Penny's New Job

Pennys New Job

Due to covid hours at her office job had been cut, forcing Penny to look for a job on the side to recoup the lost hours. She had sent resumes out to ads she found online, but often the interviewer was looking for more experienced workers.

Luckily she found an ad looking for a nighttime manager at a retirement home. The ad specified no experience necessary, and the hours worked perfectly on her schedule, so she phoned in for an interview, and got the job a few hours later. Penny smiled to herself at how easy the job was, she just had to walk around and check up on everyone, if there was an emergency she just had to call the nurse on standby, easy.

On her first shift, she quickly realized that easy also meant bored. There wasn't much to do, she walked around the first hour, talking to everyone, but people either were eating, playing some games, sleeping, or watching tv.

Penny glanced at the clock from her desk and groaned seeing that only 2 hours had passed, she still had another 3 to go! She didn't have her phone on her, that was against the rules and she had to put it in the office. The only thing she had was her purse and the only thing that could keep her distracted was a piece of gum, lipstick, and her car keys.

Another half an hour passed and soon the room started to empty out. "Huh, guess everyone has an early bedtime," Penny muttered to herself.

There were only 3 retirees in the room left with her, they were all sitting at a table talking amongst one another. Shrugging to herself she got up to see what they were up to.

Halfway to them, she saw they were playing a card game. She wasn't sure which one, she was never one to play games growing up, except of course if drinks were involved.

"So what game are you three playing, when you should be in bed this time of night? Go-Fish? 21?" She asked them as she reached the table.

"Poker." A bald man answered she thinks his name was Larry. "Wanna join us?"

Penny glanced nervously around the table, she was vaguely familiar with the game, but as she looked at the center she saw they were gambling real money. The point of working here was to save money not to spend it.

"Poker? Sorry gentlemen but I'm here to make money not spend it." She said shaking her head, she turned around to start walking back before she felt someone grab her wrist.

Penny turned around and saw it was Larry. "Heyyy, not so fast Penny, were just having a friendly game here, you can bet as much as you're comfortable with." The other two men were nodding in agreement.

Penny bit her lip, she would be in big trouble if she got caught playing games instead of working, and she didn't want to lose any money. But as she looked at the pile of money at the center she could only imagine how much she could do with all of that. She would have more money to spend on clothes, maybe even enough to fix her car.

"Sure, I could play a few hands." She smiled at them sitting at an empty chair.

Larry had been kind enough to explain the rules to her, she thanked her lucky stars he was being kind. She initially cashed into the game at $50. It was the most she felt comfortable losing if she was horrible, and plus she had more money in her purse for rent. But the first hand came out and she won!

Penny squealed in excitement as she won her first hand, and her pile of money grew bigger. The next hand came and she won again! Penny started to get really excited as luck seemed to be on her side, no matter which hand she had, and whether it was good or bad she always came on top.

'I can't believe my luck! I should go to casinos more often!' Penny thought to herself as she won another hand. Soon she had around $200, if she were thinking logically she would've bowed out by now, but she was hooked on this game and wanted to continue playing. Unfortunately, she was too caught up on her winnings she didn't notice to glance Larry made to his friends before dealing the next hand of cards.

The next hand was dealt and she had a pair of 6's. She smiled to herself as she knew a pair was always good, so she bet big. When it was time to reveal she had a giant smile as she showed her hand. Before she could reach over and grab it she saw one of them show a hand of a pair of kings. Penny's heart dropped as she realized she lost, and she saw the pot go further away from here.

'It's okay, I was bound to lose eventually, but I still got it!' She thought confidently to herself.

The next hand came and she saw she had a 2 and a 6, not good. Still believing that maybe she'll still get lucky she continued to match bets. However, in the end, she didn't even come close to winning and watched more of her money being taken away.

Penny bit her lip, she still made more money than what she came in with, she could back out now. But as she had to admit playing poker and winning was very fun, and as she glanced at the clock and saw she still had a while before her shift ended, she figured playing more wouldn't hurt.

