observable by the fact that her pussy was shaven bald, which made my mouth water.
“Like what you see,” the girl asked.
Though Anna was normally a cocky person, she was well aware that her body was ridiculously amazing. Her legs may not be everyone’s cup of tea, but the combo of a nice round ass, bare cunt and overflowing tits made a lot of men cream themselves early. Looking up at me from the top of her bed, she bit her lower lip with the sexiest look I could ever imagine her making.
“Very much,” I said, leaning back in to kiss her.
While shoving my tongue into her mouth with some finesse, my fingertips brushed down her amazing body, lingering over her large mounds. Begrudgingly I left her best feature, roamed over her flat stomach and bare patch right below until I dropped down and felt wet folds sliding past my fingers. Presumably out of reflex, Anna thrust her hips slowly forward, essentially trying to fuck my hand. Of course I didn’t need the help as the second of my fingers touched her moist heat as I drove a solo digit as deeply as I could inside her.
“Oh God yes,” the beautiful creature screamed.
Anna’s moans became stifled when she grabbed the back of my head and pulled me even harder in for more kissing. The tiny actress linked her arms behind my neck so that she could deepen the kiss. Her tongue flashed inside my mouth but would be needed to frequently groan and moan as I continued to slowly pump inside her twat.
“I’m gonna need you to break your superhuman grip on my head,” I told my dream girl while working a second finger into her unbelievably tight snatch.
“And why on Earth would I do that?”
“My tongue and your pussy getting to know each other better,” I answered bluntly.
Anna couldn’t help but sigh with disappointment when my fingers pulled free from her dripping pussy. I gripped both hands on her inner thighs, widening them as far as possible to allow my massive frame to fit between them. She responded immediately and did as I prompted without fighting, so I slinked down her petite frame, my mouth finding her nipples again as I descended.
“Mhmm…yes,” she groaned again.
Without hesitating any more I leaned my head inwards and felt my stubbly face brushed against the soft skin of Anna’s inner thigh. Her hands immediately reached down to rub through my inch-long sandy blonde hair, not to pull me away but just to have more contact with me. Not waiting any longer I stuck my tongue out and ran it along the entire length of the pretty girl’s slit.
“Ohhh…mhmmm,” Anna screamed.
I was pleased when her fingers tightened in my hair, pulling on the follicles as she already began to thrash above me on the bed. I didn’t want to blow her mind too quickly so I slowed it right down, using my lips to kiss her lower lips. It had the desired effect as the redhead settled back onto the bed, allowing me to continue working over her pussy without restraint.
Of course her wanting to take control reared it’s head again when I crammed my tongue into her snatch with surgical precision. Her hands reached down once again and clutched the back of my head in an attempt to get my tongue to drive even deeper into her very wet snatch.
However, I wasn’t going to let the feisty Pats fan work my like a puppet, albeit one very good at going down on women. My reputation was well earned and was happy to hear that women talked favorably of me as I was quite an accomplished pussy licker, so I wasn’t going to let the talented and sexy actress call the shots tonight.
I was able to reach a hand between her thighs, which Anna was using to squeeze my head in spasmodic episodes when one of my maneuvers filled her with too much pleasure. My fingers spread her pink lips apart to give me clear access to her clit, which was standing in clear view for me. The first time my tongue flicked over the concentrated bundle of highly sensitive nerves, her lithe body went rigid from the intense sensation.
“Awwwhhh…shitttt,” Anna cried out, louder than ever.
“Thought you might like that,” I told her, other hand snaking up to squeeze her large right boob.
I wasn’t just going to talk to her while I did my damnest to give her the best rug munching of her life so I got right back to work. My tongue went back into her slit, licking as deep inside her twat as I physically could. She tasted as good as I could hope, sweet with a touch of acidity, which made me more than happy to linger as long as I could inside her honey pot.
I didn’t forget the response I got from attaching her sensitive bean so after another minute of deep licking I withdrew. Any disappointment from me leaving was soon dispelled as my tongue was replaced with two fingers, easily sliding inside given the amount of wetness she was flooding outwards. Her moaning was increased to a high volume once again when my tongue moved north and found her clit, giving it several lingering licks before I latched my lips around them and assaulted the nub with both suction and my wet muscle.
“Oh sweet baby Jesus!”
Now I knew that I could keep up this technique, constantly alternating between fingers in the snatch with mouth at the clit and vice versa, but I wanted to give her my full arsenal of tricks. With my index and middle digit plunging deep into her twat, sliding along her G-spot before withdrawing and repeating the process, I let my 5th finger hang down. Over the course of a minute it had first landed on her left ass cheek then migrated down until it was resting right over her backdoor with the faintest of contact.
