Shopping trip!

To Weiss and Yang's credit, they were not lying about going shopping. They'd taken their partners clothes shopping before the day's real fun would begin. It had started vanilla enough. They'd left the last clothes store with a few nice sundresses, and some other needed accessories. Yang and Weiss, clearly itching to start the fun stuff, dragged their team into a lingerie store.

"Do we really need this stuff?" Ruby complained.

"Are you really going to say no to Weiss spending a ton of her daddy's money on free sexy underwear?" Yang teased.

"W-Well no. That's not my problem anyway! The problem is that I know you two will make us pose in whatever we end up in!" Ruby elaborated on her annoyance.

"You love every photo we take and you know it!" Weiss reminded her.

"It's the principle, Weiss!" Ruby gently blushed at the reminder of the photo shoot, and her exhibitionist tendencies.

The girls had finally arrived to the section that the winners planned on. It featured relatively tasteful underwear. It was clearly high end, but the pieces couldn't be described as 'barely there'. The pairs split up, with Yang and Blake trending towards the more risque side. Ruby was immediately drawn to a two piece-set; featuring crimson and roses as its main draw. The lingerie also had plenty of frills, and a garter belt, that Ruby would probably never admit to adoring. She immediately ran and took it off the rack, and held it up for inspection.

"Oh! This is exactly my size! Can I be done now?" Ruby begged. Partially because it would excuse her from the rest of the store, but also because she was genuinely excited about it. Weiss could hardly say no to that; still, she had appearances to maintain after all.

"Hmmm... Hold it up for me, Ruby." Ruby did just that, holding the piece against her chest. Weiss took up the critiquing eye that wouldn't look strange on a fashion show judge. She took her time taking in her partner from every angle. She exaggerated the motions even further, holding up her hands like she was framing the perfect shot; as if to make Ruby her masterpiece.

"I do see the appeal, but what do you want lingerie for? You won't be wearing it, or anything else in the dorm room for that matter." Weiss couldn't resist the opportunity to remind the reaper of her punishment.

"T-That may be true!" Ruby drew in closer, "But think about... the special occasions. How else am I supposed show you my... appreciation?" Ruby questioned. Weiss took up a thoughtful look. Inside, she was deeply grateful for Ruby. She loved the smile she'd taken up since the conversation had started.

"On your knees?" Weiss said cheekily.

"Do you really want me kneeling to be limited to special occasions?"

Weiss's eyes went wide and she rapidly shook her head. "You make a fair argument. Still though... I need a little more. How about you try it on for me?" Weiss couldn't see herself denying Ruby Rose in 1000 lifetimes, much less today. That didn't mean she couldn't draw some more enjoyment out of the situation though.

Ruby beamed and begin turning to make her way to the dressing rooms before Weiss stopped her. The heiress made a show of looking around. Besides RWBY and the lone cashier, the store was completely empty.

"Dressing rooms have such horrible lighting, don't you think?" Weiss said, offering Ruby a choice. She could go to the dressing room and try it on normally. Or... she could strip naked right in the center of the store and then try it on. Ruby clearly was itching for some fun.

"You know... I think you're right Weiss. Can you hold my cloak for me?"

"Certainly." Weiss said with a smile. She took Ruby's cloak into her arms. It was the most important part of Ruby's outfit for a reason, and it certainly deserved better than the floor.

Ruby had recently grown tremendously more confident in herself. That newfound confidence made her even more daring, as she gave Weiss bedroom eyes before slowly backing up. Once she had enough space around her, she began stripping out of her top. Before no time, her dark top laid on the floor, leaving the team leader in a bra, skirt, thigh highs, and presumably panties. Before long, she stood in just a bra and underwear.

She took a deep breath in, before unclipping her bra. It fell unceremoniously to the floor, joining the rest of her outfit. Her outfit had officially become indecent, as she stood in a public place where anyone could see her. She looked Weiss dead in the eyes as she hooked her thumbs into her waistband. Her smirk was inticing as she drew her panties to her mid thigh, before releasing them. Gravity took over from there, and Weiss was lucky enough to take in her perfect form.

Ruby decided to hide the end result a bit, she turned around as she dressed, giving Weiss an amazing view of her toned rear. Ruby further drew attention to her ass with an almost innocent shaking. A few tantalizing minutes later and Ruby fully donned the lingerie.

She turned around and Weiss couldn't help but draw breath. Ruby had good taste, the lingerie took the huntress beyond a 10/10. Ruby flushed innocently at the stare Weiss had adopted.

