Truth or Dare

Nate was quite excited for tonight. For tonight was his and his twin sister Natalie's high school graduation party. Their mom had told them that she would allow them to do whatever they wanted for this party, giving them free rein over the entire property, save for her own room and the small loft that was above their unused barn where she'd spend the night. Although they weren't the most popular amongst their classmates, Nate and Nat had invited the entire graduating class of 200 to come and live it up one last time as a group. Sure, they had decided to throw this party even after Shelby Greene (the most popular and hottest girl in their school) had announced hers a week before; but they had 3 acres of private field, a large pool and no neighbours to complain and call the cops. Nate knew which party he'd choose to go to, despite never really being much of a party animal the past four years.

Their mom, who by the nature of still being in her mid 30s was hotter and cooler than most of their classmates' parents, had even gone and bought bottles of rum, whiskey, vodka, tequila and 3 cases of beer for the party. And though it was still illegal for most of the kids to drink, she'd said that most kids their age were already well versed in getting drunk, and that since there was nothing around their house for at least a mile, short of lighting the forest on fire, nothing major could be damaged. She'd even planned ahead and packed all their family's valuables and precious trinkets away in her room for safe keeping. Yes, Nate was quite certain that tonight was going to be a huge success, and that he may even get lucky with one of the popular girls when they see how good of a party he could throw. And while Nate wasn't a virgin, he wasn't as experienced as he would have liked to be (having only lost his V-card a couple weeks ago at prom when a nerd's cousin date had snuck him into the girl's bathroom and ridden him to a quick completion in one of the stalls).

But since nobody really knew that, he would have loved to tell the story of throwing a massive rager and having a sexy cheerleader taking him out into the field and making everyone think that their barn wasn't just for show for his first time. He'd been masturbating constantly in his free time over the past few weeks to help improve his stamina. He was now quite confident that he could at least last more than 5 minutes should he get lucky tonight.

His twin sister Natalie was just as excited as Nate was. Little did he know, but she was planning on losing her own virginity tonight, in more ways than just one. Like her brother, Natalie had been doing some prep work for tonight in the hopes of finally having sex with someone other than her teddy, Mr. Rogers. She'd popped her cherry ages ago, and had even started to steal into her mother's room and had been borrowing her anal plugs, hoping to entice cute boys with the promise of going for a full trifecta. If Natalie was being totally honest with herself, she was hoping that the sexy volleyball star Jeremy would have dumped the bitchy Shelby's flat ass and would be more than willing to give her ass a ride or two, with maybe a third load to cover her face. Nat knew that she was a sexual submissive, and the thought of having to do a cum walk for half the party and everyone to see was such a turn on that she was worried that her mother and brother could smell her excitement all day as they set up and she'd been brazen enough to go without panties.

As she was setting up the various liquor bottles, Natalie had even been tempted to open them, and slide the bottles up into herself. Watching as her classmates, bullies and even her own twin brother drank shot after shot from the bottles would have been enough to make her cum all night, but she'd resisted the urge, not wanting to do anything that might potentially upset any master or mistress that might claim her tonight. Yes, Natalie was bisexual, having long ago come to grips with these feelings, but never coming out to anyone besides her diary. Her diary was also where Nat hid all her secret, dirty, sexual fantasies that she wanted to explore. Many focused on her classmates, a couple teachers she wouldn't have minded trying to impress should they ever give her a failing grade, and sexy celebrities. But most of her diary fantasies revolved around 'them'; a man and woman that Natalie had had large crushes on since she was a little girl. She never revealed their names to even her diary, but having seen both of them either naked or nearly naked, these were her strongest fantasies, and the most vividly described. If the opportunity ever arose to submit to either of them (if not both), she wouldn't hesitate.

Nancy, their mother, was quite proud of herself and her children. Even though she'd had them when she was just 16 and had mostly raised them on her own, her twins had turned out much better than she could have ever hoped. Nate's blond hair and grey eyes were a sexy combo she knew that she would've fallen prey to when she was their age. And Natalie's well-proportioned body, as well as her long orangish red hair and blue eyes, were just as sexy. Nancy knew that both her children were planning on getting laid tonight and she wished them all the best in finding the right partner. Nancy herself wouldn't have minded if one of their sexy classmates 'accidentally' stumbled into the loft later tonight and she had a young stud to rock her world. Being a single mother hadn't left much time to date, and she was starting to get really horny.