“Living up to my reputation,” I asked.
“Mhmmm big boy,” she replied, body thrashing about.
I noticed that even with the slightest of touch against her asshole, Anna didn’t back away. Instead she continued arching her back and flopping around on my bed as I ate her out superbly. With the waters tested and seeing that she wasn’t repulsed by some anal play, I had my game plan settled on.
“Whoa,” Anna screamed.
The response was a direct consequence of me having grabbed her narrow hips and flipping her 180 degrees over. It pained me that her tits were now covered, being pressed into my bed, leaving me unable to grope them further, but it was all part of the plan.
My fingers, which were withdrawn from her sopping wet pussy to roll her over didn’t go back into her twat, instead that honor went to my tongue. My hands were being used to hold her hips steady, and occasionally to run up along her spine, making her arch back into my mouth further.
My motives for the change in position was so that with my tongue buried deep in her wetness, my nose was pressing directly against her asshole. It could have been a risky move for both of us, but with the water tested I figured she wouldn’t mind plus it wasn’t a direct attack against her booty, able to be played off as accidental contact in case she was super protective of her backdoor like a good amount of women were.
Anna was not one of those girls. My senses were on heightened alert for even the faintest of responses when my nose touched her, but they didn’t need to be as the moan she let out as my tongue buried in her snatch at the same time was almost the loudest of the night.
The adorable redhead was on the ropes right now and I figured now was as good a time to finish her off as there ever would be. I had been going down on her for nearly 15 minutes, she still had to do me and we both wanted to catch the start of the second half of the football game after all.
Even though I had tested the waters progressively, both with a soft finger pad and ‘accidentally’ with my nose, this was the hail mary attempt now. It was a risky move, as I’ve blown a few one night stands with being too rash, but those that liked it tended to cum harder then they ever had.
Having done drums in high school music class I was able to keep beat with three different body parts. For drums it was left hand, right hand and foot, while with eating a girl out it was both hands and tongue. Moving my hands from her hips down to her pussy, Anna was responsible for keeping her face in the pillows and ass in the air so that my left hand could rub her clit while my right hand buried two fingers into her twat.
“Oh fuck….oh fuck…oh fuck,” she swore.
“Getting close,” I asked rhetorically.
“Mhmm,” she moaned in response anyway.
I took one last deep breath, steeled any last remaining nerves and took sight of my target; her cute-as-a-button asshole. Leaning my face in, I could feel my stubbly beard light scratch the bottom of her adorable ass cheeks as I stuck out my tongue and placed the tip of my tongue on her ass. I made the contact as broad as possible to only lap at her hole rather then trying to jam it into her kester, which may have caused a defensive reaction.
“Awwhh….mmhmmm…ugghhh,” she moaned in response.
“Gotcha,” I thought. “Cum for me baby.”
I knew I had her now and she would be cumming in short order. With a triple stimulation going, not to mention her sensitive nipples rubbing against my bed sheets, was easily going to make her orgasm, and my bet was within seconds rather than minutes.
“Keep going…almost there,” she beaconed.
Then it was her turn for the surprises. While I continued to lick her crinkled rosebud, Anna snaked one of her arms backwards so that she could clutch the back of my head. This was unexpected and I was thinking she was going to push me down, back to lap at her clit or in her twat, but instead she pressed my face further into her ass.
Figuring what she wanted I made my tongue pointy, braced it with a strong jaw and did more then lick her. This time I was trying to force my tongue into her backdoor, and I had some success as I felt her sphincter give slightly, just enough to be able to lick around the very entrance to her asshole. This, apparently, was more then sufficient for the talented actress and singer.
“OHHHH YESSS AAWWHHHHH!”
With a loud scream that surely everyone in the house, if not the neighborhood had heard, Anna came all over the fingers I had buried deep in her pussy. Apart from feeling her gyrating body go rigid, and the added pressure in her twat, I could also feel her asshole quiver as she came, allowing me to briefly lick all the way into bowels rather than just rimming the hole, however that was short lived.
I knew my time between her thighs was over and that any more effort tonguing her asshole would be potentially negative so I withdrew my mouth and fingers from her holes. Instantly, as though I alone was holding her upright, she flopped down flat on her stomach, her ass jiggling in the process. Still close to her smoldering sex, I really wanted to taste her right from the source so I dipped back down and licked deep in her twat, tasting her lady cum.
“Sorry, couldn’t help myself,” I said with a grin.
Anna flipped herself back over at this point, giving me another long look at her amazing tits. She looked at me with a stunned expression then ran a hand through her long hair, much like I had seen her do countless times in the movies as she played awkward characters.
“What,” I asked after 10 seconds of her just staring at me.
