Breaking the Family Ch. 01

Jack was right that this could ruin him. And all he had was my word. I hadn't signed anything. I wasn't local either. I had no skin in this game, but he was all-in.

"Okay Jack, I will take your deal, but with some new conditions."

Amanda's grandfather leaned back in his chair now, his glass on his chest, and smiled like the dealmaker he was.

"I agree to take over for Edward as the stud bull for the family. One of the women wants a kid, I will deliver."

Daniella chuckled at my analogy.

"But I have my own conditions."

"1. Amanda is kept in the loop on everything. Any requests for semen donations go through her first. We don't do things behind each other's backs."

Jack nodded at this.

Amanda had worn a skirt, and I started to stroke her thigh above the knee as I continued.

"2. I don't want to just be brought into the dealership. I want good jobs for Amanda and I both. I want equal equity to your kids in the company, and when you retire, I want the first chance to be #1."

I saw the three sons all jolt at this request. I guess they all thought it would be them.

"Don't worry, I want to keep it in the family. I just want an equal seat at the table."

Jack didn't even glance at his sons as he nodded again.

"3. I want access to every woman in the family. After I get done putting a baby in her", I said, pointing to Amanda. "And then her", I pointed to Daniella now, "I want to test out every other woman that Eddy either had or made."

The room was deafeningly silent now. Amanda didn't know I was going to make this request, so she was frozen in my arms. She even brushed my hand off her thigh.

Jack sat up now, leaning toward me.

"Exactly what do you mean, son?"

I sipped the Scotch again, and set it down.

"I want sexual access to your daughter, daughters-in-law, and granddaughters, real or acknowledged. Once they are of age, of course."

Jack leaned back now, whistling. All eyes in the room were on him, except Amanda, who was focused on me.

"Even my mom" she blurted out.

I shrugged. I hadn't thought about her, but I didn't want to rule her out.

Jack leaned forward, eyes trying to drill holes through me.

"That's a big ask, son. How am I supposed to agree to that?"

I stared back, maintaining my composure, resisting my urge to pee myself.

"Well, Daniella's here. Melanie and Erica have a lot to lose, so they should agree. As for the grandkids, as long as you give me the green light, Amanda and I should be able to make that happen."

Jack saw I couldn't be intimidated. He turned to Daniella, who was almost laughing at my bold request. Of anyone, she had the least to lose.

"Well, this was your idea. You see the barrel he has us over now?"

Daniella chuckled now, letting it out. "Sorry Jack. I should have just gotten him drunk, dragged him to a room, and gotten it out of him that way."

Jack slapped his knee, laughing back. "I think that's how Melanie got Eddy the first time."

He turned back to me, still chuckling.

"Kid, I hope that whatever grandkids and great grandkids you give me will inherit that giant pair of balls you got. I ain't been fucked this bad in a negotiation since Grandma Rose talked me into having him" he said, pointing to Donald.

This was the cue for everyone else to laugh, and the tension in the room melted.

"Okay, I can't put #3 in the contract, at least not directly, but my lawyer should be able to say you can fuck whoever you want in a roundabout way. Shit. That's a good ask. There are some gorgeous women out there. I assume that's it?"

"Nope, I do have a #4. I want this bottle of Scotch."

Jack laughed, and motioned to Anthony, who came back with the bottle. I saw it only had an inch left in it.

"That's your first fuck-up son. You spent too much time looking at the women, and not enough time looking at the bottle. I'll split what's left with you."

He poured us each a healthy pour, we clinked glasses, and sipped another taste of what had to be a couple hundred dollars of whiskey.

"Alright, Charlie fucked us good. But none of this leaves this room. I will talk with each woman when the time is right. For now, no one says anything to anyone."

The heads around the room nodded.

"Okay son. What say I fill you in on how selling cars works. Mandy, you can stay too if you want. The rest of them should have either learned this by now, or never will."

With that, Amanda's father, uncles, and Daniella all left the room. We spent an hour with Jack, drinking and talking. He gave me a crash course on the car business, and increased Amanda's knowledge too. I did my best to listen, but my mind wandered to the order in which I wanted to pursue all of the lovely women of his family. With the many gorgeous women to choose from, I knew this was going to be even more exciting than seducing Amanda's bridesmaids.

