Josh's Dilemma

byNaked1©

At 8 p.m., the multi-level building where Josh spent well over a third of his waking life, earning his bread as an advertising executive was empty.

Everyone else had gone home three hours before.

But working overtime to secure accounts was a fact of life for Josh, and he spent at least three nights a week in his office until 10 or 11 o'clock, or even later on occasion.

Josh was driven to succeed.

Leaning back in his plush, leather chair, he stared at the computer screen.

The perks of the job were unbeatable. The money was excellent. He enjoyed executive privileges, and was one of two in consideration for a junior vice-presidency next year. According to the senior grapevine, Josh was in fact, the prime candidate.

He hated the hours at times, but he was well-liked by all of his superiors and peers.

He was confident that he would eventually be chosen for the promotion, based on his impeccable record of driving up the CEO's take-away. He'd also won the recognition of the board of directors several times over.

He was a shoe-in.

Recently though, at different times, when he allowed it...he'd found himself wondering if the end was worth the means.

Outside of his career, he had no life to speak of...he had never married and started a family. He never had the time to pursue it.

In fact, he rarely had time to date outside of the obligatory company related social events and office parties.

Suddenly, a small chuckle escaped him as he realized that he hadn't even had sex since Christmas.

It was now mid-July.

Other than the occasional sexual interlude enabled by office gatherings and booze...Josh relieved himself through regular doses of internet porn and masturbation.

The clock over his desk ticked indifferently as his mind wandered to the Christmas party.

Becca Salson had shown up dressed to kill in a short, tight mini-skirt and top that looked painted over her perky boobs. He'd plied her with more than a few long island's, and ended up fucking her in the darkened lunch room, while everyone else partied on, unaware.

Josh's cock stirred in his slacks at the memory.

Both of them were three sheets in the wind, as Becca had slowly stripped him...dropping every piece of clothing that he wore on the lunch room floor, until he stood naked and hard in front of her.

He'd then taken her savagely, lifting her skirt and pounding her hot body on top of a lunch table, cumming all over her delicious, bare ass...it was the most animalistic experience of his life.

Seeing her naked ass from under her little black skirt, panties around her knees with his mind's eye...his hand wandered to his crotch. Josh slowly teased himself, gently squeezing along the outline of his erection under the material of his slacks.

Glancing at the clock, he saw he had time.

Sitting up, he reached for the computer mouse and chose his favorite website for times like these from among his favorites.

Part of executive privilege (although not intentional most likely) was the ability to use the internet unmonitored. Josh often took advantage of this perk to relieve himself in his office after hours.

As Josh watched, squeezing himself through his pants, a gorgeous, large breasted blonde appeared, wearing a taught dress that stopped just below her crotch, complimented by dark, sheer nylons and black, spiked pumps.

The video was titled "Jack for Janet..."

One of his favorites.

Basically, a CFNM oriented video, "Janet" teased, slowly, encouraging the viewer to strip naked and masturbate for her.

The storyline concluded with mutual masturbation...the viewer totally naked, jerking his cock and cumming all over himself, while Janet teased herself to orgasm inside of her panties, with her legs spread in front of the camera.

Janet never actually removed any clothing...but that wasn't the point of the video.

Being naked in front of hot, large-busted, fully-clothed women had always been one of Josh's favorite fantasies...which is one reason the encounter with Becca had been so exciting for him.

As Janet smiled from the computer screen, Josh unzipped his slacks. Lifting his hips, he pulled them and his underwear to his knees and got down to business.

On screen, Janet lifted her huge tits through her dress, kneading them and rolling them in her hands, while Josh pointed his cock at her, and pulled slowly, stroking upwards...before squeezing it, and sliding back down to the base.

One thing was for sure, Josh may not have gotten much play due to the nature of his job...but he was no slouch. When erect, his cock stood at a full nine inches...he knew because he'd measured it in college.

He could easily wrap both hands around the shaft, and never even touch the head of it.

"Now take off your pants baby..." Janet said from the video, spreading her pantyhose-covered legs.

Standing, Josh kicked off his loafers and allowed his pants and underwear to fall to his knees, before stepping out of them.

Wearing his shirt, tie and socks, he sat down again and put his feet on the desk...stroking his hard dick faster at the woman on the screen.

"Mmmm..." Janet cooed, licking her luscious lips. Jack loved those lips.

