Hailee's Yours

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A great day with Hailee Steinfeld ends even better.
4.6k words
4.42
8.4k
13

Part 1 of the 3 part series

Updated 01/21/2024
Created 01/03/2024
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Disclaimer: This story is a work of fiction. I do not know any of the real-life people involved. This is a fantasy.

You awoke with an annoyed groan due to both the sunlight from the window and the sound of a hair dryer blowing at full speed from the bathroom. You reached for the dresser next to the king-sized bed and took a sip of water to clear your throat. You ran your fingers through your hair and cracked your back.

"Morning sleepyhead," Your girlfriend, Hailee Steinfeld, walked out of the bathroom with a towel wrapped around her body. Her wet hair clung to her neck and back, causing small water droplets to fall between her cleavage. She smiled, sat on the bed next to you, and kissed your cheek. "I thought you'd never wake up." She said while lovingly rubbing your back.

"It's not that late." You looked at the clock, honestly surprised by the time.

"It's 10:34 babe." She kissed you square on the lips. Her beautiful face was just scrubbed and washed. You could tell she'd just applied a layer or two of lotion, but other than that she was makeup-free. Natural and cute. You'd been staring a bit too long, causing her smile to fade into a goofy frown.

"Get up," Hailee playfully smacked your leg. "We've got things to do this afternoon." She stood up and walked back to the bathroom.

"We?"

"Yes. You're not working tonight are you?"

"No." You answered. You worked two jobs. A part-time taxi driver and a security guard for the uber-rich. The taxi job was actually where you met Hailee. She'd hailed for you after answering a few questions from the paparazzi outside of some fancy restaurant whose name you could never pronounce. She was wearing a simple black long-sleeved off-the-shoulder dress with matching black pumps and golden hoop earrings. Her makeup highlighted every ounce of her beauty without hiding anything.

She was really easy to talk to and you made her laugh with your wild bodyguard stories. She wrote her number on one of the fifties she'd tipped you and you joked that you were going to frame it. From then on, you two had been dating. Making her laugh was the best feeling in the world.

You tugged at your growing cock that was tucked away in your boxers. She stood in front of the mirror still blow-drying her hair. She worked her arms hard, causing the towel to fall slightly, exposing more of her lovely chest. You two had only been dating for a month and a half. You and Hailee fooled around a few times, usually when lazily cuddling on the couch, but never full-on penetration. She'd always requested that the moment should be perfect. That didn't mean you couldn't at least get a piece.

You snuck into the bathroom with your hard cock in your hand. You were to her left and she was looking down at her phone so you slipped next to her unnoticed.

"Oh!" Hailee jumped when you slid your hand around her waist and kissed her shoulder.

"We can't. I have somewhere to be in an hour."

"Really?" You groaned while moving your kisses up to her neck. She smiled and tilted her head into it.

"Yes, and by the time I get back we'll have to be ready." Hailee ran her soft hand through your hair. She certainly wasn't fighting back.

"What kind of party is it?" You asked while your hands crept to her tight ass.

"It's just a sponsor thing- mmmhh..." She moaned when you gripped her left cheek. Soft and plump through the towel. Making her laugh was great, but making her moan was even better.

"Why do I have to be there? I thought you didn't want me in the scene." You asked. From the first day you started dating, she'd always wanted you out of the public eye. She was very adamant about keeping you private. All to herself as she would say.

"I want you there because I like you." Hailee answered, her voice husky.

"You want me to, but you don't need me to."

"Do you really want to stay here? It's going to be a while until I get back." Hailee explained.

"Do you want me to watch you stand around, as gorgeous as you are, and stay away? Or should we make this relationship public?" You stopped your kisses, but you kept her shuddering with your hot breath against her neck and your hand on her ass.

"You don't want that... believe me."

"Why? I'd want people to see me appreciate your beauty."

"They'll think I'm dating some nobody. Not that I care, but I don't want you to be hounded or stalked."

"When I'm with you I'm somebody."

Hailee smiled and kissed you. She turned away from your grasp and unwrapped her towel. She let it fall to the floor, revealing her incredible body. She reached forward to grab your boxers and pulled them down, freeing your long and hard cock. Hailee's face lit up as she held your throbbing cock in her soft hands.

"I thought you said you have to be somewhere in an hour?" You said, smirking.

