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Bailee & AJ
Collab with @Lovely Complex
Flashback: Morning after party
Location: Upstairs, still on boat, in one of the Bedrooms.
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No good came from women like Cecily. Any Helmsley woman for that matter was bad news bears. And the thing was? Most of them AJ considered friends. Here he was, on a stage (metaphorically speaking), where he felt he had no control over himself. A puppet to devious, little things that liked to play with power. One including his ex, if only Jamie knew the control he still had over AJ.
Having used the shower in their personal bathroom on the boat, the gearhead came out of the steaming room rubbing a white towel on his unruly swirls that was his fluff of hair. Still shirtless, but at least now he had his jeans on from last night.
“Bailee, wake up.” He let the towel rest on his head, as he approached the girl still knocked out cold. Note to self, build tolerance. Nudging her shoulder, he tried to peacefully wake the sleeping beauty up. However, Tylers were more often than not impatient people, so this led to him pulling her pillow from under her head and hitting her face, “RISE AND SHINE, BABE.”
There were two words you would never hear in a single sentence: Bailee and hungover. The noun and the adjective were not meant to be placed next to each other- it was both grammatical nonsense and real life error. And yet, here the Hemsley Heiress was, hungover beyond belief and feeling absolutely dreadful. AJ’s loud and forceful voice rang clear through her buzzing ears, and the pillow to the face was not only a wake up call, but an unnecessary reminder of how much pain she was in.
Bailee’s limbs were so heavy, she felt as though they were made of lead; her muscles as sore and strained as they would be if she had run a five mile loop. Had she run around last night? She had no clue. Her head was another story, both pounding and light as air at the same time, still making her feel as though she was living in a drunk fantasy, but the presence of a headache very real and throbbing. With a delicate whimper she finally peeled open her eyes that had been sealed shut with drunk dreamless sleep, and attempted to look directly at AJ although the room was still spinning.
“I’m not your babe.” She grumbled, letting her eyes slide shut once again.
“That’s not what our school thinks…” AJ spoke under his breath, intentionally speaking loud enough so she would catch it. Grabbing the cup of water off the nightstand, he gestured for her to sit up and drink. If she looked at her phone, there was a voicemail from both her cousin, Cecily, and her mother, Adelaide. Patiently, he surveyed her reactions.
Bailee let AJ’s words turn like gears in her head until they clicked together. The school thinks? Shooting up into a seated position, she couldn’t possibly believe that her reputation preceded her before she even knew what is was. “What do you mean what our school thinks I-” The brunette may have sat up a little too fast. All of the sensations she had felt whilst lying down multiplied, and she could feel the wind being knocked out of her. Grimacing, she looked at AJ. “This is worse than the time I had mono. Way worse.”
Shrugging, AJ sat beside her and put the water in her hand, “I tried to limit you, but you don’t listen. Ever.” When the glass was no longer in his grasp, he ran his hand through his wild mane and chuckled, “Welcome back, Bailee. You’ll learn sooner or later that privacy is dead.” With that, he pulled out his phone and scrolled through everyone’s snapchat stories of the party, where people caught them spending the entire night together, which led to them going into a room. This room. He had a lot more to say, but he held his tongue. Reactions. He needed to see her reactions. If he was going to make this work, he had to make her believe that he wanted her.
The brunette had never had an out of body experience… that was until now. Bailee studied every single snapchat story in disbelief, having a hard time believing that the curly haired girl she was looking at was indeed herself. Bailee watched her drunk self intently, focusing on every single moment she was pressed up against the curly haired boy currently next to her with a scrutinizing eye. Fragments of the evening came back, but she mostly drew a blank, especially when she watched AJ throw her over his shoulder and carry her off into a room upstairs. Looking around, it clicked. Did they? Did she? Was it…. gone? Looking over at the boy she had known her whole life with shock in her eyes, the words tumbled out before she could form proper thoughts. “Why’d you bring me up here?”
“To put you to sleep.” AJ pointed at the half filled tea cup. “You better not be thinking I fucked you. I got class, Bails, and you’re a damn virgin.” The boy scoffed, coming across as offended that she’d think he’d take advantage of her.
“No, no, not at all-” She stammered.
“Well, not saying I haven’t, well, y’know. You’re a good looking girl, but totally out of my league.” He nervously laughed to himself.
Bailee did a double take at AJ’s words. Did he just call her good looking? And say she was out of his league? This was one of her best friends from childhood talking here, not just anyone. Mind boggled, she asked a clarifying question. “Wait, wait, wait, hold on...you’ve thought about it before?”
