It was now Saturday. Jessie had to wake up a bit earlier that day, as she had to go to work. She was given grocery duty.
The blonde MILF stood there, bagging a younger gentleman's groceries. He was blonde, tan, and had red lips. Somehow, it felt like she had seen this man before. But, she couldn't place her finger on it.
"Alright, sir. Your total is sixty dollars and thirty eight cents." she said.
The man just stood there, looking clueless as to what that meant. He knew it was his total, but it seemed like he went into the store without a valid payment method.
"Cash or credit, Sweetie?" she asked, trying to be patient.
"Uh... Inflation's kind of a bitch so uh... how about I pay you in another way?" he said, dropping some hints.
"Ugh, security!"
Next thing she knew, the tan guy was being escorted out by two security guards. Usually, Jessie would have a smirk on her face. But today felt different. It felt like she was wasting time.
She then clocked out, ending her shift. She went home, so relieved that the day was finally over.
"Finally!" she said, hanging up her work uniform. This new job was stressful, but it paid the bills.
She lit a cigarette, not caring about her attempts at quitting. She's earned this one.
Jessie then got on her phone to check her text messages. She had one from Marlena, saying 'call me whenever, K?.'
"Hmm... I wonder what this is about?" she said, dialing her Brazilian friend.
It took a few rings, but she eventually picked up.
"Hello?" the Brazilian answered.
"Hey, Marlena. I got your text." the blonde MILF replied.
"Ah, yeah. I kinda forgot about that."
"So, what did you wanna talk about?" she asked.
"I wanted to talk about that fake-ass food critic we hung out with last night."
Oh, THAT. Damien Flamingo, the false idol.
"What about him?" she asked, not knowing what else they needed to discuss.
"I just wanted to talk about it. Like, what was his deal? Why was he acting like that? He never said anything like that on TV."
"Hun, the way he acted on TV was a mask. What we saw last night was the real deal. He's a heavy drinker that's obviously a sociopath and hates women. I think he's a lost cause after what he was spewing at Lusties that night."
The Brazilian nodded, understanding that. "Well, regardless, I'd still date a man like that."
"Why?" the blonde MILF asked, wondering why her friend would be willing to date an incel.
"For the money. Even if he is a filthy incel, the amount of money would still be worth it."
Jessie was kind of disgusted, outraged even.
"Marlena, no amount of money would be worth the verbal abuse that people like him would put you through. You should really think for yourself first."
Even though she was trying to give her advice, the Brazilian actress was already very set on her own ways.
"Still, money is what makes the world go round, If I dated an ass like that but he's rich, I will happily take the risk."
The blonde MILF shook her head. "Marlena, I know you're a gold-digger, but you gotta limit yourself. I don't wanna see you end up on the wrong path."
"Yeah, yeah. Sure. Anyway, I gotta let you go. Got any plans tonight?"
Jessie paused, thinking about how she just randomly changed the subject.
"Yeah, I'm gonna be hanging out with my daughter and my future step-son tonight. So, I won't be able to attend ladies night. It's a family gathering, and family matters."
The Brazilian understood, though wasn't able to relate. The only family she really had was her brother.
"Ah, alright. Well, have fun, Chica. I'll talk to you later."
"See ya, girl."
They both hung up, ending a rather conflicting conversation. The fact that Marlena would be willing to date a guy like Damien for money was rather foolish. But, that wasn't important.
Jessie went into her closet to get a rather cozy and relaxed outfit for her evening. She put on her white, pillow-looking sweater dress. She grabbed her purse and went out the door.
She got into her car, as walking to Justin's house would be a bit much for this 39 year-old to handle. She drove off, eager to spend time with him.
She got there at around 5 o'clock. Tiffany had yet to arrive, so she decided to call her.
"Hey, when are you gonna be here?" she asked, wondering when her daughter would be arriving.
"I'll be there in a few. I just got off work not too long ago, so I'm gonna be a while. You can go inside. Just ring the doorbell, he should let you in."
She nodded. "Alright. I'll see you soon." she said, hanging up the phone.
The blonde MILF got out of the car and knocked, just now realizing that he had a doorbell. How long has this been here?
