The Thompson Family Traditions

Notice: All characters are of legal age.

Author's Note: There are many character's in this story, so, I've included an outline to help sort out any confusion. Also, special thanks to Heyall and Nom de Plume for help with editing.

The Thompson family

Wes

Patriarch. Early 50's. Husband of Helen

Helen

Mid 40s. Prim and proper wife of Wes.

Emma

Wes and Helen's youngest daughter. 19.

Matt

Emma's twin brother.

Jake

Emma's older brother. Early 20s.

Julia

Wes and Helen's oldest. Mid 20s. Brunette.

Others

Mary Ann (Grandma)

Helen's mother. Mid 60s.

Ben

Maryann's youngest. Helens brother. 50s. Uncle of Jake, Emma, Julia, Matt.

Natasha

Ben's daughter. 30s. Cousin of Jake, Emma, Julia, Matt. Husband is Freddy.

James

Julia's husband. 30s. Cuckold.

Mina

Jake's fiancé. Mid 20s. Taiwanese.

Ian

Emma's fiancé. 22.

Maurice

Thomson's butler. African American. 40s.

*

As Ian sat in the passenger seat of his fiancé's new Audi, he thought back on the past four years of their relationship. He and Emma had met in their sophomore year of high school when they had a class together. Now they had been living together for almost a year and it felt like they were already married. Married. Wow. And the big day was coming up fast. Ian shook his head to himself. He knew they were both still young, but those four years had gone by so fast. His high school sweetheart and best friend was a few months away from being his wife. He recalled feeling so intimidated about speaking to Emma's father Wes to ask his permission to marry.

Wes was a big burly man, a wealthy and powerful CEO, and since Emma had been distant from her family in the past, it had been awkward to approach him. But, despite still having distaste for her father, Emma and Ian had been making an effort to grow closer to the family, both knowing that having an in through the lucrative family business would be a huge benefit as newlyweds. Ian hoped he could help that continue. He appreciated how welcome they made him feel and looked forward to being part of their family and their business. And things were looking up, ever since the last dinner at Emma's parent's house, Ian had felt much more at ease.

Two weeks ago, He and Emma had joined her parents Wes and Helen for an evening at their home in the wealthy Edison district. Though they would occasionally meet up with her brother Jake and his fiancé Mina, Emma would rarely visit her parents or accept their invitations, but now, after they'd bought her the new car and offered to pay for their upcoming wedding and wanting to get a foot into their business connections, things had been changing.

Emma had given him an earful many times about how her father was all about money and an egotistical businessman stuck in his ways, but the truth was Ian respected that side of the Thompsons. And after his own parents had expressed so much disappointment in him not attending college, he was eager to get closer with the wealthy business family full of connections. But he understood how Emma felt about her family. He felt the same way about his own.

¬¬They had eaten dinner with her parents, served by their butler, Maurice, in a large and elegant dining room with a crystal chandelier, ornate colonial trim, and an oriental rug. The heavy mahogany dinner table decked out with a tablecloth, candles, and an artful centerpiece. Their house was ornate and rustic all at the same time.

Ian recalled the dinner, Emma's slightly bratty side coming out when she talked to her parents, occasionally bickering with her Dad. Yes, Emma had a bratty-ness. A small and very human flaw in an otherwise exceptional human, as Ian saw it, and it often came out around her family. Her father Wes, as far as Ian could tell, was a bit overbearing at times, but he admired that assertive nature more than anything.

At dinner, they had talked all about the upcoming wedding, which was to be at the Thompson's estate in a few months. Emma had been explaining to her father what she wanted her wedding to be like and after dinner the two left the room to discuss some of the decorations she wanted to be done around the house. As Maurice cleared the plates, Ian was left sitting with Emma's mother Helen.

Helen was a MILF with dirty blonde hair whose fitness and smooth skin was surprising for a woman of her age. She usually dressed quite formally around Ian but occasionally her demure dresses and outfits hugged her rear just enough to tempt him to steal a glance or two at her remarkably tight ass. On that night, she'd worn a black dress, cut just above the knees, that hugged her chest, and a neckline that was modest, but just low enough for Ian to find it tantalizing as she leaned forward to talk throughout the night. Now as she bent forward on her elbow, talking with just him, he tried to keep his eyes at an appropriate level, focusing on her cheery smile and bright cheeks.

