I
Dilan couldn't believe his eyes, it actually worked, he managed to summon a servant. Doing so outside of a holy war and without any sort of magical affinity. A pink-haired woman, dressed in a risqué-pirate Halloween costume appeared in the antique-filled study of the old mansion, where the young man had performed his ritual. The newly manifested servant looked around with a raised brow. Her ocean-blue eyes slowly scanned by all the shiny trinkets the old house had on display. With an intrigued smirk she turned towards the young man who'd summoned her.

"Don't tell me you're my new master," she said, walking up to Dilan, her heeled boots thumping against the wooden floor with each step. "You're just some kid."

For every two steps the woman took forward, Dilan took one back. Stuck, undecisive on whether or not to stand his ground and prove his maturity, or step back in pace with her, admitting the unweathered boyish fear he felt at an older, more-confident woman's approach. Despite taking offence to her comment, the young man couldn't utter a word to combat at her. 

Despite his youthfulness, he was still a nineteen-year-old standing a head taller than her. Yet, something about the lady's demeanor proved that height didn't matter. Apparently, all she needed was to call him boy, and smirkingly walk forward to have him fall of off his horse. All he could do in response was break into a nervous sweat.

Dilan's insecure steps backwards were halted, as his back pushed against an old, built-in bookcase. The woman closed in on him, bearing a toothed grin. Shyly looking away from her face, lead Dilan's eyes to lock on to her pair of massive breasts, bursting through her long, red pirate-coat, resulting in an excessive skin-revealing cleavage, the sight of which made the young man even more flustered. The woman walked right up against Dilan. Her breasts squeezed against his lower ribs, while she looked up at his face. With a smile, she pinched his cheek between her fingers.

"What a lil' treasure you are, eh!" she said. "Bet a boy as soft as you, is in desperate need of my services. So, where is your war? Let's be done with it and party!"

Dilan looked down at the woman, who stood at about 5'4" (162cm). She had a massive scar across her face. Her long magenta-pink hair, bend and fanned outward, as if her hair was stuck the way the wind had blown it. 

The young man could barely keep it together, feeling her chest press up against him, while he was being cheek-pinched like a five-year-old child. Too shy to rudely push the woman's arm away, the best he could do was tap it, to try and signal her to stop. With a scoffing smile, the woman obliged and let go, clearly entertained by her new master's timid character.

"There isn't really a war," Dilan said.

"Huh?"

"I just summoned you to see if I could."

The woman's mouth went agape, before growing into cheer and delight. "Ah, fantastic. So, I don't even have to fight anyone! You just summoned me to party and take your stuff!"

Dilan frowned. "Wait, sorry what?"

The woman grabbed the back of his head and pulled it to her chest for a hug. All the boy could do was muffle with wide open eyes, while his face got buried into the squishy bare skin of the woman's bosom.

"Oh, little master," she said. "You're truly a man of my ilk, we are gonna have the time of our lives you and me!"

The boy managed to squirm his head free, "W-What no, hold on, who the hell even are you?"

The pirate lady stopped hugging him, and pushed his shoulders, sending him bouncing against and off the bookshelf, before tumbling back onto the floor, right in front of her boots.

"Do you even need to ask?" the woman said, striking a pose with legs spread and her hands on her hips. "I am Francis Drake, El Draque, King of Storms, and drinker of your alcohol!" 

"My name is Dilan. Sorry, what was that last title?"

"Oh, I'm sure you heard me," the woman said, stepping over to the boy she pushed over, before reaching her hand out to help him up. "Speaking of which, where's your rum?"

"Uh, the estate has a wine cellar," the boy said, taking her hand and standing up. "Don't know about rum though." 
As he stood in front of her again, something seemed off. Her big blue eyes stood at the same height as his own. Had he grown smaller? The pirate had noticed it as well. She furrowed her brow, and held a flat hand above her head, before swinging it forward, and jabbing the side of her palm into her master's forehead.