"Hey, Hun? Are you home?" she said, proceeding to use the doorbell.
Suddenly, Justin answered the door. He smiled seeing her there. It was almost like a visit from an old friend.
"Hey, Jessie." he said, sounding a bit more cheerful than before.
"Well, look at you! All dressed up and everything. How's it going?"
He blushed, flattered at the compliment, even though he was wearing the usual purple button-up and black pants.
"It's going alright, for now."
For now?
"Please, come in." he said, holding the door for her like a gentleman.
She walked in, seeing the place looking clean. Well, cleaner than normal. She sat on the couch, hearing nothing but the sound of some 80's song playing in the background.
He sat next to her. Although the look on his face looked OK, the vibe he was giving off felt different.
"So, how are you? You and Tiffany getting along good?"
He shrugged, remembering the rather conflicting past they had together.
"Yeah, she's been pretty nice to me. Heh, I uh... I've been having a lot of fun with her over."
Jessie looked at him, having a slight grin on her face. "Oh really? What kind of fun?"
Somehow, he knew what she was thinking.
"Um, intense smooching and cuddling. Oh yeah, and spooning. She's also been showing me emotional support too."
She smirked at him. He was feeling sort of embarrassed, but he knew how she was.
"So, have you been doing well lately? Mentally, that is."
He nodded, though very slowly. It felt like he was trying to hide something, and she could see it.
"Can I ask you something?" he said.
"Sure, Sweetie. What's on your mind?" the blonde MILF said.
"So, I know me and your daughter have been committed for about 8 months so far, and I know I've made my morals clear about this, but do you think I should... you know?"
She tilted her head in confusion. "Should what?"
He swallowed, letting every single emotion come out of this one.
"Should I... Propose to her?"
Jessie's jaw immediately dropped. The fact that Justin "JD" Dark, the once most active playboy in the entire city, the man who slept with the Goddess of Love and screwed two space hookers to save the universe, was considering marriage was astounding.
"Oh, Sweetie... I-I don't think it's up to me. But, are you really considering it?"
He nodded, confirming his intentions.
"Oh, come here." she said, hugging him. She was so happy that he was considering marriage for him and Tiffany.
"I don't have an engagement ring yet, but as soon as I get it, I'm gonna propose to her at the right moment."
She nodded, tears of joy running down her face. "Regardless of what you do or how you get it, just know that you have my full support. I'm... I'm proud of you, JD. You've come a long way since we met over 3 years ago."
He smiled, glad that she gave him her approval. But, he still wanted the best for her. She needed a husband. Tiffany needed a father too, as that's something she never had during her childhood.
The blonde nurse walked through the door, happy to be done with work for the day.
"Ah, hey babe. Sorry I'm a little late." she said, kissing her boyfriend on the lips.
He blushed. "Oh, hey Tiffany. Welcome home. Or, what will be your home." he said, implying something.
She smiled. "Yeah, it'll be an adjustment, but Audrey's actually pretty stoked that I'm giving her the apartment."
The blonde MILF looked at her daughter, trying not to show that she was crying just moments before.
"Hey, Mom. How was work?" the blonde nurse asked.
"Oh, it sucked. I'm just glad to be out of there and spending time with my family."
She nodded. She then changed her clothes, as she already had some at his house. Yep, it was back to her weird obsession with the whole 'schoolgirl' outfit.
"I'll start dinner." she said to her boyfriend.
"Alright. What are we having?"
"Since it's family time, I'm making chicken alfredo, since I know you love it. I'll even add the broccoli in it, if you want."
JD licked his lips, excited to hear that she was cooking his favorite dish for dinner.
"Sounds great." he said.
She nodded, going into the kitchen. Before he knew it, he could hear the sounds of pots and pans clanging, as well as humming.
"She really does make you happy, doesn't she?" the blonde MILF asked, noticing that he was smiling.
"Yeah, she's the one who gives me the most joy nowadays. She's a life saver."
Jessie smiled. "I'm happy that she makes you happy. But, you know... There's someone that made ME happy."
He looked at her in confusion. "Who?"
