Pleasure & Business

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
HeyAll
HeyAll
22,019 Followers

"Thank you," Jenny breathed a weighty sigh.

"Would you like to see what your good friend Cassandra is doing at this very moment?"

Jenny squirmed where she stood. "Yes, please."

The right side of the blindfold was again lifted. Jenny saw that Cassandra was on her hands and knees on the side of the large platform. The setting reminded Jenny of a stage, and it looked like Cassandra was the main attraction. Jenny felt a brief pang of envy.

Cassandra's blindfold still in place as she rocked to and fro while sucking the massive cock of someone who was standing on the floor, in front of the slightly elevated stage. The gentleman was a stranger to Jenny. He was still fully dressed in an expensive looking suit. His pants were unzipped and his dick rocked in and out of Cassandra's mouth. The man tugged on the leash, encouraging her to take him deeper into the warm recess of her mouth. Cassandra sucked unabashedly. It was obvious that she had embraced her submissive role and this exhibitionist setting.

Jenny gasped.

"This room is full of whatever you desire. Care to have a turn?"

"I..."

Lady Laura rubbed Jenny's nipple gently, then pinched it firmly. "You can always use the safeword. But that would mean missing out on what your pussy craves, wouldn't it? So, I suspect you'll follow my commands. I'll find something suitable for you. Something special for your first time."

Before Jenny could reply, the domme pulled the blindfold back down and ordered her to drop to her knees. Jenny obeyed and knelt on the wooden floor. She was made to crawl forward as the domme pulled the leash in a proprietary manner. As she moved, Jenny heard the conversations around her becoming louder. She knew she was being pulled to the platform.

Lady Laura paused and said, "Up the stairs with you."

Jenny felt her knees come in contact with another solid surface, and she knew she had to navigate the steps carefully. She tried to be as graceful as possible, mindful that some attention was now being turned towards her ascension.

Finally, the tugging on her leash stopped. Continuous moaning, from both a man and a woman, provided background noise to the more intense sounds of sucking and slurping that lay directly in front of Jenny. Her nostrils were filled with the scent of body sweat as she remained frozen in place.

"Use both hands and reach forward," Lady Laura commanded.

Jenny lifted her arms in front of her, with her palms open. The feel of soft, pliable flesh took her breath away. She recognized the form of a bare female bottom in both of her palms. It was Cassandra's ass, Jenny knew without a doubt. Jenny wasn't able to stop herself as she kneaded her fingers into the warm skin. She sensed Cassandra jerk from the unexpected contact, but it was only for a very brief moment.

"You know whose ass that is, don't you?" Lady Laura said playfully. "Cassandra is still sucking away on that hard cock and loving every minute. Now, it's your turn to use your mouth. Go ahead. Or, do you need some extra encouragement?"

The surrounding audience had quieted as Jenny gulped.

"I...I..." Jenny stammered.

"I'll give you a hand. We both know you want this... need this. Cassandra wants it too. She's been such a good girl; I promised her a special treat."

Lady Laura leaned forward and caressed Jenny's hair, before grabbing a handful. Then, the domme guided Jenny to bend forward and rest on her hands. She was now positioned doggy-style behind Cassandra, who was situated similarly. Ever-so-slightly, Lady Laura inched Jenny's face forward until it was pressed solidly into the bare ass and pussy.

Jenny felt her nose push against the crinkled skin that lay between Cassandra's cheeks. Cassandra's muscles tightened in response and then she very subtly pushed back against Jenny's face.

"Tongue," the domme said. "Up and down. You will give attention to both her pussy and ass."

Jenny complied and stuck her tongue out, touching the walls of Cassandra's pussy. Both of their cunts twitched in anticipation. Jenny had never eaten a pussy before. But, she knew what she enjoyed when men had done this to her. At a leisurely pace, she ran her tongue up and down the wet center of her friend. This was her first real lesbian experience and it was thrilling.

The relationship with her friend would never be the same. Ever. She had seen Cassandra naked, being spanked, and sucking cock without shame in front of a room full of people. And now, Jenny was on her knees eating Cassandra's pussy and ass in front of that same crowd.

