Punishment Dare for Leena - Day 02

This is a continuation of Leena's punishment dare. It is highly recommended that you read day one.

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Leena awoke to her alarm going off and quickly got up. She took a shower and quickly got dressed as minuscule as possible. She was wrong yesterday, it would take four articles of clothing today.

"Unless..." Leena said to herself digging in her closet. She pulled a blue dress over her body. It came down to just above the knees. She modeled it until she was satisfied. She slipped into a pair of flats and put on her vest. Then, she called Stephanie.

"Morning. How many articles of clothing are you wearing today?" Stephanie asked half awake at 7:30 am.

"Three. This dress, shoes, and my vest." Leena answered.

"Alright, roll your 2 dice." Stephanie said.

"I'll have to roll this one twice." Leena said.

"Whatever." Stephanie responded.

Roll one was a 3. Roll two was a 2.

"Alright. 8 blowjobs. Different guys this time. I'll call you later." Stephanie said and hung up.

Quickly, Leena went next door to David's and knocked hurriedly.

"Come in." David said.

Again when Leena came in, David was sitting in his chair butt naked.

"Only 8 today." Leena said before she stuck his cock in her mouth and snapped a picture.

"Well, that's not impossible I guess, but it's not getting any easier for you now." David said as she worked to get him off quickly.

In a couple of minutes, Leena was posing with a mouthful of David's cum.

"Gotta run or I'll be late. See you tomorrow." Leena said after swallowing.

David was going to tell her about the spots of cum on her dress, but she was already out the door.

Leena hurried to work, a supermarket where she managed the clothing department. She basically wandered around straightening shelves and assisting customers find things that were right in front of them. She made it in easily and clocked in easily. She made it to her area and worked without a hassle for about an hour.

"Excuse me miss." A tall man asked her while she had been putting some socks on a shelf.

"Yes sir. How can I help you?" Leena said happily.

"Can you show me where the kids socks are?" He asked.

"Absolutely." Leena replied and headed towards children's clothing. Just then she got a text. She ignored it as she walked with the man.

"Looks like you got a little breakfast on you." The man said pointing near her waist.

Leena looked down and quickly realized that, to her horror, the glob on her dress was not gravy.

"Oh thank you. I'll have to get that cleaned up in a minute." Leena replied trying not to overreact.

"Here they are." Leena said when they arrived at the kids socks only a few feet away from where they were. Her phone started ringing and she quickly silenced it.

"Thank you. You have a good day." He said.

"You too." Leena replied trying desperately to get away.

Leena quickly ran into the breakroom and was about to clean up when her phone rang again. Stephanie on video chat. Leena looked around quickly and answered.

"There's not a cock in your mouth, that's another." Stephanie said on the video.

"I'm at work! What the fuck am I supposed to do, blow a customer in the bathroom?" Leena yelled at Stephanie's face on her phone.

"I don't give a fuck. Figure it out. I'm calling you back in just a minute and if there isn't a cock in that pretty mouth we're adding another one to your ten now." Stephanie said calmly and ended the call.

Leena looked frantically around the breakroom only seeing Jim in the corner. Apparently he had heard the entire conversation, a twisted grin forming on his 40 year old face.

"Fucking Jim, come on. I'll explain in a minute." Leena said grabbing Jim's arm and hauling him into the bathroom.

Within seconds of getting him in a stall, Leena had his pants pulled down and cock free.

As soon as her phone rang, Leena shoved Jim's cock in her mouth and answered. It wasn't clean, she could feel little balls of fabric rolling around on her tongue.

Stephanie didn't say a word, she just watched. Jim was just getting hard in Leena's mouth and she was a little insulted.

"Let me see your tits." Jim suddenly said.

Leena looked at Stephanie who nodded in approval. Then she simply slipped the shoulders of her vest and dress down to reveal her tits. Jim got noticeably harder in her mouth. Leena sat there sucking his cock for almost ten minutes before he showed any signs of cumming. He finally started shooting load after load in her mouth. She fought hard to ensure that none escaped.

"Let me see it." Stephanie said from the phone.

Leena opened her mouth to show Stephanie how full her mouth was and a little bit leaked down her chin as she did so.

"Great. I'm calling back in 15 minutes since you wanted to argue." Stephanie said before she ended the call.

