Late Night Truth or Dare Ch. 08

Author's Note: As with all my stories, this series spans multiple categories. Given the prevalence of incest, I have categorized it as such.

This is the final chapter in the Late Night Truth or Dare Series. I do not recommend reading this as a stand-alone story, as it will be missing much of the context and character development from the prior installments.

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Late Night Truth or Dare - The Finale

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"Should we throw a party for your brother's graduation?" Jennifer asked Sarah as they sat for breakfast.

They both wore oversized t-shirts, but not ones long enough to prevent their pussies from peaking out as they sat. Their breasts swayed freely as they settled in their seats, albeit, Jennifer's much more than her daughters.

When Jennifer's divorce had finalized with Sarah and Bobby's father, she had moved to be closer to her daughter, buying a house that sat on a few acres outside Scottsdale. Sarah moved in despite the longer commute, after growing tired of living in the dorms and the constant party scene in Tempe.

Ashley, who'd gone to college with Sarah, still technically lived in the dorms but spent most of her time in Jennifer's house as well. The longer the school year drug on, the less she wanted to sleep on a twin bed, opting to share a queen with Sarah most nights. Occasionally, they'd both sleep with Jennifer in the master, not quite filling the king. Usually, with the flat chested Sarah being sandwiched between the two top heavy women. They were happy and often had fun together, but non of them had fucked a guy since winter break. Not that they were interested in anyone available to them.

After her divorce, Jennifer gave in to her feelings for Sarah's half brother and her husband's love child, Ian, and despite his pleas for her to get out and experience other men, she was saving herself for him. Sure, she'd fooled around with Ashley and Sarah, but she didn't count that as they all realized they came as some sort of weird package now. If you bought into one you got everyone for the same price, or more accurately, the same dick.

Sarah, for much the same reasons, was waiting for her brother, Bobby. She'd tried fucking around her first semester in college, but nothing felt right and in the end, she decided she'd just wait for Bobby to graduate and move in with her and their mom. It would be crowded in the three bedroom home with Ashley around, but they were all going to be family, lovers, and roommates, depending on how you looked at it. The neighbors would give them weird looks, but no one knew their true relationships, so there was no fear of being condemned for incest, just run of the mill polyamory.

Ashley, for her part, had continued to sleep with as many guys as she could until her supply dried up. The faucet turned off for her early in the second semester. Guys she'd been fuck buddies with no longer wanted to hang out, and new recruits seemed turned off by her. She'd gained some weight, but ultimately she just chalked it up to them being boys. Once she started to look at them differently, they treated her in kind, viewing her as older than her years. She needed a man. She needed a soon to be college graduate. She needed Bobby.

"For sure. We'll throw him a party he'll remember," an enormous smile crept across Sarah's face. "He's gonna be tired, but if we invite the girls and Ian, I'm sure he'll perk up and have a ball."

"If he doesn't, we can have fun without him," Jennifer replied. "I've missed Bobby, but I've been dying to see Ian. I'm still pissed he couldn't take spring break because of baseball. He's going to feel sooo good inside me."

"Why didn't you just go down there and visit him like you did on Halloween?"

"I thought about it, but he's in college and I want him to be having fun fucking girls his age. I don't want him to spend his entire time thinking about me. If he chooses me in the end, awesome, we can have fuck for the rest of our lives, but I want to make sure he chooses me after he's had a selection of what's out there. I don't want him craving college pussy five years from now because he missed out."

"Sure, but I don't think it's college pussy you've got to worry about with Ian. You're gonna end up loosing him to Grandma," Sarah winked. "Plus, it's not like you're going out and trying on new men after you left dad. Nor am I fucking every guy I can. I'm just waiting for Bobby, and you seem okay with that."

"You're doing everything right for you. Men are different. They want to sow their oats, and I just want to make sure Ian feels like he can do that without me looking over his shoulder and questioning every girl he fucks," Jennifer grimaced, not fully accepting her own words. "And with you. Your brother will be here in a month. It's not like he has another three years before he graduates. He's done his time. Fucked his girls. Anyway, he'll have a selection waiting for him when he gets here."

"Fine. I see your point, but I'm sure Ian's just as excited to see you," Sarah smiled as she placed he hand on her mothers thigh, rubbing her new tattoo gently as she inched under the hem of her night shirt.

