A Fairly Fairy Family Trip

A Fairly Fairy Family Trip

Summary: Family of four takes an 'adult' vacation at a tropical theme resort, and enjoys many experiences none of them (except for Mom) would have ever thought possible.

Note 1: This is a NUDE DAY 2021 Contest Story so please vote.

Note 2: The basic idea for this story was dreamed up by my long-time editor Tex Beethoven, who has been playing around with illustrations for a little over a year and a half. And since I'm sometimes told many of my stories are similar to each other, I think you'll find that although this one includes a number of unmistakable silkstockingslover themes, it's nevertheless quite a departure from my normal fare. (The opening illustration might give you a clue.)

One late afternoon in early July, Layla Emerson, the pretty mother of teenage twins, called her family together to make an announcement.

"Kids, since you're both eighteen now, and most of the COVID restrictions have mellowed," Layla began to her twins, "I think we're ready to go on an adult family vacation together."

"An adult vacation?" Sabrina, a pretty redhead like her mother asked.

"Yes, I've organized a weeklong trip to a place where you two can legally drink with your father and me, and you can take part in some special fun activities like the adults you now are," Layla said, not mentioning just how adult she'd be allowing... even encouraging them to behave.

"Cool," Hal said cheerfully, since although a trip with the parents might sound boring to most boys his age, to him the chance to hang out with his Dad and twin sister, but especially with his hot Mom (who like many boys he'd love to fuck) was way cool! He asked, "Where are we going?"

"To a beachside resort in Belize," Layla replied.

Walker, the lucky and grateful husband to this beautiful woman asked, this being news to him as well, "Really?"

"Yes," Layla said. "We leave in a week."

"Wait a minute! You can't just spring a weeklong trip on us out of the blue like this; especially because at this late date, I won't even have enough time to organize the time off work!" Walker objected. His wife could be very spontaneous. For instance, she'd sucked his cock in the McDonald's drive-thru just yesterday, and back in the day she'd strolled on his arm down a crowded street in a Mexican beach town with a load of his cum all over her face while beaming at everyone with pride...

...and she was the one who'd initiated all five of their threesomes in the past three years (always with another girl instead of a guy, thankfully). She also loved having sex while the kids were home and might catch them, often leaving the door partly open, to plant some seeds in their heads for those fun activities she'd mentioned for not far down the road. Neither of the parents realized that just a few days ago, the two rascals had snuck up to the top of the stairs to watch. (Author's note: since we shot this scene in a two-story open-plan house, this is the closest we could come to showing them peeking through a partly open doorway. They were, however, crouching at the top of a stairway, each of them wearing (not shown) flannel pajamas.)...

...but this 'adult vacation' idea seemed a little over-the-top wild even for her!

"No worries, I've already arranged those days off for you," she reassured him. Layla was without a doubt the decision maker of the family. She was never heavy-handed about it, and she certainly didn't micromanage... in fact she generally encouraged her husband and kids to do pretty much whatever they pleased, within reason of course... but when she did want something to happen, she got it... and she wasn't afraid to put her foot down if needed... although she almost never needed to. There was a clear hierarchy in their family's structure, and her husband and kids all knew when she was drawing a line they mustn't cross.

"Well that's good news! So may I take it everything is already booked, and all the details already seen to?" Walker asked more cheerfully, loving both his wife's organizational skills and her free spirit. Such as last week, when the moment he'd arrived home from work, Layla and a young-looking college girl named Vanessa pounced on him, and almost immediately he and Vanessa (who was already stripped down and wearing a strap-on) began double teaming his wife to multiple orgasms.

"Of course it is," Layla smiled, "absolutely everything has been taken care of," before deciding this conversation was at an end for now, since the real surprises wouldn't start being revealed until they'd arrived at the resort. "Now everyone go and get dressed for tonight's party."

"Yes Mom," both her children said in unison. The family had a weekly tradition of cosplay parties... sometimes with invited guests, but more times than not it was just the four of them. They literally had over a hundred different costumes they'd already worn on various occasions.

Here's one from a couple weeks ago.

Roleplaying was one Layla's biggest turn-ons, and Walker had fucked her in many of her costumes, like right after their beachcomber party...

...and following their 'Holier Than Thou' party... where she portrayed a bride who's fucked by the opportunistic minister...

...and finally for now, in celebration of the upcoming trip.

Layla also loved to showcase her sexy birthmark... the outline of a butterfly right above her right breast, and her daughter had one too; they'd each had theirs since birth.

Sabrina had asked her Mom many times why they both had the exact same birthmark in the exact same place.... But her mother always just shrugged and told her it was just one of life's mysteries. It had used to bother her, but now she found it sexy, and anyone who noticed it when she wore a bikini or something always thought it was a tattoo, so they too thought it was sexy, which made Sabrina feel badass.

