"Surprise Holiday" with Hailee Steinfeld and Victoria Justice
Surprise Holiday
With Hailee Steinfeld and Victoria Justice
By Harbinger
Tags: M/FF, oral, fingering,
Disclaimer: This story is complete fiction and for entertainment purposes only.
It was just another day for me, Hailee Steinfeld's photographer. It seemed like a never-ending job, usually around the starlet for 10 hours a day. Whether it was candids, actual shoots, getting pictures of her in the makeup chair, the demands were endless. I was her personal shadow, always on hand in case an opportunity presented itself, or was purposefully created.
Fortunately, my boss was actually an incredibly nice and down to earth person. Hailee actually was a sweetheart.
On this fateful day, Hailee was looking particularly smoking as she got ready for a TV interview. I snapped a really nice candid of her just talking to me in the mirror, and it was my most favorite shot I had taken in a long time.
When I had taken that picture, she was telling me about how she felt it was time she took a holiday. What she said next is what made my whole summer.
"Hey, do you want to come with me, Bryan?" Hailee asked, looking at me again via the mirror.
I chuckled a little bit as I lowered my camera. "What?" I felt like I had to double-check.
"I mean it. Do you want to come with me? You deserve a vacation, too. You work your ass off just to make sure you get me at my best. My Instagram doesn't exist without you, practically. You're also a really great friend and listener, and I want to thank you for that," Hailee said sweetly.
"Like, no work, no pictures, just us hanging out?"
"Exactly," she said with a smile, turning to actually face me now. "Just the two of us."
"Yeah, I'm in," I nodded," swallowing deeply. I was going to spend an entire week with Hailee Steinfeld, this genuine, sweet, bombshell of a woman. I don't know what I had just signed up for, but I wasn't going to pass on this surprise Holiday that millions of guys would die to go on.
"Good," she said with a winning smile. "I need a good travel buddy, anyway. Make sure to pack swim trunks."
"Where are you planning on taking us?" I asked, but definitely didn't feel picky. The two of us in bathing suits together was all I really needed to hear.
"You let me worry about that," Hailee teased with a wink.
---
I flew first class for the first time with Hailee, and it was exceptional. Not only were the amenities nice, but Hailee was a great host, being funny, charming, and even dorky at times, endearing herself to me further. She was more of an open book, given that it was a vacation and me not being her employee at this time, as she insisted.
Shamefully, I fell asleep during the last leg of the flight, and woke up to Hailee shaking my leg, her hand on my thigh.
"Hey, Bryan, wake up! We're here," Hailee announced happily. "C'mon, let's get out of here."
Together, we departed the plane, navigated the airport to many looks and murmurs, and managed to get our bags. With a little bit of hassle, We managed to get an Uber to a Hilton Hailee had booked.
Hailee still didn't tell me where we were, but I did see palm trees.
I helped Hailee get her luggage out of the back of the Uber once we got to the hotel, and went to the front desk.
"Hi there. Reservation for Steinfeld. One room, two queen size beds," she said with a friendly chirp to her voice, bit surprisingly enough didn't even sound fake. She just seemed to be in her element, just having fun.
Hailee did the usual legalese b.s. that comes with the stay, and I was surprised to see that we'd be staying for four days. Meanwhile, I just held the luggage until she turned around with a bright smile and key cards
"Let's go check out the room!" she beamed. I pulled my luggage and she insisted that she take hers, because for about the third time so far this trip, "I didn't work for her right now."
Sharing an elevator with Hailee, being so close in that small space, brushing arms with her, smelling her perfume, was intoxicating. I also noticed that she was standing closer to me than usual. It wasn't the first time we had shared an elevator, but it was the first time we'd brushed skin in one.
The door dinged, telling me our little ride was over, and snapping me out of my trance. Our room was on the third floor, and I couldn't wait to see if we had a view, or if we were overlooking a parking lot.
