In for a Penny

Control was something Jason needed in his life, whether he was working with a client, managing his business with his partners, or especially when with a woman. He'd been pleasantly surprised the day before when interviewing Penny that she'd come as soon as he'd demanded. Most women needed a longer session or to get to know him before being able to let go like she had. But Penny just immediately placed her trust in him and he wondered if she knew how rare that was.

He'd just eaten lunch with Mark and Craig, both seeming entirely too relaxed for having so much going on. But as the men began to recount their experiences with Penny that morning, it made so much more sense. That she'd been so adventurous with Craig especially made Jason feel more comfortable with letting his tastes run wild. Mark was easy, he was happy with a suck and a fuck, and was luckily also happy to play around with Jason and Craig on occasion. But Craig's desires were pretty kinky - not many women would indulge his pissing fetish.

Jason reached over to his phone, using the intercom function to call out to the reception desk, now Penny's.

"Yes, Mr. Hammond?" Penny asked in answer to his call.

"Come into my office, please, Penny," he said sternly, masking his excitement.

"Yes, sir," she replied, making Jason immediately wonder if she had experience in a dom/sub relationship. He wouldn't go so far as to call himself a dom, but he did have a particular fascination with women who knew he was in control as far as sex went.

He stood as Penny entered his office a moment later, moving out from behind his desk and pulling out one of the visitor chairs. "Sit," he commanded, staying behind her as she gracefully sank into the chair. Jason leaned forward and brushed the hair away from her ear. "I hear that you've been extremely naughty," he said quietly but firmly. "You've let two men touch you today, come inside you, even piss inside you. Is that correct?"

Penny drew in a deep breath, her cheeks getting rosy. "Yes, sir," she whispered.

"Do you think good girls behave that way? And you liked it, didn't you? You liked knowing you were being defiled, hmm?"

"I did like it, sir," Penny replied. "I know I'm not a good girl for being so dirty, but it made me feel so hot."

"Well," Jason said, straightening up and moving towards the wall. "I think you'll have to be punished for being such a wanton slut. Stand up and remove your clothing."

Penny rushed to comply, quickly stripping off her jacket, skirt, and bra. As she was about to step out of her heels, he stopped her. "No, leave them on," he said. "Now come over here."

Jason waited impatiently while she did so, then stood behind her. He took both of her hands, moving them to press flat to the wall near her shoulders. "Don't move them, understand? Or there will be consequences," he stated, waiting for her nod before stepping away. He moved to a concealed cupboard, reaching inside and pulling out a short whip. He slapped it against his palm once, making a cracking noise and causing Penny to jump and let out a small whimper. He smiled, then set it aside, deciding she wasn't ready for that yet. He walked quickly back towards Penny and wrapped his hands around her neck. She made another soft noise of distress and her breath got heavier.

"Just say stop if it becomes too much. But I think you'll like this," Jason whispered in her ear, again waiting for her nod before drawing back his arm and smiling at the sound of his hand connecting with her ass. Penny jumped but let out a soft moan. "You've been such a little whore today," Jason said as he spanked her again. "So dirty, letting those men use you. And since you've proved you can't control your base desires, I'm going to punish you for it. I bet you're wet already, aren't you?"

"Yes, sir," Penny replied as his hand reached between her legs, one finger sliding through her lips as her cunt gushed. He pulled back, spanking her four more times in quick succession before using both hands to massage her cheeks. He spanked her again, his hand moving back to her pussy, entering her with two fingers and twisting, causing a groan to escape from Penny's lips.

"You're going to keep being a slut, aren't you? You're going to let all three of us cum wherever we want. All over your face, on your tits, inside your tight cunt... I bet you'll even let us fuck your ass, won't you? We'll stretch you out, fuck your ass one after the other, dumping our loads inside you as you beg for more. Letting Craig piss inside you or all over you. And every time you do something dirty, I'm going to punish you, understand?" With each question Jason spanked her again, until Penny was pushing her ass back against him, begging for his cock.

"Not yet," he said in answer to her silent demand. "Lie on the couch with your legs in the air against the back and your head hanging down over the side. I'm going to fuck your face."