It took two months for Amanda and I to close up our old life and start a new one in her hometown. We quit our jobs, bought a new house, and moved ourselves and our dog out near her family.

With the change in zip code, and our healthy new incomes, our new house was huge. With all the extra space, our stuff barely half-filled it, and each weekend we did a little more shopping.

Work at the dealerships was a lot more exciting than my old job. Jack, true to his word, took me in as his #2, and I had spent time at each dealership, getting to know the staff and learning the business.

Jack presented this as bringing in his granddaughter's 'whiz kid' husband to help the business, and while there were whispers of his retirement, the employees didn't seem to hate me too much. Or at least they were kind of enough to do it behind my back.

On the home front, Amanda had thrown out her birth control the minute we left the house on Thanksgiving. We continued to fuck like rabbits, and week ago she passed a pregnancy test. The test was confirmed by her doctor a few days ago, which is why I was now pulling up to Donny and Daniella's house to pick up the missus. As Amanda had demanded, I had knocked her up first, so now it was Dr. Daniella's turn.

Amanda and I had talked, and I had the go-ahead to seduce Daniella without Amanda there. Our hope was that her aunt would come around for a threesome, but we realized that wasn't the agreement. I also had the green-light to fuck Daniella from now until she was definitely pregnant, no checking in with Amanda. That gave me a little spring in my step as I headed out that morning.

While Daniella had known each for years, it was in group social settings. She had asked for some one-on-one time before we did the deed, so I decided to treat this as a first date. Daniella and I were both golfers, so I suggested a round to break the ice. Saturday morning was the first time our schedules lined up, so here we were.

While I was treating this as a date, I wasn't sure what Daniella was thinking. But as she strode out of her house towards her garage, I was very much convinced she was, in fact, trying to seduce me.

It was a little bit chilly, with a mist in the air. My wife's youngest aunt was wearing a tight, form fitting golf jacket, and her jet-black hair was tied back in a ponytail that stuck through the hole in the back of a baseball cap.

What caught my attention though, was the short, tight white skirt she was wearing, which covered less than one-third of her long, olive legs. It showed off her athletic figure, and when she turned into the garage to get her clubs, I saw it also highlighted the slight protrusion of her butt.

I fixed my growing hard-on in my pants and got out to help her load her clubs into my car.

We exchanged pleasantries, and I could see she seemed a little nervous. I assumed that was from the fact that the plan was after our round of golf, she might be cheating on her husband for what I assumed was the first time.

I didn't press her, and kept it light. I decided if she wasn't going to take the lead and seduce me, I would make an effort, so I chivalrously loaded her clubs and held her car door.

We chatted on the way to the course. I had only seen Daniella a couple of times since our agreement was struck, and never alone. We caught up on life by the time we reached the course.

The sun was out by the time we got on the first tee, and it quickly warmed up. I stripped my coat off to take my first shot, and after I drove, I saw Daniella doing the same.

Under her golf jacket she wore a tight, gray polo shirt that showed off her athletic physique. Luckily golf could be played with a hard-on, because I expected to have one all morning.

To her credit, Daniella didn't seem to be actively teasing me, but it only took until she putted in on #2 and went to pull her ball that I saw that her panties were also white.

While Daniella was quiet at first, the ice broke as the day warmed up. As we walked back to the cart to put away our drives on #8, the subject of the day finally came up when I told her that Amanda was showing her first symptom of her pregnancy.

"It's early for nausea, isn't it?" She replied.

"I don't know. Between trying to keep up with Jack and remembering where my golf clubs were packed, I haven't opened the book she assigned me."

Daniella laughed, and responded:

"Yeah, it shows. I think I am beating you by about a dozen strokes."

"Well as a doctor, I assume you are out here every afternoon."

"Oh c'mon, this is the first time I have been out on the course in weeks."

"I know, it shows. You almost missed that last putt, while I have missed everything longer than three feet."

Daniella laughed again, and I went back to my story.

"And no, it wasn't nausea. As Amanda and I were... intimate yesterday, she found that her breasts were very tender. She said that was her first symptom."

We were standing next to each other at the back of the cart now. Daniella turned towards me to respond, pressing her body against mine.