As Hailee opened the door, I couldn't believe how nice the suite was. I didn't want to think about what Hailee paid for it, especially with its large windows overlooking the ocean.
"What do you think?" Hailee asked. Her face had to hurt from how much she was smiling. She went on trips like this all the time, but it was my first experience with a getaway like this.
"It's insane," I said as I walked into the suite that was twice the size of the rooms I was used to. "It's gorgeous, and so big," I said, putting my luggage down.
"I'm glad you like it," she said, sitting on one of the two beds and taking her shoes off. "We're here for four nights, so I'd hate to find out you didn't like it."
"Are you kidding? It's amazing. I feel like a kid," I said as I took in the 52" TV on the wall and the mini bar.
"Are you as excited as I am to see the bathroom, or am I just weird?" Hailee aasked, her socks and shoes now forgotten, her little toes with red painted nails running through the soft carpet.
"Oh no, the bathroom can definitely make or break a room," I said, following her.
Hailee opened another door in the room and flicked the light on, illuminating a beautiful large bathroom mirror with lights around it, but also a full shower with sliding glass door and a jacuzzi.
"Oh no, this place is sweet. I really was hoping the pictures didn't oversell it, but they were right on the money."
"Can I ask how…" she cut me off by flicking my forehead, which she really had to reach for, the adorkableness coming through again.
"No, Bryan. You're on vacation, too. No questions about money. Believe me when I tell you, I can afford it, you sweet giant," Hailee giggled.
Hailee was borderline flirty, but it was also the most relaxed I had ever seen her, so I just chalked it up to that. And the giant comment wasn't a miss. While Hailee was a pretty tall girl at being 5'8, I was pretty big myself, coming in at 6'7.
"We should take turns with the shower and then let's go check out the restaurant on the first floor for lunch?" Hailee suggested, and I just nodded.
"Sounds great," I said. "Who should go first?"
"Can I go first? I'm going to wash my hair, so I'll need the extra time to dry it."
"Yeah, that's cool," I said without a fight, lying back in bed while she dug through one of her roll-around cases for clean clothes. "Let me know how the shower head is."
"You bet," Hailee said as she re-zipped her case and strolled into the bathroom, closing the door behind her.
I listened to a couple chat in the hallway for a second, and then I listened to the silence, knowing the famous singer and movie star Hailee Steinfeld was just one room away, stripping down to her birthday suit and about to enjoy a hot shower, her body soaking wet and drops of steamy water pouring down her curves.
I was already hard, and I felt terrible, but human. This nice girl was giving me an all expense paid vacation, and I was having horny thoughts as she innocently showered.
I heard the water kick on, and I actively tried to think about anything else.
It was a losing battle, hearing the water and knowing what was happening in there, so I tried to distract myself with the TV. The closest thing to interesting I could find was River Monsters with Jeremy Wade.
Finally, the door opened and Hailee came out in a pair of black leggings and a sporty tanktop, a towel coned around her head.
"Sorry you're seeing me this domestic," Hailee said as she sat on the foot of the bed across from me.
"It's cool. We're on vacation, remember?" I joked and she smiled over at me.
"Now you're getting it," she laughed, twisted at the waist and extending one of her long, toned legs to playfully kick me. "Now go shower so we can go get lunch. I'm starving over here."
"Models actually eat?" I mocked as I picked out my clothes.
"It takes a lot of food to keep this body looking like this," she said, motioning up and down her fit core. She definitely had a right to model gym gear and be the girl for Core water. Her body was banging and not walkway thin, having real arms and really nice shoulders.
When I came out of the shower a few minutes later, Hailee hadn't changed except for her towel was gone. I stole a quick glance to the bathroom I had left open and saw she had hung it back up.
The dirty little minx had replaced it while I was in there! She looked completely innocent just watching TV, pretending she hadn't stolen a glance at my naked, fogged up silhouette.
I shook it off and asked, "Are we going to lunch?"
