Andy loses a bet

Tabatha and Andy were highschool sweethearts and married for 6 years. Tabatha loved Andy very much, but it felt like lately they were drifting apart. He was coming home later every night, usually smelling of alcohol and would often get very defensive when she asked where he'd been. To top it off, they hadn't had sex for months. At first she thought he was cheating on her, but as she began to investigate she realized he was at the casino almost every night. He would go there with a group of friends, bet on games and get shit faced before coming home in a sour mood because he lost his money. This all came to a head one night when Andy invited his friend Jacob over to watch a football game. Jacob is a huge Dallas Cowboys fan, while Andy preferred his home team the 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 want 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 on getting 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 all 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 back up 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 coach 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 laying 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 would have 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 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 power washes my deck and siding this weekend?" Jacob said with a grin, enjoying seeing his friend squirm a little.

"I meant what else as on the date, but yes, Andy will be happy to power wash your deck and siding." 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."

Jacob picked Tabatha up at seven that Saturday. She greeted him at the door wearing a long black tight dress with a very high slit going up her thigh, and a deep V around the neck. The moment Jacob saw her he knew he was going to have a very hard time keeping his hands off her all night. As they were preparing to leave Andy came downstairs, dressed like he was going to the gym. Before Jacob even had a chance to ask, Tabatha chimed in.

"Andy is going to spend the day washing your deck. I also told him he needs to make sure there are no weeds in the garden and the garage is cleaned out." Jacob wanted to say none of that was necessary, but given the look she shot Andy he knew the decision was already made.

"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 would have paid up though."

"Well, you look amazing! 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.

When they got to the party, Jacob was right. All eyes were on Tabatha as they walked to their table. As the drinks started to flow and the band started up Tabatha noticed Jacob was holding back a little. It was clear to her that he was holding back, presumably because he was with his friend's wife.

"Please, treat me like you would any other date. A deal is a deal. I don't want you leaving tonight and thinking we still owe you" Tabatha said with a certain fire in her eye.

"Okay, let's go dance!".

Jacob took Tabatha out on the dance floor and tried to liven things up. With the drinks flowing, and the music pounding in their ears they slowly worked their bodies closer to one another. Tabatha bumped her hip into Jacob as she let her fingers run through her hair. It was obvious she was out to have a good time and wasn't going to let the night sour. Before long, Jacob had his hands around her hips as they swayed to the beat together. He was close enough now, he could smell her hair, and her scent was intoxicating. He let his hands wander along her hips and across her thighs, before the song changed and Tabatha spun around to face him. His hands suddenly on the curve of her ass.

"I love this song!" Tabatha yelled in his ear, getting even closer as her thigh brushed against his cock. They stayed like that for what felt like an eternity, until Tabatha again spun around and pressed her ass against his now very hard cock. He let his hands wander across her hips to her stomach, inching closer to her chest, something he had only been able to fantasize about. Tabatha reached down and squeezed the side of his thighs letting him know she wanted to be that close, as his face was on her neck. As they continued their dance, the intoxication of her scent was too much for him to handle and soon he was kissing her neck as his fingers traced the outline of her chest.

Tabatha quickly turned around. He was afraid he had crossed a line and soon he was going to see her wrath. Instead, as they were face to face she grabbed behind his neck and pulled him in for a kiss on the lips. Soon they were making out like a couple of horny teenagers, grinding to the beat of the song as their tongues explored each other's mouth.

"I can't believe I'm doing this." Tabatha said after finally coming up for air and leading him off the dance floor.

"I'm sorry, it's my fault. You are married. We just went too far. It was a mistake." he told her, afraid the night was about to come to an end.

"Well, I am your date after all. That was the deal, right? To treat me like you would any other date?" Tabatha asked, holding his hand as he saw the wheels spinning behind her eyes.

He was shocked at what he was hearing, but he was so turned on he could barely think straight.

"Are you sure about this? I can pretend this never happened. I can drive you home." As he searched for a way to let her out of the situation they found themselves in, she stopped him in his tracks by once again pressing her lips to hers. She moaned softly into his mouth as his tongue flicked out and he ran his hand through her hair. His own inhibitions quickly melted away.

"You know, they gave us all a room for the night." He said as they broke their kiss. His eyes searching hers for what to do next.

"Really? Show me." She said, biting her lip.

He took her hand and quickly raced toward the elevator. He wasn't sure if he was rushing because he was afraid she would change her mind or because he thought he would change his. Regardless of the reason, as the elevator doors opened he practically dragged her inside as his lips once again found her neck. Tabatha moaned softly as her purse began to buzz. We both ignored it, as the elevator slowly made its way to the 11th floor.

As we burst into the room, her purse began to buzz again and this time she broke the kiss. "It's Andy. He won't stop calling. I need to answer it." Tabatha said as Jacob layed on the bed staring at the ceiling.

"What do you want?" Tabatha hissed as she answered the phone and slipped her shoes off.

Jacob couldn't hear what Andy was saying, but Tabatha was in charge of the conversation. He seemed very concerned about how the date was going.

"Fine, FaceTime me and you can see for yourself!" Tabatha said and hung up before once again giving me that look.

"Hello honey!" Tabatha answered sarcastically. She had Andy on FaceTime so they could see each other. Tabatha walked to the other side of the hotel room to take in the view while talking.

"I have on this new black dress." Tabatha said as she lowered her phone to show Andy her dress giving him a little spin for good measure. "Jacob has taken great care of me tonight." She added, giving him a wink.

"And how much did you spend on that?" Andy asked.

"Not five thousand!" Tabatha shot back. Apparently Andy was completely in the dark about her outfit and the price tag it came with when Jacob picked her up today.

"I guess that's fair. Look, I really am sorry about all this. Please just come home and we can start over." Andy said.

"Oh, and here are the new heels. Now, they are expensive!" Tabatha said, lowering the phone down. She pushed her leg out of the slit in her dress showing off her legs in her heels.

"Wait, Where are you?" Andy asked as he realized her background didn't seem like that of a party.

"Oh, I had to use the restroom so we went to Jacob's room for a quick break. It also has more privacy than the rest room down stairs." Tabatha answered a bit of mockery in her tone.