Island Hospitality
Tropical flying was one of Rainbow Dash's secret pleasures, and one she would rarely admit to enjoying. The reason being a rather simple one; most ponies that knew her thought of her as being the fastest flyer in Equestria, wholly dedicated to getting from Point A to Point B in as fast and awesome a way as possible. It was an image Dash had carefully cultivated, and although her closest friends knew her a little deeper than that, but even they would be surprised by how leisurely Dash was currently soaring on a tropic thermal, letting the breeze carry her to her destination without a care in the world.
The trip to Singapone had been a quick flight; Rainbow had decided to fly there herself, knowing she could arrive faster than by any ship or balloon. She had been called to a weather conference in the island city, and had not particularly wanted to take the mandatory business trip, and so had left with the intention of going and returning as quickly as possible. But once she had arrived and concluded the two-day conference, she started to notice the allure the exotic city had.
She sent a letter home letting her friends know she would be a while longer, Dash had spent a few days in Singapone. It had come as a welcome and unexpected vacation, and now she was taking her time getting back to Ponyville.
The sky was cloudless, Celestia's sun beating down on the emerald sea. This normally would not have concerned Rainbow Dash, but her saddlebags were starting to get a little heavy, and she couldn't very well nap on the ocean surf. Her dilemma was solved by the sight of a small island with a hut on it, a flagpole with a blue and white banner fluttering in the gentle breeze.
Rainbow dash descended to the hut, taking a look around. Rest areas such as this were maintained by the Equestrian Weather Service for ponies just like her, a place to recuperate after long flight and hard work. Visitors signed in and out, and were allowed access to the supplies maintained on the honor system.
Dash signed her name on the clipboard on the front porch, and noticed that while this station was regularly maintained, it wasn't visited very often. She was alone, and would likely be for the duration of her short stay.
Dropping her saddlebags inside the hut, Dash wandered onto the beach, looking over the blue lagoon. The entire island seemed so picturesque, it wasn't hard to imagine the whole thing as a dream. The thought of dreaming made Rainbow's eyes heavy, and the soft heat of the day did little to dispel her drowsiness.
The sand beneath her hooves was so wonderfully inviting. Dash quickly went into the hut, and returned with a soft blanket. Laying it out on the shore, she curled up and basked in the warmth of the day, quickly dozing off.
A splash came from the lagoon, but Rainbow wasn't paying any attention. If she was, she would've noticed a long, aquamarine tentacle emerging from the water. It was slim, smooth, and seemed to be covered in a thin layer of slime. It was tipped by a wide, flat head covered in suckers.
Slowly and methodically, it approached the dozing pegasus, eventually looming over her. She did not react in any way, dreaming as she was. It reached down and gently stroked the leading edge of one of her wings. She purred in response, slowly extending the appendage. The tentacle continued to gently caress it, eliciting more gentle purring from Rainbow Dash, who wasn't conscious enough to notice what was going on.
The arm moved closer to her shoulder, to the more sensitive base of her wings. She groaned as it began to more firmly massage the erogenous tissue. The suckers began to tug on the flesh, causing more high-pitched moans from the pegasus and leaving behind small, round hickeys. Subconsciously, Rainbow's front hoof snaked in between her legs and began rubbing herself. Her purring and moaning grew in intensity as the tentacle seemed to know exactly how to touch her.
Suddenly, she shot awake. The tentacle darted back into the lagoon, making a loud splash. Dash looked around, trying to get a sense of what had happened. From her hoof and the feeling between her legs, it was obvious she'd been touching herself, but she didn't remember doing that. The feathers on one of her wings were mussed, too.
"Hey you!" she shouted out. "Whoever you are! I know you're here somewhere, and that you were giving me a preenjob while I slept!" Her voice was angry. No one answered. After a few minutes, she added, in a more playful tone, "I didn't say I didn't like it!"
There was a splash, and another tentacle rose out of the water, several feet into the air. Rainbow Dash immediately leaped into flight, hovering several feet above the ground. The tentacle jerked backwards as though startled, then the two of them simply remained there as if regarding each other.
"What are you?" Rainbow Dash asked in a confrontational tone. "Some sort of monster? Do you eat ponies?"
The tentacle waved from side to side, as though it were a head shaking no. Dash landed, somewhat more at ease. At least the creature understood her. "What do you want, then?" It approached her, slowly and gently. Rainbow kept her eyes on it, but let it come without alarming it. It hovered over her flanks.
Rainbow was confused for a moment, but then blushed as realization struck her. "Did... did you give me a preenjob?" The tentacle bobbed up and down, nodding. "Do you... want my pussy?" An emphatic yes.
Dash considered a moment, examining the tentacle further. It was about an inch thick, but with a round, smooth bullet-shaped head that was almost two inches in thickness. It would be easily the biggest thing she had ever taken, but Rainbow Dash was nothing if not adventurous. Giving the appendage a lustful gaze, she wordlessly presented her plot to it, hoisting it up in the air and lifting her tail.
