Jacob took odd requests before, but nothing like this. Being a pirate meant smuggling goods was a common job. Illegal liquor, contraband weapons, bootleg exotic goods, and even the occasional traveller. None of these quite compared to the task before him. Sure, the pay was good, but he didn’t like carrying larger goods.

Before Jacob was one of the most massive beings he’s seen in his life. The two of them were in an empty field, the giant idly tapping their foot as he approached. Each step shook his world more and more as he finally made his way to their boot. The sounds of metal rattling filled the air as they let out a sigh, carefully making their way to a seated position in front of him. Taking off their helmet, Jacob was greeted with a surprisingly familiar face.

Anna Luxam was probably the most famous knights of recent time, daughter of some important noble from the north. It must’ve been a joke, right? Why would someone like her need him to escort her? Things didn’t add up, yet here she was.

“Hello, little one. I’m guessing you’re the one who signed the contract?” She spoke in a hushed tone, trying to not draw too much attention to their meeting. As if there wasn’t one of the most popular faces in all of the land taking cover in an open field. “I guess you weren’t really expecting me.”

All Jacob could manage was a confused nod, looking around to see if this was some sort of trap. The king’s army couldn’t be here right? He didn’t see a mountain range of armor approaching, so it seemed safe. Though, he doubted Anna would need any extra help with someone like him. “I guess I was expecting someone… smaller?”

The following giggle rattled his bones as he shivered. “I’m sorry to disappoint then. Though, the pay is definitely worth it.” She was right. The pay was nothing like he’d seen in months, and his stomach grumbled at the thought of being able to eat fresh food for once. Her expression flattened out as she looked to the distance. “I wish to leave the country. I was told you’d be able to help me; you’re apparently the best in the business.”

He almost burst into laughter. Him? Help her? Best he could currently do was throw a large blanket over her and pretend she was a hill. Why would someone like her wish to leave the country? Fame and fortune thrown away, for what?

“I know you find it absurd. I can see it on your face.” She let down her blonde hair, untying her ponytail. “But you know the land. I’ve spent most of my life as a soldier, I want to see the world.”

“This has to be some sort of a joke, right? Where’s the rest of your unit? I would think I’d remember signing a contract from someone of your size.”

“I doubt you could even pick up the quill, much less sign it.” It seemed she didn’t appreciate his comments. “But you did. I sent a messenger of your size. It seemed much more appropriate.” Her shadow grew over him as her hand pinned him against the dirt. Her sincere smile had since long been replaced with a cold frown, the expressing cutting like daggers through his soul. “I’d like to get moving soon, though. As enjoyable as our little chit-chat was, the guard will start searching in a day or so. And you signed the contract, no ifs ands or buts.”

She pushed down against him slightly, the air leaving his chest as she almost carelessly threatened to crush him if needed. The pressure released, her digits slowly closing in on his dazed body as they familiarized him with its somewhat comforting, but tight grip. “I’m going to have to put you somewhere safe for now, so don’t make too much noise, or I will make sure that you rot in prison for the rest of your life.”

She brought her other hand to her lip, carefully thinking, smirking, prying off her boot as she dangled him over the entrance. Heat wafted upwards from the makeshift prison inside. The humidity was almost unbearable, almost tangible enough to cut with a knife. It took a moment longer, but odor hit him the hardest. It was clear these boots accompanied his client for many battles, and that they would be with her until they fell apart. “I’d say I’m sorry for this, but until you’re a bit more agreeable to what you promised, you’re taking the trip beneath me. Get acquainted.”

The plummet was fast, his body hitting the insole as leftover sweat splashed against his body. He didn’t have time to argue as the light left his world, the socked sole slipping inside the boot, sealing his fate.

Jacob was unsure of how much time had passed. The now familiar rhythm of gripping and releasing was almost comforting to him as he was pulled against her socked digits, then slammed into the leather insole of the boot. Well, as comforting as torture could be. Each step pushed his body to the limit, to which he now was unable to feel much past his neck. He was sure that he was bruised and battered at this point, and doubt he could even run if he wanted to. The steamy sock pushed into, almost as if to solidify this point as more grime covered his body, the sweat pushing out of the presumably once white sock.

After what felt like ages of walking later, Jacob could overhear a conversation just barely, the rhythming footfalls becoming slower and slower as he heard a big sigh from above. Anna slowly pried off her boot, a gust of cold fresh air flooding into the boot causing him to shake in the drastic change in temperature. His lungs felt like they were burning as the cold tavern air filled his breath, slowly breathing in and out. Soon after, the familiar hand of his captor reached in, and Jacob did not fight this time.

“Oh? What’s wrong? No mouth on you this time?” Anna teased, pouting as she dropped him onto the wooden bedside table. A gasp of air pushed out of Jacob’s dry mouth as he tried to croak out some form of answer to his tormentor, instead coughing up the last bit of sweat choking him. “Hmm… thought you were supposed to be some form of pirate. I couldn’t imagine you outrunning a child, much less any guards.”

Jacob tried to pull himself up to a sitting position, but instead winced from the surge of pain that shot up his body at the slightest movement. “Stupid-” He didn’t have time to continue the thought before getting the wind knocked back out of him by a sharp flick to his chest. If he didn’t feel anything below his neck before, he did now. It stung as if a heavy weight was thrown into his chest.

“Would you like to continue that thought, or will you be aiding me as your contract states?” Anna started to pry off the plates of her armor, then followed by the mail, a simple tunic and pants remaining after discarding them to the side. It was clear that she had been walking through rain and mud, and was more than eager for this conversation to be over. “I don’t mind you spending another day in my boot, though your body looks like it’s going to fall apart.”