"Huh…" was all she had to say about it, before she turned around and walked out of the study.
Rubbing his forehead, Dilan ran after her. "Wait, hold on, where are you going?"

II
As the two of them made their way through the massive estate, which used to belong to the orphan boy's parents, Dillon kept trying to stop his new servant from grabbing things and stuffing them into the carpet, which she had repurposed as a loot sack.

"Hey, hey, hey! Just cut it out!" Dilan said, pulling a little golden horse statue from her grasp.

"Spoils of the job, kiddo," Drake said. "Now take me to this wine cellar of yours, or I'll ransack the entire place."

Starting to wonder which of them was the master, and which is the servant, Dilan showed the pirate down the flight of stairs, where they entered an old looking cellar, with cracked brick walls. The gothic looking room was lit with dusty, and loosely wired lightbulbs, revealing rows upon rows of bottle racks.

"Seriously," she said, with a giddy smile. "I will never understand people's need to put their drinks away in old basements, stockpiling them for a later that may never come. You get your hands on a drink, you should drink it, I say. Live in the here and now, you know?!"

Dilan shakes his head, looking though the bottles and checking their labels. The servant he summoned was a complete whirlwind, which he could not get a grip on. But even if he knew how to send her back, he probably wouldn't. For all her crazy, she was kinda hot. He looked up and noticed a couple of bottles with wide, thick bodies and thin necks, their label clearly reading rum.

"Hey, I found some," Dilan said.

He tried to reach for them and stretched his entire body, but couldn't quite make it.

"Let me see," Drake said.

Dilan turned around to look at her, but was met with her bare chest, as she walked into him. He again received a face full of cleavage, as the woman reached up on her tip-toes, to grab one of the bottles, pinning the boy against the shelf. There was no way he was small enough to end up in such a position. Was his head really at this woman’s breast-height? The high-heels of drakes boots hit the ground again, giving him some breathing space, and the ability to look up at the obviously taller woman, while one of her breasts continued to push into his cheek. The pirate lady checked the label and smiled.

"Yeah, that's the stuff," she said, looking down at the boy stuck against her breast. "Hold your breath, Master. I'm gonna grab a few more of these."

She reached up, smothering the poor guy again in skin and squish, while handing him a bottle to carry in each hand. Dilan couldn't believe how humiliating this was, couldn't she just take one step aside, or allow him to move away? Did she really need to force her chest in his face? She had to know what she was doing, and was probably drowning him with her chest, just to tease him. As embarrassing as it was, Dilan had to admit, He this was every man's dream come true.

"There, five should be enough," Drake said. "We can always come back for more."

The pirate took a step back, and turned to walk out of the wine cellar. Dilan, stunned and gasping for air, clumsily followed behind her, his hair pushed completely out of form by the woman's breasts. As they walked back, Dilan almost tripped over his own pants. The boy looked down to see his clothes had become too large for him, and hung like large sacks on his diminished frame. Drake made her way to a large guestroom, hugging two bottles to her squishy chest, while keeping a third held between her breasts. She looked back to see her master attempt to keep up with her.

"Well, look at that," she says, "you really are getting smaller. You look like a little kid who put on his dad's clothes!"

"Do you have any idea what's going on?"

"Beats me, I guess this is what happens when you mess with experimental magic."

III
The woman threw her loot carpet aside and set her bottles down on the guestroom's table. The room was huge. More bookshelves adorning the walls, and a large fireplace shining a homely glow onto the large black leather couches around the glass table.
As Dilan went to put his two bottles next to hers, Drake laughed.

"Aw, how strange," she said. "This stuff is really progressing fast."

The boy looked at his body, he was drowning in his clothes at this point. He stared up at the short woman, who now towered over him. He estimated he must've been 3'10" (117cm) at this point. This was becoming a problem. Dilan decided he should probably stop helping his servant collect booze, and check his study for answers. Just as he was about to turn and leave, Drake dug her hands under her own chest and lifted her breasts. The boy looked up with wide eye's she held them above his head and dropped them. The two heavy mounds slapped on the top of his head, pushing his neck into his shoulders under their weight. The pirate cackled hysterically.