"Yep!" she said, smiling at my t-shirt and basketball shorts. We were just slumming it on vacation, after all. "You look comfy. I like it."
Hailee and I were just about to be seated in the hotel's restaurant, a nice little Cajun place, when we heard a woman's voice say, "Well there's just no way!"
Hailee stopped, and her jaw dropped. "Victoria? I haven't seen you in… God, I don't want to think about it!" Hailee gushed as I turned over to see yet another drop-dead gorgeous celeb, Victoria Justice.
"What are the chances?" Victoria beamed as she left her table and came to hug her taller friend before exchanging kisses to the cheeks. "You two have to join me," Victoria insisted.
Hailee and I took up chairs at Victoria's table, the waiter leaving us menus and looking a little shell shocked. Hailee was casually gorgeous and Victoria looked sinfully delicious in jean shorts and an orange sleeveless top tucked into her shorts with daringly open sides.
"And who might you be?" Victoria asked me as she took a sip of her white wine. She apparently didn't care that it was only 2 p.m.
"This is my friend Bryan. We're vacationing here for four nights. Bryan, this is Victoria Justice, but I think you know that," Hailee introduced.
"You took your friend Bryan on a romantic four night getaway? That's super nice of you," Victoria teased.
"Dude, shut up," Hailee almost hissed, covering her face in her hands.
"Hailee, what's going on?" I asked, feeling like something was up.
"Alright, fine," Hailee huffed. She was absolutely adorable when perplexed. "This was supposed to be for me and my boyfriend, but we split up and I wasn't going to miss this because he's a fucker. I changed the room to have two beds instead of one last minute. I hope you're not mad," she said, her hand on mine.
"No. His loss and my gain of a sweet vacation," I shrugged.
"Atta boy," Victoria smiled. "And now we get to hang out. I won't feel like a third wheel since you and Hailee aren't exclusive."
"Are you cool with that, Bryan?" Hailee asked hopefully.
"Yeah, it's a hell of a deal," I laughed. What kind of guy would turn that down?"
The three of us shared a pleasant lunch together, and then discussed plans for after it.
"What do you guys think about a beach day?" Hailee asked as she finished her drink.
"You know I love the beach," Victoria smiled, and then turned to me. "What do think about a beach day with me and Hailee, Bryan?" She sounded like she thought I might actually say no, but there was no way I was passing up on this.
"Yeah, I'm down for that. Lead the way," I painlessly agreed.
As we left the restaurant, Hailee asked, "V, how long are you staying?"
Victoria pouted and said, "My flight is at 9 p.m. tonight. Gross, I know."
"Bryan, do you have a moment?" Hailee asked me, looking up.
"Uh, yeah," I said, and the brunette firecracker pulled me aside by the hand.
"You know, we do have two beds, and that room is huge. What if we had a slumber party?" Hailee whispered, making sure the Latina in question couldn't hear us. "She can share my bed and it won't be weird because we're girls."
"Uh, yeah. If you both are comfortable, I'm cool with it. I'm just here for the ride, essentially."
"I want you to have a good time, too, though. I promise this week won't turn into being all about Victoria," Hailee promised.
"We're fine. I'm not worried about it. For real," I said. This was not a pulling teeth situation.
"Okay, you're the best," Hailee smiled, squeezing my hand before pulling me back over to the waiting Victoria.
"Ready to go?" Victoria asked. "I can meet you guys back here, or we can meet up in your room?"
"Would you be interested in rescheduling your flight and staying with us? At least for the night, see how it goes?" Hailee offered.
"Oh, yeah, uh, sure!" Victoria stammered, caught off guard by the offer. "The front desk was nice enough to hide my stuff in the back, so let me grab that and I'll head up with you guys."
We got Victoria Justice easily moved in with us for at least part of our weekend, and then we got ready for our beach day.
I wore simply swim trunks and a muscle shirt, and the girls changed in the main room while I got dressed in the bathroom.
