The sex party has moved to the backyard with Anna on display. This is likely the penultimate chapter of this story. Of note, there are elements of non-consensual sex in this series. I hope my readers enjoy this chapter. Feel free to comment, message, vote, or leave feedback in any way you wish.

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Anna watched as her former husband kissed the young neighbor. Even with cum having spilled on her face, Harry was willing to let his lips meet hers. Once again, Harry being permitted pleasure fueled Anna’s fire. She had long lost count of the number of men who had fucked her. She thought for a few minutes and attempted to come up with an estimate based on the number of men and women at the party, how long she had been servicing them on the air mattress, and that her three holes were filled, or busy, the entire time. As she continued to do the math, she thought about how to further prove to Harry that she was owned… and loved it.

“Master?” Anna asked.

“Yes, slave?” Jacob replied. The task seemed easy, he wondered what it was she might be asking.

“I wish for you to show everyone just how good of a slave I am. I would like to decline to guess,” Anna suggested. The crowd seemed rather excited by this response.

“Hold up everyone,” Jacob yelled, in order to quiet the rowdy crowd. As the evening went on, with more drinks and further fun, the guests seemed to be getting more and more wild. They all knew the rules with Jacob, and Sadie, being in charge. But he also wanted to make sure they stayed in line. “Slave! I gave you an order. What you want doesn’t matter. You are to guess whether you like it or not.”

“Well…” Anna started to speak. She thought for a moment. She had a number on the tip of her tongue but she was quite certain that Jacob wouldn’t take kindly to it. Of course she wished to please him but she also wanted to hurt Harry. In that moment, her need to punish Harry was her primary motivation. “One, Master.”

“One?” Jacob asked. He was shocked by her response. Perhaps appalled was a better way to describe his feelings at that moment. He could not believe that his slave was trying to take control of the game. He knew why, but that wasn’t good enough. Her disobedience in failing to offer a real guess was going to be painful for her. In her time with Jacob, he had inflicted many different types of painful punishments on her body. It was all in the name of molding and training her to be his slave.

“Yes, Master,” Anna added. “I lost count of how many men and women used me. But I do know one man who didn’t and never will again.”

Jacob smirked at that response. He still wasn’t pleased with her guess but he did enjoy her choice of humiliating Harry. Jacob grabbed the whip. It was new. He had specifically purchased it for this evening. It was a single tail snake whip. The snake whip was more flexible than a traditional bull whip. The advantage of it was it was great for targeting one particular area with flicks. The end of the whip was a dragontail, a thicker, wider arrow shape tail that would result in a more intense impact. In this case, Jacob was planning to use the new whip on his slave’s back.

He stepped around behind her. He thought about turning her so that the crowd could see the whip striking in the middle of her shoulder blades over and over. However, Anna’s reaction would be far more pleasurable to the group.

“You will receive 102 hits, slave.” Jacob stated. Anna’s eyes went wide. That was more than she expected. She hoped she could take that amount of pain. She was also proud to have pleased so many guests, although many of them likely came multiple times. She could tell that the crowd was rather excited by that number. One person who wasn’t was Harry. He seemed saddened by that number. Perhaps even embarrassed that his former wife had fucked so many people in the neighborhood.

“Masters and Mistress!” Jacob addressed the crowd as he started to fling the whip, not yet pointing it at Anna’s back. “Now comes the time in tonight’s festivities where our slave is going to suffer for all of our amusement and pleasure! Feel free to touch and play with each other, consensually of course. However, slave may not be touched in a pleasurable way during her punishment. You may slap her face, smack her tits, twist her nipples, spank her pussy, squeeze her clit… I think you all understand. She is just not permitted to feel pleasure right now.”

He raised the whip and brought it forward. The motion was similar to throwing a baseball. It landed with a loud snap against the middle of her back. The first strike caused Anna to scream louder than the snap from the whip. Had it not been for the fact that the whole neighborhood was at the party, Jacob might have had to consider gagging her to prevent anyone from calling the police.