Her sultry tone was a complete reversal from everything else to this point.

"I hope that means she didn't wear you out."

I leaned over and whispered in her ear now, turning so she felt my hard-on against her body.

"Trust me, I would be more than happy to bend you over this cart right now, flip up that sexy little skirt you are wearing, and show you how little wear I have gotten."

I pulled away now, and finished with my club.

We played #9 in silence, my comment hanging over our cart like the humidity. #10 was backed up, so we pulled off for a bathroom break.

As Daniella got out in the cart, she finally retorted.

"Well, I hope you do that better than you golf. Otherwise, I may need to take a mulligan."

As I watched her sashay into the clubhouse, drawing almost every eye as she did, I decided that I needed to defend my honor, both on the course and in the sack.

I wasn't lying to Daniella that my golf game was rusty. With the move and the new job, I had managed to get to a driving range a total of two times. But that didn't mean I was a bad golfer.

Since swimming was only a winter sport at my school, I had joined the golf team in the spring. Four years of being on the course every day during golf season, plus whatever time I could get each summer, meant that I wasn't a bad player. In fact, I could tell on the last few holes that the rust was finally off.

As Daniella came back to the cart and handed me another bottle of water, I pitched my idea.

"So, how about we made these last 9 holes interesting."

"How so?" she asked, getting in next to me.

"How about we play this skins style?"

"And what does the winner get?" Daniella sounded cautious, but interested.

I shrugged, hoping to lead her where I was going. "I guarantee that I can't keep up with you on money bets."

Daniella nodded. "What can you keep up with me on?" This time I heard a little flirt in her voice.

"How about, the loser has to flash the winner?"

"Wow Charlie, that's kind of a big ask, isn't it?"

I shrugged in response. "I thought since we were going to end up there anyways, why not make the journey interesting. Plus, you said yourself you beat me badly on the front nine. Who says you will lose?"

I saw her thinking about it. "Okay, but no showing the same thing twice, and each area of clothing counts as one."

"That works for me" I responded.

Daniella looked me over and counted. "Shoe, shoe, shorts, shirt. Four items, since hats and gloves shouldn't count."

I looked her over, slowly, like a piece of meat, and said the same. "Leg, leg, tits, ass. Four items."

I saw Daniella blush a little, probably realizing for the first time what she agreed to.

I continued. "And if someone runs out of flashes, then the winner gets to decide when, where, and how we do it the first time."

Daniella smiled now. "Aww, how sweet you'll let me decide on our first time."

We shook on the bet, laughing, and went to the 10th tee, which had finally opened up.

#10 was a long par four. Since the ladies tees were farther up on the par fours and fives, I always went first. I pulled out my driver and headed to the tee. So far today I had not really used my driver, as I wasn't able to control it at the range. However, now that there were stakes involved, it was 'go big or go home'.

I took a quick warmup, stepped up, and absolutely blasted one straight down the fairway. I don't think Daniella realized how far I hit the ball, because she didn't react, but I knew I had killed it. We drove up to the ladies' tees, and she drove as well. A nice strike, but even with her 'head start', I saw her ball had not caught mine.

As we pulled up to her ball, she finally spoke.

"Okay, this is the first time all day you outdrove me. Are you hustling me?" Her voice was playful.

I feigned confusion. "Just a good shot, I guess."

The rest of the hole proceeded from there. I just missed being on in two, but I chipped close, and sunk the putt for par. The good doctor two-putted, and bogied.

When we got back to the cart, I could see her competitive side kicking in. She did not want to lose another hole.

"Okay, how do we do this?" she asked, clearly fuming a little. I guess she thought I was a pushover.

"Well, let's start with one leg" I smiled, waiting.

Daniella untied one golf shoe, then her sock. Standing in front of the cart, she put her bare foot up on the cart, her knee out to the side at a ninety-degree angle while pushing down on her skirt with one hand to keep her modesty. It almost seemed like a model's pose, exposing her long, tan leg. Her face was defiant as she did so.

I smiled at her. "Very nice. Hope to see another one soon."

"Oh don't count on it. I beat guys at golf all the time."

The next hole was a short par 3. Our tee-off locations were closer on this hole, so I got lined up while my wife's aunt did as well.

