The Perks Of Being A Podcaster Pt 15

All of the following is complete and total fiction. Not a word of it occurred, now would it.

The Perks of Being a Podcaster

by MrMaxLord

(MF, oral, Cons, Anal)

Chapter 15: Hailee Steinfeld

*****

After my insanely hot romp with Anna, I was all ready to spend some time with Hailee. The plan was she'd come down and we'd spend the week together up until her appearance on the show. Sadly, the best laid plans of mice & men and all that. Hailee had forgotten she was already going on a family vacation to Hawaii. It was no big deal really. Just gave the show an extra week off. We slapped together a best of show and Hailee both rescheduled the show and time with me.

Honestly, it did work out for the best, as it gave me more time to make plans for the two of us. And Hailee being Hailee gave me a lot of inspiration via her Instagram pics...as well as some private ones. Nothing worthy of a Fappening hack, but bikini pictures are always super fun.

So, when she came back from Hawaii, after a jet lag killing nap, Hailee got ready to meet me at my place. The plan was pretty much the same as it had been, except now she was meeting me in the morning. The drive was going to be long, so common sense drilled into me by a father obsessed with road trips demanded we start early.

It was about five in the morning on a a Saturday. I was waiting outside my place with a big thermos of damn fine coffee and a sack of assorted snacks. Road Trip 101.

I was checking the tire pressure when Hailee's Uber pulled up and she hopped up, a big bright smile on her face and a duffel bag in her hand. I got to my feet to greet her, but she beet me to it, wrapping her arms around me and kissing me deeply and tenderly. I pulled her close as the kiss broke and her almond shaped eyes looked at me.

"Good morning," she smiled. "You ready?"

"For the drive?"

"Of course," she said with a grin. "And anything that happens during it. She winked at me and headed for the passenger's seat. "It open?"

"Yeah, hop in."

******

As soon as Hailee and I were in our seats and buckled up, we were on our way.

"So, what do we have for snacks?" she asked.

"Packed some of those mini-cereal boxes, some chips, fruit, couple sandwiches," I said. "Bag's right behind you."

Hailee grabbed for the backpack and unzipped, eagerly rummaging through the contents. "Probably just going to go for an apple or somethingOH MY GOD YOU HAVE FROSTED FLAKES! I LOVE Frosted Flakes! Do you have any milk?"

"Yeah, should be some in the mini-fridge in the back."

"Mini-fridge?" Hailee turned her head to the back of my van, getting a full view of the conversion work I'd put into it. "Holy shit, did you do this yourself?"

"Yeah. The side of the van without a door has a frame built in. Move the latch and it lowers out for an air mattress that is stored right on the back doors. Should be some shelves on the other side of the van with a baggie of plastic spoon and crap. The mini-fridge is also right next to the back door as well."

"How did I not notice this?"

"Well it was before the sun came up and you were clearly distracted by my incomparable charm."

"Clearly." She unbuckled her seat belt and traveled to the back of the van to hunt for her much-needed milk. "You have any plans for this bed?"

"Only if you do."

"Ha, good answer." I heard the fridge open and shut and soon Hailee was back in her seat, the precious, cereal drenching milk now hers. "You actually bought those teeny little single serve milk cartons! Those are so freaking cute!" With the required ingredients in hand, Hailee happily dug into her sweet treat of sugar-encrusted corn flakes.

"So," she said between bites, "Where are we going? You said something about the hot springs or something?"

"Yeah. We're going to a cabin up in Big Sur. It's got a decent spring close to it. The cabin also has a hot tub, which honestly seems kind of redundant when it's just a small hike to a natural source hot water."

"Well, I'm sure we could find a way to get some use out of the tub," she smirked. "How did you get a hold of a cabin though? A sponsor?"

"Oh no, it's my parents'."

"Really?"

"Yeah, I know someone wouldn't guess my parents have money from my apartment, but yeah. They actually own one of the resorts up there."

"Wow, really?"

"Yeah. I grew up with some money in the bank. It's how I met Troian actually. Her family is kind of Hollywood. Dad's big in TV. However, the reason I don't exactly look like I'm living the life of luxury is because I was cut off for a long time."

"Why?"

"I didn't want to run the place so I chose to make a career of farting around on the internet. Didn't go over too well until I actually started making money. Now it's all smoothed over, but it was tense for a while there."

"Well, it looks like things worked out for the best."