Rainbow was already noticeably horny from the preenjob, and her snatch was good and wet, making it easy for the tentacle to enter. It pushed its tip against her wet folds, then slowly and deliberatedly penetrated her. "Ahhhhh..." Dash moaned as the tentacle filled her pussy, stretching her inner walls to the point where its just barely uncomfortable. She'd gotten laid before, by both stallions and mares, but this was a decidedly new experience for her. She looked back, and the sight of the massive appendage slowly worming its way into her body sent shivers down her spine.
The tentacle seemed to know exactly when to stop, and came to a rest inside her, leaving her comfortably filled. It was cool, quite different from the warmth she was used to feeling from when stallions had screwed her. The contrast of the cool tentacle to her feverish nethers was not unpleasant, and in fact managed to amplify her pleasure. The appendage slowly began to withdraw, producing a wet squelching sound as the wide tip parted her folds. Dash whimpered as she was left feeling particularly empty. That feeling didn't last as the tentacle slid back into her, and began to fuck her in earnest.
"Ahhh...Ohhh...Unfff..." Rainbow continued to moan in pleasure as the tentacle pounded her. It did not take long before the discomfort disappeared. The slime that coated the tentacle's surface served as and excellent lubricant, and it slid in and out with ease. The tentacle was not exactly fast, but it was steady, and was fucking her deeper than she had ever experienced before.
There was a splash, and she looked behind her to see several more tentacles emerge from the water. She felt weak of knees as her imagination went wild with what these new appendages could do to her. Two were phallic like the one currently pounding her, but not as big. The others were relatively thin, and tipped with suckers.
The biggest one wrapped gently around her midsection and hoisted her into the air, directly over the water. She looked down and saw a dark, formless shape beneath the surface, likely the source of the tentacles. She wasn't scared; surprisingly she found herself willing to trust this creature in spite of its monstrous appearance.
A pair of suckered tentacles wrapped around her wings, and began to give her a double-preenjob, massaging and sucking on the tender flesh. A third drifted down to her belly, and begun to tweak and suck on her teats. She spasmed in ecstasy as she felt the creature touch her in all the right ways. "This is... so awesome..." she whined in pleasure.
One of the big tentacles hovered in front of her face, seeming to regard her. Her eyes were unfocused, rolled partially upwards as her tongue lolled loosely out of her mouth, a line of drool leaking out with each thrust into her. She briefly focused enough to open wide, accepting the tentacle into her mouth. It quickly began to thrust in time with the one in her marehood.
"Mmmhh, slrrrp... mmmhh, slrrrp... mmmhh, slrrrp..." she alternated between moaning and sucking on the tentacle in her mouth as they both fucked her in unison. She quickly lost herself in bliss, but then remembered that there was still a third tentacle that the creature had yet to deploy.
Nervousness overcame her as she watched the tentacle approach her backside, above the one already in her. She'd never had it in the plothole before, and the idea made her stomach start to flutter and a cold sweat form on her. The tentacle wasn't as big as the one in her snatch, to be sure, but it still looked very intimidating. The creature seemed to notice her apprehension, and eased up on her, gently caressing her as though to ensure her it would be alright.
As the tentacle in her mouth came out, she said, "It's... it's alright. Go ahead..." and began sucking again. The tentacle at her rear pushed up against her entrance, gently prodding her sphincter, relaxing and dilating it. Her moans grew in intensity as it wormed its way inside, and up into her rectum. It felt so wierd, not exactly painful, but not the same sort of pleasure she was getting from the one inside her marehood.
That seemed like it could change as the three tentacles thrusted in unison. Rainbow Dash had never been the center of so much attention, and her body was loving every second of it. "Mmmhh, slrrrp... mmmhh, slrrrp... mmmhh, slrrrp..."
The pressure inside of her was building, and Dash was focused solely on achieving her climax. However, it was eluding her, and the tentacles were doing everything to her she could conceive. Inspiration struck her, and she tried to spit out the tentacle in her throat.
"Cum inside me," she said between gasps. "I... I want you to cum inside me," and she swallowed the tentacle again.
The tentacles renewed their assaults with increased vigor, no longer holding back anything. Her eyes bulged as her entrances were pounded mercilessly. The appendages bulged suddenly, pulsating down their lengths. A large spurt of something salty squirted down her throat, and she felt both tentacles in her lower entrances ejaculating. She gave a muffled scream between swallowing spunk as her entire body convulsed, her eyes feeling like they would pop out of her head with the force of the orgasm rolling over her.
She wasn't sure how long it lasted, as the tentacles seemed to want to stretch it out forever. Eventually, her entire body went limp, and the tentacles pulled out of her, dripping a green thick fluid. They gently cradled her body, seeming to bask in the afterglow with her. She didn't say anything, just stroked one with the tip of her wing.
They lowered her back to the blanket she laid out to take her nap on. "That was... yeah. That was good," Dash muttered sleepily as they withdrew. She then sunk into a deep sleep as the still mysterious creature watched over her.