Don't Bet What Your Not Willing To Lose by The Stranger

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Girlspns
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Don't Bet What Your Not Willing To Lose by The Stranger

Post by Girlspns »

The Stranger wrote:
Part 1

Beddington was a small town in Nevada. It was well off of the main highways, so it never grew into any kind of gambling hub, but their main industry was providing equipment for the big gaming complexes. Because of this, they were very serious about gambling. They had even passed a town ordinance stating that welching on a bet would be treated as stealing. The judge would decide felony or misdemeanor depending on the real or perceived value of the winnings/losses. Needless to say, the more embarrassing the payment, the more likely that welching would be ruled a felony and involve jail time. This ordinance was enforced by the local law enforcement, and this led everyone in the area to call Beddington “Betting Town”.

To outsiders, this may seem extreme for something most people do casually. In Betting Town, there was a lesson to be learned, “Never bet what you are not willing to lose.” No one was ever forced into a wager, and evidence of such a thing could mean jail time for the offending party. You didn’t have to accept a bet or its terms. Once agreed upon by both parties in front of witnesses, it was ironclad. Most just bet amounts of money or services to be rendered, but there were always a few humiliation bets, and the people of Betting Town had seen just about everything. If it was the agreed upon terms of a bet and kept within city limits, it was legal.
Donna had grown up in Betting Town. She did her share of betting, sometimes with rather daring consequences, but had never lost more than a few dollars or a quick panty flash. She wasn’t overly cautious, just lucky, and couldn’t imagine her lucky streak ever ending. Many had tried to embarrass her before, at 5’10” brunette with firm C-cup breasts and a toned farm girl physique, many guys had tried to get her naked but it usually backfired.

Donna’s best friend, Stacey, had opposite luck. If she had ever won a bet, no one could remember, but she never backed away from a wager. Being a 6’ blond with DD breasts, she was a favorite target for all of the boys and many of the girls thought that she was a closet exhibitionist. Currently, she was paying off a wager that stated that she could only wear a skimpy string bikini and sandals for the entire month of June, even to church and work. So far, she had made over $300 in tips at the drive-in diner, and it was only June 3rd. This was mostly due to the jogging to and from cars as well as the occasional wardrobe malfunction, which only momentarily embarrassed her because “with all the bets she had lost most everybody had already seen everything.’ She could be ditsy at times but didn’t consider herself an exhibitionist, she had just gotten used to the public exposure and it no longer bothered her. It did, however, bother her family when she wouldn’t feel the need to wear clothing around the house. Her father was the local Baptist minister and he was constantly ashamed of his daughter.

Donna worked waiting tables in the local pool hall. She was going to be a senior in high school in the fall, so she couldn’t serve alcohol where the big tips were given. She served food and other drinks and tried to make due with the meager tips. Her co-worker, Myrna, was a 22 year old Irish lass and daughter of the owner. She was a delightful, high-spirited girl who everyone, including Donna, just loved being around. Her father treated them both fairly, never giving favoritism (Myrna wouldn’t allow any even if he did) and Donna liked the job. The only problem was that Myrna; with her long red hair, pale complexion, and medium build with D cup breasts; tended to get the lion’s share of the tips. To supplement her income, Donna played pool and cards to win some extra cash. She had become known as quite the shark.

It was late June and Stacey had made so much in tips that Donna wanted to step up her game so she wouldn’t be left behind. Around this time Max Burnns came to town. He was a professional card player who had won enough to retire. He wanted to open his own bar in his home town where people could play cards and he could keep his skills sharp. He wanted some good poker tables and chairs, custom poker chips, and a few slot machines for drinkers who didn’t play cards. After looking over the merchandise and placing some custom orders, he checked into his motel and the headed to the local pool hall to check out the action. He found a nice Irish pub with pool and card tables where gambling, not alcohol, was the prevailing vice. Not there for financial gain, he watched for a while, then sat in on a low stakes game to unwind.

Even though Max wasn’t playing at full competition level, he was still easily the best card player there. He tried to keep his bets small, but it was against his principles to allow someone to win just to keep them happy. Fortunately, the people of Betting Town enjoyed a well played game almost as much as winning. This man was good and they could tell. It was about this time that Donna’s shift ended, and as she headed past, some of the guys called her over and introduced her as the bars best card player.

