Pretty Please
Taboo/incest Story

Pretty Please

by Rob_royale 17 min read 4.6 (67,000 views)
in-laws father-daughter mother-in-law family affair mature big tits sister group sex
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This is a work of fiction. Names, characters, events, and incidents are the products of the author's imagination. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are over the age of 18.

Hello again. Just a heads up, this story features adult child/parent incestual sex and partner sharing/swinging. If that is not your jam, then please move on to greener pastures. This ordinarily wouldn't be mine either, but comments on a forum thread on the subject got me thinking and I decided to cross that line. And I figured if I was going to cross that line, I was really gonna DO it. This is a family affair.

Pretty Please

Tim would have bet money that he had the most unusual family. But recently his new fiancé Kayla had made him realize that those odds weren't as good as he'd thought.

***

Kayla cleared her throat. "So, babe ... there are ... some things I think I should tell you about my family."

Tim glanced briefly at his new fiancé as he drove. "We're twenty minutes from their door. You're bringing this up now?"

Kayla smiled abashedly. "Well yeah. It's kinda hard to talk about. So, I've been ... procrastinating."

Tim frowned. "All right, I'm listening."

She rubbed her arm absently. "So, umm ... my family is wealthy."

He glanced at her again. "Well, I sort of figured that. We're driving to Cocoa Beach. You can't buy a sandcastle there for less than a half-million."

Her voice took on an irritated edge. "And how would you know that? Did you look that up? Maybe see how much my folks are worth?"

Tim frowned deeply. "As you know, my family has lived here in Florida, between tours, for my whole life. So, you'll forgive this southern yokel, for knowing about where he lives," he said tersely.

She sighed. "I'm sorry. It's just that ... well ... they aren't just wealthy. They are incredibly, stupidly, absurdly wealthy."

Tim threw on his directional, pulled into a gas station, and rolled up to a gas pump. After starting the pump, he sat down behind the wheel and looked at his lovely fiancé. For the ten thousandth time, he was struck by her beauty. She was classically pretty with high cheekbones, a tiny nose, big full lips, and pale skin. Her straight black hair shone in the sunlight.

"Okay, let's hear it."

Kayla squirmed in her seat. "My grandfather on my dad's side was a successful businessman. He started a construction company and did very well. Dad followed in his footsteps, building the business, and investing heavily in East Coast real estate."

Tim whistled. Forty years ago, the land was cheap in Florida. But not today.

She looked down at the floorboards. "I didn't tell you because ..."

Tim held up his hand. It had taken him about three seconds to figure out this mystery. "Nope, I get it. How would you know if my feelings for you are real, or just an act to get a wealthy wife, right?"

When she looked at him there were tears in her eyes. She put her hand gently on his forearm. "I'm sorry. I'm so sorry. I know you love me. I know it."

He couldn't help feeling a bit hurt, but he did understand. Seeing it from her perspective, it would be a constant doubt in her mind. He leaned over and kissed her tenderly. The gas pump handle clicked shut. Tim secured the pump and got back in. "So how did you go from that life to being an orthopedic nurse with RB?"

Kayla shrugged. "Mom and Dad raised Coral and me so that we knew that they weren't raising a couple of useless rich bitches like the Hiltons. We had to get educated and get jobs, move out on our own, and become useful people. Our trust funds don't kick in until we're forty-five. Grandpa did the same thing with Dad and my Aunt Lori."

Tim was impressed. That was a very blue-collar mentality. As Tim pulled his used Toyota out of the gas station, he smiled. "So, anything else I should know about your folks?" In the year he'd known Kayla, she'd been remarkably close-mouthed about her parents. He only knew they lived on the East Coast and were in real estate. He'd proposed two weeks ago with his family around but hadn't yet met hers.

Kayla took a big breath before replying. "Umm ... yeah. My parents, they're umm ... nudists."

***

Tim's parents were the most unlikely pair. His mother was an acrobat and tumbler from Romania. Tim had inherited her lovely Mediterranean skin tone and dark hair. His father was a juggler and clown from Texas. They met and fell in love under the lights and excitement of the Ringling Brothers and Barnum & Bailey Circus. Tim was raised there, traveling with his parents and wintering in Sarasota, Florida with the rest of their extended circus family.

