Josh's Dilemma

"Shoes first," Dana said giddily, smiling at him.

Josh removed his shoes, using one foot to push out of his left one, and then did the same with the right.

"Now take off your socks," Dana instructed.

Bending from the waist, he took off each of his socks, and dropped them at Dana's feet.

She settled back in her chair, and spread her legs wider, smiling lewdly.

Josh could see right up her short skirt to the patch of pink panty covering her crotch.

His cock throbbed.

"Now your pants," she said, sounding greedy.

Undoing his belt, Josh opened his fly and pushed at the waist of his slacks, letting them slide down his legs past his knees. With a slight movement, they fell to his ankles. Bending, he stepped out of them and left them on the floor.

Straightening again in front of Dana, his huge, hard cock pressed savagely into the front of his underwear, making a large tent, partially covered by the flaps of his shirt.

Dana's eyes were all over the front of his underwear in excited anticipation.

Josh noticed that the fingers of her left hand played lazily at her nylon covered thigh.

"Get that shirt off Josh," she said, sweet as sugar.

Loosening his tie, he pulled it off.

Then, he unbuttoned his shirt...removing it from his shoulders. Bare chested, he allowed his shirt to fall to the floor. Wearing only his underwear, it was clear that his cock was hard, standing full-erect in the front of his short.

Dana flicked another button on her blouse...and the inside swell of her breasts came into view, just to the edges of her pink aureole...her breasts were larger than they looked with her blouse fully buttoned.

Josh felt his cock jump and pound in his underwear at the sight.

"C'mon Josh," Dana breathed. "Lose the underwear; I wanna see that cock..." Her words were coming shorter, heavier.

In an instant of clarity, Josh realized that if she'd just asked him...he'd probably have stripped for her willingly.

But, then, Josh couldn't know what else she had in mind for him.

Hooking his thumbs under the waistband of his shorts, Josh pulled, lowering them down his waist, to his pubic region.

Dana watched, fascinated.

Josh realized that this was almost like his favorite porn movie.

Dana was dressed like a hot slut, urging him on to strip naked in front of her. His favorite porn movie hadn't blackmailed him of course, but at this moment, that was taking up less of his mind as this horny scene unfolded.

"Oh yeah, Josh, let me see it..." Dana said, demanding.

Slowly, Josh pulled his underwear past his pubic region, showing her his neatly trimmed patch below his belly button. He pulled them over the shaft of his cock, feeling the material rub teasingly against the head.

Finally, he pulled them over his cock.

It popped free. Springing straight up, it slapped off of his belly.

Dana gasped, gobbling it cock with her eyes.

At last, he let his underwear fall to his ankles and stepped out of them...he stood fully naked and hard in front of her.

"God it's big..." Dana said low, in a throaty murmur.

Facing her, Josh's cock jutted straight out at her...his full nine inches standing away from his body. His cock was thick, lined with veins, and it throbbed with his heartbeat. The head of it was swollen purple.

Josh's own breathing was becoming difficult. In spite of his embarrassment, he was incredibly excited...he resisted the urge to touch himself in front of Dana.

"See honey?" Dana said, looking up at him. Batting her pretty eyelashes, she said, "I knew you would like this..."

Dana was gorgeous...Josh thought.

She was also crazy...and dangerous.

She had the power to completely ruin him. But his cock was so hard at that moment, standing naked in front of her, staring down at her nearly exposed tits...right in the middle of her office...that it actually hurt.

"You want touch it don't you?" Dana said, reading his mind.

Josh nodded.

"Not yet, naked boy..." she teased, standing, and re-buttoning her blouse.

Bending over, she showed her pink panty-covered ass to Josh from beneath her skirt, while she gathered his clothes. Retrieving a carrying bag from her coat locker in the corner, she stuffed them in.

"Let's go," she smiled simply.

"Go?" Josh was stunned again.

"Yeah," she said, teasing, "let's go out in the hallway."

Crossing the room, Dana waited by the door with the bag slung over her shoulder. Josh stood his ground, afraid to move.

"Aww, Josh," she cooed in a mock coddle, "remember, the videos..."

With that, Josh pushed himself forward, following her, naked and hard, out into the hall.

Once in the hall, Dana stepped aside to allow Josh to go in front of her. Following behind him, she watched his naked ass cheeks move.

"Your ass is so luscious Josh," she commented from behind him. "You make me wet."

Josh's cock throbbed and pulled at that.

"Where...where are we going?" Josh asked, sounding somewhat worried.

"To the elevator sweety," Dana said matter-of-factly.

Walking through the hall towards the elevator, they passed Josh's office, and the secretary area.

Josh imagined what it would be like if all the desks were full of women, staring at him as he passed. Then, remembering his situation, he pushed it from his mind. But his cock still bobbed, hard and swollen in front of him.