It did hurt, very much. Penny learned the hard way that the house always wins. Any good luck she had was gone as with each hand her hand got worse and worse, and whenever she thought she was about to win, whether it was with a full house or three of a kind Larry always had a better hand. But the thrill to win was still there so when she eventually ran out of money she reached in her purse and threw her rent money in as well. To her horror that still didn't stop the losing, spending every cent on her to recoup her lost money, but as the final card turned over she groaned as she lost another hand.

"Okay, one more hand! Deal me in!" She spoke up as the deck was being shuffled.

"Sorry Penny, but you're out of money," Larry told her while shuffling.

Confused, Penny glanced down and her jaw drop as she realized she had no money left! She started to breath harder as she realized what she just did, she just lost her entire rent money for the month! She wasn't going to get paid for a few weeks, she was screwed.

"Please! One more hand, you have to let me win back my rent money! I'll be kicked out of my apartment if I can't pay this month's rent!" She pleaded, hoping they would give her mercy.

Larry gave her an innocent smile. "Well, we want to let you in but you have to barter with something. Neither of us are interested in the purse, and we're sure you wouldn't gamble away your car."

Penny gave him a confused look and where he was going, but as she went through the list of things she on her person the only thing of value she could think of was her clothes.

"You want me to play strip poker?" She deadpanned. It wasn't the first time she was propositioned to play that game, men at parties always offered the same game to her, of course, every week she rolled her eyes at them and tell them to get lost, she knew this time would be different.

She glanced at her current outfit, all she was wearing was a red blouse, skinny jeans, bra, and panties. She was in shape, her C cups were still perky, there was nothing wrong with showing off her body, but she was not interested in stripping, but as she looked at the large pile of money each of the gentlemen had, and as she looked at her empty pile she knew she had to get back her money. Her luck had to turn around eventually.

"Alright, I'm in." She finally said.

She saw the three of them smile at her, and the game resumed.

Of course, that ended up not changing her luck as she lost the hand. Penny sighed heavily as the three of them looked at her expectedly.

"My heels count as one right?" She asked, half pleading. All three of them shook their heads.

She groaned as she started fiddling with the buttons on her blouse, with each one undone she was exposing more and more of her cleavage until all the buttons were undone. She shrugged off the blouse conscious of the fact the men were all staring at her chest. She kept her eyes down as she threw it into the middle.

'It's okay, its just a blouse, a right really cute blouse you loved to wear on dates.' She just hoped her luck would finally turn.

Her luck didn't change as with the next hand her heart dropped, it was a 5 and 9. Nothing good came about it was only another 5 came up, but someone else had beaten her with a straight hand.

She knew which clothing she had to take off next. She sighed heavily as she stood up and unzipped her jeans. They were a bit tight and she had to shake her hips a bit to get them off, causing her breasts to giggle in her bra. She blushed as they fell down her legs and pooled by her feet, she covered herself as she was now standing in the middle of the room in just her bra and panties.

'Oh god, what am I doing? If I get caught not only will I get fired but possibly arrested! I don't need my mom asking me questions on why I'm only wearing underwear in jail!' Penny started to panic.

"Another hand Penny?" Larry asked shuffling the deck, he made no effort to hide his staring.

Penny's face further reddened as all of them were staring at her body. It's not like she wasn't used to attention from the opposite sex for her body, and she did do a lot of stupid things growing up that involved nudity, but she was young, stupid, and most importantly drunk. Here she was standing in the middle of the room in her underwear, somber, and regretting every moment.

She wanted to say no, desperately, but she had to win back her money. Penny didn't want to go through the humiliation of asking her neighbors for money again, she wanted to be strong, and independent, but as she glanced down at her very exposed body, she felt like a cheap stripper.

She nodded her head and quietly sat down as the cards were dealt. She almost wanted to groan as she only had a 3 and 8. She knew right away she was going to lose her bra, and as the final cards were shown she verbally groaned as she wasn't even close to winning.

