Andy Loses a Bet - Cover

Andy Loses a Bet

by Mad Stories

Copyright© 2024 by Mad Stories

Erotica Sex Story: Tabatha and Andy's marriage is on the rocks. As Andy's gambling addiction spirals out of control, Tabatha finds herself trapped in a web of broken promises and mounting debts. When a reckless bet with his friend Jacob pushes her to the breaking point, Tabatha decides to take matters into her own hands.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Fiction   Cheating   Cuckold   .

Tabatha and Andy’s love story began like many others—high school sweethearts who thought they’d found their happily ever after. They tied the knot young, full of hope and dreams for their future together. For six years, they navigated the ups and downs of married life, learning and growing together. Tabatha, with her warm heart and nurturing nature, had always been Andy’s rock, supporting him through thick and thin.

But lately, something had shifted. The once inseparable couple now felt like strangers sharing a home. Tabatha couldn’t pinpoint exactly when things started to change, but she noticed Andy coming home later and later each night, often reeking of alcohol. His mood had soured, and he’d become defensive, snapping at her whenever she dared to ask about his whereabouts.

At first, Tabatha’s mind wandered to the worst conclusions. Was Andy cheating? Had he found someone else? The thought made her stomach churn, but as she began to investigate, she uncovered a different, yet equally disturbing truth.

Andy wasn’t sneaking around with another woman—he was losing himself in the flashing lights and false promises of the local casino. Night after night, he’d sit at the tables with a group of buddies, throwing away their hard-earned money on games of chance. The alcohol flowed freely, numbing Andy to the reality of his mounting losses and the damage he was inflicting on his marriage.

The physical intimacy that had once been a cornerstone of their relationship had all but disappeared. Months had passed since they’d last made love, leaving Tabatha feeling rejected and alone. She longed for the tender moments they used to share, the quiet conversations, and the feeling of Andy’s arms around her. Now, she was lucky if he even acknowledged her presence when he stumbled home in the early hours of the morning.

As Andy’s gambling addiction tightened its grip, their financial situation began to crumble. Bills piled up, and Tabatha found herself picking up extra shifts at work to make ends meet. She tried to talk to Andy about their problems, but he’d shut down, refusing to admit that he had a problem.

This all came to a head one Sunday night when Andy invited his friend Jacob over to watch the game. Jacob, a die-hard Dallas Cowboys fan, arrived decked out in his team’s gear, ready for some friendly rivalry with Andy, who staunchly supported his hometown Jacksonville Jaguars.

“Good to see you, please come in!” Andy said as he greeted Jacob at the door.

“You ready to lose?” Jacob joked with him. He wore his Cowboys jersey and knew it would get a reaction out of his friend.

“Nice jersey!” Andy said.

About six couples showed up. Their mutual friends, Mark and his wife Tina, along with a few others Jacob was meeting for the first time. All of them were Jaguar fans.

“Jacob, you are outnumbered today!” Tina joked.

“It’s okay. I’m good with it.”

Everyone was drinking. The game was exciting. The couples were all in their twenties or early thirties.

“Sorry bud, but the Cowboys are losing today!” Andy said at the end of the first quarter. The Jags were up seven to three.

“There’s a long way to go in this one. I’m not worried, the Cowboys will win!”.

“No way.” Andy shot back at me. The others were all encouraging him to stand up for their team. After all, they were up early in the game and playing well.

“Watch and see!” Jacob said.

“I’ll keep watching, but what I’ll see is the Cowboys losing.” Andy started playing up for the crowd.

“I don’t think so, but keep on talking if it makes you feel better.”

“Jacob, you want to put some money on it?” Mark asked as Andy’s face lit up.

“I don’t want to take your money, Mark.”

“How about five hundred dollars?” Mark asked.

“Whatever, do you even have five hundred?

“Well, not on me, but of course I have it,” Mark said. Jacob knew Mark made a good amount of money so he wasn’t really worried about it.

“So do we have a bet?” Mark asked.

“Sure, we are on. Five hundred it is. Winner takes the money.” Jacob told him.

“I want in on this too,” Andy said all too quickly, already showing the signs of a slight buzz.

“You want five hundred too?” Dannu asked looking around for Tabatha as he knew Andy had a bit of a problem and he could get a lot more out of it.

“Unless losing one thousand is too much for you?” Andy joked.

