Winter Holiday Contest 2022: Caro’s bet gone wrong

[Darky]

Caro is a good looking 19 year old girl. She is blessed with a beautiful bunch of dark curls. Green eyes, which gives her something mysterious. Caro is gullible and impulsive. Doesn't get into trouble often but when she gets into trouble it's also firm. In addition, she is also a party animal. Always up for a joke or a bet. All her friends know that and like to use or abuse it.
What shall we do today?" Caro asked Hannah.
"We've got the whole day to ourselves now that the Christmas break has started. Let's go to the mall and see if there's anything going on."

And so Caro and Hannah headed for the mall. On the way, she chatted small talk until they met Damian. "Hey Damian, are you coming to the mall too?" cried Hannah. "No sense" was his answer. "Ah please. It's going to be fun," Caro begged "Hmz, well come on then, but then you treat me to a coffee." "Deal!" said Hannah. And so the trio set off. After fifteen minutes she reached the coffee shop in the shopping center. Caro ordered a coffee and two hot chocolates. With the tray in her hands, she walked over to the table where Hannah and Damian were already waiting, or so she thought. "Where's Hannah?" she asked Damian. "No idea." grinned Damian.
Then Caro felt two hands on her hips and a firm tug on her pants. Then she heard Hannah laughing. "Just kidding!!!" she shrieked. "Too bad for you that you didn't manage to get me pantsed.” She quickly put down the tray and pulled her pants back up. "No one has ever succeeded. My trousers are always well fastened." "Interesting," Damian replied. "Do you think I can do it?" "Oh boy! What are you doing? Of course I will. How do you envision that?"
"We hang out together all day. I'll try to pants you. If I succeed before we break up I'll get your pants until we break up otherwise you win and I'll do what you want for a day. But if I succeed besides losing your pants, is that your destiny too. Deal?" "That's good Damian, prepare yourself to be a slave for a day." said Caro confidently. That said, the three continued shopping. They walked from one store to another. Shop in, shop out. "Strange," thought Caro, "he doesn't make any attempt to win. Well, he must." Suddenly, Hannah stops at a clothing store. "Shall we go inside?" she winks at Damian. "Oh yes why not." was his answer. The girls roam all the racks, while Damian walks 'cozily'.
"Oh Caro, those are cool pants. Really something for you. You have to try them on." "Indeed, those are nice pants. Come with me to the fitting room." Hannah gives Damian two thumbs up and nods at him. He understands her sign. Caro came out of the fitting room on her socks. "Those pants are really good, do you think Hannah?" "Oh sure. It looks good on you."
Caro sees too late that Hannah is looking past her. And then it hits her... too late. She feels a cold breeze on her thighs. Then she looks down and sees the pants on her feet. In a flash, Damian has pulled him down. She hears him and Hannah laughing and giving each other a high five. "Shit Caro, did someone manage to pantsed you." "You bastards, you agreed, didn't you?" Hannah looked at her mischievously, "Yes, just like you often trick me."
"Um ladies," said Damian, "I think I won a pair of pants and a slave." While holding up Caro's own pants. "Will you come to my house tomorrow morning at 8 am. Caro to make up for her loss and Hannah, you for the checkup?" "I have no choice I'm afraid." said Caro, "I'm so glad I chose boy shorts instead of a thong today."

The next morning, Caro and Hannah ring Damian's doorbell at 8 am.
"Good morning ladies. As you know my mother doesn't want shoes in the house so you can take off your shoes. Ohw and Caro, you can take off your pants too. You lost that right yesterday." Growling, Caro takes off her shoes and pants. Dressed only in a t-shirt, underpants and her ankle socks, she walks in with the others. Where they are greeted by Tom, Damian's 14-year old brother. "I thought there wouldn't be anyone but the three of us." said Caro. "I never said that."
"Why aren't you wearing any pants?" asked Tom. "Because she lost a bet and now she's my slave for a day little brother" Damian laughed. "Oh and has she been naughty, Damian?" "Yes, Caro has been very naughty. And what happens to naughty children?"
"I know....naughty kids get spanked or have to stand in the corner with their hands on their heads." "Exactly boy, that's what happens to naughty kids." Caro swallowed at the discussion between the brothers, while Hannah took it all in amusement. "That will be red buttocks Caro" she laughed.
"Would you like to give Hannah a spanking first?" Damian asked. "No, why don't we give Tom that credit?" Caro froze, a younger person spanking her, that was not possible. "Maybe that's not such a bad idea. Tom, credit to you!" Tom was only too happy to accept this. He sat down on a chair and Damian and Hannah laid Caro across his lap. "Buttocks up, otherwise it will get worse." Caro sighed and did as told. Tom meanwhile had the time of his life and gave Caro a few good slaps on her buttocks.
"Okay enough," Damian said, "Caro just stand in the corner with your hands on your head until we know what else we're going to do with you. After all, we've got all day." Caro stood in the corner of the room, facing the wall and hands on her head. This caused her shirt to creep up, exposing her underpants to everyone in the room.