"Ian," she said, "We're so glad to have you joining the family."

"I'm glad to become a part of it. I'm looking forward to meeting the cousins and everyone next time."

"Yes, the whole extended family has been quite looking forward to meeting you."

"Will the next family gathering be formal? Or more casual?"

"Oh, the family dinner will just be casual, grill some burgers out by the pool, then afterward will be a much more formal part of the celebration, but don't worry, a nice shirt and slacks will do. It's mostly Wes and I that will be dressing very formally. In our family, the engagement celebration involves a bit of tradition."

"Sure, that's fine" Ian knew they were a family with cherished history.

"Our traditions are unique to the family and we keep them close to the chest. They go way back, and you may find them a little strange, but they've been in the family for a long time and they've always been a positive thing for us"

Ian chuckled "No, I think that's great. I'm looking forward to taking part"

"Trust me" Helen continued "The family might weird you out, but Mina will be there too so you won't be the only fiancé, and if you stick through that, you'll find that you enjoy it -- er, them."

"Sure." Ian nodded.

Just then they heard Emma and her Dad coming through the hall toward the dining room. Helen and Ian smirked at each other; of course, they were bickering about something.

Emma was complaining "...they need to be up in both halls, it will look awful if they..."

"It will be fine. I don't know why it matters" Her father cut her off.

"So, how'd that go?" Helen Joked.

Emma rolled her eyes.

"Why don't we head to the drawing-room. I was just telling Ian that he will be introduced to some of our family traditions next time you come..."

Ian snapped out of his reverie, remembering where he was. He glanced at Emma driving the Audi. She didn't seem to notice that he'd been zoned out. He wondered what the traditions might be that Helen mentioned. They were just pulling up to the Thompson's house with its driveway full of nice cars. Ian was about to get out of the car but stopped as Emma spoke,

"Babe, whatever happens tonight...ugh. I hate my family. But... They're just different. We've got some traditions, especially surrounding when one of the family is engaged and gets married, but, just... I want this to work for us. I feel like I need to do this. Especially if I want to be invited into the family business. As much as they get on my nerves, they're my family and they will help look out for us as we get on our feet."

"Sure babe, no need to worry" Ian looked confused.

"Another thing" Emma added apologetically "They're gonna ask you to sign a prenup and... and some other papers tonight. I know we talked about it a while back, but I didn't want you to be caught off guard. My family is just protective, and anyone involved in the family business has to have their spouse sign one."

Ian nodded. So that's what all this weird tradition talk is about. he thought.

"It's fine, honey. I love you." he said, pausing. "I've got a family too; I know how they can be. It's not a big deal."

Emma gave a little sigh. "Yeah, if worst comes to worst, we can elope and never see them again."

Ian laughed as he opened the car door to get out. "I don't think we have to worry about that babe."

As they walked through the big front door, they saw that most of the guests were already there.

"Oh, there they are." Helen greeted them warmly.

"Hey, Mrs. Thompson. Jake. Mina. Hi." Ian replied.

"Hey, Ian!" Jake and Mina returned with big smiles.

Jake was a confident young man, sporting a pompadour haircut of nicely groomed dirty blonde. He was about Ian's height but much more fit. Ian noticed his arms looking muscular in his shirt. Mina, his fiancé, was the other fiancé whose engagement was being celebrated.

Mina was a second-generation American from Taiwan. A petite little thing, always smiling and a good sport. She was a bit shy, but it only seemed to compliment Jake's confident personality. Jake was the youngest pilot to pass through his air academy training in the history of the academy. Ian admired Jake, especially his brazen sense of style and always enjoyed spending time with them.

"This way, you two." Helen whisked Ian and Mina towards a side corridor.

Ian looked at Emma. She had a sheepish look. "I'll wait here." she said.

"Wes is coming right in. He's just working the grill." Helen said as Ian followed her and Mina into a small office. "Take a seat." she motioned to two leather upholstered chairs in front of a neatly organized desk.

"Ah, there you are." Wes said as he stepped in through a door on the other side of the desk, dressed casually in swimming trunks and a t-shirt. "Hello Ian, Mina." he shook their hands. "I'll get right to it so we can get back out there and have some fun."

