Dreamboat

For as long as he could read, Pipsqueak always secretly wanted to be a Pirate. He'd read about them since he was a little colt, and even up to his 20th birthday, he'd harbored a desire to sail the high seas as a pirate Captain. Pipsqueak the Pirate!

But sometimes, the world has a sick sense of humor.

The sad reality is that under Celestia's sole rule for the past thousand-odd years, things were peaceful enough, and Equestria's Naval might had never really been questioned, but something was rotten and some ponies just instinctually knew it. In the last Century or so, things had happened that shouldn't have. Things like the Revival (and summary re-defeat) of Discord, the Destruction of the Tree of Harmony, The Cult of Equality, Tirek, Scorpan, Grogar... things all just seemed to be going to hell in a handbasket on Equestria's main island. Hell, even the day he and his family had left Trottingham for Port Canterlot, there had been a Bugbear attack.

Things were *much* different in Port Canterlot, since it was a military town, the local law enforcers were quick to judge and impossible to reason with. Pipsqueak had gotten into a little trouble as a young stallion, only 4 months after his 20th birthday. It was an accidental incident, purely a misunderstanding of course, but the Judge was a real hardcase, and said that the punishment was either hard labor... or join the Navy. The Equestrian Royal Navy was nothing to joke about, their power over the raging seas was second really to none, but as is normal for such things, they were *BORING*. All about rules and regulations, and all the 'yes sir no sir' crap that Pip absolutely despised. Worse still, there were no *mare* sailors. It was all stallions all the time! But, rather than breaking his back for 4 years, or worse, risk getting shanked, in the slammer, he figured at least if he couldn't be a pirate, a sailor was the next best thing.

At least, he'd thought that 8 months ago before he'd been out to sea doing 'manuevers' and swabbing decks until he turned 21. Four years of this? He'd go crazy, absolutely CRAZY before his time was up. It was already bad enough he'd heard that younger, 'prettier' sailors like him often got passed around by the bigger stallions, he didn't want to end up under some big, sweaty meathead praying for a mercifully quick ending and thinking of Trottingham. Nope, that wasn't gonna be him, no siree.

To complicate matters further, he'd started having nightmares. Well, nightmares he thought for lack of a better word. For weeks now he'd had the same dream over and over, a big, black mare, standing over him, one hoof at his throat, the other... doing *things* to his junk. Sometimes good, sometimes bad, all of it embarrassingly hot. So much so that he'd started having to clop in the privy before sleeping, just to make sure he didn't mess up his bunk while he slept. Then, even that had proven not to be enough the previous night.

Last night, Pip recalled, was particularly vivid; in the dream, the big black mare wore blue armor, had sharp teeth, wings AND a horn. Her actions had taken a turn for the downright shameless as well, using her mouth AND hooves to get him as hot as he'd ever felt, until, oops, he woke up groaning quietly and popping his load all over the blankets he was under. It wasn't an easy thing to hide, but he'd managed somehow, and even though the older sailors teased him about walking into the morning mess with his dick hanging out still, he ignored it and just ate his breakfast quietly.

It would prove to be the last meal he'd ever eat on board the ship.

It was about halfway through the day when the storm had rolled in, not really too bad, just a little choppiness to the water and some rainfall... but with the storm came *revenge*.

"SHIP AHOY!" The stallion in the crow's nest shouted, panicked. "SHE'S FLYING THE MOON CREST AND BLACK SHEETS! IT'S THE PRINCESS LUNA'S REVENGE! NIGHTMARE MOON IS AFTER US!"

Pip's eyes went wide. Nightmare Moon? THE Nightmare Moon? She was only the most ludicrously powerful and infamous pirate to ever grace the deck of a ship... but she started sailing as a pirate a thousand years ago! How could she be here now?! He ran back and looked, and sure as shooting, there she was, the most feared pirate ship in all of Equestrian history.

"Oh... oh goddess... we're all gonna die!" Pip started panicking a little, his whole miserable life flashing before his very eyes it seemed. He turned to run to the fore of the ship, but was grabbed by the boson, who shook him violently.

"BELAY THAT BILGE, PIP!" He shouted harshly. "We're the Equestrian Navy, we're going to fight her to the bitter end, down to the v-" He was rudely interrupted by the sounds of cannonfire, and threw both himself and poor Pip to the deck as the aft end of the ship was hit by the opening volley from the much larger ship.