Penny nearly cried as she was forced to once again take off her clothes, she wiped her eyes quickly to not show them she was crying. She reached her arms around her backside and struggled to grasp the clasp of her bra with her hands shaking as much as they were. She finally managed to unclasp her bra and the loosening of her bra straps made her realize how all too real this actually was. She slumped her shoulders and let her bra straps fall to her arms. She lifted one arm out of a bra strap, then the other, careful at to keep at least one hand on her bra at all times, so it wouldn't fall off. The only thing keeping her boobs covered now was her hands keeping her bra on her. She quickly let go making sure to keep the girls covered.

She squirmed in her seat as all she was wearing now were her panties. One of the other players carefully reached over and grabbed her bra, looking it over.

"Man must be good to take this thing off, it was making your girls look small." He chuckled. Penny blushed at those words, mindful of the fact she was cupping her breasts.

"I better get going, I need to go to my locker and call someone to grab me more clothes," Penny said standing up abruptly trying to leave as quickly.

"Hold on? Don't you want to win your money back?" Larry called out to her.

"I don't think I can win my rent money back with only my panties left," Penny said quietly.

"Well, why don't we make this more interesting. If you play one more hand we'll put $200 in the pot." Larry offered.

Penny paused in step halfway out of the room. She was thinking that $200 would be better than nothing, and if she won she would be back in the game and wouldn't have to further bet her clothing. She looked down at the last piece of clothing on her, would it be worth it to bet her last shred of dignity? But as she glanced again at each pile of money on the table, her greed got the better of her.

"I'm in," Penny said quietly walking back over and sitting down.

She blushed as she saw all the men staring at her with smiles on their faces. 'How the heck did I get myself into this?' She thought bitterly as the hands were being dealt.

Penny glanced nervously at the two cards she was given. She reached one arm out slowly keeping in mind to have her breasts covered with the other. She delicately grabbed the two cards and brought them closer to her. 'Come on, come on, I really need some good luck right now!' She mentally begged as she flipped the cards over.

She nearly jumped off her seat in excitement! She had a pair of kings! Penny internally squealed in delight, her luck was turning, but she had to downplay her reaction in hopes the others would bet more.

Three more cards were put on the table and her eyes nearly popped out, two more kings! She had a four of a kind, Penny struggled a bit with which poker hands were good, but this had to be a winning hand!

It didn't matter what the other two cards she knew she won, and when everyone revealed their hands and she saw she had the best hand she jumped out of her seat, raised her hands in the arm, and jumped up and down in excitement. "Snap! I mean Mahjong, or whatever it is, I have four of a kind I win!"

She soon stopped celebrating and saw the other three looking at her with their eyes wide and their jaws drop. Penny tilted her head in confusion until she looked down to see what they were staring at. She blushed in embarrassment as in her celebration had forgotten she was topless and just gave them an excellent view of her boobs bouncing up and down, her nipples poking at them.

Penny immediately cupped each of her breasts and sat down quickly. "So sorry." She quietly muttered, her face still beating red.

She heard Larry clear his throat. "I'm sorry to have to tell you this Penny, but you haven't won."

Her head snapped up and she looked at Larry as if he grew a second head. "Haven't won? What do you mean?" She asked incredulously.

The man had an apologetic look on his face. "In the rules of poker, having four of a kind is usually a winning hand, but only on weekends. Today is Thursday. I'm sorry but my three jacks beat it."

Penny could feel her eye twitch, she looked at the other two players hoping they would defend her but they seemed to agree with him. "I haven't heard of anything that ridiculous! How do I know you're not making this stuff up!"

The man shrugged. "That's how I've played this game, and I've played it for over 30 years."

Penny started to panic, she started to squirm in her seat at the realization she just lost. She glanced down and started to tear up at the thought of taking off her last shred of dignity and stripping naked. Maybe she could sweet-talk them?

"Well, tonight certainly has been educational for me. So I'll bid you all goodnight, as I have my rounds to do, so if you'd kindly return my clothes I'll be on my way... please?" She said sweetly, she batted her eyes a few times, it always worked when she wanted something from men.