"You can come out, Bryan!" Hailee called and I rejoined the girls, both looking mouthwatering. Hailee wore a cute baby blue two piece and Victoria had a pastel green two piece. Both girls had the bodies to just go out in the tops and jean shorts until we got to our beach location.
We didn't have to wait long for an Uber to grab us, and the poor guy damn near forgot how to drive with those two girls in the back seat.
Victoria had a "private beach" she wanted us to check out, so she gave the distracted driver directions more than an actual address to use.
Once we left the Uber, we had about a half mile walk down a scenic path, down a short sandy embankment, and then on a beautiful, absolutely deserted beach.
"V, this is gorgeous," Hailee said in awe at the photoshoot worthy beach as she set her bag and towel down.
I was a professional photographer because I was a passion photographer first, so of course I had a small camera with me. I took a landscape shot of the crystal blue water, the nearly white sand and the green trees on the opposite bank of the small lake.
"Bryan, take a picture of me!" Victoria called, and I spun around towards her voice and took the shot like some kind of trick archer. It was a phenomenal picture of Victoria looking into the camera with a sexy smolder, bent over and peeling her tight jean shorts down. I took a few pics of her modeling her outfit, before turning my camera on Hailee.
The shots I took of Hailee were more candid, and every bit as sexy. The tall brunette was leaning against a tree as she slid her jean shorts down her toned thighs, her bikini bottoms looking like they wanted to come off with them. The shots I took after were of her digging her toes in the sand, stretching her arms to feel the cool breeze, and closing her eyes and tilting her head back to smell the ocean.
"God, Hailee’s a beautiful girl, isn't she?" Victoria whispered in my ear, her fingers grazing down my back. "I think she likes you, too," she teased.
I shook my head and laughed. "Nah, I think we're just friends," I said in denial, knowing it would be naive and stupid for me to get my hopes up for more than a friendship.
"Bryan, buddy, that's Hailee Steinfeld. She could have brought anyone on this vacation, and though I don't see her very often, we talk a lot. She's going to get some dick on this trip… and she chose to bring yours. It's just a bonus you two have actual chemistry. Just think about it."
The three of us played in the surf for what felt like hours, laughing and splashing, dunking each other and playfully wrestling, swimming and having a genuinely good time.
When we got tired, we decided to lay out on the beach and let the sun dry us. Once we were dry, Hailee insisted we should all tan while we were there.
She oiled me up first, and then Victoria suggested I oil up both of them, to which Hailee agreed with a smile and I ended up with an erection before I had even finished oiling Hailee, let alone when I had oiled up Victoria, too.
I tried to hide it, but Victoria said, "We know we're attractive, and we did just have you put your hands all over us."
"It is perfectly natural, Bryan. It's just us, anyway," Hailee added.
That was about a half hour ago, and Hailee had since then fallen asleep.
Victoria and I were still awake, quietly talking so we didn't wake up the tired girl next to me.
She sat up and stripped out of her top and started rubbing more of the coconut scented oil on her perfect tits.
"You can look, Bryan, it's okay," Victoria said teasingly. "Like Hailee said, it's just us."
With her encouragement, I turned my head to see a smiling VJ looking back at me, palming her gorgeous breasts.
"Do you want to see my breasts, Bryan? In person, all covered in oil and not just some internet leaks?"
"Yeah, I do," I gave in.
"I'll show you them, but I need you to do something for me, too. I want you to lick Hailee's pussy while she's sleeping."
My eyes almost popped out of my head. "What? Are you serious?"
"100 percent," Victoria nodded, still massaging her boobs and playing with her hardening nipples. "All three of us will be glad you did. I promise. Here, I'll get you started," she said as she stood up, dropping her arms and letting me see her medium sized tits with delicious brown nipples.
She dug her knees in the sand and wrested her elbows on the bottom of Hailee's towel. As if she had done it a million times before, Victoria pulled the gusset of Hailee's bottoms to the side and licked her from asshole to the top of her pussy.