Like all the circus kids he'd been mostly home-schooled with support from Ringling Brothers, including tutors and equipment like PCs and textbooks. He'd completed his education at sixteen. His parents had trained him in both their specializations and though he'd enjoyed clowning and tumbling, they weren't really his thing. At the age of sixteen, he was working as a roustabout, helping set up the three rings and everything above them. He helped wrangle the animals, helped the clowns suit up, and helped in any way he could. He loved circus life.

Surrounded by so much cultural diversity he picked up a working knowledge of Russian, Spanish, German, and a bit of Mandarin, on top of his mother's native Romanian which he spoke fluently. It all just came naturally to him. He turned eighteen in early 2017 and shortly thereafter lost his virginity to a beautiful Chinese contortionist, who spoke about ten words of English. She'd taught him so much that night, in positions that defied the Kama Sutra. It turned out that two English words she knew well were "fuck" and "good".

Later that year, life changed drastically for the troupe. Low attendance combined with animal rights protests had the company in dire straits. Ringling Bros. performed its last show in New York City. Afterward, the troupe returned to their winter quarters to lick their wounds.

***

"We're not done, Tim," Jack the talent manager, assured him and his parents. "The company has plans to roll out a brand-new show in about five years. Without animals. Just extraordinary people like your parents." Tim's mom had long since stopped performing and had become the head trainer for all the Ringling acrobats.

Jack looked him in the eye. "We're going to find work for your mom and pop and you ... we'd like to send you to college. We're going to be scouting the entire world looking for amazing people. We're going to need someone who can teach them fluent English. With your already impressive language skills, we'd like that person to be you. You're family."

Tim hadn't given much thought to a college education.

Jack laughed. "I'm told there is already a young Chinese woman whose English has remarkably improved due to your tutelage."

***

Four years later Tim returned to the troupe with an AA in English, a BA in creative writing, a CELTA certificate for teaching English as a second language, and fluent in American Sign language thanks to a lovely blonde he'd dated his junior year.

Four years of scouting had been wildly successful, and the training grounds were full of new people and their families. New trailers dotted the grounds. Tim had more work than he could handle.

One day, he was carrying one of his mother's tumblers to the medics for a sprained ankle, when he first laid eyes on Kayla. The dark-haired young woman spotted them coming into the clinic and her look of concern turned to a delighted smile when she noticed Tim. Their instant attraction hadn't taken long to become something much, much deeper.

***

"Nudists?" Tim said incredulously.

Kayla giggled. "Yep."

Tim's mouth gaped. "How long has this been going on?"

She smiled. "All our lives. Coral and I grew up that way."

Tim frowned. That explained Kayla's penchant for wandering their apartment nude most of the time. It drove him crazy. "Will they be ... umm?"

"Nude when we get there? No, they will be clothed when we arrive. They know you aren't used to the lifestyle."

Tim breathed a sigh of relief. "We're staying for a week. Will we be expected to ...?"

She giggled. "To get with the program? Yes. Definitely."

He'd long since gotten used to Kayla finishing his questions for him. "Whoa boy," he whispered under his breath.

"C'mon, it won't be that bad. You do it just fine with me at home," she said with a lascivious grin.

"Ugh. You like it when I walk around with a hard-on. I doubt your mother will."

He was so caught up in his thoughts, that he completely missed that she didn't reply.

***

Tim's heart was in his throat when the front door opened. The house was a modern masterpiece of architecture built to withstand hurricanes and look great doing it. He could hear the surf on the beach side of the house and could smell the sea. An ornate wrought iron fence surrounded the front of the house. Towards the rear of the home, it turned into an eight-foot stucco wall for privacy.

A tall, lean, and tanned, older man clad only in a blue Speedo, opened the door. His wide smile was genuine and welcoming.

"Daddy!" Kayla rushed past Tim, leaping into her father's arms.

The man swept her into his arms and spun her around in a circle. Tim stepped into the home.

"Kayla, sweetie!"

Tim looked past his fiancé and her father, and his breath caught in his throat.

Years ago, his father had told him, "Boy, if you want to know what your wife is going to look like at fifty, then take a hard look at her mother."

When Tim laid his eyes on his future mother-in-law, he knew he'd hit the jackpot. Kayla was five foot seven and curvy enough to turn heads wherever they went. Her mother was all that

and

a bag of chips, so to speak. Her frame was more Rubenesque than Kayla's, slightly shorter, with lovely big breasts at least two sizes bigger than her daughter's, perhaps more. Her hourglass frame was nicely tanned, and her generous curves were barely covered in a red thong bikini.