Anna took a few deep breaths. The first hit was intense but also rather surprising. She didn’t know how hard it would be or how the new whip might feel. She needed to calibrate to the level of pain that it provided. She waited. Anna couldn’t see Jacob so she had no idea when the next strike of the whip would be delivered. She wished that she could see or at least have any idea of the cadence of the strikes. However, when the second hit came, she was more easily able to bear the pain.

Sadie was the first to step up to Anna. Although the crowd was more lively, they still seemed to require someone to break the ice. Although, many of the couples were more into fucking each other while watching Anna getting tortured than participating in her punishment. Sadie reached for Anna’s nipples just as another strike was coming to her back. She grabbed both nipples, pinching while twisting and pulling them away from her body.

Anna attempted to resist showing how much it hurt. She looked directly in Sadie’s eyes. Sadie had a sadistic, evil expression staring right back at the slave. Sadie wanted to hear Anna scream. It was a battle of wills, Anna’s ability to take the pain being given to her versus Sadie continuing to increase the intensity. Finally, as the whip struck her back again, Anna cried out. Sadie hesitated for a moment, listening to the sound coming from Anna’s mouth, before finally letting go.

It didn’t take long for others to step up and test Anna’s pain tolerance. Having seen the abuse Jacob and Sadie dispensed on the slave, they were much more willing to try their hand at hurting her.

“Masters,” Sadie announced to the guests. “There is one poor individual here who has only received a load of cum when it fell from the pussy of our slave.”

Harry, Jill, and Jacob all knew what Sadie was referring to. Harry hadn’t cum yet. Every other guest at the party had cum, or at least all of the male guests had, but Jill had yet to feel Harry’s cock orgasm inside of her. As the party was shifting from Anna being a sex toy to Anna being a pain slut, Sadie had the devilish idea that Jill should at least take a single load inside of her.

“That’s right!” Sadie continued. “Jill, this hot, sexy recent college grad, has cum many times herself as Harry was fucking her. But she hasn’t had anyone cum inside her yet.”

Harry turned bright red as everyone learned of this fact. Truthfully, he wanted to. Jill was hot and sexy, just as Sadie described her. Her tight pussy felt amazing around his cock. It was the event of the party that prevented him from achieving orgasm. ‘If only the slave wasn’t the woman he was previously married to, he would certainly be enjoying himself more,’ he thought. That thought alone scared him. Maybe he was just like everyone else at this party. If it wasn’t Anna but some other woman from the neighborhood, would he have been just as eager and willing to fuck that slave?

“Harry,” Sadie addressed him specifically but spoke loud enough for all to hear. “If you don’t fill her with your load in the next ten minutes, then we will find at least one guy here who is man enough to cum in her holes.”

Jill turned to Harry as the crowd started to clamor. She barely knew him but it was his cock, his cum that she wanted. He was only semi-hard when she knelt down on the grass. Until now, Harry had only sampled one of her holes. Despite having focused on studying in college, Jill was aware that she had almost no gag reflex and could throat a cock with ease. With the ten minute challenge given to them both, Jill wasted no time showing off her skills.

As she sucked him deep, Harry watched Anna getting whipped. He saw numerous men, men who had previously fucked her, walk up to her naked, bound body and abuse her. Slapping her large, fake tits, spitting in her face, pinching her nipples, smacking her pussy and clit. Harry watched her pained facial expressions. He heard the crack of the whip hitting against her back. He felt like he was in heaven as Jill took the whole length of his rigid cock inside of her mouth.

Harry put his hand on the back of Jill’s head and arched his head back while cumming inside of her mouth. Sadie checked her watch but was already certain that Harry was well within the ten minutes. Sadie walked away from Harry and Jill, as Jill swallowed all of Harry’s cum. She made her way back towards Anna.

“Well… Harry got to cum,” Sadie whispered to the tortured slave. “I know you didn’t want him to have pleasure. I can see how much you want him to come away from this party in pain. The question is, what might this slave have left in her tonight to accomplish this task?”