The fact that her daughter (at least, she assumed it was Nat, she wasn't sure how she'd react if it was Nate) was taking her best toys every night for the past couple of weeks all but proved that her kids were horny and most likely wanting to lose their virginities tonight. Nancy actually wished that they would, so that when they went off to college in a couple of months, they would have at least some idea about how to have an adult relationship. That's what she needed: an adult relationship. No more Tinder hook ups that were more disappointing than they were worth, no more internet porn to masturbate to, she needed an actual relationship with a man that could fill her emotional and physical needs. And with her kids going to university come September, she knew that she could better enjoy that type of relationship in the coming months.

So it was with growing disappointment that all three realized that no one was coming to their party. Nate and Nat had told themselves for close to an hour that people were just running fashionably late. But by the time that it was nearly 9:30 when the party was supposed to start at 7, and their mother had even come out of her hiding spot in the barn loft to see why she wasn't hearing loud music and drunk teenagers, the twins had to concede that nobody was going to come. Everyone had chosen to go to Shelby's party, and while this knowledge hurt, neither of them could really fault their classmates for that. Seeing her kids' disappointed faces, Nancy decided to do something.

Not thinking about the consequences, or how technically it was illegal for her kids to drink as they were still only 18, Nancy grabbed the bottle of tequila, opened it and divided it among three solo cups. Nate and Nat were slumped on the couch in the living room as she handed them each a cup and said, "Drink."

"What is it?" they chimed in unison.

"Tequila," she said. "Now do as I tell you and drink." The twins looked to each other and shrugged before taking a couple of gulps of the pure alcohol down their throats. "Not all at once!" Nancy said in a slight panic. Watching them cough and sputter as they tried to get used to the large amount of pure alcohol, she shook her head as she added, "Serves you right for trying to kill yourselves over a failed party."

"Thanks for the concern, Mom," Nate said sarcastically.

Taking a shot worth of her own drink, Nancy glared at her son. "Hush, brat. I'm trying to make you feel better and help you forget about tonight. Unless the two of you want to continue sitting here moping about how no one came to your party."

Both twins shock their head as Nat said, "No, please help us forget, Mommy." There'd been a time for about a year or two when they were about 10, that Natalie had stopped calling her mother 'Mommy' and had started calling her 'Mom' but that had changed back once the two women had started going bra shopping together.

"Ok, but the two of you need to promise me that you can be mature about this."

Natalie nodded while Nate asked, "Mature about what?"

"We're going to play a no-holds-barred game of Truth or Dare." Seeing their skepticism, Nancy tried another tactic. "Or, since you're both too chicken for that, why don't I get out the four-person chess board and we can try to conquer each other in the most appealing game for all high schoolers, hm?"

Nate rolled his eyes while his sister said, "It's not the game Mommy, it's the company. I'd have loved to play an anything goes version of Truth or Dare tonight; but playing it with my mother and brother is just weird." Nate nodded along to his sister's explanation.

"Well, I can understand that. I certainly wouldn't have wanted to play this with my sister and parents when I was your age," Nancy said in understanding. "So how about I give you each a pass and an out. If you feel that a question or dare goes too far over the line, you can each say a simple no, or just straight up leave, no judgement or consequences. Something that I will not allow for myself. Sound fair?"

Whether the tequila was starting to impair their judgement already, or they were both secretly more eager to play this than they let on, both Nat and Nate nodded their heads to this stipulation. Nancy was about to lay out the other rules, when Nat stood up. "Don't worry, Mommy. I just thought of something. I'll be back in a moment." Prancing from the room, mother and son watched their daughter/sister leave as her skirt came dangerously close to flashing them what they didn't know was her bare ass. When she walked back in the room a minute later, Natalie was holding a sealed envelop.

"What's with the envelop?" her twin asked.

With a devious smile on her lips, Natalie turned to her mother. "Some extra spice," she said. "I'm assuming that if we don't want to answer the question or do the dare, we take a drink?" Nancy nodded that that was her idea of how the game would go. "Well then, as an incentive to play the game more, I'm adding a rule. The first person whose cup is empty, has to do the punishment sealed in this envelop."

