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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 feeling a little foggy headed and it took quite some time for the memories of the night before to come back to her. She checked her phone and found messages from Bjorn which made them flood back quickly. She also noted that today was the day most single people despise but that she had been looking forward to. Kailani believed that a day that was manufactured to sell love would surely bring lonely people her way. So she decided to try to push away thoughts about yesterday and instead focus on the day ahead. She showered and went to workout before looking for some lonely hearts. Having barely been at the treadmill for a half hour, Kailani was approached by Roy. He was not someone she had expected to see but he was a sight for sore eyes.



Kailani jumps off the treadmill and into Roy’s arms. He seemed a little surprised but did not miss a beat. I guess it would be a little weird for your paid lover to kiss you so intimately and once Kailani realized the look on his face was confusion she stepped away to try to be more formal.



Kailani, trying to recover from her indiscretion, decided to ask Roy if she can provide him sexual services. Roy was all in. Kailani was glad that they had a "working" relationship like that, not like Bjorn who got offended by it. Roy walked Kailani to a secluded place.



Kailani learned something new about Roy that day. She learned that he had a thing for feet but that he was embarrassed about it. It took him that long to even ask her and he wanted to make sure they were in a place no one would see. While Kailani did not have that particular kink she was no one to judge and she had no problem going along with it. She would go along with a lot of things for the right price, and honestly, at this point, she would go along with a lot of things just because it was Roy.



Kailani was happy that Roy felt comfortable enough to ask her to do this with him. She felt that it showed progress in their relationship or whatever they had. After he came, Roy paid her, kissed her and told her to “Go get em!” slapping her on the ass as he walked away.


For a brief moment Kailani imagined being in a relationship with Roy and him saying that to her when she went off to “work”. She almost laughed out loud at the absurdity of it but deep in her heart she longed for just that, someone who understood her nature and was okay with who she was and what she did. Hell, maybe even someone who loved to watch or participate from time to time would be amazing if she was writing out a wish list. But alas, this is reality not some fantasy world, and she needed to get her head back in the game.



Kailani traveled to yet another gym and ran into young (okay, around her age), shy, and proper Kiyoshi. She has seen him looking at her from the corner of his eye before and then blushing once she caught him. He followed her onto the treadmill and smiled at her sheepishly before turning and walking away.


Kailani decided to follow him and see if it led to anything. Staying several paces behind him, Kailani watched as he went into the changing room. She waited a few minutes before going in and found young, innocent Kiyoshi standing there naked near the lockers. He was holding a towel and seemed to be pondering if he should cover himself with it. Kailani walked up behind him and stopped a couple of feet away.


“Hey there,” she said in a gentle whisper.


In some ways she felt like she was trying not to spook a wild animal. Kiyoshi turned around slowly covering his groin with the towel draping from his hand and blushing once again. He could not make eye contact with her and just stared downward. Kailani wondered if he was staring into nothing or actually looking at her body.


“It seemed like you might want to talk to me back there but then you just left.” she said, taking a step closer. Kiyoshi seemed to brace himself. He squared his shoulders and forced himself to make eye contact.


When he spoke it was deeper than Kailani imagined his voice to be. “I heard you can do things. Things that may seem weird or…”


His bravado was all of a sudden lost and his body went limp with what appeared to be self-defeat. He looked down at the floor and started to turn away. Kailani reached out for his hand that was not holding the towel.


“Hey,” she said gently and when he didn’t respond she took her other hand and gently tipped his chin up so that he was once again looking at her, “hey, what would you like me to do? As long as you can pay me I will do it.”


Kiyoshi’s head jerked from her hand in surprise. “You don’t need to hear what it is first?” he stammered.


“Is it something that will hurt me?” Kailani asked.


Kiyoshi for a moment had a look of offense on his face. “Of course not, but…” and then he trailed off again.


Kailani thought this would take forever. "Would you feel better whispering it to me? I will keep anything you say to me or that we do together confidential if you are worried about that, okay?”


“It’s not that really, Well, it’s just that I asked this girl I liked and she told me it was dirty and I was disgusting for asking her. I feel so much shame.”


Kailani knew shame and her heart went out to this poor kid. Kailani squeezed his hand and pulled him close to her.


“Tell me.” she said.


“I like feet,” he breathed heavily in her ear, “a lot. I noticed your feet when you changed your shoes before.”


