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.***

 

When Kailani awoke she was sore and a little disoriented. It took her a few moments for the memories of the night before to come back to her but when they did they came back in a wave of emotions. From desire to embarrassment to distrust and then back to desire again. It was such a strange thing for her because she was usually the one causing desire in others that she did not always have the same feeling and if she started their behavior would usually ruin it. This time was different. This time the other person didn’t just care about their own needs. Okay, so he got off on her getting off but isn’t that how it should be? All she has ever seen are people out to satisfy their own needs above all else and forget the other person or people involved. In fact, many times they get off on the other person not being satisfied or being uncomfortable. Kailani didn’t claim to understand people. People were cruel.

 

Despite their cruelty Kailani craved being around others. So after freshening up a bit she headed to the Salty Paws Saloon. The place was so crowded and she discovered that she was a little nervous about getting a new client. As much as she wanted to put Roy’s behavior in an outlier category and forget about it, there was a part of her that hoped she would find more like him here.

 

Kailani was approached by an older woman who was at the saloon because a celebrity was also in there. She was a fan but seemed to all of a sudden lose focus on her original obsession to solicit Kailani. Rather shy, Francine chose to chat awkwardly rather than make a move. Kailani, not sure how to feel about all of the cameras being around, tried to get Francine to a more private area to see if that would help her be more brave. 

 

Kailani was able to coax Francine upstairs to the bathrooms where it was more quiet. Despite several attempts on Kailani’s part to engage with Francine, Francine just couldn’t commit to her obvious desires. Her shyness outweighed everything else. Feeling a little let down and pretty tired from the efforts of sweet coercion, Kailani decided to cut her losses and head home.

 

On her way out the door she is stopped by this cute little pixie type who instantly gets giddy at the site of Kailani. The girl introduces herself as Miko Ojo, an up-and-coming social media star. She gave Kailani a pick up line only a gamer would understand and then snorted at her own wit. Kailani found this kind of charming. Miko noticed the celebrity in the saloon and asked if Kailani would be interested in heading someplace else.

 

“This place is already too full of itself,” she said.

 

Kailani agreed to go with Miko hoping it might get her some new customers.

 

They ended up at Club Calico where Miko slipped Kailani something and the rest of the night was a bit of a blur.

 

Kailani woke up on one of the couches and wondered what had happened to her and where was Miko? While there was a lot to be concerned with, the one thing she was happy about was that she was able to sleep inside on a luxury sofa. Although judging by how dark it already was outside she has no idea how long she was actually asleep but she was famished and knew she needed some food. Thankfully she saw her bag with all of her belongings in it, including her money.  She didn't know what she would do if that was all gone. Okay, she knew. She would pick herself up and start back over. It wasn't the first time. But she was glad that she didn't have to.

 

Kailani washed up in the bathroom with the hand soap and made herself as presentable as possible. It wasn't a full shower but it was the best option she had at the moment. She just wished she could get a luxurious bath or something sometime. She reminded herself that this was what this was all about. She needed to keep her eye on the prize. If she could make some more money she could get herself into a better place. She couldn't lose focus of that. She couldn't get distracted with people like Roy or fantasies of being treated well. Those were the things that would veer her from the plan and she needed to stay on task. 

 

The bar at Club Calico is outside and in the cool night it makes it difficult to “work”, well at least difficult for Kailani to work in her outfit. She eats her meal quickly and assesses how much money she has left. She has just over $200 left from the money she got from Roy. She thought she would be rolling in the money by now yet here she is, eating french fries and trying to figure out how to get more people to commit to their desire for her. Why was it so easy for people in Sulani? Was it because they were in their own homes or in more private places? Or was it because they didn't have to pay her? This was going to make it so much more challenging. She can’t build up a clientele without first getting them as clients. What is she supposed to do, go door to door? Kailani decides to change into her skimpy, flirty outfit and sets to work. She hopes she gets someone interested.

