***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.***

 

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)

 

Kailani woke up in the late hours of the evening realizing that she had slept a very long time. She knew her body had to make up for staying up 2 days straight somehow. In her haste, and excitement, she had forgotten to check if she had gotten word back about the scholarships she applied for. When she checked she had received word from all three. She was nervous to open them but she knew she needed to find out.

 

The first one she opened was for the Athletics Scholarship. She was denied. Kailani’s heart sank and she worried that they all would be the same, every single one of them.

 

Reluctantly, she opened the second one, it was for Brindleton Bay Residents. This one she was awarded! For $250 a semester! It wasn’t a lot but it was more than she had just a minute ago. Kailani felt a little better about her odds now.

 

The third one was the Education for All scholarship for people with low income. If she should get any of them, this should be the one.

 

Before reading further, Kailani closed her eyes and just said to herself that everything would be fine no matter the outcome. She opened her eyes and continued reading. She got it! $500! She will now have $750 each semester to go to college! She hoped it would help with living on campus because she could imagine how expensive that might be. Kailani was so excited and pumped with nervous energy that she decided she should try to calm her nerves a little. She tried to do some stretching and then jogged a little but nothing really worked. It was then that it dawned on her. What did she always do before a test or a speech for school to help her calm down and relax? Masturbate of course! So, Kailani did just that.

Kailani stripped down naked and then laid down on her cot, she found a position that was comfortable and tried to imagine her favorite actor in an erotic scene she had thought about a million times. But the image just wouldn't come to her. Using her fingers she expertly rubbed her clitoris, gently at first. 

As she her rubbing intensified her mind drifted to various acts she had performed with different people since arriving inland. Roy, Geoffrey, even inexperienced Kiyoshi all flashed through her mind. Oh, and sweet Jenna and Mana, both so delicate in their own way. Before Kailani knew it she felt her mounting orgasm.

As she came she allowed her body to sputter a bit and she lay there as the waves of ecstasy washed over her.

 

Kailani reflected on the people she had met. She knew she was gaining a bad reputation and that some people despised her but overall her life was better here than it had been in Sulani. She was able to make her own decisions and whether people believed it or not, she wasn't actually in it just for herself. Sure, she needed the money, and sure she wanted to feel secure and safe but who didn't? But she also didn't want to hurt people in the process. If she started doing that intentionally then she would be no different than all of the people that hurt her. Ultimately, she wanted to help people. So what if it was in an unorthodox way? Sex was therapy, right? It always made her feel better. Like this moment, after masturbating, Kailani was calm and felt ready to conquer the world.

 

Kailani went to the mailbox and submitted her application to college. There’s no turning back now, she thought. Even if it takes her 10 years she will earn her degree!

 

Kailani went out to the back of the property she had been staying on and played in the water. It felt good to just relax a bit and she imagined that this may be one of the last times she would be spending here. In a way it made her a little sad. This place has given her shelter and had allowed her to grow and learn so much when she came inland. She may have died if it wasn’t for the shelter of that little greenhouse, the firepit, and that makeshift grill. There were some fond memories here but she could not imagine staying just for the nostalgia of it. Maybe one day she would return and reminisce, after she was rich of course. Maybe she would buy out the property from whoever actually owned it and make it into a safe haven for others. Who knew? Kailani decided to get dressed and go explore another town she had yet to travel to. This one, she heard, was pretty old and well established. The place was called Willow Creek and she had heard there was a nightclub called The Blue Velvet which screamed of blues and jazz legends of long ago.

 

Kailani got there fairly early and had to head to the bathroom to psych herself up. This place was pretty classy and, while she chose to dress in something she thought would be fitting, she felt really out of place. She gave herself a pep talk and went back downstairs to order some food, she was famished.

 

Kailani could see the jazz and blues influences alright. She also saw a grand piano in the main room when she walked in. She was quite impressed with that.

 

Before the place was in full swing there was music playing in the dining hall. Kailani took advantage and danced to her heart's content. She noticed that another patron was doing the same thing. The woman seemed to be stumbling about and had obviously been drinking her meals this morning. Kailani wasn't one to judge, she just hoped she didn't have to clean any puke up off of herself anytime soon.

 

After a bit, Kailani realized that she should probably change her outfit into something that would attract some clientele. Even though there weren't a lot of people there at the moment, Kailani knew there would be soon enough.

