The Red Line Pt. 01

Story Info
A hooker turns the tables on Roy with a little blackmail.
13.4k words
4.71
38.9k
88

Part 1 of the 4 part series

Updated 06/09/2023
Created 02/18/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Hey everyone! Here's a fresh new story. Like always, all characters involved in sex are over the age of 18.

Chapter 1: The Tables Have Turned

Like any other night, I end up 50 shades of fucked up. Of course, when you're high on coke and drunk like a skunk. It didn't take me long to end up in the wrong part of town, looking for the kind of company you have to pay for.

That's when I saw the most gorgeous Latina. An ass like a peach. The kind you want to suffocate yourself in. And she's got a pair of legs that go on for days. Of course, in this part of town, she most likely has a hidden weapon between those thick thighs of hers. Her eyes meet mine. "You looking for some company?" she asks.

"It just so happens that I am," I say.

"Well then, it looks like I'm your girl. You don't mind a girl with a little something extra, do you?" she asks, raising an eyebrow.

"If I did, I wouldn't be here," I say.

"Well good, that's a relief. You couldn't imagine how many assholes stumble down here not realizing the kind of goods being offered. They only figure it out behind closed doors. And that never ends well. I'm not looking for a beating," she says.

"I just want to fuck. Besides, I much prefer a tight asshole over a loose pussy any day," I spit out. My breath is thick with whiskey and a slight hint of slurring.

"You got cash to pay for my company, right?" she asks.

"Of course. You think I'm a bum or something?"

"I'm just making sure," she says. "And you certainly smell the part."

"Trust me, make it worth my while and I'll load your pockets," I say.

"And what does it take to make it worth your while?" she asks.

"Just that ass. Let me tie you up, I'll throw in a huge tip."

"I don't want anything too rough," she says. She's quite the looker. A face like an angel.

"What if I pay extra?" I ask.

"I don't know, it'd have to be a lot extra."

I just smile. "Relax, I'm not going to hurt you."

"Okay," she says.

"Shall we?" I ask extending my hand.

"We shall."

We take an uber to a nice hotel. Once I get a room, we get nice and comfy inside. "Let me get ready really fast," she says.

"Okay," I say.

"So, are you married? Or do you have a girlfriend?" she asks as she walks over to the bathroom while I plop down on the bed.

"Nope, none of the above," I say.

"How come? You're definitely handsome."

I only shrug. "It's a long story."

She comes and takes a seat next to me. "So... You got a name?" she asks.

"The names Roy," I say.

"Cindy," she says as she places her hand on my thigh.

"So Roy, what do you do for a living?" she asks.

"I write books," I say.

"Really? I'm a huge reader. What have you written? Maybe I've read some of your work."

"It doesn't matter," I say. "Are we going to fuck or not?"

"Hey, calm down. I was just trying to get to know you a little better," she says.

"I'd rather you didn't," I say.

"Fine, let's get on with it then," she says throwing me a look of apathy as she crosses her arms.

I look up into those hazel eyes of hers. She leans in and places her lips upon mine. She kisses me before I pull away. I get up off the bed and start undoing my pants. She comes up behind me and kisses my neck as she wraps her arms around my waist. Her hand sinks down and grabs my cock. I drop my pants to the floor and kick them off. She helps me pull my shirt off. I turn around and lift her dress up over her head. She's got a red thong on. No bra. Her big tits are nice and firm. I run my hand over them and give em a squeeze.

She leans up and kisses me again. I pull away once more. "What? Don't like being kissed?"

"Not tonight."

"Why?" she asks.

"That's none of your business," I say.

I spin her around and bend her over the bed as I smack that thick ass of hers. "Hey, don't get too rough," she says. I lean down and grab the belt off my pants. "Wait. what do you plan on doing with that."

"Relax," I say. "Just some restraints."

I tie up her wrists nice and tight. "It's too tight. It hurts," she says.

I ignore her as I pull down her thong. I grab her thighs and spread open her perfect ass. Her cock dangles between her legs. I reach down and tug on it. Shit. Her dick is bigger than mine.

I bring my hand down on her ass cheek. "Ouw, I said I don't want it rough," she says.

I rub the head of my dick up in between the crack of her ass before finding that little rosebud of hers. "Wait a sec. Are you not going to use any lube?" she asks.

I ignore her and try to push my dick in. It's fucking tight. "You fucking asshole!" she growls and whimpers as she bites into the bedsheets. "Fuck!"

