Category: Incest/Taboo Stories

A Mom & Son Affair: Accidental Orgy

by silkstockingslover©

Summary: A secluded beach leads to a wild kinky day for mom & son.

Note 1: This is a Summer 2016 Contest story.

Note 2: This story is inspired by the stories thread and REDBAY for the original story thread and MELLO, SIXTYNINE for the plot summary that led to this story... which stimulated a lot of ideas as I tried to create this lengthy, fun, summer story of incest and much, much more.

Note 3: Thanks to Robert, Dave, Wayne and Tex Beethoven for editing this story.

A Mom & Son Affair: Accidental Orgy

As Mason put on his bow tie to go with his tux, his Mom, Lily, walked into his room dressed in the beautiful red dress she had bought just for this occasion... the graduation of her only son. Mason was the one man in her life who had never been a disappointment to her.

"You look so handsome," the mother of said. She was so proud of her only child. He was graduating with honours and a full football scholarship, and he had made the almost two decades of her personal sacrifices so worth it.

Mason turned to admire his mom and even though he knew how pretty she was he couldn't hide a gasp. Today his mom looked utterly ravishing. His eyes swept down her slender body. Her legs were adorned by sheer tan nylons; her high heeled sandals displayed toes that were newly painted red. He loved it when she wore nylon stockings, and he felt his dick hardening in his tux. He was glad he was sitting on the edge of his bed; perhaps she wouldn't notice how much she was exciting him.

Mason, who was usually sly with the ladies and often even with his beloved mother, stammered, looking at her gorgeous face but still distracted by her beauty and her nylon-clad legs and feet, "Y-y-you look pretty amazing yourself."

"I can't remember the last time I dressed up," she said, feeling sexy for the first time in a long time.

"Joan's wedding," Mason suggested.

"That was three years ago," Lily said, surprised it had really been three years since she'd gotten all dolled up... God, how time flies.

"That's a super nice dress," Mason complimented, feeling like he sounded like a dork.

"Only the best for my son," she smiled, as she handed him an envelope.

"What is this?" Mason asked.

"An envelope," Lily teased.

"Wow, just what I've always wanted," Mason joked back, as always, enjoying the quick witted banter he and his mother often shared.

"Open it," she coaxed, anticipating an excited look on his face.

"You didn't have to get me anything," Mason said, knowing that money was always tight.

"Of course I did," the beaming mother said. "You're graduating high school."

"Anyone can graduate from high school," Mason pointed out, annoyed at the 'no one fails' system his school seemed to follow now.

"Maybe, but not everyone graduates with honours and a full paid scholarship to college," Lily said, not quite scolding, "so stop acting like this isn't a big deal... it is."

"Okay, okay," Mason conceded, loving seeing his mother so happy.

Mason opened the envelope and pulled out two tickets. He stared at them, confused. He asked, even though it was obvious, "You got me two tickets to a cruise to the Caribbean?"

"Actually, I got us two cruise ship tickets to the Caribbean," Lily corrected, over-dramatically extracting taking one ticket from his hand.

"How can we afford this?" Mason asked. Although they weren't truly poor, they didn't have extra money for very many perks. One of the reasons he was hoping to use his full college ride as a springboard to eventually get noticed by scouts and make the NFL.

Mom and Mason had always been just an 'us'. Ever since the sperm donor had left while she was still pregnant with Mason, it had only been the two of them. Even her parents had disowned her when it became apparent she was going to be a single mother; even though her father was a church minister, he had never seemed to comprehend that the Bible's underlying theme was one of forgiveness. So at sixteen, Lily was not only a single mother, but living on welfare.

Yet, the determined Lily had worked her ass off, eventually getting her GED, then even graduating college before Mason had completed elementary school, and eventually gotten a job as a social worker helping young kids who needed the same help she had been so desperate for all those years ago. Of course, it didn't pay really well, social workers being criminally underpaid, but it paid most of the bills.

Lily had also worked as a waitress at a restaurant, where she was hit on constantly, to make enough money to get these tickets. She smiled with pride at hers son, "I've been saving since you started high school."

"Really?" Mason asked, still amazed.

