Win Lose or Strip
Exhibitionist & Voyeur Story

Win Lose or Strip

by Oopsydaisynaed 18 min read 4.2 (21,200 views)
bets voyeur
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Tim was returning to his hotel from a sales call. It had not gone well. On top of that, his boss Susan had been texting him repeatedly about some report she needed for a very important meeting. He had put it off and now he would have to work on it all night.

"Tell me you are going to get this to me this evening," she had texted.

"You'll get it when you get it," he thought, but did not actually respond.

More texts arrived. "Tim??" "Seriously!?" "I have to get this tonight!!" "Tim??"

"Screw you!!"

Tim just smirked. "You'll get it when you get it, Babe."

As he pulled into the hotel parking lot, he saw a space close to the front.

He sped up and then broke hard as he pulled sharply into the spot. This was an old stuntman trick that never failed to scare and impress the ladies. Only this time, it didn't go so well. In fact, the front left bumper of his car made contact with the front of the car in the next space. He got out and assessed the damage. He was happy to see that on his car there virtually wasn't any, just a little scraping on the bumper. The other car, however had a baseball sized dent.

"Why me," he groaned. It was going to be such a pain, finding the cars owner, trading insurance information, paying for the damage, not to mention what this would do to his rates. Ugh, he thought and he'd probably have to deal with that bitch Amy at the front desk.

Suddenly, he stopped and looked around. He noticed that no one was about.

"Hey," he thought, "if a car gets hit and nobody sees it, did it really happen?"

"Nope," he said aloud and promptly jumped in his car backed out and parked in another space on the other side of the lot.

Jen was gazing out of her hotel room window. She was sharing a room with Beth and Angie. She was waiting on them to finish getting ready so that they could all go down to the bar. She watched as a car pulled into the parking lot and pulled into a spot right next to her car. She jumped and let out a gasp as it slammed into hers.

"What's wrong," said Angie.

"Somebody just hit my car!"

"What!" Both girls rushed over and joined Beth at the window. They all watched as a man stepped out of his car, assessed the damage to both vehicles and then got back into his car and parked somewhere else.

"Well that little shit," said Beth.

"He is not getting away with that," said Jen. "You guys ready, let's catch him at reception."

Tim walked in to the hotel and sure enough there was Amy at the front desk. He also saw three attractive girls getting off the elevator and decided to impress them at Amy's expense.

"Did you get those extra towels sent up to 615 like I asked you?"

Amy looked confused. "Excuse me?"

"Should I take that as a 'no?'"

"Did you ask me to send extra towels to 615?"

"Well I asked someone. Don't you guys keep records? You should have a log or something."

"Yes sir. I'll make sure some get sent up there right away."

"See that you do. Oh, and have Debbie bring them up."

Jen, Beth and Angie got off the elevator just as their prey was walking up to reception. They decided that they would hang back and let him finish abusing the poor girl at the front desk before they pounced. As they continued to listen to him be so unpleasant to that girl, Jen had an idea. She didn't have time to explain it to the other girls, she simply slapped each of them on the thigh, short hand for "follow my lead."

She left Beth and Angie and approached the jerk. Instead of attacking him, Jen was all flirty and giggly. "She was so bored, the three of them had been on the road together for weeks, sick of the sight of each other, etc. etc. He seemed so interesting. Would he please join them in the bar soon for drinks?"

They were about to commence 'operation shit faced.'

Tim was excited. Three women. He liked his odds. Pick off the slow moving one, the weak one. God knows he liked his women drunk. Anymore, he thought bitterly, it was the only way he could get one, and even that didn't always work out.

He told her he had a few things to do upstairs, but they should get started and he'd join them soon.

After he jumped on the elevator, Beth turned to Jen and asked, "Okay, what the hell was that all about?"

"Well," said Jen, "I really am bored. And it occurred to me, we could have just had an ugly scene and maybe gotten some money out of him or we could have some fun and play him for the sucker he obviously is and still get some money out of him."

Beth and Angie new better than to argue the point. They were all part time poker players, but Jen was in a league all her own. As a matter of fact, they were on their way back from a tournament where Jen had cleaned up, raking in thousands to their hundreds.

This would not be the first time they had fleeced a guy who decided to "mansplain" poker to them.

"So we're going to get him to play poker?" Angie asked. "Yep," said Jen.

