Blank Check

Story Info
What would you do?
2.6k words
4.46
8.5k
3

Part 1 of the 3 part series

Updated 06/09/2023
Created 01/31/2019
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

Joe was the hottest boss I'd ever had, and he flirted with everyone. So I wasn't necessarily surprised when occasionally he took notice of me.

"Hey, Sandra," he'd say, resting one hip on my desk and flashing me that killer smile. The one complete with dimples and deep, soulful brown eyes.

"Hey, Joe," I supplied, keeping my eyes on my computer screen.

"Want to come out with us Friday night?"

"No, sorry, I'm busy that night," I glanced at him, noting the humor in his eyes that never dimmed.

"Sure, no problem. Maybe next week?" The way he said it, it sounded more like an answer than a question.

"Maybe next week." Was I agreeing? I was definitely not agreeing.

"Great!" And with that, he floated off assuredly to his next proposition. I had to admit, he had an excellent body, and I had to admire that kind of swaggering confidence.

The next week, Joe was carrying an armful of folders and a large box of files. Slung across his arm was also an Armani jacket, so casually it nearly made me cringe. As he walked by my desk, something must have dropped out of the pocket. Moments later, when he had disappeared into his office, I looked down and noticed a leather black book, smaller than my hand, lying on the floor.

Discreetly, I speared it with my heel, drug it out of sight and bent to pick it up. Opening the first few pages, I immediately noticed the many names and numbers of many women who worked in our building and, figuring this was something better examined in private, quickly stashed it in my briefcase.

Blushing, I pretended to be busy at work and let my thoughts race. Was that what I think it was? This wasn't a man who was careless in business, but clearly, if this was some kind of little black book, he was obviously careless in his personal life. Someone in his position surely wouldn't keep something like that...

"Hey, Sandra!"

Startled, my hands jolted and spewed random letters across the proposal I was writing.

"Hm?" I glanced up as Joe leaned across my desk, resting his chin in his hands.

"I was hoping we could have a little talk about something. Say, tonight, over dinner?" He smiled and it was hard to break my gaze away.

"Sure," I managed, trying to look innocent.

"Perfect. The Ivy, off 38th. Eight o'clock."

"Sure."

He winked, like we had a secret. Then left.

Slowly, I packed up my things and decided to call it a day. I wasn't going to get anything else done here.

When I got home, I opened the book again. My name wasn't in it. Some of the names I knew, some I didn't. Some were crossed off. Then I noticed many of them had amounts listed next to them.

100, I read. 150. 125...

Hmm. While I raised an eyebrow at some, most of the names didn't surprise me.

Dinner was in two hours. What was I going to do?

After some thought, a smile crossed my lips. I went through my clothes, pulling out a sexy skirt and nearly see-through blouse with some spicy lingerie underneath. If Joe was looking for some kind of negotiation, that's what I'd give him.

---- x o ----

When she walked in, I didn't recognize her at first. The woman who usually dressed conservatively had on a skimpy little black skirt and silver top, unbuttoned and revealing something lacy underneath. Shapely, long legs tapered down onto a pair of black stilettos. I tried not to lick my lips.

"Hey, Joe."

"Hey, Sandra."

She smelled fantastic. Something dark and crisp and alluring. Her brown hair was down, her eyes smokey in makeup I'd never seen hear wear. I felt my cock twitch and tried to keep myself composed as I took her hand and kissed it.

"Shall we?"

I let the hostess lead us to our private table and ordered us some oysters and champagne. Of course, we had an entire balcony to ourselves, just as I had arranged it.

"So," I said conversationally, "It's been awhile since I hired you to work for the company. How are you liking your position?"

"Oh," she smiled, her lip gloss glittering in the dim light. "I think I like it just fine. But, of course, I'm always looking for new opportunities."

"That's just what I was hoping to hear."

I watched her sip her drink and eat delicately. She traced the top of her glass with her finger and I found myself mesmerized by her lips. They were full and thick, and shimmering wet with gloss. I'd always found her attractive, but with all her features embellished she was downright sexy. Delighted she had come to play, I'd let her think she had the upper hand. I had a feeling we'd both be leaving quite satisfied.

---- x o ----

"So, Sandra," he said.

"Yes, Joe?" I smiled.

"I think you have something that belongs to me."

"Oh," I reached into my purse, pulling out the little black book. "Do you mean this?"

I leafed through the pages once again, trying to contain my amusement. He'd clearly left it for me to find. But why? Intrigued now, I crossed and uncrossed my legs, allowing my skirt to hike up a bit further.

"What is it?"