"Since you've been such a good boy," Hailee dropped to her knees. "I can push it back a bit."

Hailee smooched the head of your cock before taking you all the way in the back of her throat. Her nose was buried in your pubes and her face was red. The warmth of her throat and the feeling of her tongue running over your shaft nearly sent you over the edge right then and there.

"Oh..." You braced yourself with one hand on the counter. "That's so good..."

Hailee pulled off with a nasty slurping sound and laughed. A loving laugh, but still teasing.

"What?"

"Your face," Hailee calmed herself down. Her face changed to the look of the gorgeous seductress that she was. "You love it when I go all the way don't you?" Hailee said before sucking the saliva off the side of your shaft. Tiny drops of spit landed on her plump tits and slender thighs.

"Don't forget the balls, baby." You groaned while reaching down to cup her left tit.

"I never forget," Hailee kissed your nutsack. "Big and full for me everytime." She then wrapped her wet lips around your balls and juggled them in her mouth. She sucked on your balls and stroked your throbbing cock with loving passion. After half a minute of ball sucking she returned to your cock. She deepthroated you while rocking back and forth on the floor.

Hailee grabbed the base with both hands to stroke and suck at the same time. Her eyes were wide and full of want. She wanted to make you explode in her hot mouth and all over her beautiful face. Thicker trails of slime fell down her chin, slathering her chest in drool. She pulled off your cock, smiled, and ran her tongue around the sensitive head. That broke the dam.

"Oh shit!" You yelped. Long ropes of warm seed blasted her plump lips and forehead. You fired at least ten shots into her face and five more into her mouth. Hailee sucked more of your sticky seed off your softening cock, her lips curled into a goofy grin.

"Mmmhh..." Hailee rubbed your seed into her skin while licking up the mess on her lips. More drops of cream fell down her face and stained the bathroom floor.

"That was great, babe." You grabbed a nearby towel and handed it to her. She wiped away the semen and spit.

"I might have to call my agent and tell her I'm not feeling so hot." Hailee stood up and wrapped you in a hug. Your cock stirred from her soft breasts pushing against your body. Hailee kissed along the underside of your jaw while rubbing your stomach.

"I'll go." You kissed her forehead. You figured that if you went with her and simply stayed out the way, after the party that'd be the perfect moment. The moment to finally be inside of her.

"Thanks babe," She broke the hug and put her towel back on. You admired her ass when she bent down to pick it up and from the sly smirk on her face, you could tell she noticed.

"Now take a shower. I'm going to get dressed. I'll be back in a few hours." Hailee kissed you and playfully swatted your ass.

"Be safe, babe."

*

You'd taken a long shower, checked your emails, and watched a movie while waiting for Hailee. Boredom slowly began to set in. You hoped that she'd wear something revealing, but your cock really stirred at the thought of fucking Hailee's brains out at the party. Obviously, she didn't mean anything by the nobody comment, and you meant it when you said you felt like somebody with her, but if you could let the world know that you were the random who had Hailee Steinfeld on her knees then you'd really be somebody.

As you daydreamed, Hailee finally came back home with a smile on her face. You got off the couch and tucked your erection between your legs.

"Hey babe!" She dropped her bags and hugged you tight. Her hair was tied back into a bun with a few loose strands falling down her face. She was wearing a simple white tank top and snug black jeans that clung to her nice and tight. You caught a whiff of her sweet lotion and your erection immediately sprouted out from its hiding spot.

"When do we leave?"

"Uhh," Hailee broke the hug and checked her phone. The clock read 3:26 pm. "We'll want to leave at five. Five-fifteen at the latest. Gives us time to eat and relax for a bit."

You both ate in silence, sneaking flirty glances at one another without having to share a word. You chowed down the real food like it was your first meal in days. You'd finished before she even started to set up her bowl. You just stared at her while she was stirring, getting lost in her perfect features.

"So," She snapped you out of your trance. "I was thinking that you should just wear a regular suit. It's just a glorified photo set for Instagram. It shouldn't take too long."

"That's good." You smiled to yourself. Tonight was going to be the night. It had to be.

"Why? You got plans?"

"Well..." You trailed off and began to blush like a little boy around his crush. The way she looked at you certainly didn't help.

"Hello? I asked if you've got any plans?"

"Nothing. I was just curious." You answered, unable to stop your lips from curling.

