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"Up on the Rooftop" with Hailee Steinfeld
Up On The Rooftop
With Hailee Steinfeld
By Harbinger
Codes: MF, oral, blowjob, massage, creampie, kinky, outdoor
Disclaimer: This story is 100% fictional and for fun only. Harbinger makes no money from this.
The condo had all kinds of clientele from your average average couple looking to get away on the lower floors for a few days, all the way to celebrities who would rent out a top floor for the length of a quarantine, or just while they were vacationing.
I was one of many custodians working this building, and we worked floor rotations. One week, I had the top floor. The top floor was one of the worst floors to have because whoever rented the top floor had serious money, which meant they threw serious money or didn't mind paying the fee for making a terrible mess.
However, this particular time I got the top floor, there was only one occupant.
I had gone up to the roof to check on the AC system for the condo, and I didn't realize until I had just finished the repair that I wasn't alone.
"Oh, uh, hello," a sweet young voice said to me before I could see a face. The sun was high in the sky and terribly blinded me, as I had forgotten my sunglasses in another room. "I'm not in your way, am I?" she asked politely.
"Probably not, though I'm a little blinded at the moment," I chuckled.
I heard the lady giggle, and I put down the tool box I held in one hand and the AC filter I had in the other. I covered my eyes with one hand, and I was greeted by none other than Hailee Steinfeld, the star of Hawkeye and the voice of Vi in Arcane, two shows I just recently finished binging.
"Hi there," she said with a cute little wave, as I stood there just staring at the little beauty's perfect body. The California sun made her absolutely glow in the colorful one piece bathing suite she was wearing, no doubt sunbathing at the time.
"Huh… his," I stammered. "I'm so sorry to disturb you, miss. I just had to…."
"No, it's okay," she said, cutting me off before I could explain myself. "You were just doing your job. I'm the one up here just wasting the day away. Can I help you with anything, or are you finished?" I assumed she was mocking me, but her voice sounded so genuine.
"I'm all done, actually. But thanks, I guess."
"Well if you're all done, care to hang out for a bit with me and have a glass of lemonade?" Hailee motioned to her beach chair next to a little white table, which indeed did have a pitcher of lemonade. It looked like one of the kitchenette pitchers from the rooms.
"I really don't want to disturb you, miss, though I appreciate the offer."
"Wow," she laughed. "You're really polite for someone who turned me down twice in two minutes."
I just shrugged, not knowing how to really respond to that. "I'm not really supposed to bug the guests," I lamely explained, rubbing the back of my slightly sunburned neck.
"You're not bugging me if I'm inviting you to spend time with me. I can fill out a complaint card if that'll help."
"That will not help, Ms. Steinfeld," I said, shaking my head.
She smiled, probably because she knew I was caving, and because I knew who she was.
"So what will it be, Bryce?" she asked, reading my name off my shirt tag. "Lemonade with me, or a complaint card saying you were mean and dismissive towards me?"
"Well the lemonade, if you're forcing my hand like that," I chuckled.
"You could use a break, anyway. All hot and sweaty. Mphh!" Hailee bit her lip and looked right at my biceps that were shown off by the half-cut of my work shirt.
Hailee Steinfeld, in all of her sun kissed, tanned and toned glory, was just checking me, a red necked worker out.
"I could take my lunch break now, I guess," I said as she sat down on her long chair, but left plenty of room for me.
"Oh, I'm sorry, I don't have any snacks or anything up here," she said with a real contrite voice.
"You didn't know I'd be up here, obviously. It's totally fine," I told her. I had the hardest time taking my eyes off of her, especially with the way the gentle wind was tossing her hair. "That lemonade does look refreshing. You were smart to bring it up here with you if you were planning to be there for a while."
"I plan to be up here for a while. I don't get this tan by staying inside," she laughed. "Here," she said, getting onto her knees and leaning over the side of the chair to grab another red solo cup. The way she bent over, her chest pressing to the chair, gave me the most exquisite view of her tight ass.
"Fuck," I thought I said in my head, but the way she looked back at me over her shoulder told me she heard it. And she liked it.
"I have a cup for you," she said with a smile, and held it out to me. I reached for it, but she dropped it right into my lap. "Oh my gosh, I didn't know I could be that clumsy," she giggled. She reached for the cup and grazed her knuckles along the inside of my thigh as she picked it up.
"Thank you," I said slowly, making sure I didn't stutter under the gaze of her warm brown eyes.
"Here, let me pour," she offered as she picked up the pitcher with mostly melted ice cubes. "Oh shit, I'm so sorry," she said after some of the sweet and sour liquid missed my cup and hit the front tails of my shirt and soaked my lap. "I have no idea what's wrong with me today!"
"It's fine," I said, a little confused. I get what she was playing at, but why would Hailee Steinfeld play this game with me? I was just, well… me. And she was her. Why was a gorgeous star working to seduce me?
"Let's get that off of you, shall we?" Hailee suggested, putting the lemonade down and reaching forward to unbutton my shirt.
I just sat there, watching her dainty hands expertly undo all of my buttons. Once she popped the last one, she pushed the shirt off of my shoulders, leaving me in a sweaty white tank top.