He stared at me a moment, a smile playing across his mouth. He had a bit of stubble, making him look tougher and a bit more rugged. A bit more dangerous.

"I think you know what it is."

I smiled.

"I imagine a man in your position might find something like this a...sensitive matter. And I suspect you would like it back."

"Yes," he held his gaze, and I began to find this game very exciting.

"I may be willing to be discreet about this..." I set the book on the table. "For a price."

"I thought you might say that," he held my gaze, still giving nothing away. "What did you have in mind?"

"What's it worth to you?"

He seemed to consider for a moment, then stood, drawing me up as well. He reached around me and pulled me snugly against him.

"Hey-"

"I'll make you a deal," he said, his hands on my hips. "You give me the book back, and I give you a night you won't forget."

His hands began to roam higher, brushing under my blouse.

"No deal," I said. "I give you the book back, and you give me a promotion. And we forget I ever saw it."

I placed my hands on his chest to try to push him away, and he caught one and began to nibble on my fingers.

"The problem with that deal is, it doesn't include you. And I'm accustomed to getting what I want."

He leaned in and kissed my neck, his hands dipping under my blouse and his thumbs brushing just beneath my breasts. The man was sexy, I had to admit, and it had been a while, a long, long while, since I'd slept with anyone.

"You can't afford me," I managed as his hands became very busy and he began kissing his way along my neck.

"Name your price," he murmured, biting my earlobe.

I backed away, putting some space between us. I ran a hand through my hair.

"Listen, Joe, I've never done anything like this before."

"Then let's make it simple." He pulled out his checkbook, scribbled something on it, and handed it to me.

Stunned, I glanced down at a signed blank check.

"You can't be serious," I blurted.

"I want you, Sandra. One night. Name your price." He held out a pen.

I hadn't intended for things to go this way. I had wanted to dangle the bait in front of him, then walk away with my promotion and leave him with his secrets. But... glancing at the check, I felt a little lightheaded.

"Hold on a second," I held up a finger. "...what exactly are you proposing?"

He grinned, a sly toothy smile spreading across his face.

"You name your price, and in return, I get you for one night. What we do is entirely up to me. What we don't do, that's entirely up to you. And, of course, I get my book back."

Feeling curious, brave and a little turned on, I contemplated the deal. Then, I wrote in ONE MILLION and a one, followed by six zeroes. I held it up for him to see.

"How about this?" I said smugly.

"Done," he said, picking up the black book from the table. "Let's go."

My jaw dropped as he took my hand.

"You can't be serious."

"Darling, I'm always serious when it comes to business."

--- x o ----

I was still stunned as I found myself standing in his penthouse, overlooking the city. The check was tucked in my purse, and I was in shock. This couldn't actually be happening. He handed me a glass of wine and looked me up and down with those dark brown eyes.

"You don't actually expect me to believe you're going to go through with this."

"Do you happen to know what my net worth is?" he countered, pulling me close again and beginning to unbutton my blouse.

"Well, yeah, but..."

He brushed the sleeves over my shoulders, then let my shirt fall to the ground, kissing the exposed skin above my bra.

"Trust me, Sandra, I'm good for it."

He trailed open mouthed kisses across my breasts, then up my neck.

"Last chance to back out," he whispered, his hands roaming down to gently cup my ass. "Do you agree to our deal, or not?"

He gave my ass a squeeze.

"Okay, all right. I agree."

"Good girl," he murmured, turning me away to pull me back against him. He bit my shoulder, the fingers of one hand splaying across my stomach as his other hand pulled down my skirt.

He made an approving sound at my choice of underwear: a black lace thong. I started to reach for my shoes before he stopped me.

"No, leave the heels on."

One hand keeping me pressed against him-I could feel his erection against the small of my back-he used the other to toy with the thong, brushing his hand along the front of my thighs.

I squirmed as his fingers roamed the edges of the fabric, his hand leaving my belly to squeeze one breast, his breath heavy on the back of my neck.

"You are so gorgeous," he said softly in my ear. His fingers dipped inside me, gently probing, teasing. I groaned.

He unfastened my bra, then turned me around and kissed me, gently at first and then more urgently.

"Tell me to stop, if you get uncomfortable."

Then he pushed my back against the wall and dropped to his knees, kissing his way down my stomach and stopping between my thighs. He pressed a kiss to my mound, then I felt his tongue lapping at my folds.

"Oh, God," I gripped his hair as he pushed his tongue inside me. I felt a finger enter me as he continued his assault, and my knees went weak when he sucked at my sensitive bud. He pumped a finger in and out as he licked and kissed my most sensitive core. When I thought my legs might buckle, he stood and scooped me up.