Of course only Layla knew the complete truth, which would be shared with the rest of her family at the resort.

Actually, lots of secrets would be coming out at the resort... and not all of them at once.

.....

The family took a redeye flight so they could arrive at daybreak on July 14^th... and only Layla among them realized the significance of that date... Nude Day.

They arrived in Belize City, the capital of Belize, which is a small country on the Yucatán Peninsula, bordering Mexico to the north-northwest, Guatemala to the south-southwest, and its eastern border was its coastline, stretching along the Caribbean Sea. At Layla's insistence they'd all dressed for the trip in sexy, revealing costumes. Or at least Layla and Sabrina did; Walker and Hal had each tried to come up with something suitable, but because men's fashions tend to be so humdrum, they couldn't find much. (Layla didn't give them a hard time about it; she knew within a few hours of their arrival in Belize, all four of them would have no difficulty in looking extremely sexy.)

A van picked them up from the airport, and drove them an hour away to a resort called País de las Hadas (Spanish for Fairyland), which in addition to being located on the coast and having its own very long private beach, was a theme resort that would be catering to some of their family idiosyncrasies in ways that so far nobody but Layla had a clue about. As usual Layla stole the show with her costume, wearing a skimpy bright blue outfit made almost entirely of feathers, and with thong-cut panties that weren't fabric, but appeared to have been forged from solid gold (but probably weren't). But what really set her apart was a huge pair of fake wings strapped to her back, that for the flight she'd had to store in her luggage.

When they stepped into the resort's lobby, they were surprised to find everyone naked -- and even Layla was surprised. The lady on duty behind the front desk was also nude, except for what was kind of a garment, since she was inked with a huge tattoo covering her entire body, front and back except for her lovely Asian face. When asked about everyone's nudity, she explained that today, July 14, was Nude Day, which was being wholeheartedly observed by pretty much everyone at the resort, both the staff and the guests. Although technically the resort's regulation was Clothing Optional, she told them that except for guests who were just arriving, she hadn't noticed anyone wearing much of anything so far today. The Emerson family could remain clothed if they wished, of course, but they'd definitely stand out in the crowd. In fact País de las Hadas was Clothing Optional at all times, with the staff always fully nude, except for the aprons worn by the staff in the kitchens, and minimal clothing required for guests and staff alike in the dining room, but today they were offering all their guests especial encouragement to go naked because of the holiday. She quite specifically said to Layla she sincerely hoped the Emersons would give serious consideration to joining in on the festivities fully, since she'd hate for them to feel left out. Layla immediately took a liking to this charming woman, who'd introduced herself as Yasmin. (Pinning a nametag onto herself would have been totally impractical, for obvious reasons.) She gave Layla the impression that her mission in life was to mother everyone around her, and to do whatever was necessary to keep them healthy and happy. (Which in this case apparently included stripping down for their viewing pleasure. Layla certainly took pleasure in the view, since Yasmin was indeed beautiful.)

"Oh, I'd forgotten that detail about this resort," said Layla aloud, but Sabrina quietly wondered if she really had. Sabrina also noticed this naked staffer was standing near a large picture window, so she and just about everyone else in the lobby were readily visible from a public street. Although the thoroughfare was deserted at present, anybody could easily happen by, possibly even including policemen, although around here presumably John Law (or likely Juan Ley) wouldn't mind any amount of public nudity. Sabrina decided that just like Dorothy Gale, she wasn't in Kansas anymore.

Sabrina was a little, or perhaps a lot, baffled by the costume her Mom had chosen to wear, and the surprising one she'd insisted that she wear... with no bra... which was an almost see-through skimpy halter top on the one hand, but on the other hand, it included sheer thigh high stockings. Ordinarily she loved wearing high stockings, but this country was hot as fuck. She asked, "Why are we wearing such skimpy clothing?'

"Trust me," the mother said, admiring the sight of her daughter's ripe young body in the sexy attire. "It will all make sense very soon."

"What does that even mean?"

"It means I'll explain later. But have I ever steered you wrong, honey?" the mother asked, knowing what was best for her daughter. (And to be clear, not the best given Layla's abilities or lack of them, but the best conceivably possible on any scale imaginable.)

"No, I guess not," Sabrina admitted, her mother acting even more flamboyantly than usual today.

"Like I said, Sabrina," Layla repeated. "It will all make sense very soon."

So there she was, in the lobby of a resort where everyone was starkers except for her family, and things were not making more sense, they were making less of it... although she did understand her own skimpy attire a bit better now... around here she was overdressed compared to everyone else... but why on earth would her mother bring them to a place where everyone was naked except them?! What kind of resort was this?!

Hal too was in compete shock. He'd watched some porn sometimes of course, and seen a couple girls naked, including his mother just a few nights ago while he and his sister spied on her fucking and their talking nasty to each other, which had really turned him on... but the surroundings here contained an entirely different... previously unimaginable... level of nudity!

