cherry
MASTERLIST
(hope you all like this sksksk WHY CANT I UPLOAD GIFS OR PICS TO THESE POSTS IM SO MAD UGH also there’s not so much smut, just mostly implied lol)
Word Count: 3,104
WARNING: prostitution
The windy streets of New York could almost be too much on a freezing night like this. Although you wish nothing more than to be back at your apartment, with some warm pajamas on and some hot cocoa in your hand - this was your job. You were allowed to wear a coat, but pants or long skirts were prohibited. You currently had on a tight black dress that barely covered your butt.
You thanked yourself for opting for the pair of black knee high boots you were currently wearing. Your hair hair was perfectly done as so was your makeup. You looked like something that came right out of the movie Pretty Woman. You were pleased with your appearance and knew that you would get some high paying clients. At this point, you didn’t care if they paid decent or not - you just wanted to go somewhere warm for a while.
“Fuckin’ freezin’ out here. They tryna kill us?” asks your good friend Gina.
Gina was her real name, but everyone called her Bambi, especially her clients. She has big doe like eyes, so the name fits her perfectly. Your nickname for your clients was Cherry, due to your signature bright red lipstick you would wear. Gina worked on these streets a lot longer than you. She took you under her wing when you first started and immediately since then you’ve been best friends - now roommates.
“I know. I can’t feel my hands.” you say, your voice trembling.
Your nose was ice cold and your eyes were burning from the harsh wind. You were looking around and spot a man parked in a nice SUV just across the road. He looked older and was staring directly at you. When you made eye contact with him, he looks nervous as he gets out of the car and makes his way across the semi busy road. It was your time to shine.
“Hi, baby.” you purr as he walks up and looks around nervously.
Gina watches the man and winks as he looks over to her. He gulps hard and reaches for his wallet in his back pocket.
“I, uh…” he starts as he opens it up. “I only got 20.” he tells you.
You’ve been told to never accept a 20 or lower. It was one of the rules.
“Sorry, baby. I’m worth more than that, don’t you think?” you ask with a wink.
The man’s face gets red as he’s embarrassed. His jaw tenses as he looks to Gina then back to you.
“She took a 20 last time. Why can’t you?”
You’re shocked for a moment as you turn to look at her. She looks irritated as she shakes her head no and walks up.
“I’ve never seen you in my life, pal. Now cough up some more or leave my girl alone.” she spats.
The man then gets irritated and reaches forward to grab your arm. Gina shouts out as you use your small clutch and start smacking him with it. Just then, you hear a shout and watch as an older man with a white beard hurries up and shoves the man back until he’s fallen onto the ground.
“Piss off!” he shouts as the man scrambles to get back to his car.
The older man looks to you and his eyes can’t help but look you up and down, slightly taken aback by your clothing choice.
“Are you alright?” he asks sincere.
You can’t break away from his blue eyes. This man was at least forty or plus years older than you, yet you were almost drawn to him.
“Thank you.” you tell him in your fake seductive voice. “Anything I can do to repay you?” you purr as you bite your lip and walk closer to him.
The man smiles sweetly as he realizes what you’re line of work is. He looks to the corner of the road and then back to you.
“Let me buy you a cup of coffee, yeah? You must be freezing.” he says as he looks back down to your bare legs.
You were freezing. Hypothermia would kick in at any moment you thought. You look back to Gina and watch as she’s talking to one of her regulars. You look to the man and smile slightly.
“If that’s what you want.”
***
“Men can be such dogs.” he says as he orders two hot coffees.
The coffee shop is warm and inviting. You look beyond out of place as people stare at you. Women roll their eyes and men practically drool, but everyone whispers. You didn’t fit in at such a nice place like this. You were an outcast.
“That’s an understatement.” you laugh as you both sit down in a small booth in the far back corner.
The man watches as you peer around the cafe.
“I’m Roger.” he says as he holds out his hand - a hand that you can spot tattoos on.
You stare at it for a moment and then back to him before reaching out as well.
“Cherry.” you say, using your fake name.
Roger looks half shocked by the fake name choice.
“Is it because of your lips?” he asks as someone brings the coffee to your table.
You raise a brow and smirk as you lean closer, allowing your cleavage to be exposed and push against the table for him to see - which he clearly does.
“You like my lips, Roger?” you purr. “I can show you exactly what they can do.”
Roger’s taking a sip of his coffee as he chokes a bit and coughs. You just continue to smirk as you lean back against the booth chair.
“Do you like what you do?” he randomly asks, causing your smile to fall.
You weren’t expecting a question like that. You’re taken aback as you awkwardly laugh and then just shrug.
“Bit personal, don’t you think?” you ask, not knowing how to answer.
Roger understands and nods his head.
“Listen, would you like to keep me company for dinner at my hotel? I’m here in the city all alone and could use the company. I’ll pay hourly if you want.”