The hand behind Jenny's head pushed harder, and Jenny put her tongue deeper inside of Cassandra's pussy. While her thoughts and tongue were occupied with the sweet taste of Cassandra, she felt a small leather paddle tap her inner thighs.

"Spread your legs," the domme said. "I'm going to spank your pussy. Gently and lovingly. And you will like it."

Jenny believed she may have gone crazy. This was pure madness! But she had already come this far. Her pussy was demanding attention and looked forward to contact with the paddle.

She buried her face in Cassandra's exposed core. Then she spread her own legs and felt a surge of kinky delight as she imagined the throng of people seeing her most private parts.

There wasn't much time before the shocking strikes began. They were placed on her ass at first. While Jenny continued to eat away at Cassandra's juicy pussy and ass, the domme began to lower the target of her blows. The stinging jolts on Jenny's pussy radiated up her spine and spread out to her entire being.

The slaps weren't hard, Jenny knew she was being treated more gently than Cassandra had been. These were more like a series of soft blows meant to engage Jenny's clitoris and labia. The strategy was extremely effective. Jenny had never tasted this pleasure before and found it incredibly stimulating. It was unlike anything she had ever imagined.

All the while, she wondered how many people were enjoying this sexually explicit show. The crowd must have been affected by the blatantly devious acts because the number of conversations seemed to have diminished. Cassandra continued to suck cock while Jenny ate pussy and Lady Laura continued to entice Jenny's cunt with the paddle.

Soon, a new sound emerged. It became obvious the paddle was striking wet flesh since it sloshed a bit when contact was made. Jenny accepted that she had never been this hedonistically affected before.

"I wish you could see this," Lady Laura said, while continuing to tap Jenny's pussy. "My paddle is dripping with your fluids. You really are a naughty girl, after all. Now I will make you to cum as a reward."

The domme reached below and rubbed Jenny's clitoris in a powerful circular motion with two fingers. Jenny knew that the domme had done this countless times to her subjects over the years. Her experience showed, and it worked.

Jenny's pussy tensed so hard that she needed to cry out, even as her mouth was still buried in Cassandra's body. The vocal vibration must have been felt by Cassandra, because she started to rhythmically jerk at just that moment.

Jenny came with a force that made all of her previous orgasms seem tame. Her butt cheeks clenched strongly and she had to fight to keep her legs open. She knew that her fluids were so copious they must be overflowing onto the floor. It was embarrassing, but freeing at the same time. She had reluctantly given over control to the domme and in exchange, was pushed to a state of orgasmic bliss. The combination of submission, pussy licking, exhibition and punishment had all contributed equally to her overwhelming orgasm.

She had entered the event as a highly educated lawyer, but over the course of the evening, became a servant, who had relinquished control. Her mind was numb and she realized that she relished the change in status. She began to feel more confident that she had found a new facet to her life.

As she came down from her climax, Jenny leaned her forehead against Cassandra's ass to catch her breath. God, she needed recovery.

"Well done," Lady Laura whispered in her ear. "Now you've earned the right to have your blindfold removed. You also deserve a nice, hard cock."

The blindfold was pulled away, and Jenny instantly wished that it had remained in place. It was far easier to come to terms with her self discovery when the crowd was shielded from her view. People watched her as they enjoyed their food and drinks and conversations continued. Her previous moment of calm disappeared as she realized that she must have looked like a complete whore. She prayed that none of those in attendance were part of the business she'd be representing legally.

Looking ahead, Jenny realized Cassandra was now sucking two cocks. She would alternate from one to the other while her head bobbed. She knew that Cassandra was a sexually advanced woman, but to suck two cocks like that, it was something far beyond Jenny's imagination.

Then she turned and saw Dave approaching. The man who had hired her had been watching this whole event? Was this just a powerful coincidence? Or was this part of his plan?

He stood before her, unzipped his pants and revealed his hardened penis.

"Finally," he exclaimed. "Now I get a turn."

Lady Laura smiled, still leaning over Jenny. "You heard the boss. Now you can enjoy giving pleasure to him."

