Theo wins...and loses

The pics don't seem to be working properly, but if you click links it should work.

---

Ivy immediately turned to Theo and gave him her best puppy dog eyes.

Theo smiled awkwardly, "You need something?" He asked.

"Theo, you have to help me. You're an accountant, you must be good with this sort of thing. What do I do about my credit? I'll do anything."

Theo looked at her and tried to offer a reassuring smile, "Don't worry bro. I'll help. But first..." He glanced down at his body.

"Right...um...well we don't have any men's clothes here...umm..." Ivy wasn't sure what to do. She couldn't exactly go out herself and get something.

"I'll grab him a blanket to wrap himself in. Dax, you will go to the store and buy him a new outfit. Remember, $50 per item." Kat said, taking charge of the situation.

Dax felt like protesting, who put her in charge after all, but he didn't. "Ya. I got it."

He grabbed his things and left in a hurry.

Kat grabbed a blanket and Theo wrapped himself up in it and then got to work. He went over all of Ivy's finances and immediately realized there would be no simple fix.

"I have to...go..." Kat said, "If you two don't need anything else..."

"Not at the moment." Theo said.

"We're good." Ivy agreed.

"Can I come with you?" Sahar asked. Then she saw Kat blush and realized what Kat was going to go do, "Um, nevermind. I'll go out on my own."

"Ok, see you later." Kat said as she took off.

Sahar gave Kat a few minutes head start, then followed her out.

---

Kat had never been here before, but she'd walked passed it enough times to know it was here. Sin City boasted about being the largest adult boutique in the city and as soon as she entered she could see why. She felt totally overwhelmed. What was she even supposed to do here?

"Hi, can I help you find something?" The saleswoman asked as Kat walked by.

"Oh...um...well..." Kat blushed. She felt so awkward being here, "Um...to be honest...I need to spend $500 here."

The woman raised an eyebrow, "That's a bit of change. You aren't looking for anything particular, just to meet that target?"

"That's right." Kat admitted.

"This some kind of dare?"

Kat blushed, "Well...sort of. I...I don't even know where to begin."

The woman grinned, "I'd love to have $500 to spend on our merch. Why don't I do you a favour and be your personal shopper? I'll get you as close to that threshold as possible, you just leave it all to me."

"Really? Um, wow. Yes. Please. Thank you. Oh, and not under $500, just over is better." Kat said.

"You got it. Do you want to wait here or follow me around?"

"Umm..." Kat looked around and was immediately overwhelmed by the sheer size of the place.

"You can wait here, then it'll be a surprise." The woman winked at her.

Kat waited as the woman walked around picking things out. It took surprisingly little time for her to return. She supposed $500 wasn't as much as she thought it was.

The woman set her purchases down on the counter, "Shall I show you what I picked out?"

Kat nodded.

"Alright. First, this is our most popular dildo. Every girl needs one of these. Suction cup base, just 6", very average. Nothing too crazy right? It's 39.99. Next a vibrator, to bring things to the next level. This is a bit pricier, 160, but it's worth it. Remote controlled by app, I'm sure you can think of lots of possibilities, can't you?"

Kat gulped. Could she? No, she wasn't planning on using this stuff. She just had to spend the money.

"Next I thought you might enjoy trying some beginning bondage. Nothing crazy, but trust me, the loss of control...it's powerful. This is a collar-to-cuff combo. It's very soft, fabric cuffs, just 44 dollars. And this harness, there's no much too it but it's oh so sexy. Also a cheap blindfold and ball gag for 45 dollars."

"If you are feeling a bit bolder, nipple clamps. Trust me, they look scary but they really enhance the pleasure. Just $30 for these. Oh and this...now not everyone is into chastity play but trust me, there's a lot of fun to be had. This beginning one is easy to wear, only $60. And finally...I just eyeballed it but I picked out some lingerie for you. Do you want to try them on?" The woman held up several extremely skimpy outfits.

"N-no. That's fine."

The woman nodded, "Alright. Then your total is...502.47. Not bad eh?"

Kat smiled, "Yes...thank you so much..." Suddenly she felt like she REALLY had to pay her back, "How can I pay you back for helping me?"