"The captain's quarters have been hit! She's aiming to disable our rudders!"

"Bring us about! Prepare to broadside portside! If this wench wants a fight we'll damn well give her one!"

"Sir, report from belowdecks! Our powder stores have been exposed to water from the aft! We CAN'T return fire!"

The captain looked down at his hooves, then resigned himself to his fate.

"Alright men, stand down. Stow the sails, and raise the white flag. Goddess willing, she'll not be in the mood for wholesale slaughter. If we can save the ship itself, maybe we can limp back to port and salvage her..."

It took a few moments for the rest of the crew to start acting on the captains orders, but as soon as the white flag went up, and the sails were stowed away, the Revenge was upon them. Her crew threw over grappling hooks and ropes to tie the two ships securely together, and then a gangplank, a rather sizeable one, to bridge the gap.

Pip and the other sailors watched in silent terror as the NIghtmare herself walked aboard, towering over the lot of them, and stepped into the center of the deck, bellowing loudly.

"WHO HERE AMONG YOU LITTLE PONIES HAS COURAGE ENOUGH TO FACE ME. I WOULD TEST THE METTLE OF HE WHO CONSIDERS HIMSELF THE BRAVEST AMONG YOU! WHO BE IT?!"

"I be it!" Pip said without hesitation, surprising everyone but himself. He jumped forward, and slowly walked up to the monstrous Mare. It was HER! She looked just like the mare he'd been dreaming of! He had to know what was going on, but at the same time, he was well aware that he was in grave danger. So, he summoned up all his courage and stood up to the fearsome pirate. "I be the stallion for the task, ma'am. All I ask is that you would spare the rest of the crew and this ship, even if my own life be forfeit for the asking."

"WELL," the great black figure's face spread into a toothy smile. "YOU MIGHT NOT BE MUCH OF A MORSEL, BUT IF YOU BE THE ONLY STALLION WITH GALL ENOUGH TO FACE US, THEN SO BE IT! TAKE HIM TO MY CHAMBERS, THEN LOOT THE SHIP FOR ALL IT'S VALUABLES AND SHOVE OFF! DISTURB US ONLY IN CASE OF EMERGENCY! UNDERSTOOD?!" And with that, the great mare stormed off, trailing after the two ponies dragging Pip to her private sanctum.

Pip marveled at the absolutely LUSH quarters the former Princess had onboard her ship. Her chambers were covered in velvet and satin blankets, fluffy pillows, and of course a massive four-post bed with privacy curtains. There were tapestries and paintings covering every inch of wall, and heavy black and blue curtains covering every window. There was a table covered in scrolls and maps, and with fruit bowls and wine bottles as well. Surprisingly, there was even a large framed portrait of Luna and Celestia on the wall opposite the bed, but Pip paid it little mind as the massive figure of Nightmare Moon made herself known behind him.

"So little one..." She stated, in a much more normal tone of voice and volume. "Let us look you over." She lifted him unceremoniously with her magic, and began looking him all over... before settling shamelessly on his crotch. "Hmmm..." She tilted her head to one side looking at his jewels, before reaching up with both hooves and unexpectedly squeezing his balls, quite painfully in fact.

"M-MY BALLS!" Pip managed to literally squeak out as the mighty mare manhandled his goodie bag. Then he found himself gazing into the big, dark eyes of the Nightmare.

"You seem to be whole and intact. Thy name is Pipsqueak, is it not, my little pony?" She asked as she let him dangle free again, her eyes narrowing at him a little.

"Y-yes ma'am!" Pip answered, suddenly very aware that he could not otherwise move no matter how hard he tried. As Nightmare Moon lowered him to the floor and towered above him again, he spoke again without thinking. "You... are the mare from my dreams!"

"Perhaps we are." She smiled wickedly, laying him on his back below her, and just like in his dreams, she sat above him, one hoof pressed into his throat... and the other now pinning his defenseless testicles to the floor. "You spoke out quickly, so you must have been eager to make your dreams reality..." She rolled her hooves a little so that he had a bit of trouble breathing, from pressure on both tender areas. "Is it everything you dreamed of, young Pip?"

"Y-yes ma'am!" Pip surprisingly gasped out, and obviously he was telling the truth, if his burgeoning erection was any indication.

