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?”
“No. Just leave the room alone,” I say.
She lets out a sigh. “You know you’re going to have to move on, right?”
I ignore her. “Fine then, show me the kitchen, dining room and living room. Oh and the balcony.”
I take her up to the living room which was all Maria’s design. “There’s no way you were able to design this, it must be Maria’s work. It’s elegant. I love the white and gold mixed with red. The wood flooring really pops along with the white fur rug. It matches the white couches and the white lounge chairs. Maria at least had taste,” she says.
I take her to the kitchen and she beams. “I love it. It goes with the living room then. White cabinets, wood flooring.A big stainless steel fridge. Marble countertops. This I can deal with.”
We go over to the dining room. “It’s beautiful. Is this mahogany?” she asks, pointing to the table. I nod. “It’s certainly big enough.”
We walk out onto the balcony. “Serious? You’re just going to let all these plants die? That’s one thing that’s going to change, you’re going to take care of all these plants every single day. I want a beautiful garden out here.”
“Alright, let’s go shopping. We’ll stop by the bank on our way back. Then you’re going to be repainting one of the guess rooms. I want a dungeon by the end of the night. You can start writing tomorrow. I also want a hot shower later. My muscles are so tense. And my ass is still sore from last night. I can only imagine how yours feels. I suggest some preparation H. You’re going to need lots of it. Especially for later. I’m not done with that ass of yours. Be a good boy and I can make it hurt a lot less. That’s more than you deserve.”
I let out a sigh. Will this torture ever end?
I take her down to the parking garage and we get into the SUV and head out to the shopping mall. I follow her around the shopping mall for nearly 3 hours as she picks out different clothes for both of us to try on. Even I can admit, she looks damn good in just about everything she tries on. Especially the nice bright yellow dress that comes down to the middle of her thick thighs. Of course, she ends up buying it. She also buys a load of clothes for me. Forcing me into them. Making me look like the cliche author all dressed in Polo.
By the time we finally finished shopping for clothes, I’m buried in bags. I dropped over 4 grand in cash. She tells me it’s not like I’m not loaded. It’s barely a drop in the ocean for me. “Besides, you’ll be coming out with a new book soon,” she says, throwing me a smile as bright as her new dress. As long as I am being honest with myself, I do like the way she smiles. For being a prostitute, she has such an innocent smile.
Once I get everything in the car, she makes me drive her to a shop in a sketchy part of town. Of course, it’s a sex shop. She gives me a look as she gets out of the car. “Are you coming?”
I relent and follow her in.
“Nina!” a woman with tattoos, black hair with red tips and pale white skin says as we walk in. I’m confused.
“Audrey! It’s good to see you again,” Cindy says.
“Who’s the new boy toy?” she asks.
“This is my boyfriend, Roy,” Cindy says. “Roy, this is my good friend, Audrey. She owns this shop.”
“It’s nice to meet you,” I force out, trying to be the least bit pleasant.
“God, Nina, you’ve outdone yourself with this one. He’s hot,” she says.
“And he’s a writer,” she says, attaching herself to my arm. “A successful one.”
“Good for you,” she says. “I’m so happy you’re off the street.”
“Thanks, love.”
“So, what brings you here? Are you two trying to spice things up?” she asks.
“Oh for sure. I’m getting back into the BDSM lifestyle. Believe it or not, Roy here is a huge submissive. It’s hard to tell by looking at him, but he’s a total bottom,” Cindy or should I say Nina says, making my face burn hot.
“Is he now?” Audrey ask. “I would’ve never guessed. I would have totally pegged him for a dom.”
“He can be sometimes, but once I’m through with him, he’ll be my bottom sub for good and he’ll love it.”
“Who wouldn’t love being your sub?” the goth woman says. She leans into me and whispers into my ear. “You got really lucky having Nina be your dom. Couldn’t have picked anyone better. She can be sadistic, I’ll admit, but she can also be so kind and compassionate. And she always has your best interest at heart. She’ll take care of you.”
“Now, load us up with everything. Spare no expense,” Cindy says.
The woman’s eyes light up. “Oh my, Nina. You’ve really found a keeper.” Audrey gets to work and piles on the toys. Half of them I don’t even know what they’re for. I look over to Cindy and she gives me such a devious smirk. It actually sends a chill down my spine.
“You can leave out the masks, I’m not really into the whole gimp stuff,” Nina says, which is a relief to me. “Besides, he’s got such a beautiful face, it’d be such a shame to hide it.”
By the time we finish, I’ve dropped at least another 4 grand on sex shit. My bank account’s feeling the burn today. It takes me 4 trips to load it all into the car as Nina, Cindy or whatever her name is gets all chatty Cathy with Audrey. They glance at me with subtle smirks. I can only imagine what they’re saying about me.
After I get everything loaded, Cindy and I get back into the car, we grab a quick bite to eat and make our way to the bank. “Nina?” I ask.
“That’s my real name. Or at least the name I chose when I transitioned,” she says.
“And Cindy?” I ask.
“My street name when I’m… You know.”
“Oh.”
We pull into the bank. I can’t believe I’m about to do this. Adding a tranny hooker I met last night onto my bank accounts. This is absurd. Ludacris.
We walk in, my hands sweating. What if she drains my accounts dry? It takes us less than 20 minutes to add her to each of my accounts. I clench my jaw shut the entire time. She better not screw me over. I’ll figure out a way to undo this. I swear. Once we finish, we get back into the car. She’s practically skipping with a smile.
“We should stop and get some paint,” she says. “I’d like to at least get that room painted tonight.”
