In for a Penny

With a deep breath, Penny pushed open the office door, steeling her spine and doing her best to show confidence. She needed this job and judging by the dark-stained wood and brass accents that evoked the feeling of an old-school smoking room, this wasn't the kind of place that would accept mediocrity.

After crossing the threshold, Penny looked around expectantly, but didn't see anyone. Assuming Mr. Hammond, the man with whom she was supposed to interview, was in another meeting, she crossed over to the couch and sat down, but not before glancing in the mirror hung by the door to check her appearance one last time - first impressions were everything, especially if you were interested in a job where yours was the first face customers would see when entering the office.

Penny was a woman of average height, around 5'6" and a little plumper than she would have liked, though she had been told by her last boyfriend that it was all in the right places. She had a trim waist but a well-rounded ass, thick thighs, and a large chest which she tried to keep covered without a hint of cleavage most of the time, since that was all men ever seemed to focus on. Her grey pencil skirt showed off her shapely calves which were displayed to their best advantage by her five-inch black heels, and the matching grey jacket added to the business look, though cinched in a bit too much under her bosom for her liking, seeming to thrust her breasts up for inspection.

"Nothing I can do about it now", Penny thought, while using her pinky finger to wipe away a tiny smudge of red lipstick around her very full lips. Her deep brown eyes were lightly rimmed in black liner, but she otherwise wore no makeup. She'd luckily inherited her mother's perfectly smooth skin.

She crossed her legs and looked around the office, wondering what Mr. Hammond would be like. She imagined an older man who was professional, if a little portly, probably with thinning hair and a red nose. So, she was decidedly surprised when a door opened a moment later and in walked a man who looked better suited to a boxing ring. He was 6'2" if not taller, with short dark hair and just a hint of silver at his temples. His tailored black suit (it had to have been tailored to fit over his impeccably muscled arms and chest) was cut perfectly and his steel blue tie matched his piercing eyes exactly.

"Ms. Ferguson?" he asked in a deep voice that seemed to wash right through her, making her skin tingle and her whole body shiver. "Please come on back."

He turned around without waiting for her to answer and walked back through the door. With another deep breath Penny stood and followed him through a long hallway, the design from the sitting room blending into the rest of the building. He stopped outside an office and waved her inside. He closed the door behind them and gestured to a seat in front of his desk. He picked up the phone and dialed, only saying "she's here" before hanging up and sitting back in his chair with his hands steepled in front of his chest. His eyes did a quick up and down of her torso, all he could see while they were both seated.

He nodded once, then asked, "you read the job description?"

Penny nodded. "It was a bit vague, but it sounds like a great opportunity. I've been an executive assistant in the law industry before so offering support to three lawyers is absolutely something I know I'm qualified to do. And I'm very dedicated and not afraid of working long hours."

Mr. Hammond smirked a bit at that. "The job does entail looking after three lawyers, but it's less of an administrative role and more of a hands-on position. To put it bluntly, Ms. Ferguson, we're looking for someone to file, but you'd spend most of your days on your back, or up against the wall, or on your knees, while one or all of us fucks you. We lead very stressful lives almost exclusively in the office when we're not at court, so having someone here to relieve that stress is of the utmost importance. Is that something you think you can do?"

Penny drew in a breath, frozen to her chair. Prostitution? That's what this sounded like. She needed money, and now she knew why this job was paying so much more than her last. Logically, she should get up and walk out the door. But her body wouldn't let her. She couldn't deny the way her pussy immediately flooded and her heart raced. What would it be like to spend her days being used for sex, slammed against a wall or over a desk whenever the mood struck one of them? And what about when more than one of them wanted her? He'd said it might happen. Just the thought of that made her head spin. She'd never had more than one man at once before, but the idea had always intrigued her. And she could always quit if it got to be too much, right?

Penny coughed lightly, then stared right into Mr. Hammond's eyes and said, "yes, sir."

He smirked again, then pushed his chair back from the desk, slowly undoing his belt. "I'm pleased to hear that, Ms. Ferguson. Now slip off that skirt but leave the heels. You'll need to sign your contract and a non-disclosure agreement while I fuck what I assume is a very tight pussy."

