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Thread: Celebrating the Holidays at a Poolside Paradise w/ Hailee Steinfeld

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    fanfiction Celebrating the Holidays at a Poolside Paradise w/ Hailee Steinfeld

    Celebrating the Holidays at a Poolside Paradise
    Starring Hailee Steinfeld
    Codes: MF, Public (Maybe slightly NC-to-Con)
    Disclaimer: The following is completely fiction and pure fantasy
    This is also a one time story and unlike my previous stories it has no ties to the Lucky Bastard series.






    Shane was now a 28 year old guy living life in the snowy Miniapolis, and after his father passed away two years ago and his mother three years before that, Shane had decided to treat himself. Rather than go home to Indiana for for Christmas with his stepmom and step brothers, he decided that he would splurge and go to a big fancy resort in Hawaii. His stepmom had laid on a serious guilt trip when he told her of his plans, but he was able to get through it. He had now been in Hawaii for two days and he had gotten to know his way around the resort pretty well. The room was good size with a very comfortable bed and a balcony looking a large green area, there were a couple of restaurants, and other than the beach there was also three pools. Shane's issue was that all he wanted was a nice quiet place to relax in the sun and read his book. It was quiet in his room, but he didn't spend all this money to just come and hang out in his room or on the room's balcony, and both the pools and the beach were very noisy thanks to some many families and young kids running around. The third pool which Shane hadn't gone to yet was a clothing optional adults only pool. Feeling like this was his last option, he decided to try his luck there.

    Entering beyond the 10 foot high gate, to keep hidden from others who might want to peek in, Shane looked around and saw mostly middle aged people walking around and laying in beach chairs. Some were in regular swimwear, some of the women were topless, and a few were totally nude. There were also a couple of open cabanas with covered padded lounge chairs. Feeling like splurging a bit more he decided to rent one of the cabanas. After giving it some serious thought as he made his way to the cabana he decided to drop his board shorts and lay out au naturale. Shane kept in shape, and while he may not be buff his body was pretty toned, and also while he was not hung like a porn star he his dick was no embarrassed at 7.25 inches hard and almost 5 inches while soft. At first being nude in public was all that he could think about, but as he laid back and began reading his book his mind calmed and he kind of forgot about it.

    After about 30 minutes or so he took a dip in the pool, again looking around he was both thankful and also a little disappointed that no one else at this pool seemed to be about his age. That changed about 5 minutes later when he noticed a family setting up in the cabana next to his. It was a older mother, father, a son who might be his age and a daughter who was either in her early 20s or late teens. She was a brunette wearing a pink bikini, wrapped around a very fit sexy body. The bottoms of her bikini was wedged between two tight toned ass cheeks. Shane was immediately attracted the the girl when he saw her, and his head almost exploded when she turned around and Shane instantly recognized her as Hailee Steinfeld. Shane knew her because his ex loved the Pitch Perfect movies and was a fan of her music, and on more than one occasion Shane had envisioned Hailee in his mind as he plowed his ex. Shane stayed in the water watching them for a few minutes hoping beyond all hope she would take part of the clothing optional aspect of the pool, but it was soon obvious that would not be the case. Her family had probably picked this pool for the privacy over anything else her realized.

    It wasn't until he had to get out of the pool that Shane remembered that he was nude, and he was going to have walk right passed Hailee to get back to his stuff. He waited up Hailee laying down, then Shane mustered the courage to get out of the pool and begin the walk back. "Don't get hard. Don't get hard. Don't get hard" Shane kept repeating to himself. He was now just seven feet or so away from Hailee's cabana when she sat up and turned his way. While he could not see her eyes behind her sunglasses, but there was little doubt in Shane's mind that Hailee was looking right at him as he walked towards her with his cock wagging back and forth as he walked. He thought he might have seen a small smile creep across her face before she turned to talk to her mom. The whole thing may have lasted less a few seconds, but it felt like an hour to Shane.

    He eventually got back to his chair and laid back. He tried to get back to reading, but his brain was too busy debating whether or not Hailee had actually seen, was that a smile he saw, was she smiling because she thought it was funny or because she liked what she saw. This debate raged on in his head for a good 20 minutes, until he started to feel hungry. He looked for a waitress to order some food and a drink from, but he had no idea where she was so he said screw it and just grabbed his phone and walked to the bar. He took the long way so that he wouldn't have to walk by Hailee again, but that was all for naught as she was at the bar already with the guy he was guessing was her brother.

    "Oh, so you would do it?" He heard her brother ask her as he approached them.

    "If I didn't have to worry about pictures of me ending up all over the internet, I'd consider it."