With his charming smile plastered on his face, his gaze softened while his stare never wavered from her face, “I saw an opportunity, before I got with Jamie. Didn’t take it. And then you left. So yeah, I’d say I thought about it.” Truth be told, this was not a lie, but he wasn’t crushing hard enough to stop her from leaving. His feelings for Jamie, though, unfurled like wildfire. Immediate chemistry and like magnets, they were drawn to each other. Part of him believes they still are… like magnets.
The words he spoke seemed to go in one ear and out the other, all except for the last four words he said. All Bailee could keep hearing in her head was I thought about it and that was all she needed to know. Out of all the people in this world, the last person she imagined herself being with was none other than AJ Tyler. She had never even thought about it before, that’s how obsolete of an idea it was. He was daring and edgy, and she was, well, business-y and clean cut. They knew how to argue like no one else- they were kind of like oil and water. “...oh.” Was all she could say, awkwardly and dumbfounded.
Rolling his eyes, disappointed at how obvious she was being, he got up from the bed and nonchalantly stretched, “It’s all good, I’ll just clear things up with the school and your family.” He reached for his button up shirt off the one seater.
“No wait, I mean- I didn’t mean it like that- I…” Bailee found herself searching for the right words to say. How else are you supposed to react when your best friend confesses they’d thought about being with you before? But before she could say anything else, another word stuck out like a sore thumb. “Wait, my family? What do you mean my family?” Looking around desperately for her phone, she found it plugged in on the nightstand filled with notifications, most notably, two voicemails from her mother and Cece.
“Oh god.”
“Y’know what? I’ll leave you to it. It’s almost time for us to bounce, anyways. When you’re ready, I’ll be outside. You can tell me what you want to do after you’ve gathered your thoughts. For now, relax, shower, eat some fruit.” Grinning to her like the playful boy that he was, AJ leaned in close to her puzzled face, too close, and pushed her hair behind her right ear, “Whatever you decide, I’ll be down.” And so, he pulled back, turned on his heel, and made his exit, closing the door behind him. Taking a deep breath in, he whispered to himself, “Cece, this better be worth it.” Before walking away, while buttoning his shirt.
Chills ran up Bailee’s spine as AJ’s touch brushed her hair back, revealing her now flushed face. This was awkward. Extremely awkward, and she had no clue what to think. All of these things came out of absolute nowhere… or was she just too blind and self centered to have noticed? As the door closed behind him, Bailee tried to think back if there were any signs that her best friend could have felt this way towards her, but she was drawing up a blank. Deciding to flood her brain with hopefully some different information, she navigated her way to her voicemail box, clicking on Cece’s message and bringing the phone up to her ear to listen.
You slut, I can’t believe you didn’t tell me you were going to feast on AJ last night! Sure, we haven’t talked in weeks because I’ve been out and about, but still. As your favorite cousin, I desire to know the deets. How big is he? Did you give head, finally? I’ve always wondered if his ego matched what he has in his pants. Surely it must, if he got with you. The Helmsley with an iron chastity belt. Ha. Well, not anymore. How exciting. I’m so happy for you!
To make sure this doesn’t get misunderstood, since right now everyone is talking about you, thinking you’re a nasty and totally jealous that AJ is still on Jamie’s ass - yes, sweetums, I saw the video of you riding his ass when he shattered poor Marshall’s heart, so I did what any good samaritan would do.
I told Auntie! Please let me know how that goes. Okay, love you. Kiss. Kiss. Bye, lover!
The brunette tried with all of her might to prevent her jaw from hitting the floor, but alas, it didn’t work. Cece was certainly a piece of work, but this took it too far. Not many people knew that Bailee was still the virgin mary- but Cece was one of the few who did. Why her cousin assume that she gave it up so quickly? And to AJ of all people? Rolling her eyes at the end of the voicemail, Bailee clicked on the next name with a blue dot next to it… her darling mother.
Bailee’s mother’s voice was like a whispering meadow and if it could remind you of a character, it would be that of the alluring, prepossessing, and sensual Jessica Rabbit. She was not dark and evocative like Evelyn Green’s Glam noir and dark cabaret femme fatale stage presence, but she was a close second. If there was one thing that could describe the First Lady of the Helmsley enterprise, it would be sex. Complete, pure, and utter sex. From when she was a young maid cleaning for Christopher and Bianca Helmsley to now where she has found herself married with kids to the youngest Helmsley, Ryan Helmsley. The man of the hour who inherited the family business because his eldest brother, Joseph Helmsley-Lovelace, chose acting instead, as well as helping his wife’s hotel global brand expand (Hotel Millenium). No matter the season, she will be seen as a sultry, yet moral, beauty in media. A symbol of sex like Marilyn Monroe.
