***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)

 

On Kailani's jog she runs into her “great white whale” - Geoffrey Landgrabb. She had imagined that she would have seen him more often but nothing had seemed to come of it. She was still grateful for the cot, clothing, and other gifts he had afforded her since their meeting, however strange it was.

 

Geoffrey noticed her and called her over. “Kailani!” he called out.

 

Kailani was a bit shocked that he even remembered her name. He waved for her to come over.

 

“You are looking quite fit and luscious. Why don’t you go get cleaned up a bit at the gym downtown and change into something more elegant and meet me back here. This is my home, by the way. I would love to show it to you and then have you again.”

 

Kailani was a little surprised by this but agreed to his proposal right away. She quickly jogged back to the gym and got ready.

 

“You made it back.” He said.

 

Kailani nodded, a little out of breath from the effort to get back quickly.

 

“Is this what you consider to be elegant?” He said in an exasperated tone.

 

Kailani was taken back. She had thought that, with him being in khakis and a plaid shirt that this was more than elegant enough in comparison but she thought it would be better to hold her tongue.

 

“Do I need to do everything for you? I guess a whore has no concept of what elegance is! No matter! Those clothes will be off of you soon anyway. It will just be tougher to set the mood.”

 

Kailani reacted instinctively as Geoffrey raised his hand in frustration. Her first thought was that he was about to strike her but then there was no impact. Geoffrey noticed her reaction and his expression changed from one of anger to concern.

 

“I’m not going to hit you, dear God. I don’t know what you have been through in life, and well I guess I should keep that in mind, but I would not harm you.”

 

Kailani’s muscles began to unclench.

 

“May I touch you?” Geoffrey asked her.

 

“Yes, of course.” Kailani said, not realizing until she spoke them how small and weak she sounded.

 

He wrapped his arms around her, hugging her in an embrace that was both comforting and sensual. His fingers traced down her spine until he was cupping her ass with one hand and the other was running fingers through her lush hair. His lips brushed her neck and she could feel the heat of his breath. Shivers shot through her.

 

“I know you don’t know me well,” he kissed her neck, “but I mean only to derive pleasure for the both of us. Just looking at you makes me hunger for you.” he pressed his groin against her and she could feel his stiffness throbbing. It felt as if it was ready to burst out of his pants.

 

Releasing her from the embrace, Geoffrey grazed Kailani’s hand and said, “I need more of you. Follow me inside.” Kailani, without much thought or hesitation did as she was told.

 

Geoffrey’s house was spectacular. Kailani soaked it all in. As they ascended the stairs Kailani saw Geoffrey’s wife, Nancy, watching them. Nancy was pregnant and she looked ready to give birth any day now.

 

“Geoff, honey..” she said in a tone that reminded Kailani of people who were rarely authentic.

 

“Yes, dear heart,” he replied.

 

“Who is this?” She asked.

 

“Nancy, I don’t think you really want to know, do you? What’s our agreement?”

 

Nancy paused and Kailani heard a sniffle and then some gentle sobbing under Nancy’s breath.

 

Geoffrey went on, “Now Nancy, you brought this up so I am going to need you to say it.” Nancy gulped down her tears.

 

“That I can have everything I want as long as you can have whoever you want - but honey - why her - she is so trashy!”

 

Kailani heard the inflection in Nancy’s voice, the bitter judgment. She knew where she stood with this woman and it hurt a lot.

 

Geoffrey, not rebuffed, said plainly, “you are not allowed to question me. Question me one more time and you will have to watch. Do you understand?”

 

Nancy, turning away and in a hushed tone simply said, “I understand.”

 

They went up to the top floor which seemed to be a study with a computer, an easel and lots of places to relax with mood lighting. Geoffrey asked for Kailani to start their time off with her feet pressed firmly to his erection while he looked her over still fully clothed. Kailani noted that while he had told Nancy off he still seemed to be upset by the interaction.

 

Kailani decided to shift positions and provide more stimulation with her mouth. This seemed to get his focus on the task at hand much better.

 

Soon he was pulling her dress off as well as his own clothes and mounting her from behind. Geoffrey was still seemingly deep in thought but at least he was deep in thought while deep inside of her.

 

Pushing her hard into the sofa, he came all over her ass and back. Kailani was pinned there while he finished. Geoffrey seemed to be in a trancelike state with no real connection to Kailani being there other than the act he just performed.

 

Kailani saw the expression on his face afterwards and knew he was still bothered.

 

“Should I leave? Are we done here? Will that make this all better?”

 

“It’s not you. It’s everyone else. Nancy knew what our marriage would be when we were engaged so long ago. It’s written in the prenup, hell it’s even in our vows! But lately she has been acting like this. Like I owe her to stop doing what I have always enjoyed doing. Did you know that she was “trashy” when I met her? She grew up with nothing. The fact that she was just so brazenly talking about you in front of you like you didn’t even matter bothers me. I have given her everything she has desired. We have a teenage son, another child on the way, and all of the money I have made and continue to make is at her disposal. But I am a man with many desires and she has known this about me. I have never made it secret to her - just the public because I am a public figure and that could ruin my business.”