Victoria repeated it two more times at a casual but not tortuous speed before getting back to her knees, the towel having saved her tits from getting covered in sand. "There, your turn," Victoria said, motioning a hand to the still sleeping Marvel actress.
I traded spots with Victoria, took in a deep breath, and did as she had, leaving Hailee's bottoms on but giving myself access to the cutest peach ai had ever seen.
I went for it and followed Victoria's path, hitting rosebud, puffy lips, and finally veiled clit. I watched the sleeping beauty from between her legs. She'd occasionally shift, but the arm draped over her eyes told me she was still deeply stumbling.
I continued to lick Hailee good, and occasionally she'd let out a small, satisfied hum.
"I bet she's dreaming about you eating her out," Victoria teased, still playing with her own breasts, but now focusing more heavily on her nipples and less on hiding them.
"Bryan, oh my God," Hailee mumbled, her head gently rolling to the side. "So good."
"See, I told you!" VJ said with a victorious smile. "She loves it!"
I had gone this far and decided to further press my luck by carefully, slowly inserting a finger into Hailee's tight hole.
"Oh yeah, there we go," Victoria coached as she scooted up and started palming Hailee's medium sized chest. "Her nipples are hardening," she reported.
I smiled into Hailee's pussy at that information as I continued to probe and lick the tall brunette.
"Uh, oh yeah," Hailee moaned and started to stir. "Oh my God, Bryan."
I continued to flick her newly exposed clit and started to slide my finger in and out of her easier as her natural lubrication helped me along.
"Huh? What… what's happening? Guys?" Hailee asked in foggy confusion as she actually woke up.
"Shhhh, it's okay. Just lay back and enjoy it. You're on Vacation," Victoria said with a smile as she massaged Hailee's tits with both hands.
Hailee looked down and saw me eating and fingering her, her jaw dropping open. "Bryan, holy shit!" Hailee moaned. "Fuck, your mouth feels good. And V, your hands…" Hailee cooed in lust as she subjected herself to it.
"That's a good girl," the Latina minx smiled as she pulled down the front of Hailee's top, letting her glorious tits spill out. "We need some oil on the girls," Victoria insisted as she poured a copious amount on her and happily smeared it across Hailee's chest.
"Jesus Christ," Hailee moaned as I kept pleasuring her and Victoria mauled her chest with her hands. "This is… ah! Just what I… mphhh… needed!"
I pulled my mouth off of Hailee's snatch and added a second finger, a big smile on my face. "You and I both," I laughed.
"Oh my God, your fingers are so big!" Hailee groaned as she clenched the sides of her large beach towel with her hands. She dared not stop Victoria from playing with her nipples.
Victoria shifted her position and straddled Hailee ribs. "Kiss my tits, Hailee. I bet they taste like coconut," Victoria said. I looked up and saw the back of her legs and her gorgeous ass, but I could hear the smile on her face.
With Hailee fully awake and not fighting us, I was happy to increase my fingering speed and start using my tongue more daringly.
"They do taste like coconut," I heard Hailee giggle, followed by Victoria sighing.
With Hailee busy and unable to see what I was doing, I decided it was time to bring it home. I pulled off my swim trunks, freeing my hard erection as I listened to the sound of Hailee and VJ swapping spit.
I pulled up on Hailee's hips, giving myself a better angle.
"V, what's Bryan doing?" Hailee asked, short of breath.
VJ turned over her shoulder and smiled, watching me rubbing my hard cock with Hailee's juices on my fingers.
"Do you want to know?" Victoria teased.
"Yes," Hailee confirmed with baited breath.
"Well, he has his cock in his hand. He's stroking it, he has it aimed right at that hot, tight and wet cunt of yours. He's going to fuck your brains out, Hailee."
"FUCK!" the Spiderverse star shouted as I pushed in, sinking all the way in with a measured thrust.