“Fine,” I sigh. We stop by the local hardware store and she gets 2 gallons of black paint, masking tape, plastic to put down on the carpet and cover the furniture and some brushes and rollers. After we get home and I haul everything in, she forces me to get to work on remodeling the “Dungeon.”
I take everything out besides the bed and the dresser. Thank god she liked the wood style of them, I was not in the mood to figure out how to haul them out. I put the plastic and cover everything before putting up the masking tape. I can’t believe I’m actually listening to her. Why am I doing this? God, if it wasn’t for that video and the fact she’s got access to all my accounts, I would’ve gotten rid of her by now.
After I get everything ready, I grab a step ladder and fill up a tray with black paint. She comes in wearing nothing but jean overalls cutoffs, showing her sun-kissed, smoothed olive legs. The straps barely cover her breasts. She looks at me with a raised eyebrow. “What? I’ve decided to come give you a hand. Besides, I kind of like painting.”
Even I can admit she looks damn sexy in that outfit. “Quit staring, you’re weirding me out.”
I snap out of my daze. What am I thinking? She’s a prostitute… Besides the fact that she’s a tranny with a bigger dick than me. What will my parents think of her? What if they learn the truth? My life is ruined.
I get back to painting, dipping my brush in the paint and meticulously painting the edges of the masking tape that covers the trim. Thank god she likes the carpet. I was not going to replace it. She gives my ass a slap. “You know… I think I’d like this a lot better if you are naked.”
“You’ve got to be kidding me,” I say.
“Not at all. You’ve got a nice ass. I can tell you used to be in great shape. That butt makes me want to fuck you,” she says, licking her lips.
“Is this how this is going to be?” I ask.
“You can count on it. Don’t act like you don’t like the attention. You were drooling all over me yesterday,” she says, pinching my ass. “Come on, take those clothes off. I dressed up all cute for you, the least you can do is show me that ass. If you do this for me, I’ll use lube tonight when I fuck you. I’ll even go nice and slow. I’ll be extra gentle.”
I let out a long sigh. Then I get up and strip. “That’s a good boy. Fuck me, that ass is to die for.”
“Are we going to paint or not?”
“Have at it,” she says.
I get back on my hands and knees and continue painting along the masking tape. It doesn’t take long before I feel her hands groping my ass. “Are you series?”
“What? I can’t keep my hands to myself,” she laughs.
“Do you want this done or not?” I ask.
“Oh, don’t be like that. Have a little fun,” she says.
“I don’t do fun,” I mumble. “At least not anymore.”
“Why do you have to be such a rude Roy?” she asks as she takes a paint roller and gets to work. Her lips curved in a frown as she lets out a sigh.
Great. Now I feel guilty. Letting out a sigh. I take the paintbrush and slap it against her leg. She looks at her leg and then at me. With wide eyes, her jaw drops to the floor. “Oh no, you didn’t.”
I stand up to my feet. “And what if I did?”
She takes the roller and runs it down my chest. “Then I’m just going to have to do that.”
I take the brush and attack her with it, getting her cute little outfit covered in black paint.
“You bastard,” she smirks. She takes the paint tray and throws it at me, covering me in black paint. I take the gallon of paint and walk towards her. “Don’t you dare!”
With a devilish grin, I splatter her with paint. Her entire front side is completely black. “You asshole!” she laughs. “You’re cleaning this up and getting me a new pair of overalls.”
“Fine,” I say.
“Now help me get into the shower without getting paint all over the place. You’re cleaning me off,” she says.
I take a rag and wipe what I can off her legs and hands after she takes off her overalls, revealing her naked body. We rush over to the spare bathroom and climb into the shower.
“Time to do your duties and clean every inch of my body, slave,” she smirks. I take the washcloth bathing it in soap and start to rub her soft skin clean, starting with her shoulders. She leans into my touch. I run the cloth down her back and over her supple ass. Fuck me. This has to be the best ass I’ve ever laid eyes upon. She looks back at me with one eyebrow raised. “Don’t get any ideas. In this relationship, you’re the one taking it up the ass.”
I spread her ass wide open and slide the cloth down between her cheeks. She lets out a whimper. “Although… I suppose if you’re good and submit to me completely, I might let you make sweet love to my ass someday in the near future. If that day ever comes, you’ll be a gentleman and be as gentle as possible.”
I only nod, too fixated on such a perfect ass to register what she’s saying. She turns around and nearly slaps me in the face with her big dick. “I think you need to give less attention to my ass and more attention to my cock.”
I look up into those dark eyes of hers as a sadistic grin curves her lips. “Go on. Give it a little kiss.”
“Seriously?” I ask.
“Of course. You’d have to know that at some point I was going to want you to suck my dick. Would you rather me fuck your ass?” she asks.
I let out a sigh and look over her big fat cock. Closing my eyes, lean up and press my lips against the tip of her dick. “I’ve been wondering, why are you into trans women? You don’t seem to even like cock? Most men just want us for our extra appendage. You seem to care less.”
I open my eyes and look up at her. “I don’t know. I… I was drunk and high. I guess I just wanted a quick fuck.”
“That can’t be the only reason. You can be honest with me. I’ll keep it between the two of us.”
I swallow. “I’m not gay if that’s what your thinking.”
“I never said you were. Just because you like trans women, doesn’t make you gay. I don’t care what anyone says, I’m a woman through and through.”
“Then what are you fishing for?”
“I just want to get to know you. The real you. I want to understand you.”
“I guess… I’m a little curious, that’s all.”