"W-wha?!" Nightmare seemed genuinely surprised, her hoof raising away from his balls. She sat in rapt silence as Pip's shaft rose out of it's sheath... and rose some more... and more... and more! "Moon's light, thy name speaketh lies! You are no Pipsqueak, thou art a mighty OAK!"

"I-Indeed Lady Nightmare..." Pip admitted with a heavy blush, but a cheeky grin couldn't help itself from forming at her apparent compliment.

"You spoke of risking your life so that we might spare the rest of your crew... admirable, young Pip, admirable indeed." She moved herself down between his hind legs, another wicked smile on her face as she let her hoof leave his throat. She let one hoof trail slowly up and down the side of Pip's stallionhood, while leaning her muzzle down, down, down, smiling that sharp smile all the way until she was eye level with his junk again. "But pray tell... wouldst thou risk something more precious than even thy very life?" As she said this, she let her long, nimble tongue reach out and lap curiously under his balls, before popping them into her mouth and suckling on them. She went lightly at first, hoof still stroking his titanic rod a little faster now, but then she started sucking harder and harder, until she was practically swallowing his nuts.

"What do you mean mooOOOOOOH!" Pip's voice broke a little as the massive mare slipped his balls into her mouth, making him quiver all over, as that was all the moving he could do. He couldn't even see her face, between the angle of his head and his huge pecker in the way she was obscured totally. The pressure on his balls got to the point of unbearable, it was *so* intense that he thought he'd pass out before he got a chance to get off.

'We mean as we said,' the former princess telepathically said into his mind, 'Wouldst thou risk more than thy life? Say... those very things which make you a stallion?' As she said this, Pip could feel her sharp, pointed teeth come to rest on his aching, churning testicles and start to press into them. 'If thou be brave enough to risk life AND limb, simply say so... say you will do so in my name, swear it aloud that your mind, body and soul belong to Nightmare Moon, and we will see if thou didst really mean what you said...'

'Oh GODDESS, not my BALLS!' Pip thought to himself, unaware the Nightmare could still hear him. 'I... I don't know... I don't want to lose my balls, but... but I don't want to die either! Oh her hoof feels so nice, she's so beautiful, and I'm SO confused... her teeth! Her teeth are pressing harder! She's gobbling up my balls! Oh goddess... it's now or never!' Pip gulped hard, shut his eyes, and braced himself for the worst.

"I... I SWEAR IT! I WILL RISK LIFE AND LIMB FOR NIGHTMARE MOON, AND MY MIND, BODY AND SOUL BELONG TO HER!"

A moment passed. Then two. Then what felt to poor Pip like a Billion more... then she spat him out, a pleased smile on her face.

"Excellent... I knew you were the stallion we hoped you were." Suddenly, her voice was calmer, smoother, and even more melodious than it had been a moment before. She stood up, and her horn stopped glowing, and suddenly Pip could move again. As she stood, her body faded into a muddled illusion for a bit, before reforming... as Princess Luna. The dark blue mare smiled down at Pip, still taller than he was, but somewhat less so now. She took off the pieces of Nightmare Armor, and took out the false fangs she was wearing, sighing and shaking herself a little as Pip watched, confused but entranced.

"P-princess Luna?" He asked, incredulous. Somehow, she was now even more alluring, somewhat less intimidating, but even more beautiful than she had been before. "Princess... what... how... why?"

"To answer those in order, the Nightmare Moon facade is simply that. It is a character we play, a ruse to make the common pony fear us and leave us alone. As to how, over a Thousand years ago, I began to wish for my freedom from the rigors of life as a royal, and where better to turn than the endless vast of the open sea. I spoke at length with my dear sister about it, and she came up with this idea. We staged a fight, we were 'defeated', and exiled to never set foot in Canterlot ever again, and thus we took up the mantle of the Moon Maiden of the High Seas, Nightmare Moon. Why, however, is a little bit more complex." She picked him up with her magic again and set him on her bed, then lay down beside him, one hoof gently petting his shoulders.

