Skyscraper Cinderella

by K. Webster

  “Perfect. Now come closer.”

  Her movements are sluggish and awkward as she learns to walk with a plug in her ass. She finally comes to stand between my thighs. I reach forward and tug at the tassel hanging from her pussy, loving the cry of pain that erupts from her.

  “You do the ones on your tits,” I instruct. “Don’t stop until I tell you to.”

  She nods and gently tugs on the tassels, shuddering at the sensation. I tug at my cock in tandem with the way I pull on the tassel on her clit clamp. Despite the pain, within seconds she’s crying out as an abrupt orgasm floods through her body. Before she comes down from her high, I pull off the clamp. I’m sure all the blood is rushing to her clit now, and it must be painful based on the way she chokes on her tears.

  So. Fucking. Perfect.

  “On your knees,” I growl. “You like it when I hurt you, don’t you, Ash?”

  She shakes her head in vehemence.

  “You’re a fucking liar,” I say with a wicked grin. “You love when I humiliate you. You want me to call you terrible names just as long as I remind you who you belong to.”

  “Fuck you, Win.”

  “On your knees, asset.”

  “Asset?”

  “The help. Toy. Plaything. Whatever the fuck you want to call yourself. Do it.”

  She flips me off but falls to her knees as I stand. I paint her pretty lips with my cock that leaks with precome. Her tongue darts out, but I pull away.

  “No, little girl. You get what I give you. Right now, I want to see your face dripping with my come. You haven’t deserved to get it on your greedy tongue.”

  Her hazel eyes flare with fury as she glares up at me. It makes me wonder what’s going on in that head of hers. Is she angry because this darkens her fantasy of wedding bells and happily ever after like Nate suggested? Perhaps she needs a little reminder that I pay top fucking dollar for her humiliation. She’ll have to chase the white picket fence and perfect husband dream once we’re done with our dirty games. Until then, she’s mine to do whatever the hell I want with.

  “You’re a poor little girl whose daddy doesn’t love her anymore. She has to find a new daddy. One who’ll buy her pretty things and tell her she’s beautiful.” I let out a dark chuckle. “You just want to be loved.” I stroke her wet hair. “Sorry, little one, but you found the wrong daddy. I just want to hurt you and humiliate you and shame you. I’m not built to love so if that’s what you’re thinking you’ll get out of this, you’re wrong. I’ll play with you like I’ve done everything in my life, and when I get bored, I’ll find something else to entertain me. Maybe next year it’ll be a yacht. This year, it’s you.”

  A cruel, yet necessary reminder of exactly what this is between us.

  Her eyes flood with tears, and she’s never looked so pretty.

  “Beg for my dick, you poor girl. Beg for it.”

  “No,” she chokes out.

  “I’m paying you to beg. That’s all this is. You serving me. It’s your job.”

  “I hate you.”

  “Your pussy is slick, and your ass is filled,” I rumble. “The last thing you’re feeling is hate. You wish I’d stuff this cock in your tight, almost virgin cunt.”

  “Fuck you, Constantine!”

  “You want that, baby, because then you can start planning the wedding. Am I right? You think if I fuck you, I’ll put a ring on it?”

  A tear races down her cheek. “I would never marry someone like you.”

  “Beg. For. My. Come.”

  Another tear. “No.”

  “It’s all or nothing, Ash. Don’t go weak on me now. You’re so close to forty fucking thousand dollars. You’re not too proud. Think of your career one day.”

  She sobs. “Please.”

  “Good girl,” I grunt. “Such a good girl.”

  My come shoots out hot and violent, hitting her eyebrow and then her cheek. With each spurt, I coat her pretty face in my seed. As soon as I’m drained and my dick just drips, I use my cock to smear the come in, reveling in her shocked gasp. I smack her mouth with my dick before pulling back.

  Per our agreement, I take a few pictures from her phone so she won’t forget every filthy thing we did. Long after this thing between us is over, she’ll have this moment stored in her memories—and the cloud for that matter—to get her through her boring missionary sex with her future Prince Charming. I’ll be the villain who haunts her fantasies when she has to touch herself, searching for one ounce of the pleasure I used to freely give.

