tagGroup SexPleasure & Business

Pleasure & Business


Being a young lawyer with a solo practice generally means taking whatever clients you can get and being grateful about it.

Okay, so maybe Jenny wasn't that young. She was nearly 32, but still at the start of her career. Often, she wondered if working her ass off in college and going to an ivy league law school was more of a curse than a blessing, given how much it cost her in student loans.

It was practically a miracle that Jenny snagged her latest client. Dave was involved with a few mid-sized businesses and she was certain he was worth upwards of a few million dollars.

Their meeting occurred through a last minute invitation she had received from an old college classmate to an art exhibition, where Dave was one of the financial backers. Graciously, he had gone around the room introducing himself and trying to ensure that everyone was having a great time. Dave heaped praise on the artists and their work.

When he finally got around to Jenny, the conversation came naturally as they talked about her job. He seemed impressed and his questions showed his interest. "You're a lawyer? Really? What kind of experience do you have? Actually, you'd be a perfect legal representative on my behalf. No, really. I'm being serious here. You would."

Jenny simply couldn't believe her luck when this mysterious, sharply dressed guy gave her a business card. As she'd later learn, he operated adult related businesses. Surprise, surprise. Just her luck. By no means was Dave a sleaze, but he seemed like a guy who loved sex and was open about it.

Jenny was certain that Dave really wanted to fuck her. She had that effect on most men since she kept herself in good shape and was an effortless beauty. But even so, Dave kept a poker face about his interest in her (sexually speaking). She knew he was serious about offering legit work.

Finally, their attorney/client relationship solidified when he took her out to lunch at an upscale restaurant where they ate outside under the sun.

"I think we can talk business now," he said, taking a sip of wine. "I'll be honest, I have a few lawyers with whom I work."

"Jeez, what kind of trouble are you in?" she said half-jokingly.

Dave laughed. "No trouble at all. Generally, they're causal relationships; I've used different attorneys for a variety of jobs over the years. Most have them have become great friends of mine. But, for this new project, I want you to be my legal representative."

Through the course of their lunch, Dave explained a great deal. The business was adult oriented. Jenny would be tasked with filing the paperwork with the State and becoming the agent for the new corporation. Furthermore, she'd be the head lawyer for that corporation should the need arise. It was considered part-time work at the moment, but they'd offer her a full time job if the business was successful and generated a large cash flow.

The name of the corporation was suggestive: D & S Envy

She didn't ask what the D and the S stood for, but she had an idea given that it was sexual in nature. It was catchy, she thought.

"There's more," he added. "I want you to be in charge of our legal policies. I think you can handle that."

"I'll see what I can do."

"Wonderful. I'm not looking for boilerplate legal templates for policies. I'm talking about something uniquely tailored for us and the experiences we will provide with this new venture."

Jenny raised an eyebrow. "Oh..."

"A good 'oh?' Or a bad one?"

"An interested 'oh.' It sounds like a challenge given the nature of the business."

"Depends on your views," Dave replied. "I'm usually good at reading women. In fact, some say it's a gift. It's helped me thrive with my work. But I can't place you. Not exactly, anyway. And I like that. It's sexy."

Here, Dave was right. Jenny was not a woman who could easily be placed in boxes or categories. Early in her youth, she had done many things she regretted, and had several bad experiences. As a result, she learned to keep her emotions guarded and not show any weakness to anyone she didn't trust.

Sexually this couldn't have been more true. It wasn't immediately apparent if she was gay or straight, dominant or submissive.

She was simply Jenny.

And she was happy with that.

Dave waved a finger. "If I had to guess, I'd place you as a natural submissive. Yes, that's it. I sense a dark side to your sexuality. A need to be owned. Am I right?"

"I'll never tell" she replied with a coy smile. "What are the details of the job? Then I'll let you know if I'm the right choice. Though I must admit, I'm intrigued already."

"Well, what do you think 'D & S' stands for in the business name?"

Jenny pretended to think, but she already knew. "Dominant and Submissive."

"Smart girl."

"I wasn't born on the prairie."