Donna had been having a slow week. Most of the customers were Myrna’s regulars, and the few she got were lousy tippers. On top of that, Stacey had had a huge night a few nights ago when, unbeknownst to her, one of her male co-workers had untied her bikini bottoms while she waited on an order. She spent over an hour waiting on customers bottomless before being clued in to her exposure. In all, she cleared over $400 that night in tips alone. The manager was starting to wish that the bikini was her usual uniform. Donna was being left in the dust and needed a way to make up the difference. This new gambler seemed like a good opportunity to get some extra cash. The locals said that this guy was good, but she could usually beat them, so she didn’t worry too much. She was the card shark here.

Max, like any pro, was good at sizing up his opponents pretty quickly, but always played it safe at first. For a gambler, overconfidence was a vice that could make you poor in a hurry. He could tell within minutes that this girl was a perfect storm of youth and overconfidence, and would gamble her life away if not taught a lesson soon. Losing big was a hard lesson, but if learned early, could save you in the long run. Max’s mentor had taught him this lesson when they first met, and that made him the success he was today. Question was, could she be taught or was she too far gone. The patrons of this bar had been stroking her ego for a while now and she may never get right.

Max took it slow at first, and soon found another flaw in her game. When she had a good hand, she got aggressive and rarely folded, even when holding junk. A lesser player could be intimidated by this, but Max found it laughable. After she had won a few small hands, he started playing for real. Soon, he was up a few hundred dollars and she was asking the boss for a pay advance. The boss gave her what she had earned this week, “and not a penny more, so don’t ask”. She was down to her last $60.

The next hand looked good for Donna. She started out with two pairs, kings and tens, and drew a king. She knew that she had this one won, so she went all in. Max saw her $60 and raised $200. Max knew that she didn’t have any more money and thought that this would end the lesson. He couldn’t have been farther from the truth, for now her overconfidence raised its ugly head. First, she asked to go to the ATM. He told her that if she left the table, she would forfeit the pot. He also wouldn’t accept IOUs and the other patrons were already tapped out.

It was at this time that said the words everyone in town loved to hear: “How about a wager?” Max knew about the town’s love of any type of gambling and took all wagers very seriously, so Max simply asked, “What do you propose?” Donna thought about it and said, “If my hand is better, I get the pot. If your hand is better, you get the pot plus…..um…..how about my shirt.” Donna was wearing a sports bra underneath, so going without her shirt wouldn’t be a big deal. Max was shocked. Was she overconfident to this extreme, to not fully consider the consequences.

He then remembered something his mentor had told him. His mentor had a few young players under his wing, and one had become so cocky that he was basically putting a target on his back, everyone wanted to take him down. Their mentor had to do something before the kid became the doormat of the professional players. The kid was good for a rookie, but would get eaten alive by seasoned players. The mentor played the kid, taking every scent the kid had plus his car. He then booted the kid out telling him to get a job and come back when he had some talent. When Max asked why he was so harsh, he just looked at the deck and said, “When overconfidence is too strong, the fall must be even greater for the lesson to sink in.” The kid returned a few months later as a more disciplined and smarter player.
“No way” was Max’s response. “Look girlie, we’re playing real poker here, not college kids strip poker. This is about money, and that shirt ain’t worth $140.” Now, he thought, was the big decision… Fold and learn her lesson, or prove that her fall needed to be greater. She sealed her fate when she said, “H-How about for all of my clothes?”

Donna could hardly believe the words we’re coming from her mouth. She couldn’t believe it had come to this. She had never been in such a predicament before. In a few hours, she had gone from trying to catch up to Stacey, to trying to salvage whatever she could or lose everything (and she meant everything). The thought that she kept coming back to was, “but I don’t lose, and this hand is close to unbeatable. I gotta go for it! If I lose, this is Betting Town. I won’t be the first or last to take the “Nude Walk of Shame”home.”