"Let's get that shirt off honey..." Janet instructed, while snaking a perfectly manicured hand towards the area between her legs.

Opening his tie, Josh pulled it over his head, leaving it there. Then he unbuttoned his shirt.

Pulling it off as well, he tossed it on the floor...before throwing his tie on top his shirt.

Now naked, save for his socks, Josh leaned back, feeling the chair's leather under his bare skin.

Being naked in his office felt so dirty.

While he regularly masturbated in his office, he knew that the building was long empty. There was no real danger of being caught; still, the idea of what he was doing, where he worked, was very exciting.

At times when he stripped and jerked off at work, he even walked out into the darkened hall outside of his office and stood, pretending that it was the middle of the day and everyone was at work...as he emptied his load all over the carpet.

One of his favorite fantasies was getting caught, naked, masturbating in his office, by one of the pretty secretaries that worked just down the hall.

He would pretend that it was daytime again, and one of them would walk in through his open door and catch him...standing there gape-mouthed as he pumped his cock fast and hard, groaning, and cumming in front of her.

"Are you naked, naught boy?" Janet asked from on screen, smiling wickedly into the camera. Quickly, Josh removed his socks and left them on the desk.

"Yeah..." he breathed, stroking his cock at the blonde. "I'm totally naked for you..."

Josh's hand flew on his cock as Janet diddled herself inside of her panties.

"You dirty boy..." Janet said, pushing her fingers deep into her wet cunt on the screen, "look at you, all naked in front of me..."

"Oh god...yeah...I'm totally naked for you Janet," Josh said, squeezing his balls, stretching the skin outwards and rolling it between his fingers.

He watched the woman on the computer screen over his throbbing rod...imagining that she was right there in the office with him...he was so close to cumming.

"Yeah, jerk it..." Janet whispered lewdly. "Jerk off for me baby....oh yeah...stroke your big, hard cock..."

Josh whimpered, pulling on his throbbing meat hard, twisting it, and pushing it to the side.

He spit into his palm for lubrication.

Grabbing at it again, he stroked hard and fast, while tugging at his balls.

Reaching into the left desk drawer, he retrieved a wooden clothes pin, and slowly, gently, clamped it to one nipple...moaning as it bit into his tender flesh.

"OH...JEEZUS FUCK..." he said loudly, stroking as fast he could...stopping, squeezing, stroking, and repeating the pattern.

"Good, boy...good naked boy..." Janet moaned from the screen, while jamming her hand into her wet, pantied cunt between her spread legs.

Next was Josh's favorite part.

On screen, Janet leaned back and placed her feet wide apart with a good camera shot of her fingers moving inside of her slick pussy as she pulled the crotch of her panties aside.

"Cum for me..." she told her masturbating male audiences,as the camera pulled back, showing her her huge, bared cleavage, "cum all over yourself for Janet, honey, please...cuuumm...mmm..."

Leaning back in his chair, Josh placed his bare feet out in front of him on the desk...one on either side of the computer monitor, and pounded himself as hard as he could.

Suddenly, his stomach muscles wrenched as his orgasm began.

Groaning loudly, he fisted his cock, pumping out great, long, white strings of cum...shooting them high into the air, and covering his belly and chest with his juices.

"OH GOD...JANET...FUCK...I'M CUMMING FOR YOU!" He yelled, loud enough to be heard down the hall...had there been anyone around to hear him, as he pounded himself into ecstasy.

Finally, spent, he slacked in his chair, watching his cum-splattered chest rise and fall. On the screen, the video had ended with Janet's mouth frozen in a perpetual state of orgasm.

Glancing at the clock, Josh muttered. He'd better clean up and get back to work if he was going to make it home before midnight.

At 4:30 the following afternoon, Josh was knee-deep in spreadsheets when the email icon flashed in the bottom corner.

He frowned.

He'd worked through lunch to get ahead and was actually looking forward to leaving at 5 o'clock.

Resigned, he clicked the icon.

It was a message from Dana, one of the heads in PR, two offices down the hall from Josh. Dana and Josh often collaborated. An email from her was not unusual.

But what was unusual was when Josh opened the attachment titled, "Hi honey."

The attachment was a video file.

As it opened, Josh's jaw hit his chest and his heart stopped.

In the video, Josh saw himself, from the computer monitor's point of view...naked in his chair...stroking his cock and moaning.