"Then why are you smiling?" Hailee smirked back.

"I'm here with you. I got a full belly and an empty nutsack." You brushed her hand from across the table. Hailee started up another adorable laughing fit at your comment. Her breasts jiggled beneath the thin fabric of her top, giving you an opportunity to change the subject when she finally calmed down.

"Are you wearing a bra?"

"Nope. Why? You've been looking at my tits?"

"Yes." You admitted. It was better than telling her that you wanted to fuck her right now.

"You dirty dog. Didn't you just say you had an empty nutsack?" Hailee giggled.

"Well it has been a few hours."

"You're not getting another blowjob. Not today." Hailee finished her bowl. You grabbed her things and threw them in the trash can inside the counter next to the sink. She came up behind you and kissed your back.

"Let's get ready, babe." Hailee sighed.

"Alright. I'll see if I can find my special suit."

You followed Hailee upstairs, watching her ass sway as she slowly walked up the steps. She was definitely teasing. At least you hoped she was. Sometimes you wondered if she knew the difference between torture and teasing. You both went into the main living room and you tried to stay out of her way while finding your clothes.

You decided to wear a black dress shirt with matching pants and shoes, topped off with a dark green suit jacket. It was the suit you wore when you and Hailee went out on your first official date. The only thing that was missing was your cufflinks. You sat on the edge of the bed, smoothing out your pants, until Hailee stepped out of the walk-in closet to the right side of you in a lacy white bra and panties.

"Hey babe."

"Hey." You stared at those creamy legs.

"Should I wear something casual or something a little more... let's just say showy?"

"I'll uh..." You swallowed to clear the lump in your throat. "I'll have to see the choices."

"Oh really?" Hailee smiled and made her way back into the closet.

"Do you want to see the casual outfit first?" Hailee shouted.

"Sure." You answered.

After a few minutes, Hailee stepped out in a button-up denim blouse with a high-slit maxi skirt. The cut was like a peek into the infinite beauty behind the fabric. She spun around dramatically to give you a full view.

"I like it."

"I like it too, but," Hailee looked you up and down, biting her bottom lip. She was so goddamn sexy it hurt. "It doesn't really match what you have."

"I can change. Do you need me to?"

"No, it's fine. I'll see if I have something that matches that."

"I thought you said I was supposed to stay out of the public eye?"

"It'd still be cute if we matched, dear." Hailee smiled before stepping back into the closet.

You shifted around on the bed to get your erection that was stuffed into the side of your underwear against your left thigh. After five minutes of waiting, Hailee came out in her second outfit, if you could even call it an outfit. She wore a white cropped tank top that ended right at the lower curve of her braless breasts, teasing her underboob and flat stomach. Next was an incredibly short black skirt, no slit was necessary. The end of the skirt rested against the bottom slope of her asscheeks. If she jumped, everyone would get a show.

"That's really something, but I thought you wanted to match." You said while trying to sneak a peek under her skirt.

"Shoot! You're right. I got a little too excited," Hailee turned her head to the side. "That tormentor down there got excited too huh?" She laughed at her own joke and you couldn't help but laugh with her. She went back inside and came back with a cropped blazer that matched your suit's deep green.

"There we go!" Hailee spread her arms, doing a little dance for you. The way her body moved in that outfit sent a chill down your spine. She shuffled closer and sat in your lap, wrapping her arms around your neck, and gently kissing your nose.

"You look beautiful." You kissed her back with your arms wrapped around her waist. Hailee grabbed your arm to stop you from getting too handsy.

"We have to make it to the party, love." Hailee crawled off of your lap and readjusted her jacket.

"Alright. Let's go." You sighed. The warmth of her bare pussy against your legs nearly sent you over the edge. It was going to be a long next few hours.

As you drove to the address Hailee marked into the GPS system, you noticed that she kept staring at you from the passenger seat with an odd look in her eyes.

"What's up?" You asked.

"Just thinking." Hailee answered.

"About me?"

"Maybe. Maybe not." She winked. "You got any more questions?"

"I don't know. You gonna keep staring?" You asked.

"You look too good for me to not enjoy the view." Hailee spread her legs and you could've sworn you caught a glimpse of her pussy in the streetlights from the corner of your eye.

"I think the same thing about you, y'know. Unfortunately I have to focus on the road." You looked down at the GPS. Fifteen more minutes.