Bailee, please make sure AJ, as well as yourself, are available for brunch Sunday. I will forward you a time and place within the next hour unless you have a preference. Ultimately, this is for you. I’m pleased you’re finally enjoying being young. I was worried you had forgotten to be a teen. The business will always be here, you’re only seventeen for so long...I’m grateful AJ can help you with that. Good choice. Mommy approves and I’m sure daddy will approve too. Word of advice, please don’t mind whatever rumors are spreading around. You are a Helmsley, which means you are an unbreakable fortress. It isn’t worth investing time and energy with the wrong people. Oh goodness, Sierra’s demanding to go on her playdate. I’ll talk to you soon, Bunny. I love you! Okay, Monkey let’s go!
….BRUNCH?! The heiress couldn’t believe her ears at how excited her mom was regarding this arrangement. More excited than she had heard her sound in a long time. It was shocking, and Bailee partially didn’t want to hear it.
At the same time though, she listened to her mother’s words carefully and willingly. Enjoy being young.
Throwing her phone down on the bed, the familiar phrase was beginning to click in her mind. People had been telling her those three words since she was a child- when the brunette wanted to take the world by storm, everyone always said she needed to slow down and live in the moment. Bailee then recalled that the reason why she got so intoxicated in the first place was because she needed to remember she wasn’t an adult yet. Her sister had told her this, her brother had told her this, AJ had told her this. She still had mistakes to make and a life to live before she took over her father’s company- and maybe this hangover and this whole situation was finally helping her realize that.
With everything swirling together and beginning to resonate, one chord struck in her head. Did she miss the signs about AJ liking while she was so busy running the show? Bailee didn’t realize at all that he was interested in her… was that her own fault? She did truly care about him- she always had. But was this caring and compassion meant to be something more?
Well that she would soon find out for herself.
Clamoring out of bed and over to the door, she flung it open, poking her head out to find the curly haired boy not to far away from the staircase.
“Got any plans Sunday morning?”
The boy's lips curved into that sly smile of his as he glanced back at his new ‘girlfriend’ “None in particular. Why? What's up?”
Having used the shower in their personal bathroom on the boat, the gearhead came out of the steaming room rubbing a white towel on his unruly swirls that was his fluff of hair. Still shirtless, but at least now he had his jeans on from last night.
“Bailee, wake up.” He let the towel rest on his head, as he approached the girl still knocked out cold. Note to self, build tolerance. Nudging her shoulder, he tried to peacefully wake the sleeping beauty up. However, Tylers were more often than not impatient people, so this led to him pulling her pillow from under her head and hitting her face, “RISE AND SHINE, BABE.”
There were two words you would never hear in a single sentence: Bailee and hungover. The noun and the adjective were not meant to be placed next to each other- it was both grammatical nonsense and real life error. And yet, here the Hemsley Heiress was, hungover beyond belief and feeling absolutely dreadful. AJ’s loud and forceful voice rang clear through her buzzing ears, and the pillow to the face was not only a wake up call, but an unnecessary reminder of how much pain she was in.
Bailee’s limbs were so heavy, she felt as though they were made of lead; her muscles as sore and strained as they would be if she had run a five mile loop. Had she run around last night? She had no clue. Her head was another story, both pounding and light as air at the same time, still making her feel as though she was living in a drunk fantasy, but the presence of a headache very real and throbbing. With a delicate whimper she finally peeled open her eyes that had been sealed shut with drunk dreamless sleep, and attempted to look directly at AJ although the room was still spinning.
“I’m not your babe.” She grumbled, letting her eyes slide shut once again.
“That’s not what our school thinks…” AJ spoke under his breath, intentionally speaking loud enough so she would catch it. Grabbing the cup of water off the nightstand, he gestured for her to sit up and drink. If she looked at her phone, there was a voicemail from both her cousin, Cecily, and her mother, Adelaide. Patiently, he surveyed her reactions.
