Working Late with the Boss

Jill clicked her nails irritably on her keyboard as she sat at her desk and stared out the window from the 42nd floor office suite. The crush of rush hour had ended over an hour ago, and yet the streets and sidewalks were teaming with people. Jill slumped back in her chair. It was already 9:00 pm and all the other executives had gone home for the night, but Jill's boss insisted on working late again, which meant she was working late.

She was an attractive woman in her mid 30s with shoulder-length black hair and warm brown eyes that were usually hidden behind a set of thin-rimmed glasses. She kept active, regularly visiting the gym during the week and during the warmer months, she jogged through Central Park on the weekends. Most of her friends were married and had started families. Jill wanted to settle down too one day, but for now, she was happy with her life and focused on her career. She'd been out of college for over ten years, eight of which she'd worked for Cerberus Corporation as an administrative assistant until recently, when she was promoted to officer manager for the new Assistant VP of Communications.

Nearly two months had passed since Jill had taken the position and yet, most of what she'd learned about her new boss had been through rumors and water cooler gossip. Steven Cline Jr. was cocky young hire, fresh out of Harvard with his MBA. He was smart, handsome, and in Jill's opinion, a bit too confident for a 25 year-old. In public all the other junior executives agreed that he was the best man for the job, but privately most attributed his success to his father, Steven Cline Sr., and the current CFO of the company.

Others could say what they wanted about him, but Steven Cline Jr. was a go-getter just like his old man. In all her time at the company, Jill had never seen such a strong work ethic. He worked late every night, often by himself, though on occasion he asked her to stay late with him to help wrap up a project. Tonight was one of those nights.

Jill turned and watched as the door opened and Steve came out of his office with a stack of papers in hand. Jill studied him as he approached. His hair was cut short and his handsome young face was set with a strong, angular jaw and a dimpled chin. Steve dressed well, his hand-made $2,000 suits managed to accentuate his impressive physique gave him the look of a high-end fashion model. He was the most attractive man she'd ever met in her life.

As Steve took the last few steps to her desk, Jill's eyes were drawn to the bulge in his pants. A took a moment for her to realize that she was staring and her eyes darted away, but it was clear that Steve was carrying something around in his pants fatter than his wallet.

"Already done, I'll get stared on these right away Mr. Cline." Jill said, slipping her glasses back on.

"That's great." Steve grinned. "You know, when we're working alone like this, you don't have to be so formal. You can call me Steve."

Jill looked back at him and shrugged with a grin. "Ok, thanks."

Steve smiled in return as ill began pouring over the reports. "You know we'll be done soon. If you're not doing anything, perhaps we can go out and get drinks, maybe even grab a late dinner and get to know each other better."

Jill turned and stared at Steve's hand, which had settled on her arm and was gently squeezing her shoulder. "I'd like that Mr. Cline, but-"

"Steve." He interjected.

"Right, Steve." Jill cleared her throat. "That sounds nice, but I have plans tonight. Can I take a raincheck?"

"You have plans tonight, after 9:00pm?" Steve shot her an inquisitive look as he leaned against her desk and folded his arms across his chest. "What, are you going out on a date?"

Jill shook her head. "That's a bit personal, don't you think, Steve?"

"Maybe," Steve smirked and nodded at the use of his name. "So who's the lucky guy? Anyone I'd know from the office?"

Jill grit her teeth into a smile. "Of course not, that would be against company policy."

"Oh, that's right, I forgot about that." Steve's smile broadened. "So that must be why you keep shooting me down every time I ask you out to dinner."

Jill huffed and pushed back her keyboard. "No, sir."

"Or is it because I'm your boss?" Steve grinned. He seemed to enjoy reminding her of that whenever he got the chance.

"Well, yes. That's part of it I suppose." Jill replied.

Steve tapped his finger against the dimple in his chin. "Hmm. So if I wasn't your boss, you'd consider it?"

Jill could see that he wasn't going to let this out of his teeth. "Yes, I'd probably consider it then."