"How do you know he will, how do you know he even plays?" asked Beth.

Jen didn't answer, she didn't have to, she just gave them her patented "do you doubt me" stare.

She then pulled an unopened deck of cards out of her purse (she always had an unopened pack or three). She unwrapped the cellophane and took the cards out of the box, crumpled the box and then put the cards back in. Here, she said to Angie, take this to that poor girl at reception, tell her what we are up to and tell her to make it look good when the time comes.

Jen then ordered a pitcher of beer from the waitress. "I will happily pay for a whole pitcher," she said, "but bring us a half pitcher and four glasses please." When the pitcher arrived, Jen proceeded to pour what amounted to no more than a few sips into their glasses and filled one up for Tim. The waitress looked at what was going on and was not so sure that she approved.

Tim was pacing in his room. He was giving himself a little pep talk. This could work he told himself. Let them get drunk and then bring the drunkest one up here. Make out a bit, insist on turning out the lights and then with any luck he could get laid before she even noticed. He didn't know which one to root for, the pretty brunette who invited him, the taller red head who seemed to be shooting him daggers as he talked to the brunette or the busty Asian girl.

There was a knock at his door. He opened it and was greeted by a woman with a handful of towels.

"Here are your towels, Mr. Parker," she said.

"Debbie," he said, "call me 'Tim' and put them on the bed please."

He barely left enough room for her to squeeze by and then watched her walk over to the bed.

"I think I am going to get laid tonight," he said as she squeezed by him again. "Just say the word, though and I'll cancel my date."

Debbie didn't say anything. She just quickened her pace out the door and down the hall.

He laughed as he closed the door behind her.

He looked at his watch. About 20 minutes had gone by, enough time to give them a good head start on the drinking.

He was just about out the door when he remembered the report he had promised Susan.

And just like that, his phone buzzed. A text from Susan, "Where is my report?"

"Ah Susan," he sighed. "I don't think that's gonna happen." With that, he tossed his phone on the bed next to the towels and headed down to the bar.

They spent a little time getting to know each other. Tim lied and said that he was a director with a large paper distributor. He was in fact one of their salesman.

Jen lied and said that the three of them were drug reps just back from a reunion at their college sorority. Jen was indeed a drug rep. Beth, the redhead, was a receptionist and Angie worked retail. Although they had all gone to college, none of them had joined a sorority. Jen just figured it was the kind of thing a guy like Tim would like to hear. She was right.

Tim finished off his beer and suggested they get another pitcher. He also complained to the waitress that the beer wasn't very cold. The waitress suggested they switch to glasses of a beer they had on tap and on special. He didn't offer to pay for it, so it went on Jen's tab.

"Cool Beans," he thought. "Hot women and free beer, does it get any better than this?"

When the waitress saw whom these girls were trying to get drunk, her outlook changed.

This jerk had complained about every meal she had served him and used his displeasure as an excuse not to tip. Not only did she not care what they were up to, she would help.

They talked for a while about nothing in particular. Then Jen steered the conversation to favorite games they played as kids such as Clue or Monopoly. Beth, catching on, brought up card games like War and Go Fish.

"Of course as we got older, we played games like Gin Rummy and Hearts," said Jen.

"What about you Tim? She asked, as she signaled the waitress to bring them another round. She was impressed to see that Tim's beer glass was filled almost to over flowing, while theirs were as low as they could be without being obvious.

"Well the only card game I ever play is Poker."

"Oooh, poker," said Jen. "You know I fancy myself a pretty good poker player. I used to play with my little sister and win all the time."

"Uh huh," said Tim unimpressed.

Jen turned to Beth. "Do you play poker?"

"Umm, I have played before, but it's been awhile."

"How about you Angie?"

"No, not really," she said. "I had a boyfriend who tried to teach me strip poker once, but we just ended up making out instead."

And with that statement, Angie unwittingly changed the course of the evening.

Damn, thought Tim, playing strip poker with these ladies would be fine!

**

"You know," said Tim, "we should play some poker."

"Yeah," said Jen, "that sounds like fun!"

"No," said Angie, "that sounds stupid."

"Yeah," said Beth, "count me out. I'm too drunk."

"C'mon," said Jen. "What else do we have to do?"

"Well," said Beth, "that's true."

"Couldn't we just watch a movie or something," said Angie. "Besides, does anyone even have a deck of cards?"