 

 

And then someone she knew without a second glance walks up to the bar. Kailani's heart races. It’s Geoffrey Landgrabb, one of the most wealthy, influential men around. If she could get him as a client she could be set for life. What if he took her as his mistress? Oh, she only dares to dream! He’s not the best looking guy but this isn’t about looks. He has wealth and power, both of which Kailani wishes to possess. She flirts with him casually at the bar and he responds just how she had hoped. When he stands up she goes to him and arches her back to push her breasts up and her ass out. She reaches out to him and watches for his reaction. He seems to act a little shy but he doesn’t stop her. She caresses his stomach and then lowers her hand to feel him mound pulsate under her grip.

 

He grins and says, “Mele will handle the transaction.”

 

Kailani isn’t sure what that means until a woman approaches her. Geoffrey walks away and the woman says that she would like to proposition her on Mr. Langrabb’s behalf.

 

“If you agree” she goes on, “I will need to prepare you for him before you can begin and will be involved during the coupling as well. Do you understand?”

 

This was the most formal proposition Kailani had ever heard. She blinked but didn’t miss a beat.

 

“If you both will be participating then I can assume I will be paid accordingly?” Kailani asked.

 

Mele smiled and responded “You will never have to worry about whether Mr. Landgrabb can pay you well, as long as you are able to meet his desires. The fact that he has even chosen you says plenty.”

 

Kailani agrees to the terms and Kailani is surprised to find that she is being guided to a very public part of the building.

 

Mele undresses and handwashes every inch of Kailani. She takes special care in her delicate spots and rubs Kailani until near climax before releasing her.

 

Mele says “she is ready” so abruptly that Kailani jumps a little.

 

Out of a shadow Geoffrey comes out of hiding. He had been watching them and stroking himself, his pants at his ankles.

 

Mele positions Kailani for Geoffrey to mount her. Her hands are weary holding herself up but once he is inside her and propping her up on one side with Mele on the other side of her, she has some stability. He fucks her for what seems like forever. She felt so exposed and somewhat raw from the washing but a part of her was also extremely excited. She could feel her vagina pulsating on his cock. She was so close to orgasming but it seemed that he would bring her just to the edge and the stop.

 

Changing positions, Kailani is sure she will be able to have the orgasm she has been mounting towards. In this position she is face to face with Geoffrey and she can see the desire in his eyes and it is mirrored in hers she is sure. She kisses him deeply while his throbbing cock is deep inside her. Kailani barely notices Mele is even there aside from her hands gently guiding and moving her in ways to assist in Geoffrey’s pleasure. This is not the first time they have done this and Kailani can tell that Mele is enjoying herself as well. Kailani is so close to an orgasm, so incredibly close, she nibbles on Geoffrey’s lip and trembles with desire.

 

Suddenly, Geoffrey thrusts himself out and walks away from her.

 

In shock, Kailani is handed a wad of cash by Mele.

 

“You did very well. Mr. Landgrabb is very pleased and will be in touch. There is a generous tip here. He expects you to improve your wardrobe. Mr. Landgrabb does not associate with wharf rats.” Mele spoke softly in Kailani’s ear stroking one of Kailani’s erect nipples with one hand and then, ever so gently rubbing her index finger onto her clitoris for just a few strokes before Kailani collapsed onto the floor entrenched in such a deep orgasm that she felt the world was spinning.

 

Mele bent down to whisper again “Mr. Landgrabb likes to leave his ladies wanting on their first encounter but I so enjoyed you that I wanted you to feel the deep pleasure of it as well. Let’s keep this our secret, mmkay?”

 

And with that Mele left another wad of money on the ground next to her.

 

Kailani made the walk of shame along the shore of Brindleton Bay, naked and in a daze, in the early fog-filled hours of the morning. Embarrassed, still freshly reeling from her heightened aroused state, and too disoriented to even count the money she just made. She just left it to good faith that they paid her well.

 

 

When she got up to the bench to pass out she noticed a cot there. A note was pinned to it - Sleep well, you will need your rest for our next session. - GL. She doesn’t know how but Geoffrey had found where she was staying. She guessed it wouldn't be too difficult. Brindleton Bay was a pretty small town and Geoffrey was a wealthy man. All he would have to do is ask around and he could easily find out where the mysterious new girl was staying. Kailani didn’t spend too much time contemplating these things. As soon as she tucked herself under the covers of the cot she was fast asleep.