Lucky Bastard 7: Mixing Business
Starring Anna Kendrick
Codes: MF, Oral, Public,
Written by MiamiLyfe
Disclaimer: The following is completely fictional and it is nothing but pure fantasy







With Ryan's movie now in Netflix's hands and their money in ours, we quickly moved onto pre-production for his next film. The plan was to have Mary Elizabeth Winstead as the lead. We were ready to pitch Anna Kendrick as the supporting actress/second lead. We had thought we had MEW in the bag until two days before our Anna Kendrick meeting. We got a call from her saying that she was not going to be able to take the part. As disappointed as we were, Ryan moved quickly to call Emma Stone. Even though we thought it was a pretty remote chance to get her, especially after winning the Oscar this past year, Ryan still wanted to pitch her. She agreed to meet with him, but the only time she could meet in the next three weeks was at the same time as Anna Kendrick. Hence, Ryan and I decided to try and divide and conquer with him going to meet Emma and me going to meet Anna.

I was more than fine with this situation. Anna Kendrick had for a long time been one of my top celebrity crushes. I know there are plenty of celebrities who are considered "hotter." Still, I was just a sucker for her smile, her rack, and her public personality.

The meeting was set up at a hotel in downtown LA, and I had decided to rent a cabana by the pool to do it. The cabana was a good size with 3 canvas walls, four wicker chairs with ample pillows and padding, and in front were tied-off drapes that could be closed for privacy. I was relaxing enjoying a mojito when I saw Anna walking over. She was wearing jeans, heeled brown boots, and a gray v-neck t-shirt. Pretty casual, but I didn't expect much different. When she came over, I stood up and introduced myself and explained to her why Ryan wasn't there as a server came over to take Anna's drink order.

"So, how'd you guys decide who would speak with who?" Anna asked. "Ryan, pick her because she's the Oscar winner or…."

"Ha. No, nothing like that. I was the one who first convinced him that you were perfect for this part." I answered and then added somewhat sheepishly, "Plus, I'm a big fan of yours, and you were one of my top celeb crushes, so I wasn't going to pass up meeting you."

"Awww, that sweet. Or maybe creepy. I don't know. We'll see how things go." She joked.

We talked for 45 minutes ordering a few more drinks and some appetizers to snack on. We also closed the drapes because tourists kept snapping cell phone pics of Anna. A few even came into the cabana to try and get selfies with her. We talked about the part a lot. She really liked the script, one of her hang-ups was a sex scene her character had. It was an important scene, and she wanted me to make sure we knew she was not going to do any nudity. I reassured her that despite the fact she would disappoint millions of Americans, it wasn't a problem. I told her she could wear a bra, or Ryan could shoot around it so she wouldn't show anything. As we continued to talk, we both joked around a bunch, and she agreed with me that, for the most part, the character she would be playing is a lot like her, with one exception.

"Well, I'm not a slut, though." She said. It was true. The character she was playing was pretty slutty. The on-camera sex scene she was going to have to do was her character proving to Emma Stone's character's boyfriend was a cheater by recording herself fucking him.

"No, but something tells me you know what you're doing." Our conversation had suddenly changed from joking and jovial to one that was highly flirtatious.

"Oh, what makes you say that?" She flirted back at me before taking a sip of her drink.

"Well, there's your Twitter where you' joke' about masturbating in a movie theater and knowing what a spinner is. Plus the story in your book about you high fiving a guy after he makes you orgasm in bed, and I may have heard a story or two about you when I was in Toronto."

"Hey, I have never slept for a part," Anna said sternly.

"I never said you did. Just that when you are in the mood, you are not afraid to grab a guy and have a good time."

"Well, okay, so I'm a girl who knows what I like, and I'm not afraid to go for it when I want it." She said with a wicked smile.

"I'm sure you do," I said as we both took a sip of our drinks while we stared at each other.

"So, what makes you decide to just go for what you want?"

"I don't know. Sometimes I just have a feeling, or maybe I see something that I really like."









At that moment, I decided to go for it, movie be damned. "Alright then, so do you like this?" I said as I got up and stood in front of her and pulled out my half-hard dick.

"Oh wow. Okay," She said in shock, but that shock quickly slipped into a yearning. "Ummm… actually, it's pretty nice." She said as she continued to look at it.

"Yeah, I haven't gotten too many complaints." As I slowly began rubbing myself, making my love stick swell.