“Ha, that’s nothing. I’m game for much more if either of you wants to go more.”

“Mark is fine at five hundred!” Tina quickly answered.

Careful Tina, we don’t want to cut into your shopping money!” Jacob joked, hoping to keep the mood light.

“I’m not scared to go more,” Andy said. “I believe in my Jags and I’m not scared to back it up!”

“Okay, name an amount.”

“Let’s move that five hundred to five thousand!” Andy said.

“Oh shit! That’s a big jump!” Jacob said shocked it had escalated so quickly.

“Andy, that’s stupid. It’s too much.” Mark told him suddenly, shying away. Andy didn’t care. He had faith in his team, plus they had the lead. If we won this it would more than cover his recent losses and restore some order back in his life.

“The Jags are winning. I feel it.” Andy told Mark. “If you all are smart you would get in on this free money.”

The other couples laughed it off and all declined to get in on any bets.

“Okay then, we have a bet!” Jacob told Andy just as Tabatha was walking back into the room from the kitchen.

“What is going on in here?” Tabatha asked as she entered the room.

Jacob watched Tabatha’s facial expression turn to shock and then anger as the group told her of Andy’s bet. You could clearly see that she was not happy with what had happened and her emotions were quickly getting the best of her.

“Andy, can I speak with you privately please,” Tabatha said her face red with anger.

“Not now, the second quarter is about to start,” Andy said, somewhat brushing her off. She had enough of this behavior. He has brushed her off one too many times, and she practically dragged him into the other room by his arm.

“Now please,” Tabatha said again.

They left the room for a few moments, but in reality, they could have just stayed there. They were talking loud enough that everyone could hear them arguing anyway.

“Andy, we don’t have to bet,” Jacob told him as they returned to the room, both red with anger as neither wanted to back down from the other.

“No, a bet is a bet. We are on.” Andy said much to Tabatha’s dismay.

“Okay, but just remember, when the game is over, I gave you a chance to back out,” Jacob told him.

The Cowboys had a great second quarter and led the game at halftime by the score of twenty to seven. Andy and Tabatha had another talk at halftime. She was clearly upset with him and looking for a way out of this.

The Jags made a run in the second half. Andy started the trash-talking backup as the game got closer. It was a twenty-three to sixteen lead for the Cowboys and the Jags had the ball.

“Lawrence is going to win this for us! I bet you are the one regretting that bet now!” Andy said as confident as ever.

“Well, I was actually feeling bad and was going to let you out of the bet, but since you are so confident, I’m holding you to it,” Jacob replied as he watched Tabatha out of the corner of his eye.

“When the Jags win, I’m holding you to it!”

Tabatha sat on the couch too worried to even enjoy the game. The only reason Jacob even considered letting him out of the bet was because he felt bad for her. She was a very attractive woman and someone he had a crush on for a long time. She was wearing a Jags shirt a black leggings. He wished the shirt didn’t cover up so much of her gorgeous chest, but at least the leggings showed off her ass.

“Sorry, Tabatha. I was trying to let you two out of the bet,” he told her as she shifted uncomfortably.

“I know. I can tell. Andy will have to deal with a very upset wife if he loses this stupid bet.” Tabatha said.

“Fuck!” Andy yelled as Lawrence threw an interception.

The room went silent for a few moments. Jacob looked over at Tabatha, who was white as a ghost. He knew they didn’t have the money to pay, and unfortunately so did she. The game was over and the Cowboys won.

“Jacob, I’ll pay you tomorrow,” Mark said as the party started to wind down and everyone left.

Jacob wasn’t sure how he was going to handle asking for the money. It was awkward when they were all leaving. Andy and Tabatha had a nice home, but it was obvious they didn’t just have five thousand lying around to just throw away. He left and decided not to mention the money just yet.

He woke up the next morning to a text from Tabatha “Can we talk?” He didn’t need to ask why, he knew exactly what it was about.

They agreed to meet at her house that evening. When he arrived, Tabatha was dressed differently. She had on a little skirt and heels. He had never seen her dressed up and it took him a minute to register Andy was even in the room. Her chest was on full display in her short low-cut crop top and the skirt made her legs look even better than he remembered. He swallowed hard trying to think of anything else at that moment as he felt his cock swell in his jeans.

“I’ll get right to the point, we don’t have five thousand dollars,” Tabatha said. All Jacob could do was nod in reply. He knew that was the case, but at the moment all he could do was stare at her chest and legs.