His bed was large and luxurious. He laid me down, then flipped me over.

"On your knees."

I obeyed, turning on my hands and knees, my heels hanging off the edge of the bed.

"Mmm," he ran a hand over my ass, squeezing and kneading, as I heard his pants unzip. I felt him rub his length up and down my opening, the smooth head of his cock teasing my outer lips which were now nearly dripping with wetness.

"God you look so sexy."

He pushed his cock into me just barely, then stopped. I squirmed again as he reached around and tugged at my nipples. I tried to push back into him, but he held my hips with one hand and swatted my ass with the other.

"Ah-ah," he teased.

"Oh," I gasped, as he spanked me again. Then again. I felt his cock push in just a bit more, his thick girth filling me and nearly trembled.

"You like the way I feel inside you?"

"Mm," I grunted.

"That's not an answer." He spanked me again, harder this time. I felt my skin growing hot.

"Ah! Yes!"

"Good girl." He pumped inside me, once, twice. Pulling out slowly, then firmly thrusting back in. He spanked me again, fucking me roughly until I came.

"Oh, God!" I screamed, my whole body tensing as he continued to pump into me, filling me tightly, his thrusts swift and unrelenting.

"On your knees."

Weakly, I slid to the ground. He gripped the back of my head and guided his cock into my mouth. I sucked generously, feeling his thickness and swirling my tongue around the tip.

"Suck hard."

I obeyed, feeling him pulse and grow stiff. He began to pump gently into my mouth, gripping my hair, I took him deeply until, with a final thrust and a loud groan, he came and I felt his warm cum slide down my throat.

With a final lick, he pulled me to my feet.

"I'm going to fuck you again."

He pushed me back onto the bed, onto my back, and suckled my breasts again, teasing the nipples until they felt tender and erect, squeezing with his hands.

He found my mouth again and began to kiss me deeply, urgently, and I felt his cock stir again.

Unexpectedly, he stood, opening his bedside drawer and pulling out three silk ties.

"Lift your arms."

I watched as he tied both my wrists to the bedpost, then slid one over my eyes.

"Are you uncomfortable?"

"No," I breathed as his tongue dipped into my bellybutton. His teeth scraped along my abdomen.

"Good."

Blindly, I heard him fumble around the drawer again. Curious, somewhat hesitant, I listened to try to figure out what he was doing.

"This won't hurt."

I felt something cold press into me. He was fucking me with some kind of object as he kissed me again. I moaned.

"Spread your legs."

Somewhat hesitantly, I obeyed, and I felt it press against my asshole. He worked it into me slowly, filling my ass. I felt oddly turned on, helpless to move my arms. I arched my back as he pushed it deeper, finger fucking me as he went.

"Wider."

I lifted my knees further apart and the end of the plug finally met my ass. Then, I felt him tease me again, his cock pressing at my opening.

"Ah."

I strained against the fabric of the ties as he barely pressed inside me, slowly filling me, I felt his cock twitch as he bottomed out inside me. His hands gripped my hips tightly as he worked his way in and out, slowly picking up the pace.

"Tell me to fuck you."

"Oh God," I groaned, as he slowly pulled out. Then stopped.

"Oh, please. Fuck me. Fuck me!"

He rammed inside me. I heard the slap of skin as he began a brutal pace, my ass bouncing as he grunted with each thrust, feeling impossibly full and overwhelmed with sensation.

"Oh, fuck. Oh fuck."

He lifted my hips off the bed, fucking me impossibly deeper, until I came with a scream, shuddering as he came with me, filling me with his load.

Exhausted, spent, I felt myself go limp as he lay on top of me, both of us sweaty and sated.

"Tired?" he asked me finally. I nodded.

"Too bad..." I heard the humor in his voice. "The night's only half over."

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousabout 5 years ago
looking forward

To the next chapter please!

Share this Story

story TAGS

READ MORE OF THIS SERIES

Similar Stories

My Side Slut, April Pt. 01 Man hires April who becomes his side slut.in Erotic Couplings
Chelsea is Forced Pt. 01 Chelsea is forced to give a blowjob. Or is she?in NonConsent/Reluctance
Blackmailed at the Conference Pt. 01 The seduction and capture of Jessica.in NonConsent/Reluctance
Madison's Changing Life Pt. 01 Madison is caught.in NonConsent/Reluctance
The Business of Samantha Ch. 01 The correction of Miss Barrington.in NonConsent/Reluctance
More Stories