Jacob only nodded, wanting to flinch as Anna held her hand above his body. A familiar glowing circle hovered away from her hand as his joints slowly moved back into place. The entire process felt gruesome, but he could finally feel his body once more, sitting up.

“I just don’t really understand why someone like you would need to flee the country.” Jacob croaked out, presented with the cap of a canteen. He took a desperate sip, letting out a small sigh as he continued his thought. “Not to mention, you were wandering around in your own armor. Isn’t that a little bit suspicious?”

Anna opened her mouth to argue, but simply nodded. “Would’ve had more time to sort these things out if I wasn’t stuck carrying my guide in my boot.” She fished into her bag to pull out a large cloak, holding it in her hand. “Thoughts?”

“That just kinda screams ‘Mysterious Stranger’ to me.” Jacob’s stomach grumbling was greeted with a small chunk of cheese, much to his pleasure. “I have a few ideas though…”

***

Anna was dressed in typical pirate gear, only missing a flintlock and a proper cutlass. Which was to mean, most of the reasonable clothes she had was mostly haphazardly torn, while she covered her face with a bandana.

“I look stupid.”

“Are you saying that I look stupid normally?” Jacob scoffed.

“Maybe.” Anna picked him up with a grin, depositing him onto her shoulder. “There! My parrot! Squawk for me!”

“I’d rather die.”

“That could be arranged.” Anna set him back down onto the bedside table, taking a seat on the bed. “To answer your question from before, I wish to leave the land. I want to experience new things, and I don’t want to be followed everywhere I go, or for people to constantly fear my presence. I want to heal the land I tore apart. Isn’t that enough?”

Jacob was at a loss for words, simply nodding as he turned to face away from the giant knight. “Well. You better get some rest for now. You’ll need the energy for tomorrow.”

Anna simply smiled.

Jacob rubbed his eyes, blinking as the sunlight peeked in through the inn’s window. After last night’s conversation, Anna offered the small pirate her glove to sleep in, a bed that made him feel humiliated, but beat laying on the hard wooden surface of the table, or being flattened by the rolling slumber of the giant knight. As the thought passed through his mind, his companion would groan in her sleep, rolling over to face him as she snored, her dirty blond hair messily tangled over her face. Each breath pushed a few loose strands away and back towards her.

He would use this time to carefully slip down from the table by jumping towards the bed, gripping the blanket as he slowly used the cloth to safely reach the floor. Sneaking over to her bag, careful not to make too much noise, he’d search her satchel. The worn leather bag had two scrolls stuffed in the top, rolled out to be old military maps of the surrounding areas. It seemed that Anna had been avoiding any direct contact by traveling through towns with smaller military presence.

The loud snores above reassured Jacob that he had more time to poke about, finding a large copy of his contract. He could tear it up now, though he doubted that he could get out of the room without Anna’s help. He’d be forced back into another if he was careless, and he wasn’t eager to spend more time in the makeshift prison of yesterday. He’d shudder at the glimpse of the boots discarded in the corner.

He’d find a journal, wrapped in a chain. The front of the book was bound with a lock, securing the thoughts within from the prying eyes of a certain particular tiny.

“Great, where would I even find…” As Anna rolled once more, Jacob could make out a small necklace, a silver key hanging from the chain. “Of course.”

Gripping the sheets once more, the pirate would make the slow trek back up to the bed, ending up at the foot of the bed. Avoiding his prior tormentors, he’d move past the sweat-covered body of the sleeping knight, slowly following the outline of her body to her chest. As he carefully pulled himself onto her chest, he’d work at undoing her necklace, disconnecting the chain to slip the handcrafted necklace off into his grip.

“Satisifed with your little heist?” The words made his blood go cold. “If you like spending time on my chest so much, you’ll love today, stupid pirate.”

***

Being stuffed in Anna’s cleavage wasn’t nearly as bad as the boot. Sure, being smothered with each bounce of a step was brutal. Sweat would soak his clothes as he wrestled not to drown in the supple soft flesh. Each surfacing was met with an eager finger ready to push him back down deep within the depths of his flesh prison. But, at least Jacob could hear what was going on better.

From what he could pick up, they were in some sort of a market. Every so often, Anna would stop, chatting with a vendor about some item that caught her eye, occasionally searching her back for her pouch of coins. This would result in a tight squeeze as she’d reach over to her side, squishing the poor pirate in between her chest.

***

“I’m going to take you out now.” Anna’s digits pushed through her chest, pulling out a dazed and pummeled tiny, holding him by his leg as he swung back and forth slightly. “I’m going to give you two choices here. You act like a grown adult, sit on my shoulder, help guide me like you’re supposed to, or…” Anna would pull out a cage from her bag. “You sit in this pet cage, and I’ll strap it to my waist. I think it’s a bit tacky with the outfit, but one way or another, I need your eyes here.”

Jacob would cross his arms, huffing, only to be met with a rather strong fling into the cage, the door slamming shut as Anna locked the cage with the chain from her journal. “Your loss, squirt. Thought you’d come around, but looks like you’re just like a pet. You need to be trained.”

“You’re going to be in this cage until you start being helpful. Trust me, you don’t want me to find ways for you to be helpful, so I’d suggest you’d start helping. Maybe I’ll give you a little food as a reward too. Though my boot feels a little empty without my personal insole. Maybe that will motivate you?”

It was going to be a long day.