"Is that so? I guess if I want to have a shot, I'll have to fire you." Steve joked and edged a bit closer. "Unless of course, you can pretend for a minute that I'm not your boss."

"I suppose I could try that." Jill replied quietly. The longer they played this game, the longer it would take her to finish. She just wanted to go home.

"Good." Steve whispered, staring intently in Jill's eyes. They were only inches apart, Jill could smell his cologne and feel his hot breath against her face. Then suddenly he made his moved, closing the distance quickly. Before Jill knew what was happening, they were locked in a passionate kiss. At first she tried to resist. Everything about this was wrong, but the longer they kissed, the more Jill wanted it, until all reason and logic was swept away in the heat of the moment.

"This is so wrong." Jill whispered as Steve's hands delved into her cardigan and began to fondle her breasts.

"Shhh." Steve kissed her again, exploring her mouth with his tongue as his hands continued to explore his body. Jill liked the way his lips tasted on hers, and soon, she was fondling him as well, grasping at his biceps and broad, muscular chest. As their bodies pressed closer, Jill felt the rigid outline of his cock rub against her through his slacks and she nearly gasped. It was huge. Jill reached down and grabbed Steve's crotch and massaged his hard-on through his pants.

Oh, yeah." Steve murmured as he reached inside her shirt and fondled Jill's large breasts. They were so warm and soft in his hands, his cock shuddered as he imagined what they'd feel like to fuck her tits. Reaching for her nipples, Steve pinched them between his fingers, causing Jill to gasp.

Things were moving too quickly for Jill and she knew she needed to stop before things got out of hand. She tried to push Steve back, but he held on tight, still kissing her neck and trying to pull off her cardigan. Steve ignored her pleas and continued to ravish her until finally Jill let out scream.

A startled Steven was pushed back against the desk, both of them were panting from the excitement

"This isn't right." Jill said shaking her head.

"Why not?" Steve asked, still panting. "I want you, you clearly want me. This doesn't have to be any more complicated than that." Steve's cocky grin had returned.

Jill studied his face. She could see that he was used to getting his way with women, .

"Come on let's not ruing the moment," he pressed. "You've got this whole Mrs. Robinson thing going on."

"Mrs. Robinson? Just how old do you think I am?" Jill replied, unable to mask the anger in her voice.

Steve rolled his eyes. "I'm not saying your old, just that you're - older. It's not a bad thing, in fact, I'm sure you could teach me a few things."

Jill's face was still flushed, but slowly she managed to curl her lips into a smile and slid her hand up her young boss' thigh. "I have worked for the company a long time," she admitted "I suppose there are any number of things I could teach you."

There was an edge to her voice that made Steve grin. "I bet you could."

As she spoke, Jill's fingers worked the clasp of Steve's black Italian leather belt and unzipped his pants. "Tricks of the trade to help you become a better exec." Slowly, she slid down his suit pants, revealing Steve's underwear, a designer pair of black boxer briefs.

Steve's eyes were locked on hers, filled with desire. He tried to reach out and grab her, but Jill recoiled and shook her head.

"Success only comes to those who are willing to take risks. If you're going to make it in this business, you've got to have balls." Jill said with a smirk.

Steve shot her a knowing smile. "Is that right?"

"Oh yes, very, big balls." Jill cooed as she playfully gave his package a squeeze.

Steve's smile widened. "I think I have that covered," he replied confidently with a wink, "but I'll let you be the judge."

Jill smiled back at him and hooked her finger on his the waist band of his underwear and pealed his boxers off with one yank. What she saw caused her to stop in her tracks and clear her throat.

As if being being born into money wasn't enough, Steve had been given the perfect package. He had a beautiful nine inch long cock, capped off with a thick, pink head and a heavy pair of juicy, egg shaped balls, that swung pendulously between his legs. Even his scrotum was smooth and shiny, free of blemishes. For a moment, Jill remained still, staring in awe.

