Meet Kailani - Homeless Prostitute

TW - Potential discussions of sexual content including prostitution and forced, coerced, and violent scenes that may depict rape (with screenshots of The Sims 4 with mods and CC). (childhood trauma and mistreatment may also be discussed in the form of neglect, abuse, and molestation for backstory purposes only with no explicit details)

***This is a full gameplay of a homeless challenge that I am doing with a bit of a twist. There will likely be some rules I won't follow but for the most part I am not cheating in game unless something gets stuck or in dire circumstances. I am also mostly letting my character's whims and mood guide her. The stories you are reading are not just made up because I wanted them to go that way, I let the game and my sim do their thing and then created the story around it. Much of this is more than I could have imagined and has been a surprise for me. It's honestly made my game time so much more fun. There are times I will hope it will go one way and it will, and other times I will be surprised at the turn of events but never disappointed. I have been writing these for a while now and just now posting them publicly so you will most likely get content in large quantities when I can upload them until I am caught up.***

Kailani woke up famished. She discovered a cooler next to the grill with some meat inside. She is glad to have something fresh to cook and glad to have met Geoffrey, even if he is a bit of a sadist. Kailani eats her meal and counts up her earnings. With the money she already had she is now at $2445! What a night! She can be fucked and withheld from her orgasm anytime for that kind of money!

She flashes back to different parts of their encounter. She is flushed with desire again. Does she like what happened? She felt so frustrated at times that he would not allow her to come but it made her desire it so much more. Was that his game? He’s wealthy and he's paying her, why does he need a game? Would she still feel this way if Mele didn’t help her relieve that burning desire at the end?

Mele, so soft. Mmm.. Mele was there the whole time, hands firmly grasping and caressing, positioning and rubbing. Mele was what Kailani had heard of as "the fluffer" or at least that is what it seemed to be and she was good at it. Kailani wondered what it would be like to be with Mele without Geoffrey there. All of a sudden she had a strong desire to taste her. 

Kailani was getting aroused again and she needed to get a shower. She was about to head to a gym when she gets a call from Roy. He wants a “date”. Kailani knows she needs to shower but she doesn’t want to give up this opportunity. Their first encounter was so great.

She met him at Discothèque Pan Europa and they flirt a bit before heading inside.

They headed straight to the bathroom which seemed to be Roy’s favorite place to do the deed. Although this time there was no foreplay or consideration of Kailani's needs. Roy went straight into anal play.

Not super comfortable as Roy didn't bother with lube. She did her best to put her mind elsewhere so that she could weather the pain. Sadly, with Roy's lack of concern for her, she was once again realizing that the world really was shit, and the moment they had the first time may have been just a fluke.

Roy began to choke her. Kailani, in shock, turned around to look at him and saw there was no anger or malice in his face. Instead it was just that deep desire. Kailani had a difficult time not feeling the same desire when she looked into his face. It was so plainly written there. Besides, Roy wasn’t hurting her. His grip was firm but, after her initial shock and realizing she could turn her head to look at him, she realized it was also almost part of the excitement.

As Roy started to climax, so did Kailani and the explosion was pure bliss!

Roy paid Kailani $1232 for their "date" but Kailani was not ready to end it so soon. She knew that the paid portion was over, but she decided she wanted to spend just a little more time together.

After freshening up she guided him to a couch where they sat and talked for a few minutes naked. Kailani couldn't help but look down at his stiffening cock. When she looked up at his face he was smirking at her. She climbed onto the couch and straddled him. After quickly putting a condom on Kailani eased herself on top of him, mounting him fully.

This time their experience was more of a mix between the two. The gentle, intimate touch like the first time with the deep penetrating force from earlier.

While Kailani knew that she would not be paid for this excursion, she didn’t care. She loved feeling him inside of her and his arms wrapped around her. He kissed her so deeply she felt drugged. He was strong, gentle, passionate, and while she was in his embrace she could pretend she was something else.

Kailani had a moment where she and Roy looked deeply into each other's eyes. She suddenly felt so vulnerable, yet so safe. She wanted to stay there forever.

What is going on with her? She had never met someone with this power over her. Could he have the same power she has on others and he is now using it on her? This could be dangerous and she needed to get her head on straight. She would, just after, after this. The waves of pleasure lapped over her like the tropical waters in Sulani. She could feel the pulsing in her vagina and she knew she was on the other side of an orgasm so large she could hardly think straight. All she could think of was waves lapping on the sandy beaches and the seagulls mewing. In her daze she realized that Roy had said something before he left but she was too entranced to pay attention to what he said let alone respond.