Lily drew her son in for a hug. "I wanted to do something special, just the two of us, before you went away to college and I was a thirty-five-year-old lonely spinster."

"You could date, you know," Mason pointed out, loving feeling his mother's massive breasts squeezing against him... these were the tits he had drooled over, fantasized over, for enough jerk off sessions to fill a dozen 7-11 Slurpee cups.

"Maybe I will, once you're out of here and I have the whole house to myself," she smiled, even though she was actually dreading him leaving this August. She really had no idea what she was going to do with herself once she had the house to herself... it had always been the two of them. Ever since Mason had been born, Lily had never dated. She had made a solemn vow to herself always to be there for her son, and had thus sworn off men. She couldn't even imagine what life would be like without her son as part of her daily life. She had always made good on her vow, even attending every high school football game he had been in -- including during his freshman year when he'd sat on the bench through most games. (She blushed to recall that Mason had once confided in her that all his teammates called her a MILF.)

Lily straightened his bow tie affectionately before saying, "Now let's go and get you graduated."

As his Mom turned towards his bedroom door, Mason glanced down for one more look at his mom's stocking-clad feet. Many eighteen-year-old sons would hate to go on a two week cruise ship with their mother, but in addition to her being an amazing, dedicated, loving mother, she was also the focal point of almost all of his sexual fantasies. She was the reason for his nylon fetish... she wore them to work every day and remained in them even when at home. Mason had learned recently while searching in her dresser for a pair of pantyhose to masturbate into, that he wasn't the only one: she also masturbated a lot. He'd found a half-dozen sex toys. A few days later while he was snooping again, this time in her closet, he'd found even more of them! He knew she had sacrificed everything for him and at least she had found a way to get herself off.

Mason would sometimes jerk off visualizing the head cheerleader Shannon, his hot English teacher Mrs. Walker, or his shy, but cute Physics partner, Betty, but his default and best stroke fantasy was his Mom.

So the idea of spending two weeks in the Caribbean with his MILF Mom where she would likely wear bikinis most of the time was a no brainer... even if it meant likely two weeks without stockings.

Two weeks later, they were on the cruise.

They were mistaken as a couple on more than a few occasions. Mason looked older than his eighteen years, a perk of being a well-built football player, while Lily looked much younger than her thirty-five years... a mixture of genetics and the ridiculously grueling workout routine she had been putting herself through for the past six months... ever since she knew she would have to be in a bikini. So although she was undoubtedly older than her son, no one, not even one person, suspected that they were mother and son.

Lily enjoyed the compliments and even began to play into the charade that they were a couple as she took her son's hand while they did a tour of an original colonial city on the second day.

Mason's cock instantly hardened when she first took his hand, and he loved it as they held hands for the majority of the next few hours, and again on and off throughout the next couple of days. Each night Mason shot his load in the bathroom, rapturous fantasies of his Mom beginning to consume him completely.

On day five, they got a day to do whatever they wished on one of the main islands. After four days of being either on the ship or in a tourist trap, even with the shared pleasure if their affectionate hand holding, the mom and son were already sick of shopping (and had already spent most of their trinket budget), nor did they want to spend the day crowded onto a beach with hundreds of tourists.

So when a native of the area in a water taxi tried selling them a ride to a secluded beach a half hour boat ride from the main one, they took him up on his offer.

Expecting to be at the beach today, Lily had worn her new white bikini, not noticing that she suddenly had her son's cock ready to rip through his trunks. And although the day was a scorcher, she got cold quickly on the boat in such a tiny bikini and a shawl that did little more than conceal her body, until she was at the beach.

Mason struggled constantly and usually unsuccessfully not to stare at his Mom's tits in the bikini... her voluptuous tits, barely contained by the thin fabric.

Lily, shivering as the wind hit her, leaned back into her son.

Mason, feeling his mother shiver, wrapped his arms around her, wanting to keep her warm but, also savouring their closeness. His cock remained hard the entire ride; his arms were resting just below her tits... he could feel their warmth on his arms.

Almost thirty minutes later, which seemed like only five for Mason, who was thrilled with the illusion that he and his mother were a couple, the water taxi driver pointed to an island, said something, and then asked them a question, which neither of them completely heard, but Lily nodded yes.

