Playing to Win

“What the fuck!?”

You and your girlfriends, and Brooke, react simultaneously. Celeste just gives you a knowing look, and you figured out what Celeste was trying to warn you about this game.

“As naughty as you’d like. I told you at the start, amigo.” Viv says with an evil grin on her face.

“Yeah, but based on the previous dares—” you tried to argue, but she cut you off.

“Foreplay is over, Daddy. It’s time to see how much you guys want to have free meals for life.” Viv says.

“We’re doing this for the money! What are you talking about?” Stella shouts out in her drunkenness before Cassie could shush her.

“You must be drunk, V. You don’t seriously expect me to eat out two girls in front of all of you, do you?” Tanya asks incredulously.

“For a lifetime of free meals at my restaurant? I kinda do. Do it or forfeit, T.” Viv answers jokingly to start, but her last sentence was dead serious. Cassie muffles Stella’s reaction with her hand after Stella hears Viv’s joke about the free meals prize again.

“You can dare someone to choose too?” you ask Viv.

“Dares only have to be naughty, and have to involve somebody else in the group or the one making the dare. Maximum of two other people can be involved in the dare. Everything else is fair game. I’m not breaking any rules.” Viv explains.

“There are rules?” Stella asks.

“Wait, what if Tanya’s game but we’re not?” Cassie asks.

“Then the one that’s not willing to do it has to quit, but Tanya still has to do the dare with the one that’s willing. If you’re both not willing but Tanya is, then you both quit.” Viv answers.

“That’s totally unfair! We’re not even the ones being dared!” Cassie reacts.

“You had no complaints when I was explaining the rules. The time for complaints has lapsed.” Viv calmly answers Cassie.

Stella suddenly stands up and drops trou, exposing her bare pussy to the girls, before Cassie could stop her.

“Oh my god!” Brooke reacts.

“Looks like Stella’s game.” Viv reacts. You and Celeste both stand up to help Cassie in telling Stella to pull her panties back up as there is no way you’re letting any of your girlfriends do this for the chance of winning any amount of money.

“I like having fun V, pero no soy una puta.” Tanya tells Cassie.

“So you’re forfeiting?” Viv asks.

“Obviously.” Tanya says, noticeably disappointed that she’s Viv’s first victim.

“Then we have one down. Plus one more shot for the drinkers.” Viv announces.

“I thought you were joking about calling yourself an evil lesbian.” Cassie jokes.

“Oh, the joke part about that is the lesbian part. I’m bi. The evil part I accept wholeheartedly.” Viv replies with an exaggeratedly evil laugh.

“It’s fine, chica. I’m pretty sure she’s just trying to win.” Tanya tells Cassie.

“Evil as I might be though, I must play by the rules I’ve set in previous TODDs. Here’s a rule I didn’t mention earlier. Tanya can still make it back as an active player.” Viv announces, getting Tanya’s attention.

“Tanya gets to spin next, whoever it lands on, if she makes them quit, she makes it back into the game. This comeback mechanic can only be used once per person.” Viv explains.

“Jeez. This game has a lot of rules.” Stella reacts.

“I hope it lands on you.” she says menacingly at Viv after spinning the bottle. Despite Tanya’s wishes, it lands on Cassie.

“I choose Dare.” Cassie announces.

“What? Are you sure?” Tanya asks in shock.

“Someone’s finally playing the game.” Viv says with a laugh.

“What about that makes you say she’s playing the game?” Brooke asks Viv.

“We’re playing a game?” Stella asks loudly in her unfiltered drunkenness.

“Because now I get to Dare her and somebody else.” Tanya says understanding Cassie’s chess move.

“Bingo.” Cassie reacts, offering a fist bump to Tanya who stands up and gives Cassie a long motherly kiss on the cheek instead. Tanya even sounds out the ‘MWAH!’ making Cassie giggle.

“So, what’s the dare?” Viv asks Tanya.

“Word of warning, Viv’s not going to say no to having sex in front of all of you. You’re going to have to be more creative than that.” Celeste says as a warning.