As he stared in disbelief, the video-Josh yelled, "OH GOD...JANET...FUCK...I'M CUMMING FOR YOU!" With that, Josh watched in horror as he splattered cum all over himself...convulsing and jerking in orgasm in his office chair.

Then, the video ended and went dark.

The email read simply, "Hi Josh, can you come to my office after work? Dana." The email closed with a smiley face.

Josh was floored, stunned, and completely speechless and thoughtless.

He sat in a state of shock, trying to make sense of what he had just witnessed.

At 4:50, he'd finally recovered enough to wonder how Dana had managed to record him. Searching his desk, he found nothing.

"What the fuck?" he said aloud, perplexed, tearing through papers and drawers looking for any signs of recording equipment.

He found nothing.

Finally, coming to his senses, he realized it was shortly after 5, and time to head to Dana's office.

He wondered if he should go.

What was she planning?

He'd known Dana for a couple of years now, and she'd never given any kind of indication that she didn't like him or had it out for him.

Maybe it was a joke on her part?

Has someone else sent her the video somehow?

Perhaps he should just leave.

He could go, and not come back...just give up his job and never come back again.

He could find work somewhere else.

That was ludicrous and he knew it.

He had to go to Dana's office. He had no choice.

With a sick feeling in his gut, Josh left his office at 5:25 for the short walk to Dana's office.

"Josh!" Dana smiled warmly at him from behind her desk as he entered.

"Uhm, hi Dana," he fumbled, nervous.

"Have a seat," she said warmly again, still smiling.

Josh sat.

"I wasn't sure if you were going to make it," Dana joked, laughing, causing her jet-black hair to fall slightly across her forehead.

In spite of himself, Josh couldn't help noticing how beautiful she was.

Dana always dressed to kill, at least for an office setting. Her deep blue eyes pierced him through as she sat, waiting.

"I uh..." Josh started, before his voice caught in his throat.

Dana smiled at his predicament.

"You're hot," she said flatly.

Josh shifted.

What the hell was she doing?

"Look Josh," Dana said, smiling again. "I'll cut to the chase."

Turning in her chair, she faced him full-on.

Josh couldn't help notice how the powder-blue blouse she wore stretched tightly across her full breasts. The top few buttons were undone, revealing a goodly line of cleavage.

"Eyes up here Joshie.." Dana giggled.

He'd been caught...again, it seemed.

"Josh," Dana opened, growing more serious, "I know what you do...I know that you take your clothes off and jerk off in your office at night."

Josh's face went red.

He swallowed hard.

His heart jumped.

"I've seen you walking around naked and hard, beating your big hard cock. I know that you sometimes go out in the hallway..."

Josh was silent.

He dropped his eyes in shock and shame, but not before noticing that Dana's nipples were poking through the material of her blouse.

She wasn't wearing a bra.

His cock stirred slightly.

Was he some kind of weirdo? How the hell could anyone think of Dana's tits at a time like this?

He pushed it from his mind.

"How?" Josh said aloud, more wondering than actually asking.

"How?" Dana repeated. "How did I catch you?"

Josh nodded dumbly.

"That's easy" she waved a hand.

"Josh, you're an awesome account manager...the best." She said, smiling yet again.

Leaning forward, as if she was going to let him in on a secret, she giggled low, making her breasts jiggle.

"But you are lousy at technology hun," she finished, self-satisfied.

"I simply tapped into your webcam...see?" Turning to her monitor, she spun it towards him.

"See all these files?" she asked, pointing at the screen. "They're all you hun."

Josh stared in dumb shock.

There had to be at least fifty different video files.

"A few months ago, I spent about a week working late myself. I heard you down the hall, jerking off, grunting and groaning, so I tapped into your webcam."

"It runs every night...just in case."

Josh was stunned again.

"I started collecting your videos, looking forward to this day," she finished again, self-satisfied again.

"But how come I didn't see the camera light?" Josh asked, in genuine wonder.

"I disabled it babe," she grinned. "I told you that you are technologically retarded Josh."

"How come I never saw you in your office?" Josh asked, incredulous.

"Seriously Josh?" Dana laughed. "It's called a remote location and a laptop hun..."

It was too much for Josh to process.

"So, what are you going to do?" He asked meekly.

Dana grinned, and shifted in her chair. Her blouse opened slightly, revealing more cleavage. Unable to help himself, Josh looked.

"It isn't about what I'm going to do Josh," she answered him matter-of-factly. "It's about what you're going to do."