Ian and Mina nodded. Ian thought he saw Wes take a glance down Mina's body. He shook the nonsense out of his head. This isn't a time to be distracted, he told himself

"We are so excited to welcome both of you into our family. I hope you feel welcome already, but after you officially become in-laws, ours will truly be yours. Our family has taken pride in its devotion to being all about the business. With it comes a lot of trade secrets and traditions. The business we run now has been in the family for six generations now as has the tradition that's passed down with that business. To be part of our family is to be part of our business. It's the core of our family. To protect that core, those traditions, we ask that you sign a few documents so that we can ensure that our secrets stay within the family. It's nothing personal. When our daughter Julia married her husband, James had to sign too, I had to when I married Helen, as did all the generations before."

Mina and Ian again nodded in acknowledgment.

"So, are what kind of involvement will we have in the business?" Ian asked.

"Well," Wes replied. "All of the extended family is invited to take part in the innermost workings of our company. Most start as lower management a work their way up over time, but there's always opportunity to jump ahead. It's not required at all, but if the interest is there, we always make a place for and watch out for our own."

Ian perked up his eyebrows. "That sounds cool." This was what he'd been hoping to hear.

Wes continued. "So I can go through and explain the documents if you'd like, or you can take a look at them yourselves, but we do need to sign before them we celebrate."

Ian spoke up. "That's fine, we can just take a look at them quickly I think." He glanced at Mina.

"Yeah" she nodded.

Wes handed them the papers "Great. Just sign where you see an 'x' at the bottom of the sixth page and on the last page as well."

Ian and Mina took the papers.

Thought Ian as he skimmed over the documents, trying not to take too long, hoping to give the impression that he didn't care about the money. Yep, this is the prenup, he thought to himself. He flipped through the pages briefly, ready to sign, but noticed Mina reading more carefully and decided to skim over it one more time so that he wouldn't look too brash. On his second pass, he noticed a section titled "Business Practices". This caught his eye and he skimmed over the bullet points. This is going to be great for me, he thought. He then carefully signed his name with the ornate fountain pen Wes gave him. First on the sixth page, then on the last.

"Ok, am I all set?" Ian looked at Wes and Helen.

Helen nodded and looked at Wes.

Mina, still reading carefully, looked up, embarrassed by her caution, and flipped to the last page to finish signing.

"Ok, all set." said Wes, taking the forms. "Welcome to the Thompson family. Let's celebrate. Come on around to the back."

Ian and Mina exited into the corridor and Helen and Wes went through the door behind the desk.

"Well, that wasn't so bad." Ian said looking at Mina.

"Mina looked down with a furrowed brow "yeah... but, did you...I just thought the NDA part was a bit strange."

"NDA?" Ian said with some surprise.

Mina looked at Ian. "Did you sign the non-disclosure agreement on the last page?"

Ian lowered his voice. "I... yeah, I did. I guess I didn't read it that closely though."

"It just seemed weird to me." Mina shrugged. They rounded the corner of the corridor into the living room.

Emma smiled at Ian. "Everyone's going out to the back." she said, feeling relief that he hadn't been scared away.

"Drinks for you guys?" Jake called from the bar.

"Sure!" They replied, and they all headed to the back patio.

"No butler tonight." Ian remarked to himself.

The back yard was a comfortable area with an in-ground heated pool and hot tub. There was a savory smell in the air as Wes returned to the grill where Ben, Jake, and Julia stood talking.

Ben was Helen's older brother, Emma's uncle. He was tall with a real dad bod, though not out of shape. Julia was Emma's older sister and the oldest in the family, and James was her husband of three years. Julia wore shorts and a tank top revealing her tight abs and huge tits. Emma had told Ian all about how her sister had gotten implants to boost her unsavory modeling career, but she looks great still, Ian thought. Julia's husband James wasn't particularly attractive, and was a bit less than shapely, a bit gangly even, and Ian wondered how he had scored such woman.

"Come let me introduce you to Natasha, she's Ben's daughter, you haven't met her yet." Emma said.

Natasha was sitting with her legs in the hot tub. She looked about in her thirties but she was shapely as hell, with big natural mom breasts, held in by a skimpy red bikini with bottoms that hugged her wide hips.