I force myself in. "Fuck you!" she screams. I give her ass a hard slap.

"You fucking bastard," she yells as I plunge my cock inside her, spreading her open. She groans out loud as I push my cock all the way in. She sniffles as she looks back at me with tear-filled eyes. "Fuck you!"

I grab her hair and pull hard on it. "Ow! You prick."

"Take it like the tranny whore you are. It's not like you're not getting paid for it," I say.

I slam my dick into her and continue to do so. Each thrust makes her groan even harder. I give her ass a hard smack. She cries out.

I can't hold out any longer. I slam into her and release a torrent of cum, painting the inside of her ass white. I have to catch my breath as I collapse on top of her. "Get off of me," she says. I roll onto my back, pulling my cock out of her ass. "Are you going to untie me, asshole?"

"Not with a dirty mouth like that," I say. "And besides, who says I'm done?"

"Let me go, you fucking asshole. Please."

I stumble over to my pants and grab the flask I had in my pocket. I take a big swig of it. I walk over to her and give her ass another slap. "Fuck you!" she screams.

"Please just let me go," she begs.

I let out a sigh and fumble with the belt, loosening it up from her wrists enough for her to get it undone. Then I down the rest of my whiskey. It doesn't take much before the room starts to spin and everything goes dark.

--

I wake up in my own drool. My hands. They're bound behind my back. "Urghh! Fuck." My ass feels like it's being torn apart.

"Hurts, doesn't it you fucking asshole," a woman says as she lands a hard smack on my ass. God damn, her dick is fucking huge. "The tables have turned, bitch."

I bite into the sheets as she plows into my ass. "You know... I was going to just humiliate you and steal your wallet and phone. But then I found out who you really are, Roy. Or should I say Cinders. To fucking think, you're my favorite author."

She pushes pulls out her dick far enough to slam back inside my ass. "By the way, say hello to the camera, you piece of shit."

"How the fuck did you figure out who I am?" I growl as she fucks me even harder.

"I not only went through your phone, but I changed the password and made it so only my fingerprint unlocks it. I also changed your bank account passwords and social media accounts."

"You did what!" I cry out as she pounds me harder. "I'll pay you whatever you want. Just get the fuck off of me. What do you want?"

"You really don't know the predicament you're in right now. I don't just want your money. You're my bitch from now on," she says as she thrusts into me, her hips slapping into my ass so hard, the clap echoes through the room. She grabs a hold of my hair as she slaps my ass. To make matters worse, my head is pounding from one hell of a hangover. How the fuck did I get myself into this mess? I don't even remember much of last night. "Who the fuck are you?"

"You don't remember? Go figure, you were so fucking drunk, I'm not surprised. You fucked me after I told you I didn't want it rough," she says as she slams into me, making the bed shake. "And you fucking lied about being married. I found your ring in your pocket, you're such a fucking douche. And to think I looked up to you. Wait until your wife sees this video, in fact, wait until the whole world sees it. What would the media think when a video of the best selling author getting his ass railed goes viral."

"You wouldn't!" I shout. She slams into me and holds her cock there.

"Why wouldn't I?" she says.

"I said I would pay you."

"Oh, that's not enough. Your money is as good as mine. I don't just want your money, I want your life. Like I said, you're my bitch from now on. You're going to do everything I say. If not, the whole world is going to see you taking a dick up the ass. And your marriage will be over."

"My marriage has been over for a long time now," I say.

"I can see why. With an asshole like you for a husband, who wouldn't fucking leave you?" she says as she picks up where she left off, fucking my ass harder and faster. She lands another blow on my asscheek. The pain is excruciating. Spots start to cover my sight. "I guess that just makes things a lot easier for me."

"What do you mean?" I ask.

"What don't you understand about being my bitch? I can only imagine what kind of mansion you live in. Looks like I'm moving in," she says. She thrusts that big dick deep inside me.

"Fuck, I'm going to cum."

She pulls out and rolls me over onto my back before straddling my chest. She reaches over and grabs her phone. "Now for the big finish."

She strokes her big dick as she holds her camera up. She takes aim at my head and drops a load of cum across my face. Her dick sprays her sticky jizz like a firehouse basking my face in her sperm.

"There's the money shot," she says. "Say cheese."

With a flash from her phone, she takes a picture of my facial.