    "Bullshit. Even if that were the case, you wouldn't go nude at this pool with me, mom and dad here." Shane could not help but eavesdrop on their conversation as he looked over the menu at the bar.

    "Hey, according to the pervs on the internet I have nothing to be ashamed of" Hailee told her brother, and Shane responded with the thought of 'Amen" as he checked her out again out of the corner of his eye. That's when her noticed Hailee spin around and face him.

    "See Griff, this guy isn't hiding anything. Excuse me, how old are you?" Hailee asked Shane.

    "Ummm..awww. 28." Shane finally spoke up.

    "See, it's not like he's that much older than you, and doesn't have an issue letting it swing free. So why don't you drop your shorts?" Hailee said to her brother.

    "No, I'm not doing it." Griff told her.

    "What's the matter, afraid of your sister seeing your teenie weenie?" Hailee teased.

    "I'm not afraid, I just don't want to do it. An it sure isn't teenie, you can go ask Sophie about it."

    "Whatever." Hailee said as she turned back to the bar to grab her drink. Feeling like now or never moment Shane decided to engage Hailee.

    "Hey, you're Hailee Steinfeld, right?" He asked.

    "Yeah, that's me. You a fan?"

    "I thought you were great in The Edge of Seventeen, but my ex-girlfriend was a huge fan of your."

    "Oh, okay." Hailee said with kind of half laugh, unsure of how to respond.

    "I was wondering, do you think I could get a picture with you, it would piss her off so much to know I met you."

    "Yeah sure, what the hell," Hailee answered.

    "My name is Shane by the way," Shane said as he gave Griff his phone and then moved over next to Hailee and put his arm around her shoulder, and the two posed, but as soon as Griff lifted the phone to take the picture, he lowered it.

    "I'm sorry, I am just not sure I would be taking a picture of my sister with some guy who has his dick out," Griff complained.

    "I have an idea," Hailee said. She turned at more of an angle and lowered he hands so that they were being used as a shield to block the view of his crotch from the camera. Hailee thought the pose and the whole thing was really funny and shane tried not to focus in on the fact Hailee Steinfeld's hads were just a couple of inches away from his exposed dick as her brother took pictures of them. After taking two or three photos Griff lowered the phone and looked away from them, it was at that moment Shane purposefully flared his hips a bit causing his dick to swing up and smack the palm of Hailee's hand. Hailee recoiled her hand instantly but also started to laugh. Her brother asked what happened but both Shane and Hailee said it was nothing. Griff gave Shane is phone back and the two Steinfeld siblings said goodbye as they grabbed their drinks and walked back to their parents. Shane say Hailee at least once look back over her shoulder at him as they walked away.

    For the next two hours Shane pretended to red his book from his lounge chair, but in actuality he was either listening in on the conversations in the next cabana over when Hailee was there, or trying hard not to make it too obvious that he was watching her when Hailee was in the pool. Shane did notice Hailee look his way a few times while she was in the pool. It was at the end of those two hours Shane heard Hailee's parents say that they wanted to head back inside while Hailee say she wanted to lay out some more. After a short discussion they agreed to split up and Hailee was going to stay out alone while everyone else when back to the rooms. Five minutes after her parents were going, Hailee came into his cabana with a bottle of suntan lotion.

    "Hey, Shane could you rub some lotion on my back?" She asked.

    "Yeah sure." He stood up and took the bottle from her as she laid down on the lounge chair he was just on. She had her head facing the direction closes to him, and instead of thinking about how he was positioning himself he just stood over her and squeeze some lotion on to her upper back and then bent over to rub it in. It wasn't until he heard Hailee clear her throat and say "Yeah, okay wow" did Shane look down and realise that in his current position he had his half hard cock dangling and inch or so from her face.

    "Oh shit, I sorry I wasn't thinking." he apologise and backed away.

    "No it's ok. I didn't totally hate the view, it was just a little awkward," Hailee joked. Shane then moved around to the other end of the chair and straddled her legs, making sure he asked first, and then began rubbing the lotion into her skin. Shane was taking his time working it into her skin, and Hailee moaned as she enjoyed the massage from a relative stranger. Things started to get a little weird as Hailee started to squirm as Shane worked the lotion into her mid back. This was starting a chain of reactions. Hailee's squirming was causing her butt to rub up against Shane's crotch, which was making Shane's cock start to grow harder, which just caused Hailee to squirm some more. Soon Hailee was pressing her beautifully shapely ass into Shane's hard as steel erection.






    "You know, I always thought erections where taboo at nudist places" Hailee mocked Shane.