“You…I mean…fuck! That was absolutely fucking amazing,” Anna complimented.
“I’m glad to be of service,” I replied with an exaggerated bow.
“Oh you were,” she said, rocking up to her knees to be at a similar height to me. “How’d I…you know…taste?”
“So good,” I replied, aware that I probably had wetness still around my lips and mouth.
In a move that surprised me, the tiny actress reached down and grabbed my thick wrist in her hand. While her dark lined eyes held my gaze without blinking, Anna lifted my arm so that my hand was level with her face, opened her mouth and proceeded to suck on the fingers that were buried in her cunt while she came seconds before. I could honestly say that my cock physically hurt with the amount of blood currently filling it as she worked her skilled tongue around my fingers.
“I really do taste good, don’t I,” she grinned, licking her lips. “Now get that shirt off.”
I didn’t hesitate listening to the songbird and immediately reached down to the bottom of my jersey to pull it over my head. She too was busy, making short work in her naked state of my belt and jeans, having my pants slack. We had surprisingly good chemistry for a couple hooking up for the first time as she cued me wordlessly to sit on the edge of the bed. As I got into position she skillfully removed my pants, leaving me nearly as naked as she, except my boxers remained.
Anna leaned in to kiss me one last time before she began a trail of kisses down my neck, and over my powerful chest, at which point she slunk herself onto the floor, settling on her knees between my powerful thighs. Her tiny hands found the waistband of my silk briefs and pulled them over the tent that had propped them up, exposing my cock to her for the first time.
“It’s…wow,” Anna exclaimed.
I wasn’t a cocky person, but I was rational and knew that I was well endowed when it came to my dick. Standing a solid 8 inches long, it was also girthy to the point that one ex-girlfriend said it was better than most cocks in porn. Having seen the odd video myself, I was forced to agree with her assessment. Apparently Anna agreed as well, as the look of joy on her face and the way she licked her lips in anticipation told me that she was pleased with what she had to work with.
Despite her reputation, which was glowing when it came to sucking cock, she didn’t dive in and blow my mind right away. Leaning in, the little redhead puckered her lips and kissed me right on top of my tip with softness. To continue her teasing she kept that tactic and moved down my shaft on one side, then kissed her way back up to the top again, which was driving me absolutely insane with lust.
I was on the verge of begging her to suck me with earnest, but she must have read it on my face, and it must have been what she was after. Anna wasted no time in opening her mouth as wide as possible and taking easily half of my good-sized length between her lips.
“Holy fuck,” I exclaimed as her moist heat worked its way over my shaft.
I couldn’t help but look down and observe Anna in what looked to be her natural environment; on her knees with a cock in her mouth. After taking half of me in her mouth she planted her lips completely around me and bobbed her head back towards the tip. Her mouth felt warm then I imagined and the way her lips dragged along my skin made me want to pump her full of cum right then and there.
“If you liked that,” she said with a glint in her eyes. “Then you should really enjoy this.”
I continued to watch her, especially after her cryptic words and felt as my bulbous head touched the back of her throat. It was usually at this point most girls coughed a little bit then rapidly withdrew my dick from their mouth, but Anna was not most girls. The slim redhead kept moving forward until my tip slipped into the tight confines of her throat. She continued to drive more meat into her mouth until her cute nose was buried in my trimmed pubic hair and her lips were wrapped around the very end of my pole.
“Sweet Mother of God,” was all I could groan.
It felt better then any other blowjob I had ever received and it was only the first minute. I’ve had the odd girl that could do what Anna was currently performing but this was different, better. For one those few other girls weren’t Anna Kendrick, the adorable yet sexy actress that I’ve wanted for years. Plus she had more flair and theatrics which really heightened the atmosphere.
It also didn’t hurt that she was stimulating more than just one sense, she was doing three which brought things to a new level as well. Her lips and throat felt great on my shaft as she bobbed on my whole length over and over again, while she was more than fine with letting me look down and watch her talent, some other girls were weird about that. However, hearing the gurgling noises as Anna gave me that great blowjob was truly remarkable. The noises only increased in volume and frequency as the large breasted woman went from slowly and methodically taking my entire cock into her throat to ramping up the speed greatly.
“Fuck yes,” I couldn’t help but groan.
“Grab my head,” she somehow was able to speak before descending back down on my dick.
Anna took her hands from holding up her slim upper body to placing them on my hips so her fingers were pressed against my firm ass. Her small but toned biceps bulged as she held herself up in that position with her mouth still on my cock. Although she was only able to move her lips over me a very short distance, it gave this Seattle fan the ability to have complete control over her.