Bailee let AJ’s words turn like gears in her head until they clicked together. The school thinks? Shooting up into a seated position, she couldn’t possibly believe that her reputation preceded her before she even knew what is was. “What do you mean what our school thinks I-” The brunette may have sat up a little too fast. All of the sensations she had felt whilst lying down multiplied, and she could feel the wind being knocked out of her. Grimacing, she looked at AJ. “This is worse than the time I had mono. Way worse.”
Shrugging, AJ sat beside her and put the water in her hand, “I tried to limit you, but you don’t listen. Ever.” When the glass was no longer in his grasp, he ran his hand through his wild mane and chuckled, “Welcome back, Bailee. You’ll learn sooner or later that privacy is dead.” With that, he pulled out his phone and scrolled through everyone’s snapchat stories of the party, where people caught them spending the entire night together, which led to them going into a room. This room. He had a lot more to say, but he held his tongue. Reactions. He needed to see her reactions. If he was going to make this work, he had to make her believe that he wanted her.
The brunette had never had an out of body experience… that was until now. Bailee studied every single snapchat story in disbelief, having a hard time believing that the curly haired girl she was looking at was indeed herself. Bailee watched her drunk self intently, focusing on every single moment she was pressed up against the curly haired boy currently next to her with a scrutinizing eye. Fragments of the evening came back, but she mostly drew a blank, especially when she watched AJ throw her over his shoulder and carry her off into a room upstairs. Looking around, it clicked. Did they? Did she? Was it…. gone? Looking over at the boy she had known her whole life with shock in her eyes, the words tumbled out before she could form proper thoughts. “Why’d you bring me up here?”
“To put you to sleep.” AJ pointed at the half filled tea cup. “You better not be thinking I fucked you. I got class, Bails, and you’re a damn virgin.” The boy scoffed, coming across as offended that she’d think he’d take advantage of her.
“No, no, not at all-” She stammered.
“Well, not saying I haven’t, well, y’know. You’re a good looking girl, but totally out of my league.” He nervously laughed to himself.
Bailee did a double take at AJ’s words. Did he just call her good looking? And say she was out of his league? This was one of her best friends from childhood talking here, not just anyone. Mind boggled, she asked a clarifying question. “Wait, wait, wait, hold on...you’ve thought about it before?”
With his charming smile plastered on his face, his gaze softened while his stare never wavered from her face, “I saw an opportunity, before I got with Jamie. Didn’t take it. And then you left. So yeah, I’d say I thought about it.” Truth be told, this was not a lie, but he wasn’t crushing hard enough to stop her from leaving. His feelings for Jamie, though, unfurled like wildfire. Immediate chemistry and like magnets, they were drawn to each other. Part of him believes they still are… like magnets.
The words he spoke seemed to go in one ear and out the other, all except for the last four words he said. All Bailee could keep hearing in her head was I thought about it and that was all she needed to know. Out of all the people in this world, the last person she imagined herself being with was none other than AJ Tyler. She had never even thought about it before, that’s how obsolete of an idea it was. He was daring and edgy, and she was, well, business-y and clean cut. They knew how to argue like no one else- they were kind of like oil and water. “...oh.” Was all she could say, awkwardly and dumbfounded.
Rolling his eyes, disappointed at how obvious she was being, he got up from the bed and nonchalantly stretched, “It’s all good, I’ll just clear things up with the school and your family.” He reached for his button up shirt off the one seater.
“No wait, I mean- I didn’t mean it like that- I…” Bailee found herself searching for the right words to say. How else are you supposed to react when your best friend confesses they’d thought about being with you before? But before she could say anything else, another word stuck out like a sore thumb. “Wait, my family? What do you mean my family?” Looking around desperately for her phone, she found it plugged in on the nightstand filled with notifications, most notably, two voicemails from her mother and Cece.
“Oh god.”
“Y’know what? I’ll leave you to it. It’s almost time for us to bounce, anyways. When you’re ready, I’ll be outside. You can tell me what you want to do after you’ve gathered your thoughts. For now, relax, shower, eat some fruit.” Grinning to her like the playful boy that he was, AJ leaned in close to her puzzled face, too close, and pushed her hair behind her right ear, “Whatever you decide, I’ll be down.” And so, he pulled back, turned on his heel, and made his exit, closing the door behind him. Taking a deep breath in, he whispered to himself, “Cece, this better be worth it.” Before walking away, while buttoning his shirt.