***

"Wait, wait, wait. You fucked both the mother and the daughter? In the same weekend?" Colleen asked as she wrapped her naked body around Ian's. "That's... that's... I don't know. Even for me, that's wild. It's also fucking hot as shit."

Her leg draped over his and her freshly fucked cunt oozed against his thigh. She idly played with his cock, waiting for him to recover so she could ride him to another glorious orgasm.

"Yeah," Ian chuckled. "Sarah, the daughter, invited me to a party, which turned out to just be one big fuck fest. I mean, her brother disappeared into his bedroom with two of her friends. I ended up fucking Sarah. Then two more of her friends after they were left wanting by the assholes they'd hooked up with first," Ian smiled recalling the weekend.

"How'd her mom happen?"

"So, she was supposed to have been gone for the weekend with her husband, but they'd had a huge fight, so she came home early. I just happened to be walking into the kitchen when she came in through the garage. I was completely naked. My dick still crusty from the night before," Ian's smiled widened. "We'd been running together most morning at that point, and been quite flirty. I didn't think either of us would've crossed that line without a push, but once she saw my cock it was on. Her husband didn't matter. My night with her daughter didn't matter. All that mattered was me buried balls deep in her cunt."

"In a fucked up way, that's actually kind of romantic. I'm a sucker for a good cuckold story. Is that why you two were hooking up in the hotel when I met you? Is she still sneaking around on him?"

Ian hadn't sought out Colleen. He'd had a lot of fun when Jennifer had invited her into their hotel room. She had a gorgeous body and could fuck like a woman twice her age. He just wasn't looking for hookups, despite Jennifer's insistence he do so. He'd run into Colleen at a party, and they had chatted and reminisced. Then, Colleen had made it very clear she wanted another go at his cock. She wouldn't accept no, so Ian did what he had to and took he back to his place and fucked the shit out of her. The sex had been amazing, but, because of their past threesome with Jennifer, his mind kept wandering, drifting from Colleen to Jennifer and back.

Colleen was young for his taste, but she had skills like an older woman, making a fine substitute for Jennifer. Ian appreciated that she was a unique package. The body of a college girl, but the experience of a dirty housewife. He wanted to keep screwing her, but needed to be certain she knew where his heart lay.

"No. They're divorced now, and she moved to be close to her daughter, who's in Tempe. I cant blame her, but I'm disappointed she didn't come down here. She said that she wants me to have more experiences. Fuck other women. Then, only if I still want to be with her after college, will she live with me. I understand, I guess, but really I just want her," Ian stared at his ceiling, "No offense, you're great, especially in bed, but----"

"But you're in love with her."

"I am," Ian gently nodded his head as his fingers idly played with Colleen's nipple. "I love her. It's a little weird saying that while curled up with you, but nothing's normal with Jennifer and her family."

"Naked in bed with me or not, I think it's great you love her. It's fucking hot, especially that she was cool with you sleeping with her daughter. Have you fucked Sarah since?" Colleen's hand gripped Ian's cock a little harder, feeling the blood return. "I once tried to fuck a father and son when they were staying at the hotel. I got the father, but never could get the son alone long enough."

"I doubt he would've lasted long," Ian smiled. "I'm sure you've got all sorts of wild stories. Just the fact that you fucked me and Jennifer, that's pretty fucking crazy for most people."

"I've got some. Honestly, though? Nothing compares to yours, and even then, I feel like you're holding out on me. There's more to that family, isn't there?"

"You have no idea... " Ian trailed off, debating whether to fill Colleen in, "but that's more of a third date conversation, if you know what I mean?"

"Wait. Aren't we supposed to wait until the third date to fuck, not share secrets?" Colleen laughed. "How about I suck this dick hard again, and then fuck you for a third time? Will that count?"

***

Sarah: Aight girls, Bobby's getting to Scottsdale on the 14th. The party's that night. You need to be here before he arrives around 7. He's suspecting something, but hopefully he doesn't know you all are coming... and hopefully cumming.

Candace: Aight? Whatcha using aight for, bitch? You got to college and now think you're black?

Sarah: I'm sorry. I meant, "Alright, ladies."

Candace: I think you mean, all right. I'm just fucking with you anyway :) Aight's no longer part of the culture anyway.