"Hah, look at you, Master," Drake said. "you're the perfect height to be my little breast holder!"

Dilan crouched out from under her bosom, and stepped away. "Ok, we should probably take this more serious. If I keep shrinking this could end badly for me. I'm going to look for a cure."

His wayward servant simply smiled and picked him up like a child, holding his entire upper body against her chest, before walking him to the couch and sitting down.
Dilan couldn't believe he had already gotten small enough for her to do that. He couldn't help but blush, entranced by how much bigger her already huge chest had become. For a moment he submitted, and lay his head against the soft pillows, enjoying the strange experience, taking note of how her body gave off the smell of the open ocean. Maybe this wasn't so bad, the softness and warmth of his servant was actually quite comforting at his size. He shook his head and snapped out of his moment of surrender.

"No, Drake," he said, "We have to fix this, I could end up shrinking into nothing by the end of the night!"

The pirate grabbed one of the bottles and bit the cork off with her teeth. "Then we should party and live your last night on earth to the fullest!"

"No, no! We should find a way to fix this!"

His servant completely ignored him, and chugged down the first half of a one-liter bottle of rum. She offered him a sip, which he refused.

"I'm not of legal drinking age."

"Suit yourself, more for me!"

And so went the rest of that bottle. The magenta-haired woman let out a satisfied sigh, and an informal blench followed not long after. She hugged her arm around the boy and pressed him closer into her chest. All Dilan could do was squirm up against the woman's voluminous breasts, and beg her to help him, as she opened up another bottle, and drunk herself into a permanent blush. 

IV

For the next hour Dilan was stuck in his servant's lap, and hugged tightly against her chest, while the woman rambled tall tales, and sang some slurred verses of forgotten sea shanties. It took her a while to realize her master had shrunken into his own clothes. Removing the shirt and pants, she stared at the one-foot (30cm) tall man in cheerful surprise.

"Well, well, you seem like a very precious doll," Drake said. "Seeing as you're small enough for me to steal, I guess I'll do just that."

At this point Dilan couldn't fight it anymore, his struggles and pleas were pointless against his now giant, drunken servant. He blushed, hearing she was going to steal him, and barely squirmed as she picked him up, the warm and soft skin of her palm and fingers squeezing around his now, naked body. She raised him up to her face, and took another sip, before lowering him down into her cleavage until only his head stuck out of her massive mounds.

"I can't believe I'm saying this," Dilan mumbled, "but this actually really hot."

Drake giggled with a hiccup, "That's the spirit, here take some of my drink."

The woman started to tilt her bottle overhead.

"Wait, no!" the boy squeaked. "I'm not old enough to drink!"

His pink-haired servant poured the bottle into her cleavage, drenching her breasts (and the poor boy stuck in them) in thick, sticky, alcoholic liquid. Dilan coughed and cried out for her to stop. The woman let out a dirty laugh, and brought the bottle back to her own lips.

"Such an ungrateful little landlubber," she said.

The boy shivered as he noticed he had shrunk well past one foot by now. As the pirate saw her master disappear between her breasts, she put her bottle aside and lay down on the couch. She began to fondle herself and squeeze her chest together. She laughed as she heard little screams and moans coming from her cleavage, as the boy inside both enjoyed and dreaded the odd massage. Dilan was overwhelmed by the massive hills of flesh pressing against him. The woman's warmth and softness too much to bear. Her skin squishing almost perfectly around him. It was both a heaven of its own and a hazard that could send him up to the real thing. Drake continued drunkenly squishing her master between her breasts for a few minutes, until she decided to take a break and drink some more.