"Never said you were. Look, I'll be honest, the business is fairly hardcore and we'll do a variety of things. For instance, sex shops, toys, merchandise, and a few bondage studios are in the works. It'll be a small franchise of sorts. We'll make sure everything is done safely and professionally. In fact, safety and professionalism are our highest priority."

Jenny pondered this. "It's not like I'm going to fuck anyone, right?"

The question was flippant and she expected him to laugh. Instead, Dave gave a purposefully indifferent pause and relaxed his body language to show that he wasn't going to answer.

"You're kidding!" she snapped back.

He cracked a faint smile in response. "Sort of. I need you to get a feel for the business. You can meet some of the key players, find out what they do, how it all works, and so forth. It could be a real learning experience for you."

"Lawyers call that research. I'd be happy to do "research" for this project. But keep in mind, I'm hesitant about taking a full-time job for a company like this. I mean, I'd love to help you start it, but long-term, I don't know. I'm not sure if it's something with which I'd want to be associated."

"Fair enough," he said with a vague expression.

She sighed. "You've already lost faith in me, haven't you?"

"Quite the opposite."

Jenny squinted her eyes and took a sip of her drink. "Explain."

"I'm offering this job to you for several reasons: You're intelligent, tough, and fierce. I like that you're questioning this, it means that you're no one's bitch. It shows your independence. Your boldness and no-nonsense attitude will help keep our guidelines strict, but fair. You don't fuck around, and that's the kind of lawyer we need. Someone who'll keep everyone in line, yet embraces sex in all its glory, and you're also easy on the eyes. Correction, you're gorgeous to look at."

"Hmmm. A strange set of complements."

"Strange but true. Ordinary isn't my style."

She found herself blushing a little. "If you're trying to sweet talk me, it's working."

"The truth always works," he said with a sly charm. "At least that's my experience. Regarding the business, I want you to get acquainted with what we're doing. Then, make your decision. I never want to make you uncomfortable. That's not my goal."

"Thank you. I respect that."

"I'll email you some material to review later tonight."

Her eyebrow rose. "In other words, porn."

"For lack of a better word, yes," he smiled. "It's all highly private material. I assume this falls under attorney/client privilege, and that the images will never be made public."

She nodded. "You'd be correct. It'll all be confidential."


The more this went on, the more intrigued she became. Maintaining her composure was critical at moments like these; she didn't let Dave know her true feelings. It was against her philosophy as a lawyer to show her clients anything too revealing about herself.

"I'll think about it more after I get your email," she said.

"Jenny, I look forward to our future partnership. Shall we make an early toast?"

They touched their glasses and took a drink, which was ultimately the turning point in her sexuality as a vibrant young woman.


Even before the email came, Jenny was certain that she'd accept the deal, and there were a couple of reasons for that.

First, and most importantly, the money. She needed it and Dave had plenty to spare. As a lawyer, you never know when cases will go your way. Winning is never assured. Getting good, high paying clients to provide a steady cash flow is a rarity for a self-employed attorney with a small office and little experience.

Second, it seemed like a fun adventure. Sure, she couldn't tell her friends or family about this, but that was okay. And yes, she was convinced that Dave desperately wanted to fuck her. The familiar vibes were hard to ignore, but at least he controlled himself and kept things professional.

But the true appeal was the ability it afforded to explore something new, with the benefit of a safety net. The people with whom she would be dealing were likely professionals. Deep down, Jenny did hide a dark side. Dave was correct when he made that observation and felt attracted to it. Jenny hadn't yet acted on her deviant impulses. But, there was a curiosity inside of her that yearned to be cultivated.

The email finally came. Jenny was in sweatpants and wore a blue t-shirt sporting the symbol of her law school. She had her post-dinner coffee, sat at the desk, and read the message:

Hi Jennifer,

As promised, here's some material for you to review. Take as much time as you need. Think it over carefully. I will respect your wishes if you decline. Let me know how you feel.

The photos are from Lady Laura. She's a domme, as you can tell, and she'll be a business partner. She knows what she's doing and you'll be working with her to learn more about the process.

The password is: myenvy


ps For some reason, I have a sneaking suspicion about you. The good kind. I'm certain we'll be working together for the foreseeable future. Let's see if my instincts are right this time.

ps again. Don't forget that the pictures are secret.