"Too bad we can't do this during the day, huh Josh?" Dana said, catching up with him, and walking beside him.

"What would everyone say if they saw you...walking around totally naked with a big, horny, hard-on at work?"

Josh was silent, hoping he wouldn't have to find out.

When they finally reached the elevator, Josh breathed a sigh of relief. But it was soon replaced by fear as Dana stepped forward and pressed the button.

With a downwards glance at his throbbing cock she smiled. "Going up," she quipped, pleased with herself.

Josh wondered just how far this would go.

As the elevator arrived with a ding, and the doors swooshed open, he was one step closer to knowing.

The interior of the elevator was typical executive style fare. During the day, the mirror-lined vehicle served as the means to come and go from each floor. Josh used it at least twice, nearly every day of his life without thinking about it.

But now, as he stepped in with Dana behind him, for the first time in his life, he felt the carpeting under his bare feet, and saw his nude body reflected in the mirrors around them.

He stood a moment, staring at himself.

The picture of him, totally naked in a public place, with his long, thick cock jutting out in front of him was exciting...somehow lewd.

As Dana stood beside him, he took in her beautiful face, and sexy body. Her blouse stretched tightly across her sizeable, braless breasts, which jiggled when she walked.

The short skirt, nylons and heels that she wore made her look hot...and...desirable. Josh had to admit that he found her very sexually attractive.

And...the whole situation, him totally nude and hard in the elevator, her clothed, yet sexy as hell...made his dick beg for release.

But, Josh realized it was the total power that she was exercising over him that really turned him on...in spite of the potential danger to him.

"Hot huh?" Dana smiled at the reflection, standing beside him. "Look at you, all naked and hard...walking around like this where anyone can see you...you're such a naughty boy..."

Josh's hand moved towards his cock, and he yanked it back. The whole situation, and her sweet/hot voice and demeanor were nearly too much.

Dana noticed.

"Aww," she cooed. "It's okay honey, you can touch it if you want."

Josh was sorely tempted to put his hand on his dick in front of Dana, but held back, for reasons he wasn't quite sure of.

"Go ahead babe," Dana prodded, "touch it...feel your cock for me, right here in the elevator."

Setting the bag with his clothes on the floor, Dana stepped closer, moving within inches of Josh.

He could smell her sweet perfume.

"Will this help?" she asked sweetly, into his ear.

Unbuttoning the top three buttons of her blouse again, Dana revealed the tops of her gorgeous breasts to him.

Despite himself, Josh turned his head and stared into her cleavage.

His hand went to his cock.

The line was crossed, he thought, slowly stroking along the length of his engorged penis in the elevator as Dana watched, inches away.

"Yeah, stroke that big, fat, cock for me Josh," she whispered.

"Look at us in the mirror Josh..."

The mirror showed them standing side by side, nearly touching...but Josh removed himself from the situation, seeing instead, a stark nude man, stroking his cock next to a gorgeous, fully-clothed woman in an elevator.

He could barely breathe.

"I knew you would like this," Dana said throatily, devouring Josh with her eyes in the mirror.

Josh stroked himself slowly. A small moan escaped his lips.

Turning, Dana pressed the button for the top floor.

The elevator moved, taking them upwards, as Josh stroked himself. Everyone was long gone, so the elevator did not stop at the 3 floors separating them from the top.

A few moments later, the elevator arrived at the parking level.

As the doors opened, Dana picked up the bag and stepped through. "C'mon naughty boy," she said, "keep stroking that big cock for me."

Still stroking, Josh stepped from the elevator, and peered through the glass windows of the small entrance way that led from the elevator to the parking lot.

Although it was later in the evening now, the summer sun was only beginning to set. It was light enough to be seen as they stepped through the doors onto the parking deck.

While it was mostly empty, a few cars were still scattered here and there, probably belonging to people who worked in the other building, on the opposite end of the shared lot.

Josh felt a mixture of fear and excitement as he stood, naked, next to Dana, outside on the deck.

Glancing at the other building, Josh realized that he would be possibly visible to anyone in one of the many windows facing the parking deck.

His heart stopped in his chest, but his cock throbbed in its place.

"Dana, I..." he began, shakily.

"Hmmm? Something wrong sweety?" she said, turning to face him. Seeing his expression, she smiled. "We're almost there honey," she said, reassuringly.

Reaching for Josh's hand, she smiled. "C'mon naughty boy."

Josh took her hand, partly because he needed comfort at that moment.

Despite the fact that he didn't trust her...he wanted to...needed to. Placing his hand in hers...feeling her skin on his, sent electric shocks through his body that ended in the head of his cock.

Looking down at himself, he saw a drop of pre-cum beginning to form. His cock ached and throbbed, pulsing in time with his heartbeat.

