People unfortunately migrated inside after that, and Jessie was a little disappointed by how little she’d been able to flirt so far that night. She was about to go and check to see if Jack was ever going to show up but saw Cass sitting by herself at the edge of the pool.
Jessie went over to see if she was okay.
“You’re such a flirt,” Cass said with a smile. “You should give lessons.”
“I do what I can,” she said. “I love teasing and turning people on.”
“You’re a natural at it,” Cass told her.
“It’s just fun for me,” Jessie explained. “I don’t get hung up on things like most girls. I really just enjoy making other people happy.”
“I’m not shy, but I don’t think I can just get naked like you do in front of strangers,” Cass said.
“Yeah, I know how strange it sounds,” Jessie said. “I’m just different, I guess. I love to turn people on. I don’t care if people don’t like it, either. For the longest time Dex’s dad tried to get me to wear clothes when I was over here.”
“Don’s seen you naked?” Cass asked, a surprised look on her face.
“Lots of times,” Jessie said. “I’ve sunbathed naked a few times, but it all started with me cleaning naked.”
“Cleaning naked?” Cass asked.
“Mmmhmm,” Jessie confirmed. “I clean the house naked.”
The other girl looked confused.
“There’s no reason for it other than to turn Don on,” Jessie explained. “You’ve heard that his wife died some years ago, right?”
“Mom mentioned it,” Cass affirmed with a nod.
“Well, Dex and I were fooling around one day, and I kept seeing someone passing by his door. I obviously didn’t mind an audience, so when we finished, I told Dex about it. It took some time for our relationship to develop to the point that he was okay with sharing me in that way, but eventually he didn’t care if I got flirty with Don.”
“Wow,” Cass said, snickering quietly. “Did he… I dunno… like it, I guess?”
“Definitely,” Jessie confirmed with a giggle. “At first, he was very hesitant but eventually he realized that I wasn’t going to be dissuaded.”
Jessie looked over and saw through the door that Jack had arrived, to her delight and surprise, and was being introduced to the group.
“Gosh… I just wish I had your confidence,” Cass said. “I don’t think I could ever do something like that.”
“It’s just always been something that didn’t bother me,” Jessie shrugged.
“Did Don ever… like… get turned on?” Cass asked.
“Definitely,” Jessie confirmed. “It’s pretty easy to tell when the men in this family get aroused, though.”
Cass blushed at the information, and Jessie giggled in response.
“All three?” Cass asked, her voice a whisper.
“Mmmhmm,” Jessie said with a grin. “I’ll show you if you like.”
Unbeknownst to Cass, Jack had come outside was coming over to the pool in that moment.
“Hi Jack!” Jessie said, smiling up at him. “I’m glad you decided to join us!”
“Jessie,” he said with a smile. “I just wanted to say hi and introduce myself to everyone.”
“Oh?” Jessie asked. “This is my friend Cass,” she said, gesturing to the pretty blonde sitting on the edge of the pool.
“Nice to meet you,” Cass said, smiling as Jack waved.
“You too,” he said.
“Sit down,” Jessie said. “We’re talking about fun things.”
“I’m not interrupting?” he asked.
“Not at all,” she assured him.
“Why uh… why are you the only one naked?” he asked as he took a seat beside Cass.
Jessie giggled. “It just kinda happens with me,” she said with a shrug. She turned and gave Cass a smile. “Jack has been very weirded out by me,” she explained. “He doesn’t seem to like a naked girl running around his place.”
Jack chuckled and shook his head. “I don’t mind naked girls running around,” he said.
“Especially if they look like her,” Cass added, the other two laughing in response.
“So… what have y’all been up to?” he asked.
“I’ve been collecting hard-ons,” Jessie said, reaching up and running her hands up under her breasts. She lifted both, her hands moving up the flesh until she reached her nipples, her fingers gently pinching them as he watched.
She looked down into his lap and smiled, seeing the fabric of his shorts moving ever-so-slightly.
“That’s what I like to see,” she said, reaching out and squeezing her hand around the obvious erection.
Jack cleared his throat, seemingly not knowing what to do in that moment.
“Wow,” Cass muttered, staring unabashedly down as Jessie pulled the shaft a bit and tightened her hold on it. The sheer size of his cock was readily apparent to both girls.
“I uhh…” he stammered.
“That’s what I mean,” Jessie said, removing her hand and looking back at Cass. “Thank you, Jack,” she said. “You’ve settled a point for me.”
“Oh… uh… yeah,” he said, and stood to leave.
“You better let that thing go down a bit,” Jessie advised, giggling as he smirked at her then disappeared inside. “But yeah… all three of them are that well-endowed,” Jessie continued.
“God,” Cass said, sighing hard. “I’ve only ever been with the one guy,” she said. “He wasn’t anywhere near that big.”
“I’ve been meaning to ask you about that night you stayed,” Jessie said. “Why didn’t you have fun with my boyfriend?”