The water taxi driver grew a big smile as he nodded and parked on the island's white beach.

When the driver was dropping them off his mother moved away from him, and Mason felt a brief moment of disappointment. He had spent the last half hour cuddling his mother, gazing down over her shoulder into her voluptuous valley. Her shawl constantly opened up from the wind, and her eyes were looking ahead, giving him an uninterrupted, unobstructed view. He was very careful not to allow his constant erection to touch her.

The driver said, "I be back, four hours."

They nodded; that seemed like a reasonable amount of time to tour this seemingly secluded island.

He added, "Follow path. Twenty minutes. You be at small private cove with beautiful white sand beach."

Mason again nodded and thanked him.

He nodded back, grinning from ear to ear, as if involved in some inside joke that only he understood, "You have fun, but don't be late."

After all the hoopla and tourism of the past few days, the overcrowded tourist traps and aggressive sales people, this would be a refreshing and much needed quiet time for the two.

Once the water taxi was gone, they began walking down the narrow path to the cove their driver had mentioned. Lily, who had definitely chosen the wrong shoes - three inch pumps - for a twenty minute hike on rough terrain, took her son's hand and joked, "Don't let me fall."

Mason tried to sound as if he were joking but was deadly earnest as he promised, "I'll protect you with my life."

The longer they walked, the more Mason felt less like a son and more like a boyfriend... a boyfriend who tragically hadn't yet consummated the relationship.

When they arrived at the cove, they found three very attractive couples already there, the women all wearing equally skimpy, revealing bikinis that made his already hard cock tense up further. All three women were model hot and in their twenties, while all the men were chiseled gods who seemed to be right out of a GQ magazine.

And although Mason felt he was a pretty good looking guy and in great shape (he worked out daily to stay in shape and to add muscle to his body for the upcoming fall football season), he didn't compare with these guys.

Lily stared at the three men and their Adonis bodies as they ran around playing with a football thinking, 'Holy shit, they're perfect'!

Although they had been hoping to be alone, that wasn't possible if they wanted to remain at this beautiful cove. The beach was only about thirty feet long, with rocky outcroppings on both ends.

Lily suggested, as she removed off her shawl, "Let's drop our towels here and go for a swim."

"Sure," Mason agreed, noticing his mom's nipples suddenly poking through the tight white of the skimpy bikini top that was barely concealing her voluptuous breasts.

Lily placed her prescription glasses on her towel, leaving her virtually blind as a bat, and Mason took her hand, leading her to the beautiful, crystal blue warm water.

A couple of the girls waved at them as they passed and Mason waved back even as his cock flexed again in his trunks.

In the ocean, mom and son frolicked, dove under water looking for sea shells and even tackled each other... acting like they were twelve.

About fifteen or twenty minutes in, Mason glanced back to the beach and had to do a double and then a triple take. All three women were on their knees, apparently giving their guys blow jobs.

Mason stared in awe until his mom asked, "What are you looking at?"

Mason, knowing his mother couldn't see that far without her glasses, replied casually, "Oh, nothing."

For the first time in a while Mason noticed his mom up close from the waist up as she was adjusting her bikini top after all the horse play, and his raging hard on came raging back. One breast almost seemed be falling out completely as she joked, "I probably shouldn't have bought such a skimpy bikini."

"On you it looks amazing," Mason appraised, speaking the truth, before adding, "it makes you look like you're twenty-one."

'Fuck, I wish she wasn't my mother,' Mason thought to himself, longing to bury his face between those voluptuous tits.

Sure, Mason had fucked a few girls, including a MILF who was one of his fellow players' moms, but nobody turned him on like his beautiful mother did.

"Oh, to be young again," his Mom sighed. The reality was this trip had rejuvenated her and made her feel young again and she didn't want it to end ever... especially when others thought she was young enough to her son's date.

"Well, now that I'm eighteen and you won't be shackled by a kid anymore, you can finally begin living those wild years you were supposed to have had before little ol' me came along," Mason joked.