"Well, yeah," I said. "I make money my way, make my own choices, and I think I tend to have pretty great company around me."

Hailee smiled, licking her lips before looking at me again. "You don't have to butter me up, I'm already here. But it's appreciated." She leaned over and kissed my cheek. "Now, lets get some tunes going. I mean, it's not a real road trip unless there's some music."

******

After finishing her cereal, Hailee dozed off in the passenger seat. I was a little tempted to wake her to keep me company. But she just look so insanely cute, I didn't want to wake her up.

Three hours into our drive though, Hailee woke herself up as I parked at a rest station.

"We there?" she asked, groggily regaining her bearings.

"No, just at a rest stop." I replied. "Needed to go to the bathroom and stretch my legs."

"Good idea, I think I'll join in. Feel like a have a crick n my neck or something."

"I could try and rub that out for ya," I said while cracking my knuckles.

"Oh, I bet you could then mysteriously find aches and pains that only your gifted finger could cure," Hailee said in the cutest teasing tone I'd ever heard. "But first, let's take care of the usual road trip business before you do any full body search on me?"

"Fair enough." She gave me a quick peck on the cheek before we both headed off to our respective restrooms. It wasn't long, because who wants to spend that much time in a rest stop bathroom, before we met up again and took a short stroll around the rest area.

"It's so beautiful," she said. "I mean, we're just at a rest stop and we're already getting stuff like this. Those trees...pretty birds...it's so cool, don't you think?"

"Yeah,"I agreed. "I hate to say it because it makes me sound like a jaded rich kid, but I came up here so much as a kid I'm kind of used to it. But the company is making it a lot better."

"I give you a free pass on the jaded stuff for the sweet compliment." Hailee grabbed my arm and moved closer to me. "It really is beautiful, though."

"Well, maybe we should just have lunch here. I mean, it's not like we have to worry about check in deadlines. My parents own the cabin. I could pull the van in a little closer to the trees, we chow on the sandwiches."

"That sounds perfect."

"Cool. Just hang here and I'll be right back." I gave Hailee a quick kiss and hopped in the van, moving it into the perfect position so when the back doors opened, we could sit down and directly face nature. I moved to the back of the van and opened both doors, letting Hailee get in and sit down. "What's the sandwich of your dreams?"

"You wouldn't happen to have turkey on multigrain wheat, would you?" she asked.

"Actually, yes." I replied. I grabbed two sandwiches out of the bag and handed one to her then sat right next to her. "Water's in the fridge."

Hailee got out a couple of waters and handed me one. "Did you pack the multigrain just for me?"

"Well, as many points as it would gain me, I just get that kind of bread already."

"Wow, Frosted Flakes and multigrain bread. I give your taste an A+."

"And I thought the van was the sinker."

"Not gonna lie, the foldout bed frame and air mattress was pretty cool," she laughed.

"Well, you wanna test it out?"

"See, you even know how to take a hint." She grabbed my sandwich and put our lunch in the fridge. "Close the van doors."

Hailee got in and I shut the doors, I went to let the bed frame down when Hailee stopped me.

"Don't bother," she said. "Just gonna get in the way right now." Hailee descended on me, kissing me hungrily as she straddled me. My hands moved under her skirt and over her long legs to her hips, where I was surprised to find she wasn't wearing a stitch underneath.

"Took 'em off in the bathroom," she said with a grin. "Must be that fresh air. Now unzip your pants, 'kay?"

As soon as the request was made, the pants were unzipped. Hailee grasped my cock, rose up, and slowly sank down on it.

"Oh fuck, baby," she moaned, biting her lower lip. "Mmmm fuck yes." She let the top of her dress slip down, her breasts meeting the air of the van and then, the moment she leaned over, my eager mouth.

"Mmm Bart, your mouth feels so good...mmm keep sucking my nipple baby...just like that."

Her hands reached to mine, grabbing and interlinking our fingers as our movements started to really rock the van. Hopefully no one would come knocking.

The shocks were really getting a workout as Hailee rode me. She wasn't acting like she was on a bucking bronco, but it felt amazing all the same. And it wasn't all tactile, the view of her enjoyment and the moans coming from her mouth added everything.

Our hands separated and I went to her hips, caressing my way up from her thighs and then to her ass. Tight, shapely and firm. It felt perfect in my hands.

Our eyes locked as I rose up, Hailee's amazing legs wrapping around me.