Penny moved quickly, arranging herself on the couch, hair swinging as she looked up at him, upside down. Jason moved closer, kneeling in front of her and undoing his pants. He pulled out his cock, stroking it a few times before shuffling closer. "Spread your legs," he said, watching as her thighs separated and formed a v. "Wider," he demanded, pleased when she seemed to almost be doing the splits. He leaned forward, his cock brushing her cheek as he pulled his arm back and slapped her pussy. It made a wet noise, she was so turned on. Pleased, he did it again, then twice more before returning his attention to her mouth.

"Open wide and relax your throat," he said, grabbing the base of his cock and lining it up with her open mouth. He slowly entered her mouth, pushing in until she gagged, and kept pushing. He felt her throat start to open and she swallowed once, allowing him to bury his rod completely inside her head. He stayed there for a moment, allowing her to get used to his size, before pulling out almost the whole way. She sucked him hard on the way out until only the head was left between her lips. He sighed in pleasure, then reached forward, grabbed an ample tit in each hand, and began fucking. He thrust his cock into her face repeatedly, stopping only occasionally to let her breathe.

"Fuck. Yes. Fuck," he shouted, close to unloading. She groaned in response, her hands fisted at her sides, her pussy glistening with wetness. Two more thrusts and he stilled, his cock already in her throat, shooting directly into her stomach. He pulled out a bit, so she could breathe, allowing the last few jets to land in her mouth before withdrawing completely. Penny let out a soft moan, rolling his cum around in her mouth, savouring the taste.

"God, I don't think I've known anyone to deep-throat like you. Fuck," Jason exclaimed before standing and helping her sit up. "But you're not forgiven for being such a slut just yet. Go lean over my desk."

Penny stood and moved towards Jason's desk, pressing her chest into the wood, sticking her ass out towards him and spreading her legs. Jason admired the view for a moment, appreciating the way her pussy was dripping with excitement. He trailed a hand over her reddened ass, slapping her lightly one more time.

Stepping up between her legs, Jason lined his cock up to her cunt and slammed it home, fucking her hard. He leaned over, sweeping his hands up her back, brushing her hair to the side before wrapping his hands around her neck, lightly choking her and using his leverage to pull her body back towards him. She grasped at his hands as her pussy began to spasm. Jason immediately stopped moving, holding her tight against him.

"Not yet, princess. You'll come when I tell you."

Penny whimpered then groaned at Jason began thrusting once again. "Yeah, princess. Take my thick cock. I know how much you love it. You're having dinner with the three of us tonight and I have a feeling you're going to need a punishment tomorrow for being so dirty tonight. Think you can take all of us at once? I bet you can. We're going to tear your pussy up, maybe take your ass too.

Jason stilled once more as Penny's gasps became higher pitched, so close to cumming. He moved his hands to grab each tit hard, squeezing until she gasped. He began to move his hips again, returning his hands to her throat, choking her lightly again, knowing he was close. "Are you ready, princess? I'm going to fill up your tight cunt. Then you're going to sit on the chair across from my desk with your legs spread so I can watch my cum drip out of you while I work. Will you like that? Being displayed as the whore you are?" he asked pushing into her faster, getting close. He knew she was ready to cum as well, an almost constant moan coming from her mouth, cut off occasionally as his hands tightened around her neck.

"Fuck. Fuck. Cum for me. Wrap that tight cunt around my cock. Milk my jizz," Jason demanded, his strokes losing their rhythm. He froze with his dick as far inside as he could get, pumping spurt after spurt inside her grasping pussy, clenching hard as she came. "Ah, princess. Yes. So fucking good. You're such a dirty girl."

They stayed like that for a moment, their breaths returning to normal. Jason unwrapped his hands from around Penny's throat, moving down to squeeze both tits quickly, then pulling out. He grabbed her shoulders and moved her towards the chair across from his desk, sitting her down with her ass as far towards the front of the seat as possible and spread her legs. He could just make out a pearl of his cum as it started to leak out. "Perfect," he said. "Don't move."

He stepped into the washroom connected to his office and cleaned up quickly, then returned to his desk. For the next 30 minutes he worked, glancing up on occasion to see Penny sitting across from him, now with a puddle of cum under her ass and dripping onto the carpet. He smirked, pleased with the display. However, he knew she must be getting uncomfortable, so a few moments later dismissed her, walking her to the door and handing over her pile of clothing. With one last spank he shooed her out the door then went back to his desk, not worried about cleaning up the puddle of cum. He liked looking at it, knowing how dirty she was and how much she'd need another punishment soon.