"First off, there is nothing about you that is little," she argued, referring to her son's massively built body and then adding, "and second, I was never shackled by you."

"I was just making the point," Mason declared seriously, "that you are an utterly beautiful woman."

"Oh, stop," Lily demurred, but enjoying the compliments.

"You remember me telling you that every one of my friends call you a MILF," Mason pointed out, something that had driven him nuts since he was in grade eight.

"They still do?" Lily asked, she'd mostly forgotten that.

"Actually even a couple of the cheerleaders want to sleep with you," Mason added, again telling the truth, since right after a game earlier this year Celica had bluntly told him that she wanted to fuck his mom.

"Now you're just being silly," Lily said, feeling herself blush, even though she indeed did like the idea of others finding her attractive.

"I'm serious," Mason said, and then deciding to just throw it out there and see where it went, "If you weren't my mother, I'd be all over you." God, she was model hot... made even hotter by the reality that she didn't believe it. Her parents' rejection all those years ago had crushed her self-esteem and she had never truly recovered.

"Mason!" Lily gasped, scandalized by her son's words.

"I like older women," Mason insisted, attempting almost desperately to give his mother any possible excuse to see him as more than just a son. He glanced back to the beach and saw all three girls still sucking cock, and if he wasn't mistaken, they had swapped men.

"You do, do you?" Lily said, suddenly flirting teasingly with her son. "And this is from experience?"

"It is," Mason nodded, his attention jumping back and forth between the blow jobs back on the beach and his mom's perfect tits and beautiful face.


Mason elaborated, "Older women know how to please a man."

"Oh God," Lily said, shocked at where the conversation had gone.

"What?" Mason asked, "I don't have a male role model to share these conversations with."

Lily sighed... that was true. "Well, I promise you can share all your conquests with me later, but for now I need to get back under this warm water."

She dove into the blue ocean as her head spun with the strange conversation and her darling son's abundance of compliments.

Mason looked back to the beach and witnessed the three women stand up, each rotate and drop back onto their knees in front of a new cock. Was it possible he and his Mom could become a part of that?

Mason turned and tackled his mom from behind, his hard cock accidentally poking directly into her ass, and Lily immediately let out a soft moan.

'Is that his cock? Why is it hard? Because of me? How big is it?' Lily thought to herself, before scolding herself for even thinking such things.

Mason got back up and wondered, hoping, if there was any chance his mother could be as horny as he was.

Lily found her feet and playfully shoved her son backwards into the ocean.

A couple minutes later, as they were both still horsing around, Lily cried out of the blue, "Oh shit, shit!"

Mason was instantly concerned and asked. "What, Mom?"

"Cramp," she groaned, obviously in pain, as she began walking to the shore.

As he turned to follow, Mason noticed the three couples were no longer just in oral sex mode, but now were enjoying a full blown orgy. One girl was licking pussy, another was getting fucked while sucking another man's cock, while the third was sucking the third man's cock, while having her pussy licked by the first girl.

It was the hottest, most surreal thing Mason had ever seen. It was a live action porn movie... and although the plot seemed unbelievable, it was really happening and not on film... and the plot was about to get even wilder.

After a few faltering steps, Lily asked, "Can you help me back to the beach? I can't see a thing and this cramp is killing me."

Mason, of course, helped her. As she put her arm over his shoulder, he led her back to the beach... directly towards a six person orgy.

As they got out of the water, Mason received a full-body view of his mother in the wet bikini. Although he'd already admired almost all of her massive tits, what he now could see was that the suit looked as if it were painted on and he stared at her erect nipples for a moment before noticing that she seemed to have waxed her vagina and her pussy lips were protruding. She was a real 'MMILF' -- 'My Mother that I'd Love to Fuck!'

"Oh yes," one of the girls moaned, once they were within ear shot.

Although the reasons for the sounds seemed obvious to him, his mom still appeared to be oblivious, as they walked right past the orgy, only clearing it by maybe ten feet. The beautiful blonde that was having her cunt licked, while now stroking on a big dick, asked, "Do you two want to join? The more the merrier."

Lily answered absently, "In a minute; I need to work out this cramp first."

Category: Incest/Taboo Stories