 

Kailani listened to Geoffrey unload his burdens. 

 

“I’m so sorry that you are having to go through all of this. I am also sorry that I misjudged you. I thought because you were rich you must not have any problems.”

 

Geoffrey snickered quietly at that. “I get that my problems are kept more quiet and are not as life threatening but they are still challenging. I love my wife but I am really growing tired of the moral judgements and manipulations to try to get me to change who I am.”

 

“Thank you for staying.” Geoffrey said. “You could have gotten your payment and left but instead you showed that you cared about what was going on with me and stayed to make sure I was okay.”

 

Kailani sat down next to him.

 

“This may have broken my own rule,” he said.

 

“What do you mean?” Kailani asked. “I have a rule of not getting emotionally invested with those I am sleeping with. My emotional connection is and has always been with my wife.”

 

Geoffrey looked at Kailani deeply, Kailani looked at him back.

 

She wasn’t sure about the L word but she did feel for him emotionally. She was worried for him and his situation and wanted things to work out for him.

 

Kailani leaned over and kissed him. They kissed for some time.

 

Geoffrey smiled at her almost sadly, “I would love for you to stay but you must go. I am going to cherish this memory.” With that he paid her and Kailani left.

 

Kailani wasn’t sure if what he said meant that he was saying goodbye for good since he had broken his own rule but she guessed only time will tell.

 

On her way out she received two calls. First was a call from Bess who still did not have her investment for her but only asked for $1 this time. Sure Bess, whatever. Kailani had yet to meet this woman and was really starting to wonder if this “investment” was even legitimate.

 

The second call was from Roy. He was asking Kailani out on a date. This was something that Kailani told herself she needed to have a strict rule against with clients but at the same time she had also broken the rules with him a number of times. Their last intimate encounter was not one that she asked for payment for and there were times before that as well.

 

She decided what the hell, she had been working hard and they were really her own rules anyway. It’s not like something horrible would happen if she didn’t keep to them. She was a smart woman and she knew how to use critical thinking to make rational decisions. This would be one of those times, and this would be one of those rational decisions.

 

It was, right? She thought to herself just a little doubtful.

 

After getting a bit of a nap in and making herself more presentable, Kailani met Roy at the pub in Henford-On-Bagley, somewhere she had yet to visit. It was small and quaint. They kissed and she sensed that he had missed her since this morning.

 

Kailani enjoyed Roy for the most part. It was only until recently that he started to show a jealous side that she felt a little put off by him. She hoped that would fade away if she showed that she was interested in him and maybe even told him how he was the only one she had been seeing outside of getting paid. She did worry about revealing that. Some people go a little crazy when they find out that kind of information. Would Roy become more possessive? She would need to gauge how tonight went.

 

They found a secluded place by the fire and sat down. “I need to talk to you.” Roy said hoarsely.

 

Kailani felt something in the pit of her stomach sink. She looked at him with rapt interest and tried so very hard not to change the expression on her face, not to give way to this feeling that was washing over her.

 

What was the feeling? Was it fear? Anxiety? Worry? A combination of all of them? Who says they need to talk to you and it ever be something good?

 

Kailani was in mid thought when Roy went on, “I know you noticed my anger and jealousy earlier today. It wasn’t my proudest moment and I need to apologize to you.”

 

Kailani looked at him in utter shock. She was being apologized to. Has that ever happened before? Especially for anything like this? She couldn’t remember but she was pretty certain it had not.

 

Roy went on, “It’s just that, well,” he gulped, “I have developed feelings for you and, well not that it makes it right because it doesn’t…” he looked at her then and she swore she could see what he must have looked like as a boy, young and fragile. “I don’t want you to forgive me because you feel bad for me or because I am apologizing. I want to earn it. I fucked up. I knew what you did, fuck I have hired you more than once. I can’t just expect that you stop your job and, and…” he looked down in what appeared to be shame.

 

Kailani was about to speak when he interrupted, “Please, just let me get this out. If I don’t I won’t find the courage to do it again, okay.”

 

Roy had continued to look down the whole time until he asked the question and at that point he glanced up at Kailani to make sure she was okay with it. Kailani nodded yes and Roy continued speaking. “It’s just that, well, sometimes seeing you with other people gets me really turned on but then other times I see you and start thinking about how much better looking they are and how you probably like them better than you like me. I know it’s stupid, you probably don’t even like me at all…” Roy’s voice got gravely and he seemed to have to choke back tears.