“Jesus Christ. How the fuck do you know that Celeste?” you ask your cousin.

“I can do whatever the fuck I want after a divorce. Same as you Mister-leave-me-in-his-apartment-alone-to-have-a-foursome-with-his-three-girlfriends.” Celeste quickly replies, and you realize that you’re in no room to judge your cousin.

“So you’ve played this game to the point of fucking!?” Brooke asks in shock.

“Yup.” Viv answers nonchalantly.

“I did NOT sign up for that.” Brooke replies.

“You can forfeit now and add another to the total drinks again and take Tanya’s place.” Viv suggests.

“Don’t. She’s trying to trick you into skipping Tanya’s dare.” Cassie tells Brooke.

“Clever girl.” Viv answers with a laugh.

“So what’s it going to be Tanya? I’m not going to pretend that I’m not the one you’re going to target.” Viv asks. Cassie and Tanya motions you and the others, except Viv, to huddle for a group brainstorm as to how to eliminate Viv from the game. Brooke joins you and your girlfriends, while Viv stops Celeste from joining the five of you.

“Oh no~ You know me too well. Too bad that’s a two way street. You’re not helping them.” Viv tells Celeste who sits back down.

What the hell does she have over Celeste?

“Any ideas?” Tanya asks in a whisper, so that Viv could barely hear.

“It shouldn’t involve any of us so we don’t risk getting another one of us eliminated.” Brooke suggests.

“Good point. It should just be between me and Viv.” Cassie points out.

“You guys are really determined to win this, huh?” Brooke asks them.

“At this point, I’m just motivated to get Viv out and I don’t care who wins.” Tanya answers her.

“We eliminate Viv, we can just split it five ways. That’s still a lot of money.” Brooke suggested.

“Sounds like a plan.” Tanya answers Brooke.

“What’s the plan?” Stella asks, but you all just ignore her.

“Okay, so it’s gotta be something I’m willing to do but Viv isn’t.” Cassie points out.

“Based on what Celeste said, that doesn’t leave us with a lot of options.” Brooke remarks.

“Worse for us, she’s into girls.” you tell them.

“No wonder she wanted to play this game.” Brooke says.

“Face it ladies and Junior. You can’t beat a pervert at her own perverted game.” Viv goads the five of you.

“Can you shut up for a sec?” Cassie retorts.

“Why don’t you advise Tanya to dare you to make me? Maybe you should dare me to eat Princess Ariel’s hoo-ha and she can make me quit with the smell of her—” Viv tried to joke but Brooke cut her off, “Stop being such a pain in the ass and let us think.”

“THAT’S IT!” Cassie excitedly says, letting Viv and Celeste hear her.

“This should be good.” Viv says sarcastically, not afraid of what Cassie could come up with.

“Dare me to shove something up her butt.” Cassie says, still as excited as before, but whispering now so Viv won’t know what you guys are planning. “Like the bottle, maybe? That way, I can easily do it, just in case Viv is crazy enough to accept, but I don’t think she will.” Cassie adds.

The realization of how perfect a dare for the situation isn’t lost on any of you, except Stella. You also realize something else.

“I didn’t realize how easy it would be for Viv to eliminate me.” you say with a nervous chuckle.

“I thought you liked things up your butt?” Stella asks you. You just stare at her silently, wondering what you’ve ever done in your life that would indicate to your daughter that you would. “I remember you said you liked anal!” Stella defends herself. “Also, who’s Princess Ariel?” Stella adds.

“Does everybody agree on the dare?” Tanya asks, and everyone nods except Stella.

“So? What’s the brilliant plan?” Viv asks arrogantly.

“Cassie, I dare you to shove this champagne bottle up Viv’s asshole.” Tanya declares with just as much arrogance as Viv had earlier.

“I’m going to have to call for negotiations at the risk of injury. I can’t shove an entire champagne bottle up my butthole.” Viv says calmly. Not at all the reaction you were all hoping for.