“That’s totally fine. If you behave, we’ll explore anything you want. Do you like cock?”
“I… I don’t know.”
“Well, now’s your chance to find out. Play around with my cock and discover what you like.”
“Why are you being so nice?” I ask.
She lets out a sigh. “When we first met, I found you really attractive. That was before you came off like an asshole. But you were also drunk and probably high. That’s really no excuse though. No one deserves to be treated the way you treated me last night, but I also discovered you are my all-time favorite author. I refuse to believe that my favorite author is this creepy asshole. I decided I wanted to give you a chance.
She runs her hand down my cheek, caressing my skin with her thumb. “I wanted to see if you could change and become the person I believed you to be when I read your books. Besides, if I’m being honest, I’ve always dreamed about what it would be like to have you as a boyfriend. You had to be the most romantic person the way you write. I wanted to know what it felt like to be one of your characters and to be loved so deeply.”
I climb to my feet and look her in the eyes. “What if you’re wrong about me?”
“Then I’d still have all your money and I could at least stop selling my body just to feed myself.”
I let out a sigh. “I’m not going to let you go back on the streets. You don’t have to blackmail me for that.”
Her eyes fall from mine. “I feel terrible about that by the way.”
“Then just delete the video and give me back my accounts.”
She backs away from me. “You’re not getting off the hook that easily. How do I know you won’t just fall back into a drunken stupor and kick me out or get rough with me? I’m not giving up my leverage until I know for sure that you’ve changed. Now let’s finish the room.”
She turns off the shower, gets out and dries herself off. “Oh, and by the way, you’re still going to suck my dick later unless I decide to fuck your ass instead. Maybe even both.”
I let out a sigh and get out. After we get dried off. We still have a gallon of paint left but I have to reapply the plastic everywhere. It doesn’t take long before we finish painting the walls black.
“Now, you’re going to take me out to a nice restaurant on a date. So clean yourself up, trim that facial hair into something nice and find something good to wear. I’ll be in the master bathroom to freshen up. Don’t forget to make reservations, I don’t want to wait.”
This woman is going to drive me crazy. She’s so hot and cold.
I make the reservations to a nice place downtown I used to go to on the regular. After I clean up I meet her downstairs. She comes out looking drop-dead gorgeous. She’s got on a red dress that meets the middle of those thick thighs. Her hair is done up in an elegant bun. Her red hot heels bring her up to eye level. She’s absolutely radiant.
“This is where you compliment me on how lovely I look,” she says.
“You look gorgeous. Absolutely radiant. I love what you did with your hair,” I say.
“Thank you,” she says with such a genuine smile. “It feels good to hear that. You clean up well. You look so handsome. Might need to get you a haircut though.”
I can’t help but smile. God, she reminds me of Maria. So upbeat and positive. Kind and caring. Doesn’t take shit from anyone. Goes after what she wants. Always pushing me to be a better version of myself. She always speaks her mind.
I hold out my arm, her smile deepens as she takes it. “Thank you.”
I escort her out to the car and open the door for her. “A true gentleman.”
“So where are you taking me?” she asks.
“A nice Italian restaurant,” I say. “It’s hard to get into, you have to make reservations weeks in advance.”
“So how were you able to snag a table?” she asks.
“I’m good friends with the owner,” I say.
I drive her downtown and pull up the valet parking of the restaurant. A guy in a tux opens the door for Nina as I get out and rush to help her up. I toss him the keys and he gives me a ticket. I place my hand on the small of her back and escort her in. We walk up to the host and I tell her about our reservations. “Just one second, sir.”
“Roy? No fucking way,” A voice that could only be Tom says. I turn to see him walking up to me as he pulls me into a hug. “I never expected to see you out in about. How are things? You look good. How are you holding up?”
“I’m doing better. Taking things one step at a time,” I say.
“Who’s the lovely lady?” he asks.
“This is Nina. She’s… She’s my girlfriend,” I say, as her eyes light up at my words. “Nina, meet Tom, he owns the restaurant.”
“Wow… So you must be the reason for Roy’s sudden recovery. I haven’t seen him look this good since… Well, since you know…” he trails off, his eyes fall away.
“Yeah, I guess you could say that. He definitely needed a wake-up call, that’s for sure. But it’s still a work in progress,” she says.
“Well, keep doing what you’re doing. It’s so good to see you are doing well. Are you writing again?” he asks.
“He will be. That’s for sure. We’re taking baby steps,” she says.
“Well, I’ll be. You better hold onto this one, Roy. She’s good for you,” he says. “Well, I’ll let you guys get to your dinner. I made sure to set a table aside for you when I heard you made a reservation. Let me know if there’s anything more I can do. It’s good to see ya, man.”
“You too,” I say.
The hostess takes us to our table and I hold the chair for Nina. “So… Are you going to tell me what he was talking about?”
“It’s nothing,” I say.
“Is it about your ex-wife?” she asks.
“Can you just drop it? I don’t want to talk about it,” I say, grinding my teeth. My hands clenching.
“You’re going to have to open up to me eventually. That’s how this is going to work,” she says.
“Whatever…”
“Don’t be like that.”
“How do you want me to be? Happy? Joyful? Tell me how you want me to be,” I spit out as I cross my arms against my chest.
“Well, you don’t need to cock an attitude. I’m trying to help you,” she says.
“You’re right. I’m sorry. It’s just, it hasn’t been easy. I just… Can we not talk about it here?” I ask.
“Sure, but can you at least promise to tell me?” she asks.