"Holy shit, are you fucking hard right now?" she asks as her ass rubs up against my cock. "You are. You fucker!"

"No, I'm not. Haven't you ever heard of morning wood?" I ask.

"That's too bad, you're ass is going to get well acquainted with my dick," she says.

"Just let me go," I snap.

"Oh not quite yet. I want to make sure you understand your predicament. You do anything to hurt me, and this video gets posted on each of your social media accounts and all of your bank accounts get drained."

"I'm not going to hurt you," I say.

"You said that last night," she says.

"I don't even remember last night," I say.

"That doesn't mean shit. Maybe you should lay off the alcohol. In fact, from now on you're done drinking," she says. "And whatever else you're on."

"You can't tell me what to do!"

"I sure as hell can. Or did you forget about the video and your bank accounts?" she says as she holds up my phone above my head. "Listen, let me lay down the rules you're going to live by from now on. I'm in charge of your life. By day, you're going to be my perfect boyfriend. You'll treat me like a princess and take me out to the fanciest restaurants and treat me right. By night, you're my bitch and I'm your mistress. Also, you're going to get back to writing. You haven't published anything in quite some time. Why is that?"

"That's none of your business," I growl.

"It certainly is. You're my new sugar daddy. You are my business. Now let me finish with the rules. I'll be running the finances from now on. Your bank accounts and money will be in my control. In fact, tomorrow we're going to the bank and you're going to add me to your accounts."

"Why would I do that?"

"Hello, don't forget about the video. Or the fact that I could easily transfer all your cash out of each of the accounts."

"You're not making this easy."

"Neither did you last night. Now, onto the next rule. You will quit drinking and any other drugs you're taking. Got it?"

I nod. "Now you're starting to understand. Although, I prefer you give a verbal acknowledgment."

"I understand."

"Good, but next time refer to me as Mistress. At least when we're alone. When we're out in public, you can use pet names or my actual name. But you will show me respect and you will treat me like your girlfriend. Now, what do you say?"

I grit my teeth. "Yes. Mistress."

"There, that wasn't so hard, was it?"

I don't even answer. "Now, you're not going to do anything stupid once I release you, are you?"

"No Mistress."

"I want to believe you, but you did lie to me last night. Just to make sure you don't do anything stupid, I'm going to upload this video and schedule it to post on your social media accounts. If you behave, I'll take it down before it goes public. Got it?"

I glare at her. "Yes, mistress."

"That's a good boy," she says. "Now this is the beginning of our new life together. Aren't you excited?"

Chapter 2: Moving In

"This place is a mess!" Cindy says as we enter my penthouse. Even after she untied me, I still had to listen to her. I had to listen to her unless I want my world to end. How the hell did I get myself in this position? If she releases that video, I'll make her pay, I swear. I'll figure out some way out of this. We made a stop at her place and she made me pack up most of her shit. It surprised me to find that there wasn't much there. She's rather neat and kind of a minimalist. I've always thought hookers were rather dirty hoarders. I guess I'm wrong. She did have a fair amount of books though... It took me several trips to load them all.

"I'll call and get someone to clean it up," I sigh.

"No... that won't do at all. You're going to clean it up, maybe you'll learn to take better care of it going forward," she says.

"What? That's a ridiculous waste of time," I say.

"Don't argue, remember who's in charge here," she says, crossing her arms against her chest, pushing out her boobs. Naturally, the view pulls my eyes to it. "Hey, my eyes are up here."

I look up at her. "Now I suggest you get to work while I get myself settled in."

I let out a long sigh. "Just let me get some Advil first."

"That's all your taking. Remember, no drugs and no alcohol. Got it?"

"I got it," I growl. If that bitch thinks she can tell me what to do, she's got another thing coming.

Once I down the pills, it takes me nearly all day to clean the penthouse. The kitchen was a mess with dirty dishes stacked up and moldy food all over the place. The hardwood floor had to be scrubbed. The bathroom needed a lot of work. The toilet was clogged with all the puke I hurled up yesterday morning. Hair all over the sink. Both the jacuzzi and the shower needed a deep cleaning. It took forever to scrub down the shower, especially those stupid stones. I had to pick a place with such an intricate decor. Cindy through a fit when she saw the bathroom. She also fussed over my bedroom.

"You're going to change out those sheets and throw them away. That's so disgusting. I'm having second thoughts about this arrangement. I should've realized you were such a pig," she says.