"I'm not going to fuck you for the part." She said, looking back up at me.

"Your agent already has our offer. The part, just like my cock, is yours if you want it."

"Well then, if that's the case," she said with a new perkiness in her voice. "Step closer. I'm not getting on my fucking knees on this concrete." She said while grabbing onto me, so I stepped closer, leaving my crotch inches from her face as she sat on the edge of the seat. "Alright," she said as she began stroking my cock, " if we're going to do this, we need to be quiet. It's literally a thin piece of cloth between a bunch of people and us, and I don't need stories all over the internet about me getting kicked out of a hotel for fucking in public."

"Agreed."

"Good." The Oscar-nominated actress leaned in and began taking more and more of my cock into her throat.

"God damn," I said as she switched from quick, shallow bobs to now deepthroating me. "Who'd have guessed a small woman like you could take some much cock into her mouth."

"You can thank all those throat exercises I've had to do for singing." Anna then lifted up my cock and slowly kissed her way down the underside of my dick before reaching my balls and began playing with them. After swapping my balls which ball she was sucking on a few times, she went back to deep throating me.

As much as I enjoyed her blow job, I wanted to hurry things along as I had fantasized about her for several years now. I pulled my cock out from down her throat and grabbed a pillow from the other seat to throw on the ground.

"Hey, what the hell? What's wrong?"

"Nothing's wrong," I said as I dropped down to my knees in front of her. "Now lift your legs up."

"Oh alright," she happily complied, kicking off her boot and pushing off her jeans, then lifting up her legs so I could reach up to pull her black lacy panties off. Once I had slid them off, I snuck them into my pocket, and she placed her legs around my shoulders. With her skirt now bunched up, I had a clear view of her pussy. While not shaved, she kept it very closely trimmed, and her inner labia lips were clearly exposed. This was clearly not the pussy of some young Hollywood teen, but one of a more mature woman who knew how she liked to get fucked. I dove right in tongue first and began eating out the Pitch Perfect star. I could hear her moaning as her skinny legs started to tighten around my head. I pulled my head back a bit, giving her labia lips a playful bite and tug before I moved up to suck on her clit and sank 2 fingers into her.

"UMMMM yeah, that's good," she moaned, "faster though finger me faster" I did exactly what she told me. I worked my fingers in and out of her even faster while I continued to flick her clit with my tongue. Soon her breathing was getting faster, and I knew she was getting close to climaxing. "I'm almost there. Just bend your fingers up a bit. Yeah, rub'em up against the roof of my pussy. Now just go a bit deeper. Trust me, I know what to do." I believed her and followed every one of her instructions as I also continued to suck on her clit. Anna had by this point slid her hand up under her shirt and was now playing with her breasts as her strapless black bra lay on the ground.

"UMMM YEAH, YEAH, RIGHT THERE!" As she got closer, she was also getting louder, so I took my free hand and covered her mouth. I watched her reaction as I continued to finger blast her pussy, and soon I had her screaming into one hand and squirting her pussy juice all over the other. I had been unbelievably lucky to hook up with as many celebrities as I had over the past few months, but watching an actress that I had a crush on since I first saw her in a movie almost a decade ago cum while fingerbanging her at a hotel pool was something else.

"Do you enjoy that?" I asked her as her orgasm subsided.

"Fuck yeah, dude."

"Never would have guessed you were a squirter."

"I don't do it a lot, but a few years ago, I figured out how to do it while masturbating. That was a pretty great day," she said with a smile beaming across her face.

"I bet it was," I said. "Now, take off that shit," I told her as I kicked off my shorts. She did so as quickly as possible, finally letting me see the set of breasts millions of men have been dying to see. Despite in actuality only being a large B-cup to a small C-cup, her breasts looked large on her petite frame and looked to have the firmness and perkiness of someone who was 22, not 32. As I stood over her, she leaned forward and swallowed my whole cock, sucking it for a couple of seconds before bending back in the chair. I grabbed her legs and pulled her, so she slumped down in the seat, and her pussy sat right at the edge. I rubbed the tip of my dick up and down her slit.

Anna took a quick look passed me towards the cabana entrance to make sure the drapes were still fully closed. When she was satisfied, she looked back up at me, "Alright, do it. Stick that fat cock in me!"

"With pleasure," I smiled as I slowly started to sink my cock into her.