Ashley: The fuck you know about the culture? You grew up in white suburbia with the rest of us ;)

Dee: Anyway... Mark and I won't be able to make it until the 15th. My last final is the evening of the 14th, so it's just not possible. Then again, it's probably best if you all have your fun before Mark gets there. He's pretty open minded, but I don't want to explain everything to him. At least not yet.

Sarah: You mean that I fuck my brothers? Yeah, that makes sense. We'll be by the pool all day on the 15th, so it will be perfect for him to meet us all. I can't wait.

Candace: I'm sooooo excited for this. I've been doing nothing but training and studying all semester. I can't wait to let loose. Hopefully Mark doesn't mind nudity, because I don't plan on putting clothes on until I leave ;)

Dee: I doubt he'll mind. He's a man after all. Just don't tell him about how everyone is related.

Ashley: Done. Has anyone heard from Bella?

Candace: Not directly, but I was told she didn't end up in college and went back to Mexico with her family. I have no idea why. Nor do I know why she hasn't reached out to any of us. I'm worried about her. I hope everything is all right.

Sarah: Me too. I will miss having her at the party. It's not going to be the same without her. I reached out on all her socials, but she hasn't posted anything since last summer, so I doubt she'll reply.

Dee: Let us know if you hear anything. I'll see you all on the 15th, and I hope you have SOOO much fun the night before. I'd be jealous if Mark wasn't such an amazing guy.

Ashley: I can't wait to fuck... I mean, meet him ;)

***

"Fuck. I can't believe this is it," Bobby said as he slouched on the couch, stretching his arms above his head, and staring out the window at his packed car, before running his hands through his hair, leaving it standing in spots. "It doesn't feel like it's been four years yet."

"I know, right? It feels like yesterday that you came walking through that dorm room door, still looking like a scrawny high school kid," John replied back, cracking open a beer, ready to enjoy his post collegiate life, but not yet ready to give up the partying. "Remember that haircut? And what was that fucking boyband t-shirt you had on?"

"Fuck you. It was Nickleback. A boyband would've been less embarrassing," Bobby smiled at his roommate. "Like you were some stud back then? Although, all that gym time's paid off," he flexed, showing off his defined biceps.

"Especially for you, bro. Are you leaving this afternoon?"

"Yeah. I've got to get up to Scottsdale this evening," Bobby shrugged. "They're planning a surprise party."

"Some surprise," John rolled his eyes. "Well, hopefully those girls from Halloween will be there. I'm sad they didn't come back this semester. I bet you can't wait to get your dick wet again," John swirled his hips, mocking fucking motion, albeit, a very bad one.

"They'll be there. It should be fun. Hopefully they're all still into me and haven't moved on. They say they haven't, but you never know."

"Well, even if it's just one or two of them, I'm sure you'll survive," John rolled his eyes. "You've always got the good pussy."

"Well, it's been real, man. I'll invite you up when I get settled. If my job pays as well as it should, I've got my eye on a plot of land up there. Already talked to the owners and everything. I'm thinking of building a party compound. I'll keep you on the short list for events," Bobby said, standing and reaching his arms out to hug his roommate.

"'Till then, my man," John said, returning the hug. "Drive safe. Not like you'll listen."

***

"Everyone get down----"

"This is a robbery!"

"Shut the fuck up, Ashley," Candace playfully jabbed her friend with her elbow.

"He's coming up the driveway," Jennifer finished, turning her head to make sure everyone complied before she returned to peeking out the window.

She smoothed the front of her dress, took a deep breath, and timed the opening of the front door to catch Bobby just before he knocked.

"Oh my God. It's so good to see you," Jennifer reached out and pulled him to her, wrapping her arms around him and hugging him tight. "I've missed you so much, honey. Your sister's going to be so happy you're here."

It was weird and performative, which confirmed what Bobby had guessed. There was a "surprise" coming, and it was going to be a long night. It would be fun, probably one for the ages, but he wasn't going to catch up on the sleep he'd missed during finals week.

"Hey, Mom. I'm glad to see you too, but honestly, I'm exhausted. I just want to eat something and get some sleep. Can we catch up in the morning?" Bobby leaned back, looking his mom in the eyes, trying to sell the fatigue.