Kailani could feel Kiyoshi’s penis stiffen as he talked about his forbidden desire. She wasn’t sure why today was a day about feet but she wasn’t about to crush this boy’s dreams again like that girl did. She felt almost obligated to help correct that gigantic error from the universe. Someone with his sensibilities did not need his first, and could have been only, sexual encounter to be filled with so much shame. It would have left a permanent scar on his psyche. Kailani reached down and pulled the towel away. Kiyoshi’s cock was rock hard and bounced when the towel was moved. Kailani touched him. A soft groan left his mouth.


“I think you’re ready. Tell me where you want me.” Kailani said.



Kiyoshi sat Kailani onto the love seat and kneeled next to her. He slowly removed her shoes and then socks. He rubbed her feet gently and kissed them on the heel and the tips of each toe. Kailani noted that with each kiss his erection pulsated. Kiyoshi sat next to Kailani on the love seat and he turned towards her with one leg onto the cushion. He gently moved her onto the loveseat facing him and placed one foot directly on the length of his stiff member. Kailani didn’t need any instruction from there. She started to stroke his cock gently with her foot. Kiyoshi groaned.


“This is better than I thought it would be,” he said quietly.



Soon Kiyoshi felt more bold and he gave instructions asking Kailani to take her clothes off as they moved positions. Kailani obliged.



In the middle of their session Nalani walked in on them and, feeling hurt and betrayed, accused Kailani of cheating. It took everything Kailani had not to acknowledge Nalani for Kiyoshi's sake. Nalani knew better, she had been a paying client, just like Kiyoshi and so there was no cheating happening but Kailani did not have the ability to get into that with her at that moment.



Kailani was embarrassed but thankfully Kiyoshi was already climaxing and he was young enough it would not have hindered that much anyway.



Kiyoshi paid her $132. He said he may not have paid at all except she allowed him to do something he had needed for a long time but that he now felt ashamed that he helped her to cheat. Kailani tried to explain that she was not with Nalani but Kiyoshi did not want to hear about it.


“I will be forever grateful to you for your service. I felt so badly about my desires but you helped me see that it was not dirty. It was beautiful and I will be excited to do it again. Perhaps with someone who has better morals. Goodbye.”


Kailani watched as Kiyoshi walked out seemingly walking taller and more confident than he had not too long ago. She will at least try to keep that on her mind when she remembers today because so far there have not been a lot of great experiences otherwise.



Heading back up to the gym, Kailani wondered if she should even be around others right now. She was an extrovert and typically loved being around people but today had been kind of shitty and she doesn’t really know if she could handle anymore of it. But exercise is her best refresher and she needed to keep her body fit so the gym is the best place for her. She will just need to focus on her goal of working out.



Of course, it’s difficult to keep focus when you tend to attract people due to your pheromones and it seemed they kick up a gear when you are working out. Go figure! Kailani was minding her own business when she was approached by Tomax. She wasn’t sure if she should go ahead and engage him or brush him off. She decided to go ahead and humor him. Sex was exercise and at least this exercise would get her paid. Well, as long as she didn’t do anything to fuck it up.





Kailani pleasured Tomax with her hands and in return he did the same. It was quick, easy and she got paid accordingly. Sometimes she wished they were all that easy. Kailani was ready for a shower, a meal, and a good night's sleep.


On her way home, however, she realized she was having some intense itching between her legs. Sadly, this was not the first time she has had pubic lice and she knew she needed to stop somewhere and grab the treatment before she went home. She grabbed a few of them, despite how overpriced they were, because she knew she would probably need them again. She had heard that there was something you could do to become immune to them but it was expensive and she didn’t want to spend what little money she had on that right now.


Speaking of, after picking up the treatment she received another call from Bess. She was so hopeful that she was calling to tell her that her investment had paid off and she was giving her a cut of the money but instead Bess gave her this long winded, yet beautifully worded spiel about the next wave and how she just needed a little more time and money. By the end of the call Kailani had made arrangements to get her another $1000. Kailani wasn’t sure if Bess had the same powers she did, but she had something. The thing was, Bess could do it over the phone with her words. That was impressive. One of these days, Kailani is going to meet Bess and Kailani was hoping to turn the tides. Maybe she could make her a regular customer and then it would be a mutual give and take.



By the time Kailani got home it was late and her stomach was so empty it felt like it was trying to eat itself. She remembered the fruitcake left out by the underpass and decided to go try it. It was the worst but it filled the pit in her stomach.



Kailani fell asleep as soon as she hit the cot. She was ready for the day to end and a new, better one to begin already.

Edited by AzzureRain


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