“Fine, I promise I’ll tell you when the moment is right,” I say.
“I’m going to hold you to it,” she says.
“I don’t doubt it,” I say.
The waitress came over and took our order for drinks. Nina told her we were fine with water. I give her a stiff look. The urge to have a drink is almost all-consuming. Just one drink wouldn’t hurt. “Actually, what do you have for liquor?” I ask.
“Actually, we’re both fine with water,” she says she shoots me a glare. I match her sour look with one of my own. The waitress looks at her then back at me. “You don’t need to have a drink. You’ve done so well lately, don’t ruin it with alcohol.”
I let out a long sigh. “Fine.”
A smile as lovely as a blooming flower in the sunlight washes over her face. “I guess I’ll give you time to look over the menu and I’ll be back to take your orders.”
The waitress leaves us as we both look over the menu. “Thank you,” she says. “I know it can be hard to quit.”
“Did you used to drink?” I ask.
“No. My parents both drank. My mother more so. She would drink herself into a stupor every night. My dad was more of a beer drinker. But when they were drunk enough, they’d fight. Sometimes the fights were pretty terrible,” she says.
“I’m sorry. This is the first time you’ve talked about your family,” I say.
“That’s because it’s kind of a sore spot,” she says.
“How so?” I ask.
“I’ll tell you as soon as you tell me about your ex-wife,” she says.
“Touche,” I say.
“Have you decided on what you’re getting?” she asks.
“No, not really, how about you?” I ask.
“I was thinking of ordering the lobster pasta,” she says.
“I’ve had that before, it’s quite delicious,” I say. It was Maria’s favorite dish.
“It’s settled then,” she says.
“I think I’ll get the same,” I say.
“Would you like to split it? There’s no way I’m going to be able to finish it,” she says. A smile sneaks out, Maria was the same way. She was never able to eat an entire pasta by herself.
“Sure.”
“What?” she asks.
“Huh?” I ask, looking up at her.
“You’re smiling about something,” she says.
“It’s nothing. It’s just… Maria used to order that and I’d end up eating half of it because she could never finish it,” I say.
Her face smolders like coals. “I would love to hear more about her,” she says.
“Like I said, the subject of Maria is a painful topic. I’d much rather avoid it,” I say.
“You can’t avoid it forever,” she says.
“You can’t avoid talking about your family either,” I say.
“Touche,” she says.
The waitress returns and takes our order.
Nina orders for the both of us.
After she leaves, our eyes meet once again. “So…” I say, twiddling my fingers, searching for something to say.
“Will you start writing tomorrow?” she asks.
“I suppose. Yeah. I guess I will. I usually like to do it first thing in the morning when everything is fresh,” I say.
“Interesting, I’d love to learn your process,” she says.
“Why? Are you interested in writing?” I ask.
“I don’t know. I love reading. Maybe I should give it a try. Besides, I need to find some kind of thing to contribute to the relationship. I know how it looks, but I don’t want to be a mooch. Besides, I’ve always wanted to run my own business. What better business than a publishing company,” she says.
I can’t help but chuckle. “Well, you did blackmail me into being your sugar daddy.”
“And I feel terrible about that,” she says.
“Well, have you ever tried writing before?” I ask.
“No. is it hard?” she asks.
“It definitely takes some practice. I had to write a lot before I could get to the level of having such success.”
“Duly noted,” she says. “Can I observe you while you’re in your process?” she asks.
“I don’t know. It’s hard to write with someone looking over your shoulder,” I say.
“Fair enough,” she says.
“Maybe you can read my work after I finish, be my second pair of eyes,” I say.
“Really?” she asks.
“I don’t know, we’ll see how it goes,” I say.
“So you’re telling me not to get too excited,” she says, crossing her arms against her chest. The way her boobs squeeze together grabs my attention.
“Right…” She’s got such soft and smooth skin. It’s hard not to notice. And her breasts are shaped like two perfect teardrops.
“My eyes are up here you know,” she says. I snap out of my trance and look up at her. There’s a subtle smirk on her face.
“Right, sorry,” I say.
“It’s okay, I’m used to it,” she says.
There’s a long silent pause before the waitress brings out our dish. She brings an extra plate for us and a complimentary basket of breadsticks.
“Thank you,” Nina says.
“You’re very welcome, let me know if there’s anything else I can do,” she says before leaving us.
After we divvy up the pasta, we dig in. “So, now that you have the luxury of a sugar daddy, what are you going to do with your time?” I ask, genuinely curious.
“I don’t know. I suppose I should find a passion. As I said, I don’t want to be a mooch. As I mentioned, I’ve always dreamed of being a successful business owner. I’d like to create something I can be proud of. I’d also like to do a lot of traveling. See the world and whatnot, you know?”
“Yeah, where would you like to go?” I ask.
“You know, I’ve never been to Disneyland before. I would also like to go to Comicon. It’s obvious, I’m kind of a huge nerd. Then I’d love to go to some tropical resort. Maybe, France? Travel along Asia. Maybe the Bahamas. Hawaii is a good possibility,” she says.
“Wait, you’ve never been to Disneyland? It’s literally right around the corner!”
“You know it takes money to get into there, right? I’ve always been poor. My family was broke and of course, my previous job doesn’t exactly bring in the money like you’d think it would. Especially when you have to pay someone for protection,” she says.
“Oh, I see. So… you had like a…” I look around to see if anyone’s listening.
“A pimp?” she asks. “Yeah…”
“How did that work out?” I ask.