"Tom, why don't you invite a friend or two?" "Is that allowed? Oh they'll like this!" "Nooo," cried Caro, and turned around. "Stop you, one more time and you lose the privilege of your shirt." said Damian sternly. Horrified, Caro turned around again. Tom came in shortly after with Frank, one of his best friends. "See I have an almost naked girl at home!" "Wow you were right. Can I touch her?" Damian looked doubtful, "Of course you can."
Frank didn't let himself be told that twice. He walked over to Caro and stroked her legs with his fingertips. Caro started stepping on this to avoid his fingers. "Is anyone ticklish?" grinned Damian. "Yes she sure is" Hannah replied. Tom and Frank took this as an invitation to continue tickling her legs. Caro kept kicking but against two pairs of hands she had no chance.
The boys had a lot of fun tickling Caro. Frank, who was bolder than Tom, dared to tickle Caro's side. Caro slid her hands off her head in shock. "Okay Caro," said Damian, "apparently a simple assignment is too difficult for Hannah. What's her punishment?" "Huh, should I remember that? Well, you already warned her, so take her shirt off." "Good point Hannah! Tom, Frank, will you help Caro out of her shirt?" Caro turned white, two younger guys taking off her shirt?
The boys wrestled Caro out of her shirt. Now dressed only in her underwear and ankle socks, she knew she had no chance against this tickle torture. "Actually, it's nice to give Caro a tickle torture with the four of us." suggested Damian. Carol shook her head. "No, no please don't."

Hannah also nodded in agreement. "Good idea." And so four pairs of hands attacked her almost naked body. Hannah and Damian concentrated on her lower legs, knees and thighs. While Tom and Frank take care of her sides and armpits. Caro screamed and tried to drop to the floor so she could curl up into a ball for protection. After a few attempts, Caro managed to drop and roll up. Hannah and Damian stopped tickling and let Tom and Frank continue. Tom had taken his brother's place and was tickling her knees. Frank continued to work on Caro's upper body.
Suddenly Caro felt her bra fastener being tampered with. "No stop!" Caro yelled out, "Damian, Hannah do something. He's trying to undo my bra."
Hannah and Damian had no idea of ​​helping Caro. "Come on Caro," said Hannah, "don't be a spoilsport. He's a kid, what can he do?" "He's trying to open my bra, I'm telling you!" Hannah looked at Damian and said, "Maybe I should help." Caro, meanwhile, was fighting for her bra while Tom continued to tickle her. An unfair battle, which was about to get even more unfair. Because of the struggle, Caro's left bra strap had already slipped off her shoulder and she had to make every effort not to let her breast fall out of the cup. Out of the corner of her eye she saw Hannah coming towards them. "Oh fine, help." she thought. To Caro's surprise, and the boys', Hannah sent Tom to Frank: "Help him." Caro looked questioningly at Hannah. Without batting an eyelid Hannah grabbed the waistband of her panties and pulled it up hard, Caro got a giant wedgie. This weakened the grip on her bra. Tom and Frank took the hint and together they undid the bra. Caro was now forced to fight on two fronts. Keeping her bra and getting off her wedgie.
Damian looked at it with a smile. With good teamwork, the boys managed to get Caro's left arm out of the bra strap. Caro was in two minds whether to give up her bra or her panties. When she protected her bra, Hannah pulled harder on her panties. She protected her panties, the boys attacked her bra. This war of attrition was too much for Caro. "Okay, okay you win. I want my underwear to last longer, and you're tearing it apart. Take what you want." The tug of war between Caro's bra and briefs had resulted in a stretched elastic of the panties and a tear in the bra straps.
"Actually, we don't want anything right now. Go stand in the corner again. Hands on your head and don't adjust your clothes. Leave it as it is." said Damian.