Dilan tried to catch his breath, trapped in the bosom of his giant servant, who seemed to have no interest in helping him. At least the pirate had stopped trying to crush him with her breasts. Above of his fleshy prison, more bottles got poured down the hatch. From her cleavage he could hear the gulps nearby. Over the course of the next hour, Drake drank, and slowly forgot about her master, as the poor guy had to get comfortable with, what he imagined his new home to be for the rest of the night. Stuck in the warm sweaty cleavage as a sticky layer of rum coated his body. 

V
After a while her fingers dug back into her cleavage. Did a small squirm alert her, or did she finally remember he was in there? While for the past hour, Dilan's entire world had been boob-squish, he hadn't been able to keep track of his ever-diminishing size, and wasn't ready for the shocking reveal. The young man could feel two new surfaces of skin pin his body between them. These weren't as soft as Drake's breasts. The skin had a rigid texture to it, were they fingerprints? Dilan's heart started racing. Had he really become small enough to fit between his servant's fingers? 

He felt himself getting pulled up into the light, right in front of the lady's face. The squinting blue eyes of the drunk pirate, were unfocusedly trying to determine whether what was between her fingers was a bug, or a human being. She carefully pressed her thumb and index finger together, causing the boy to release a masculine roar of pain in response to the crushing pressure of her squishy digits. Hearing the high pitch little squeak emanate from between her fingers, caused the drunk to grin in delight.

"Ara, ara, Master," a deep woman's voice thunders. "Seems like you really are shrinking down into nothing. Maybe you should have looked for a way to fix this, instead of partying with me."

Dilan's face turns red in rage. "What, you're the one who said-"

"What was that?" Drake says. "I can't hear you anymore, you're too small."

The pink-haired pirate puts her other hand in front of her mouth, and giggles into it. All Dilan can do from between the giantess' fingers, is look at the woman's massive face, laughing at him and mocking his fragile state.

"Oh, poor Master," she says. "Aren't you a bit too young to be held under a woman's thumb? Hmm, whatever shall I do with you now?"

Drake's eyes glance over at small model-ship standing in one of the bookshelves. She looks back at the little guy between her fingers, and grins.

"Perhaps I should teach you how to sail, before you're small enough to drown in my sweat." She says, jumping out of the couch, and drunkenly wobbling for a second, before she finds her balance, and walks towards the bookshelf. "Don't worry master, I'll make a pirate out of you yet!"

VI
The heels of Drake’s boots hit the floor, as she got up and stepped towards the shelf. She held her little master between her fingertips, no far from her ocean-blue eyes, so he could see the exact same thing she’s was looking at. An old model ship of a colonial-era, two-mast sailing boat. Dilan turned to look at the woman, who tightly squeezed him between her fingers, and could read the playful idea off her face.

“No,” he said, “we really don’t have time for games like this.”

The pink haired woman frowned. “I still can’t hear you, but I guess you’re just complaining like a dry sponge again.”

She brought her fingers over to the little ship’s deck, and let the tiny boy fall twice his height, onto the dusty surface of the model. For just a second, it gave the young man the illusion that he was back at a normal height. That illusion was quickly scattered however, when the scarred, giant face of his servant loomed over the little boat.

“Ah, look at that, captain of the ship,” she said, with a suppressed giggle. “The vessel fits your size like a glove.”

Dilan gave up trying to talk to her. Either she really couldn’t hear him, or was intentionally pretending not to, and he wasn’t quite sure which was scarier. While she was right, and the ship really did fit his size like it was designed for him. If the shrinking continued, he’d soon be a bug on the floor of even a miniature ship’s deck.
Darke smiled, as her hands reached for the boat, “Come on, let’s take this little ship to the couch, and give you some sailor practice.”
Her palms pushed up against the bottom of the hull, while the pink tips of her fingers peered out on all sides of the deck, like the tentacles of the dreaded kraken. Dilan could hear the woodwork around him creak, as the boat was lifted off the shelf. As his gravity began to shift, he ran for one of the masts, and hugged the pillar. While the giant pirate was trying to carefully take the boat with her, it was a drunk woman’s idea of careful. Meaning Dilan’s safety was as much in is own hands, as it was in her enormous grasp.