Her eyes fall to her lap as her lips press together. “Jerry was a rather domineering man. He’d collect almost 80 percent of the money we made and also get special favors from us. He could be kind of an ass and made you feel degraded. Like less than human. But what choice did we have? You know? You needed protection. Without it, you’re helpless. Of course, you’re not exactly well off under his protection. He can be rather… cruel.”
“I can understand why you had to get out of that situation.”
She looks up and meets my gaze. “I still feel terrible for all this.”
“I deserved it. I feel terrible for hurting you,” I say. Her face steams hot. I feel the same way.
We finish eating and I pay for it leaving a nice tip on Nina’s insistence. I escort her out with her hand wrapped around my arm. After the valet gives us my car back, we make our way back to my place.
“Do you think the paint is dry?” she asks.
“Should be,” I say.
“Good, I’d like to try out some of the toys we bought,” she says with such a devilish grin.
“Is that so?” I ask.
“Fuck yeah, I still need to punish you for getting paint all over my overalls,” she says.
“After the dinner we just had?” I ask.
“It was lovely, don’t get me wrong. Thanks for that. I really needed it. And I truly enjoyed it. But I can’t let bad behavior go unpunished. Besides, I think you’ll enjoy it just as much as I will.”
“What do you have in mind?” I ask.
“Some bondage and a few spankings. I’m also thinking you should wear a collar at all times during our sessions and when we’re alone. One that says your my property,” she grins.
“You’re really into this BDSM, aren’t you?” I ask.
“You have no idea. Being a hooker, I’ve only ever been on the receiving end on most of these encounters. I’ve been degraded, humiliated, tied up, and dominated more times than I can count. I want to know what it feels like to be on the other side. I want to be the dominant one. The master or mistress. I never want to be someone’s whore ever again,” she says.
“Fair enough,” I say.
“You mean, you’re okay with this?” she asks.
“I don’t know. I can understand how you feel. I’m not sure how I’ll like being degraded and whatnot,” I say.
“I promise I won’t go too far overboard. I don’t want to end up like them. I just want to feel powerful,” she says.
“Okay,” I say.
“I’m surprised you’re taking it so well. I thought for sure you wouldn’t want to do it,” she says.
“I guess I deserve it. Besides, it’s not like I have a choice,” I say.
She lets out a sigh. “How about I’ll give you a safe word so if I do get carried away, you can just use the safeword and I’ll back off. That’s more than I ever got. Besides, I don’t actually want to hurt you,” she says.
“Okay,” I say.
We pull into the parking garage and I park the car.
“How about it whenever I go too far, you just said the word red line. That means I’ve crossed the line. How does that sound?” she asks.
“Sounds good,” I say.
I get out and get the door for her and help her out. She takes my hand in hers as we make our way up to the elevator. “You know, you’re really not the asshole I thought you were when we first met,” she says.
“Thanks, I guess. I was pretty drunk when we met.”
She laughs as we ride the elevator up. “Yeah, you were more than tipsy. I’m glad you didn’t get that drink. Thanks. You’re so much better off without alcohol.”
“Okay,” I say. “No offense, but I’m surprised you don’t do drugs. Being a hooker and all that.”
“Oh trust me, there were times where I considered it. I just didn’t want to be like my parents. Or the others. Most of them spend all their money on drugs and just continue the cycle of fucking for money and getting high. I had plans. I was determined to get out of there. It was only temporary for me. The more I was abused, the more determined I became. But fortunately, I guess I got lucky, depending on how you view it.”
I have to admit, the more time I spend with her, the more I find myself liking her. She has a certain charm to her. There’s no doubt about it. I just wish she’d delete the video and give me back my accounts. I suppose I could call the banks and change the passwords. And so what if the video got leaked. I mean for god sakes, it’s not like it’s the 60s anymore. But what about my parents? They would be mortified. Would my friends still stick around?
“What are you thinking about?” she asks. We get out of the elevator and enter my penthouse.
“Nothing,” I say.
She shrugs. “I had a really fun time today. For the most part. Thanks.”
“If I’m being honest, I had fun too.”
She smiles.
“So, will you ever delete the video and give me back my accounts?” I ask.
“Is that the only reason you were being so nice to me?” she asks. She looks as if she just got slapped.
“No. Not at all. I just… I don’t want that video getting out. If my parents saw that… They’d be mortified,” I say.
“So typical,” she lets out. “You were just acting to get what you want.”
“No. I wasn’t. I truly had a good time tonight.”
“And what would you do if I did delete the video and relinquished your accounts? Would you kick me to the curve like the tranny whore you called me last night?” she asks.
“No. I swear I wouldn’t!”
“For some reason, I have a hard time believing you,” she says.
“I swear. I won’t throw you out,” I say.
“Whatever. I’m going to go get changed, I expect the dungeon to be ready before I’m done. It’s time for your punishment,” she says.
I let out a long sigh as she heads up to my room. This woman is going to be the death of me. I head up to the “dungeon” and take out all the plastic wrap and clean up the paint supplies. After I get that finished, I bring up all the toys she bought with my money. I turn to see Nina standing at the door. My jaw drops at the sight of her. She’s got on a pair of black thigh-high boots. A black corset that doesn’t cover her teardrop breasts with diamond hard nipples. To top it off, she’s got long black gloves that almost come up to her shoulders. Her flaccid cock dangles between her legs uncovered. She wears a look of pure possession as she bites her bottom lip. “Why are you still dressed?”
“I… uh… I was getting your dungeon ready,” I stammer.
“Don’t speak, just get naked, my slave,” she says. I stand there dumbfounded. “Now!”