  “Clean your face up, Cinderelliott. Let’s hope you clean yourself better than you clean my office. You’re a fucking mess.”

  CHAPTER EIGHTEEN

  Ash

  I run into the bathroom, slamming the door behind me. When I catch a glimpse of my messy face in the mirror, I cry harder.

  What am I doing?

  I just allowed him to humiliate me for forty thousand dollars.

  It was horrible.

  Turning on the sink, I quickly splash water on my face to wash off his come and my tears. I continue to cry, horrified at my actions as I scrub my face clean. I’m just turning the sink back off when I sense his presence.

  “Go away,” I sob, unable to meet his stare in the mirror.

  “Look at me.”

  I shake my head, sending more tears flowing down my cheeks. “No.”

  He grips my hips and twists me around to face him. His expression is pinched slightly, an unusual one on his normally cool features. With a clean towel, he dabs at my face, drying it. I meet his blue eyes and get lost in them.

  I don’t understand this man.

  I thought I could play in his league, but I am so out of my depth here.

  “You’re brave,” he murmurs as he drops the towel at our feet. “And beautiful.” His fingers brush back my messy hair. “And mine.”

  My bottom lip wobbles. I have nothing to say to him. His words mean nothing to me.

  He unclamps each nipple clamp, tossing them to the ground. My nipples throb, but I refuse to wince with him staring holes into me.

  “Time for bed, little one.”

  He takes my hand and guides me out of the bathroom. I hate that my heart flutters a little at his gentleness. The overhead light has been turned off in the bedroom, the box and toys are gone, and the phone is no longer recording. He’s already pulled back the covers, and the soft bedside light is the only light in the room. I fall for his stupid tricks, because my heart skips at the way he’s taking care of me. Once I’m in the bed, he pulls the covers over my naked body. The butt plug feels strange, but I’m already getting used to it.

  “Goodnight, Ash.”

  “Can I sleep in your bed?” I blurt out, my eyes burning with tears.

  He tenses, his expression turning cruel again. “That’ll cost you more than you can afford.”

  Like a ghost, he vanishes. The door slamming shut signifies his exit, making my entire body shudder. I turn off the light and give in to my sadness. Gut-wrenching sobs leave me as I wonder what the hell I’m supposed to do right now. I feel so… used. I feel dirty. I’m so tired. I’ve only known Winston a few days, and he’s drained me of everything while he fills my bank account up. I’m not sure the tradeoff is even worth it.

  I’m almost asleep when the door creaks open. Soft footsteps pad into the bedroom. The covers pull back and then his large body sinks into the bed with me.

  “Come here,” he instructs. “I can’t sleep with all that crying.”

  I hate him right now.

  I hate myself even more for rolling toward him and curling my naked body around his almost naked one. His strong arm wraps around me, hugging me to him. As I breathe in his masculine scent, I relax in his hold. He lazily teases at my hair.

  “Tomorrow, I need to leave,” I whisper. “I can’t do this.”

  “I wanted you because you’re tough, Ash. Don’t grow soft on me now.”

  More tears leak out. “I’m not as tough as I look.” />
  “What do you need, love? Kind words? Those won’t come for free. It’s another piece of this game we can negotiate though.”

  “I have to pay you to be nice to me?” I scoff. “Asshole.”

  “There’s my fiery girl. Come to work with me tomorrow as my personal assistant. Be prepared to do actual business. Promise me this, and I’ll give you what you want.”

  I hold my breath wondering if I can do this. Finally, I exhale and nod. “Okay.”

  “Good girl,” he croons. “Such a dutiful, sweet girl.”

  His stupid praise that I basically had to pay for washes over me like a cleansing rain. He rolls me onto my back, and then his urgent lips are on mine. Each kiss is sweet and gentle. I hate how it thaws my heart toward him. It’s all a stupid game to him, and yet I need it every bit as much as he needs to humiliate me. We both have our kinks.

  “So pretty. So perfect. So mine,” he murmurs between kisses. “I want to keep you forever.”