Steve sat back and watched with pride as Jill's eyes feasted on his manhood. "What do you think, do I have the balls to become a captain of industry?"

Jill remained speechless as she reached out and touched his throbbing erection. Steve shuddered as she lifted his shaft out of the way and wrapped her fingers around the soft, pink orbs. They felt like putty in her hand.

"You were right, you have quite a set here." Jill cocked her head to the side and gave Steve's bull balls a firm, gentle squeeze.

"I'm glad you agree." Steve said, still smiling confidently.

Jill continued to roll Steve's large gonads between her fingers for a few moment longer. "But there's one other thing more that you'll need to become successful."

"What's that?" Steve asked looking bemused.

"Respect." Jill replied flatly.

"Respect?" Steve repeated.

Jill nodded, slowly increasing the pressure on Steve's testicles. "Respect can make or break you in this business, for your clients, your investors, even your employees. You're position exists because of them, so they all deserve your respect."

Jill no longer bothered to hide the irritation from her voice. She had a tight grip on Steve's baby-makers, so tight in fact, that Steve began gasping for air as his mild-mannered secretary worked over his nuts.

Steve's face became flush and his jaw tightened as his heavy testicles were kneaded like they were two lumps of dough. He was used to women playing with them during foreplay or even squeezed while having sex, but he'd never had his balls manhandled by an angry woman. Already his nuts had begun to ache and the muscles in his abdomen clenched up as Jill continued to grind his precious jewels between her fingers.

"Alright!" Steve squeaked. Both Jill and Steve were both surprised by the high-pitched tone in his voice. "I get the point, ok? Could you ease up a little?"

Jill shot him a dirty look and squeezed his sac even harder, forcing his nuts down to the base of his scrotum and proceeded to smack his twin orbs with her hand the way a mother would swaddle an unruly toddler's behind.

"Unghhhh!" Steve groaned and his entire body bucked as his large, juicy gonads were flattened against the palm of Jill's hand.

Jill continued to smack Steve's nuts a dozen more times until they were good and sore. Steve whimpered with each impact, his fingers turning white as he clutched the edge of her desk. A single tear slid down the side of his cheek.

Jill paused a moment and listened to the sound of Steve's breathing. He was panting hard and staring back at her wide-eyed. He looked frightened.

"As long as we work together, don't you ever disrespect me again. I'm not some eye candy for you to drool over, I expect to be treated like a professional." Jill said in a stern voice. She knew it was completely inappropriate for a subordinate to speak to her boss in this way, but the tables were turned and she had Steve by the nuts, so she got to make the rules.

Steve nodded wordlessly, still staring back into Jill's eyes like a deer caught in the headlights.

The entire situation made her smile.

Changing tact, Jill loosened her grip and began to soothe Steve's traumatized testicles, rubbing them gently between her fingers. Steve seemed surprise by the welcome change, and let out a long, soft moan as the pain in his nuts was slowly ebbed away and replaced by pleasure. Almost as quickly, his dick began to respond to the improved treatment in a matter of minutes, his cock was jutting up into the air at full mast once again.

Jill wrapped her hand around Steve's shaft and slowly began to jerk him off.

"I like you, Steve." Jill said suddenly between strokes.

Steve cleared his throat, taken off guard by the sudden admission. "I like you too." He said sheepishly as Jill continued to pump his long cock. Seemingly appeased by his answer, she increased the speed of her hands, causing Steve to moan with pleasure.

"I am very good at my job, you know. Going the extra mile isn't a problem for me, I can be very discrete." Jill made it a point of fact.

"Oh, yeah." Steve moaned as Jill's wrists twisted and turned as she stroked his dick.

"I have a feeling we're going to get along just fine." Jill smiled.

"Yeah, me too." Steve whispered as he watched her hand pump up and down.

Jill remained silent for a few minutes and she let the tension build as she stroked Steve's massive meat-stick. She watched his chest heave and his breaths become light and shallow. His entire body seemed to begin to tense up.