"Did I pick a winner or what?" and Weiss could only nod. She picked up her partners clothing and **** her into the nearest changing stall possessively.

Later in the day, team RWBY arrived back in their dorm with their newest purchases. Each of the girls had bought a set of lingerie that suited their styles and colors.

The most interesting purchases didn't come from the lingerie store however. Inside a bag purchased from an adult store was 3 vibrators, which would all hook up to a single remote. They were subtle enough to not be noticeable through clothes. That might be a problem later though, if the 3 bet losers had too much fun, and lost their panties too. Glynda wouldn't be able to catch them about the dress code, but she certainly would give them off-the-record hell for wearing vibrators to class.

"So... We're really doing this, huh?" Yang asked. Despite being the only one who wouldn't have to participate in the challenge, Weiss felt like she'd be out of place to speak about. This was a dare made on a lighthearted bet after all; she wouldn't ever make her teammates do something they weren't comfortable with, bet or no bet.

"You guys really don't have to. You could also just not strip during it. Would that make you feel better?" Weiss said in a caring tone. She really wanted her teammates to go through with it though.

"No! We aren't backing out of this Yang! We made our bets and lost them! Now we suffer the consequences of them! We're wearing those toys to class and stripping every time they make us orgasm! That's final!" Ruby had apparently had enough of her sister's nervousness. Blake drew closer to Ruby in support.

"She's right Yang. We shook on it, and we lost! We don't have a choice in the matter!" Blake spoke.

Yang flushed but nodded. "Fine! But we set the rules now!"

"That's fair enough. Here's the rules I was thinking... Also, Ruby, aren't you supposed to be getting naked?" Blake spoke. Ruby paled at her forgetfulness and quickly stripped off.

"Since Weiss is the 'winner' in all this, she gets to hold onto the remote. Every time you orgasm, you have to immediately take off an item of clothing once you settle down, unless it happens mid-fight or quiz. We'll all wear the same outfit: Jacket, Vest, Blouse, Bra, and Underwear. You can wear the thigh highs but they don't count. Same with shoes. If you were counting, that means you basically get 2 freebies before you're showing skin. If you go commando you can get away with 3."

Blake paused to let that sink in, before she continued, "If you start to get oversensitive, you can take one 20 minute break. If you forfeit the challenge, the rest of us get to decide another punishment for you. I'm not sure it'd be smart to give up. The challenge starts at 8:30am breakfast, and only ends when we get back to the dorm at 3pm."

Essentially, they'd have to sit through 6 and a half hours of buzzing:

A 30 minute Breakfast, then History, Dust chemistry, Lunch, Port's Grimmoire, than the one and a half hour long combat class. They also had 10 minutes between each class, accounting for the missing time. If they couldn't last more than an hour per orgasm, they were in real trouble real quick.

"What happens if we cum after we're naked?" Ruby asked, putting on a confident tone.

"Nothing. The whole class will already see you naked and orgasming, why would I punish you further?" Weiss asked, leaving no room for debate.

"Aww that's no fun!" Ruby complained lightly.

"Besides Ruby, there's no way you're going to cum 6 times in one day! Even with huntress stamina!" Yang said.

"You almost make it sound like a challenge Yang. Is this sounding too easy for you?"

"Obviously not! I'm terrified! But realistically, we probably won't even end up more than indecent!"

"Yang does have a point. It does sound kind of boring if none of us end up naked... Ruby and Yang, how about we make a bet among ourselves?"

"Like?" Ruby asked, as Yang regretted chiming in.

"Whoever orgasms the most through the day, strips completely naked in the arena after their spar in combat class. That counter will stop whenever one of us gets drawn to fight, but the rest of the bet continues on."

"Oooo that sounds interesting. What else do they have to do?"

"How about... if they win the fight, they have to invite the person they beat to meet them in the Beacon courtyard, so that our loser can get on their knees and 'apologize' for beating them. If the other person wins though, they still get invited, but they get to choose their reward. Sound good?" Blake said deviously.

"Sounds more like a mouthful." Said Yang, but didn't reject the idea.

"Deal. But the loser has to streak to the courtyard, for old times sake of course." Ruby agreed.

Weiss couldn't believe her teammates were digging themselves deeper holes, but she couldn't complain. She was heavily benefiting, after all. She just couldn't wait for the school day to begin.

Authors note: If you have a preference, comment who'd you'd like to lose, who you'd like them to lose to, and what challenge they have to do.

Also, comment how you exposed you want each girl, I'd love some feedback