"You want to take control, dontcha?" She cute smile threw gasoline on the fire, and the sparkle in her brown eyes didn't do anything but heighten the mood. I began to thrust up into her, holding her tight as the pace picked up.

"Fuck Hailee," I moaned. "Fuck you're so good...everything...god damn it yes."

"Fuck baby, don't stop," gasped Haileee. "Oh make me cum...make me cum on your cock! I want you to feel it...feel what you're doing to me...oh yes please baby!"

I sped up, Hailee leaning back as things got more and more intense. If anyone was passing the van, if the movement wasn't a dead give away as to what was going on inside than Hailee's moans would definitely do the trick.

We shifted positions a bit, with me sitting completely up, back against the door and Hailee in my lap, her back to me. She braced her arms against the roof as I held her hips tight and drove into her.

"Yes yes YES!" Hailee cried. "Ohhh don't stop...so close...promise you won't stop...oh yes!"

She leaned back against me, writhing and grinding on me. My hands cupped her breasts while my lips kissed the nape of her neck and her spine, Hailee moaning a little more and more with every passing second.

Hailee was shaking in my arms, just on the edge and grinding on me. I reached down and began to work her clit and with that extra charge, Hailee went into overdrive.

"Oh my GOD!" she exclaimed, whipping her hair back as she arched her back. She leaned back, turning her head just enough to kiss me. face and kissed me deep, moaning into my mouth as her orgasm moved threw her body. "Mmm I want you to cum in mouth."

"Well, I certainly won't argue with you." I replied.

"I love a smart man," she said with a wink, kissing me before getting off of my cock and lying on her stomach between my legs. Her deep brown eyes looked up at me as she began to suck me off. There was no slow period, no build up, Hailee hit the ground running, her mouth and hands working in unison to get me off. Which was far too close to happening.

"Oh...oh Hailee!" I moaned and twitched as she swallowed every stream I had to shoot before I finally fell over. After a couple of deep breaths I felt Hailee move next to me, lyingher head on my shoulder.

"So, here's what I'm thinking," she said. We catch our breaths, grab our lunch, and eat while we're on the road. We pull into the cabin, you show me around the place. If there's any embarrassing baby pictures I demand to see them. Then after we've unpacked we ravage each other until we lose the ability to speak."

"Well, I was going to suggest a wine tasting but I like your idea better."

"Like I said, smart man." She climbed on top of me and softly kissed me. "So..on the road again?"

******

"Wow," said Hailee. After or little romp in the back of the van we got back on the rode and she zonked out again, pretty much sleeping all the way to the cabin. Once she had stepped foot in it, she was floored. "This is...this is nice."

"Yeah, my parents kind of have specific tastes...and those tastes call for a lot of open space." I replied.

"I can see that." The cabin did seem fairly bare. Yeah, there was the basics like a couch, chairs, a fireplace, dining table, a kitchen, but not much in the way of flare. "They must be very into minimalism."

"Well, like I said, they own one of the resorts up here. Usually they just stay in the suite. This is more of a get away from the resort. Like when a really rich or needy guest comes in, they retreat here to get spared the headaches."

"Good plan." she replied. "But if they never really used it, does that mean we need to go shopping for food?"

"No, it's fully stocked. I told them I might be using it for the New Years break for the show. So we don't even have to leave the bedroom unless we're REALLY hungry."

"Well, that does sound very appetizing, but I do believe I was promised some hot spring and jacuzzi action."

"That you were."

"So, how about this," said Hailee. "We strip down, get dressed for a nice relaxing hot spring dip, then come back here, strip down again and not even bother putting on clothes for the rest of the week?" Hailee finished her question by smiling that smile, cutely placing her tongue between her teeth.

"You have the best plans." I replied.

******

"What are you wearing under there?" I asked. Hailee and I had changed clothes for our short hike to the closest spring I knew. Now, it wasn't freezing or anything, but still we decided to where stuff over our swimsuits because it might get a bit chilly, especially on the way back to the cabin.

"You'll see," she smiled. "And these better be some HOT springs. I don't want lukewarm or even kinda warm. I'm talking hot."

"Trust me, it is. Even if it was freezing it would feel as hot as a hot tub turned to the max."

"I'll believe it when I feel it." Hailee wouldn't have to wait long. It was a blissfully quick hike to this particular spring.