"You know, I think I'll be up for a raise soon." She said with her eyes still fixed on her busy hands.

"Oh, Yeah?" Steve replied half heartily. His eyes were fixed on her hands too.

"Yeah." Jill slowed her strokes to a crawl until she was sure she had his attention. "I thought we could - negotiate."

Steve's whole body shuddered from the stalled orgasm, but his eyes were held fast in Jill's gaze. She had him and she knew it.

Steve exhaled slowly as Jill continued to tease his cock. "I'll give you anything you want," he blurted out, "just don't stop."

Jill smile brimmed with confidence. "I was thinking ten percent."

He cleared his throat. "Ten? I don't think I can get without authorization."

Jill made a playful pouting face. "Don't I deserve it?"

Despite her playful tone, Steve felt the weight of Jill's stare as she scrutinized his reaction.

"Of course . . . I just . . . I'm not sure if I can make that happen." Steve stammered honestly. "But I'll try." He quickly added.

Apparently satisfied with his answer, Jill went back to stroking his dick with a series of long, hard pulls that sent shivers down Steve's spine. In seconds, he felt the climax build up inside him, threatening to explode.

"I'm gonna cum." Steve whispered, his cock twitching uncontrollably.

The need to cum was so intense, he felt like he was going to burst. Suddenly Jill let go just as the first flood of white cream spilled out of Steve's dick like a fountain.

Steve threw his head back and let out a throaty moan as thick ropes of cum began gushing out, coating his stomach with the thick, rich batter. Steve's balls churned and tightened in their sac as jet after jet of his stick juicy was pumped up and out of his fat cock.

Jill watched with suspended amazement as Steve continued to shoot his big load all over himself. Even now, his dick was still dripping more of his juicy spunk.

Steve grabbed his cock and gave it a few short strokes. After squeezing out the last few drops, he sighed and tilted his head back, allowing the aftereffects of the orgasm to wash over him.

Apparently forgotten, Jill suddenly sunk her knee into Steve's groin, smashing both of Steve's balls.

Steve howled in pain, his orgasm ruined, he tried to cup his genitals but Jill kept her knee planted and his nuts pinned against between her leg and the mahogany desk.

"Perhaps you've forgotten how this works?" Jill twisted her knee, sending Steve into new levels of pain. "I thought we'd come to an understanding - I thought, you respected me."

"I do, I DO!" Steve squeaked. "Please!"

"Then you should be prepared to pay me fairly." Jill scowled.

Steve's balls were killing him. He felt like he was going to wretch.

"Alright, you'll get your raise. Ten percent, I promise!" Steve's voice was a hoarse whisper.

"Fifteen." Jill replied flately.

"Fifteen? Ten was going to be difficult enough, I can't give you a fifteen percent raise!" Steve croaked. He was almost on the verge of tears.

"You can't, or won't?" Jill asked. Her full weight was now pressing on his bloated gonads and they felt like they were going to burst.

"Can't, can't!" Steve squeaked. "The board would need to authorize it."

Jill stared at Steve for a moment, deciding wether she should believe him. "Fine, then ask daddy to take care of it. They'll sign off to anything if the CFO gives his endorsement."

"Ok, ok, fine, I'll talk to him, just please, stop hurting my nuts." Steve pleaded. He was gasping for air. He looked weak and like he was about to faint.

Jill grinned and lifted her knee off the desk.

Steve cupped his battered balls with both hands and slouched against the desk, sobbing in pain.

Jill adjusted her squirt as she stood up and gathered her things.

"I'll be going home now Mr. Cline." She said, already slipping back to her more formal demeanor. "I won't be coming in tomorrow, so you'll have to finish processing these reports yourself. Good night."

Steve's eyes were closed, still in too much pain to speak. Jill gave him a kurt smile, then spun on her heels and walked out of the office, leaving the speechless young executive, half naked and sprawled out on her desk, behind.

- Our young Mr. Cline was inspired by the model, Steven Kuchinsky -