As she stood to introduce herself and they exchanged greetings, it was all Ian could do to keep his eyes above her shoulders. As she turned back to the hot tub Ian caught a quick glimpse of her cheeks. Her bottom was covered by only a string over her crack.

Emma's twin brother Matt and her grandma, Helen's mother, Maryann sat at the umbrella-covered deck table in conversation. Matt had a similar build as Emma. Thin and boyish. His face had quite a feminine look that resembled Emma too. He wore his trunks and sat, telling his grandma about his summer plans. Maryann wore a swimming skirt and top. For her age, her body was tight, though her silver hair and slight wrinkles around the edges of her eyes and mouth showed the signs of her weathered age.

Eventually, Helen came out to the patio and when Ian saw her, he couldn't help but let his eyes trace up and down her body. She was wearing a baby blue one-piece that hugged her mound tightly, showing the crease of her lips. Her thick, strong legs were sleek and shining and her ass was so thick it was practically spilling out the sides of the suit. But it was just as firm as it was thick and Ian marveled at her full and commanding tits. Though only the top of them showed, Ian could see they were smooth and firm. Even with the motherly hang of her cleavage, Ian could see that they were smooth and firm. Even Emma glanced at her mother's body a few times. The family greatly respected her for her well-maintained physique.

"You look great, Helen." Ben said.

"As she always does." Maryann chimed in sweetly.

Helen blushed.

"It turns out there's more than one who could be a model in our family," Wes smiled. "Helen's just too modest for it."

Julia rolled her eyes at the insinuation of her father's comment and looked to her husband James, hoping he'd saying something, but knowing he wouldn't.

"What?" James shrugged shyly.

Natasha smirked. "Especially after four kids. I don't know how you do it. I barely survived my two tots."

"Oh, Nat," Helen laughed. "I don't' think you have anything to worry about. You haven't changed a bit."

Natasha shrugged.

"So sweet of your Freddy to babysit them tonight too." Helen added.

"Well, he'd have loved to come if only we had found a sitter."

"Yeah, he's missing out." Matt joked.

Grilling and swimming, the evening wore on with conversation and laughter covering all topics. With the sun was just beginning to set, Ian was enjoying himself, taking part in toasts, talking with each in the family, but struggling the whole time to keep himself from indulging in too many looks at Natasha, Julia, and especially Helen.

Motivated by the thought of what they would think of him if they caught him looking, Ian tried to behave decently and continued the night, enjoying a few drinks. Mina was loosening up too, feeling more relaxed as the festivities went on. Wes was commanding in conversation and held people's attention well with his stories. Natasha was a bright personality who kept people laughing. Julia, a bit quieter, loved to talk about her career, while her husband just smiled. Jake, like his father, had a pompous personality and was joking around all night long, with some quips that Ian found surprisingly crude for a family gathering. Helen was so hospitable, always making sure everyone had what they needed. The whole family seemed so close. Helen sitting with her arm around Matt, everyone leaning in to share a story. Ian couldn't wait to become a part of that. He craved that kind of closeness.

Eventually, groups broke off in various conversations around the patio. Grandma was talking with James, Mina, and Matt by the pool. Ian stayed by Emma at the table talking to her parents. Wes and Helen were very open with their affection and at one point in a story, Wes even cupped Helen's breasts before she scolded him jokingly. But Ian's mind lingered on Helen's breasts until a loud smack made him look around to his left. Jake, Julia, and Ben were standing together, grinning, and Natasha giggled cupping her butt cheek and looking up at her dad.

Did... no... no, that couldn't be, Ian thought.

But not much later Ian saw Maryann put her hand on Matt's thigh, briefly rubbing her grandson's leg as he told her about something.

She's just comforting him. Consoling him, Ian told himself, just saying 'there, there now.'

Ian's thoughts soon moved on. He was just taking it all in, trying not to stare at Emma's mother and the beautiful young women around him. But he was surprised, multiple times, to find himself checking out Maryann and Jake as well. He wasn't sure what it was but something about their family left him feeling a little bothered. He'd never in his life looked at another man like that. He shook himself back.

Emma kept an eye on Ian throughout the night. She wondered what he might be thinking, what he was noticing. She noticed him shifting in his seat a few times. It made her worry. She couldn't help her mind racing about what was to come. She worried that he wouldn't accept her.