There was a link to a private account and she entered the password to access the small library of pictures. At first glance, the sex acts were as expected. Domination and submission. Everything seemed like it was within the wheelhouse of kinky sex. Bondage, whips, chains, and all sorts of gear that Jenny had never seen before were pictured, along with images of their practical use. There were also pictures of the "basics," such as traditional sex and oral sex mixed with a hefty dose of nudity.

The hardcore elements didn't bother her at all. Frankly, like many women in this day and age, Jenny looked at porn on a semi-regular basis; she enjoyed erotic stories, porn clips, and sex pictures.

Two things were surprising about this particular set of images: First, the pictures were taken in classy places like office buildings, studios, and nice homes. Second, these were normal everyday people. They certainly didn't look like glamour models, who were young and eerily thin. Nor did they appear to be porn stars. Rather, this group of people looked like they worked corporate or middle class jobs. That's what really drew Jenny's interest.

Sexually speaking, she found the pictures to be extremely arousing. She could feel dampness permeating her underwear and knew she'd masturbate before going to sleep that night. Professionally, it seemed like an interesting challenge. She loved the allure of helping to create something that would bring great sexual satisfaction to people. If everything went well, this would be her contribution to the world of pleasure.

But in order to explore this endeavor, she knew she needed someone on her side. An ally. Someone who'd know what to do.

After sending Dave a quick reply email, Jenny picked up her phone and called a friend, taking this situation to a whole new level.


For the past two years, Jenny had relied on Cassandra for occasional paralegal assistance.

Cassandra was a research wiz and a great legal writer. She worked freelance, going from job to job, doing work in her living room for small time lawyers in the city. They got along great and quickly became friends. More importantly, Cassandra was one of those free-spirited millennials who embraced the casual nature of sex. To her, sex was like breathing, in that it was healthy and should be done often.

They met for coffee and got down to business after they found a bench in the park.

"So you've never been tied up?" Cassandra asked.

Jenny shook her head. "Nope."



"Penetrated by two guys at once?"

Jenny hid the fact that she was getting irritated. "I'm not fucking anyone. So my experience on the matter is irrelevant."

"Fair enough. So, how can I be of assistance to you, boss?"

There was an air of excitement in the paralegal's voice and a gleam in her eyes. Jenny knew she had chosen the right girl for the job.

"Do I have to spell it out for you?"

Cassandra gave an amused nod. "Yep."

"Can you come with me? It would be really awkward for me to go to a place like that alone, especially with... whatever the hell they're doing. I'd be well outside my comfort level and out of my depth."

"Are you regretting this before you've even started?"

"Not at all," Jenny replied. "I do enjoy challenges. It's interesting work and it should pay well."

"Then why are you so afraid?" the paralegal asked with a wry smile. "It's just sex."

"I know, but this swings a bit more on the perverse side."

"Maybe that's a good thing for you."

Jenny raised an eyebrow. "You think so?"

"A change of pace might be what you need. When was the last time you even went on a date?"

They gave each other the kind of glares that were reserved for good friends.

"I'm paying you for legal research, not advice on my sex life."

"In this case, wouldn't it be the same thing?" Cassandra said teasingly.

Jenny shrugged. "Touche. While we're on the subject, I'm assuming you've done this sort of thing before. You seem very comfortable talking about this."

"Yeah, I have some experience with the subject matter. Nothing too extreme though. Flogging, shibari, and I love being spanked. I've even smacked my ex-boyfriend with a belt after he fell asleep in the middle of a 69 while I was eating a fruit roll up off his cock."


Cassandra laughed. "To be fair, he was being overworked at his job. Otherwise he'd never fall asleep while I was... well... you get the idea."

"Good to know that I have someone like you to guide me during the research phase of this project."

"Again, I'm not a pro. I don't think I've come close to some of the things we're about to see. Assuming, of course, that what we're about to see is as graphic as you say it is."

Jenny took a big gulp of the cooled coffee. "Trust me, it's graphic and hardcore. Nothing dangerous. Nothing extreme. But definitely on the far end of the pornographic spectrum."

"I'll be the judge of that," the paralegal replied with a near evil grin.