Chills ran up Bailee’s spine as AJ’s touch brushed her hair back, revealing her now flushed face. This was awkward. Extremely awkward, and she had no clue what to think. All of these things came out of absolute nowhere… or was she just too blind and self centered to have noticed? As the door closed behind him, Bailee tried to think back if there were any signs that her best friend could have felt this way towards her, but she was drawing up a blank. Deciding to flood her brain with hopefully some different information, she navigated her way to her voicemail box, clicking on Cece’s message and bringing the phone up to her ear to listen.
You slut, I can’t believe you didn’t tell me you were going to feast on AJ last night! Sure, we haven’t talked in weeks because I’ve been out and about, but still. As your favorite cousin, I desire to know the deets. How big is he? Did you give head, finally? I’ve always wondered if his ego matched what he has in his pants. Surely it must, if he got with you. The Helmsley with an iron chastity belt. Ha. Well, not anymore. How exciting. I’m so happy for you!
To make sure this doesn’t get misunderstood, since right now everyone is talking about you, thinking you’re a nasty and totally jealous that AJ is still on Jamie’s ass - yes, sweetums, I saw the video of you riding his ass when he shattered poor Marshall’s heart, so I did what any good samaritan would do.
I told Auntie! Please let me know how that goes. Okay, love you. Kiss. Kiss. Bye, lover!
The brunette tried with all of her might to prevent her jaw from hitting the floor, but alas, it didn’t work. Cece was certainly a piece of work, but this took it too far. Not many people knew that Bailee was still the virgin mary- but Cece was one of the few who did. Why her cousin assume that she gave it up so quickly? And to AJ of all people? Rolling her eyes at the end of the voicemail, Bailee clicked on the next name with a blue dot next to it… her darling mother.
Bailee’s mother’s voice was like a whispering meadow and if it could remind you of a character, it would be that of the alluring, prepossessing, and sensual Jessica Rabbit. She was not dark and evocative like Evelyn Green’s Glam noir and dark cabaret femme fatale stage presence, but she was a close second. If there was one thing that could describe the First Lady of the Helmsley enterprise, it would be sex. Complete, pure, and utter sex. From when she was a young maid cleaning for Christopher and Bianca Helmsley to now where she has found herself married with kids to the youngest Helmsley, Ryan Helmsley. The man of the hour who inherited the family business because his eldest brother, Joseph Helmsley-Lovelace, chose acting instead, as well as helping his wife’s hotel global brand expand (Hotel Millenium). No matter the season, she will be seen as a sultry, yet moral, beauty in media. A symbol of sex like Marilyn Monroe.
Bailee, please make sure AJ, as well as yourself, are available for brunch Sunday. I will forward you a time and place within the next hour unless you have a preference. Ultimately, this is for you. I’m pleased you’re finally enjoying being young. I was worried you had forgotten to be a teen. The business will always be here, you’re only seventeen for so long...I’m grateful AJ can help you with that. Good choice. Mommy approves and I’m sure daddy will approve too. Word of advice, please don’t mind whatever rumors are spreading around. You are a Helmsley, which means you are an unbreakable fortress. It isn’t worth investing time and energy with the wrong people. Oh goodness, Sierra’s demanding to go on her playdate. I’ll talk to you soon, Bunny. I love you! Okay, Monkey let’s go!
….BRUNCH?! The heiress couldn’t believe her ears at how excited her mom was regarding this arrangement. More excited than she had heard her sound in a long time. It was shocking, and Bailee partially didn’t want to hear it.
At the same time though, she listened to her mother’s words carefully and willingly. Enjoy being young.
Throwing her phone down on the bed, the familiar phrase was beginning to click in her mind. People had been telling her those three words since she was a child- when the brunette wanted to take the world by storm, everyone always said she needed to slow down and live in the moment. Bailee then recalled that the reason why she got so intoxicated in the first place was because she needed to remember she wasn’t an adult yet. Her sister had told her this, her brother had told her this, AJ had told her this. She still had mistakes to make and a life to live before she took over her father’s company- and maybe this hangover and this whole situation was finally helping her realize that.
With everything swirling together and beginning to resonate, one chord struck in her head. Did she miss the signs about AJ liking while she was so busy running the show? Bailee didn’t realize at all that he was interested in her… was that her own fault? She did truly care about him- she always had. But was this caring and compassion meant to be something more?
Well that she would soon find out for herself.
Clamoring out of bed and over to the door, she flung it open, poking her head out to find the curly haired boy not to far away from the staircase.
“Got any plans Sunday morning?”
The boy's lips curved into that sly smile of his as he glanced back at his new ‘girlfriend’ “None in particular. Why? What's up?”