It was a bit off the regular trail, something my and my dad had kind of claimed for ourselves by accident. I mean of course other people besides from my family had used it, but even they were just members of an exclusive club of people who had managed to just stumble upon it.

When we got there it was visibly hot, steam rising from the water. I dropped my sweatpants, slipped off my sandles, ditched my hoodie and sunk into the hot water. "Oh yeah, told you it was hot."

Almost like she was waiting for that cue, Hailee stripped down herself, revealing a very familiar looking pink bikini.

"But not the hottest thing in the area," I said.

"Nice," she said. "A good and cheesy remark can go a long way." She slowly stepped into the spring, a slight gasp coming from her lips. "Okay, this is hot."

"Too much?"

"Nah, just gotta get used to it." She waded in up to her waste then stopped. "Come here."

"But I'm so comfortable."

"It's much better over here." replied Hailee. I waded toward her, the water going up to my chest. She came closer to me, the water reaching her chest as well.

We were face to face, our hands on each other as if by instinct. Our lips met, softly, but with an intensity behind the kiss.

"If this is you spur of the moment I'm really eager to find out what it's like when you have time to plan," she said.

"Well, I planned a little."

"Still, this is really great. This is way prettier and a lot more soothing than any hot tub or spa. There any spot where we can sit and the water comes up higher?"

"Follow me." I grasped her hand and led her a few steps to a slightly lower rock ledge that served her request perfectly.

"Mmmm, now for one last thing," she said. "Do it it with me...on one...two...three!" She dunked her head under the water and I quickly followed suit. Of course, we were back up shortly after, completely and thoroughly dunked in the hot natural spring water. "Wow that felt good!"

Haille scooted closer to me, resting her head on my shoulder. "So, there's something I want to know about," she said. "It's kind of personal though, so you don't have to answer."

"Um, well, I guess?" I thought I knew where this was going. "I mean I'm not saying Anna and I haven'y had any fun in the past or anything but-"

"Calm down," she smiled. "Look, we're not dating-dating. I mean we're seeing each other but we're not exclusive or anything. Sure, when it's just us...I don't even want another woman to enter your thoughts. But when we're not we can both have fun. I mean, that's what this whole litle vacation is about, right? Having it be just us and see how that works. And it's working GREAT so far. But, you and Anna having some fun? No issue there."

"Okay, so what's the question?"

"Well, and if its too personal no problem, you said thing are good between your parents right now, but how good? Like, if they decide to drop in on us in the cabin for some reason, is it going to be weird?"

"I wouldn't worry about that happening. They're in New York right now. Probably won't be back until the middle of February. As for your question, they're about as good as they can be. I mean my dad has pretty much accepted things as they are. Mainly because I can support myself and have enough left over to invest in my own business and save for a rainy day. Mom on the other hand? She thinks I'm slumming it. I think she knew I had no interest in business stuff. She keeps saying I'm not even doing the entertainment thing to the best of my ability, which oddly enough causes me to half ass it more than anything else..."

"So you half ass it sometimes?" she asked. "I can't tell. But what does it looks like when you're actually trying?"

I reached over and gently held onto Hailee's waist, moving her to my lap, straddling me. "I do believe you're seeing it right now."

"Well, lucky me." She leaned forward to kiss me. "But if you weren't having this little psychological slapfight with your mom, what would you be doing?"

"I don't know...maybe finish one of my movie scripts I guess?"

"You write screenplays?"

"I used to. Mom even liked some of them. But then she just started grating on me more and more and I just kind of stopped. To prove a point I guess."

"Mind if I read one of them?"

"If I find them again, sure. But...how about we stop talking about parental issues and talk about fun things...like all the things we're gonna do in an empty cabin?" I reached down and squeezed Hailee's ass, making her giggle a bit.

"You got it." replied Hailee. "Hope I didn't pry or anything. I was just curious. I mean, if this does get serious, we are probably meeting each other's parents. Just thinking ahead."

"Well, in that case what should I be thinking of with your family?" I asked.

"Well...just be REALLY nice. I mean, you are, and that's why I'm here...but even nicer than that. No offense but I'm 90% percent sure my dad and brother would literally erase you from existence if they thought you were being...untoward with me."

"I'll...keep that in mind."

"You better." She smiled a soft smile at me. "But I think they'll like you just as much as I do...you know, if you even meet them." Haillee got up from my lap and sat next to me once again. "For now...I think I'm just going to soak in everything here. The hot water, the air, the sights..and the company."