Max just looked down and said, “Think about what you’re saying. Is that really what you want?” She simply nodded yes. Max got a piece of paper and said,” I want this in writing sso that there can be no arguments or accusations of indecency.” He wrote:

I, the undersigned, agree that if Mr. Max Burnns’ poker hand beats mine, not only will I lose all money in the pot, but Mr. Max Burnns will own all of my clothing and I will be left nude. I have read these terms, and by my signature verify that I fully understand and accept these terms.
Signed,

Max said,” You should read over it and think about it before you sign.” Donna, however, didn’t want to think about it or she might lose her nerve. Without even glancing at it, she signed and handed it back. Max shook his head, sighed, and said, “Ok, let’s see what you got.” Donna, smiling broadly, showed her hand: Full House, kings over 10s. Max nodded approvingly and said, ”That a good hand, but it doesn’t beat Four of a kind” as he laid down four 3s.

Part 2

Donna could’ve been knocked over by a feather. All these years never losing anything big, but now she had to strip naked at work, give some guy she just met her clothes, and bike home nude. As this reality was sinking in, Bob Howard, a 23 year old who was a regular of Donna’s (and secretly lusted after her), cleared his throat and said, “Um…you have to pay up.” Donna knew the penalties for welching, and definitely didn’t want a criminal record. Besides, she had no one to blame but herself.

When she finally came around, she knew what had to be done. First, she pulled the tight uniform t-shirt over her head and dropped it on the table. She then unbuttoned and unzipped her khaki shorts and let them drop to the floor. As she stood there she realized that up to now her parents and Stacey were the only ones to see her in her underwear. None of her boyfriends had ever gotten this far. She then shook her head and thought, “Why are you spacing out? They and possibly a good portion of the town will see a lot more soon enough.” She then grabbed the bottom of her sports bra, took a deep breath, pulled it over her head and put it with her shirt on the table. She was now topless at work, a small pair of white panties the only things guarding her modesty and they too would have to go. With trembling hands, she hooked her thumb in the waistband on both sides of her body, closed her eyes, held her breath, and quickly pushed her panties past her knees letting them fall to the floor. She picked up her shorts and panties and laid them on the table with her other clothes.

She was getting ready to start her long, nude bike ride home when she heard Max say, “Excuse me, but you are still wearing some of my property. The wager was for all of your clothes. The socks and shoes are mine too.” Totally defeated, she stooped down, giving all in front of her a nice beaver shot, and pulled off her shoes and socks, adding them to the pile. She was surprised how much losing her shoes and socks affected her. They didn’t hide anything important, but they were her last bit of covering and now they were gone. Without speaking, she exited the building, grabbed her bicycle, (now more than ever she wished her parents had gotten her a car when she turned 16) and started the long ride home.

Even though the sun had gone down, it was still warm outside, and it was summer vacation. All but the very young or very old were out enjoying the outdoors now that the burning sun had gone down. They were soon paying undivided attention to the Lady Godiva wannabe. Not only was Donna conspicuously nude, but with her work schedule had only managed to get a farmers tan on her arms and legs. Her midsection was pale white accentuated by her tanned limbs. They could also see that either her pubic area had never seen a razor, or she was being violated by a small, furry animal (of course, she hadn’t planned for it to be on public display). Younger kids pointed and laughed while teenagers took out camera phones and hurriedly snapped photos and video. Adults merely smiled and waved at the latest victim of their own foolish wager.

For Donna, it was overwhelming. She hadn’t considered that all of these people would still be outside with cameras. What she didn’t know was that as soon as she lost, many of the bar patrons started informing friends of the coming spectacle. Donna had always been shy, never even wearing a two piece bathing suit, and most of the men in town had wished for a good look at her fit yet curvaceous body. This was beyond their wildest dreams. Donna could feel their eyes and, while embarrassed, was kind of enjoying all of this attention. She wondered, ”Is this how Stacey feels when doing those embarrassing things after losing a bet? Is this why she kept betting even though she always lost?”

It was at this precise moment that she heard a familiar voice calling her name. She turned to see Stacey running towards her, dripping wet, wearing only a towel. Apparently, she was in the shower when her little sister told her of Donna’s nude ride. Knowing Stacey would want to rush to her friend, the younger sibling had taken Stacey’s bikini and only left her a towel. While Stacey’s parents disdained her frequent public exposure, her sister often conspired to show her sister to the world whenever possible. Stacey’s sister, June, had always been kind of a tomboy. She recently turned 15 and was becoming more interested in the opposite sex, but with her brown hair, B cup breasts and short stature (5”5’), she found it hard to compete with her voluptuous and often exposed sister. She told others that since her sis seemed to like the attention so much, June would help her get that attention. Truth be told, she derived some sexual pleasure from her sisters embarrassment and, although not a lesbian, did enjoy seeing what to her was a perfect body.