"Ummm yeah. Gawd, you have a great dick," she moaned as I slowly slid back out as I was slowly pumping in and out of her.

"I told you I was a big fan."

"Yeah, you did. Now, hurry up and start pounding my pussy!" Once again, I did what I was told. Picking up her legs, I folded her up and began hammering my dick into her. I continued to thrust my hips as I bent down to play with actress's titties, something I'd fantasized about many times. I took one of her small pinkish nipples into my mouth as I groped her other breast and then switched.

Unfortunately, it took too much effort to stay bent over as I fucked Anna, so I picked up the small Into the Woods star into my arms and bounced her on my cock as I continued my assault on her tits.

"God, yes. Bounce me on that fat cock" She moaned. Anna grabbed me by the hair, pulling me off her tit so she could jam her tongue down my throat. We continued to make out and fuck as I turned around and sat down on the chair Anna had been sitting on before. As soon as her knees hit the chair, she took control and began bouncing herself on my cock. With my hands now free, I slid one over to grip her ass and my other to play with her clit.

"That's it tease my clit. I close. Fuck I'm close." She said as she broke our lip lock. I looked on and watched her tits jiggle as she continued to drop her hips on my dick over and over again.

Lost in a feeling of pleasure, Anna arched her back dramatically and bit her lip as she moaned loudly as she came on my cock. The bliss she felt and the joy I felt wanting her cum was quickly replaced with concern as Anna had leaned too far back, lost her balance, and fell backward. I stood up to check on her, and she just laughed as she luckily had fallen with her head hitting the pillow on the ground. I thought about helping her up for a second. Still, as I looked at her resting with her head and neck on the pillow and her legs up in the air resting against me as I stood over her, I decided to try something I rarely did in the piledriver position. Moving her legs into position before squatting down and aiming my dick at her waiting wet hole.

"Oh, we doing this now?" Anna said as she realized what I was going. "Fuck yeah, drive that cock into me." She moaned as I started driving my dick in and out of her. I did not last long as I quickly became on the verge of cumming.

"I wanna cum on your tits."

"Hell yeah, you do."

I pulled out of her pussy sat on the edge of the chair, and Anna tumbled backward before jumping into position on her knees between my thighs. She took the head of my cock into her mouth. She swirled her tongue around a bit before letting it go, wrapping her tits around my dick, and began bouncing up and down. As much as I enjoyed occasionally scrolling the dirty photos of celebs I had on my phone, I would have given them all up if I could have recorded this. Anna Kendrick giving me a titty fuck is something I had masturbated about numerous times.

"Oh damn, Anna, I been fucking dreaming about this for years."

"Oh yeah? You've been dreaming about me titty fucking me? How is it? How does it feel having your big thick cock sliding between my tits?"

"Fucking amazing."

"Yeah, you gonna cum? You gonna cum all over my tits?"

"Yes. I'm so close."

"Do it cum on my tits." I pulled my dick out from between her breast as I stood up. I began stroking my cock, looking down at a nude Anna Kendrick, and within seconds my cock exploded. I shot rope after rope of jizz all over her breast and several landing on her face as well. When it was all over, her chest was covered in one of the largest loads of cum I had ever had.

"Holy shit, that was a lot of jizz," Anna said as she laughed. She took a finger and scraped some of cum off her cheek before taking that finger and sucking it clean. "And it doesn't taste half bad either." As I sat back down in the chair, Anna got up to grab a towel and wipe off her chest. When she was cleaned off, Anna picked up her phone. "Damn. Looks like round two is going to have to wait."

"Why's that?"

"My agent has been blowing up my phone about the contract you sent him." She then stood up and picked up her clothes, then walked over to me and gave me a kiss before she started to redress. We opened the cabana back up and headed for the exit when we were both dressed. Out of the corner of my eye, I noticed that the people in the cabana next to us gave Anna and me a look before whispering something to each other.

We made small talk before her car pulled up when we got to the valet. "Well, this is me," Anna said. "I'll let you know if everything works out. Who knows, maybe you can come over to my place, and we can celebrate," she said cheekily and gave my ass a squeeze before getting into her car. She closed the door and rolled down her window. "Oh, by the way," she said as she stuck her head out the window, and I lowered down so I could hear her better. "Feel free to keep those panties you snuck into your pocket." Anna then gave me a kiss on the cheek and a big smile before driving off.