Sporting board is game if the girl is confident with herself

You take Molly's hand and try to make her feel more confident, but the little girl is dragging back and looks still very depressed - you know enough of bipolarity that trying to cheer them up won't work always, so you let her handle it for now. You go to the crowded living room where people are waiting and a little more chatty than you remember. The Darlington sisters are on the front again, preparing an announcement.

"So, like every year before, we are having a midnight game session!" Chels says and smirks boyishly.

"Yes, we are doing something special this year though, because everyone is an adult, we decided to call some company for the ultimate winner. It's a very expensive prostitute if you are wondering, from three states away she comes here just for this thing alone."

"Yeah, and the way this is going to happen is that we have four games and the winner of each participates in the final game, which decides the winner, alright?"

"The four games are: Monopoly, Uno, Twister and Yahtzee. So pretty common games which most of you probably know how to play."

"There are special rules in each of them, so look out!"

You are feeling kinda excited as Iris goes around everyone giving numbered notes. You get number one and assume that means Monopoly. "So, everyone gathers around people with the same number and we can start. Ones with me to the third floor, twos up on the second floor, threes stay here and fours go to the dining room with sis, let's go!"

Monopoly is one of your favorite board games and you have fond memories of losing to your family and Pearl when she visited you a few years ago. You follow Chels upstairs in the game room of the house or that's at least what it looks like with it's shelves stacked with colorful board games. There's a round table and the original Monopoly laid on it all ready. You are happy to see that Molly got selected here also, and so did Chelsie the demon, Eve the mummy and Jo the ogre. You didn't get to meet Jo properly although you did see her come in and thought that she seemed nice: "I'm March, nice to meet you." You say it all properly and feel old. She smiles and sits down: "I'm Jolyn, but call me Jo. I love your costume, what the heck?" She makes you blush and you think playing with her will be just fun.

You feel your shirt getting pulled and you freak out as it's very light fabric and could reveal your boobs if someone pulled on it too hard. "March, March? I'm just happy to see how much you care for me, so thanks. That's it." She smiles like a kid and you roll your eyes and the game starts. "Ok, so we are playing Monopoly. The rules are actually kind of hard to tell to newbies, so if anyone wants to read them then go ahead. Now, we have special community chest and chance -cards. They have real life tasks you'll have to do, or get evicted for real. Everyone here has to do them or they'll get kicked out. Let's start!" Chels announces and rolls the dice.

The game goes normal and everyone obviously buys everything as they land on the spot. Jo plays for the mummy as she can't move an inch - you feel bad for her, but can't deny the stupidity of the costume and just accept it. You are on the lead and have a good stack of properties and the most money as you just got some after passing the start. You land on a chance and read it:

"Dirty deeds. For every deed you own, you'll have to put that many fingers up your ass (maximum of five)." You'd like to laugh but something feels off, no way... "Well this got awkward quick, and I didn't write those. Sis wrote like half and Iris half, I had no part in this." Chels defends herself and Jo and Molly look at you biting their teeth. You can't believe this, push fingers up your butt, what? "D-do I have to do this?" You ask and the demon nods and you gulp: "Here?" She nods again and you start sweating and get up on shaky legs: "C-can I do it dressed?" You ask hoping for a yes and thankfully your plea was accepted. You pull your panties down a little, just so much that you have access there. You've never actually put anything there and hear it hurts, so you go easy on your first finger. It's dry and you can't really push it in that much - you think about it and grow red as you realize that licking your fingers would work, but it would make this really uncool.

You get on your knees and lube your fingers and red like a pomegranate probe your fingers up your little tight hole. It's really uncomfortable and you can't help but gasp as you penetrate yourself with the index and middle finger of each hand, spreading the little hole. You pull out too fast and your pucker paralyzes and makes your whole ass burn and your gut to let out a little fart. It hurts really much and you feel like crying and sit back down uncomfortably and the others are blushing just as much as you. "H-here. Some wet wipes." Chelsie hands you some of those and you remember that you just probed your own ass and your fingers must be filthy. You rub your hands clean and continue the game.

No one gets any special cards for a while and it starts to look as if you are winning, although you feel awful and sitting down is ****. Jo lands on your costliest property and loses. You get all her stuff and have basically won, but not before Chels moves in a community chest, she gulps and reads the card. "Oh, ehh... from you three... Molly has the best ass. That's it." She puts the card back and smiles victoriously - you hate this so much. Molly loses next and then Eve. Chels has gotten lucky and she too has some pretty intimidating properties and money gets transferred like crazy. "Hahaa! Go to jail, nice!" She whoops and goes to jail which is really good, because she doesn't have to pay you.

You see red and end up getting almost bankrupt as she chills in the jail - literal half-assed sitting mixed with bullshit like this gets even you upset and you pout as she finally gets out and gets a chance. "Ok, let's see... WHAT! No fucking way! This is fucking stupid, did I read it right?" You take the card still a bit salty and read: "Romance. Give away all your money for the prettiest girl in game and she'll give you a kiss." You don't know what to feel right now, you are the last player left and it's you who'll have to kiss her - kiss the Chelsie Darlington, no. "B-b-but isn't this... y-you'll lose pretty much..." You say and she nods and takes the card back looking at it wide eyed. "Fuck it, agh! Here, give me a little kiss." She leans in with a kind but obviously tense expression.

You are sweating, as you'd rather lose than have to kiss her. She's so beautiful and sexy and not to mention the most popular person you know. You gulp and lean in and try to do a kiss, which fails as it doesn't feel right and you just make a stupid smack sound and turn red as your lips hardly even touched. She gets a little frown and says: "Hey, do it right at least. You didn't even touch me there." She pressures you and you go slower this time and feel her lips and push deeper still to get it right - somehow it works and feels actually good. You pull back from your first proper kiss feeling hot and she smiles and stacks you all her money. "There you go wife, romance sucks huh?" You don't think so and feel kind of better as it felt kinda amazing to kiss her. You win easily and the other congratulate you and Molly hugs you and you feel absolutely amazing - even your butt starts feeling better.