“Andy is very sorry about the bet. He was drinking and the emotions got the best of him.” Tabatha said. I could tell that she was very much in charge at this point, as Andy was sitting in the corner looking at his feet.

“I understand, but I have just one question. If Andy had won, would you have expected me to pay you?

“Of course, I would have,” Andy answered before Tabatha had time to reply. She shot a look at him that would have killed most men on the spot, and in that moment Jacob was happy he wasn’t on her bad side.

“Andy, stop talking,” Tabatha said clearly frustrated.

“Okay, so had I lost you would have expected me to pay up. You lost and you don’t have the money. You are now asking how to settle this. Does that sound accurate?” Jacob asked.

“Yes. We are asking if there is anything else or another way we can work this out. We just don’t have that kind of money at this time.” Tabatha said, touching his arm softly and doing her best to put on the charm.

“What are you thinking?” Jacob said the blood once again flowing to his dick.

“I don’t know. Is there anything you need? Andy is an excellent handyman. He can do repair work on your home or something like that.”

“Hey, I don’t want to do that man’s bitch wo...”

“Andy I said shut the fuck up! You’re the reason we are in this mess in the first place. If your limp dicked ass could just keep your mouth shut maybe we wouldn’t be in the situation we are in” Tabatha shot back daring Andy to speak again.

“I don’t need any work done. I mean, I really can’t think of anything.” Jacob said calmly, trying not to get her anger cast his way.

“There has to be something. Anything, you name it. Andy will agree to it and will work every weekend that he needs to make it up.”

“How much of the five thousand could you give me now?”

“Maybe two thousand. But that includes the money we have in savings. It would leave us with nothing” Tabatha answered with a hint of remorse in her voice.

“Well, all your savings. I’m not that cruel.”

“We know we are in a bad spot. Is there anything you need or could use instead of the money? It is Christmas time, maybe you can find it in your heart to work something different out.” Tabatha asked.

Jacob could tell Tabatha was getting emotional. She dressed up to impress him in hopes he might find her attractiveness a reason to go easy on them. She seemed so mad at Andy, he had never seen someone’s wife talk to them like that. He couldn’t stop looking at Tabatha’s legs either. If he thought she was sexy before, she looked like a supermodel now.

“Well, now that you mention it, there is something,” he said as Tabatha’s face brightened.

“Anything, you name it!”

“Like you said, it’s Christmas time. I have an office Christmas party on Saturday I must attend. I don’t have a date.”

“Okay, so what are you asking?” Tabatha replied.

“Well, I need a date.”

“With my wife?” Andy blurted out looking not happy about the request.

“Andy, shut up, no talking. I’m handling this.” Tabatha told him coldly.

“Taking you on a date is not something you are doing,” Andy said.

“Andy, you got us into this, I’ll do whatever the hell I please. Now let me handle this,” Tabatha said.

“Hey, you asked, I’m just making a suggestion,” Jacob said, holding up his hands and backing away.

“Okay, so you want me to be your date for your office Christmas party?”

“Yes. I work all the time. I’m single and I need a date.”

“What else?” Tabatha asked.

“What the fuck, you are considering this?” Andy blurted out.

“Andy, I swear to God, if you say one more thing!” Tabatha quickly told him.

“How about Andy also shovels the drive this weekend?” Jacob said with a grin, enjoying seeing his friend squirm a little.

“I meant what else was on the date, but yes, Andy will be happy to shovel snow,” Tabatha said.

“Well, I don’t want people at my work thinking I invited my sister or something out as my date. So you would have to play the part.”

“Play the part?”

“You know, dress up, do everything you would do on a normal date,” I said.

“Play the part, let me think,” Tabatha said, looking over at Andy.

Andy and Tabatha stepped a few feet away and were discussing. Jacob couldn’t hear every word but he did pick up on Tabatha mentioning how Andy likes to show her off. Andy tried to explain how this was different. He wouldn’t be there to monitor and dressing up wasn’t the same as going on an actual date with someone. Tabatha told him it was time to put up or shut up. It was obvious Andy did not like this plan, but Tabatha had already made up her mind.

“Okay, we have a deal,” Tabatha said. “What time do I need to be there on Saturday?”

“I’ll pick you up at seven. And by the way, it’s a nicer event, not tux or anything like that, but still semi-formal.”