Jumping out of my trance, I quickly pull off my clothes. “Listen, Nina. I’m sorry. I didn’t mean to pressure you or anything.”
“I told you not to speak,” she says as she walks over to the bags of toys. After digging around, she pulls out a ball gag. Then she struts over to me. Her hand trails up my chest. “Open up.”
I don’t even hesitate, I just do as she says. She places the ball gag in my mouth and straps it tight. “You were doing so well. But… sadly, I’m disappointed with you. You don’t get the right to ask about the video. You lost that right last night. And it’s not your place to worry about the bank accounts anymore. I’m taking care of the financials from now on. All you need to do is focus on writing and my happiness. Creating stories and pleasing me is now your life’s purpose. Understood?”
I nod. This woman is completely crazy. And yet… I enjoyed being with her today. I’m not sure if that makes me crazy as well. She smacks my ass hard and grips my butt cheek, squeezing it tight. “Get down on your knees.”
I drop down in front of her. “This is your place in life from now on. On your knees pleasing me anyway I see fit. That doesn’t mean you can’t earn your way back up and stand at my side. As much as I am going to enjoy dominating you. I want a boyfriend that I can trust and one that will love me. Fortunately for you, I truly believe you’re capable of that. You just need the right motivation. Hence the dungeon.”
“Would you like to become my boyfriend and eventually my husband?” she asks. I find myself nodding. What is going on with me? Why do I find myself completely mesmerized by this crazy bitch? “That’s good to hear. I just wish I didn’t have any doubts about you. I’m still afraid that if I delete the video and give you back your bank accounts, you’ll go back to being a fuckhead.”
“We can’t have that, can we?” she asks. I shake my head no.
“I’m glad you agree. Now crawl over to the bed and lay down on your tummy,” she says. I do as she tells me to and crawl over to the bed. She gives me a hard slap on my ass. I get up and lay flat on the bed. I look back to see her digging through the bags. She pulls out cuffs and then walks over to me. She ties one end of the cuff to the bed and the other to my wrists and ankles. “There, that’s better. Now it’s time for your punishment. I was going to go easy on you for getting paint on me. In fact, it wasn’t really going to be a punishment as much as a lot of teasing. I actually had fun with you today as far as shopping, painting the walls and dinner goes. But you had to bring up the video and bank accounts. Why can’t you just trust me? Although, part of me understands. It’d be hard to trust someone that has to use blackmail, but in your case, you needed it.”
Her hand slides down my back and grabs ahold of my ass cheek. My mind races with all sorts of demented ideas of what she’s going to do to me. Some of them make my cock hard, others fill me with fear. “Since I can understand your apprehension at trusting me, I’m going to go easy on you for your first punishment. Well, I guess it’s more like your second punishment if we’re counting last night. You definitely deserved that one.”
She gives my ass a hard slap. “I’ve been thinking of all sorts of ways to punish you. Spanking you like the bad boy you are is always an option. But, I’m not going to damage this perfect ass. No. No. No. This ass is mine to fuck. Although, I could fuck you really hard like last night. That would certainly be very painful for you. But… I actually want you to enjoy having sex with me. I want you to want my dick in your ass. So that won’t do. Maybe some nipple clamps and a lashing? That could work. It’ll get the endorphins moving in your blood so when I fuck your ass the experience will be that much more pleasurable.”
She goes over to the bags and digs through them. She pulls out what she needs and walks over to me. I gasp as she puts clamps on my nipples. The sting makes me bite down hard on the gag. Then she brings down a flogger hard on my back. It stings. I grip the cuffs and clench down on the gag as my eyes shut in agony. The sting lingers on my back. She does it again and again. Over and over until tears fall down my eyes.
“There. I don’t want you to bleed. I think you understand now that bad behavior will always result in punishment. But don’t worry, my pet. Good behavior will also be rewarded. And you did a lot of things right today. So, for being a good boy for most of the day, I’m going to reward you by using lots of lube and I’m going to be extra gentle with you. I’ll also put some ointment on your back. She walks over and grabs two bottles. She then climbs onto the bed and removes her gloves, tossing them aside. “I can imagine your ass is still sore from last night. That’s what happens when you don’t use lube and ram your dick into someone’s asshole like a dog. Fortunately, I’m not going to do that this time. I’m going to teach you how to properly have anal sex so that both the giver and the receiver enjoy it.”
She rubs a cold liquid all over my back before she leans down and kisses both of my asscheeks. Then she spreads them apart. I feel her hot wet tongue drag up the crack of my ass, sending a tingle up my spine. She licks her way back down until her tongue meets my butthole. She circles it, making me wiggle in pleasure. She gives my ass a light slap. “Be still.”
I try not to move as her tongue pushes up against my rosebud. She slips it in making me gush with heat. A mix of excitement and fear rush through me like a waterfall of freezing ice-cold water. It feels so wrong and naughty and yet it also feels so right. My cock is as stiff as a steel rod. She starts sliding her tongue in farther, making me quiver. A moan escapes my lips. I grip the links binding my cuffs to the bed. I never thought that getting my butthole licked could feel this good. “You’re enjoying this, aren’t you?”
My yes comes out as a garbled grunt through the ball gag. “I’m glad. As I said, I don’t want to hurt you. To be quite honest, you have no idea how much I adore you.”
I can hear her opening up a bottle. I gasp as a cold liquid drips all over the crack of my ass. “I fell in love with you the first time I read your books. They were the only thing that made sense to me in this fucked up world.”