"Oh yeah," Jen said, "good point."

"What about you Tim," asked Beth. "Don't all guys carry around a deck of cards?

"No," Tim said glumly, "not this guy anyway."

"Oh well," said Jen, "I guess we'll call it a night. It is getting kinda late."

"Hey," said Beth. "Maybe they have a deck at the front desk. You know, lost and found or something."

Tim sprang up, instantly regretted it, steadied himself and said, "I'll go check."

He headed to the front desk full of hope. He couldn't get the picture of three naked girls standing in front of him shyly trying but not succeeding to cover themselves out of his head. He barely even weighed the cost of losing. The odds were so in his favor. They were girls, they would be drunk girls and two of them barely knew how to play and the third one thought she was good because she could beat her little sister! Yep, this was worth the risk.

"Hey," he called out to Amy, "I don't suppose you have a deck of cards back there by any chance?"

"Excuse me?" she asked.

"You know, caaaards," he said drawing the word out and miming dealing them out.

"Oh playing cards."

"Yeah, what other kind of cards are there!?"

Another time, she would have given him a list.

"No," she said, "we don't sell cards here."

Exasperated, he said, "well I know you don't sell them, I just thought you might have complimentary decks or maybe some in lost and found (echoing Beth's thought)."

"Let me check," she sighed and trudged off through office door.

Behind the door, Amy beamed. "I did that really well," she thought. She waited another minute and then put a frown on her face and trudged back through the door.

"As a matter of fact, I did find a pack. They look kind of used. Is that going to be o..."

With that, Tim snatched them out of her hand.

"Great! This will do just fine."

"Yes! Score! Well, not yet, but soon!" He chuckled at his own joke. Then his lips turned downward as he thought of Amy's attitude. "I'm going to lodge a complaint about her before I check out."

While Tim was gone, the girls had the waitress empty their drinks and filled his up one last time.

"What are you girls up to," she asked.

They explained about the car and the way Tim had treated Amy and their plan to get restitution and teach him a lesson.

"Nice," she said. She dumped out their glasses and brought back the empties.

"By the way," she said, "I've been adding one of these to each of his drinks." And with that, she poured a shot into Tim's beer. "The shots are on me," she laughed.

He came back waving the cards in the air like he had just scored tickets to a sold out concert.

"Drink up cowboy," said Jen, "and then we can play some cards."

They talked/flirted a little more while Tim polished off his beer and then they headed up to the girls room.

"Great," thought Tim, "any room service will be charged to their room."

In fact, food was ordered along with another round of beers and then the card playing commenced. After a few hands that Tim won easily, it was suggested that they play for money. Angie argued against this, since as she reminded everyone, she was new to the game. Not surprisingly, Tim was also against playing for money. They expected this and had a plan to break down his resistance. But then Tim surprised them by suggesting that they play strip poker. This shouldn't have surprised them, but it did.

"Well," said Tim, "y'all think about it while I go take a leak."

While Tim was in the bathroom the girls talked. Again, the thinking was ultimately that this could end up being more interesting than just taking his money. And, a naked humiliated "mark" is probably less volatile than one who's just been fleeced, not to mention actually getting money from him was not guaranteed. No, this could be even better and there was even the potential for a little blackmail down the road, if he really pissed them off.

Still, in this day and age a little nudity among friends or strangers was not guaranteed to cause humiliation. It might even have the opposite effect. He was a jerk, but he wasn't bad looking. This thought was worrying Jen a little bit when Tim reemerged from the bathroom.

"Let's do it," cried Angie.

"Absolutely," said Beth.

Tim didn't say a word, but a shit eating grin spread across his face.

"Jesus," thought Jen, "if that's his idea of a poker face, this is going to be easier than I thought. I just hope it's worth it."

Now that stakes were involved, Tim's luck started to turn. After what seemed like just a few hands, Tim had lost his two shoes, his socks and his shirt. Angie had lost both shoes and a sock, Beth had lost her shoes, and Jen, well, she was fully clothed.

Just then there was a knock at the door and everyone jumped. Then they all laughed when they heard "room service."

"Loser gets the door," said Jen, looking right at Tim.

She frowned and worried a bit as Tim got up and wobbled to the door not the least bit embarrassed about the fact that he didn't have a shirt on.

Tim opened the door and there was Debbie. She said, "I have your order, shall I wheel it in?"