  We kiss for what feels like hours as he whispers assurances that somehow make me forget every horrible thing he said and did to me. When I’m relaxed and content, he pulls away, kisses my forehead, and then leaves the bed once more.

  This time, rather than crying, I fall asleep with his kisses lingering on my mind.

  * * *

  Halcyon is incredible. Seeing it bustling with activity rather than alone at night while having to clean it is something else. I always resented the people who worked here as I emptied their trash and dusted their offices, but seeing them in action has me gaining respect for each of them.

  Especially Winston.

  I have mixed feelings about last night. On one hand, I want to leave while I’m ahead. I’m more than capable of paying for my first year of college now. It’s a great start, and I can relax. I’ll be able to apply for loans for the next year. There’ll be no reason to play his crazy-ass games anymore.

  But another part of me realizes I was just being emotional last night. Winston is a cold, calculating bastard, but he’s not heartless. He’s come to my rescue on more than one occasion. Whether he’ll admit it or not, he cares. His kink is fucked up and borderline cruel, but he never physically hurt me, and I agreed to it all.

  He chose me because I’m strong.

  Because I can endure his wicked games.

  A worthy opponent.

  As I walk from the copy room back toward Winston’s office, I feel empowered. Yes, Winston Constantine wants to play horrible games, but I played a round with him and survived.

  I can do this.

  Each of the secretaries are friendly, but Deborah is frigid toward me. When she sees me, her lips press together, and she looks away from me.

  “Hi, Deborah,” I say, forcing a smile.

  “Mr. Constantine is in a meeting now.” She purses her lips. “You may have a seat and wait until he’s done.”

  “But he asked me to make these copies for his meeting—”

  “He’s asked to not be interrupted,” she snaps. “Take a seat, miss.”

  Someone whistles, and I lift my gaze to see Perry waving at me from inside an office. I grit my teeth to keep from mouthing off at Deborah. Without letting her know how much she pisses me off, I walk over to Perry’s office.

  “Shut the door,” he murmurs.

  I close it behind me and have a seat across from his desk. “Is she always a bitch?”

  “Always,” he confirms with a grin. “It’s just Nate in his office. Deborah is on a power trip. Trust me, Winny will have her ass for that little stunt.”

  “Really?”

  “He’s obsessed with you.”

  “He pays me well.”

  He smirks as he crosses his arms and leans back in his chair, studying me. “We both know you’re more than an employee to him.”

  I’m reminded of what Nate said to me yesterday. How he thinks I’m trying to get Winston to marry me. It unnerves me.

  “Nothing more,” I assure him. “Just doing my job until college.”

  “I see,” he says, a frown tugging at his lips. “Well, if you ever need help or someone to back you up when Deborah is being a bitch, come see me.”

  He’s no longer the smitten, flirting guy he was at the club the other night. It relaxes me considerably.

  “I’m a newbie around here. You sure you want to trust me?” I lift a brow at him.

  “You hooked the impenetrable Winston Constantine. If you got inside him, you’re something special to him, which means it’s my duty as his brother to look after you. Deborah can fuck off. She just wishes she were you.”

  Perry picks up his phone and texts someone. Then he starts to whistle. Not a minute later, the door flings open, hitting the wall with a loud bang. Winston prowls in, a furious glare on his handsome face.

  “Are we taking a break to chit-chat, Miss Elliott?”

  I narrow my eyes at him, ready to bite back, but then I realize his lips are curled in amusement. “Asshole.”

  Perry snorts out a laugh. “I like her.”

  “You would. You’re both children. Let’s go, Miss Elliott.”

  I rise from my seat and get a tiny thrill when Winston places a possessive hand on my lower back. He guides me out of Perry’s office. When we make it to his office, he stops to speak to Deborah.

  “In case it was unclear,” he hisses in a mean tone, “Miss Elliott is my personal assistant. That means she is to assist me during my meetings. She assists me always. Do not ever shoo her away again.”

  Deborah’s face blanches. “I’m so sorry, sir.”

  “You’ve been saying that a lot lately.”

  He walks me into his office and then shuts the door behind us. After he grabs the papers in my hand, he sets them down on the desk.