As they stepped off onto the parking deck, Josh's senses were suddenly alive.

All around him he could hear the sounds of the after-work evening. Traffic on the street below...the sounds of people and machines were everywhere.

His hard-on bounced in front of him, standing out as he walked, naked and barefoot across the parking lot with Dana, her heels clicking on the pavement.

He'd never felt more exposed and vulnerable...yet...he'd never been more excited.

Everything about the experience, the sights, the sounds, even the feel of the pavement under his bare feet...all of it served to underline the fact that he was stark naked, out in a public place...and that Dana was so fully clothed, while he was so nude.

His hand returned to his cock, and he stroked himself openly, walking along hand-in-hand with her.

She smiled at him.

Finally, Dana came to a halt in the middle of the parking deck.

Releasing his hand, she stepped back and set the bag down.

"That's it," she said hotly, "stroke that big cock, right here where anyone can see..."

Spinning his head in all directions confirmed her words. He would be visible to anyone in any of the tall buildings.

But he couldn't stop.

Squeezing his cock, he stroked the length of it, from the base to the head and back again.

"Oh god, that's hot Josh," Dana prodded, snaking a hand down the side of her nylon-covered thigh.

Josh watched her in reverie, stroking his cock faster. His breathing came shorter.

"Yeah, naughty naked-boy," she cooed sexily, "beat your dick...do it...right here in front of me...god, Josh, look at you, totally naked in public..."

Her words spurred him on.

Josh stroked faster, no longer caring where he was...all he could think about was how it exciting the whole situation was.

Moving her feet apart, Dana planted them on the pavement and spread her legs, thrusting her hips out, lewdly at Josh.

"God yes, beat that cock," she said like a wanton slut.

Any and all thoughts of resistance from Josh were long gone. The fact that Dana was blackmailing him was irrelevant now, and in some weird way it excited him...she was forcing him to be naked outside...and jerk his cock for her.

Spitting on his hand, he grabbed his cock again, and beat hard.

"Fuck. That's hot." Dana reciprocated, moving her hand under her skirt.

"I want you to cum for me naughty boy," she said slowly, deliberately, "I want you to cum all over yourself right in front of me...and anyone watching you right now..."

"Yes...Dana..." Josh breathed, struggling to get the words out.

"Mmm..." she murmured, raising her skirt. "Yes, Dana...I like that..."

As Josh watched, stroking his cock, Dana raised her skirt above her crotch, showing him her pink panties.

"You want this, don't you dirty boy?" she cooed naughtily, with a wicked grin at him. "You want to be totally naked out here in the parking lot in front of me..."

"Yes," he answered.

"Yes...what?" she said, teasing him mercilessly.

"Yes....Dana..." Josh said, on the edge of orgasm.

With that, holding her skirt at waist level with one hand, Dana slid the other into her waistband and stroked lightly at her pussy inside of her panties.

That was all it took.

Josh came...hard...pumping his cock and groaning.

Suddenly, his cock spasmed, sending thick, hot, white ropes of cum flying far out in front of him, hitting the ground at Dana's feet. His hand flew over his cock in a blur...and his knees buckled.

Dropping to a squatting position, he moaned long and loudly, shooting his orgasm out on the ground in front of him.

Dana watched, fascinated, playing at her cunt lips inside of her panties.

"Oh god, fuck. Yeah Josh, that's sooo hot," she teased. "Cum, dirty boy, cum for me...cum for Dana..."

If multiple orgasms were possible for a man, Josh would have cum again at the sound of her voice. Looking up at her, he jerked his cock hard between his spread thighs and whimpered, moaning, unable to stop.

"Oh god, Josh," Dana whimpered, thrusting at herself inside of her panties, "this is hot fucking hot...yeah, cum all over the ground like that...you're gonna make me cum..."

Josh squeezed out the last of his cum, in a grimace, wetting the ground in front of him, as Dana came, moaning, jamming her fingers inside of her horny cunt beneath her panties while Josh watched.

Finally, when his orgasm was done, Josh collapsed, sitting down, naked on the pavement. He dropped his head, trying to recover, feeling the shame already beginning to build inside of him.

He heard the sound of Dana's heels approaching.

Raising his face, he looked up at her.

She smiled.

With one hand, she gently stroked his hair, wetting it lightly with her pussy juices.

"You're such a good boy," she cooed...gently, almost lovingly.

The bag with his clothes in it hit the pavement next to him.

Josh was confused.

"I think we're going to have a lot of fun together Josh," Dana said.

With that, she turned and strode off in the direction of one of the parked cars, leaving Josh's clothes next to him.

Josh watched her go in stunned silence.

As he reached her car, she turned to him again.

"Remember Josh," she called out, "I always keep my promises..."