Once I finish cleaning. She makes herself at home in my bedroom. "This will be my bedroom from now on."

"And where am I sleeping?"

"Don't you have a few spares? This place is big enough. Although, you should sleep on the floor since you're such a pig. In fact, that's what's going to happen. Until you can be a good boy, you're sleeping on the floor beside my bed. I'll let you get yourself a small mattress. I don't want you to get a stiff back. If you are good, I might just let you sleep in the bed with me, but I doubt that'll happen anytime soon. You still have a horrible attitude," she says.

I grit my teeth. I just have to put up with her until I figure out a way to get rid of her. And I will get rid of her. She rifles through my closet and my dresser. Taking out all the clothes and throwing them into a pile. "Oh, and by the way, you're taking me shopping later today. I'm in such a need for new clothes, most of mine were borrowed. And from the looks of it, you could use a new wardrobe as well."

"Are these your ex-wife's clothes?" she asks as she goes through them.

"Don't touch them!" I snatch Maria's dress from her.

"Wow, someone's not over the breakup. I'm surprised she left them here. They're quite nice," she says. "If you're ever going to move on, you're going to need to do something with them."

"Just leave them alone," I say.

"Fine, but we'll have to address it eventually," she says. "Now, where does the magic happen?"

"What do you mean?" I ask.

"You know. Where do you write your books?" she asks. "Ever since I read the first Aratheon book, I've been dying to learn how you do it. Of course, back then I didn't know you were such an asshole."

"I didn't know hookers could read," I mumble as I walk out of the bedroom.

"I heard that. That will cost you."

"And what exactly can you do to me? You've already taken over my life?" I ask.

"Oh trust me, I will find a way to punish bad behavior. Speaking of which, we're going to need to do some redecorating. I'm going to put in a BDSM dungeon," she says.

"What?" I ask.

"Did I stutter? A dungeon so I have many different options to punish you with. I'll show you the true meaning of rough sex," she says.

I swallow the lump in my throat.

"Now give me the official tour," she says.

I take her up the stairs to my office. The walls are lined with books and the wooden oak desk sits in the center with my laptop sitting with a thick layer of dust on top. "Seems like you haven't been in here in quite a while. That's going to change. Starting today, you're getting back to work. You still have to finish the Voyage series. Captain Azariah is one of my favorite characters. Although, so is Eloimaya. To think a douche like you created them."

"Are we done here?" I ask.

"You aren't, that's for sure," she snaps back. "But let's continue the tour. Please tell me you have a few spare bedrooms."

I don't respond, I just walk out.

"I'm definitely going to make quick work of those books you have in there. That's for sure," she says. "I guess that's one thing we have in common."

"One of the few," I say.

"Oh, I doubt that," she says as I open up a door to a spare bedroom.

"This room is empty," she says. "And half-painted sky blue. I knew you were lazy, but this takes things to a whole new level. But at least it saves us some work. This will be our new BDSM dungeon."

"No! Not this room," I say. "Don't touch this room."

"Are you serious? You have an entirely empty room here. You can't just leave this room empty," she says.

"Just leave it alone," I say.

"Fine, we'll talk about this room later," she says. "What else do you have in here?"

I take her to the next spare room. "You can have this one," I say.

"I suppose this will do. You'll have to repaint it. I'm thinking hot red. Or black maybe? The bed can stay. Now, do you have an exercise room?"

I nod. We head down the stairs to the bottom floor. "Fuck me, this place is huge. And to think you live here all by yourself. That must be lonely."

I ignore her comments as we enter the rec room which contains a hot tub and an exercise room. Maria liked to stay fit. "Wow, this is amazing. I wasn't expecting it to be so stocked. Especially with the gut you've got. Fortunately, it's not that bad. Nothing some sit-ups and planks won't erase. You and I are going to be spending a lot of time in here. After All, a girl's gotta stay fit. And I'm definitely going to be spending a lot of time in the hot tub."

"What else do you have?" she asks.

"There's also a small movie theater over here," I say, leading her over past a door into the theater room.

Her eyes go wide. "My god. This place is heaven."

No... It used to be heaven.

"Any more rooms?"

"Just another spare bedroom down here. And one more on the top floor. There's the flower garden on the balcony. The kitchen, dining room, living room, and Maria's office."

"We can keep those as spares for now. So Maria's your ex? Can I see her office?"