Late Night Truth or Dare Ch. 05-06

Author's Note: At its heart, this is a college harem series, but as it contains incest, it must be categorized accordingly.

This is the fifth and sixth chapters in the Late Night Truth or Dare Series. Although new characters and plot lines originate in these, I do not recommend reading these as stand-alone stories as they will be missing context and character development from the prior installments.

This version has been revised from the original to correct mistakes and reformat for better reading online. Additionally, the title has been changed to eliminate confusion about the order of the stories.

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Late Night Truth or Dare - Deep Throat Training

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Jennifer Murphey's breasts bounced with each stride.

Her sports bra contained but failed to control their motion, as their ample size was too much for even the sturdiest support system.

She didn't have a runner's body like her daughter, but that didn't prevent the enjoyment of her morning runs. Except when her period was approaching, and the tenderness in her breasts made anything over an easy jog painful.

She relished beginning her days in the cool fresh air, with the morning sun gently tanning her Italian skin as she cruised around the local lake.

In the summer, she wore short shorts and a sports bra, enjoying the sun on her skin and showing off to the middle-aged men she routinely passed.

They tried to hide their glances, but she always saw, smiling to herself at their attention. Luckily, they were all respectful and left her to jog in peace.

Her husband would be mortified if he found out. He was an old-fashioned Irish Catholic man and thought she should cover up whenever she left the house.

Usually, she obeyed him, but she'd convinced him she overheated if she wore too many clothes while running, which was partially true. She failed to mention where she ran or how many men were there when she did.

The glances were just fun and games, something her husband didn't need to know about. None of the men dared to approach her anyway.

It took a boy to finally make a move on her.

She stuck to the same route each day, as it made it easy to time her mornings. The views never disappointed her, especially since Ian, the boy from down the block and childhood friend of her daughter, picked up running.

At first, she'd see him passing her, and they'd exchange pleasantries. Gradually she ran into him with more frequency.

A few weeks ago, he'd met her at the start of the lake loop, waiting to run with her at a pace far slower than his usual, and she'd met him every day since.

Their conversations began banal and innocent, but the more they ran, the more they opened up to each other. Even flirting a bit.

As she rounded the corner, she saw this day was no different.

"Hey, Mrs. Murphey. You're looking good today," Ian said with a smile.

"You're very kind, Ian. You look like you've already put in a few laps," Jennifer responded.

Truth be told, Jennifer knew she looked good. At forty-five, she'd kept in great shape since the birth of her second child. In addition to running most days, she maintained a strength training regime.

It was nothing to make her too muscular and just enough to keep her toned, with a round ass to match her breasts.

She'd led a life of little stress, leaving her face looking like someone in their early thirties.

If her husband would let her, she'd flaunt her looks all over town. As it was, she was relegated to the local park between seven and eight in the morning.

"A few. I'm trying to get in shape for college. I'm going to try and walk on to the baseball team."

"Well, you look in good shape to me," Jennifer said, glancing over the teenager's body.

When they'd started running together, Ian wore tank tops. After a week, he'd ditched those to go topless.

Jennifer hadn't complained as she enjoyed seeing the boy's muscles ripple and bounce as he ran next to her.

She'd been the center of attention for all the men for so long that she thought it was about time someone gave her something to look at.

As they circled the lake for a second time, they joked, flirted, and exchanged glances they hoped the other would forgive. It was nothing too serious, but Jennifer knew Ian grew more smitten with her every run.

Jennifer didn't yet realize it, but Ian would've done anything she asked.

She'd begun to fantasize about him. Even going so far as to masturbate while imagining him fucking her from behind but despite the lack of sex or anything sensual in her marriage, she wasn't ready to cross that line.

Ian reminded her of her son, Bobby. Although he had the red hair and fair complexion of her daughter, Sarah, something she'd inherited from her father.

Ian and Sarah had just graduated high school together but despite being childhood friends, they hadn't socialized much in the last five years.

Bobby and Ian shared a sharp jawline and low body fat, eagerly displaying their well-defined muscles. She'd occasionally caught herself staring at her son by the pool, but this was always followed by a hint of shame.

With Ian, she didn't have to suppress her thoughts, as long as she let them remain secret desires and didn't act on her urges.