To say I was impressed with the tactic of the busty girl would be an understatement, and I was more than willing to take advantage of the unique opportunity. Anna had already showed off her gift of being able to take my whole dick in her mouth so I had no problem with face fucking her, which was clearly what she wanted to happen.
I would have jumped at the chance to do this with anyone, but with this particular redhead made it all the better. That was because Anna’s face was how I would describe perfection; cute but still sexy with just a hint in her big bedroomy eyes that she’ll do whatever nasty shit in bed that you’re into.
Grabbing the sides of her head, I began pulling her towards my lap slowly until I could feel her nose touch the lower portion of my abdomen. The feel of her lips gliding around the very base of my dick was beyond words and after I took a moment to marvel in the occasion I retreated her along my length until only the tip remained in her mouth.
“Glluuuggghhhhh,” Anna gasped as air filled her lungs again.
I allowed her a moment to regain her composure and some air while also taking the chance to wrap my monstrous hand in her long red hair with my other hand going to rest on the side of her face. She wanted me to have full control of the blowjob and that is what I planned to do.
With my new grip, I began the same method again but this time I could feel Anna pulling my hips towards her as best she could. When I looked down and saw her flash me with her large eyes, she pleaded for me to go faster. Whether it was her visual cue or the wave of horniness I was getting when looking down on her with half my meat pole in her mouth but I retracted hard on her head and sent her face crashing into my stomach.
“Gggulllllggkkk,” Anna coughed as spit slushed in her throat.
With any other girl, I would have bet dollars to donuts that spit would have been dangling from their mouths and covering their chest. However Anna was different. Probably cognitive of the fact we had to rejoin the party after blowing me, she appeared to be spending a good deal of focus to continuously slurp back her own spit as I pummeled her throat with my pole.
“This…your mouth…is great,” I eventually said after another 5 minutes of face fucking the beautiful girl.
It came at a great cost though. As much as I would have liked Anna to have sucked on my cock all night, I knew that was a pipe dream. The fact was, I needed to cum soon, however I would dare anyone to try to last longer then this if they were working with what I was dealing with.
“I’m cum soon,” Anna asked.
She probably summarized that when she felt my grip of her hair and face slacken. She used that to pull free of my dick and move further down, really sinking onto her knees and getting her face beneath my tool to where my full balls dangled. Opening her mouth, she didn’t beat around the bush at all, taking them within her warm wetness.
“Fucking close,” I groaned with eyes closed, thinking of ways to prolong my orgasm for as long as possible. “Where do you want it?”
“Cum in my mouth,” she stated matter-of-factly.
As soon as the words left her mouth her lips went right back to being wrapped around my sack. It wasn’t like she was neglectful of my cock or anything, her hand was blazing up and down the spit-soaked pole with blinding speed as she beat me off. I did my best to starve off my climax but it was a losing battle so I reached down to guide her head back to the prize.
Anna took the hint immediately, knowing time was of the essence and wrapped her lips back around my meat. I pushed her head down one last time, feeling her constricting throat muscles squeeze my cock for all it was worth before withdrawing so only my head remained in her mouth. She took control of it from there, closing her lips tightly around my crown and sucking for all she was worth.
“FUUCCCKKK,” I swore loudly.
I could my cum exploding out from the tip, streaking on to Anna’s tongue just as she wanted. The first few squirts were pressurized and I could imagine them jetting to the back of her mouth while the rest of my goo poured right out onto her taste buds, coating them in my salty load.
Instead of swallowing or spitting the cum right away, Anna surprised me a final time by pushing her head down into my lap once more. I nearly came again, if I had anything left, when my dick disappeared back into her throat and was hugged on all sides by her vocal cords. After what felt like an eternity, but what was probably only a few seconds, Anna withdrew me completely from her mouth and then in a dramatic fashion, so I knew exactly what she was doing, swallowed my entire load down in one audible gulp.
“Yum,” she said as she smiled up at me from her knees.
We were both exhausted and sexually spent but as we took a few moments to collect ourselves we heard from my open bedroom window someone shouting at the smokers below that the game was about to restart. Anna and I looked at each other one last time then sprang into motion, sorting through the clothing for our own and getting dressed with haste.
We threw the clothes on then Anna gave herself a look in the mirror and noticed her crazy, wild hair. She took a few seconds to pat it down as best she could, but she knew it wouldn’t return down to it’s normal smooth look. I opened the door for her and we rushed down the stairs and entered the living room just in time to see New England kicking off the half.
Of course, at our reappearance we were greeted to a round of applause by the rest of the party, who had clearly heard our theatrically moaning and screaming from up above. We both flushed red in the face, but our embarrassment wasn’t enough to stop us from getting back into our seats and watching the second half unfold.
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Dating Anna Kendrick