 

Kailani, so enamored by the piano, decided to try her hands at it. She used to live in a foster home with a piano like this once and she was so in love with the sound of it but she was never allowed touch it. Of course, Kailani, being the problem child that she was, had been caught touching it on more than one occasion and was punished severely. Kailani still has the scars to prove it. She looked around the room, worried she would be asked to leave, or worse, but no one seemed to notice or care. Kailani played it horribly but with heart and the drunk woman even gave her a tip, a few times.

 

Before long there was a trickle of people coming in the door and just as Kailani had hoped, she was approached by someone. That someone was introduced himself as Dominic Fyres.

 

Dominic, for some reason, was obsessed with her shoes, and wanted her to use them to help him get off.

 

He also enjoyed Kailani rimming him while stroking his cock from behind.

 

All in all, Kailani performed to Dominic's standards, never actually needing to remove her clothing. He got off quickly, paid her and went on his way.

 

After freshening up, Kailani went back to the bar area and realized that the place had become a total hotspot. She spotted Mele who she had hoped to see more intimately since they first encountered each other with Geoffrey. She waved feeling a little pathetic. Mele looked at her for a bit like she was not sure she recognized her.

 

Kailani saw her wave back but also noted that she did not seem to have a hint of recognition in her eyes. Kailani was a little sad, perhaps it was because she had gotten a new wardrobe? Or, perhaps it was because Kailani was just that unforgettable. Kailani shook that thought away. She didn’t need to get herself down, people did that to her enough.

 

Kailani nearly ran into Bjorn and out of a bit of politeness and wanting to not cause a scene, she started to lean in to apologize over the noise of the crowd. She still wasn't sure where she stood with him but she doubted that he all of a sudden just didn't despise her anymore.

 

He was gracious about it and Kailani, feeling like being gracious back, kissed him on the cheek. Bjorn seemed to take it well and Kailani hoped it would help repair some of the damage done. Unbeknownst to Kailani, however, Bjorn’s wife was turning around at the bar right behind them and saw the innocent kiss as something else entirely.

 

She was furious and as Kailani walked away, oblivious to the drama unfolding, Clara set her sights on her husband.

 

Eyewitnesses saw Clara showed her displeasure by slapping him across the face a few times.

 

Meanwhile, Kailani was in the other room where she spotted Geoffrey come in. She waved at him. Almost as instantly as she did she remembered their last encounter and wondered if she should have.

 

She looked away when she realized that he wasn’t acknowledging her. Kailani felt stupid in that moment. She thought to herself why did she need to be a people person? These were her prostitution clients not her besties. Who did she think she was? No one, literally no one, wants to wave and chat up your prostitute when you are out with friends or whatever. She really needs to learn the etiquette. It's no wonder she had a bad reputation. Yet when Kailani's focus was off of him he looked at her longingly.

 

A while later and a few drinks in, Kailani noticed that Geoffrey had sat down at a table alone. She knew she shouldn’t but she went over to the table and sat down to talk to him. “Are we pretending not to know each other?” she said. He looked over at her a little dumbfounded.

 

“I mean,” he paused, “is that something that you think would make sense. Being friendly with your prostitute in public?”

 

“Is that all I am to you?” she countered?

 

“I pay you to please me sexually, so yes. That is how that is defined.” He said a little coldly but she could see something a little sad in his eyes.

 

“Okay, you are right. The customer is always right.” she said, slurring her words a little. Kailani attempted to stand up to leave but before she could get up Geoffrey was already standing.

 

Kailani sat there just watching him walk away. She knew better. She really did. It wasn't like she was trying to chase this man down. What did she want? She really didn't know. She did know that, from a very young age she could sense others emotions, especially if she seemed to have some sort of connection with them. And here she was, with some sort of connection with Geoffrey whether he wanted it or not and she was sensing emotions. They were mixed and she was worried about him but he was right, what could she do about it? She was just his whore. Kailani had to resign herself to the fact that sometimes people could be stubborn and fight against her superpower, even when she was using it to try to help. She figured Geoffrey wasn't used to being the one getting help though and it wasn't like she could exactly explain the help anyway. He would just look at her like she was crazy. So many have.

 

Lost in thought again, when Kailani looked up she found him looking back at her. She looked up when she felt his eyes on her. What kind of game was he playing, she wondered.

 

Kailani, feeling too tired for games, decided to just go out to the back of the nightclub and sleep until morning.