"I've got to get to work. I'll see you next time," Jennifer said as she abruptly peeled off from Ian, her mind having wandered too far into the gutter.

She was glad she had to leave for work before her husband. Otherwise, the urge to divert the run to Ian's bedroom might've been too much.

The lack of convenience might be the only thing keeping her from acting on her yearnings.

*****

"Did Mom tell you that her and Dad are heading to Aunt Molly's this weekend?" Bobby asked his sister as she snuggled next to him in bed.

She'd joined him after their parents had left for work, which had become a habit over the last week.

Most of the time, the siblings had sex, but sometimes Sarah practiced her deep throat skills, taking her brother's cock further each time. She'd come a long way since Ashley had given her pointers, but she still couldn't take all of Bobby's dick into her mouth.

They'd lie naked in each other's arms until one of them had to rise. This usually resulted in two or three rounds and them lingering in bed until noon.

"She did. Why? What are you thinking?" Sarah responded, hoping her brother was on the same page as her.

"I thought we could invite some people over. I could even buy some alcohol if people chip in. I spent my last pennies on that lingerie."

"I'm sure I can collect some money. The girls would be more than happy to donate to a good cause. Are you wanting to keep it to the six of us? If not, we could get a lot more money."

"I'm not selfish. I'm willing to share. So, if you want to invite some other guys, that's fine with me. As long as they know how to behave."

"I'll talk to Dee and Ashley and see who we can round up," Sarah said. "I don't want to invite too many people as we'll have to clean up before Mom and Dad get home Sunday night."

"Maybe an equal number of guys and girls? We can actually play a real game of Truth or Dare that way, assuming everyone is willing."

"That'd be fun," Sarah mused.

"But we'll have to keep it tame between the two of us. We don't want word getting out."

"That's fine, I'll just sneak into your bed after everyone is passed out, but we don't need to worry about that right now," Sarah whispered as she slipped her hand between her brother's legs. "Looks like you're ready for round two."

Lowering her head, she took his cock into her mouth, slowly and steadily bobbing up and down, and sinking deeper with each pass.

Bobby leaned his head back and let his sister work her tongue around his shaft. She wasn't as good as Ashley, but she was only an inch away from burying her nose in his pubic hair.

After she got comfortable with that, then the real fun could begin.

"You're going deeper every day," Bobby said, gently resting his hand on his sister's head.

His fingers disappeared under her hair as she held still, pushing the limits of her gag reflex.

*****

Sarah's phone dinged with a new group text:

Ashley: I got Blake and Jesse to come. They're both cool once you get them away from the rest of the preps. They can keep their mouths shut and have decent dick's as well.

Dee: Nice, Jesse is a great lay. I think Diego is coming. He's the only one from the football team I trust to invite.

Sarah: Awesome. That leaves one more guy to make it even. Any ideas?

Bella: What about Ian? You two were friends when you were young. He's pretty hot these days.

Sarah: I haven't hung out with him in forever, but I'll ask. He's got a great body.

Candice: What's the plan? Say it's a small pool party and then sneak in the game when everyone's horny?

Ashley: That's what I'm thinking.

Sarah: Bobby said he'd only do this if everyone uses a condom. And no mentioning me and him, okay?

Dee: Deal. Tell him to get White Claw. I can't stand beer.

*****

Sarah stood nervously outside Ian's house. She didn't know why she was worried. They'd been best friends when they were young. They'd play in the cul-de-sac every day until their parents called them in for dinner.

That was over ten years ago, however, and things had changed. Specifically, Ian had changed.

He'd gone from a dorky little boy to the hunky star of the baseball team. He was now one of the most popular kids in school and had his pick of girlfriends if he desired.

The weird thing was that Ian hadn't dated anyone in high school.

There'd been rumors he was gay, but Sarah didn't believe them. She thought he was just picky and wouldn't settle for some bimbo who wanted to date him as a status play.

She had to admit it was odd that a high school boy would pass up guaranteed sex, but then again, Ian wasn't your normal high schooler.

"Hey, Sarah. I haven't seen you in a minute. What's up?" Ian answered the door, wearing only a pair of mesh basketball shorts.

"Oh, um, nothing much," Sarah mumbled, trying not to stare at Ian's body. "I just wanted to invite you over Saturday. We're having a small pool party before we leave for college, and I thought you might want to come. You know, for old time's sake."

