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.***

 

After her research online Kailani took a quick nap on the couch and then went back downstairs. She found that the place was mostly empty but then also realized how early it was. Not even 7 am on a Sunday. Once the cafeteria opened she ordered some french toast and imagined herself as a student. It was a great thought. She was surprised she could be here without having to show a student ID but she figured a paying customer was a paying customer. She understood that business model well.

 

While eating she started chatting with a girl named Julia. She realized after a few minutes that Julia was the girl she played ping pong with the night before. Kailani laughed to herself at her poor memory. She really needed to stop drinking so much. Julia was telling Kailani how she had a test in about an hour and was super stressed about it. She said she needed to get her nervous energy out and then gave Kailani a sideways glance.

 

Kailani smiled and said “I’ve got the time if you have the money.”

 

Julia didn’t miss a beat. “You bet!”

 

They quickly went to the bathroom stall where Kailani fingered Julia vigorously. Julia would guide her by saying “faster” or “circles, circles!” which Kailani found kind of funny but she listened and did her best to follow as she knew she had a deadline and needed to release some pressure. Within 15 minutes Julia was spasming on the ground with her vulva pulsating wildly. Kailani watched it and had the urge to bend over and start licking and sucking on it but because she was not asked to do so nor being paid for that particular sex act, she held herself back.

 

Once Julia composed herself and looked at her watch, “Shit, that was great timing.”

 

She looked at Kailani in a way that only someone who just had a hard orgasm can and then kissed her deeply.

 

Julia then began fingering Kailani and said “I want more.”

 

Kailani obliged and began to rub Julia very gently as she was a bit sensitive now having just come so fiercely.

 

In all, Julia came another three times although none as hard as the first one. Kailani came a fair amount herself as she often would receive pleasure in others pleasure.

 

“I hate leaving. I could literally do this all day - you are so fucking hot. But I need to take that test. Thank you. I feel so much more relaxed. Here’s some money. You deserve much more. Let’s say I owe you, only because I want more of you later, okay?”

 

She started to walk away and then turned to look back before leaving the room, “Fuck! If you aren’t perfect, I don’t know what is. I am going to be fantasizing about you for a while.”

 

Kailani, never having an issue with nudity, was on a bit of a high from her last encounter and didn’t realize that she went back into the cafeteria without her skirt on. She started talking to some guy doing his homework who seemed to be deep in thought.

 

When he finally looked up and realized that she was not wearing her skirt he was a bit shocked. The other woman at the table didn't seem to mind one way or the other.

 

He seemed to quickly recover and made a remark about how Kailani must be really hot for him.

 

It was then that Kailani realized her mistake and she quickly grabbed her skirt out of her bag and pulled them on. Knowing it was Prank Day she played it off that it was just a prank. The guy was not impressed. He gave her a look of disgust and got up and walked away. Kailani didn't know why she didn't go along with his idea. It could have gotten her another client. She just felt embarrassed and reacted quickly to it. Oh, well. It was too late to fix that mess. Some random guy was offended by her "prank". She would live.

 

Kailani was about to leave, feeling as though she had worn out her welcome, when she heard her name being called by a familiar voice.

 

She turned to find Mana there smiling at her. “You’re back!” Mana said.

 

“Well actually,” Kailani started to say she had never left but Mana didn’t give her the opportunity to finish her thought.

 

“Oh God, I have missed you! Do you have time? I need your services so badly!”

 

Kailani said she did have time and followed Mana into the bathrooms.

 

Kailani wondered if Mana would allow Kailani to touch her intimately this time. Once they got into a stall she was surprised to discover that Mana did allow Kailani's touch but only with her feet.

 

Kailani used her big toe to penetrate Mana and rub her clit into an orgasm. Mana convulsed on the ground in nearly the same spot that Julia did not too long ago.

 

Mana got up and walked out without putting her clothes on. Kailani wondered if she had ever had an orgasm before because she almost looked stunned. Kailani didn’t even realize she hadn’t been paid until she was long gone.

 

Kailani got another call from Bess asking for yet another $1000 and of course she gave it to her. She really hoped this wasn’t a scam. She was banking on this payout helping her get to her independent wealth one day.

 

As Kailani was freshening up at the sink, a person she thought looked familiar but could not figure out how, stopped to look her over. He acted very secretively.

 

“You,” he said. “Do you know who I am?”

 

And then it hit her, it was his voice that made him recognizable. Standing in front of her was a celebrity - Izzy Fabulous! She loved his music!

 

“Yes.” She said confidently.

 

“Good. I don’t associate with people who aren’t already aware of me. It’s too much work.” he said. “You seem like someone I would like to know.” he said in a sly voice, emphasizing the word ‘know’. “And when I say ‘know’, I mean know intimately. I can, of course, pay you. You look like you may have expensive clientele. Do we run in the same circles?”