"Ah hell," Tim thought. "Clothed when we arrive, my ass."

Kayla rushed to embrace her mother.

She turned to Tim. "Mom, Dad, I'd like you to meet Tim. Or Timotei as his beautiful mother calls him. Tim, these are my parents, Mark and Catherine.

Mark extended a big hand. "Glad to finally meet you. She's been gushing about you for so long. I'm sorry it took so long to get you kids out here.

Tim used one of his favorite jokes, "Well it's a real circus back home."

Mark laughed and it was genuine. Tim smiled. Catharine stepped from her daughter's arms and approached Tim with her arms wide. "We've been so looking forward to meeting you. We hope you'll be comfortable here."

Tim did the best he could to ignore the feeling of her big tits pressing into his body as she embraced him. "Call me Cookie, sweetheart. Everyone does." As he pulled back to smile at the beautiful dark-haired woman, he spotted her earrings. His gut clenched up.

He tried not to let his unease show. "Thanks for having us, Cookie. You have a lovely home."

She held him at arm's length and smiled brightly at him, before glancing back at her daughter. "Can you imagine, she's twenty-four years old and only now brings us her fella?"

Tim saw his fiancé frown. "Well, she was waiting for the right one," Tim said with a grin.

Cookie embraced him again with a bright laugh. "I'm sure you're right. I love a confident man."

She turned and stepped toward her daughter. "Honey, guess what? Coral and AJ will be here on Monday, and she has a surprise!" Kayla brightened and the two women walked off into the kitchen together.

Mark clapped him on the shoulder. "C'mon, let's get your bags out to Granny's apartment."

Granny's apartment was a separate one-bedroom in-law suite connected to the back of the house by a covered walkway. A door in the sunroom led out to it. As Mark told it, it had been built for his mom, but she hadn't lived very long after moving in. So, it became a guest suite.

***

Tim turned to Kayla with a frown as they unpacked. "You didn't tell me everything, did you, Dragă mea? You left out a couple of very important little factoids, didn't you?"

She flinched. Dragă mea was a Romanian term of endearment that meant darling. Ordinarily, she loved it when he called her that. "You saw her earrings?"

"Well yeah babe, she hugged me twice. Hard to miss them." He'd nearly passed out when he'd seen Cookie's gold upside-down pineapple earrings. "You haven't traveled with the troupe yet, but when you do you will find a few trailers with magnetic pineapple decals. Your parents are nudists

and

swingers."

She nodded glumly.

"And you really should have mentioned that your mother is a complete fox. I was expecting a greying housewife with a mom-bod."

Kayla's head snapped up in surprise.

He continued, "A total babe that very shortly will be walking around this house in nothing but those earrings and I'm going to be expected to walk around naked as if it's just another Saturday."

"I'm sorry. I just didn't know how to say it so that it wouldn't freak you out."

"Listen, I'm no prude. You know that," he said calmly.

She nodded. It was true. Sexually speaking they were perfectly simpatico.

"It wouldn't have freaked me out, I don't judge people. It's just that I would have liked some processing time. That's all." In truth, his biggest concern now was being able to be around Cookie without imagining her bent over the end of the couch, and him sporting a boner the whole time.

Kayla sighed. "Listen. I grew up this way. It is expected that you are going to get an erection, at first. Trust me, no one is going to pay any mind at all. They are used to it. After a couple of hours, you'll get used to it and it won't be an issue after that. You'll see."

She stepped back and looked at him appreciatively. At five foot ten, he had a wonderful stocky frame, with broad shoulders and thick arms. "C'mon, you literally grew up surrounded by beautiful women, showgirls, and acrobats dressed in tights, body suits, and leotards. You got used to that, right?"

Tim shrugged and nodded.

She walked up to him and kissed his jaw. "Besides, I think that if can keep your balls empty, you might have less of an issue." Kayla's right hand slid down, and he gasped as her delicate hand slid into his shorts and caressed his hardening cock. She gazed up into his dark brown eyes. "Do you think that would help you, iubițel?" Kayla purred in his ear. Iubițel meant lover in Romanian.

Tim looked down and kissed her roughly. When she broke the kiss, she smiled and pulled her hand from his shorts. "Whoa there, tiger. Tonight, I'll be your happy little fucktoy. But now I'd like to go spend time with my folks."