Caro sighed, stood up and stood in the corner. Her back was now exposed because the bra was unfastened. The elastic of her panties stretched, exposing her butt crack. Caro was even more embarrassed. "Okay Caro, I've thought about what I want next. You get a chance to buy off the rest of the day, get dressed and go home or stay, the latter is up to you.""What should I do?" asked Caro, amazed at Damian's quick give up to have her all day the way he wanted.
"Simple, you stay dressed as you are. Bra undone, panties, socks. The four of us are going to try to get your last pieces of clothing. If we can't do that within half an hour, you're free. Can we do it? Then there are other consequences. Agreed?" "I don't really feel like this. Because do I have a chance against four? But if I don't do it, I also lose. So yes, I'm in."

The four gathered in a circle to devise a plan to strip Caro of her clothes as quickly as possible. "Okay," said Damian, "here's the plan. Hannah's tactics worked well before. I suggest Tom and Frank go for her panties, that's the easiest. Hannah and I go for the bra. Her socks as long as if possible, if she has lost her underwear, she will give it up She will want to protect her dignity as long as possible In the extreme case when the time comes over 20 minutes, go for the socks and tickle the soles of her feet. " The other three nodded. Damian set a clock for 30 minutes. "Ready for, maybe, the final fight Caro?"
Caro nodded, ready to fight one last fight. All or nothing, literally. Damian's plan didn't stand a chance, of course, but she wouldn't give up without a fight. Within seconds she was already surrounded by the four. Caro decided to have more grip on the situation, to fall on her stomach. Then they had to use force to pull out what remained of her clothing from under her. And so the fight began. As agreed, Frank and Tom went for her panties. Frank pulled left, Tom right, and Caro pulled every side she could to apprehend him. Hannah and Damian would take turns tugging at her bra. Haanah started pulling on the straps, forcing Caro to protect her bra, leaving her panties vulnerable again. And vice versa. Even Caro seemed to have fun with this game because she could resist enough.
The clock was ticking in Caro's favor. She was still able to keep her hands off her and thus keep her underwear on. Damian looked at the clock and signaled the boys. "Okay Caro, last 10 minutes, hold on!" he grinned. At that moment, Caro felt something she hadn't felt in the entire battle. Someone tugged at her left sock, which was slowly pulled out. The same thing happened with her right sock. Two bare feet in front of Tom, ready to be tickled. Tom gently stroked the sole of Caro's foot with his nail. Caro, meanwhile, gritted her teeth to keep from laughing. Tom quickened his movement. Caro couldn't hold it anymore because the lashing at her underwear also continued. Because of Caro's trashing and kicking, Frank had free reign with her panties, which he pulled down and out quite quickly and easily. Bare from her waist, Caro could only save her bra, but now with three pairs of hands to get it off, she had no chance. "Stop the clock, Caro is naked." said Hannah, swinging the bra triumphantly above her head. Caro looked at the clock: "No, no, no 29:41 minutes" "Bad luck Caro, it didn't work!" said Hannah.
"Caro, stand up. Hands at your sides, legs apart." commanded Damian. "From now on, Tom and Frank can touch you where they want, for as long as they want. And then you get spanked again and you can go home. WITHOUT your clothes. You'll get them back from Hannah later. Clear?"Caro nodded embarrassed. Two younger guys allowed to touch her body anywhere, what an embarrassment.
And so Tom and Frank had the time of their lives. She caressed Caro's breasts, pinching her nipples and buttocks. Suddenly Frank also started stroking her vagina. "She's wet!" he yelled. "Oh someone is getting excited?" said Hannah. Caro turned beet red again. Not long after, the boys called it quits and left together to play outside.

Damian pulled Caro over his lap again and gave her a good final spanking. Caro's buttocks turned even redder than before. "Okay Caro, you made it through the day well. You can go home. Thank you for the great day." Hannah, meanwhile, had gathered up Caro's clothes so they could walk home together.
"See you soon Damian!" she exclaimed cheerfully, while Caro tried to get away as quickly as possible with her head bowed, an arm over her breasts and cupped her pussy.

Hannah and Caro went home together. Hannah couldn't resist teasing Caro about her beautiful skin colored outfit. When she arrived at Caro's house, Hannah gave her a firm kiss on the mouth. Caro also got her clothes back, except for her panties. Hannah kept it as a memento of this day.