"Whatever." Leena said as Jim was putting himself away. Once Jim left, Leena quickly grabbed some toilet paper and ran to the mirror and started cleaning herself up. Afterwards she quickly pulled her dress back up and quickly hurried back to her section.

Leena hadn't really been keeping track of time when a tall handsome man caught her and asked to use the changing room. He had only been in there a minute before she got a text.

"30 seconds bitch." From Stephanie.

Hesitantly, Stephanie knocked on the man's changing room door.

"Would you like some help sir?" She asked trying to drop a hint.

"Nah. I got it." He said clueless.

"How about a blowjob?" Leena said directly.

"What?" The man said.

"Do you want a blowjob from me?" Leena said slowly.

"Seriously?" The man said opening the door and standing in a tshirt and boxers.

"Yeah. Decide quickly." Leena said as her phone started ringing.

"Umm...Okay. Uh... sure." The man said stumbling over his words and his cock already rising.

Leena pushed him inside the room and quickly got his stiffening cock in her mouth before answering the phone.

"Oh my God. You are an amazing employee." The man murmured as Leena worked hard on his shaft.

Again Stephanie said nothing and just watched. It was like Stephanie was really enjoying this today. The poor guy in Leena's mouth didn't last long at all and again she showed her mouthful to Stephanie before swallowing it down. Not bad. It was only 10 AM and she was already 3 blowjobs in. Only six more to go and this was so simple.

Over the course of the next 4 hours, Leena sucked four guys off in the changing rooms. But the last guy led to tragedy. She had no problems up to that point, she had collected a couple of drops of cum on her dress, but they weren't really noticeable. However after she had swallowed this guys load, she had gotten up to leave when she got hung up on something. When she pulled, there was an awful ripping sound as the dress ripped at the seams, all the way down. The culprit was a small piece of metal that was sticking out below the bench inside. Her dress completely fell away, landing in a puddle at her feet.

Leena stood there in the open doorway, completely naked aside from her shoes and vest, wondering what happened. She snapped back to reality and gathered up her dress as best she could. She quickly ran into the back and the manager's office.

"What the hell?" Linda, the store manager, said as Leena entered her office.

"My dress got caught on something, did it just come unzipped?" Leena said frantically holding the dress up around her body.

"Oh. Let me see." Linda said and started investigating. "Where's your underwear?"

"Laundry." Leena lied quickly.

"Well, that explains why I haven't seen this dress before. Honey, your zipper is gone and this dress is destroyed." Linda said letting go of Leena's dress.

"I've only got an hour left, can't I just go?" Leena said.

"Sure. Go ahead." Linda said waving her hand dismissively.

Leena quickly clocked out fighting her dress. She rushed to leave, but just as she got to the door Jim was there. He snatched her dress and the combined power of Leena's walk and Jim's grip caused the last remaining fabric to give way. Leena ran to her car leaving Jim holding her dress and vest.

It must have been a sight for those visiting the store. A beautiful blonde haired woman running through the parking lot with nothing but a pair of shoes and a wallet with keys hanging from it. Employees had to park at the rear of the lot so that customers would be more inclined to visit being able to park close.

Leena didn't even want to think about how many people had saw her naked body as she quickly unlocked the door and jumped into her car. She was shaken up, but forced herself to drive home. She had driven naked before and knew how to hide as best she could. Some people saw her as she rushed home, but it was unavoidable. Even more saw her when she got to the apartments and raced to Rocky and Teddy's apartment.

Leena banged on the door.

Teddy answered saying, "Yo! What's up?"

"Get your dicks out. I had a shit day..." Leena started as she pushed her way inside but stopped when she saw there were five guys inside staring at her naked body. "Fuck! You've got company."

"It's okay. How many do you need?" Teddy asked.

"I only have 2 left today." Leena said meekly.

"Alright fuckers! Fuck off for a while." Teddy said and collectively with Rocky they herded everyone out.

"Were you naked all day? Didn't you work?" Rocky asked sitting down on the couch with his pants around his ankles.

"I lost my dress at work. It's a long story." Leena said before she stuck his cock in her mouth and took a picture.

Almost immediately after Leena started to work on Rocky's cock, her phone rang. Stephanie appeared on her phone.

"What happened to your dress?" Stephanie asked.

"Lost it at work." Leena replied and continued sucking.

"How?" Stephanie asked.