Sarah realized that Ian looked a lot like photos of her dad when he was young. Not that her dad was ever as ripped as Ian, but their posture and face were shockingly similar. She guessed it was their thickly Irish genetics.

"Is your mom going to be there?" Ian asked.

"No, my parents will be out of town, and my brother has promised to buy us alcohol if people chip in for the cost."

Sarah swore she could see the disappointment on Ian's face when she said her mom wouldn't be there. It was the opposite of what she'd expected.

"I'll think about it," Ian said, "it would be nice to catch up before college."

"It'll just be a few of us, but I think you'll enjoy yourself. My friends don't bite--"

"Unless I want them too?" Ian finished her joke.

"Exactly. Just bring your swimsuit and those abs."

Sarah was instantly embarrassed as the words flowed from her mouth. She'd said them confidently, a departure from her usually shy behavior, but was unsure how Ian would take the compliment.

"I'll try to remember the suit," Ian smirked, leaning into the flirting, "unless we're skinny dipping like we did when we were three."

"If we do, it won't be anything like it was back then," Sarah gave Ian a more obvious once over, noticing the hint of an erection beneath his shorts.

She couldn't believe how natural flirting had become. Sarah had gained so much confidence since first sleeping with her brother.

She was also surprised that despite her love for Bobby, she couldn't help but think of what it'd be like to sleep with Ian.

Bobby said she was free to play around as he'd done with her friends, but so far, she hadn't tested the waters. Not that she'd been looking until Ian caught her eye.

She'd been worried about Saturday as she wouldn't be able to fuck her brother with other people around. Unsure if she'd want to mess around with other guys, but Ian had her thinking Saturday might be more fun than anticipated.

"I'll be there. Hopefully, your friends are as fun as you imply."

"We're more fun. We've been unleashed this summer," Sarah said with a wink before turning and heading home, leaving Ian standing in the doorway, wondering what he'd agreed to.

*****

"Hey, Mrs. Murphey," Ian said as he slid next to her on the trail, slowing his pace to match hers. "Did Sarah tell you she invited me over on Saturday?"

"Like a date?" Jennifer responded with a hint of jealousy in her voice.

"Oh. I don't think so. She said some of her friends were coming by to swim, and it would be fun to catch up," Ian replied. "Do you think it's a date?"

Ian had picked up on Sarah's flirting, but he hadn't thought much of it. He'd figured it was just her way of getting him to come over, probably to give her friends some eye candy.

He thought they were all a bit dorky and assumed they were inexperienced with boys, but he didn't mind being ogled, as he loved showing off his body, and the nerdy girls were always the most appreciative.

Plus, he never complained about being able to check out girls in swimsuits, although he wished Mrs. Murphey and her mature curves would be there.

Despite not inheriting the sensual features of her mother, Sarah was still cute and transmitted the same energy that drew Ian to Mrs. Murphey. Ian wondered if Sarah was expecting more of him than he'd assumed, if so, he wasn't sure he'd pass it up.

"Well, I hope she's not planning a party while her father and I are out of town."

"No, nothing like that. Sarah's not really the partying type," Ian said, hoping he hadn't ruined anything for her.

"You know, I always thought you two would've made a good couple. You're both smart and athletic... " Jennifer paused, contemplating how to finish her thought, "but Sarah never really developed physically, you know? I mean, there's nothing wrong with her, and it helps her running immensely. But I don't know what I would do without these," Jennifer grabbed her breasts, juggling them slightly, drawing Ian's eyes to her chest. "Are you a boob man, Ian?"

The question caught Ian off guard. He and Mrs. Murphey had flirted during their runs, but they'd never talked about anything so explicitly sexual.

She'd definitely seen him check her out, but then again, she'd practically pushed her tits in his face. What warm-blooded male wouldn't stare? Boob man or not.

"I'm attracted to all types of women," Ian tried to mix truth with diplomacy.

"But if you had a choice, say, between someone like me or my daughter?" Jennifer teased Ian, knowing she was making him uncomfortable.

"I, uh, I am not sure I should answer that," Ian stammered.

"Don't worry. I'm not going to judge you one way or another. It's just talk amongst friends."