"I'm not doing anything you've just come up with, without knowing what I'm potentially agreeing to beforehand," Nate said, knowing how devious his sister could be, if ever there was a Slytherin it was her.

"Trust me, bro," she said in a sugary sweet voice. A voice that did the exact opposite to Nate, making him even more wary. Seeing this, Nat sighed, "I won't tell you what it is, but I will tell you that it's something that I'd be willing to do, if I lost. And I know that you're much braver than I am, Nate; so, if I'm willing to do it, you should have no problem." Nat batted her eyes teasingly, truly living up to her being sorted into Slytherin.

Sighing with the resolve to not lose to his sister and ensuring that she'd have to perform her own punishment, Nate nodded. "Ok. I go first then." Both his mother and sister nodded. Hoping to throw both of them off their game, he turned to his mom and said, "Truth or Dare?"

"Truth," Nancy said, knowing that she probably wasn't ready for a dare just yet.

"Have you ever had sex with a woman, and if so, who?" Nate asked after a moment's thought.

Nat looked at her mother, wondering the same thing, as she considered answering her son's question. "Yes, I have. Her name was Hailey." Nate felt his cock twitch upon hearing this, while Nat felt a little wetness leak out of her pussy for the first time in nearly 2 hours. Turning to her daughter before either of them could ask for clarification, she asked, "Truth or Dare?"

"Truth," she said almost immediately.

"Are you a virgin, and if not when did you lose it?"

Having figured this question was going to come, Nat had prepared to answer it. "That depends on how you define being a virgin." She watched as both her mother and brother all but leaned in to sooner get the details. "I popped my cherry back when we were 15, but I haven't had anyone in my bed besides Mr. Rogers," she elaborated. Nat wanted to laugh as she watched her brother try and figure out what she meant by her last statement. Cutting off his questioning, she turned to him and asked, "Truth or Dare, bro-bro?"

Not trusting his sister to give him a dare, Nate settled for the potentially less horrific alternative. "Truth."

"Same question as Mommy asked me: are you a virgin, and if you aren't, when did you lose it?"

Nate had somewhat expected this to be asked and figured his sister was killing two birds with one stone: hoping to embarrass him into revealing he was a virgin too, as well as taking a question away from their mother. But she'd only succeed in half of that. Smiling, Nate said, "Prom was a very good night."

Both Nancy and Natalie gave a slightly shocked whistle to this, but Nate thought he saw a flicker of sadness in his sister's eyes. "Who was she, Nate? You didn't have a date to prom, so who's date did you steal?" Nat asked with a gleeful look in her eye, but again he thought he saw a hint of sadness there for a moment.

"Nice try, Nat," he replied. "But that wasn't what you asked me about. But let me ask you this: Truth or Dare?"

"Dare," she said confidently, like she was daring Nate to dare her to do something risqué and knowing that he wouldn't.

Seeing the challenge in his sister's eyes, Nate's own stare didn't falter. "Give Mom a lap dance for two minutes, no hands, but get her slightly horny."

"You sure you don't want that yourself?" Nat asked in a sultry voice. When Nate just turned on the Sir Mix-a-lot hit 'Baby Got Back', she just rolled her eyes. "Suit yourself, Nathanial," she said, using his full name. "Just don't be jerking that tiny dick of yours as you watch me grind on our mother, you pervert."

Nate made no comment as he watched his sexy sister do exactly that. He was glad his shorts were so loose that his growing erection at the sight of his sister shaking what her mama gave her for said mama wasn't as noticeable. If he'd been paying more attention to her skirt rather than her bouncing tits, Nate might have noticed that his sister had flashed their mother her bald, naked pussy. As it was, he only caught her gasp as she forced herself to look away.

Nancy was enthralled by her daughter's seductive dancing. Even after Nat had flashed her bare pussy for her own mother to see, the 34-year-old mother couldn't keep her eyes off her daughter for long. Her son's asking about her sapphic past had stirred up old memories and even older longings and Nancy was having to constantly remind herself that the sexy 18-year-old grinding her leg like a horny puppy was her own daughter.