  “Is your butt plug in?” he asks, throwing me off.

  “Yes,” I whisper. “I took it out this morning like you told me to before my shower and then put it back in before we left.”

  “I don’t believe you.” His dark blue eyes glint with challenge.

  “Too damn bad.”

  He pulls out his wallet, fishing out a wad of bills. “This says you’ll prove it to me.” With a flick of his wrist, he sends the bills fluttering to my feet. “Bend over my desk, lift your skirt, and spread your legs.”

  “Win!”

  “Oh,” he taunts. “I forgot.” With sarcasm so thick, I want to slap him, he says, “Please my darling little lovebug.”

  “You’re an epic dick.”

  “So I’ve been told.”

  “Say it and mean it,” I challenge.

  He steps closer until his front is pressed against mine. Gently, he strokes his fingers through my smooth, flat-ironed hair with one hand and gently cups my jaw with the other. I meet his intense stare.

  “You’re so hot today it takes incredible control not to fuck you,” he growls. “I want to do it with the door open so everyone knows you’re my fucking girl.”

  My stupid heart does a flop. “Keep going.”

  “Spoiled,” he gripes, though his eyes twinkle with amusement. “You make me weak, beautiful. So fucking weak.”

  His words don’t feel fake, which confuses me.

  “You, weak?” I bark out a laugh. “Never.”

  He presses his lips to mine, ravishing me with a devastating kiss. I’m so caught up in his kiss, I forget where we are, clinging to his suit jacket, wishing he’d strip me now.

  “Obey me, lovely girl, and I’ll take you someplace nice for lunch.” He trails kisses along my cheek to the side of my neck. “Do as I say, and I’ll buy you whatever you want.”

  I moan when he sucks on my flesh. “Winston.”

  “Yes, good girl?”

  “You’re going to ruin me.”

  “Why’s that?”

  “Because your lies feel like truth.”

  “I look forward to making you cry and beg.” He nips at my neck. “Now bend over my desk, and show me your ass. Enough talk. I’ve given you your sweet words.
Give me your sweet ass.”

  I cry out in surprise when he spins me around. My palms hit the surface of his desk with a slap as he pushes me down. A tremble ripples through me at being bent over and at his mercy.

  “Show me.”

  I roll my eyes at his bossiness and yank my skirt up over my ass. His deft fingers hook onto my panties, dragging them down my thighs. They fall to my ankles.

  “Rest your face on my desk and use both hands to show me your butt plug,” he orders. “Be a good girl, Cinderelliott.”

  I cringe at having to expose myself so crudely, but something inside me craves his approval. “Are you going to fuck me?”

  He laughs. “Always so eager. No.”

  I flip him off, earning more laughter, before gripping my ass cheeks and pulling them apart. Pressure is applied to the butt plug as he pushes against it.

  “Are you happy?” I grumble. “I’m not a liar.”

  “No, you’re not,” he agrees. “In fact, I think I should reward you, sweet girl.”

  I shiver at his words. “Oh yeah?”

  “It’s a freebie.” His fingers brush against my pussy. “You want a freebie, beautiful?”

  “Y-Yes,” I whisper.

  “Beg.”

  “Please fuck me.”

  He smacks my butt cheek hard, making my ass clench and sending strange sensations shooting through me. “The freebie isn’t my dick, greedy girl.”

  “You’re a tease, Win. A fucking tease.”

  “Beg me to put my fingers inside you.”

  “Please, for the love of God, finger me.”

  He chuckles as he runs his knuckle across the opening of my pussy. “You’re so wet. Are you always this horny, Miss Elliott?”

  “Only since I met you.”

  “Good answer,” he croons as he pushes a finger inside me. “Fuck, look how tight you are.”

  I gasp as he slowly fucks me with one finger. With the butt plug inside me, it intensifies the feeling.

  “I bet that pencil-dick boyfriend you had didn’t even properly break you in,” he rumbles. “My dick is going to split you wide open, baby. It’s going to hurt. You’ll cry because you’re just a little girl who wants a big man’s dick but she’s too small to take it.”