"Well, I prefer someone with more curves. Something to grab onto, you know?" Ian couldn't believe he was telling her this. It felt inappropriate, but she didn't seem fazed. "Not that Sarah is not attractive," he added, slightly panicked that he'd said the wrong thing.

"Yes, she is, but I wouldn't trade my body for hers," Jennifer reassured Ian. "Not that I get grabbed enough these days."

"I, uh, well, Mr. Murphey is a lucky man," Ian said, not knowing how to respond to what she'd just said.

"Thank you for that. I just wish he remembered that more often. Not that he was ever a superstar in bed," Jennifer lamented. "I'm sorry. You don't need to be hearing about this."

"It's okay. I enjoy having more adult discussions with you. My friends can be such morons. It drives me insane. I honestly prefer more mature company," Ian admitted. "That's too bad about your husband. Let me know if I can do anything to help."

Jennifer didn't reply and glanced questioningly at Ian, trying to ascertain if it was an innocent slip of the tongue or if he was hinting at wanting to take things further.

She'd never seriously contemplated cheating on her husband.

Until recently, she'd thought her flirting with Ian had been innocent and safe, if out of bounds by her husband's standards.

If Ian suggested what he seemed to, she had a difficult choice. She wasn't sure she'd be able to resist him if he made a move on her. She knew she should, but the more she thought about it, the less she wanted to resist.

"Oh no, I didn't mean it like that. I was just saying, I'm here if you need to talk," Ian blurted out, mortified he'd pushed too far.

He wanted to sleep with Mrs. Murphey, but he hadn't meant to say it aloud.

"Don't worry. It happens all the time. I accidentally called my dentist 'daddy' last week," Jennifer tried to reassure her running companion. "Don't ask. I was on nitrous at the time. And thank you for the offer. It's always nice to have options."

It was Ian's turn to wonder what exactly Jennifer had meant. She couldn't possibly be suggesting that he was a potential replacement for her husband, could she?

Even if she was merely hinting at the possibility of an affair, Ian wouldn't know what to do. He'd always gone after older women, having had success with several ladies in their late 20s but Jennifer Murphey was in a different league.

It would be a dream come true, but it terrified him that he wouldn't live up to her expectations if it did.

The two giggled in shared awkwardness, finishing their run in silence, both too nervous to ask the questions racing through their heads.

As they parted, with Jennifer heading home and Ian taking a few more laps, their gazes lingered, and each wondered if the other shared their feelings.

*****

Candice: Hey, I want to get a new suit for tomorrow. Anyone want to come shopping with me?

Sarah: I'm always down to cum with you. Just let me know when ;)

Dee: I've got plans today, but I already have something special picked out for tomorrow. Have fun.

Ashley: I don't need anything, but I've got nothing better to do.

Candice: Bella?

Bella: I'd love to, but I don't have any money.

Ashley: I owe you a birthday present. Come along, I'll buy you something cute.

Candice: I don't think we are going for cute.

The girls met at the mall in the early afternoon, giddy and eager to find the sexiest swimsuits they could dig up. An hour and a half later, they stood near the food court, disappointed their usual shopping locations didn't have what they were looking for.

They found plenty of suits they liked, but nothing was sexy enough, as all had been designed for use in public. They needed to find where the slutty Instagram models were shopping.

"Would we have better luck at a lingerie store?" Candice asked.

"Do they sell swimsuits? I honestly have no idea. I've never bought one from anywhere other than PacSun, but those don't reveal anything other than some under boob if you buy a size down," Ashley replied.

"There's that store down the road. They sell lingerie, and it seems more erotic than anything we'd find here," Sarah suggested.

"We might as well give it a try. It's not like we're finding anything here. At least nothing that'll shock the boys," Candice said with a shrug.

The girls hesitated as they stood outside the store. None of them had been inside before, and they now realized it was more of a fetish wear store than anything else.

Walking through the doors, they expected to be accosted for being too young, as the reality of being eighteen was not yet fully realized by the girls.

They were surprised by how ordinary it seemed inside. It wasn't a sex shop, but the store did specialize in unique lingerie and fetish wear, with sections devoted to leather and latex. Another was dedicated to roleplay costumes, most of which were not significantly different from your typical "sexy" Halloween get-ups.