"Then it's official. I'll let Dave know that I'm accepting the job."

"What happens after that?"

Jenny paused a moment. "After I give Dave a confirmation indicating my intent to move forward, we'll meet with a domme, who'll be the co-owner of the new company.."


"Lady Laura is her name. Apparently she's a sweetheart with a knack for doling out mental and physical punishments."

"Sexy. I like her already."

Jenny quickly thought of all those hardcore bondage pictures she had browsed the night before, and wondered if Cassandra was truly ready for this.

"So you're sure you want to come with me? I'll make it clear that you're assisting me in a work related manner."

Cassandra nodded. "Positive. It sounds like fun."

"Okay, well, don't say I didn't warn you."

"You're making this sound so ominous. It's not like you're heading into a warzone. It's a legal job. Simple as that."

Once again, Jenny's mind flashed to the images of very rough sex.

"Have you ever seen this sort of stuff online?" Jenny asked. "Double and triple penetration involving participants who are bound?"

"Are we walking into an orgy?"

"That's the thing, I don't know. We're meeting with Lady Laura and we'll see what happens. Are you still interested?"

"Stop asking me. Yes, I'm sure. It's a beautiful day and let's enjoy it, along with our coffee. A little sex doesn't hurt... although sometimes it's better if it does."

More images flashed in Jenny's mind. Surprisingly, it was the image of a bottom, beet red from a recent spanking, that was at the forefront of her mind.


After Jenny had reached an agreement with Dave, the pieces quickly fell into place over the next several days. In the course of Jenny's short legal life, things rarely worked out this seamlessly. It was either a bad omen or good luck.

While waiting, she spent an inordinate amount of time masturbating. With all of these recent conversations about sex-- kinky sex at that --her appetite grew ferociously. She soon found herself spending spare time in the library of explicit images. Hardcore bondage pictures seemed to have the most effect on her sexual appetite. Her clitoris and pussy screamed for attention while she perused the images. Appropriately, she stroked and prodded herself to completion.

A few days later, Dave informed Jenny that Lady Laura would be expecting her call. Then, Jenny passed along the contact information to Cassandra, who made the overture.

Now, it was Jenny's turn to make a call. It was something she had put off for a while. In the meantime, she spent the day in mediation with one of her clients who had a land dispute with a neighbor. It was worked out, but not before she had spent several hours sitting. During some of the downtime that day, she found herself thinking wistfully about images of naked men and women who were engaged in highly lewd activities.

After dinner, Jenny found herself in front of her computer with her legs crossed and a foot in the air. She stared at the phone number on the screen. Dealing with Dave was easy; they were practically friends at this point. But, calling a Lady? A domme? This was uncharted territory.

Finally, she picked up her phone and dialed the number. Initially, they made small talk and it seemed true that Lady Laura was, indeed, a sweetheart.

"I've already spoken to your paralegal, Cassandra," the domme said. "She seems sweet."

"She is."

"Do you make her kneel between your legs while you work in the office? You know, office pleasure?"

Jenny tensed. "No, it's not like that. I keep work separate from my personal life."

"I'm only joking. I can tell you're nervous talking to me."

"Oh, good," Jenny said with a playful sigh. "I'm sure you have a lot of experience understanding different types of people."

"Let's just say that I've done this for a very long time. I know to read tell-tale signs of discomfort. And, I'm also good at recognizing signs of pleasure. Often times, one can lead to the other, and that's where things get interesting. It's all part of my job. At the end of the day, I'll do whatever it takes to push people to their own points of maximal satisfaction. I'm in the business of providing pleasure, and there are many different roads that lead to that outcome."

"Well, I'm in the legal business and I try to give my clients a different type of happy ending. How ironic that our paths have crossed in a professional setting."

The domme laughed. "Life is strange. Like the saying goes; opposites attract."

"I'm confident that it'll be the case. Can you tell me about yourself? I'm interested in you."

"Professionally or personally?"

"Both," Jenny replied.

For the next few minutes, they talked about their backgrounds. Surprisingly, Laura was a former Wall Street stockbroker. She made decent money and had a successful career. But, it was a job for which Laura lacked passion, as a result she found it emotionally unfulfilling.

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