Josh's Dilemma: Mr. Cleary

"Oh...god...Dana...Dana..." Mr. Cleary breathed hard, stroking and pulling at his smallish penis hard and fast.

The mirror reflected Mr. Cleary's pudgy form, standing completely nude by the sink counter where Dana had set her purse. His clothes were piled in a heap by his feet on the tiled floor of the women's restroom as he furiously stroked himself in front of her.

His clothes were a heap by his feet.

"Wanna see my tits Mr. Cleary?" Dana teased him, slowly flicking the buttons of her pink blouse open with the fingers of one hand...torturing him.

Her other hand snaked just below the hemline of her short skirt.

"Oh god yes...please...show me them..." Mr. Cleary moaned. His entire naked body was flushed red with excitement as he beat himself.

"You know, sir," Dana began, twirling a finger through her dark tresses, "any of the women here could walk right in at any time...and see you...totally naked...jerking off for me..."

Mr. Clearly moaned loudly.

"Wouldn't that be so hot?"

Mr. Clearly pulled hard on his pencil-thin dick, drinking in the beautiful, fully-clothed woman in front of him...with her blouse partially unbuttoned to just under her big, soft breasts...he could see the insides of them and it made him shiver with excitement.

Dressed the way she was, she looked like one of the models in the dirty magazines he kept stashed in the bottom drawer of his filing cabinet. She was so pretty, so hot...he couldn't help himself...she...made him...want to jerk off.

Suddenly, Dana spread her legs wider and pulled up the front of her skirt, showing him her pink panties.

Her delicious legs were bared all the way to her thighs.

Mr. Cleary could hardly breathe.

He couldn't think.

Looking down at herself, Dana smiled.

"Uh oh, Mr. Cleary," she giggled like a schoolgirl, teasing him, "you can almost see all of my tits..."

Bending forward in his direction her open blouse fell away from her, exposing her bare breasts, all but the nipples to him, as they hung in front of her.

Outside of the women's restroom, the ten o'clock office was alive, buzzing with the business of the day.

Inside of the restroom, Dana thrust her hips lewdly at Mr. Cleary, making him moan.

Bending over, she showed him her pink, pantied ass cheeks underneath her skirt as she gathered his clothes from the floor.

"I've got your clothes Mr. Cleary..." she giggled.

"Oh...Oh...Dana..." was all he could moan.

With a wicked smile, she stuffed them into the trash can on the wall.

"Now you're really naked..." she cooed sexily. Leaning against the wall, she spread her legs and lifted her skirt above her waist.

Mr. Cleary's eyes nearly bulged from their sockets as his hand flew over his cock.

"Wanna see my pussy?" Dana whispered in a hard tease.

"Yeah, oh god yeah..." Mr. Clearly breathed, beside himself with lust.

"Say please you dirty little man," she hissed hotly. "Say please Dana, I want to see your pussy..."

Mr. Cleary trembled, and stammered. "Please..." he breathed, struggling. "Please...Dana..I...I want to...oh god...I want...I...need...to see your...pussy..."

With that, Dana pulled her panties down...slowly...exposing just the top edge of her trimmed landing strip to him.

Suddenly, a low growl escaped Mr. Cleary's throat...his hand blurred on his cock...he moaned far more loudly than he should have in the women's restroom....and came...shooting thin cum ropes from his little penis at Dana's feet.

"OH GOD...GOD...DANA...." he said, jerking hard and fast, pumping out his cum in front of her.

"Oh yeah...Mr. Cleary," Dana teased, releasing the waistband of her panties as they snapped back up over her pussy again.

"Cummmmm...." She hissed.

And he did.

His fleshy naked body, softened from years of inactivity jerked and jumped...as his knees buckled.

Falling forward, he crashed to his knees...kneeling on the hard floor in front of Dana, pumping the rest of his orgasm onto the floor.

Finally, when he was done...he struggled to regain his breath. His belly hung slightly over his waist as his cock receded under it.

Smiling, Dana snatched her purse from the sink counter.

"Have a great morning Mr. Cleary," she said sweetly, pushing the door open...and then she was gone.

Passing Marcy, the pretty blond from the secretary pool in the hall, Dana smiled.

Josh sat his desk facing the open door, naked from the waist down, as he had done every day at Dana's instruction since his naked exposure on the sidewalk.

His bare feet rested on the soft carpeting under him.

Thus far, he'd had no unexpected run-ins with anyone in the office, save for one of the secretaries who had stood in front of his desk, with him bottomless behind it, offering him a message she'd taken earlier in the day.

Unable to stand, he'd sat glued to his chair as she handed him the message.

She'd been very pretty and his cock throbbed and pulled at him under his desk in spite of his terror at being caught, as he watched her dark curls fall against her beautiful ebony skin.

Remembering the encounter, Josh rested his hand on his naked penis, unconsciously tugging at it. The girl had given him a strange look before handing over the message.

Pausing a moment, her eyes had dropped, scanning the area below his desk.

He was certain that he was well-hidden; still, the moment had excited him, as his cock thickened and swelled not three feet away from her. He wondered if she somehow knew that he wasn't wearing anything under the desk.

Finally, she'd smiled, gracing him again with her soft brown eyes before leaving his office.

Watching her leave, Josh had been suddenly overcome...pushing his chair back and away from his desk, he'd stroked himself hard and fast in front of his open door...listening to the sounds of the busy office...imaging that she was standing in front of him, watching him, as she shot his load on the floor between his bare feet.

"Knock knock," Dana said, standing in the doorway, suddenly breaking his reverie.

Josh waited as she entered.

Coming around the desk, she faced him, smiling.

"Lemme see," she said.

Turning his chair, Josh exposed himself to her. His cock thickened at her, swelling between his bare thighs.

"Mmmm," Dana cooed, "I see you're getting better at this Joshie."

Smiling down at him, she ran her fingers though his hair gently as he reached full erection.

It had been three weeks since Dana had initially confronted him, showing him the video of himself, naked, jerking off in his office. She'd also shown him the collection of videos she'd kept on her hard drive, at least fifty, by Josh's shocked estimation.

She'd blackmailed him to do her will ever since...becoming increasingly demanding...making him go completely naked in public, even out on the sidewalk, and jerk off in front of strangers.

Now, she made him remove his slacks, socks and shoes every morning and sit behind his desk, wearing just his shirt and tie, while she kept the rest of his clothes in her own office.

She also made him leave his door open.

Watching people pass in the hall outside of his office scared him to death...and yet, he found it somehow incredibly exciting...to the point of beating off right at his desk while the busy office whirred around him.

With a possible vice-presidency merely a year away, and with years of hard work to get where he was at...Josh had chosen to do as she demanded instead of risking his future, and quite possibly, his past.

He knew that discovery meant not only no vice-presidency, but he would be blacklisted from ever working as an executive in the industry again.

Now though, he figured that was probably all gone anyway.

He'd been seen walking naked on the sidewalk behind Dana. He'd been seen naked and hard in the lobby. He'd even been seen masturbating in the alleyway.

Suddenly, the memory of Dana's full, soft, breasts in his face made his cock jump and he winced.

On the trip back to the office afterwards, he'd been seen by at least a dozen people or more. Kindly, though, and quite unexpectedly, Dana had him wait in the stairwell outside of their floor as she retrieved his clothes from her office.

He'd been scared to death the whole time, straining to hear any signs of life beyond the door. But returning as quickly as she'd promised, Dana handed him his clothes and smiled patiently as he dressed.

They were late returning for the meeting, but Dana had done an excellent job covering for them, explaining that they'd run into unexpected construction on the road.

Mr. Cleary had accepted the explanation, and Josh made it through the remainder of the day unscathed.

In the ensuing weeks, Josh sweated every moment of every day...expecting the worst. He knew he'd probably been captured by the lobby cameras...but strangely, nothing had, as of yet, come of it.

Although his paranoia had reached epic proportions...he suspected every odd look, every seemingly knowing smile, still, he couldn't believe that nobody had mentioned his exposure.

It was strange.

And yet, it was the subject of each and every one of his furious masturbatory fantasies since...picturing himself naked in the alleyway, fucking Dana's pretty hand as she exposed her gorgeous tits to him.

Not only was the public exposure incredibly exciting for Josh, but secretly, in spite of his shame, or perhaps because of it, the power she exerted over him...when she made him strip naked and masturbate for her...made him throb.

"What you thinking about babe?" Dana chuckled, standing over him.

Josh's cock jumped and pulled at the sight of her.

"Oh, I..uhm..." Josh stammered, embarrassed. It was almost as if she could read his mind and had caught him fantasizing about her.

"Joshie," Dana said sweetly down at him, "I came to tell you that we're going to have lunch with a few of the girls from the secretary pool...I'll come get you."

Josh's heart stopped.

Frozen in time, he stared, wide-eyed in shock at her.

"Dana..." he started, visibly shaken by her statement.

Without another word, Dana smiled wickedly at him before turning to go.

Watching her leave, Josh sat in fear and disbelief.

At the same time, Marcy placed her hand on the women's restroom door and pushed it open, stepping through it.

Mr. Cleary was bent over the sink, completely nude, with his eyes closed, pulling on his penis. "Oh...Dana..." he moaned softly, unaware of Marcy's presence.

"Mr. Clearly?" Marcy blurted, with her hand still holding the door open.

Mr. Clearly jumped, as if he'd been touched by electricity. Spinning, he faced Marcy and tried to cover himself. Frantic, he stammered like a kid caught stealing.

"Muh...Marcy!"

"Oh god, Marcy," he said, panicking. His eyes widened in terror, searching frantically for his clothes.

"What...what are you doing?" Marcy asked, sounding shocked at the sight of him.

"Please..." Mr. Cleary said, trying to regain himself, as if that were possible.

"Please, Marcy...I can explain..."

Despite his utter shock at being caught, Marcy noticed Mr. Cleary's hard little cock poking from between his fingers, as he stood naked and mortified in front of her. Suddenly, he looked less like her boss and more like a pathetic little boy caught jerking off and Marcy laughed...unable to stop herself.

"Why are you naked in the women's restroom Mr. Cleary?" she said finally, taking a serious tone.

"Please don't say anything," Mr. Cleary begged, obviously ashamed and frantic at being caught.

Marcy seized the opportunity.

"I don't know..." she said, "catching you naked, jerking off in the women's restroom is pretty weird..." she allowed her voice to trail off...leaving a menacing silence hanging between them.

"Please...." Mr. Clearly begged again, more urgently. "Please Marcy," he said, near the point of tears, "I'll do anything..."

"Anything?" she said, releasing the door as it closed.

In Josh's office, he sat, staring dumbly at the standard issue office clock hanging from the wall.

It was lunch time.

Since Dana had left, he'd sat, unmoving, terrified, playing out endless possible scenarios in his head.

What had she meant by "a few of the girls?" Did she intend to completely destroy him now?

He could have easily walked away from all of it then and there. He could have...walked half naked down the hall in front of everyone?

That thought stopped him dead.

He'd be finished for sure, if not worse.

Damn Dana.

She'd trapped him in her insane little game and he'd allowed it. He'd been too worried about a future that was likely gone now to tear away from her.

Or, was that the real truth?

Shaking his head, he pushed away the images of her and the things she made him do as his cock thickened at them.

She was exciting, dirty, crazy, dangerous, and so powerful. Her cunning intelligence obviously far outweighed his. Each and every time he's mustered the courage to challenger her, she's been steps ahead of him.

And, truthfully, it turned him on to do the things they'd done. His rising cock confirmed it...yet...while admitting it to himself brought him some strange sense of relief, still...he couldn't shake his fear.

Each and every encounter with her had gotten bolder, crazier...more exciting. He'd managed thus far to escape them unscathed...at least it seemed that way...but where would it end?

His dreams of the vice-presidency, and maybe one day...more, were likely just dreams now that he'd allowed them to slip away...or more appropriately, be taken from him because of his own twisted desires, brought out by Dana.

She'd caught him masturbating naked in his office, and what she was doing was wrong...but in the end, he had himself to blame.

She was a crazy bitch for sure...yet...deep down, she excited him beyond comprehension.

"Ready?" Dana said, as if on cue, from the doorway.

"Ready...?" he repeated dumbly, as if she'd spoken Chinese.

"It's lunch time babe," Dana giggled.

Her short skirt teased just below her crotch. Her shapely, bare legs were delicious. Slightly unbuttoned, her blouse fell open at the top, revealing a cleavage line that disappeared into it, transforming itself into two, heavy, perfectly formed breasts that rose and fell with her breathing. Under the blouse, they were obviously bare.

Josh felt the now familiar mixture of fear and excitement in his belly as his cock thickened, rising, pulsating at the sight of her.

He pushed it away.

It didn't matter anymore.

"Dana," he said, defeated, "it doesn't matter anymore," and dropped his head.

"Doesn't it?" Dana said, smiling, taking a step towards him.

Down the hall, in the women's restroom, Mr. Cleary sat on the edge of the sink in front of the mirror, naked and barefooted with his legs stretched out in front of him.

His hard little cock pointed straight up between his fleshy thighs and barely reached the underside of his belly as he slowly stroked it in front of Marcy.

"Stroke your dick Mr. Cleary," Marcy said not two feet from him.

Marcy was so pretty as he gorged on her long, blonde hair and ice-blue eyes.

His hand moved faster on his cock.

"Slow down Mr. Cleary," Marcy said, pulling her cellphone from the pocket of her slacks.

"Beat that little cock nice and slow...."

Mr. Cleary moaned...slowing his hand. He could hardly breathe as he masturbated, naked in front of Marcy in the women's restroom.

Back in Josh's office, Dana smiled. "Come with me Josh," she said, extending a hand downwards.

Josh sat in his chair unmoving, staring at his desk.

Slowly, Dana pushed a small, thin, black flash drive across it.

"Josh," she said, this flash drive contains all the videos of you that I've taken...jerking off naked in your office...there's over forty of them."

Josh stared, lifeless, at the flash drive.

It just didn't matter anymore.

Kneeling beside him, Dana took his chin gently in her hand and turned his head to face her. Her beautiful blue eyes softened, searching his.

"Josh," she said gently, almost lovingly, "remember when you were naked in the lobby and those women saw you?"

Josh nodded dumbly.

Dana flicked her eyes at the flash drive in front of him.

Suddenly, Josh's own eyes widened in understanding.

Snapping his head around, he stared at her.

"That's right babe," she smiled, "it's all right there, and other places."

"But...how...?" Josh said, his voice dying a slow death.

"Babe," Dana said softly, pressing her hand into his bare thigh...an act that did not go unnoticed by his cock.

"I'm hurt..." she mocked softly. "Don't you think that if I can tap into your webcam, I can't do the same with the security cameras? Please babe, that's insulting."

Josh stared in shocked silence as a shiver of fear crept slowly up his spine.

"Now," she stated flatly, massaging his inner thigh, inches from his steadily growing cock, "you have two choices."

Josh winced as she increased the pressure, digging her nails lightly, but not too painfully into his inner thigh. His cock stiffened, growing fully erect.

"You can do as I ask, and I promise, it will all work out in the end, or...you can choose to walk away, and all of the videos I've taken go directly to the police Josh."

The police?

Josh swallowed hard. Threatening to expose him at work was one thing, but the police was another matter entirely.

"And remember babe," she smiled, running a finger along his inner thigh, so close to his now throbbing cock, "I really will do it, you should know that by now."

"Oh god...no...Dana...please..." Josh found himself begging.

"Mmm...Dana please..." she mocked gently, teasing him. "You know that makes me wet, naughty boy."

"What's it gonna be babe?" she pressed. Wrapping her soft fingers around the fleshy hardness of his shaft, she squeezed.

Closing his eyes, a moan escaped him.

"Are we going to have some more fun?" Dana said, slowly stroking him, pulling hard.

With seemingly little choice, Josh acquiesced...nodding.

"Good!" Dana exclaimed, excited, releasing his cock.

Standing, she extended a hand.

Taking it, Josh stood.

His hard cock jutted straight out from beneath the flaps of his shirt, bouncing slightly with his movement. The thick, swollen veins that lined it filled with the blood rushing through them.

"Oh wait," Dana said, as if she'd just remembered something, pulling him towards the door, "take off your shirt and tie and leave them here babe."

As if in a dream, Josh loosened his tie, pulling it over his head, and dropped it on the desk. Unbuttoning his shirt, he pulled it off and left it next to his tie.

Totally naked in front of Dana, his cock pounded and throbbed at her.

Grasping it, Dana squeezed.

Josh moaned.

Pulling it, Dana led Josh by the cock, out of the door and into the hallway.

Releasing him, she slapped at his naked rear.

"Let's go to the lunchroom babe," she said.

Although it was lunch time, the sounds of the office surrounded him. Some people were still at work in the offices that lined either side of the hall...Josh would have to walk, totally nude and hard right past them.

Without daring a sideways glance, he placed one bare foot in front of the other, feeling the carpet under his feet.

His senses screamed, his nipples grew erect. In front of him, his cock felt like hot iron as it bobbed and bounced.

Passing first one office, then the next, Josh stared straight on...walking with Dana behind him, until they reached the secretary pool on their left.

Daring a glance, Josh saw the pretty black woman who'd come into his office with a message. She sat busy at her computer, unaware of the totally naked man not several feet away.

Suddenly, she looked up at Josh.

Her mouth dropped open.

Josh swallowed hard, and his cock jumped at the idea of being naked and exposed right in front of her at work.