"Look at those shoulders!" Hailee gushed, rubbing them like she was appraising a piece of meat. "These aren't instagram gym bro shoulders. You're a guy that does honest hard work, huh?"
"Yeah, I guess," I said as I poured myself a cup of the lemonade. "Did you make this?" I asked as I took a long, deep sip. "This is fucking amazing. Pardon my language."
"I did make it!" she beamed proudly, taking a sip herself. "The secret is a little tiny bit of lime, and a few sprigs of mint."
"So it's like a virgin mojito?" I asked as I took another sip. "It's absolutely refreshing."
"I'm so glad you like it," she smiled again and took a sip herself. "So Bryce," she began in a rather serious sounding voice, "while I have you here, how would you feel about helping a girl out with some suntan lotion on her back?"
My eyes widened and I coughed a little around my drink, a bit of it escaping my lips and running down my chin.
Hailee was fearlessly on the hunt and lurched forward, licking the summer drink straight from the column of my neck to the corner of my mouth. My heart completely fucking stopped. "So what do you say?" The hungry, mischievous glint in her eyes said that she already knew I would do anything she'd ask of me.
"Sure," I nodded weakly.
"Okay, cool," she smiled and undid the tie on the back of her swimsuit. She turned her back to me and pulled the top down to her waist. I completely froze in place at the foot of that beach chair, because there was now one half naked Hailee Steinfeld before me, begging me to touch her. "Don't be shy," she giggled.
"You're going to give me a fucking heart attack," I mumbled quietly, but not quietly enough.
"Not yet, I hope," she playfully teased back.
I reached down and grabbed the bottle of oil. I uncapped it and poured some into my hand before applying it to her soft, warm skin.
"Oh, that's nice," she sighed, and wiggled into the chair a bit, her hands covering her tits.
I continued to rub her back, well after the oil had been properly applied. "Your skin is perfect, Hailee," I whispered, and she just hummed.
I let my hands start to wander to her lower back, right to where her bathing suite had been left, and she made no sign of stopping me or even asking me to stop. Hell, she had been trying to seduce me this who;e time.
I went for the oil a second time and worked it in my hands before asking, "Would you like me to do your legs, too?"
"Well yeah," she giggled. "If you see skin, get it oiled," she laughed, and nuzzled into the towel under her head.
As ordered, I worked her legs from toes straight to the bottom of her ass, but didn't dare touch the swell of her ass.
"Hmm, that felt so good," Hailee sighed again. "You have great hands. They're so strong from that work you do," she giggled. "It's a shame I ran out of places I needed oil."
"Fuck, Hailee," I sighed, shaking my head. There was a fucking rager in my stained jeans, and it was starting to hurt a little.
"You want to keep touching me? It's okay. You can," she quietly invited, raising her hips a little as she pulled the bottom of her suit down over her juicy little ass.
I swallowed deep and literally felt my mouth water at the sight of her bare ass. "Hailee…."
"It's not a trap, Bryce. Go ahead, I want you to oil up my ass. Are you telling me you don't want to?" she challenged me.
"Oh fuck it," I gave in. I grabbed the bottle a third time, but now I squirted a copious amount right over Hailee's sweet ass.
I massaged Hailee's glutes for a good few minutes before she bent her leg up and put it right in my lap, her toes feeling around my crotch.
"I bet you're hard as fuck right now," she breathed.
"I'm going to bust through my fucking pants in a minute," I warned her.
"That's your fault for still wearing pants, dude," Hailee openly laughed. "Here, let me help," she said and got up, not trying at all to hide her naked breasts from me.
Hailee reached forward and undid my pants for me. "Now stand up," she ordered, and I did so without hesitation. She pulled my pants and underwear down in one fell swoop, allowing my hard prick to breathe and reach my belly button. "Jesus, look at that thing," Hailee breathed, her eyes wide.
She dipped a few of her fingers into her lemonade and watched a few drops fall and run down my hard length. My breath caught again as she followed them with her tongue, licking the cold beverage right off of my tight skin. She got more lemonade on her fingers and traced the thick veins on my cock before tracing them with her tongue.
"Hailee, I'm going to burst if you keep teasing me like this," I warned her.
"But the lemonade tastes so much better this way," she told me, looking up at me with those eyes of hers from under dark lashes. She took her cup and poured some of it out over the base of my cock, and I had to stop myself from jumping back as she doused my entire length.
To make it up for me, she grabbed me by the balls and worked her tight lips over my length, taking all of me as quick as she could. She moaned around me as she bobbed her head on my cock, taking me a bit deeper every time.
I kept my hands on my hips and had to hold back from thrusting my hips into her mouth. I wanted her to enjoy this, to take the lead and direct. This was Hailee Steinfeld after all, and my cock was hers to command.
It was almost like she could read my mind, because she grabbed my hand and put them on the sides of her head. I took the meaning clearly and wrapped my hands in her hair and began to thrust my hips.