"Well, I was blowing a guy in the changing room and when I finished and stood up, something caught the back of my dress and shredded it." Leena explained and went back to sucking, annoyed.

"Well that sucks for you. You gotta go to Zach's tonight remember?" Stephanie said teasingly.

"Fuck. Amy's dare. Poker night." Leena said stopping her sucking for a moment.

"You have to play 5 rounds. You'll only have one item of clothing to bet." Stephanie reminded her.

"Well I could just put something on and end up giving blowjobs tonight anyway." Leena replied.

"Nope. After dark, they wouldn't count. Plus, from now on, you're outfit for the day is your outfit for the day. Period." Stephanie said coldly.

"Fine." Stephanie said and quickly went back to sucking Rocky's dick. Stephanie stayed on the line.

"I want to watch them cum on your face together." Stephanie said. "Please." She added when they didn't move.

"Fine." Leena said motioning for them to stand on either side of her and set the phone on the coffee table, propped up.

Leena worked hard on both of them, taking turns getting them right near the edge. It didn't take long to have them both just a quick suck away and Leena first git Rocky spewing and quickly sucked Teddy off. Rocky shot a load on the right side of her face just a second before she pulled Teddy out and he shot a load on her left side. They both fired three more shots leaving Leena's face dripping cum.

"Later bitch!" Stephanie said ending the call.

"Bye boys!" Leena said after grabbing her stuff.

Leena quickly made her way upstairs to her apartment. Once inside, she quickly ran into the bathroom and started the shower. Her phone buzzed a text message.

"Amended rules: Roll two die every day to determine how many different guys you must suck off, add one bj for each article of clothing you choose to wear that day, when I call you must answer with a cock in your mouth, if you fail to answer or you don't have a cock in your mouth when you do, add a bj, if you lose or remove an article of clothing you may not put it back on, you can only swallow five loads of cum a day no matter your roll, if you fail three days in a row you must spend a day in the gloryhole booth." Stephanie's message read.

"Send me a feet pic. lol." Another text from Stephanie.

Leena looked down at her naked feet, she had already shed them to get in the shower. Solemnly, she took a picture of her naked feet.

"Kinky. Looks like you'll play strip poker naked." Stephanie responded.

Leena put her phone down and just jumped into the shower.

After her shower, Leena spent the rest of the day laying around. She cooked some mac and cheese for dinner. Soon, it was 7:30 and time to leave. Leena gathered her wallet and keys, took a deep breath and walked naked to her car. It took twenty minutes to drive to Zach's house and it looked crowded when she got there. There were 8 vehicles there, all parked in front of Zach's huge house. It was a big event to be invited to Zach's strip poker night. Sure, some people have shown up underdressed, but never naked. The stakes were high and she had never been.

Nervously, Leena got out of her car and headed in completely naked. There was a man there, a butler. Leena knew Zach was a trust fund baby, but she didn't realize he was this rich.

"Well, this is a first, you are more than a little underdressed madam." The butler said as he lead her inside the entryway of the beautiful mansion.

"I don't think I've ever seen someone buy in nude. How long do you intend to play?"

"I have to play 5 rounds, 5 times. So, I'll be here the next 4 games too." Leena replied.

"My, I certainly hope you come better dressed next week." He said as they approached a doorway that led to a huge hall.

Inside were about twelve people, all of whom were better dressed than she was. This would certainly be entertaining at the least.

"Ah! Leena, so good of you to join us." Zach said welcoming her.

Everyone was gathered around a large table. Leena didn't know what it was but was informed that it was a Hold 'Em table.

"Alright." Zach said sitting by the chips. "How many Russell?"

"20 chips." The man named Russell said.

"Alright. Shirt, socks, and shoes." Zach replied.

The man named Russell took off and handed over the requested clothing items. This went on with each individual giving up some clothing. Finally, Leena stepped up to Zach.

"How many chips?" Zach asked.

"I don't know, I have to play 5 games at the least." Leena replied.

"Probably best to start with 20 chips." Zach answered.

"K. Uh... what's the price?" Leena asked.

"Okay." Zach said grabbing 20 chips and setting them aside. "Well, since their is no leader right now I guess... a blowjob for me."

