***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 met Roy for their "date" on the strip of Del Sol Valley. It was a warm evening and the area was all lit up and looked so glamorous. Roy jokingly dared Kailani to get naked in the middle of town. Kailani didn't have an issue with nudity but was not sure what security was like around there. There were a lot of high profile people in that neighborhood.

 

But Kailani was also never afraid to take a dare and figured she was in a great mood so why not. She noticed how much more relaxed Roy started to become as they were more playful with each other, well everything relaxed except what was between his legs. That she visibly saw stiffen.

 

Roy dared her to sneak past paparazzi and climb onto the balcony of Studio PBP, the lounge that was exclusive for the uber rich and famous. Again, Kailani took that dare and raised him one. They climbed up and Kailani dared him to strip naked with her. He did quicker than Kailani imagined was humanly possible. As they peered into the window at all of the famous people inside, Roy lifted Kailani into his arms and eased himself inside of her. Both feeling the high of knowing that they could be found and arrested for trespassing, it got them even more excited.

 

Kailani kissed Roy hard and Roy, in return, kissed her back. Their fluids mixing on many levels and their passions igniting. Roy came deep inside of her, Kailani pushing herself onto him harder as he did. When they were finished there was an awkward pause.

 

“So, um,” Roy started.

 

Kailani put a finger over his mouth and pressed her body against his. “Don’t.” she whispered, and nibbled his ear.

 

She could feel the slight stirring of his cock coming to life again.

 

“Oh Kailani,” he moaned.

 

She pulled back and looked at him, holding his face with both of her hands. “Please stop overthinking this, you will ruin it. I love our time together but I need it to be uncomplicated. You understand that, right?” He nodded.

 

Kailani dropped down on her knees and began licking Roy’s half erect cock which had the mingled taste of both his and her cum.

 

“Mmm…” she murmured. His head shot back in ecstasy as Kailani began sucking him wildly. Before long he was coming again.

 

When Kailani finished she got up and looked at him again. Roy said nothing. She leaned her body against his and kissed him gently, he returning the kiss in kind.

 

He paid her, put his clothes back on, saying nothing and descended the railing turning the corner and out of sight before Kailani decided her next move.

 

All of a sudden her phone rang and she realized she did not turn her ringer off. People from the door heard it and looked up to see her there naked. She had no time to get dressed now, she had to shimmy down and get out of there.

 

Once down and a safe distance away she answered her phone out of breath. It was Darrel, he wanted her to come over for a “session”. Knowing that she could use a warm place to shower and get a meal she decided to say yes.

 

When Kailani got to Darrel's house she wasn’t greeted by anyone. The doors were just open so she went right in.

 

She showered first, between her time with Roy and running from the doorman naked through Del Sol Valley she was grimy.

 

It was early morning hours so she made herself some breakfast. Kailani figured Darrel could wait.

 

Surprisingly, Darrel came over and had an actual conversation with her as she finished her meal. For once she felt like a human being in his presence.

 

She figured she may as well get the job over with since she had him waiting so long. It started off fairly routine, with a blowjob in the bathroom, which was surprising for Darrel.

 

It seemed that Darrel was just getting a slow start, however, because once he paused and asked Kailani to take his shirt off he became more forceful.

 

Darrel forced Kailani down to her knees.

 

Darrel slapped Kailani with his cock while holding her hands firmly in place.

 

"You like that don't you?" Darrel said in a snide tone.

 

When Kailani didn't answer right away Darrel slapped her hard across the face. Her head snapped back hard and her vision blurred briefly.

 

"You will answer me, you fucking whore. You don't get to ignore me." he said with venom in his voice.

 

"Yes, yes, of course," she said, recovering quickly and looking at him directly in the eyes - something she had learned from the many abusive foster homes she had weathered in her youth. "of course I love it!" she smiled at him sensually, something that she didn't have to fake given her superpower.

 

"Mmm, that's right, lick my rock hard cock! You know you want it" he said.

 

Kailani did as she was told, she supposed this was part of the job, especially for Darrel who seemed to love abusing her. Kailani remembered Bjorn and figured that at least Darrel paid her.

 

Darrel seemed to be feeling great when he finished and told her to leave before his mood was ruined. He handed Kailani her payment and Kailani quickly left the bathroom, glad to be out of there.

 

After her adventure with Roy and her session with Darrel, Kailani was too exhausted to go anywhere, however, and at the risk of Darrel abusing her more, she snuck into his room and fell fast asleep. She was awoken by a phone call from one of her previous clients asking her to meet her at a specific address. Kailani quickly gathered her belongings and left. She was thankful to not be noticed by anyone in the household on her way out.