Penny's whole body clenched, but she stood up and pulled down the zipper on the side of her skirt, letting it slowly slide down her body, leaving her lower half clad in her stockings, garter, and heels. She never wore panties. Mr. Hammond's hungry gaze went from her heels to her bare pussy, clearly wet and ready. Without being asked, Penny also undid her jacket which she let fall, then pulled her blouse over her head as she walked around the desk, her lace-clad tits shaking slightly with each step.

"Are these the documents I need to sign?" she asked as she bent over the desk, forcing her ass to graze across the front of his pants. She picked up a pen, trying to focus on writing her name as Mr. Hammond's hands came up and grabbed a healthy handful of each cheek. He massaged them, letting out a slow groan as her pussy lips opened as he spread her more. She began moaning as one of his fingers began exploring her, sliding easily through her wet heat. Slowly, his finger entered her, then curled forward as it withdrew, skimming her g-spot and making her squeal.

"Keep signing" he said, though his voice had gotten even deeper and it sounded like he was breathing a bit harder. Penny moved her hand back towards the pen, quickly signing the lines, not caring what the contracts even said, just desperate to feel more of him. As she put the pen down, she felt his breath against her core, not quite prepared for the feeling of his tongue as it snaked out and ran up her slit. He groaned again, but louder this time.

"You're delicious," he said, somewhat muffled but her pussy. "I'm going to enjoy tearing up this cunt. And you'll be taking it raw. I love to see my spunk drooling out of a woman's snatch, especially one as pretty as this."

With that he stood, flipping her over and tearing off his jacket and shirt before pushing his pants down, finally freeing his cock. It was large, about 8" and thick. She thought she might just be able to get her fingers around it. He certainly could, as he grasped it and jerked it twice, a pearl of precum beading at the tip. He stepped forward, staring into her eyes as he rubbed his dick through her folds, hitting her clit with each pass and making her pussy spasm in anticipation of being invaded. Her legs spread wider waiting for him to make good on his promise of tearing her up.

He leaned over her, grabbed her right leg and wrapped it around him while simultaneously pushing her left knee into her chest. After a few more passes of her slit, he lined up with her pussy and thrust forward, making her take it all and making her scream. There was pain for a split second before it transformed into an aching want.

He pulled back slowly, then thrust again hard, making her whole body shake, his cock grazing her g-spot each time he did it. He looked down at her, mouth set in a grim line as he pumped faster, and her moans grew louder and more frantic. "You'll cum when I tell you and not before, understand?" he asked, sounding slightly winded but no less severe. Penny nodded, unable to speak, especially not after his hand moved down and started playing with her clit.

"You like having me balls deep inside you, don't you?" he grunted. "You like knowing that I'm going to fuck you hard and fill you up with my cum, shooting it way up inside you so it leaks out slowly. You'll be walking around later, and it'll start running down your legs and you'll remember how hard I took you and how hot you were for it. And later when you meet the other partners, you'll feel stretched out from being taken by three men. Three men's cum inside you. And you're going to love it, aren't you? Now CUM!"

Penny let out a wail, so overcome by his words, by his thrusts, by the wrongness of letting her new boss fuck her. Her cunt spasmed over and over, clenching his cock so tightly that he could barely move. She'd never felt anything like it. And she never wanted it to end. But slowly her spasms came further apart and she came back to reality, just in time to see Mr. Hammond's face change and his jaw drop as he started to cum. After two more short stroked, he buried his cock deep inside her, filling her up and letting out one long, low groan.

A moment later he opened his eyes, looking down at her in wonder. "Fuck," he said. "You're going to be the best assistant ever".

He slowly withdrew, his wet cock glistening, as he eased back into his chair. His gaze travelled down to her pussy and he wheeled himself forward, using both hands to spread her lips apart. Penny began to feel his cum oozing out of her but didn't move. Mr. Hammond's tongue came out, licking between her legs, tasting them both. His head came back up, looking past her towards the door.

"You've gotta get some of this," he said. Penny's head twisted, trying to see who he was talking to. Two men, both as large as Mr. Hammond, stood just inside the door, both with their cocks out, slowly jacking themselves off. She looked back towards Mr. Hammond whose lips were shiny with a mix of both their cum. She was certain she'd made the right choice in taking this job.