"You see, Equestria has always faced enemies from without, and our dearest sister knew that something had to be done. So, with a heavy heart, when we came to her seeking freedom, she tasked us with something beyond the scope of a mere Princess. We were to become a terrible force, you see. A force so unfathomably powerful that nopony could ever hope to truly challenge it. The Equestrian Navy had gotten overconfident and Lazy in the years prior to our 'transformation', so when we changed into Nightmare Moon, we caused a great deal of damage, sunk many of our own ships and stole the ship we sail upon now, which was once called the 'Jewel of the Royal Navy', and named the "ERN Daystar" originally. Over the last thousand or so years, we have been collecting crew members, sailing the high seas, and fighting off threats to Equestria's safety that most ponies never even heard about or knew existed." She sighed heavily, taking a few moments to breathe before going on. "Recently, in a battle with some rather cutthroat scurvy Diamond Dogs, several of my crew were injured, including my long-time maiden-in-waiting, Sea Salt. We decided to let her retire for a time to a safer location, and set out through the dreamscape in search of a young, charismatic stallion with the strength of will to do what it takes to serve us..." She reached over and pulled his face over towards hers with one hoof, smiling warmly as she leaned in closer. "...and serve us in soul, mind and body."

Pip had been listening in rapt attention, but now his attention was fully back on those shining, dark, beautiful eyes that were looking intently at him. "P-princess... I am not worthy to serve you, but if you wish it of me, I will be yours... in every way, until the day I die!" Something in Pip's mind flipped on like a switch for a moment, and he leaned up and kissed the big, beautiful mare before him, lips locked with hers for several long, heated moments.

"How brash, young Pip..." The princess spoke softly with a stern expression as she pulled away, leaving Pip about to say something. She pushed her mouth back against his and kissed him passionately, her tongue slipping into his mouth and her hoof stroking at his cheek softly as she kissed him for a good, long while. She smiled deviously as she pulled away, leaving Pip breathless. "We love brash."

"Princess?" Pip spoke up, a little hesitant. "Will I ... really have to risk my balls in your service? I mean, I meant what I said, I readily will if you ask me to do so, but I felt inclined to ask..."

At that, the Princess fell backward with a hearty laugh, before righting herself and leaning over the smaller stallion, nosing him onto his back again. She reached up and cupped his precious jewels with one hoof, and smooched him lightly for a moment before she spoke. "You probably will not, dear Pip... but if you're lucky..." She stroked her hoof back up his slightly tamed hard-on, bringing it back to life slowly. "...you might just have to use them instead."

She pushed Pip up the bed, til his head was resting on the pillows, and calmly spread his legs apart with her hooves. She then stood up on the bed, and positioned herself over him, surprised at how close the end of his shaft was to her. Using her magic to guide him, she straddled him a little wider, closed the distance by lowering her hips, and very gingerly slipped his tip into her soft, moist entrance.

Pip was over the moon at this point... well, more literally under the moon, but the point remained, he was ecstatic. He couldn't help a little bit of breathy whining as he felt himself slip into the Princess, her warm and welcoming insides clenching around him rhythmically somehow as she pulled him further and further in. His hips bucked a little bit out of instinct as he got nearer and nearer to meeting hers, and surprising to them both, soon Pip was hilted fully in her and throbbing slowly in time with his heartbeat.

"Oh p-princess... this feels astounding!" He sighed happily, unsure of what to do next. "What would you have me do now?"

"Leave that pa-ah!-part to us, young Pip, for now, all you need to do is be here for us..." Luna smiled down at him again, and with a wiggle of her hips, she started pulling herself back up away from him... before sitting back down again before he'd halfway come out. Her crotch met his with a satisfyingly squishy sound, and the princess had to contain a giggle from the cross-eyed look on poor Pip's face. "Thou has not ever truly lain with a mare before, hast thou?" She teased, leaning down a little to kiss the top of Pip's head. "Tis alright, we shall educate thee, and thou shalt learn by doing!" As she said this, she sat down again, causing young Pip to groan a bit louder.

"Y-yes My lady! T-teach me to please you and I sha-HAAAH-hall never stop!"

"Th-then brace thyself against the bed, with all 4 hooves, and when we come down, push thy back and hips up to... to meet us!" She gasped a little, once more burying him deep inside her, before lifting up again to see if he'd follow her instructions. When she came back down again, he pushed up hard, his crotch meeting hers with a lightly audible slap, and his balls bouncing off her ample posterior. The meeting was good though, so much so that it caused her to gasp again, loudly. "Y-yes! Again! K-keep going!"

So Pip went again... and again. He didn't know where this sudden burst of stamina was coming from, but he was thankful for it, as he pushed every fiber of his being to the limit attempting to please his princess. The further along they got, the harder Princess Luna seemed to sit herself back against him. He could feel her body shudder every time she slipped his medial ring past something sensitive or through her clenching entrance, and he could see her biting her lower lip hard to keep from crying out.

