He does, but not everyone is so lucky

Theo stared at the dice. Two. He'd rolled 2.

Saved. For now.

He moved his token two forward to community chest, "Advance to Go. Oh my God! Bro!" He moved his piece all the way around and collected his money. Safe. He was safe.

Of course he did have to roll again. "7. That's chance. It says Go...oh. Bro. Go directly to jail."

Theo moved himself to jail and immediately found himself trapped in a latex straightjacket. He squirmed, but no matter what he wasn't getting free, "This sucks..."

"At least you can't go bankrupt." Dax pointed out.

Theo shrugged. Or tried to. It wasn't easy in the straightjacket.

Ivy picked up the dice. She was staring at defeat too. Kat's hotels were in prime real estate for her. 4, 6 or 7. She threw the dice...5. Thank God.

She moved to community chest and picked up her card, "Community Night. Each player pays you $50 to spank you." Spank? Uh oh.

Dax handed her $50 dollars and she found herself moving involuntarily, lying down across his lap.

SMACK! He brought his hand down and pain exploded in her ass.

She couldn't mop though, her body moved on it's own, lying down across Kat's lap, then Sahar, then Theo's.

Of course Theo couldn't slap her, but Dax took money from Theo and gave it to her and slapped her a second time.

Ivy sat up and rubbed her ass, glaring at her friends. Of course it wasn't their fault, but still.

At least she'd earned some money for it.

Dax looked down. 9. $9. That's all he had left. "I'm fucked..." He rolled anyway, he had ****. "5 that's..."

"Underground fight club, I'm sorry, $950." Kat finished for him.

Even if he sold and mortgaged everything he couldn't make that much. His only hope was..."How about this? In lieu of rent?" He held up his dark blue property. Nobody had sold a property for that much so far, but what other choice did he have?

Kat thought about it, then nodded. She could have squeezed even more from him, but that just felt cruel. She was getting another monopoly out of it after all.

"And um, your punishment. It says Can't back down. You will never be able to back away from a confrontation, physical or otherwise."

Dax sighed. Not that he got into confrontations a lot, but still.

"And my monopoly bonus is...Moral High ground. No matter what position you take, everyone will believe that you have the moral high ground. That's...powerful."

Afterwards Kat rolled a 9 and moved herself to Go. Sahar managed the same trick and landed right beside her.

Theo looked at the dice, but he obviously couldn't pick them up. Ivy did and put them in his mouth and let him spit them out.

"No doubles and oh...oh no..." He squirmed. He could feel it. The cold steel against his cock. A chastity cage, just like the girls last time. "Bro..."

Ivy rolled a 4 and moved to her own hair salon, then passed the dice on.

Dax's bad luck continued. A 10 put him on Theo's Sportsbook Lounge. He couldn't afford the rent, and mortgaging wouldn't do either. If he started selling houses, he was done for.

"I'll give you my railroad instead." He offered.

Theo nodded, "Sure bro. And your punishment is - Find it more difficult to resist a bet."

"That'll go great with being unable to back down..." Dax sighed.

Kat rolled, "12 that's, yes, black market." She owned it and happily skipped Ivy and Dax's properties. "Next...10, doubles again. It's chance. Go to Yakuza Headquarters. Wow, around the board in a single turn. She rolled again, and her luck ran out, "Oh no. Dairy bar, again!"

"$400," Ivy said, "And it says milk production increases to 3L/day."

Kat bit her lip to keep herself from complaining. Then she looked at her pile. She didn't have enough cash on hand. She mortgaged her utilities and paid Ivy.

Sahar rolled 10 to move to just visiting, then rolled again since it was doubles, "Yes! Community chest. Thank God! It says...Sell your underwear for $100." Instantly she felt her bra and panties vanish. Oh well, it wasn't like she was naked.

Theo rolled, with Ivy's help, and was shocked to see he made doubles. The straightjacket disappeared and he moved his piece 12 spaces to chance, "It says Take a trip on the Highway to Hell." That meant he passed Go and collected his money. "Well...you gotta spend money to make money." He took a risk and bought 3 more houses.

His bet paid off as Ivy landed on Loan Shark immediately afterwards.