Tim grinned, breathing heavily. "I'll be looking forward to it."

***

The couple shared sexy smiles and more kisses while they dressed. He watched her put on a tiny yellow bikini with a deep yearning in his eyes. How he loved and lusted for this woman. She made his soul burn; unlike any other woman he'd ever known. Her womanly figure was so different and enticing. He could never get enough.

"Here, I bought these for you," Kayla smiled as she handed him a black pair of men's bikini shorts.

"You're serious?" Tim replied doubtfully.

"Yes. Put them on. It will help you get more comfortable around my folks because like it or not, tomorrow the clothes come off."

He rolled his eyes. "Ugh. This has turned into a nightmare."

She watched approvingly as he slid the tiny swimsuit on. Tim's work in the circus had kept him in terrific shape. He admitted that he'd gotten soft while away at school, but his mother Alina got him quickly back in shape. She insisted that he work out with her acrobats whenever he could. "We cannot have you walking around like the rest of these soft American slobi, can we?" She took the obesity problem in the U.S. very seriously.

Tim spied himself in a dressing mirror. "Oh hell. Look at my tan lines. It looks like I'm wearing white shorts under the Speedo."

To her credit, Kayla didn't even crack a smile. "Don't worry about that. We have all week to get some sun on those buns."

***

Tim was very self-conscious when they walked through the back door into the sunroom. They walked into the kitchen together where her folks were preparing supper.

"There they are," Mark said as they walked in. "Hey, you guys look great."

Kayla smiled and kissed her father on his lips.

Tim blushed a bit. "Thanks. You can thank my ..." Tim's voice faltered a bit when he saw Cookie visibly admiring his body, with a sly smile. "Drill sergeant of a mother. She keeps us all performance-ready."

Cookie came around the island counter. "I'm looking forward to meeting your folks. Do you think they'll be put off by our lifestyle?"

"I ah ... I'm not ... sure," Tim said frankly. "Mom is very proud of her body, and I doubt she'd mind very much, but Dad is a bit more old-fashioned. Mom keeps him in good shape, but he doesn't even like to take his shirt off around other ladies in the troupe." His dad, Cort, had grown up on a Texas cattle ranch, six hundred miles from the nearest beach. "I'm sure Mom could talk him into it, though."

Cookie smiled and glanced at her husband. "Yes, we usually can."

***

Dinner was prepared to be transportable and easy to eat. The two couples packed the picnic basket and walked it and some chairs down to the beach. Tim had been all over Florida and was amazed to see waves big enough that you could ride on a surfboard.

He looked at his fiancé. "Do you have surfboards?"

Kayla nodded; her mouth full of shrimp salad. She swallowed and smiled. "Do you surf?"

Tim laughed. 'No, but I've seen Point Break fifteen times. I'd love to give it a try."

She nodded. "Maybe tomorrow, okay?"

They spent that evening chatting happily. Talking about their relationship and wedding plans, life with the circus. Tim was very careful to make sure he focused on Cookie's face. Twice he'd let his attention wander to her ample curves and had to cover himself with his plate as he felt his cock begin to stiffen.

They talked until the sun began to set and the mosquitoes came out in squadrons. They hastily packed things up and headed for the climate-controlled safety of the house.

Back in the kitchen, Cookie looked at her daughter and said loud enough for him to hear, "Will Tim be okay tomorrow?" It took Tim a moment to catch on, then he remembered. Tomorrow the tiny bathing suits would be gone.

Kayla smiled. "I think he should be okay after a while. I plan to fuck his brains out first thing in the morning, so his cock should behave itself."

Tim choked on the soda he was drinking. Everyone smiled as he recovered. He wasn't used to hearing such talk out in the open. Especially around family. But this was clearly no ordinary family. Seeing Kayla and her mother so close together he was struck by the comparison. Kayla had inherited her mother's dark hair and eyes. Curls in Cookie's case, straight and lustrous in Kayla's. She'd also inherited her mother's obvious good looks, but she was leaner, and a little taller, more like her dad. But the curves remained. Tim felt himself begin to get hard again and turned from the group.

"No promises."

***

That evening, Tim stepped into the big bathroom in Granny's apartment. He inhaled sharply when he saw his woman in the tub. She'd shaved her legs and at that moment was sitting on the side of the tub beginning to shave her pussy as well.

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