Stacey raced over to her friend to ask what had happened. The last thing Donna wanted to do was sit outside, naked and recall how she had lost her money and clothing. However, she could see that her friend was concerned, so much so that she had run to her side almost naked herself without even taking the time to dry off. She told her friend of the card game, the lost money, her good hand and his better hand, the stripping, and her nude ride being recorded for posterity. Stacey grabbed and hugged her friend, dropping the towel in the process. Donna was unsure what to do, being nude in public and being embraced by her equally nude friend, but decided to go along with it and hug her back. Many of the male onlookers found it difficult to stand. June also found this strangely arousing.

Part 3

When Donna finally arrived at home, she couldn’t believe her eyes. Max was there with some other men taking boxes from her house! She hurried to the house to find her mom. Her dad had died three years earlier from a car accident, so it was just her and her mom, Isabelle (although she preferred to be called Izzy). Izzy was in her mid fourties and was to many a definite MILF. She was 5’8” with long auburn hair pulled into a ponytail, and full C cup breasts. She work as a dealer in Reno and usually left a few buttons undone on the uniform to get good tips plus she liked the attention. She was something of an exhibitionist, dressing provocatively around the house, especially when Donna had male visitors. Donna was certain that the reason she didn’t date much was because all guys attention went to her mom. This ride was the first time she had experienced that kind of attention.

When she found her mom, she was standing next to Max holding a piece of paper. Donna asked Max, “What are you doing here?” “I came to get the rest of my winnings” was his reply. Donna was getting ready to go ballistic when her mother asked “Donna, did you even read this before signing? It says here that you bet all of your clothes and you signed. There’s nothing I can do.” Donna tried to argue that she meant the clothes she was wearing, but Max stopped her and said, “That outfit you were wearing wouldn’t cover your losses. I told you, I wasn’t playing strip poker. I was playing for money. You offered all your clothes as collateral so I took a chance. I’m hoping that by selling what I can and donating the rest as a tax write off, I’ll get my money.”

The true gravity of Donna’s predicament finally hit her. She was broke, naked with no clothing, and the only way to get money was working. But would she have to work naked? Could she work naked? She worked at a bar, not a strip club. Max’s final words to her hit hard. “Maybe this will teach you not to be overconfident and think before you act.”

Part 4

The next day, Donna called work about her predicament. Her mom had a smaller body and all of her clothes fit tight on her, there’s no way Donna could wear them. She couldn’t borrow her mom’s clothes and payday for both of them was in two weeks. Car problems had drained their savings so buying clothes wasn’t a viable solution. She was naked and would stay naked until one of them got paid.

Izzy couldn’t see what the big deal was. Everyone knew that she lost a bet, so her walking around town and working naked would just be seen as part of the wager. Honestly, Izzy wished she had an excuse to go around town naked. It was ok if it was a lost bet, but just for kicks was indecent exposure. She had to find a wager to lose. Just the thought of the whole town looking at her nude body was making her wet. She hoped Donna would have to work so that she could have some alone time.

Her boss had little sympathy for her. He knew that betting her clothes was her idea and the gentleman had tried to talk her out of it. She could either come to work, or look for another job while naked. No job meant no income and no income meant no new clothes. She didn’t really have a choice. Donna the nude waitress would be at work for her usual shift.

The ride to work was worse than last night’s ride home. It was midday and all of the kids were out playing. Most of the kids pointed and laughed. Some of the boys got their first boner and she had to giggle to herself after seeing so many trouser tents. There were also older couples out. Some voiced their disapproval while some of the old men cleaned their glasses to better take in the sight while their wives stared daggers at Donna.

When she finally got to work, the boss gave her one of his aprons to wear. It covered her front pretty well, but her bare backside was in full view. Although she had some covering, this almost seemed to her to be more erotic than being totally nude. She asked for another to cover her backside, but the laundry had just been picked up and this was her bosses only spare. All of the bar towels were too small to make a wraparound skirt, so she thanked her boss for what covering she had and resigned herself to having to work bare assed.