    "Yeah, sorry about that, he has a mind of his own at times."

    "It's okay, you just have to find a way to hide it so the other guests don't see it." It was at that moment something in Shane snapped. His dick had down taken over full control of his brain. He leaned over and picked up a rolled up towel of the stack on the ground. "Here bite into this" he told her.

    "Why?" She asked as she took the towel.

    "Just trust me." He told her and Hailee brought up the towel to her mouth and bit into it. Once she did that, Shane hooked his finger into the middle of her bikini bottoms, pulling the fabric out of her ass and over to the side, he exposed her asshole and part of her totally shaven pussy. Then without warning he buried all of his 7 inches into her twat. Hailee let out a muffled squeal as he did it. Shane just let his cock soak in her hot wet pussy as he went back to rubbing lotion onto her back. As he did that he looked around all of the pool area that he could see, trying to see if anyone was watching them or seemed to be onto the fact that the famous 21-year old actress/singer currently had a strange man's cock up inside her at a hotel pool.

    Shane slowly began to rock his hips as he worked her back. Hailee just lied there moaning into the towel.

    "You know this strap is getting in the way I am going to have to undo it," Shane announced as he undid the strap. He squeezed out some more location and he rubbed it in, making his way to her side boob, as his hips made small circular and in and out motions, essential massaging her inner pussy with his cock. Hailee began to lift her hips and ass a bit, giving Shanes dick better access as he fucked her, this also gave him the chance to work his hands under her and give each of her hard nipples a good tweek.

    This whole thing had been going on for a good five minutes when Shane started to pick up the pace and started fucking her harder. Hailee was still biting the pillow because she knew it was the best way to muffle her moans. Just like with how he got a hard on in the first place, a cycle was beginning to form and it was not one that was going to break any time soon. With the harder he fuck Hailee the better it felt, and the better it felt the less he cared if people caught them, and the less he cared if people caught them the harder he fucked her. Soon he was no longer even pretending with to rub in the lotion and was just holding onto her hips as he fucked her as hard as he could, and was he had his eyes locked onto her hypnotizing ass as it jiggled with each thrust.. Hailee continued to moan into the towel as her hands held onto the lounge padding for dear life. Soon she had a white knuckle grip on the chair padding and was screaming into the towel as he body let loose a powerful toe curling orgasim. Feeling her pussy clamp around his cock let Shane know he had done is job and gotten the starlet to climax, so there was no reason for him to fight his own any more. Pulling out he sprayed Hailee's ass like a firehose with is cum, before collapsing on top of her. "Merry Christmas" Shane mumbled as his shot his final ropes of cum onto her back. When he was done he fell back into the chair and the two of them just layed there for a minute catching their breath.

    When they had collected their breaths Hailee began to panic realizing what had just happened.

    "Holy shit I can't believe we just did that. Some might have saw us." She said as she hooked her top back together and made sure it was in place. Standing up she flashed Shane her swollen wet pussy before moving she bikini bottoms back into place. "Who just shoves their dick into someone without asking."

    "Well, I wasn't really planning to. You were just rubbing up against me and you made that comment about hiding my erection…"

    "And the only place you could hide it was inside of me?"

    "Well, yeah kind of." Shane shifting his position and layed back down on the lounge chair to lookup at Hailee as she used the towel she had been biting on to wipe the cum off her ass. "Don't act like you didn't enjoy it."

    "I… that's not the point. Point is had you asked we could have went somewhere private and not done it at a public pool with other people around. God I hope no one took a picture or a video of us."

    "You're right, that was wrong." Shane said confidently. While a few moments ago he was worried he might get in trouble for what he did, knowing that she enjoyed it was a huge boost to his ego. "Tell you what, I'm here for the rest of the week. Find me at some point, and I'll make it up to you by eating your pussy like it's the first hot meal I've had in six month."

    "Well...I...ummm" Hailee blushed. She really did not have any kind of come back for that response, and considering how he just fucked her it was a tempting offer. "I guess, okay...maybe. I don't know." And with that she stormed off the best she could considering her legs felt like jello. Meanwhile Shane sat back and relaxed, feeling pretty sure that he would be seeing Hailee around at some point in these next few days.



    Current Top 5
    1. Hailee Steinfeld
    2. Emma Watson
    3. Anna Kendrick
    4. Victoria Justice
    5. Jennifer Lawrence

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  3. #2
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    Very nice. Hot AF miami.


  4. Thanks miamidolfins5407 thanked for this post
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  5. #3
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    It's always nice to see Hailee get a story.

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