Her finger tickles my butthole, making me squirm in pleasure. “Never in my wildest dreams would I ever have thought I’d actually have a chance to meet you in person let alone get to have sex with you. Of course, I also never would have thought you were an asshole. But, I don’t think you’re truly are an asshole. Not really. I want to believe you’re in a bad place. Why else would you be in such a sad state? Why else would hurt another person?”
She pushes her finger up my ass. I gasp out, unprepared for the sudden intrusion. Drool drips down from the gag as she finger fucks my butt. Holy fucking shit. At first, it was uncomfortable, but it didn’t take long to feel like a fire had been lit inside me. “Roy, I know you’re not a bad person. I can see that in your books. A bad person wouldn’t be able to bring out emotions inside me I never knew existed before I read your books. How could a bad person create characters that are as deep as an ocean? How can an asshole write such a romantic love story?”
She slips in a second finger, stretching out my butthole a little more. “No. You’re not an asshole. You’re in pain, I can see that clearly, even if you won’t admit it. I’m going to help you, Roy. I’m going to heal your heart.”
She slides those fingers in and out, making all sorts of moans escape my lips. Her touch makes me melt. “It’s not going to be easy. But I’m not giving up and I’m not going to let you give up either.”
She adds another finger. “You got that? You’re stuck with me. But don’t worry, I promise if you trust me, we can find happiness together. I hope one day we can look back on this and laugh about it all.”
She pulls out her fingers. I look back and watch her squirt more lube into her hands. She lathers her big dick in it. It’s as hard as mine. I bite down on the ball gag. Fear grips my heart as I clench my butt cheeks. She gives my ass a slap. “Don’t tense up, it’ll only make it hurt. And the last thing I want to do is hurt you. Just breathe, okay?”
I nod and do my best to relax, filling my lungs with air. “That’s better. Now I’m going to take it slow and I promise to be gentle. Just remember to breathe and you’ll be fine.”
She leans down and kisses my shoulder as she slides her dick up and down the crack of my ass, sending a chill up my spine. I grip my bindings and bite down on the gag as her dick meets my asshole. She places her hand on my back as she starts to push her cock inside me. I gasp out in discomfort as her cock spreads open my butt. It feels like I’m taking a big shit.
“Breathe baby, just breathe,” she speaks so softly. Her voice is so soothing. All of a sudden, the tip of her dick slips inside me. I let out a long breath.
She holds the head of her cock inside me as she rubs my back. “There, the worst part is over.”
I let out a sigh of relief. Her touch is so soothing, the same with her voice. It drips honey. It extinguishes the tension in me. She takes her time sliding more of her cock inside me. I bite down on the ball gag. It’s definitely uncomfortable, to say the least. She lays down on top of me, pressing her breasts against my back. I can feel the heat of her breath on my neck. “Don’t worry, baby. I’m going to take it nice and slow. It’s going to feel so good.”
She bites my ear as she pushes more of her cock inside me. I curl my toes as she continues her conquest. This time she doesn’t stop. Continuing farther inside me until her hips meet my asscheeks. “That’s it, baby, I’m all the way inside you. That’s a good boy. Fuck. you’re still so tight. It feels so fucking good. Your ass is mine. All mine.”
She pulls her hips back, taking her dick out a few inches before she begins her descent. I moan out as her cock pushes up against a real sensitive spot inside me. Like a trigger, pleasure shoots through me. A moan escapes my lips. “Now you’re enjoying it. See how pleasurable anal can be when you do it right?”
She pushes inside me until her balls slap against mine. “Maybe if you’re a good boy. And I mean a really good boy. A fucking angel, I’ll let you have a second chance being on top.”
She gyrates her hips in circles, massaging that sensitive spot inside me. I squirm and pull at my bindings as the pleasure erupts inside me. I can’t help but moan like a bitch. I want to tell her to don’t stop, but it comes out as a garbled mess. She laughs. “You love it, don’t you? I bet you’ll be begging me to fuck you from now on.”
If it weren’t for the ball gag, I’d be begging her right now as she starts to slowly rock her hips back and forth, slowly fucking me inch by inch. “You want this don’t you?”
I nod my head without hesitation. She sinks her cock all the way inside me, making me groan out. “I want you so bad. Will you submit to me. Will you be all mine?”
I nod, frantically. Just don’t stop fucking me.
She undoes my ball gag and it falls from my mouth. “I want to hear you say it.”
“Please, don’t stop fucking me,” I beg.
She laughs, stopping the movement of her hips, lodging her cock all the way inside me. “I told you, you’d be begging me to fuck you, but that’s not what I want to hear. I want to hear you say that you’re all mine.”
I lean up and look back at her. Our eyes meet. I’m struck silent by her beauty. She absolutely glows radiantly with skin kissed by the sun. “I… I am all yours,” I breathe.
Her cheeks burn red. She leans over and places her lips on mine. She slowly starts to fuck me. I moan into her. Her tongue slips between my lips and I suck on it. I don’t know how much longer my stiff cock will hold out. She picks up the pace. Her thrusts become more wild. “Fuck me. Urgh. fuck. I’m going to cum,” I scream out.
She kisses me. “Fuck, let’s cum together.”
She lets loose on my ass. Sitting up as she grabs my hips and starts fucking me hard and fast, moaning with each thrust. I grip my restraints and hold on for dear life. The pleasure is so intense. So overwhelming, it practically blinds me. I scream out in ecstasy. I can’t hold on any longer. I clench down on her dick as sparks fly inside me. My cock erupts, blasting cum all over the sheets and my stomach. She screams out in pleasure as she slams into me, burying her cock deep in my bowels. A torrent of hot stick cum fills my ass. My entire body melts under so much pleasure. She continues to hump me as she deposits the last of her load inside me. She collapses on top of me. Both of us gasp for air. “That was… That was amazing,” I breathe.