It wasn't until the music stopped that they all noticed that Nat's dare had gone for longer than was necessary. Licking her mother's cheek, she leaned in and whisper in her mother's ear in a sexy baby voice, "Did I turn you on, Mommy?" Nancy just moaned her approval as Nat stood up and returned to her seat. As she sat, she laughed to herself as she watched her brother adjust himself. "I see you weren't the only one aroused by that, Mommy," she said as she pointed directly at Nate's crotch. She saw her mother look for a second before quickly turning away. She'd have to get her mother's inhibitions lowered if she wanted to have an even funner evening than she'd originally intended. Having intended to make her brother perform the same routine for their mother, Nat changed tactics and asked her mom, "Truth or Dare, Mommy?"

Clearly still buzzed from her lap dance, it took their mom a moment to look at Nat. Stuttering out a response, she said, "A-A-Wha-A Truth. Truth, I pick truth."

Nancy watched with slight horror as the smile spread across her daughter's face upon hearing her answer. Perhaps this had been a mistake, they were barely 2 rounds in and already this was getting out of hand. What would happen once they started drinking? She'd have to put her foot down so that nothing too over the line would happen. But she knew her daughter wouldn't stop until she was victorious. Which was why that smile on her face was so terrifying in this moment.

"What's the sluttiest thing you've ever done, Mommy?" Nat asked her mother.

Nancy knew immediately that she couldn't answer that. Hearing her say the words would cause her son to have a stroke as all the blood in his body would surge to his co-penis, it was simply his penis. Nothing appealing about a penis, even the word itself is too clinical to be sexy. But the memory of that wild night with Hailey being air tight before being the centrepiece for a bukkake that Nancy had then licked clean made her already wet pussy gush. Taking a long gulp of the tequila in the hopes that its burn would make her forget about all the thoughts in her mind, Nancy shook her head. "There's no way that I'm answering that."

Nate watched his sister's evil smile as she now had another goal for herself for the outcome of this game. He himself was also now quite curious about what slutty activities lied in his mother's past. He knew that it would be juicy if she chose to drink rather than say. Trying not to picture his mom in a 69 with her sister (his aunt) Nate barely registered his mother asking him which option he'd like.

"Stop picturing our mother in a gangbang you pervert, and answer the stupid question!" Nat said loudly, finally breaking his trance.

"I wasn-I wasn't picturing her in a gangbang!" he defended himself, before his sister's evil smile flashed and he knew that he'd revealed that he'd in fact been thinking of their mom doing something dirty. To ensure he didn't have to reveal what he'd been thinking, he said "Dare," knowing his mother would be tamer than Nat when it came to dishing out dares.

This appeared to also take his mother by surprise as she started to say something before closing her mouth again. Clearly wanting to take things down a notch, his mother said after a moment's hesitation, "For the next 10 minutes, cluck like a chicken before and after every time you speak, and if you forget, you have to take a drink."

"Booooooooooo!" Nat called from beside them, letting her feelings on the de-escalation of the naughtiness of the game be known.

Setting a timer on his phone for 10 minutes, Nate clucked like a chicken. "Easy enough. Truth or Dare, sis? Ba-gock!"

Narrowing her eyes as she tried to judge her brother's intent, Natalie thought for a moment as she considered her options. Nate had been bolder than she thought with his dare to give their mother a lap dance, and she knew that risking him asking her something naughty would be fun, if a little embarrassing. Going against her better judgement, she said, "Truth."

She knew that she should've picked dare when Nate flashed her his own evil grin. Clucking to satiate his own dare, he asked, "What's the sluttiest thing that you've ever masturbated to, sister dear? Be descriptive." He clucked again as he finished.

"I'm not sure that I want to hear this," their mother said, as Nate and Nat looked each other in the eyes, an intense staring contest.

Nat thought hard for a moment about if she should reveal this, especially to her brother and mother. But the fear of being outed, outweighed her fear of potentially losing. So, with a defeated sigh, she broke eye contact and took a gulp of her share of the tequila. Making a sour face as the alcohol slid down her throat, as well as the fact that she had now drank a third of her cup, she looked at Nate defiantly as he laughed at having made her drink. "Oooohhh! Naughty, naughty, sister!"