Chad and Rachel

Chad has been with Rachel since before I was born. He's 55 now and she is 54, but she is a very hot 54. I don't even remember their wedding, but I was the ring bearer.

They are very well off. Chad is a successful investment banker and Rachel a Real Estate Agent. She looks the part too. 5'9", short black hair, glasses over her blue eyes. She always looks sophisticated and in control. She has a very nice, curvy body. Closest I can compare her to is Lynda Carter in her prime.

Rachel has that "I'm better than you" attitude, and I was looking forward to putting her in her place. Plus I've always wanted to fuck her.

I arrived at their house and knocked on the door. Chad opened the door, he sighed "How much do you need?"

Not even a "hello brother", "How are you?", nope right to money. now I do owe them about $4000, so I can't totally blame him... but I will.

"Actually Chad, I am here to pay off what I owe you."

"Really. You know you owe us $3950, right?"

I walked in, pulled out an envelop and handed it to him "So $5000 should cover it."

He took the envelop, looking shocked. He opened it and counted it. "Can I grab a beer while you count?"

He didn't look up, still counting "Sure, behind the bar."

I walked into his "Man Den", which was off to the side and bigger then my apartment. It was a fully stocked Man Cave, just not in the basement. I went behind the bar and grabbed a beer, then sat on a stool while he finished counting.

"Well, I have to say, I am surprised. Where did you get the money?"

"I've turned things around and money is no longer an issue."

"Job?"

"Kind of, more like investments."

"You mean gambling. Fuck Kevin, when are you going to learn. You may have won a little money, but in the end, you will lose it all."

"Not this time. Where's Rachel?"

"Book Club. She'll be home in about an hour."

Both their kids were moved out, so I knew it was just us for now.

"How about a game of pool?" of course he said yes and when Rachel walked in the house, I had won my $5000 back, plus another $500.

She walked into the room, looked at me "What's he doing here?" What a bitch.

"Actually, he came to pay us back the money he owes us?"

"Really, all of it?"

"Plus interest. $5000 total."

"I'm surprised. Where is it?"

"Funny thing, we played some pool and I kind of lost it all back to him."

She rolled her eyes and shook her head at Chad "I thought you told me he could never beat you at pool?"

"He can't normally, but today it's his day."

"Fine, I figured we would never see that money again anyways. I'm going to bed."

"Wait, the night is young, stay and hang out?" I said

"No thank you." she turned

"How about a bet." She stopped and looked at me

"What kind of bet?"

"You play pool too, right?" she nodded.

I walked up to the table, took the 7 solids and tossed them randomly on the table. Then I put the 8 ball near a corner pocket. Lastly I put the Cue ball about a foot away.

"Ok, you are stripes, I am solids, you shoot first."

She looked confused, "All I left to do is sink the 8 ball?"

"Yes. I still have to sink all my balls. You win, I give Chad back the $5000, plus the $500 he lost and I give you $1000 more."

"Great. What if I lose?"

"Then you hang out with us all night, until I say the night is over..."

"Deal"

"Wait, there's more. I choose what you wear. I will pick something from your room and you have to wear it all night.

"Deal!" she didn't hesitate. She grabbed a cue stick with confidence, walked up to the table, lined up her shot "8 Ball, corner pocket" She had a Fuck You smile on her face, pulled the stick back and put the Cue Ball right in the pocket.

"What the fuck? How did I miss that?"

Chad was stunned. "Let's go upstairs and pick out your outfit."

She slammed the stick on the table "Fine."

We walked into her room, she pointed to the closet. "Go ahead, perv."

I walked in, looked around, and pulled out thigh high, high heeled boots and handed them to her.

"Are you kidding. I never wear those. Chad got them for Valentines day one year. More a gift for him."

"Oh, did they come with something else."

"Yea, slutty lingerie that I only wore that night."

"Perfect. Put the boots and that lingerie on, meet us downstairs.