Leena just nodded her head and got down on her knees. She unzipped Zach's pants and fished his stiffening cock free. Everyone watched closely as Leena swallowed his whole cock and had him rock hard in seconds. Within a couple of minutes, Leena pulled his cock out and shot his cum on her face. The butler was there with a wet washcloth almost instantly and Leena cleaned her face up.

Leena was paired up with a group of six other players 4 men and 2 women. Once the game started she was immediately confused. Everyone threw in one chip for ante and she did as well. Then the dealer dealt each player 2 cards face down. Then, he dealt 3 cards face up and 2 cards face down. She looked at her cards, a 3 of clubs and a 7 of diamonds, and the face up cards, a queen of hearts, an ace of spades, and a 4 of clubs. Luckily, she was last to go in this game and got to watch everybody go before her. The first guy threw in a chip and said, "Stand."

The next guy threw in two chips, "Raise."

The woman next to him, who had a lot of chips but was only wearing a pair of panties, threw in four chips, "Raise."

"Stay." The next guy said throwing in 4 chips.

"Stay." The girl in bra and panties said throwing in 4 chips.

"Stay." The guy next to her said.

"Stay." Leena said throwing in 4 chips.

Eventually everyone had 5 chips in.

The dealer flipped the first of the two face down cards. A Queen of clubs.

"Stay." The first guy said and threw in another chip. By the time it got to Leena, she stayed and threw in six chips. She didn't realize that she would be 11 chips in before the end of the first game.

The first guy folded saying, "Too rich for my blood."

Leena didn't even know that it was an option. After the last card was flipped, a 5 of diamonds, the bets increased. Leena folded but was down 11 chips. The woman in just her panties won with three queens and two threes. A full house.

The next round started and everyone anted 2 chips. Leena did too. Her hand had two aces in it. She was ecstatic, a chance to win some chips back. After the first card was flipped, "The Turn," she learned, all 9 of her remaining chips were in. The dealer flipped the last card, "The River," and when it got to Leena she needed 5 more chips.

"So... what now?" Leena said.

"Zach, she needs more chips." The dealer said.

"You know what to do. 20 chips for 30 seconds of oral to each player." Zach said.

"You heard him." The dealer said.

Leena climbed under the table and went to the first guy. She pulled his cock free and started sucking. She was counting in her head because the dealer said next and she had only counted to twenty.

Leena went to the next guy and swallowed his cock. She counted in her head, but she was too fast this time. She had reached forty when the dealer said next.

Leena moved to a woman this time, that pulled her panties to the side. Leena began licking at the woman's slit, not a first for her. She quickly found the clit and tortured the woman. In just a short time, the dealer called for next and Leena left the woman wanting.

Leena moved to the next guy and quickly stuffed his cock in her mouth. But after only counting 10 seconds in her head, the guy stiffened up and proclaimed he was going to cum.

'Shit! I've already swallowed five loads today. Does that mean I have to wear this cum? Better safe than sorry.' Leena thought to herself as she pulled the man from her mouth.

Just in time, he unloaded on her face, six ropes of cum. The first went into her hair and down her forehead just over the right side of her nose. The second almost hit her in her right eye but just barely missed. The third hit her nose and splattered across both cheeks, the fourth across her lips, the fifth on her chin, and the sixth was dribbled on her chest. The dealer called next and Leena moved on to the other woman.

Leena licked the woman's slit, not having time to clean herself up. She could taste the previous man's cum as it slid down her face getting in her mouth. It wasn't long before she heard the dealer call next.

Leena moved over to the next guy and started downing his cock. At least he kept himself from cumming before the dealer said finished.

Leena got back out from under the table and sat back in her chair.

"Anyone have a napkin?" Leena asked.

Zach presented a wet nap and Leena cleaned herself up. She collected her chips and threw in 5 more chips. Everyone called and Leena actually ended up winning with three aces and two jacks. She was up to over 70 chips.

Next hand and she lost 14 chips.

Then the next she lost 28 chips.

Last hand and she lost 30 chips.

She had to cash out her remaining chips. Didn't even know what that meant.

"Zach, I need to cash out my chips." Leena said to Zach.

"Nope. You weren't wearing anything, you have nothing to claim." Zach replied.

"Fine." Leena left and drove home. Another day down.

'Fuck, I have to work again tomorrow. Well hell.' Leena thought as she lay in bed slowly falling to sleep.

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PREVIEW OF DAY 3

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