"You, JD, you. Because of that vacation we had last November, I'm able to spend time with my daughter. You're the life saver."
Justin shrugged, still thinking he was getting too much credit after all this time. "It was nothing."
"Nonsense. You literally helped cure my depression. I really do appreciate you and everything you do, and I'm glad my daughter's been helping you with your emotions."
He nodded, though getting uneasy. She could tell he was still hiding stuff.
"Is there something bothering you?" she asked, suddenly getting concerned.
He shook his head. "No, nothing's bothering me. I was just thinking about uh... waffles is all."
Waffles? That's kinda random.
"Hey, but I heard about that Flamingo dude or whatever. I'm sorry that happened. Dude sounded like a total dick."
"Oh, you heard about that? Yeah, it was pretty messed up. I guess the saying 'never meet your heroes' is true."
He nodded, getting a bit uneasy.
"So, tell me something. What's been going on?" the blonde MILF asked, still trying to get answers.
"What are you talking about? I'm fine." he said, getting a bit defensive.
"Well, my daughter has been telling me that you've been acting off as of late. Is there something you're not telling me?"
He frowned, knowing that she was onto him.
"Listen, there's a time and a place for this. This is family time. We don't need to talk about it yet. Things might start to make sense soon, or not. I don't know."
The blonde MILF nodded, understanding his point. This was a family gathering. The important stuff could wait.
"Well, if you need me, you can call me if you want. Or better yet, you can come over to my house. You know where I live."
He blushed, remembering that she lived down the street near Vinnie's house. They hugged, as she could tell he needed it. Tiffany then came in, telling them that dinner was ready.
Justin and Jessie headed to the table where three, beautiful bowls of chicken alfredo were sitting.
"This looks so good, Tiffany." he said, complimenting his girlfriend.
"Thank you, Justin. Well, let's dig in." she said. They began to chow down on the chicken alfredo. Tonight was a good night. The food was great, the conversations they had were pretty satisfying, it was overall a good time.
A few hours had passed. Jessie decided to spend the night with them. She stayed in the guest bedroom, which once belonged to his innocent cat-girl. It had old pictures of her on the wall, as well as a card that read 'Thanks for everything, Master!". Although she had many questions, she knew it was bed time.
However, in the middle of the night, she was awoken by a horrible nightmare.
"No, no... Keep them away from me!"
She woke up in a cold sweat. She had a nightmare about her ongoing addiction to cigarettes.
"Uh, it was just a bad dream." she said, relieved that it wasn't real. Well, in a sense it was.
Jessie looked around, not feeling comfortable with sleeping by herself. She decided to go across the hall and into the master bedroom where JD and Tiffany were asleep.
"I'll just slip right in." she said. In a way, she thought of herself as a little kid sleeping with their parents after a nightmare about the boogeyman. However, it was the EXACT opposite.
Of course, feeling her get in bed alarmed Justin, waking him up.
"Jessie?" he said, also awakening the blonde MILF's daughter.
"Mom? What are you doing in our bed?" Tiffany asked.
"I uh... I had a nightmare about the smokes. So, I decided to come sleep with you two because I'm scared."
He shook his head, thinking that this was very immature for a woman her age.
"Jessie, you're 39 years old. You shouldn't be too afraid to go back to bed because of some boogeyman."
"Ciggyman, actually."
"Whatever." he said, sounding a bit stubborn.
"You know what? Babe, how about we let her sleep in bed with us. Just for tonight." the blonde nurse said, sounding like she was the mother, not Jessie.
"What the fuck?" he said, not exactly approving of his girlfriend's decision.
"Hey, if we have a kid one of these days, it'll be bound to happen. This is a good time to start practicing."
He frowned, knowing that he would've failed if his automatic reaction was 'what the fuck?'.
"Alright, she can sleep with us. But no funny business, young lady." he said, making it clear that this wasn't sexual.
Jessie smiled. "Yay!"
She was happy that they let her sleep with them. They all three fell asleep. As weird as it was to have both the Mayes in his bed, it was also unusually wholesome. They all got a good night's rest to prepare for the holy day of relaxation they would have tomorrow.