“I will make it work.”


As Tabatha dressed for her date with Jacob she was hit with a sudden since of guilt. “Am I taking this too far?” she wondered as she slid on her long black tight dress with a very high slit going up her thigh, and a deep V around the neck. She looked in the mirror, studying herself. But then she remembered Andy’s dismissive attitude, his broken promises. Her jaw set with determination. She was going to do this. Andy needed to squirm a little.

Jacob arrived at seven on Saturday evening, his heart racing with anticipation. As Tabatha opened the door, he was momentarily stunned. She wore a long, form-fitting black dress with a daring thigh-high slit and a plunging neckline. The sight of her took his breath away.

“You look ... incredible,” Jacob managed, trying to keep his composure.

Tabatha smiled, a mix of confidence and nervousness in her eyes. “Thank you. Shall we?”

As they prepared to leave, Andy appeared at the foot of the stairs, bundled up in winter gear. His face was a mask of barely concealed resentment.

“I’ve finished shoveling your driveway,” Andy said flatly, addressing Jacob. “And I’ll keep an eye out for any fresh snowfall.”

Jacob opened his mouth to protest, but Tabatha cut in smoothly. “Andy insisted on doing this. It’s the least we could do, given the circumstances.” Her tone left no room for argument.

Jacob nodded, deciding it was best not to challenge the arrangement. As he offered his arm to Tabatha, he couldn’t help but notice the pointed look she gave Andy – a silent exchange that spoke volumes about the state of their marriage.

“Thanks for doing this,” he told Tabatha as he gave Andy one last look then hooked his arm with hers.

“No, thank you for working with us and allowing us to do this instead of the money.”

“I will admit, I didn’t think you would get all this dressed up for this evening. You look absolutely stunning” he told her as they walked to the car.

“Well thank you. It was the least I could do. Andy is not going to be happy when he finds out how much I spent on this dress and these heels. I wanted to look good for tonight, so I splurged. It’s still so much less when compared to what I would have spent if we paid up though.”

“You look amazing! It was money well spent. I almost feel bad knowing I’m going to be accompanied by the prettiest woman there considering you’re another man’s wife.”

“I told myself I would enjoy the evening. Andy needs to learn his lesson. When I get home tonight hopefully we will be remorseful!” Tabatha said. “I really need him to learn his lesson.”

“Well, in that case, I’m glad I could help.” Jacob teased.

As they entered the venue, Tabatha felt a mix of excitement and nervousness. The room was elegantly decorated, with twinkling lights and festive garlands adorning the walls. Soft jazz music played in the background as people mingled, their laughter and chatter filling the air.

Jacob placed his hand gently on the small of Tabatha’s back, guiding her towards the bar. “What would you like to drink?” he asked, his eyes meeting hers.

“A glass of white wine would be lovely,” Tabatha replied, feeling a slight flutter in her stomach at his touch.

As they sipped their drinks, Jacob introduced Tabatha to his colleagues. She found herself relaxing, enjoying the easy conversation and the admiring glances she received in her stunning dress. However, her moment of peace was interrupted by a buzz from her purse.

Excusing herself, Tabatha checked her phone to find a text from Andy: “How’s it going? When are you coming home?”

Irritation flared within her. She quickly typed back: “It just started. I’ll be home when it’s over.” She silenced her phone and rejoined the conversation, determined not to let Andy ruin her evening.

“Would you like to dance?” Jacob asked as the music transitioned to a livelier tune.

Tabatha nodded, setting down her glass. As they moved to the dance floor, she felt a surge of confidence. This was supposed to be a date, after all, and she was determined to play the part convincingly.

They started with a respectable distance between them, moving to the rhythm of the music. As the night progressed and more drinks were consumed, their dancing became more intimate. Jacob’s hand found its way to Tabatha’s waist, and she didn’t shy away from his touch.

During a break between songs, Tabatha felt her purse vibrate again. Sighing, she checked her phone to find three more texts from Andy:

“This is ridiculous. I said I was sorry.” “How long do you plan to punish me?” “It’s not fair that you’re out with another man.”

Tabatha’s jaw clenched as she read the messages. She reminded herself that it was Andy’s reckless betting that had put them in this situation. His lack of accountability only fueled her frustration.

Noticing her frown, Jacob leaned in. “Everything okay?”

 
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