 

Kailani reached for his hand cautiously, not sure if he would accept it, he grabbed it hungerly. “I love you Kailani, okay there, I said it. I think about you all the time. You are perfect and I want to be with you all the time and I don’t mean just fucking although I do like fucking you and want to do that as much as possible too. When I am with you I feel like things are just right, you know? I don’t fucking care who’s watching us, you know like that punk Asian kid that was getting his rocks off watching this morning? I didn’t fucking care because being inside of you was like heaven.” 

 

Kailani realized that Roy was now rambling and that anything Kailani said (aside from saying that she loved him and wanted to be with him, which she couldn’t and wasn’t sure she ever could) would help the situation. Instead she decided to just do what she does best and let her body talk for her.

 

Again, she cared deeply for Roy and she knew there was something about him that did make him different but was it love?

 

Kailani wasn’t sure she knew what love was and she wasn’t prepared to say she did to make him happy nor to say she didn’t and ruin the night.

 

Kailani got up onto the couch and hovered over Roy, kissing him deeply. Roy relaxed immediately. She could feel the tension leaving his body as he gave into his urges.

 

Kailani spent time teasing and pleasing him and made the night and their love making (funny thing to call it but she figured it was at least true for one of them) last a while.

 

After they were through it was apparent that Roy was feeling much more himself, which is exactly what Kailani was hoping for and even though she said not one word of affirmation or expression of love for him he seemed satisfied with her.

 

Perhaps he felt that she did express it physically and in that way maybe she just lied to him. She can’t be sure.

 

After getting dressed, Roy drew Kailani into his arms and whispered “You are a goddess and I cannot own or possess a goddess. I understand that now. I am just happy to have moments like this with you. Please forgive me for my arrogance and jealousy. I will continue to do what I can to make up for it. My love for you is deep and vast but I know it cannot contain you. But it will be here for you, always.” He kissed her as deeply as when they first met for the date and then left.

 

Overall Kailani was feeling pretty good about how that went. Roy seemed to understand that she needed to be able to keep doing her job and that he had to keep his emotions in check. Or at least that's how she understood it.

 

Kailani was not quite ready to end the night so she decided to change her clothes and mingle a bit. 

 

Kailani went into the bathroom to freshen up and change into something else. She heard shouting coming from upstairs and went up to investigate. She found celebrity Octavia Moon yelling at someone angrily. Apparently they had asked for an autograph and she was not in the mood. Kailani sat down next to her and asked if everything was alright. Octavia glared at her and was about to start yelling at Kailani next until she caught a whiff of Kailani’s pheromones.

 

Octavia, now seeming to be a little confused, just tipped her head down. Kailani flirted with her a little by telling her how beautiful she was and how she has always been such a stunning actress. Octavia seemed to calm down enough to at least stop yelling. Kailani took that as a sign to head out. She knew better than to try to chat up a celebrity that didn’t want to be bothered for too long, even with her superpower. It could help alter their mood but it wouldn’t help with getting them to talk to her. And if Octavia wasn't into women then it could become an even bigger issue. Flattery could get her only so far but Kailani's goal had been accomplished, Octavia had been subdued.

 

Kailani was feeling a little hungry and decided to head to the bar for some food. Before the food was finished, however, she was approached by this older gentleman. He seemed to be very knowledgeable about the area and chatted with her a bit about its lore and history. He introduced himself as Derek Moody and then made a sly comment about not having had the joy of experiencing an island girl before.

 

“Give an old man the experience of his dreams, would you?” He said with a sly grin.

 

Kailani smirked, leaned towards him and whispered, “I can be yours for a while if the price is right.”

 

Derek chuckled a little, “Well, I’ll be! Two birds for the ole’ bucket list! I’ll meet you out front young lady.”

 

Kailani discovered that Derek was a spry old man. Living in a farming community meant working those farms and staying pretty fit, she imagined. Kailani was held firmly in a position she could only imagine came straight out of the Kama Sutra. She felt her muscles moving and flexing in ways she didn’t even realize they could go. Derek’s cock seemed to be positioned into her at an angle she had never felt before and it was hitting her g-shot over and over again. Derek was not much of a talker but he grunted a lot. Kailani worried that he would drop her but he never did. She was firmly in place and even after multiple orgasms he still was able to hold on tight. Once he finally ejaculated he gently set her down.

 

“You, young lady, are quite the delight. I would go for seconds if my back wasn’t hurting.” He chuckled softly at himself. He pulled some money out of his wallet that was laying in the pants on the ground. Nearing her, he grazed her nipple with his fingertips and looked into her eyes.

 

“Oh, I wish I could have met you when I was your age,” he said with a longing in his voice that Kailani could nearly feel. “Here you go, love. You were worth every penny.”

 

Kailani had never quite felt such endearment towards an older man. Usually they were creepy or rude. She thought she would remember Derek for a while and if he decided to call for a return visit she would be happy to oblige.

 

After a shower and some food, Kailani went home to get some sleep. Other than a brief nap, she had gone another couple of days without sleep and her body was not happy with her. Her wallet, on the other hand, was quite full.