It wasn't fake, but he also knew he'd rally once the festivities kicked off. Hell, just having his mom's breasts pressed into his chest already had his cock stirring. Or maybe it was the thoughts of what he'd do to his sister. She's the one he'd been missing. His mom was great, with perfect breasts, but really he'd come to Scottsdale for Sarah... and Ashley. Oh, how could he forget Ashley? Speaking of perfect breasts. He couldn't wait to have his cock deep in her throat. Especially if she was switching off with Sarah.

"Oh, nonsense. You can recover tomorrow. Tonight's for getting reacquainted with your friends, or maybe lovers is a better term? I'll put some coffee on. You're going to need your energy to keep up," Jennifer's voice grew louder and more performative as she turned and presented Bobby to the seemingly empty living room.

"Surprise!" Everyone said in unison, each jumping from their hiding place wearing, well, not wearing anything at all.

"Oh, shit," Bobby laughed, actually surprised by the nudity. "Fuck, y'all, you really didn't have to. I... I would've been happy to take your clothes off one by one," he smiled as he stepped through the door, awaiting the first hug.

Candace stepped forward, hugging Bobby and letting her hands slip to his ass. She kissed him, just a peck at first, but it quickly escalated as she slid her tongue into his mouth.

Finally, she whispered in his ear, "I've missed this cock," as she wrapped her fingers around his rapidly stiffening shaft.

Ian was next, giving him a quick bro hug and a slap on the back. "I can't wait to get this party started. I know it's weird, but I've fucking missed your mom, man."

"You mean, you've missed fucking my mom," Bobby smiled as they separated. "Who's gonna to be our first double team?"

"That'd be me, bros," Sarah stepped between her two brothers. "It's only fitting that I get you two from both ends. Although, with all these lovely ladies here, I'm not sure I can Bogart you too all night. I guess I'll share. Even if I don't want to," she raised her eyebrows. She grabbed Ian's cock in one hand and Bobby's through his shorts. "These two are going to be put through a lot of work. I hope they're up for it," she finished with a squeeze of each.

"I've missed you, sis," Bobby said as he pulled his naked sister against his body. "We've got a lot of lost time to make up for."

"Thankfully, we've got all summer. I don't have any classes, and no one around here knows we're related. It's going to be a lot of fun," Sarah kissed her brother on his lips, but quickly pulled back. "But... it's also going to be a lot of work. Mom said she'd help, but since it wasn't her doing, she says we all need to chip in. Especially, you."

"Wha---- What're you talking about?" Bobby cocked his head as he leaned back from his sister.

"She's talking about me," Ashley said as she stepped into the living room. "More specifically, she's talking about our child."

"Holy shit. This----this is an actual surprise. Look at you. I didn't think your breasts could get any larger," Bobby clasped his face before placing his hands on Ashley's enlarged belly. "And this----this... Holy fucking shit, you look like you're about to pop. When are you due?" Bobby rambled in response to the shock.

He'd known it was only a matter of time before someone got pregnant, but no one had told him it had already happened. He'd assumed someone would've told him. Why didn't anyone tell him? By the looks of her, he must have knocked her up back in August, before she even went to college. If that was the case, then she'd have know over winter break... or even at Halloween.

"Why didn't you tell me?" Bobby looked in Ashley's eyes before darting his gaze around the room to the others, who must have know. "Why didn't any of you tell me?"

"We wanted it to be a surprise. A graduation gift if you may. Are you excited?" Ashley stepped toward him, her face betraying her attempt to contain nerves.

"Excited? I mean, fuck, of course, I just wish I'd known. I could've prepared, learned what to do, taken care of you. I don't know. I feel like I've already fucked up as a dad and the baby isn't even here yet. What do you need me to do?"

"It's okay," Ashley soothed as she pulled him into a hug. "Your mom and Sarah took good care of me. We didn't want to burden you during your senior year. We wanted to make sure you got the job you wanted and were able to have fun while you could. I'm sorry if you're upset, but we meant the best. I hope you can forgive me. You'll be a great dad."

"Of course. Of course. Oh my God, you're forgiven," Bobby sank to his knees and kissed Ashley's belly. "Is it a boy or a girl?" He asked as he began to control his thinking.

"We don't know," Ashley smiled, a bit wickedly, "but everyone says it's a girl. They think she's going to be a slut like me."