I didn't start off slow. I fucking gave it to her, with my hands groping her firm ass and Victoria still on top of her, holding her down.
"Oh my God, Bryan! Your cock is so big!" she complained and squirmed, but had no where to run.
"The man is huge, what did you expect?" Victoria laughed as I fucked her friend good and hard.
"Oh my God, oh my God, oh my God!" Hailee chanted as I pounded away at her.
Victoria stood up long enough to drop her bottoms, leaving her completely naked. She settled back down, her knees on either side of Hailee's head.
"I'm on vacation too, and I want a good orgasm," she sternly informed Hailee before dropping her perfectly shaved muff onto Hailee's gasping mouth.
Hailee grabbed V's athletic hips and dug into that sweet Puerto Rican gash and started eating like she was starving.
"Oh, holy shit! This girl is good!" Victoria laughed as she began to buck her hips and ride Hailee's skilled mouth, reaching back to rub Hailee's clit. The sensation and the whole scenario caused Hailee to scream into Victoria's snatch as her orgasm rushed her.
"Jesus Christ!" I chuckled as Hailee's contracting vaginal walls tried to forcefully eject me. Hailee was my favorite pussy, but not the only one I ever had, so I timed my thrusts between her contractions, still fucking her hard and fast like a game of Red Light Green Light.
"Bryan, please… I'm so… fuck! Overstimmed!" Hailee begged for a ceasefire.
I respected my hostesses wishes, and pulled out as abruptly as I had entered her, making her gasp yet again.
Without warning, I grabbed a handful of Victoria's long dark hair and athletic hip, pulling her down Hailee's body and I filled her up with my length while Hailee recovered.
"Jesus, Bryan, ask a girl first!" Victoria berated me. Given the way she instantly started throwing hip to fuck me back, there was no love actually lost.
"This was all your idea," I huffed back as I fucked Victoria's tight cunt as hard as I had fucked Hailee.
"How's that huge white cock of his feel?" Hailee teased, licking her hand and reaching down to rub Victoria's clit. "You're smaller than I am," she laughed.
"Fuck does it ever feel good!" Victoria said as she pushed back into my every thrust. "It's what a real cock should feel like."
"So I have you to thank for getting this ball rolling?" Hailee asked as her arm pistoned back and forth to help bring Victoria a much needed release.
"Yes. I encouraged it," Victoria admitted as she sucked on slobbering on Hailee's recently oiled tits, enjoying the edible coconut oil she had picked. It made me wonder if she had planned something like this.
"I'll make sure you get rewarded for it later, but I need Bryan's cum right now," Hailee said, shifting down and pulling me out of Victoria's pussy to aim me back at hers, and without messing up my tempo, I slid right back into Hailee's heat.
"God, you both are so fucking good," I growled as I pummeled the Arcane star's innards again, making Victoria whine.
With Victoria now free, Hailee grabbed the singer and actress under her arms and pulled her up, allowing them to share a deep kiss.
"Fuck, I can taste my pussy on your tongue," Victoria sighed as they continued to almost forcefully make out, and Hailee's hand back between them, making sure Victoria's nethers weren't neglected.
I was finally at my breaking point, having had both of these sensational that's on my cock, and watching two of the most gorgeous girls on the planet defile each other.
"I've decided you've both earned this," I announced as I slipped out of Hailee's wetness, jacked myself off for an entirety of 15 seconds, and blew my massive load all over Victoria's pert ass and inner thighs, and Hailee's pussy, thighs, and shaved public mound.
"Well fuck, Bryan!" Victoria complained. "If you would have said something, we could have gotten on our knees and you could have cum on these faces," she said, pointing to both of them in turn.
"I did what I thought was right in the moment," I shrugged.
"He'll have another chance when we get back to our room," Hailee said as she used her fingers to gather my cum off Victoria's ass and bring it ro her mouth.
"You're right, Hailee. There will be more chances if I stretch my holiday a little further," Victoria winked.
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