"Pardon? I mean...you are paying for the stuff..."

"Ya but you really helped me. Please, there must be something I can do for you."

The woman hesitated, then somehow found the courage to ask, "Y-you could try something on?" She asked, pointing to the pile of clothing.

Normally Kat would have refused, but she felt compelled to repay the favour, "Y-yes. I will."

And so Kat found herself in the changing room pulling on wispy strips of leather. She couldn't believe she was wearing this, let alone that she was about to step out of the change room and let someone see her. Sure it covered her nipples, barely, but she was pretty sure a sneeze would set them free. She took a deep breath. She owed this woman, she HAD to do this.

She stepped out, "W-well...what do you think?"

The saleswoman gasped, "Oh my God! You are stunning! You're boy...girlfriend? She'll love it."

Kat blushed, "T-thanks...I'll go change back."

She felt the compulsion fade. She'd repaid the favour, it was over. She changed back into her regular clothes, paid for everything, and hurried out of there.

---

Sahar knew she had to flash 8 strangers, but she had no idea how to go about it. The game would obviously punish her if she failed, but would it protect her if she got in trouble?

Probably not.

That meant she couldn't just walk down main street topless. Not that she'd considered that to be an option anyway.

She decided she needed to go somewhere she wouldn't be recognized, wouldn't be filmed, and wouldn't get in trouble with the law.

She decided on the perfect place.

Sahar took the bus to the edge of town. She'd come to a gym that offered free trials, having borrowed a workout outfit from Ivy before leaving. It only took a few minutes to sign up and she was granted access to the change room.

Thankfully she was not alone.

She took a deep breath, then pulled her shirt over her head.

She stood there topless and waited.

The other women in the change room paid her no attention. None at all.

Wait...did this count?

She turned and briefly made eye contact with another woman. Eye contact. She didn't even look down.

Sahar didn't know what to do. She finished changing and went into the gym.

She hadn't actually intended to work out, but she was here now and didn't want to make it look like she was some kind of creep.

She was also a little curious about her perks. How minor was the minor strength boost?

She didn't really have a baseline for her strength. She hadn't been weight training before the game or anything. But she figured she was probably on the low end before. She saw a woman get off a chest press machine and wipe it down. Sahar decided to try that.

The woman had been pressing 40 lbs. Sahar sat down, gripped the handles, and pushed.

Wow. It felt super light. She set the weight down and immediately doubled it. 80 lbs felt more like it, but she was still able to do 10 reps without hitting her limit.

She finished her set and got up, feeling pretty good about herself.

Then a man sat down, moved the pin to 200 lbs, and cranked out 10 reps without breaking a sweat.

Right...it was only a minor boost after all.

He finished and set the weight down, clearly intended to rest between sets.

Sahar didn't know why, but she suddenly pulled up her sports bra and shirt, exposing her bare breasts.

He looked.

Of course he looked.

No, he didn't just look. He stared.

1...2...3...

Sahar counted in her head.

9...10...She covered herself up, then immediately fled the scene.

She couldn't believe she'd just done that. She'd exposed herself. In public. To a man!

She didn't even bother to change, she grabbed her stuff and ran. She kept looking over her shoulder, expecting security to chase her down, but nobody came.

Once she was far enough away she relaxed a little. 1 down. 7 to go.

She realized that as much as she'd prefer to show her boobs to women, if she wanted to get them to look for 10 seconds she'd be better off flashing men. They'd be less likely to call the cops too.

She sighed. She wasn't looking forward to this.

---

Dax returned to the apartment with a suit for Theo. He'd bought home for himself too. "Suit up, I have an idea!"

Theo looked at the suit, then nodded, "I will...but your ideas make me nervous bro."

He wrapped the blanket around himself and scurried to the bedroom to change.

Dax sat down beside Ivy, "So...quite the getup you have there."

Ivy rolled her eyes, "Ya. Thanks for reminding me."

Dax grinned, "You're uncomfortable wearing that aren't you? Why don't you take it off. I don't mind," Dax licked his lips, "I could even..."

"What? Ew! No!" Ivy said, "Why would you..." She paused. Right. Brothel. Everyone assumes she's open to their advances. Even Dax. Fuck. "I guess I'll be the asshole if I get mad at you. Sorry, you'll have to find someone else to seduce."