Cass sighed deeply. “I know Erin said that I should have been over it by then, but… I just wasn’t. She and Alec can fuck each other all over the house as far as I care. I’m not the same as her.”
“I understand having to heal from a broken heart,” Jessie assured her.
“Still,” Cass said. “I’d love to have your confidence and just… be able to flirt like you do. I just think that I’d be afraid of the consequences.”
“Well, I did kinda push things too far at one point,” she admitted with a giggle.
“You did?” Cass asked warily.
She nodded.
“I relentlessly flirted with Don for weeks,” she began. “I would clean naked, sunbathe naked, I’d even tell him to jerk off for me if he was feeling too pent up. He was such a hard nut to crack though. He only ever jerked off like… two times when I was there.”
“Wait… in front of you?” Cass asked, sounding shocked.
“Of course!” she confirmed. “That was the whole point. Dex was concerned about his dad and said that he was happy for me to be able to provide the… reason for him to have to jerk off. Sexual health is important for a person.”
“I… guess I didn’t realize…” Cass said.
“But like I said, he only ever did it twice,” Jessie continued. “For whatever reason, he felt bad each time he did. I didn’t stop trying though. I kept asking him to let me take care of him. I even upped the teasing a bit and hounded him about it as much as I could. Eventually, things came to head at Dex’s birthday party.”
“I heard that it was pretty crazy,” Cass said.
“Well, it was a clothing optional party,” Jessie explained with a shrug. “But Don was clearly enjoying all the naked bodies around. He’d was hard as a rock for most of it. Anyway…” she said.
Cass was looking at her with interest.
“He finally couldn’t take my teasing anymore,” Jessie said. “I wasn’t really even thinking about sex when he finally gave in to my charms. I’d gotten an ant bite on my inner thigh and asked him to take a look at it. I guess he just couldn’t take it anymore and before I realized that I’d pushed him too far, he’d yanked me off the counter and was fucking me up against the wall in his kitchen.”
Cass was quiet for a second, her eyes wide in surprise. “Wait… that’s what mom and Erin were talking about then!”
“What?” Jessie asked.
“Earlier this week, I heard them talking in my mom’s room,” Cass explained. “Mom was getting details about him, and I heard you and Dexter being mentioned by name. So… I listened out of sight and heard something about something happening between you and him.”
Jessie nodded with a smile. “Yep, that was him fucking me. He felt awful about it at first, but I eventually got him to calm down. I told Dexter about it and we worked through things, and eventually everyone came to a good place about what happened. I take full responsibility though,” she added, looking at Cass.
“That’s what Erin was saying,” Cass said, though she looked skeptical.
“I mean… come on,” Jessie said. “You’ve seen me flirting around here, can you really blame him for succumbing to my charms?”
Cass didn’t really seem to have an answer, and Jessie began to wonder if it had been a mistake to mention it. “Are you okay?” she asked.
“Hrm?” Cass replied. “Oh… yeah,” she said, waving a hand dismissively. “It’s just a lot to take in, you know?”
Jessie nodded, and immediately began to feel better seeing the smile on Cass’s face.
“Come on,” Cass said, gesturing to the house and reaching for Jessie’s hand. “Let’s go see what’s going on.”
***
The two went back inside with the others and Jessie found Dexter playing some kind of drinking game with the others. He asked her if she’d been misbehaving, and by her standards the answer was no. But there wasn’t anything to be gained by telling him that, so she simply said “of course,” and left it up to his imagination.
He excused himself from the game not long after, and she happily took his place. Jack joined not too long after, and the two quickly teamed up to make the others drink more than they had to.
The game ended eventually, and the group split back up into groups again. Jessie listened in to several conversations, waiting for the right time for things to get heated so she could get flirty for Dex again.
Much to her irritation, nothing seemed to come together right, and she found herself thinking that nothing fun was going to happen that evening.
Around midnight, Jessie went and found Jack again. He’d been sitting and talking with Blake and Sandy about something. The conversation came to an end, and the two excused themselves and went to find an empty room. He glanced over and saw her studying him, then chuckled and shook his head.
“When are you going to let me suck your cock again?” she asked.
He smirked and shook his head in dismay. “You’re relentless, you know that?”
“Come on,” she said, and held her hand out to him. “I’ll take you up to your bedroom so that no one can see, then you can pump my mouth full of cum and be back down here before anyone knows you’re gone.”
Jack looked up at her and smirked, then to her amazement, reached out and took her hand as he stood. Momentarily shocked, she took a few seconds to start moving. She’d passed the hallway to the den with Jack in tow when a commotion stopped them both.
Daisy stomped past the two with Tyson in hot pursuit, the two obviously arguing.
She stopped just on the other side of Jessie and Jack and whirled on Tyson angrily. “I didn’t know what was going on in there!” she snapped.