"That's really sweet," Hailee blushed. "I'm glad I met you. It's kind of difficult to find people who are down to earth around here. Especially when dating."

"What do you mean?" You knew she'd dated other guys, but neither you nor she brought up your past relationships. You didn't want to pry, but she was gorgeous and smart. Whoever let her go had to be a moron. You didn't want to make that mistake. Ever.

"It's just... it's an ego thing. It's not just them, even I have my head up my ass sometimes. Our schedules clash ninety-nine percent of the time and when separated we begin to think we don't need each other." Hailee explained.

"I see." A quick twinge of fear went through you. She did work a lot and you usually worked at night.

"When we do have time with each other, it usually ends in an argument. You're probably wondering why I even bother with dating when I'm this busy, but it does get lonely."

"I'm sorry."

"Nah don't worry," Hailee leaned to the side to kiss you on the cheek. "I found you."

You weren't going to let her slip through the cracks. After the party, you were going to send her over the fucking moon. She was never going to forget you after tonight, you were sure of it.

When you eventually pulled up to the party, Hailee dug through the glovebox and handed you a pair of sunglasses.

"Why sunglasses?"

"You're my bodyguard for tonight. That's how you can be right next to me without people assuming things." Hailee explained.

"We're matching. That's something couples usually do.

"Maybe I want my bodyguard to stand out. In more ways than one." Hailee quipped while pointing at your cock. You were at least half hard the entire ride.

"I'll try to keep it down."

Hailee kissed you and rubbed your shoulders.

"Good. Let's get this over with." Hailee opened the door and you gave your keys to the valet before putting on the sunglasses. Hailee walked in front of you, every step sending her skirt up giving you a great view of her perfect pale ass bouncing in the wind. Still no panties.

"Hailee, this seems a little dangerous." You whispered to her. She turned around while suggestively biting her lip. Her skirt spun again.

"Why? If anyone tries anything you step in, Mr Bodyguard." Hailee walked backward, the cool breeze hardened her nipples.

"How do you expect me to stay soft?"

"You're a professional. Don't act like you haven't looked after some beautiful women during your job, and they probably wanted to fuck you in front of their husbands."

"You make a good point. Just try not to flash the cameramen."

"Oh please. You're the only one who'll get this."

You almost froze up at that comment. Once again, you hoped she knew the difference between teasing and torture. As both of you entered the fancy ballroom, you immediately noticed all of the eyes in the room were immediately on Hailee. She smiled and waved, greeting those near her and flashing bright smiles to everyone with cameras.

You stood back and watched. While the other women in the building were pretty, none of them compared to Hailee. She continued to mingle and take pictures, but she never left your sight. Somehow during all of the handshakes and hugs, her skirt never flew up. Some media members definitely wanted upskirts, but Hailee strategically avoided them by constantly moving around the room. After at least half an hour the crowd grew and you couldn't see her anymore.

You moved along the corners of the room until you eventually found her chatting with a beautiful brunette in an off-the-shoulder red dress. She was slightly shorter than Hailee, but her tits were insane. They were nearly bursting out of her top. Hailee and the blonde chatted for a few more minutes, but the music and the chatter of the event overpowered the ladies' friendly conversation.

You stood to their side, still eyeing Hailee's ass and the brunette's tits. Out of the corner of your eye, you saw the two girls walking towards you.

"Sydney, I want you to meet my bodyguard." Hailee introduced you. You finally recognized her when she was up close. You held out your hand for a handshake, but Sydney went in for a hug. Her soft tits pressed against your body. She held onto the hug for a few more seconds than was necessary, but Hailee looked fine with it. She was actually smiling at you.

"Hello, ma'am." You said after she broke the hug.

"I see you've got a nice job," Sydney said. She just oozed grace and confidence just from her facial expressions.

"You get to look at her all day." Sydney wrapped her arm around Hailee's shoulder. Both girls giggled at each other.

"It's harder than it seems, Miss." You said after awkwardly clearing your throat. Both of these women were Hollywood royalty. One of them was your girlfriend, and the other was openly checking you out.

"Well," Sydney hugged Hailee and brushed her perfect hair from her face. "I should be on my way."

"Alright Sydney. I'll be seeing you." Hailee hugged back. Sydney turned to you with a big smile on her face.

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