"$330," Theo said, "And it says Immediate repayment - Whenever someone sexually gratifies you, you feel an immediate need to pay them back."

Ivy shrugged, that didn't seem so bad. And she had enough cash to pay him. Acutally...she had enough to buy more houses. She made it 3 on each of her reds.

Dax gulped. It wasn't looking good for him. He rolled....11. Human Trafficking Hub.

"It's only $70." Kat said.

Dax only had 9.

He had to sell houses, 4 of them, that was the only thing he could do.

Kat took his money, "And it says You are more likely to be considered suspicious."

That was rather vague, but it didn't matter much to Dax. He'd lost. There was no way back. It was just a matter of time now.

Kat rolled next and somehow managed to avoid Ivy and Sahar's properties, landing on the mortgaged Road to Ruin.

"My turn...7 that's...oh great. Ivy..." Sahar stared at her.

"Cosmetic Surgery Clinic with 3 houses? $750 please!" Ivy smiled, "And it says you get 4 cup sizes..."

"Four?" Sahar could barely get the word out before her chest exploded outwards. She was actually glad to not be wearing a bra, although she quickly realized she'd need support sooner or later. These things were massive. She looked at Kat, "Well? Do I look ok?"

Kat blushed, "Um. Ya..."

Sahar smiled, then looked down at her cards. She was $150 dollars short. She could sell 2 houses, but she needed those to make money. She bit her lip and looked at Ivy. Would she make a deal, "How about $600 and the Get Out of Jail Free Card."

"Ivy...ok." Kat made the deal.

Theo picked up the dice and prayed, "Please....bro..." He tossed it, "YES! 5. That's what I'm talking about!" He moved his token to Just Visiting.

Ivy was also lucky, rolling an 8 to land on the mortgaged road to perdition.

Dax's luck was almost unbelievable too. He went around go and got a tiny bit of money then landed on the cheapest non zero option. Highway to Hell.

"It's just $25," Theo said, "And it says more accepting of degeneracy in others."

Dax sighed in relief, "I can live with that."

Kat wasn't as lucky, "8. Hair Salon. Glad I didn't buy any houses, what do I owe you?"

"$550," Ivy said, "And it says Personal AI Trainer will assign mandatory exercise."

Kat sighed, "Well...getting in shape isn't a bad thing." She paid Ivy and passed the dice on.

Ivy quietly spent the cash on 3 more houses for her red properties. She grinned, it was looking up for her.

Sahar rolled next, "12, that's chance. Take a trip to the nearest utility. That's black market. Oh thank God, it's still mortgage. Except. I gotta roll again...2. Brothel. Good. Except..."

"3 doubles means jail." Dax warned her.

"Like I can control it," Sahar said. She picked up the dice and tossed them, "Oh no!" Doubles. Instantly she was wrapped up in a straightjacket just like Theo had been. She squirmed but of course it was no use. And to think she'd just sold her get out of jail free card.

Theo needed a miracle to get pass Sahar, Kat and Ivy. He rolled, "5 and 5, wow, Free Parking, or Underground Hideout, whatever. Ok bro, just 5 or higher..." He threw the dice again..."Oh no." A 4. Cosmetic Surgery Clinic.

"That's $925..." Ivy said slowly. She knew he didn't have the money.

Theo had little choice. He sold all of his houses and mortgaged two of his properties. It was enough, but it was clear he'd lost this game. He gritted his teeth, "What's the punishment bro?"

Ivy gulped, "B-botched penis enlargement surgery...decreased sensitivity."

"Botched?" Theo gasped, "Bro..."

Ivy shrugged, she couldn't control it. Then she rolled, landing on Kat's Yakuza Headquarters.

"$100," Kat said, "And you feel compelled to pay back anyone who does you a favour with interest."

Dax rolled next. He doubted his luck would hold.

"Sex Shop...with a Hotel. Fuck. How much?"

"$750." Sahar said.

"That's it. I'm out..." Dax could see it clearly. Selling all his houses and mortgaging his properties didn't even come close. "So I'm bankrupt...what happens now?"

They all looked at each other. Nobody knew. Then finally...