“Did I just turn you into a bottom bitch?” she laughs, kissing my shoulder.
“I… I… um. I don’t know,” I say, catching my breath.
“Baby, there’s no shame in being on the bottom. I enjoy it most of the time. Especially with lube,” she says. “Admit it, you enjoy being my bottom bitch.”
“Alright. Okay. I enjoyed being your bottom… bitch,” I say.
She kisses me neck, wrapping her arms around my torso. She buries her face in the nape of my neck. I feel so warm underneath her. She makes me feel good. She kisses me again. “I enjoyed being your top mistress,” she laughs.
Finally, she pulls out of me. She gets off of me and walks out. “Hey! Wait a second. Are you going to untie me? My wrists are getting numb!” I yell.
A minute later, she walks back in with a towel. “Maybe, I was kind of thinking of leaving you there. You’re definitely not sleeping in bed with me. That’s a right you haven’t earned yet.”
She takes the towel and wipes my ass with it. Then she brings it underneath me and wipes off my cock. “Seriously?” I ask.
She gets up in front of me. “Would you mind cleaning off my cock for me?” she asks, presenting her dick in front of my face as she crouches down.
I flinch back in disgust. “You want me to suck your dick after it’s been inside my asshole?”
A devilish grin burns on her face. “Absolutely. Every good bottom bitch cleans his mistress’s cock after they receive a good fucking.”
I look up into her eyes. She has every intention of making me suck the cum off her dick. “If I do this will you untie me?” I ask.
“No, probably not. But you’ll make me happy.”
I let out a sigh and open my mouth. She gleams brightly as she leans down and slips her dick in my mouth. The taste is rather strong and salty. She runs her hands in my hair as she rocks her hips back and forth, sliding her flaccid cock in and out of my mouth. “We really need to work on your cock sucking skills. I guess that at least gets the job done.”
She pulls her dick out of my mouth and lays it on top of my face. “Don’t forget to clean my balls too.”
I lather her balls in a tongue bath, getting them nice and sloppy wet. She giggles and pulls away, climbing off the bed. “I can’t believe you did that. For some reason, I didn’t think you would.”
“Why would you make me do it?” I say.
“Just to test you,” she says as she unhooks my bindings. “You passed. It pleases me that you’d do that just to make me happy.”
After she finishes unbinding me from the bed. I get up, stretch and rub the feeling back into my wrists. She wraps her arms around my waist and buries her face in my chest. I let out a breath and hold her. She kisses my chest as she looks up into my eyes. “For the most part, I had a fun day today. Thank you.”
“If I’m being honest, I had fun too.”
She lets out a yawn. “Well, I’m tired. I’m going to bed. Don’t think just because I had fun that means you can come to bed with me. But since you were such a good boy, I’ll let you sleep on the floor next to my bed.”
“Seriously?” I ask, raising an eyebrow.
“Baby steps,” she says. “I’ll tell you what. Tomorrow, treat me to an all-day amazing date and I’ll let you sleep with me and hold me all night long. Okay?”
“So I really have to sleep on the floor tonight?” I ask.
“Yep. You’re lucky I let you sleep in the same room as me. Now if you’ll excuse me, I’m hitting the hay,” She says as she unwraps herself from my arms and heads out to my room. I can’t help but watch her ass jiggle with every step. She pauses at the door. “I almost forgot. I got you a collar. I want you to wear it when we’re at home.”
She heads over to the bag of toys and digs through it until she pulls out a leather collar. It has a dog tag on it. “It says my pet,” she giggles.
“Are you serious?” I sigh.
“What? Don’t you want to make me happy?” she asks. “It’ll make me so happy if you put it on.”
“Fine…” I sigh. She takes it and wraps it around my neck, binding it tightly, but not too tight. “Now let’s go make you a place to lay.”
“Am I like your dog or something?” I ask.
She laughs. “Don’t be silly. Dogs are so much cuter.”
“Really?” I sigh.
“I’m just kidding, you’re definitely my pet. That’s for sure. But you’re also my boyfriend, right?”
“I don’t have a choice, do I?” I ask as we walk into my room. My eyes glued to her ass.
“You always have a choice, but you only have one good choice,” she giggles. “Do you have a blowup mattress or something?”
“I have a mat,” I say.
“Well, go get it,” she says.
This woman drives me crazy and yet she makes me feel alive again. Once I get the mat, I make a bed on the floor next to my bed. How humiliating. And fucking stupid. I still don’t see why I can’t sleep in the other bed? She just loves torturing me. And yet, I… I enjoy it too. Not really the torture, just her.
After I get the bed made, she leans up kisses me. “Good night.”
Then she crawls into the big comfortable bed and curls up in the blankets. “Now be a good boy and turn the lights off.”
“Do you have my phone?” I ask.
“Yes, why?” she asks.
“I can turn them off with my phone,” I say.
She sits up and looks at me. “Really? No way.”
“Yeah, it’s the smart home feature. It’s an app that looks like a house,” I explain. She pulls out the phone and opens it. Her eyes light up as she turns the lights off with the phone. “That’s so cool. Lifestyle of the rich and famous. Well, good night.”
“Good night,” I sigh as I lay down on the floor. I’m going to need to really impress her tomorrow and I think I know just how to do that.
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