Drake sat down, and immediately swung her legs into the couch, to lay on her back. She rested the boat on the cervices of her cleavage, and used her fingers to push one of the mounds aside, creating space for the vessel to sink a bit deeper between the two fleshy behemoths. Once the ship was stuck, and held in place between them, the floor beneath Dilan’s feet became steady again. The front of the ship was a little tilted towards his servant’s face, but he could let go of the mast, and move around freely again.

“Oh, looks like you’re the only one manning the ship,” the pink-haired tease said. “Better get steering.”

Dilan was getting fed up being played with, and refused to go along with the woman’s game. Drake lips grew a confident smirk however, knowing just how to motivate the naked little captain. She blew her cheeks round, and released a warm gust of wind from her mouth. So powerful in send the model’s dust flying, and forced Dilan to cover his eyes. Her breath was so strong it almost knocked him over. The pirate let out a bully-ish laugh, which caused her chest to bounce, and the ship to shake along with it.

“Better take point Master~” she said.  “There’s a storm on the horizon.”

Dilan couldn’t believe what was happening, and couldn’t imagine any of this ending well. But all he could do was play along. He made his way up the stairs to the wheel and clamped his hands onto it. The entire thing was just a model of course, meaning the steering wheel wasn’t even connected to any other part of the ship. In only such a short time, he’d shrunk again. While he was dropped on the ship, tall enough to be its captain, at this point he was the height of a child on it.

“Oh, big waves incoming!” Drake said. “Hang on tight lil’ sailor~”

The servant began to press her hands into the sides of her chest, causing her tits to wobble against the boat. Sending the vessel into a waving motion that quite accurately simulated a stormy night. Dilan had to regained his footing a few times, almost tumbling off his steering wheel. Playful laughter vibrated throughout the entire ship, as Drake continued to massage her chest on it. But, the poor model wasn’t designed for the punishment she gave it. The hull began to crack against the pale, squishy skin of the woman’s breasts. Little pieces of wood, so meticulously placed, snapped against her merciless, malleable curves. Dilan squeaked in surprise at the sound of his ship coming apart inside his servant’s cleavage, before another heavy gust of rum-flavored breath-wind blinded him.

“Very good, Master,” she said. “You got better sea legs than I gave you credit for. Let’s see if you can take the splash of a really big wave.”

The pirate, laying spread out on the couch, grabbed a bottle of rum, on the table beside her. Dilan looked on in horror, as with a toothed smile, she brought the neck of it, right over him, and poured the alcohol right onto the model. There was no regaining his footing this time, as Dilan’s feet slipped on the woman’s drink, sending him sliding over the side of his ship, right into the dark crevice of the sea-monster’s cleavage.

“Oh, Master are you ok?” Drake said, with the first genuine sounding tone of concern that night.

She raised the boat off her chest, and carelessly dropped it onto the floor beside the couch, causing the wreckage to scatter into pieces. With both hands, she pulled her cleavage open and squinted, trying to find her master, who had, with another shrink-spurt, become the size of dust.

“I guess I overdid it a bit, didn’t I,” she said, her concerned frown, quickly fading into a party-girl smile again. “Well, I guess we have a general idea of where you are.”

Dilan could hear every word, as the rum sticking him to the skin inside her cleavage, slowly dried him stuck to his servants’ breasts. The pirate removed her hands from her chest, and the two mounds closed together, pressing her little speck-sized master into her warmth, were he’d squirm in fear, against curves he’d become too small to even dent, until her heartbeat lulled him to sleep.

Before she drunkenly fell asleep as well, Drake’s voice vibrated throughout her chest. “I guess he’s lucky, isn’t that’s the type of sea every man would love to drown in anyway?”