"Wheel away Debbie," said Tim, ushering her in with a sweep of his hand.

Debbie looked at the girls sitting around the table and the cards strewn about.

"Oh," she smiled, are you guys playing strip poker?"

"Isn't it obvious," sneered Tim.

"Actually," she said, "it looks like just you're playing."

The girls snorted at this.

"Care to join us," Tim shot back. "Entry fee is your shirt."

"Um, I'll just leave the cart since you guys are using the table," Debbie said, ignoring his comment.

She picked up one of the four beers and handed it to Tim. "Here you are sir."

"Look at that," he said, taking the beer. "Any excuse to be with me a little longer."

"No thought Jen, she just wanted to make sure you got the beer with the shot."

Debbie waited a beat in front of Tim and then rolled her eyes and headed for the door.

Jen muttered under her breath, got up grabbed her wallet and caught up with Debbie in the hall.

"Hey," she called out, "sorry about that," she said, handing Debbie a ten.

"Thanks," she said. "I hear you guys are going to teach this guy a lesson."

"Yeah," said Jen. "We were just going to take his money, but now we are planning to humiliate him instead."

"Oh good. I wish I could see it happen."

"Well," said Jen, "if we kick him out of the room naked, we'll call and give you a heads up."

Debbie just smiled and headed down the hall.

**

When she walked back in, Tim was halfway through his burger, while Beth and Angie hadn't really eaten anything.

"Yeah," thought Jen, "I've lost my appetite too."

She signaled over to Angie who got up and met her at the door.

Jen leaned over and whispered to her, "how would you feel about losing your shirt..."

Play resumed and Tim was buoyed as Angie went on a losing streak; her last shoe a bracelet (negotiated, Tim's watch would also count) and then her shirt.

"Oh my God, Oh my God. This is it," Tim thought. "Next hand and that bra comes off and I am a happy man!"

But it was not to be. Tim lost the next game and his watch. And then he lost again and to Jen's relief, seemed a little nervous as he peeled off his pants revealing a baby blue pair of boxer briefs.

He was breathing heavily as the next game started.

Okay, as soon as Angie loses another game and reveals those luscious ta-tas, I'll be the gallant gentlemen and suggest we stop.

But Angie didn't lose, Tim did.

"Wohoo the girls hooted. Take 'em off loser!"

"Okay," he said, "we've had fun, but c'mon I was never going to make you guys go all the way."

"Oh right," said Beth, "if Angela had lost that game you wouldn't have made her expose these?" With that Beth reached over and jiggled one of Angie's breasts.

"Hey!" said Angie, giggling with anticipation and slapping Beth's hand away.

Tim was struck dumb by the sight but then regained his composure enough to say, "I have to pee," and bolted to the bathroom.

"You're just delaying the inevitable," Jen called out.

"Shit, shit, shit!" Tim was cold stone sober now. The plan had been to get the girls drunk, enjoy the strip show—in his mind three naked ladies laughing and dancing around—until he took the drunkest one back to his room and had sex with her before she even had a chance to notice...and with that he pulled the elastic of his briefs away from his body looked down and sighed.

"So what now?" asked Beth.

"The undies are comin' off," said Angie.

"And then he dances and we film it," said Jen, holding up her phone, "and make him pay us to erase it."

They all laughed.

"Why do you think he is suddenly shy?" Beth asked. "I mean he has a pretty nice looking body. Nothing to be embarrassed about."

"He probably has a micro penis," said Angie.

"Oh my God," said Jen, "that's it! That makes so much sense."

"Yeah," said Angie. "Did either of you notice the lack of a bulge when the pants came down?"

Again there was laughter.

"Oh crap! They're laughing! Have they figured it out? This is bad," Tim thought. "What am I going to do? Wait, wait, I'm charming when I need to be. I can talk my way out of this."

With that, he started to unlock the bathroom door and then spied a towel on the rack.

He grabbed it and wrapped it around his waist and immediately felt better.

And then he didn't.

He was greeted by three fully clothed women pointing their phones in his direction.

"Uhuh," said Jen. "Towel off, undies off!"

"Now look," said Tim, all sweetness and light as he proceeded to go into his spiel.

Later, they had to admit he wasn't half bad. But c'mon, he never stood a chance.

At one point, Jen finally cut him off and led him over to the window.

"Look out the window Tim. Tell me what you see."

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