Okay, you’ve never been asked that before. You were mind blown by the sincerity behind that question.
“Are you trying to murder me?” you ask as you lean forward, your eyebrows knitted together.
Roger’s eyes open wide for a moment before he laughs.
“I didn’t think inviting a beautiful girl back to my place for dinner would come across as me wanting to murder you, but I reassure you, no. I’m not.”
He has a sense of humor. You like that. You smile slightly and then nod as you stand up fast, grabbing your coffee.
“Alright, I’m starving.” is all you say before walking ahead of him and outside.
Roger jumps up and hurriedly places his money on the table and rushes after you.
***
“You’re willing to pay me hourly to just… Spend the evening with you?”
You’re in the passenger side of his vehicle as he drives through town. His car’s a sports car that you knew cost thousands. Something you always dreamed of having.
“I’m sure other man pay more for worse things.” he teases back, causing you to agree and laugh.
“Alright,” he starts as he pulls in. “Here we are.”
You look up the hotel and your face falls. Your eyes are wide and your mouth’s hung open.
“Holy shit!” you say loudly. “You’re staying at the Four Seasons? Do you know how much this place costs a night?!” you ask completely dumbfounded.
Roger just laughs and nods as he parks his car in front of the building as valet rush to open the door from him and you.
“I would hope I’d know. I am the one paying for it.”
Your door opens up and as you step out, the valet men are staring at you. A woman walks by with a small child holding her hand. The second she sees you, she makes a disgusted face and promptly places her hand over his eyes and hurries inside.
“You go on inside and get warm. I just have to fill out some paperwork for valet.”
You’re still in shock as you nod and slowly make your way inside. The lobby was huge and beautiful, more beautiful than you had imagined. It was clean and brightly lit as people were dressed up from head to toe. A woman at the front desk watches as you enter and her sweet smile falls into an annoyed one.
“Ma’am?” she asks as she walks away from her desk and up to you.
You look to her fast and smile.
“Ma’am, may I help you with something? Are you lost?”
Your smile falls as your cheeks turn red.
“Not lost.” you say back. “Waiting for someone.”
“Do you have a room with us?” she asks with a snarky tone.
She knew exactly what your answer would be.
“Um, no, but-”
“Well then I’m gonna have to ask you to leave the building. We just cleaned the floors.” she says with the rudest smile you’ve ever seen.
“Excuse me?” you ask, your voice echoing. “I’ll clean these damn floors with your face-”
Just then, Roger is behind you with his hand on your lower back. You stop talking, but are glaring at the woman. Her face shows that she's frightened from the threat you had just made and you didn’t care.
“She’s with me.” he says fast. “I didn’t realize that’s how this place treats guests. You should be beyond embarrassed.” he says angry.
“Oh, Mr. Taylor! I am so, so sorry!”
She keeps trying to talk to him as he rolls his eyes and walks away with his hand still on your back. You look back to the woman and smile sarcastically while mouthing ‘bye’ and waving your hand. The two of you make it to the elevator and wait for it to open. Once inside, you lean against the wall and close your eyes, sighing to yourself.
“I’m sorry about that.” he says softly.
You look to him and smile while shaking your head.
“Not your fault. I’m use to it. Trust me.”
Roger wants to say so much more to you, but he doesn’t as the doors open up once more. You all walk out and you follow him to his room. He opens the door and in you walk. Once again, your mouth falls open. The room he’s in is like a small house. There’s a living room, a bedroom, a kitchen, two bathrooms and a built in sauna.
“Wow,” you whisper as he shuts the door behind him.
The bedroom portion is connected to the living as it sits there wide open. You smirk to yourself as you walk over and crawl onto the bed, laying on your side. You eye Roger as he watches you with a faint smile on his lips.
“Wanna join me?” you ask.
He smiles even more as he turns around and walks away.
“Want a drink?” he asks, ignoring your question.
You’re confused as to why he’s not completely melting at your tricks. You roll your eyes and nod.
“Sure. Whatever you’re having.”
He brings back a drink and you both sip on it for a moment before he speaks up.
“You never answered my question from earlier.”
You look up confused.
“Do you like what you do?”
You tense your jaw as a smirk fills your face. You place your drink down and slowly make your way over to him. Roger gulps hard as he lowers his drink and watches you. You press yourself against him and fiddle with the black tie he’s wearing.
“I’m sure you’d like what I do.” you purr. “How about you make the most out of that money you’re spending, huh?”
As you’re saying this, your hands are down at his belt buckle and slowly undoing it. Roger’s hand reaches down and stops them. You look to him utterly confused.
“That’s really not why I invited you here.” he says softly. “When I saw you, before I knew what it is you… do, I wanted to meet you. Talk to you. Get to know you.”
Your heart melts as he explains everything to you. You remove your hands and take a step back - your eyes never leaving his.