 

The previous client was Jenna and Kailani was both nervous and intrigued to be invited to her home. Kailani discovered that she had a husband and two young children. To her surprise, Kailani was introduced as a friend. Jenna and Kailani sat and talked for quite some time. Jenna told her how she had always dreamed of becoming a wife and a mother but that she also had a strong attraction to women that had never gone away. 

 

"When I saw you at the gym that day with that other woman, well, something inside of me kind of snapped. I knew I had been harboring those feelings for a long time but I didn't know how deeply they ran. They floored me that day and I, well, I couldn't control my urges any longer." she looked up at Kailani with her face fully flushed.

 

Kailani  smiled at her, she knew that a soft touch was the only way to handle Jenna, "I can imagine how hard that was for you."

 

Jenna looked around to make sure that her kids and husband weren't within earshot, "God, you're so sexy. I've been thinking about you so much lately. I can still taste you. I know it's not the most comfortable place, but would you come into the bathroom with me?"

 

Kailani agreed to her request.

 

Jenna pulled Kailani into the bathroom where they spent some intimate time together. It was actually just the room for the toilet and it was so small.

 

Jenna whispered, "We must be very quiet. I cannot destroy my family over this but I cannot deny my needs either." Kailani nodded but said nothing. Jenna kissed her deeply.

 

Jenna was prepared for this encounter and had stashed a double ended dildo behind some linens in the cabinet. They rode it together with Jenna biting her lip for want of making noise that was literally at her throat with waves of pleasure. Kailani figured she had much more practice staying quiet with all of the foster homes she lived in where she would have older foster kids, foster parents, aunts, uncles, even grandparents come into her room at night to try to take advantage of her. She became a real pro. So yeah, Kailani knew how to keep quiet.

 

Under the guise of being a friend, Kailani decided to act out how she thought the role would be played and made herself comfortable. She went into the kitchen and made something to eat. Typically when at a client's house she would avoid talking with other people there unless they spoke to her. Actually, she would try to avoid them altogether. At Jenna's, that seemed like it would have been the rude thing to do. She was a bit out of her comfort zone, since she had never really had a friend before. So she had to go off all of the sitcoms and movies she had watched which, she was sad to say, wasn't very many.

 

She sat down to eat and chatted with Jenna's family. At first she didn't quite understand what seemed off about the interaction and then it dawned on her, they were treating her like a friend of the family not a pariah of society like she was used to. They all seemed pretty great. Jenna's husband asked a lot of questions about where she grew up and about her background that she wasn't all that comfortable with but Kailani could tell that it was just out of curiosity and not because he was judging her harshly.

 

When Kailani announced that she needed to head out Jenna offered to walk her out. Jenna hugged her goodbye and discreetly paid her for her time. 

 

"Here's some extra for being so kind to my family. I'm sure that was so boring for you but I really appreciate that you kept up appearances." Jenna said with a bit of an embarrassed smile.

 

"Are you kidding? I don't need to be paid extra for that, although I will take it," Kailani smirked. "I enjoyed every minute with them. Your family is great and I can see how amazing being your friend would be." 

 

Jenna blushed again. "I want to kiss you but I am worried they are looking out the window. So I am just going to imagine that we are kissing instead. Thank you, I will be in touch."

 

Kailani was feeling pretty good after her visit with Jenna, almost like she had a real friend and wasn't a despised person in the community. She decided to dress up a bit and head to one of the fancier spots at Oasis Springs.

 

She found the place was pretty slow when she got there so she ordered a drink and waited for the crowd to arrive.

 

An older man named Dennis Kim approached her and introduced himself. Kailani wasn’t sure what to expect when he asked for her services. She used to expect the worst from older men in general but has had some somewhat positive experiences that have replaced what she thought she knew. She decided to see what happened.

 

He asked her for a blow job, in the middle of the club. Brazen for an older man but Kailani would oblige him.

 

As more people came in it seemed that some were not okay with the public display and Kailani was sensing more and more that she was worsening her reputation.

 

Mele seemed to suddenly recognize her in the position she was in. It was apparent that her memory of her was attached to the sexual encounter they had more than anything else. Kailani wished she could take some time to talk to her but she had her mouth full at that moment.

 

Mr. Kim payed her and Kailani is relieved to be finished. While she is fine with public nudity the eyes on her for that public act was another thing and the pressure felt different this time. She looked around the room, hoping to find Mele, but it seemed she had already left.