Dax shrugged, "I plan on it," Theo walked out of the room dressed in his suit, "Bro, looking good. Ok, so here's the plan. You and me, we hit the Casino."

"Casino? How is that a plan exactly?" Theo asked.

"You have good gambling odds. I'm amazing at calculations now. We go and earn money to help Ivy out of debt and find some chicks to take back home as a bonus." Dax said.

"That's..." Theo paused, "Wait. That's not a bad idea. Even with canceling cards and trying chargebacks...Ivy is still screwed."

"Hey!" Ivy says, "Wait, you guys would help me like that?"

Theo smiles at her, "Ya bro, we're friends."

"Oh my God, if you can get me out of this mess I'd suck your cock." Ivy said.

"Ok." Theo said immediately.

Ivy opened her mouth, then stopped. Wait...did she just make a promise? She'd been mostly joking but now she felt like she'd really do it if he pulled it off, "Um...you two should go then."

"Right, let's go." Dax said.

"Wait, I need to call Kat first. I need her permission."

"Ok...but hurry up. I want to get there soon." Dax said.

---

Theo stared at the table, then made his decision, "$1000 on 31."

Someone at the table whistled. For this small casino it was a relatively large bet for a single number.

Theo felt confident. He'd just knew this was his number.

The ball started to bounce.

Theo waited. And waited. And waited.

"And the winner is....31."

Theo whooped in delight! $35,000. He'd just won $35,000.

That brought his total winnings to nearly $50,000 on the night. He couldn't believe it.

With this kind of success he could quit his job and become a full time gambler. It sounded risky to her accountant mind, but with results like this...

"Excuse me," Theo turned and saw an absolutely gorgeous woman standing there, "I couldn't help but notice you're on quite the streak. You should really step away now."

"Huh, why?" He asked.

"Casino's don't like to lose. Soon they'll kick you out. Maybe even ban you."

"But I'm not cheating. It's just luck."

She shrugged, "Doesn't matter. Why don't you have a drink with me while things cool off? I'm Ciara by the way." She extends her hand.

Theo shakes it, "Theo. Nice to meet you."

Theo spent the next hour talking to Ciara. He found the conversation flowing naturally and he was having a great time. Dax had gone off early with so woman so he didn't have anything else to do. It was nice to just sit and talk to a beautiful woman.

"So Theo..." Ciara said with a sly smile, "Do you want to get out of here?"

Theo gulped, "Y-yeah bro. I do."

She stood up and put some cash down for their bill. Theo felt like he should pay, he'd just won a bunch, but she insisted.

They headed towards the door.

Her phone rang.

"Sorry, it's my sister..." She answered the phone, "What? Those bastards. But you need that medicine! What are we going to do? No, you can't do that. I'll come visit you now, you shouldn't have to suffer alone. Yes. I love you too. Bye," She hangs up and looks at Theo with a sad smile, "I'm so sorry. I have to bail. My sister...nevermind. We just met. I won't burden you with my troubles."

"No, it's fine. Tell me. What happened? She needs medicine?" Theo says.

"Yes. Her insurance won't pay. It's experimental still, but it's the only hope she has. I'm not sure what I'm going to do. I already maxed out a second credit card...I shouldn't have even come here. I was just so despite."

He sees a tear form in the corner of her eye. He can't help himself. He wipes it away, "How much?"

"What?" She asks, "No. I can't ask you. We just met."

"How much is it?" Theo asks again.

"$4500." She says.

Theo nods, "Let me. Please."

She shakes her head, "No. That's your winnings. We don't even know each other."

"Exactly. It's my winnings, so I can do what I want with it." He takes no more arguments as he cashes out and hands her the money, "Here. This is $9000. She'll probably need more than one dose, won't she?"

"Theo...you're my savior. Here...take my number. I have to go see my sister but I promise I'll pay you back when I can."

Theo smiles, 'Don't worry about it bro." But he does take her number. He'd love to go on a real date with her.

She smiles and says goodbye.

Theo heads back towards the bar and spies Dax coming out of the bathroom, "Bro!"

Dax smiles, "Hey. Saw you talking to that hottie. You get lucky?"