“¿Qué? No! Ew~!” Tanya reacts in horror. “Just about here, before the part it widens fully.” Tanya clarifies.

“Oh? Just up to the bottle neck?” Viv asks calmly.

“I’ll take that dare.” Viv answers confidently.

“YOU WILL!?” Your group reacts in shock.

“Points for creativity though.” your cousin, Celeste, remarks in reaction to the dare Tanya made but unsurprised at Viv’s willingness to do the dare.

“Wait, you’re game to put a bottle up your butt in front of us?” Brooke asks Viv.

“Yeah. It’s not like I haven’t had stuff up there before.” Viv answers nonchalantly.

“I think you’ve crossed the line from pervert to just plain crazy.” Brooke answers in disbelief.

“She’s bluffing.” Cassie says confidently, but Celeste shakes her head at Cassie’s assessment.

Viv starts unbuttoning her pants and you’re a bit concerned that this might actually happen now. You were all extremely sure she’d quit and retry her luck with her own dare to make one of you quit.

“Woah-woah-woah. I think we’re going way too far, don’t you think?” you quickly say before she pulls her pants down.

“I’m not the one who made the dare, Jay. Maybe you should’ve told Tanya that, don’t you think?” Viv answers you, very much having fun at the look of panic on your faces. “It would seem you thought that this would be enough to make me quit? Sorry to burst your bubble.” Viv says with an evil smile.

“My bubble hasn’t burst yet.” Cassie says defiantly. “Pants down. We don’t have all night.” Cassie adds confidently, and all three of you who brainstormed with her have a look of horror.

“You’re not serious are you?” Tanya asks Cassie.

“I’m not the one who’s going to get a bottle up her butt.” Cassie says with a serious look on her face. Viv smiles at Cassie’s determination to take her confidence down a peg.

“Ooh~ feisty. I knew you had it in you.” Viv said with a smile, before pulling her pants down to reveal a red lace thong.

“Show us that butt.” Cassie says with a serious face.

“Yes, Mistress.” Viv says submissively, like she did with Becca before.

Okay, you admit that was pretty hot. Although, the cold sweats of panic in seeing someone you want to date do something crazy kind of ruins it, or maybe it’s enhancing it. You’re not sure anymore.

Viv turns around to show all of you her bare ass cheeks, before bending down on the table to give you a glimpse of the thin fabric barely covering her rosebud.

“Your ass isn’t flat!” Stella shouts, making Viv laugh.

“Thank you, Stella! Looks like I don’t have to go to your gym after all, Brooke.” Viv says, still laughing and still bent over, waiting for Cassie to proceed with the dare.

“I’m really going to do this Viv!” Cassie shouts at her before grabbing the champagne bottle you guys have been using for the game to spin. Cassie’s hand is shaking, so you’re pretty sure she doesn’t want to go through with it either, despite saying it’s something she could do if Viv was crazy enough to accept the dare. Viv wiggles her butt to goad Cassie.

“See Brooke, it’s not flat. It jiggles!” Stella points out before slapping Viv’s ass cheek.

You and the others can’t help but give out a nervous laugh, as you all find Stella’s drunkenness endearing, but this dare is still looming in the air. Celeste approaches your drunk daughter and hugs her from behind.

“Any more of that spanking and Viv might actually fall in love with you.” Celeste jokes, before enticing Stella to dance with her to distract her. The humor of the situation brought about by Stella has lapsed, and you’re all back into an awkward silence, despite the booming music.

“Are we doing this or what? You could always just quit Cassie.” Viv goads her some more.

“I’m doing it! I’m just… I’m just building up anticipation!” Cassie halfheartedly shouts at Viv.

“Then do it already!” Viv shouts at her. Cassie approaches Viv and places a palm on her asscheek. Cassie’s taking deep breaths. She glances at you, probably looking for support; but with your brain already half-dead due to ****, you’re not much help.

“Just stuff that bottle up my asshole already!” Viv shouts just as the door to the VIP room opens.

All of you guiltily freeze in place as someone outside your group enters the room.