My irons were the weakest point of my game today, so I said a silent prayer and then swung. My aim wasn't good, but I got a friendly bounce and was on the green.

Daniella hit a good shot, and landed on the green, closer than me.

We complimented each other, and drove up. I lined up my putt and hit. It was too far away to really line up, so I just wanted to get close. Lucky for me, I had found the line, and my ball fell in the cup as it went by.

I heard Daniella swore behind me as she watched. She didn't have a short putt either, so she lined her putt up, and struck. It looked like it might go, but ended up a couple feet short. My playing partner let off another couple expletives, and marched back to the cart, leaving me to put the flag back.

When I got there, her other leg was already exposed. I smiled, nodded, and she put her cleat back on.

We drove in silence to the third tee, another par four. As I slowed the cart to a stop, I put a hand on her thigh.

"We don't have to continue the bet if you don't want to. I wanted this to be fun."

Daniella took a deep breath, and replied "No, it's okay. I just get competitive, and then I get frustrated when I lose."

"Okay" I said, getting out and moving back to my bag. I pulled out my driver again. The tee box was on Daniella's side of the cart, so instead of going around the front, I slid past her, letting her lightly feel my cock against her ass as I did. It was quick enough it might have seemed like a mistake, but I saw her start after I did.

Daniella walked up to her tee box as I lined up and drove again. I wasn't going to take it easy on her, so I swung big again. This time I had the length, but not the accuracy. It was 50/50 whether it stayed on the fairway.

I went back to the cart and pulled up next to Daniella. She was lining up her shot. She had a nice little butt-wiggle when she did so. However, I am pretty sure she threw a couple extra wiggles in for me this time.

She hit a better drive than me, and when we pulled up we saw I was out in the rough. I had to lay up short, while Daniella's second shot left her with an easy chip.

My chip was excellent, and we both ended up with easy putts for par. Walking back to the cart, I could see she had calmed down a little.

"So how would we do it?" She asked.

"Huh?" I replied, confused.

"If one of us has to show more than a leg. How would you not flash the entire course?"

I smiled back. "There are always blind spots on a golf course. Not to mention a couple steps into the woods and no one will see you. But I thought you said that wouldn't happen."

"Oh, I just wanted to make sure you were thinking about where you were going to show me your dick, that's all."

We both laughed at that.

#13 was a long par five, and after three shots each, I was on the green for an easy putt while Daniella was still a good chip away.

She chipped over the green to the other side, and swore.

I was at the cart getting my putter, and called out "Do you want to concede this one?"

She shook her head. "Hell no. You want these", she said, pointing to her chest, "You have to earn them."

Before she could go over and chip again, I calmly walked onto the green and sunk my putt. Standing over the hole, I saw her staring at me, arms crossed.

"That was bad form" she said.

I shrugged back. "I got excited"

We walked back to the cart now and put away our clubs. I could see her confidence lagging. There was a cluster of trees just past the green, so I pulled up behind them. Taking a long look around, I couldn't see another cart or person.

"Ok, pay up" I said, smiling.

She smiled back, still angry, but living up to the terms of our wager. She grabbed her hem and pulled up, catching and lifting her bra along the way.

I had seen Daniella in sports bras before. She and my wife shared pictures all the time. I have to say, the sports bras did a masterful job hiding her breasts. Free of their containment, they sprung out to say 'hi'. They were tan, just like the rest of her body. They sagged a bit, but for their size, which looked to be around D-cups, they were magnificent.

I stared, forcing her to finally lower her shirt.

"Okay, I think you have seen enough for now. When you're done drooling, we have five more holes to play."

With three wins in four holes I got a little overconfident on #14, and ending up losing for the first time after I had two bad putts. Maybe a hard dick only hurt my putting.

I calmed down and was determined to win #15. That would give me three holes to 'play with' if we went past flashing. As I said earlier, Amanda had cleared me for penetration, so I was ready to go if Auntie was.

#15 was another par three. Daniella and I both hit the green with our first shot. My putt was a little farther, so I putted first. It was not a gimme, but I read it correctly and sank it (like I hoped to do to her soon).

That put all the pressure on the gorgeous doctor. When she putted, I thought it was in, but it came up short again.