Work was slow at first, but when word got around about the waitress wearing only an apron, it became standing room only. At first she was mortified that all of these people were coming in just to stare at her ass, but when she had time to think, she had an epiphany. She had been trying to find a way to get better tips than Myrna and Stacey, now Myrna was having trouble keeping up. She thought about staging a wardrobe malfunction to test her theory. She pulled the apron a little extra to the left, and took a tray of food to a table of five. Instead of going around to serve the customers on the other side, she reached across the table to hand them their food, causing her right tit to fall out. She pretended not to notice and kept working, and started getting 40 – 50% tips. She had her new path to big bucks. She wasn’t an exhibitionist, she felt no arousal from her exposure. She was a capitalist.

On her nude ride home (the apron belonged to the bar and there it would stay) she started thinking about Stacey. Was she really the ditz everyone thought that she was or did she lose those bets on purpose? Maybe she wasn’t an exhibitionist like everyone thought. Maybe she had just found a simple way to make good money at a crappy job. She noticed that almost none of her bet losses cost her money, they just reduced her to little or no clothing. Was she a financial mastermind or just a ditz with big boobs surrounded by horny guys? Donna would have to pay more attention from now on.

Part 5

Donna knew that all of the clothing stores would be closed by the time that she got off of work, especially as busy as they had been today. Even though the money was good, she would much rather wear something skimpy than nothing at all. Although it was embarrassing, she did take some pride from knowing that much of it was due to men lusting after her. After life with her mom, being friends with Stacey, and working with Myrna, she wasn’t used to all of this attention
When she got home, she heard some noise from the back and went around to investigate. She found her mom enjoying a nighttime swim. Even though the sun had gone down, the heat radiating from the ground kept things pretty warm. Donna had built up a sweat riding home, even without clothing, and a swim sounded good. She asked her mom if she could join her, even though she didn’t have a suit. Her mom came over to the shallow end and replied, “Honey, we were all born naked. A bathing suit is only to protect your modesty, nothing else. Besides, I’m not wearing a suit either.” With that, she stood op revealing her nude body to her daughter. Donna was a little embarrassed by this, but couldn’t help but admire her mother’s beauty.

Donna jumped in the water and couldn’t believe how good it felt. Having nothing between her and the water felt wonderful. It was nice to not feel the suit drag as she swam and not having to constantly adjust it. Even though they lived of the outskirts of town with no visible neighbors, she had never even considered swimming nude. She asked her mom if she had done this before. Izzy just laughed and said, “Donna, the only time I bother wearing a bikini is when others are around, and that’s just so I don’t offend them. I mean, can you imagine if your friend Stacey’s mother saw us now. She would probably soil herself and pass out. Truth be told, I only wear clothes in the house for your sake. I don’t usually wear any when I’m home alone.”

Donna swam a few more laps and then went to take a shower. While showering, she thought about what her mother had just told her. All this time, her mother preferred to be nude at home, but wore clothing to keep Donna comfortable. After these last few days, that just didn’t seem right. When Donna finished her shower, she went and told her mother to wear what she wanted and Donna would just get used to it. She also told Izzy that she was proud to have such a beautiful mother. Also she wanted her advice picking out new clothes and told her about what she had learned today. Izzy laughed loudly and said, “Donna, sweety, did you think that I wear tight and revealing clothes to work because they’re comfortable?”

Donna went to her room and laid down on her bed. Tomorrow morning, her mom and her would take her tip money and buy her some new work clothes. Working nude wasn’t as bad as she had thought, but she wanted her future nudity to be on her terms, and in private. Thankfully this whole ordeal would be over tomorrow.
But you know what they say about the best laid plans…

Part 6

The next morning, Donna was awakened by her still nude mother holding the house phone. “It’s that girl you work with,” Izzy said with a concerned look. “She sounds upset.” Donna’s first thought was that Myrna was ticked that Donna had stolen her thunder, yet she knew Myrna wasn’t like that. Bewildered and still a bit groggy, Donna took the phone. On the other end, Myrna sounded frantic and maybe even crying.