 

When she woke up the nightclub was pretty empty again and she decided to go next door to the gym to shower.

 

She could tell it was going to be a scorcher of a day. She went outside to cook something up on the grill and discovered how beautiful Willow Creek was.

 

She ate with a view of the creek and was reminded of some good times back in Sulani at the beach.

 

Kailani went back into the nightclub and decided to continue to practice playing on the piano. She was so drawn to it. She decided that as soon as she could, she would buy one of these beauties. Even though she was not skilled in playing the piano at all, somehow the women that drink in the morning really love to tip her. This one, seeming to pick up on Kailani's pheromones, also wanted a bit more from her.

 

Her name was Miwa and she had alabaster skin that shimmered like the tales of mermaids Kailani grew up reading.

 

She wore a tiara which didn’t help the ideas running through Kailani’s mind.

 

As she gave pleasure to this woman she wondered what it was that brought her here. Could she be a mermaid trapped inland? Is that why she was drinking in a bar so early. Her skin was so cool to the touch despite the obvious heat outside and their heated interaction. Kailani wanted to ask her but couldn’t. Maybe another time if Miwa ever called again for repeat services. Miwa paid Kailani and quietly left the bathroom.

 

Kailani freshened up before heading back downstairs.

 

Outside she saw Mele again and wanted so badly to talk to her but before she got a chance she is approached by celebrity Brytani Cho who wanted to be serviced immediately. Kailani started to feel the effects of the heat and decided to head into the nightclub right away.

 

Before she gets very far she is propositioned by another woman, Hinata. Kailani tried to explain that she is already working with someone else when Brytani walked up and said “let her join in if she wants.” The woman’s face lit up.

 

“Okay, then, follow me.” Kailani said.

 

Brytani insisted that she be pleased and demanded they do it with explicit instructions. Both Kailani and Hinata obliged her. Brytani got off on both ordering people around and having two women please her. It didn't take her long to have multiple orgasms. Brytani paid well, mostly because she could afford it. Hinata was so enamored by Brytani that she doesn’t even realize that no one has touched her. She seemed to feel the experience was more than she had ever hoped and paid for the service in kind.

 

Kailani ran into Makoa outside of the bathrooms. He seemed nervous about something so she didn’t try to engage him in conversation.

 

Just then she got a call that allowed her to save face.

 

It was Bess again. Kailani groaned a bit.

 

Did Bess need more money? She really didn’t want to give her another $1000. It’s not like she couldn’t, it was more like she shouldn’t. She felt like it might be the principle of the thing now. She went ahead and answered but braced herself to be stern with Bess.

 

This time, however, Bess was talking even more excited than normal. She said something about half the returns and did Kailani want them. Did Kailani want them? Yes, Kailani wanted them! Kailani hung up in shock. It finally happened! She finally got the payout she was hoping for.

 

Wait, did she hear how much? She would need to check her bank account.

 

Standing near the bathrooms in the club, Kailani went onto her phone to look at her bank account. She was now $25,000 richer!

 

$25k!

 

She could buy a house with that! Okay, a dump of a house but it would be a roof and four walls and she wouldn’t have to worry about someone coming by and finding out she was there and kicking her out. She could buy things to put in that house.

 

Okay, it wasn’t a million dollars, yet. But it was a start.

 

Kailani wasn’t ready to spend it yet. At least not on something as expensive as a house. With the money she had already saved up from working she was now at nearly $33k.

 

She was hopeful to be accepted into college and was excited to go live on campus. She wasn’t sure of the cost of that but now knew she could afford it. Things were really looking up. She decided, as difficult as it might be, not to change anything (well except maybe her wardrobe) for now since she knew there were new things just around the corner.

 

Kailani went back home to take an inventory of everything she had and realized that it wasn’t much. She also realized that knowing she had all of this money made it difficult to imagine just hanging out in this trash heap. But why would she buy something if it was going to be so temporary? Maybe she could rent a small apartment instead?

 

Kailani decided to start a fire and sit down for a bit. She enjoyed the heat on her legs and imagined her life somewhere else. How long would it take her to become a millionaire? She wasn’t sure but she was content with the amount of money she had in the bank at that moment. Mid-thought she received a call from Roy, he wanted to hire her for her services and asked to meet in Del Sol Valley where all of the celebrities hung out. Kailani agreed and noted how formal he sounded on the phone. Maybe baring his soul to her like that had changed things. Kailani hoped not.