The domme lifted Jenny's head with her hands. She used her fingers to pry open Jenny's mouth as a symbol of dominance. Dave stepped forward and inserted his rock hard cock inside. Jenny knew what was expected of her and closed her lips around the pulsating mass of flesh.

She sucked Dave's cock on her hands and knees right alongside Cassandra, who was still busy sucking two cocks of her own. It gave her a feeling of power, which seemed strangely at odds with her act of submission. She knew Dave was peering down at her and enjoying the carnal consummation of his desire.

"Deeper," the domme added. "Take him in your throat, the way a naughty girl should."

And so the cock went deeper in her mouth until it reached the entrance of her throat. She took it as far as it could go without making her gag and then she took it even further. Tears formed in her eyes as she fought her gag reflex. But she carried on, enjoying the challenge of taking Dave to the hilt.

Jenny's mouth, which had long been an asset in her educational training and legal career, was now being used to pleasure her new boss and to entertain guests. She kept sucking while the domme tilted Jenny's head upwards so that her eyes would remain trained on the boss.

"Suck that cock," the domme said. "Make him cum. Be a good girl. We're watching you embrace your salacious side tonight and you can be sure it's making all of us horny. There's power in submission, Jennifer. Suck him deeply and eat his cum. You're driving him wild."

It felt as if a fire had started in Jenny's soul and she reached up to stroke Dave's hard cock with confident hands. Her sucking became more nuanced and her tongue tickled his tip when she would draw back. His body instantly responded and his facial expression was unmistakable. Dave was in awe that this highly trained lawyer could handle a cock with such innate skill.

She didn't just crave his climax, she was driven to leave a lasting impression. It wasn't that she was doing this for the job, she acknowledged to herself. Rather, she felt like she belonged here, on her knees, bringing sexual gratification to another. Her earnest approach worked, and within moments Dave began to grunt and shake. His cock throbbed vigorously and soon the back of Jenny's throat was coated with his cum. It shot in several bursts and she kept her lips tightly around the shaft, so she was able to consume every last drop.

"Oh God, you are such a good girl," he smiled.

Jenny showed just how much of a 'good girl' she was by sticking her tongue out to show Dave. Her new employers were impressed. When she turned her head, she saw that Cassandra was impressed too. Cassandra's mouth and lips were covered in the cum of two different men.

***

In a few short months, Jenny's life changed dramatically. She began as another broke attorney, who struggled to make ends meet, and finished as a fiscally comfortable lawyer with a corner office in a downtown highrise. Two floors on that building had been leased for their new corporation.

That fateful night led to many other similar encounters and now she had over a dozen clients who were part of that deviant world.

Today she was meeting with 4 of those new clients who were all successful businessmen. She hadn't expected it to turn out this way and she was thrilled at the outcome.

One thing she did know was that before this meeting was over, she would welcome four cocks into her body. What she didn't know was how she'd be receiving them.

Jenny soon found herself bent over the desk. Her gray blazer lay in a wrinkled heap on the floor and her black silk blouse was puddled on the desk. She was wearing a black sheer corset that a laced up the back. The bottom of the piece had straps from which she could attach her black stockings. Jenny had given up wearing underwear to work several weeks ago. The straight gray skirt she wore was hiked up over her hips. Dave had instructed her to assume this position, and she wasn't one to object. Not in her official job capacity, at least.

One by one the men took turns fucking her. They kept her bent over so they could access her from behind. The side of her face was flat against her desk, while the men used their hands on her hips for leverage. Jenny could feel the bruises form on the fronts of her thighs from the force of their bodies as their cocks pummeled her pussy. It brought a sweet smile to her face. She came three times, nearly four, but it became harder to climax after the relentless back-to-back fucking.

There were four legal documents neatly lined up on the desk. After each man came, they'd tuck their cocks away and put their signatures to paper.

"A signing bonus," as Dave had described it.