Hailee's moans of "mhmm, mpph!" told me I was following her directions well, and I took it to mean she wanted more. I began to really thrust now, and HAilee grabbed onto my hips as I felt the head of my cock smack the back of her throat. She began to really gag as she got spit logged with her own saliva and my precum.
She was nearly choking by the time I pulled out of her mouth to make sure I didn't prematurely blow my load.
I gave Hailee a moment to recover her breath before I grabbed her legs and put them on the chair. I pushed her down by her exposed chest and made her lie on her back.
I grabbed her suite and pulled off what was still hanging by her side, leaving the starlet completely naked. Her perfectly shaved pussy, wet with arousal and puffy lips under the hot Santa Barbara sun was something to behold.
I took up our reliable lemonade and pound it over her mound, letting it run down over her thighs, cunt, and ass. Once I was satisfied and she was able to catch her breath after the cold liquid's assault, I dropped down and hungrily began licking the sweet drink off of her mound, legs, and finally clamped my mouth over that sweet bald fucking pussy.
I lapped at her folds like a dog drinks from a water dish, and sucked on her hood like I was trying to get a marble out of her twat.
The whole time, Hailee held onto my head for dear life and moaned like a porn star, and I couldn't have cared because we were the only ones on the roof.
Once the delectable taste of lemonade was mostly gone from between her legs, I reached in and spread her soaked lips apart so I could spear my tongue inside of her and properly taste her depths.
"Oh fuck, Bryce! Fuck me with your tongue! I can't to cum into your mouth so fucking bad!" Hailee cried, and I could only smirk into her pink entrance.
To help her make her dream come true, I brought a hand up and easily inserted a finger into Hailee's hot gash before inserting another, making her almost scream as I curled my digits to hit her spongy insides while my tongue punched her swollen clit.
"Fuck! Fuck! Fuck! I'm cumming Bryce, I'm cumming so fucking hard!" Hailee bellowed, her pussy walls fluttering and squeezing around my tongue as she came, her legs trying to crush my head like a grape.
I decided to be merciful and start to ease her out of it with slower thrusts from my hand and gentler licks.
Once she had regained her breathing and stopped running her hands through her now disheveled hair, I got up onto my knees and started stroking my still fully hard cock.
"I am so fucking ready to have that monster inside me," Hailee growled as she pulled her own legs apart for me as far as she could. "Just fucking impale me with that fucker. Give it to me hard and fast. I want the whole city to hear that you're taking me!"
I needed nothing more from the striking brunette. I grabbed my cock, lined it up with her juicy opening, and threw myself down on her, my dick driving in deep as I covered her body with mine.
Her arms were immediately around my back, her nails digging into my flesh as she screamed, "Oh shit! Oh shit that's big! Fuck!"
I winced at the bite of her nails, but her legs wrapped around my waist begged me to plow into her, so I did. I rammed her hard at a break back pace, giving her everything I had, and she took it.
"Oh my God Bryce, I'm seeing fucking stars!" Hailee moaned. She bit my neck and dug her heels into my sides, spurring me on harder.
I hadn't cum yet, and she may have a second time, but I was starting to get winded from my frantic pace, so I rolled us over as smoothly as I could so that Hailee was now riding me.
"I feel like a dropped my pussy onto a fucking chair leg," she groaned as she rocked her hips, happily doing her share of the work as I thrust up into her.
"You feel so fucking good Hailee. This is a million dollar pussy if I've ever had one."
"$10 million pussy," she corrected, and with the way she was riding me, grabbing at her own glistening, oil covered tits, I wasn't going to argue. "But this dick is priceless," she continued. "It's taste, it's length, it's thickness. I want to take you home with me so bad Bryce. I need this dick in me for life."
At this point, I'm not sure Hailee knew what she was saying, but it didn't matter, because she was happy on top of me, and I was getting ready to blow my load.
"Hailee, we're running out of time. Where do you want the shot?" I asked.
"Just fill me up. Unload your balls right into my cervix. I don't fucking care. Just paint my insides!" she panted as she dropped her torso down onto me, allowing us to make out, but also allowing me to thrust up harder into her, my hands playing with her ass cheeks.
I took a huge bet and slid a pinky right into her puckered little asshole that was already lubed with oil and lemonade.
Hailee gasped into my mouth hard as I finger fucked her ass hole and pounded up into her pussy. She came again hard, her walls squeezing so tight it nearly forced my dick out of her, but it was the final push I needed to let go and cum into her.
I thought my eyes were going to explode with the force of my orgasm, and Hailee's inability to draw breath the whole time I came made me think rockets going off dragged her out.
"Oh my fucking God, Bryce," Hailee panted, her head on my chest, her whole body heaving. "I'm so glad we ran into each other like this."
"Me too," I told her as I stroked her hair, my deflating dick still in her. "Me too."
"I'll be here all week, and I bet I'll be up here if you want to keep spending your lunch breaks with me," she offered.
"I'd move into your room for the week if you asked me to," I said only half joking.
"Hopefully you won't be the one cleaning up after we're done," Hailee said with a giggle. "I want you to fuck me in every room of my suite. Starting tonight."
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Imagine if they were next to another skyscraper, those People would have been given quite a show.
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