Walker was also stunned, for even after living his wild married life with his wild wife... this was a whole new level of kink. Instead of his supporting all Layla's sexy whims while they shocked everyone around them, today he was the one being shocked!

An extremely pretty (and of course nude... hurrah!) Asian woman strolling by caught Walker's and Hal's attention, and she gave them a particularly friendly smile, but she didn't pause.

Walker, noticing his son's cartoon-like bulged-out eyes, laughed and advised him jokingly, "Why don't you put your tongue back in your mouth, sport?"

"Where on earth are we?" Hal asked.

"Apparently it's Heaven for you," Walker laughed, patting his son on the back man to man, as they both watched the hot girl walking away for the entire time... nice butt!... until she disappeared from sight.

"What kind of resort is this?" Hal asked.

"I have no idea what your mother has gotten us into," Walker said, now admiring someone else's amazing naked ass.

Once Layla had checked them in, the family headed up to their room, encountering yet more naked people pretty much every step of the way, with nary a scrap of clothing to be seen, except for occasional accessories. And some of the guests were having sex right in the hallway!

It seemed not only was clothing optional at this resort, but so was public sex! At one point they were confronted by a complete roadblock, or actually a hallway-block since that's where they were, with two couples fucking in such close proximity to each other, there was hardly any room for pedestrian traffic!

"Oh my," Sabrina gasped upon seeing the two girls licking each other, something she'd fantasized about doing herself on more than a few occasions. She wasn't a lesbian, nor was she straight. She was intrigued both by cock and pussy... or at least hypothetically she was, since she hadn't had the opportunity to sample either of them yet.

"Holy shit," Hal gasped, his eyes going wide as he saw a guy fucking a girl right in front of him while they were standing, distracting him into almost tripping over two lesbians (or perhaps bisexuals) who were fully engaged in a sixty-nine on the floor.

Walker didn't say anything, he just enjoyed the view, but he wondered what else his wife had in store for them... no way she could have brought them to such a place by accident... she was far too meticulous [A1]in planning events to possibly not know what she was getting them into.

However even Layla was surprised, saying, "I hope all this uninhibited behaviour around us isn't too shocking for my innocent children."

"No worries Mom, it's way cool," Hal enthused, his only worry being unsure where to direct his eyes: at the two hot girls eating each other out, or the other hot girl getting fucked.

"Hey, you sexy thing," the girl being fucked (rather than eaten) grinned at Hal.

"H-h-hi," he stammered as he stumble-footedly followed his family past her.

"He'll be out and about later," Layla informed them graciously as they passed the two couples enjoying their exhibitionistic sex.

"Mom!" Sabrina gasped. "You're pimping out my brother?!"

"What? No, certainly not. But there's no harm in mentioning he'll be around later, because he will be," Layla shrugged as they all kept walking.

They reached their room in only a few more steps, Hal stumbling into his sister and his open hand accidentally landing on her ass, since he was still gazing back at that outgoing girl getting fucked.

"What are you doing?" Sabrina squealed, turning around to confront him.

"Sorry," Hal said, although he wasn't sorry at all, since he'd enjoyed more than a few stroke fantasies about his hot sister. In them, he was often the centerpiece of a threesome with his Mom and her. Yes, he realized he had a fucked up mind, but what could he say... he was eighteen... and a virgin... so of course he was always horny.

Once they arrived in their room, Hal, with his dick doing all his thinking, and wanting to get back out there to see even more naked women having sex, this vacation already way too excellent to be true, suggested casually (yeah, right), "Why don't we get changed so we can hit the pool?"

"I know why you're in a hurry," his mother teased.

"To go for a swim," Hal defended, turning his body away from her and his sister, trying to conceal the embarrassing tent in his pants.

"Gotcha," Layla smiled, looking directly at the tent. They all went to change into their bathing suits, and when they returned, Sabrina asked, "So is this place for all intents and purposes really a naked resort?"

"Yeah, I guess it is," Layla admitted, and Walker could tell by his wife's tone she wasn't surprised... she'd known it all along.

"And we're staying anyway?" Sabrina asked.

Layla said, as she stripped off her bikini top, "What choice do we really have? It's already paid for. Besides, if we're 'stuck' at a nude resort, which I don't consider terribly unacceptable, my thought is to embrace it fully."

"It is?" both Walker and Sabrina asked.

Hal just gasped, since he was suddenly staring at his hot Mom, totally naked except for her pink stockings and bikini bottoms.

"When in Rome..." Layla shrugged, pulling the string of her bikini bottoms and tossing them playfully at her son.

Even Walker was stunned by his wife's sudden brazenness. Sure, at heart she was wild as fuck. Sure, they'd even indulged in the odd incest roleplaying together; but this, as has been said but bears repeating, was an entirely new level even for her!