“You really don’t want anything?” you ask softly.
“I really don’t.” he says back sweetly.
You’re both quiet for a moment as you walk back to the couch in the living room and lean against it.
“No.” you say, confusing Roger. “No, I don’t like what I do. It makes you feel like less of a human the more you do it and now… I don’t who I am anymore. I put on this persona of Cherry and… It’s like I get lost in it.”
Roger’s surprised that you actually had opened up to him - a complete stranger.
“Why do you keep doing it?” he asks, walking closer to you.
“Because… Because I work for someone and they would be beyond pissed off if I left. I’m too scared I suppose.”
Roger walks all the way up to you as you take in a deep, shaky breath. Something about him took your breath away. You look up and stare into his eyes as he does the same.
“You’re a very beautiful girl.” he whispers. “Let me help you.”
As he says those words, the wall you had built was put back up. You were angry as you stood up straight.
“I’m not a charity for you to feel bad for!” you spat at him. “I don’t need your pity help!”
You go to walk around him, but not before he grabs your wrist and pulls you back to him. Without thinking, you lean forward and kiss him. His hand’s cupping your face as you moan against him. The kiss was slow and sweet, the opposite of what you’re used to. Roger was taking his time with you. He hadn’t even been the one to start the kiss - you had. After several more moments, you both lean away to catch your breath.
“I’m sorry.” he whispers. “I wasn’t planning on that happening.”
You just smile and shake your head.
“That one’s on the house.” you tease, causing him to laugh. “Kiss me again.” you whisper.
He listens as his lips are back on yours. This was the first time in a very, very long time that someone had actually wanted to kiss you and not because they paid you to. The whole mood was different from previous hookups and it made this warm feeling in your belly spark up. Being wanted and not tossed to the curb afterwards was a good feeling and you didn’t want this to end.
“We’re not on the clock anymore.” you sigh against his lips.
Roger’s hands were perched on your hips as he squeezes. You had began slowly walking backwards towards his bed. He stops and leans away, slightly shocked.
“Not on the clock?” he asks.
“I don’t want your money.” you tell him. “Right now, just you.”
Roger smiles and resumes him kissing you until you’re all the way to his bed. The back of your legs hit it and you fall backwards. You laugh loudly as Roger stares down at you - admiring you. This was also a first. In the eyes of every man you’ve been with was lust, but with him, it was different. Lust was nonexistent and replaced by something you weren’t sure of. What you were sure of was that, when the morning comes, you’d be tangled with Roger in bed.
***
You were right.
The sun attempted to shine through Roger’s hotel’s curtains. Your limbs were tangled up as your naked bodies pressed together. Roger hums as he begins to wake up and squirm around, causing you to do the same. You stretch and yawn as you look up to a sleepy Rog. His hair was crazy, but he looked none the less gorgeous. You couldn’t help but smile.
“Good morning.” you whisper.
“Mmm, good morning.” he whispers back.
“Sleep okay?” you ask as you sit up on your elbow.
“Like a baby.” he teases. “How about you?”
“Well,” you start with a smirk. “From what I can remember, we didn’t do that much sleeping.”
Roger smiles and raises his brows as he nods his head.
“For an old man, I’m surprised I could stay up that late.” he teases.
You have a serious look on your face as you bring your finger to his mouth and cover it.
“Don’t call yourself that. Understood?” you ask seriously.
Roger can’t help but smile as he nods.
“Yes, ma’am.” he jokes, causing you to laugh.
Your smile faintly falls as you look down and think.
“Were you serious about helping me, you know, get out of this?” you ask.
Roger knows exactly what you’re referring to.
“Cross my heart.” he tells you as he sits up as well.
He makes a x motion over his heart as you laugh and bite your lip.
“Cross my heart.” you whisper as you make the same x motion.
Roger stared at you with the crinkling of his blue eyes. You smile and suddenly think about Gina and how worried she must be. You sit up fast and search for your outfit that was thrown across the floor.
“I should really be going.” you say sadly. “My roommate probably has all of New York looking for me.”
Roger gets up from bed and dresses quickly with you.
“Wish you didn’t have to leave.” he admits, causing you to look at him and smile.
“Don’t think this is the last of me you’ll see.” you tease. “But next time, it’ll be double.”
Roger smirks and walks up to you and places his hands on your hips.
“Oh will it?” he asks. “I’d pay anything to see you again.”
You bite your lip as you smile and lean in to kiss him one last time.
“I put my number next to your bed.” you tell him as you walk away towards the door.
You open it up just as he calls out for you.
“I still don’t know your name!”
You turn around and watch as he anxiously waits.
“Y/n.” you tell him with a smile and then you’re gone.
You were confused about what had replaced the look of lust, something you had been so used to seeing, in Roger's eyes. You just didn’t know that eventually you would understand that look like the back of your hand.
Love.
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