"Actually Penny we're feeling quite tired, so I think we'll turn in for the night WITH our winnings, and that includes the panties you're still wearing, thank you," Larry said as everyone started to get up and put their winnings and her clothes in a small sack.

Penny cried out placing a hand in front of her panties. "Please, please, please don't make me take them off, I don't have anything left!' She pleaded, but then a thought occurred to her. How could they possibly force her into giving her underwear? She smirked at her revelation. "Actually never mind, I think I'll keep them, she turned around and marched out of the room.

"I guess I'll just have to explain to your manager tomorrow why instead of working you were playing poker with us." He called out behind her.

Penny stiffened at his response, she knew she would be fired right away if her manager heard that.

"Fuck." She said quietly as she turned around. She hooked her hand on the waistline and slowly pulled them down, once they were mid-thigh she let go and watched them drop on the floor by her feet, leaving her completely naked. Not wanting them to see her pussy she turned the lower half of her body as she reached down and grabbed her underwear. She looked up and saw all three of them staring at her nude body, Penny's face further reddened at that, she shoved her underwear onto Larry's hand making sure to not look him in the eye.

"Fine piece of lingerie Penny, thank you," Larry said looking up and down her body before turning around and walking out of the room soon followed by the other two.

Once she was sure she was alone Penny groaned and sank to her knees not bothering to cover herself. She wanted to cry at her current situation, here she was, broke and sitting butt naked with nothing left.

Penny knew she couldn't stay here, the humiliation of someone seeing her naked was more pressing than this job. She hastily stood up and walked over to her desk writing a half-assed note that she had a family emergency and grabbing her purse. Running over to the door she peaked outside to see it was empty. She took a deep breath before opening the door and running down the hallway.

She could feel her heartbeat faster and faster as she was streaking down the halls. Anyone could open those doors and see her perky tits and firm butt shaking as she ran past them. Unfortunately one of the doors opened and a miss Perkins walked out just a couple feet ahead of her.

"Oh dear, Penny why are you naked hun?" She asked clearly surprised.

Penny had to hold back a scream and covered herself, not slowing down. "Just go back inside you didn't see anything!" She told her, leaving Perkins with a parting image off her bouncing butt.

It didn't take long before she reached the emergency exit, she opened the door and closed it behind her. Her face was still red, whether from being caught or all the running she didn't know. A warm wind gently caressing her pussy reminded Penny of her current situation, she looked around and spotter her car. She unlocked it and sat inside. She flinched as the cool leather made contact with her bare butt, sending an odd sensation through her body. She just hoped this wasn't a feeling she'd get used to.

Though Penny had driven countless times, it seemed driving naked was a much different experience. Due to a lack of shirt, she would constantly have to adjust her seat belt as often it would rub up against her breast and nipples. What was worse was that she felt very uncomfortable driving naked that it would cause her to constantly readjusted in her seat. That meant she would inadvertently rub her pussy against the leather. The mix of being uncomfortable and pleasure was not making her day any better. She had to hold a groan as she stopped at a red light. Having enough of it she ripped off the seat belt, safety be damned. She heard a gasp to her left, she looked over and saw a man in a passenger car looking at her, with a clear view of her naked tits.

Penny screamed and lowered herself onto the seat blushing, trying to hide as much as she can. When the light turned green she speed off towards her apartment.

"Okay I'm almost home, only two people have seen you naked, that's not too horrible. Just gotta walk in through the back door and hopefully not run into anyone on the way up." She muttered to herself, trying to make herself feel better.

Her car had different plans as she heard a clanking noise coming from the engine. Penny groaned as she was well familiar with this sound. "Stupid check engine light." She muttered to herself. Her car ended up stopping not too far from her apartment. She held back a scream as she tried to turn her engine on, but it was dead. "Dammit! I was so close!" She yelled banging her head on the steering wheel. She wanted to cry as she was so close to her apartment but now stuck.

She looked up ahead and could see her building, a 30 second run at max. She bit her lip as she noticed the sidewalks were very busy, there was no way she could sneak by all those people, she would have to streak through