The last guy pulled out, leaving Jenny's gaping pussy exposed to the people in the room. She felt a combination of humiliation and exhilaration as cum spilled out of her cunt and ran down her thighs. The new clients left after exchanging handshakes, while Jenny remained in her submissive position. On the way out, Jenny's ass received a few powerful slaps, making her butt turn red and hot in the process.

When it was all done, Jenny sprawled out on her new leather couch. Her heels were off and her stockings had been unfastened and gathered in the middle of her thighs. Cassandra was on her knees performing 'cleaning duties,' on Jenny's used cunt. She lapped and swallowed the semen as it poured out of Jenny. They sometimes joked that this really forged new ground in the role of a paralegal by fairly significant margins.

"We did it," Dave said, sitting behind Jenny's desk. "The new business is strong and there's a good possibility for expansion."

Jenny gave a wry smile and exhaled slowly as she was being eaten by her assistant. "Is this actually considered work?"

Dave chuckled. "I love the new you. To be honest, I never thought it would come to this, and I couldn't be more thrilled."

There were slurping sounds in the room as Cassandra continued to probe Jenny's pussy, seeking out every remaining drop of cum. As Jenny's toes began to curl, Cassandra knew her boss was edging closer to another orgasm. She readied herself for the additional wave of cum that would be expelled by the force.

"Hmmm.... I can't believe this either," Jenny moaned as a result of Cassandra's oral skills. "I don't know if I'm fully used to it yet, but I'm enjoying it all one step at a time. Or, one lick at a time, as you can see."

"It's obvious that you find this thrilling. Speaking of which, watching you all morning has been torture. Will you indulge me?"

He stood and approached Jenny, who now had a gleam in her eye. She knew what would happen next. He stood in front of her face as she slouched on the couch. Then he unleashed his erection, which had been fighting to be freed from his pants for quite some time.

She smiled. "With pleasure, Sir."

As her pussy was still being eaten by the ever-so-loyal Cassandra, Jenny leaned forward, grabbed the cock by the shaft, and it took it inside her mouth as the fickle line between work and sex moved yet again.

Jenny knew exactly how Dave liked to be pleasured. She sucked so hard that her cheeks looked caved in. The tip of his cock longed for the teasing of her tongue as she slowly pulled back before plunging back down and engulfing his length. Then came the trek deep into the back of her throat, to which he had become accustomed. When she stroked him fast, he came in her mouth, coating her tongue and the back of her throat with his own seed.

"Good girl," he groaned, the last drops of his cum dripping onto her tongue.

Jenny looked up at him and gave a "ta da," while sticking her cum drenched tongue out like a puppy.

Happily, her lips smacked together and she swallowed.

The End

Special thanks to SueDanym and journey1970.

Your votes & comments are appreciated.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
wagonet2wagonet2over 6 years ago
Bondage that is not revolting

Finally! After liking another story of yours, I tried this one, and was pleasantly surprised at the very decent and human way you told a bondage tale. Very well done.

JJMemaw0623JJMemaw0623over 6 years ago

I love reading your work so I wasn't surprised by the wonderful job done to this story. I hope you continue this storyline as it has great potential! Please keep writing!!

donny70donny70over 6 years ago
Legally well done!

In life we have many legal aspects with which we must deal, but none as interesting and enjoyable as the attorney in this story. She definitely believes in attorney client privilege.

Great Story!

Keep up the good work and I look forward to more...

happydutchguyhappydutchguyover 6 years ago
A new favorite story!

Well written, with a magnificent build-up. Jenny's anxiety was palpable, as was her release when Laura explained there is 'power in submission'. Thank you.

AnonymousAnonymousover 6 years ago
Class act

Love your work!

Show More
Share this Story

Similar Stories

Outsourcing His shrewd wife taps ready young coed for booty duty.in Anal
Room Service Cum Eating Daphne eats cum from a wife’s freshly fucked pussy.in Group Sex
Secretary Gangbang Service Naked, bent over, and fucked on the desk.in Group Sex
Roommates or More? Co-ed roommates deal with clothing-optional living.in Exhibitionist & Voyeur
Accidental Gangbang Wife-to-be ends up fuck-slut at her fiancé's bachelor party.in Group Sex
More Stories