“Donna, dad collapsed after work. The doctors say that he had a heart attack. They said it could be fixed with a simple surgery, but we don’t have insurance. We need money, but dad can’t work and I can’t open and run the bar by myself. Please come here immediately. I need you here as a worker and my friend.” Donna replied, “I was going to buy some clothes before work. Can I come there after I get some clothes?” Myrna said, “Donna, I need you here now! I’m at wits end and need someone here with me. You’ve always been like a little sister to me, and I have no one but dad and you. The other girls are too wrapped up in their own problems to care about mine. Besides, you worked with just an apron on yesterday and had your best tip night by far. Please come straight here.” Donna just said ok and resigned herself to another nude day.

She hung up the phone and filled her mom in. Izzy offered to drive her since it was her day off and she wanted to see if she could help the poor girl. She went to get dressed while Donna got up and ready. Twenty minutes later they arrived at the bar. They went inside and found Myrna with her head in her hands, sobbing, while the cook tried to console her. His name was Marko. He was a 5’ 10” Greek man in his early 50s who had been with her father since he purchased the bar. Many customers forgot about him, as if hot food just appeared from nowhere, because he was always in the back.

Myrna saw Donna, ran over and gave her a hug, and explained her problems. They needed a lot of money soon for the operation, far more than the bar made in an average month. Besides that, they had the usual bills to pay. Also, with her dad unable to work, they had no bartender. Myrna could handle beer and shots, but the only thing she knew about mixed drinks was how to order them. A bar simply could not run without a bartender.

At that moment, Izzy spoke up saying, “I tended bar for a few years when I was in my mid-twenties. I may be a bit rusty, but I think that I could do ok.” Donna looked at her and asked, “But mom, what about your job”. Izzy smiled and replied, “I’m tired of the drive and the crappy hours. This will let me work close to home and spend more time with my daughter.” With that, the bartending issue was resolved. They decided the best way to attack the money issue was to have a brainstorming meeting with all of the employees.

There were two other waitresses. First there was Skye, a 5’ 7” raven haired girl with small B cup breasts and with the nicest ass in the county. She always wore the tightest pans and the shortest shorts or skirts. She always made sure to bend at the waist to get good tips, and the guys loved it. She also looked kinda goth (not many real goths in the desert) with her black clothing and makeup. Also, somehow she managed to stay extremely pale in the desert (nobody knows how and are afraid to ask). The other waitress was Brandi, a bubble headed blond who made Stacey look like a genius. She was also a bit of a klutz, but at 5’ 10” with E cup breasts, she was always forgiven by the guys.

All the ideas were discussed, unfortunately most were from Brandi and were mind numbingly stupid. Whoever said there were no stupid questions obviously never met Brandi (i.e. Why do we have to serve alcohol?). After about two hours, everything was quiet. Finally, Donna stood up and said, “I have an idea, but I don’t know if any of you will like it.”

Donna told them of her epiphany last night while working only wearing an apron. Of course, she didn’t propose that all of them only wear aprons (which disappointed Brandi and Marko). What she did propose was a standing wager. There were two tables, one in each corner, that customers never wanted to sit in. They complained about waiting over 15 minutes for a waitress to notice them and take their drink order. These would be the “Hot Seats”. We get a doorman/bouncer to meet them at the door. To get in on the wager, they have to pay $10. That way, if we’re out of tables, someone can still sit there without wagering anything. Also, if they lose they get nothing. We keep the ten regardless. The doorman will give them a slip of paper with their time of arrival on it. If seven minutes (because it’s a lucky number) pass by and they have not been waited upon, they get an article of clothing from the first waitress to come over. These tables will not belong to any waitress, if you see someone sitting there, go ask if anyone has taken their drink order. To keep from having a situation where no waitress will go over in case it’s been over seven minutes, if it has been over 20 minutes, they take their slip of paper to the doorman or bartender. There will then be an announcement that all waitresses must give them one article of clothing. ‘’ I’m pretty sure tips will go up as you lose clothing and this will force us to be more attentive waitresses. Also, since this is Betting Town, if you end up overexposed, you won’t get in trouble because it’s part of the wager. I’ve been completely naked the past few days and there have been no complaints.”
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