"No, she had to run. What about you?"

"Oh I'm doing quite well. Quite well indeed," Dax grinned, "But I need to borrow some money."

"What? Why?" Theo asked.

"Well I tipped the bathroom attendant $5000 to keep everyone else out while we...you know...anyway I'm all out of money."

Theo sighed, "Well maybe we should call it a night. I'm still up, but if I spend any more I won't have enough to help Ivy."

"Aw, you are the least fun person ever!" Dax shakes his head, "Just give me $1000. I bought that suit for you after all."

Theo sighs, "Fine. Here bro. But I'm heading home."

"Ok. See you tomorrow." Dax heads back into the casino to find someone else to hit on.

Theo sighs and calls Kat to inform her he's heading home. He feels good about himself, completely unaware that he's just been scammed.

---

Ivy was bored. She could barely move. She was uncomfortable. Everyone else had left.

"Ugh." She moaned.

She flipped off the tv. There was nothing to watch anyway.

She stood up and started the slow process of dragging the ball to the kitchen to get something to eat.

Then the door opened and Sahar rushed in.

She slammed the door behind her, "Whew!"

"Uh...what happened?" Ivy asked.

Sahar walked over to her, "I had a little wardrobe malfunction in the lobby. Too bad I'd already flashed all those guys. Anyway I ran all the way up the stairs hoping they didn't follow me."

"Oh, that sucks. Wait, so yo flashed 8 people already?"

"Not 8, but I'm almost done. It was terrifying, but somehow it got easier the more I did it." Sahar admitted.

Sahar suddenly reached out and touched Ivy's chest through the jumpsuit, "They seemed to appreciate it. Although my boobs aren't as nice as yours."

"Please, guys just like boobs. All boobs." Ivy said.

"Wanna bet?" Sahar said, a glimmer of mischief in her eye.

"Yes." Ivy said immediately.

"Ok. How about this...we go and flash a neighbour and ask them to rate our boobs. If they like your bigger boobs better, I win. If they like mine better, I win."

Ivy hesitated, "Flash a neighbour?"

"If I win, you let me play with your bare boobs for...10 minutes. I can already grope them, but I want full access." Sahar said.

Ivy raised an eyebrow. Sahar wanted that? She wanted to say no, but it was a bet. She felt like she couldn't say no.

"F-fine. And if I win...you help me move my ball and chain whenever I need to."

"Deal." Sahar said immediately.

Bet made the two of them went into the hall. Ivy didn't want to flash any of her neighbours, but she knew that Henrik and Daniel would be cool with it. They knocked and waited.

Henrik answer, "Hel-oh! Um, Ivy what's with the getup?"

"Nevermind that," She said, "We want your help settling an argument."

"...Sure...how can I help?"

Ivy looked at Sahar, "R-ready?"

Sahar nodded and grabbed the bottom of her shirt.

Ivy sighed, then undid the last button holding her suit together, "Now." They both flashed him. His mouth dropped open. "Whose boobs do you like better?" Ivy asked.

It only took him a moment to decide, "Yours." He said to Ivy.

"See?" Sahar said, "I win."

They covered themselves again, "Thanks...I guess." Ivy said to Henrik. They hurried back to the apartment.

Sahar looked at Ivy hungrily, "Ok. Show me your boobs!"

Sahar immediately went to down, groping and sucking and kissing Ivy's breasts. Ivy stood there awkwardly. She was feeling rather aroused, which was unusual, but it was more awkward than anything for her.

Even more awkward was when the door suddenly opened and Kat walked in.

Sahar stopped immediately and looked at Kat, "K-Kat! I can explain!"

Kat blushed and looked away, "No. It's ok. You're both adults. Um. Excuse me."

Kat hurried off to her bedroom.

"Darn it. Why...why did I do this?" Sahar asked herself. Was this a 'minor' tendency to sin? What was wrong with her.

"Sorry Ivy," Sahar said, "Let me help you with your chain anyway. I'm sorry."

"No. A bet's a bet. But I do appreciate the help." Ivy said.

Eventually Sahar helped Ivy get the chain into bed with her. Ivy eventually drifted off to sleep, more confused than ever.