Suddenly, she stiffened for a long moment, the whole of her trembling and quaking heavily, before she finally let out a husky breath and started moving again, but this time, much more unevenly. Her mane, magical as it was, was just ever so slightly askew after that moment, and her insides around Pip's rod quivered like he was made of ice. Her breathing was labored and somewhat ragged, and her fine coat was growing moist with sweat from the exertion. Finally, after a minute or two more, she sighed out heavily, and sat fully back down on top of Pip, panting.

"Young Pip, thou hast bested us... we cannot continue as we are. Wouldst thou instead wish to switch places, so thou might finish as well?"

"If you wish it, Princess, I will do whatever you ask!" Pip smiled brightly up at her, a little sweaty himself from the hard work.

Luna simply nodded, and with her magic, she quite literally turned them upside down from how they had been, her now laying on her back, wings spread below her, and Pip no standing on his hind legs, still buried balls deep inside her. She smiled as he struggled to find purchase for his back hooves a moment, but then gasped as he took hold of her right hind leg with his forehooves, and lurched back into motion again.

Pip had sort of gotten the idea from what he was doing earlier, and instinct was helping to move him along as well. He held tightly to the muscled rear leg of the moon Princess, drew his hips back, and then thrust them forward again, over and over and over. He couldn't help moaning every now and then, as occasionally his lover would clamp down around him and make the going a bit slower for a bit. His poor balls were getting a little tender from bouncing off the underside of Luna's tail so many times, and it was making him tire out just that little bit faster. However, he did want to please his Princess as best he could, so he buckled down and tried hard.

Luna was quite impressed with little Pip so far, and as she watched him strain and grunt and moan as he fucked her, she couldn't help but smile. For some reason she was quite taken with this young stallion (and his mighty oak of course), and stroked his cheek softly a few times with one hoof while he worked. She was also quite enjoying the feeling of his balls bouncing against her, and she swished her tail from side to side below him just to tease him a little more. This proved to be a tiny bit more effective than anticipated.

Pip felt Luna's tail brushing against his nuts, and the tiny bit of extra stimulus proved to be just enough straw to break the camel's back. Pip felt his balls tighten up to his body, a fire building in his innards, and he went for broke. His tip flared up inside the bigger mare, surprising her with its size, and she gasped loudly as she felt him continue hammering away with his flare fully inflated. Then after a few long moments, Pip groaned loudly and buried himself as deeply as he could, and let loose the torrent of seed he'd built up. He marveled to himself how long the climax lasted, never having cum so hard in his whole life til then. Once the wave subsided though, Pip lost his grip on Luna's leg and kinda collapsed on top of her, panting wildly.

"Did... did I do well, Princess?" He managed to weakly coo out at her, trying and failing to lift his head from her belly to look up at her.

Luna, meanwhile, hadn't ever been so vigorously rutted before, and having come again was a mite disheveled. She huffed a little, her whole body sore like she'd fallen down a hill, and tired beyond belief. All from this young stallion and his youthful eagerness to please her! She'd make no mistake in future; this little pony was a mighty lover. She reached down and softly stroked his mane and neck a little, shivering as she felt his towering erection slowly fading from within her, still feeling quite full from his climax.

"You... you did wonderfully, dearest Pip." She cooed back, waiting for him to pull out of her fully before tugging him upward into a close embrace, nuzzling his chin and smiling brightly. "For one so young and inexperienced, your stamina alone has impressed us." She smooched his nose softly. "We think we shall keep you." She giggled a little.

"So..." Pip looked up at her hopefully. "...does that mean I can join your crew? That I can be a pirate and sail the open waters with you for the rest of my days?"

"Well, Pip, we do need a new Valet, never had a stallion as one before, so let us both sleep on the matter. When we wake, we shall eat and drink, you shall help us Bathe, and we shall discuss the terms of your employment then." She nodded with some finality, going back to stroking Pip's mane and shoulders a little.

Pip nodded a little and yawned, tired from the efforts but satisfied like never before, and curled up closer to the mare of his dreams, safe and warm in her embrace.

'Tomorrow,' He thought, 'Tomorrow my life truly begins...'

Author's Note

Well, there you have it! Chapter 1, over and done! This was supposed to be a warm up that turned into a thing on its own xD

Hope you all enjoyed, and as before, drop a comment if you did!