Josh was a silent a moment, mulling. What did she mean?

"What am I going to do?" he said, finally.

Dana leaned back in her chair and smiled, crossing her nylon-covered legs.

Josh saw that she was wearing a pair of black, spiked heels. Her incredibly short, black skirt rode up slightly, exposing a snatch of creamy, bare thigh, over the top of her stocking.

His cock did more than twitch at that, starting to rise in his slacks.

"Whatever I tell you to silly," Dana laughed. "You're going to do whatever and whenever I say."

"Dana, that's blackmail," Josh stated in an attempt at defense.

"So?" Dana said. "Who are you going to tell? What are you going to say? Dana filmed me beating off naked in my office?"

She had a point.

"Listen Josh," she said, leaning forward.

Fiddling with the buttons at the top of her blouse, she opened another one, exposing a bit more of her delicious cleavage.

"Here's the deal. You do as I say, or, I will post all of these videos on the company website, all over the internet, and email them to the CEO."

Josh swallowed hard.

She had him and she knew it. What was he supposed to do?

He sat sweating bullets and trembling.

Seeing his dilemma, Dana softened.

"Look honey," she said, soothingly, "I'm not totally evil. I've also seen what kind of porn you watch...I know what turns you on. You like to be naked where you shouldn't, and you love being naked in front of women, right?"

Josh nodded, admitting it silently. He was busted anyway.

"So," she continued sweetly, "I promise that as long as you do as you're told...to the letter, you'll have fun. And, Josh, I will never tell..."

Josh weighed the situation.

He could overpower her...but that probably would lead to trouble.

He could refuse and live with the consequences...but he'd be ruined.

Then, he had an idea.

"If you send those out, Dana," he began, unsteadily, then gaining momentum, "everyone will know you posted them, and you'll be fired."

"Really Josh?" She mocked in a sweet-sounding voice. "You think I'm that dumb? That kinda hurts..." she laughed. "Rest assured dear, if anything happens to me babe, they will be posted by someone else."

"What?" Josh was shocked. "Someone else knows?"

"Let's just say I have a plan," Dana laughed. "But if you do your part, you'll never meet her."

She could be bluffing Josh thought...but he had no proof. He couldn't risk it.

"What do you want me to do then?" Josh asked, resigned to his fate for the moment.

"Do you agree?" Dana pressed.

"Yes, I guess I do..." Josh finished, dropping his head.

"Awesome!" Dana clapped her hands together like a little girl. "You can start by taking off all of your clothes right now."

Josh stayed where he was.

"Josh," Dana said coyly, smiling at him, "do you know how many times I've watched you stroke that big, cock of yours with my fingers in my pussy?"

Josh jumped a little. Maybe there was hope after all.

"I've gotten myself off to every one of these videos...god, I love seeing you strip naked and play with yourself..." Her eyes were suddenly far away...watching something only she could see.

"But don't think this will be a touchy situation," she said, coming back. "At least not for you...I mean, you might be touching yourself," Dana giggled at that, "but you won't be touching me...understood?"

"C'mon now honey," she pressed, "I wanna see that big, fat cock in person."

With seeming no other choice, Josh rose slowly.

Dana smiled at his acquiesce, motioning for him to come around the desk.

Josh ambled over slowly, stopping a couple feet in front of her.

"Now," Dana said, spreading her legs slightly at him. "Strip. Take it all off, every last stitch."

"But Dana," Josh protested weakly, sounding like a punished boy, "the door's open."

"Pfft..." she blew her tongue between her lips. "There's nobody here. Beside, you like getting naked at work don't you? Remember, I have proof of that."

Josh winced.

"C'mon baby," Dana said soothingly, in a low voice, turning her face upwards to look at him from under her bangs. "We don't have to go...there...do we?"

She really was a hot woman.

Her deep, blue eyes were gorgeous, and beckoned him to do her will.

Her breasts were exciting...rising and falling under her blouse...much of her cleavage was bared...Josh allowed his eyes to roam over her, taking in her shapely curves, and delicious, bare thighs...

In the outfit she was wearing, she really looked like some kind of fantasy office slut in high heels.

His cock swelled and rose in his pants in spite of himself.

In a strange way, the thought of what he was about to do turned him on...he was actually going to take his clothes off in front of Dana...right here in her office.

Report Story

byNaked1© 7 comments/ 58052 views/ 22 favorites

Share the love

Report a Bug

Next
2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel