Josh's Dilemma: Resolved

"Josh? Dana?" Mr. Clearly, the last one to leave, turned to them from the whiteboard. "A few of us are meeting at Charlie's for lunch, would you care to join us?"

Josh was speechless. "I..uhm, I mean..." he stammered, his voice dying in his throat.

"Thank you sir, but we're going to stay here and go over some stuff," Dana smiled sweetly at Mr. Cleary, coming to Josh's rescue.

"Fine then," Mr. Cleary nodded. "By the way," he said before leaving the room, "you two have been doing a fine job."

"Thank you sir," Dana smiled again.

Josh nodded dumbly.

At last, Mr. Cleary exited, leaving the boardroom empty save for Josh and Dana.

Josh blew out, exhaling deeply.

"God that was hot," Dana said, standing.

Moving to pull his pants up, Josh pushed back from the table.

"No hun," Dana said quickly. "Take off everything."

"What?" Josh said, shocked.

"You heard me sweety, get naked."

"But Dana," Josh protested, pointing at the open door. "What if someone comes in?"

Dana giggled wickedly.

Crossing the room to the doorway, she stuck her head out.

"Everyone's at lunch honey," she said, turning back to Josh. "Now, please, babe, get those clothes off...shoes, socks, everything...I want you totally naked."

Josh eyed the flash drive on the table.

"Oh," Dana laughed, "I told you before that if anything happens to me babe, those videos of you jerking off naked in your office will go out anyway."

"I know...I know," Josh said, resigned.

"One day honey," Dana began sweetly, stepping closer, "maybe, one day, when I've gained your full trust, we won't need those videos..."

Maybe there was a way out after all, and Josh seized it.

"Dana, you don't have to blackmail me. I would do what you want anyway," Josh smiled, trying to sound convincing.

"Mmmm..." she cooed. "I'm not as dumb as you think babe," she said seriously, then giggled again.

"Now get those clothes off...shoes first."

As Dana watched eagerly, and with little choice, Josh pushed first one shoe off, then the other, using his feet. Then, he dropped his pants to his ankles and stepped out of them, leaving them on the floor. Reaching for his tie, he loosened it, pulled it over his head, and dropped it on the table.

Dana smiled again and eyed his cock.

Finally, Josh unbuttoned his shirt and pulled it off, dropping it on the chair.

His socks were last.

He stood, totally nude, barefoot, and hard in the boardroom in front of Dana...his clothes scattered between the table, chair and floor.

His cock pointed straight at her.

The thick veins stood out as it throbbed upwards with his heartbeat. All nine inches of it stretched the skin around his shaft tightly.

"God it's big," Dana cooed sexily. "You're so hot Josh," she said, licking her lips.

"Dana," Josh begged, "please...what if someone comes in here?"

"Oh god," she said with emphasis on the word god, "it makes me wet when you say, Dana please..."

Moving quickly, Dana gathered his clothes as well as the flash drive from the table as Josh stood watching, helpless and naked, on display in the boardroom, in front of her.

"C'mon babe," she winked at him with his clothes in her arms, "we've got an hour." With that, Dana turned to leave the room.

"Dana wait!" Josh exclaimed behind her. But Dana was already through the door.

Josh panicked.

Naked and hard, with no way to cover himself, Josh padded across the carpeted floor after her.

Every nerve in his body stood on end as he walked naked behind Dana through the reception area. Spinning his head, he tried to see everywhere at once.

The desks by the secretary area were thankfully empty. It seems that she was right, everyone had gone to lunch.

A phone rang behind a door to his left and scared the hell out of him.

Dana stopped and turned to face him.

"Wait here babe," she said, "I'm just going to grab the bag. I'll be right back."

"No, wait, Dana," Josh implored, "don't leave me here..."

Dana softened.

"Oh beautiful man," she said gently, eyeing Josh's nudeness. "Don't worry, your Dana will be right back, I promise..." she said, smiling in earnest, referring to herself in the third person.

Josh watched, helpless, as Dana disappeared down the hall with his clothes, turning into her office.

Despite the fact that he was totally naked, or perhaps because of it, his senses were alive.

Every sound was magnified a hundred fold. Josh was scared to death, and yet, somehow, the thought that he was completely nude at work, during the day, made his cock throb and pull, and jump.

He could be caught at any moment. But that somehow made him shiver with desire. His nipples were erect. He felt the air on his bare skin and the carpet under his feet.

Josh closed his eyes; his hand strayed towards his cock.

"Ready babe?" Dana reappeared in the hallway, smiling at his hand on his cock. The same bag that she'd kept his clothes in before hung from her shoulder.

"Ready?" Josh repeated, shocked, yanking his hand away. He was ashamed that she'd caught him.

"Good, let's go," she said, stepping towards him.

"Go?" Josh said again dumbly.

In answer, Dana stepped closer still, until the skin of her thigh nearly brushed the tip of Josh's hard penis, and lightly pressed her breasts into his bare chest.

"Joshie, I know this turns you on. You might as well admit it...you love being naked in front of me, and you love being naked where you shouldn't...look at you...so hard...I bet your cock hurts..."

She smiled up at him and batted her pretty eyelashes in a wink.

"A moment ago, I saw you touching yourself babe," she went on. "Pretty soon, I'll have you totally naked, jerking your cock in front all the pretty girls here..."

Josh's cock responded for him, pulsating hard, as she pressed her thigh into it.

"Wouldn't you like that Josh?" she teased, twirling a finger in his chest hair. "Wouldn't like to be naked in front of all the women here...and jerk your big cock while they watch?"

Dana's nipples were hard nubs beneath her blouse. Her cleavage rose and fell with her breathing.

"God Josh," she whispered, pressing harder into him, "I want to watch you stroke your cock while I play with myself."

Josh's mouth opened on its own accord...he was breathing hard...his hand moved towards his cock again.

Looking down between them, Dana smiled.

"You wanna see me play with myself, don't you Joshie?" she teased, and waited for a response.

"uh..." Josh stammered.

"Say it babe," she teased again, pressing her bare thigh hard against his cock.

"Say, I want to see you play with yourself Dana..."

"I want...I..." Josh's hand was on his cock now. Eyes closed, he felt he warm body pressing into his.

"I want...to see you...play with yourself...." He managed, now finally openly stroking his cock.

"Mmmm..." Dana cooed, low, "keep stroking it...slowly..."

Taking his hand, Dana smiled, and led him along the carpet hall. Side by side they went, Dana fully clothed, and Josh fully naked, stroking himself as they walked.

They passed the secretary area again, and then turned right towards the elevator.

"But Dana," Josh breathed, "it's the middle of the day..."

Dana smiled in return as she pressed the button.

Once inside, Josh remembered what he had looked like the last time, standing naked and hard next to Dana in the elevator. Once again, the mirror-lined walls showed a lewd sight....him completely nude, and hard. His huge cock swayed and bounced in front of him, as he touched it in the mirror.

Standing next to him, Dana smiled at their reflection, and raised her skirt slightly, showing him her white panties.

Josh moaned, stroking his cock as the elevator moved downwards.

"That's it babe," Dana whispered, flicking her tongue over his ear quickly. "Stroke that big nasty cock for me...mmmm...god...but do it slowly, I wanna play with myself in front of you..."

Almost as if in response, Josh's hand slowed, pulling on his cock, twisting it.

As the elevator stopped and the doors opened, Dana stepped out into the lobby.

Josh followed behind her pulling on himself.

They passed behind two women to the right, who had their back towards them. The women were busy studying the office directory and took no notice of the woman and totally nude man passing not several feet behind them.

"Oh my god!" a female voice exclaimed suddenly from the left.

Turning his head, Josh saw an attractive young woman exiting the restroom.

She stopped dead in her tracks and stared.

Josh's cock nearly exploded in his hand, as he walked on, behind Dana, stroking himself in front of the woman.

When they reached the doors, Dana pushed them open, and went through, with Josh right behind her.

Out on the sidewalk in front of the building, the sounds of the day were deafening. There were people everywhere. The noise of the city, the traffic, horns, people, all of it...rose and pounded in Josh's head as he went, totally naked out in public, slowly stroking his cock behind Dana.

He watched her move in front of him. Her short skirt rose and fell, revealing small snatches of her fleshy ass cheeks over and over again.

The excitement of being totally naked in public rushed through him, stealing his breath and swelling his cock harder than it had ever been before.

Dana's heels clicked on the pavement, in front of him as she swayed sexily down the sidewalk carrying his bag of clothes...his only means of covering himself.

Spinning his head again, trying to see everywhere at once, Josh was amazed at the number of people who seemed not to notice him. He marveled at how he could walk along naked on the sidewalk next to the street in the middle of city.

But some did notice. A few cars slowed next to them, while the occupants gawked at the naked man walking down the street, jerking his cock.

One girl shouted "LOOK! THAT GUY'S FUCKIN' NAKED!" from the window of a car.

"OH MY GOD! HE'S JERKIN' OFF!" another voice joined in.

Josh nearly came at that.

People on the street stared wide-mouthed as they passed.

Finally, turning into an alleyway between two buildings, Dana came to a halt and dropped the bag on the ground.

Scattered with trash here and there, the alleyway was lined with dumpsters, but was devoid of people.

"This is what you want isn't it Josh?" Dana said, stepping closer, lifting her skirt.

"You want to be totally naked in public don't you?"

All but gone, Josh's head was back on his shoulders, eyes closed as he stroked himself.

"I know babe," Dana cooed, moving closer until she stood right in front of him. Josh's hand flew on his cock, as his knuckles brushed her leg.

"I know you honey...I know what you want..." she said, pressing her bare thigh into his.

Just then, a couple, a man and a woman passed the end of the alley on the sidewalk. Spotting Josh, they stopped.

"What the fuck?" the man said, shocked.

"Come on babe look at me," Dana said sweetly, sliding a hand into the waistband of her panties.

Josh opened his eyes.

Dana had undone the buttons on her blouse, down to her naval. The insides of her luscious breasts were bared to Josh's eyes.

With one hand, she diddled herself in her panties under her skirt. With the other, she reached behind Josh's head, and gently pulled it down, pressing his face softly into her warm cleavage.

The couple, fascinated, had moved closer, until they were standing a few feet from Josh and Dana.

Turning his face from Dana soft breasts, Josh opened his eyes.

The couple watched, glued to the spot as the totally naked man stroked his enormous cock in public, with his face pressed into the beautiful woman's cleavage.

No long caring, Josh turned his face back into Dana's soft breasts and stoked himself hard, moaning loudly.

"They're watching you babe," Dana cooed softly, tonguing Josh's ear. "They can see you all naked, beating off for them..."

Josh pressed his face harder into her breasts.

"Yesss...babe..." she hissed hotly. "I'm playing with myself for you..."

With that, Josh dropped to a squat.

Spreading his knees as wide as he could get them, he rocked back on his bare heels, thrusting his hips forwards, as the hard ground dug into the bottoms of his feet. His cock pointed straight up in the air.

With one hand behind him, he supported himself and he spit into his palm, fucking it, closing his fist around his cock, thrusting it in and out.

"OH GOD..." he moaned, fucking his fist shamelessly in public as the couple watched.

Dana's hand was busy in her panties.

Spreading her legs wide, she planted her feet, standing over Josh.

Josh stared up at her...lost...bucking his hips wildly, thrusting his cock into his fist.

"Yeah, fuck yourself Josh," Dana moaned, rubbing fast circles hard into her swollen clit.

The couple linked arms, and stared in silence at something they'd never imagined possible.

Squatting over Josh's cock until her pantied crotch was inches from his fist, Dana rubbed hard and fast...soaking her panties. Her excitement rolled down her inner thighs, wetting and slickening them.

Josh stared at her, pounding himself to edge of orgasm.

"Am I pretty Josh?" Dana breathed, slapping at her horny cunt through her panties.

"Yeah..." Josh moaned.

"Please Joshie, say it..." she cooed, jamming her fingers into herself from underneath, along with her panties.

"You're.."

"Mmmhmm..." Dana whimpered, as three fingers entered her dripping snatching, forcing her panties up and into her.

"Oh god..Dana..." Josh breathed hard, moaning loudly as his orgasm threatened.

"Yes, Josh...." Dana's beautiful eyes bore into his.

"Oh god...Dana..." Josh fumbled again moments away...

"Dana, you're so.....SO...PRETTY!" Josh yelled, as his orgasm hit, rocking his body hard.

Cum jettisoned from the head of his cock in thick, white, ropes, shooting straight up, high into the air, before landing all over him, splattering his belly and chest.

Pumping himself hard and fast, he moaned again and again as his cock jumped and spasmed in his fist.

"Oh god, Dana, you're so pretty...you're so fucking pretty..."

Dana came, hard.

Moaning loudly, she pressed her fingers into her cunt, turning them over inside of herself.

Her body shook, rocking her on her heels, as she squirted her orgasm out in front of her, wetting Josh's hand and cock with her hot cum juice.

The couple was stunned...watching the scene in silence.

Dana sprayed her orgasm all over Josh. Moaning and pressing the fingers of one hand upwards into her cunt, she slapped and smacked at her clit with the other...shaking violently...biting into her lip hard enough to draw blood...before crashing to her knees on the ground, fucking her hand, driving herself into ecstasy.

Finally...a few minutes later...they were done.

Josh collapsed, lying on his back on the pavement in a pool of his own cum.

Dana was on her knees in front of him, breathing hard, trying to recover.

Josh looked up at the couple.

They stood a moment longer, before the man pulled at the woman's hand to leave...darting off out of the alleyway.

Rolling on his side, Josh pushed himself to a sitting position on the ground.

"What time is it?" he wondered aloud, reaching for the bag.

"It's time to go Joshie honey," Dana smiled at him, standing and brushing herself off.

Josh pulled the zipper on the bag and reached in.

Frowning, his arm moved frantically as his hand swam in the bag, searching.

"What the fuck?" he muttered, prying the bag open and peering inside.

"Dana?"

Dana giggled.

Turning the bag over, he emptied its contents on the ground.

There was nothing but old newspapers, crumbled into balls and shoved in the bag.

"Dana?" he said again, shocked.

"Where's my clothes?"

"In my office babe," she giggled again, smiling wickedly.

"But...how am I going to get back to the office?"

"Same way you came Joshie babe...same way you came," she said, extending a hand towards him.

Swallowing hard, Josh sat a moment.

It was obvious that she had won.

So far, she'd kept her promise...she hadn't shown the videos to anyone. But did that really matter now? He'd been seen, naked, in public and even masturbating. She'd been seen masturbating too, but she wasn't naked...and she'd only been seen by the couple, who were surely unlikely to tell anyone. If anything, he'd be the one in trouble, not her.

Now of course, she'd tricked him.

He was going to have to walk back again, completely naked, the same way they'd come. The day was as busy as it had been on the way down and he would be seen by as many people again.

Josh dropped his head. It was too much.

As if sensing his despair, Dana stepped closer and knelt beside him. Her beautiful blue eyes bore into his and she smiled.

"No babe, please," she said, gently, as if reading his mind. "I told you that I know what turns you on, and I was right...right?"

Josh nodded dumbly.

"And," she went on, stroking his shoulder softly, "hasn't everything we've done so far been more exciting for you than anything you've ever done before?

Another nod.

Slowly, Dana unbuttoned her blouse all the way and leaned in...the blouse fell open, exposing her entire, bare breasts to Josh.

Smiling, she noticed his cock thicken.

"Babe," she said gently, "look at me..."

Tearing his eyes from her gorgeous tits, he did.

"I know what you want...what you need, Josh...you must learn to believe that."

"Yes Dana," he said simply.

Pressing her soft, warm lips against his, she kissed him, pushing her moist tongue, slowly, almost...lovingly into his mouth, wrapping it with hers.

Josh's cock rose to full attention again, pointing straight up between her legs, throbbing, as she knelt over him.

Gently, she grasped it.

Wrapping her fingers around the shaft, she squeezed lightly, rubbing it slowly against her bare, inner thigh, inches from her sweet spot.

Josh moaned into her mouth at her touch, and at the thought that he was still completely naked in the alleyway being stroked by beautiful Dana.

"You want me, don't you Josh?" she said softly into his ear.

Josh only moaned again in response, as her fingers pressed into the flesh of his shaft.

"C'mon Joshie," Dana smiled into his eyes...palming his balls, lifting them, rolling them between her fingers. Leaning in once more, she whispered low, "it's your choice babe."

His cock swelled hard and throbbed in her palm, as his hips moved involuntarily.

He stared down her blouse, drinking in the sight of her gorgeous bare breasts.

"Fuck my hand," she whispered. "Look at me and fuck my hand Josh..."

Josh bucked his hips, fucking his cock into her palm. She closed her fist around it, watching it move in and out, as she tenderly lifted one heavy breast and pressed it against his face.

Suddenly,releasing her grip on his cock, she stood, re-buttoned her blouse and extended a hand.

Josh sat in shock.

With no other option, or perhaps, because he wanted to...Josh took her hand and stood...his hard-on bobbed in front of him, pointing at Dana.

She'd won.

Dana smiled at him. She really was so incredibly beautiful.

The day was busy, and there was a lot of ground to cover.

Pulling on him, Dana set off, leaving the bag on the ground. Hand-in-hand they made their way towards the street again...Dana fully-clothed, Josh totally naked in public...as his cock bounced in front of him.