 

Kailani grins and leans towards him, touching his arm slightly, running her fingers down to his wrist, “I don’t kiss and tell.”

 

“That is the answer I was looking for,” he said and then led her to a sitting area in another room.

 

Kailani was excited to have a celebrity who might become a regular. This was something she wanted to make sure went well. She focused on her task at hand. After undressing, she followed Izzy's instructions and straddled one leg while stroking him. 

 

Kailani ground her pubis into Izzy’s leg while she continued to stroke his cock. Izzy would make comments on how hot they both were and what a hot power couple they would be with the paparazzi following them around. Kailani focused on her task and how amazing it felt on his well toned thigh.

 

Kailani discovered that Izzy got off on the fantasies that he derives by speaking them out loud. As they went on with their session his scenarios became more and more amped up as if he needed more to help him come.

 

Izzy began to talk about things darker like keeping Kailani in a room tucked away for only his eyes and pleasures. He would talk about his fantasies around tying her up and having his way with her while she struggled to get free - while she begged to get away. He closed his eyes and Kailani could tell that he was envisioning it. He then said how he would charge people to come in and have their way with her. Sometimes a roomful at a time. She would be a slave that was there for his desires.

 

As he described men lining up to perform various acts with her he began to come. Kailani knows that fantasies are not always what we really want and she decides to set aside what she has heard tonight in the hopes that Izzy Fabulous had no intention of kidnapping her and holding her in some kind of sex dungeon. Izzy paid Kailani well for her discretion and left without an explanation or apology. Not that she really thought that she would get one anyway.

 

Kailani, feeling quite confident despite that last encounter, heads to the gym for a shower. She has had a busy day already and it's only 5 pm. If she can quickly clean up she can head somewhere to eat and then maybe get some sleep. Her preference would be inside somewhere but it's getting warmer out so it won’t be too bad.

 

Kailani, while extremely tired, was still feeling the high of today. She ordered fish and chips from the bar and then decided to go sit down and watch some television to unwind, a luxury she was not very used to.

 

Kailani liked this little bar in Oasis Springs. They always played her favorite music and there were places that she could just relax and unwind as well.

 

Not long after she finished eating, Nancy Landgrabb sat down next to her. She was feeling a little nervous about any interaction that might happen until she realized that there wasn’t going to be any. Nancy was just there doing what Kailani was doing, relaxing and watching a bit of TV.

 

Just when Kailani’s guard was down, however, Bjorn walked in and sat down. He looked right at her and smiled. Kailani was nervous again.

 

Bjorn’s voice had a phoniness in it that she imagined was normal for people who were from middle/upper class homes, “Hey Kailani, it’s so good to see you. Listen, about our business transaction the other day,” he paused and made a sideways glance at Nancy, “I think maybe I was a bit hasty about the quality of your work and would like to try working with you again. Do you have any time to discuss it right now?”

 

Bjorn gestured towards the bathrooms and Kailani, also not wanting to cause a scene nodded in affirmation and got up to walk over with him. Bjorn stopped her in the small room before the bathrooms by grabbing her waist. “God, you look delicious. I will give you one more shot to make this right but your payment is your reputation and my review,” he said slyly licking his lips.

 

Kailani felt a shiver down her spine. She somehow sensed that saying no now could mean serious consequences as she saw the look in his eyes and felt deeply the loathing within. Yet underneath that loathing was pure lust. Kailani couldn’t prove it, but Bjorn was capable of some pretty dark things. She would not deny him this and perhaps would not deny him anything in the future either. Until she made enough money to afford security of her own, she would have to allow him to have his way with her at whatever cost.

 

Thankfully the cost for tonight was Kailani pleasuring him with her feet that he relished for much longer than he needed to. She was sure that he could see the exhaustion on her face and maybe knowing that she was close to crashing made it more enjoyable for him. He knew how to make his erection last and how to hold off his ejeculation. He did it like a pro over and over again - nearly coming and then having her slow her pace so that he would not so that he could get to the heightened state again just to start over again. It was maddening.

 

Finally, when he came it was all over her feet and lower legs but Kailani didn’t even notice. Bjorn pulled her up to her a standing position and she was practically asleep on her feet. Somehow she needed to make it back home to her bed. If he had said anything to her she did not remember.

 

What Kailani did remember, however, was the look of satisfaction on Bjorn’s face, although it wasn’t just the look of someone who was recently in the throes of passion and had a wild orgasm. No, this was the look of a person who enjoyed the misery of others and, to Kailani’s misfortune, Bjorn had set sight on it being hers for the time being.

 

Kailani took a few steps and was made painfully aware that she would not be able to make it back to her place. She crashed onto the couch nearby and slept for a couple of hours not even bothering to put her clothes back on.

 

Somehow she ended up back in her cot and fast asleep. She wasn’t even sure how. Had someone found her at the bar and taken her home? Did she make it there herself? Was someone called to escort her home? She may never know.