This story contains lesbian sex, edging, orgasm denial, bondage, sexual encounters with several people at once, ruined orgasm, and a power imbalance. All characters are 21+ and enthusiastic participants, although irl consent can get messed up by power imbalances. So ofc don't actually fuck your employees and don't read if a boss/employee relationship is disturbing for you.
I appreciate feedback and suggestions! Anything, but especially where you want more details, what you could do without, and how to make the characters more believable. Enjoy--
Throughout all of her teenage and young adult years, Joanna had wanted to get out of her hometown and see more of the world, but she didn't have the means until she met Regina. Joanna had been selling produce at the market when a tall woman with cropped hair and nice muscles pushed through the crowd to her table. Her face and posture were cold, and Joanna didn't expect her to start a conversation, but she did. Joanna was filled with the urge to answer and please the woman. She revealed that she hoped to travel, but had no way to do so.
"I own a ship, and I bet that sort of life will suit you," Regina told her. "Actually, we have room for another woman on board."
Joanna wanted badly to accept, but she had no experience with boats, and told Regina so.
"A girl like you doesn't need experience. I don't need another set of hands working on deck." Regina told her.
"What do you need then?" Joanna asked.
"Someone I can play with." She said, leaning in close. She was certainly forward. "I need a woman to help with my personal desires. The rest of the crew could use someone like that too, and I think that you'd be perfect. I want a young woman I can trust to bring me pleasure during my trips. Someone submissive."
Joanna's breath caught in her throat. Regina extended her hand.
"What do you say, beautiful? If you don't like it, I'll drop you back here."
The compliment caught Joanna off guard. She grabbed Regina's hand and left her produce at the stand.
After a long walk, they arrived at Regina's ship. It was just as impressive and intimidating as its leader. Once Joanna climbed aboard, her eyes immediately went to the flag, lowered and mostly out of sight. That was when she realized that the woman who had swept her off her feet was a pirate.
"If you accept the job, we will provide for all your needs. You will need to wear a uniform at all times. I will be your boss, so you'll refer to me as "ma'am" or "miss". Regina explained.
Joanna nodded, and looked around at the other couple of women in their practical sailing clothes. Instead, Regina handed her an unusual-looking pair of underwear.
"Change into this if you're still interested." Regina ordered.
"Yes miss. Where do I change?" Joanna asked.
"In front of me, now." Regina told her impatiently.
Not wanting to disappoint her, Joanna stripped naked. Regina watched her very closely, her eyes slowly inspecting Joanna's body. Joanna had medium-sized breasts, full hips and thighs, and silky ginger curls between her legs. Regina looked so approving and hungry, and Joanna felt a rush of excitement from her attention. The underwear was soft and nicely made, but it had a strange string of smooth beads that nestled between her folds.
She reached to put her other clothes on over the underwear, but Regina grabbed them.
"Absolutely not." She said sternly. "Follow me."
She walked briskly across the ship and Joanna tried to follow. The moment she took a step, she felt the beads slide up and down her slit, rubbing her clit from every angle. Regina was already at the other side of the ship, and watched with delight as Joanna walked on wobbly legs.
"Do you accept the job?" Regina asked.
"Yes miss. I accept." Joanna told her. It was an easy choice, considering that she was only a few minutes in and didn't want to take off the underwear.
"Good." Regina said, and grabbed a piece of rope from the deck. She tied Joanna's hands behind her back, making her feel even more exposed. Joanna tested them and felt herself becoming more aroused when she couldn't get her arms free, and noticed Regina's eyes on her boobs again.
"We leave in 2 hours" Regina told her. "I want your clit to be so worked up by then that you can't think straight. So you're going to spend the next 2 hours walking slowly around the ship, again and again. If you speed up enough to finish, or pause, you will be disciplined. I will not go easy on you. I like you, but I don't stand for any disobedience on my ship. Of course, you can quit the job at any time, and I'll respect that, although you'll probably be stuck on the ship for a while. I'll be the one giving your orders and I expect you to follow them as long as you're working for me, but I have no interest in coercing you into a job you don't enjoy, so you're allowed to call off the deal at any time, and I'll drop you off where you choose. Does that all make sense to you?"
"Yes, miss. I appreciate that. I want to work for you." Joanna said.
"Good. Then get moving."
Joanna hadn't expected that to be her first task, but she wouldn't disobey Regina. Still, she didn't know how she could possibly get through two hours of that, considering that just walking a few feet had felt like torture. She began to walk slowly around the edge of the ship. The beads rubbed her over and over, and she groaned at the painfully slow motion. She instinctively tried to grab the beads to hold them still, but of course, her hands were tied behind her back. By the third lap around, she was barely able to stand upright. The rubbing between her legs was relentless and unbearable, and all she was allowed to do was to keep walking while Regina watched her, able to give her the relief she needed at any moment, but refusing to do so.
The beads were slick and soaked with her wetness, which just made the friction as they rubbed against her smoother. She couldn't help but move her hips as she walked, as if her body thought that she could get off by grinding against the air. After about 30 minutes of walking, Joanna was shaking and shuddering with every step. Her clit was more swollen than she'd ever seen it, and so sensitive, which only made it all worse. Her whole body begged her to stop walking, to stop teasing it, but she forced herself to continue, feeling the beads slide up and down, over and around her desperate clit.
She could not go on. She looked over at Regina pitifully, hoping to see some mercy on her face, but all she saw was delight. Seeing the gorgeous woman pleased with her state was good too in a way, but as much as it turned her on, it didn't help her situation.