tagCelebrities & Fan FictionJon Chess: Cabin Boy

Jon Chess: Cabin Boy


The rogue that some knew as Jon Chess slept fitfully but that was not the amazing part; that he was having the best dream he'd had in years was. Jon Chess had recently been tortured, which had included a shadow priestess rewiring some of his emotional responses in an attempt to make Chess homicidal when he encountered Ren'dorei. The shadow priestess had not been subtle; she had not expected no Chess to survive for long beyond his use as her killing tool.

Fortunately, she had not had a chance to finish her job. Unfortunately, her psychic surgery had left Chess plagued with images and flashbacks whose horrific content precluded sleep. It was only by accident that Chess had stumbled across the fortune teller Sayge at the Darkmoon Faire, and ended up seeking guidance from the Shrine at Aviana.

At the Shrine of Aviana he could sleep.

During his torture, Jon had also been addicted to Sa'Diablo, a narcotic hallucinogen with healing effects; since the alternative was looking like a human Wretched, Jon had obtained a supply and kept himself awake with the doses he had to take to keep the harmful symptoms of the Fel addiction at bay. Every few days, he found himself compelled to travel to the Shrine of Aviana, so that he could sleep deeply, and recharge in some small part the reserves called upon by the Sa'Diablo.

If he was fortunate, he would not dream. This night, his dreams manifested in the form of a memory.

Jaina Proudmoore, when she had established Theramore, had appealed to the former head of the Alliance intelligence service, now retired as a modest seller of cheese in the city of Stormwind, and asked him for assistance.

"Master Trias, Theramore is young and must survive. it could become the cornerstone of peace between the Horde and the Alliance. I need your help!" she had begged.

Her pleas had not fallen on deaf ears. Trias had recently found a fellow who he had sent to Ravenholdt for training; Ellng Trias was not quite so retired as he would have the world believe. When that student returned from his training with Ravenholdt, Trias sent him to help Lady Proudmoore.

Lady Proudmoore had established her fledgling intelligence service under Captain Kestralil, head of the merchant company *Universal Exports*, based on her ship Blackblade, docked in the Theramore harbor. Jon traveled to Theramore, where he reported to Captain Carran Vimes, the commander of Theramore's military forces. "The guards of Theramore are the finest group of Alliance soldiers based in Kalimdor. It is our duty to uphold the laws of the Alliance even so far away from our homes," he had said to Chess when Chess has reported for duty. "They are Lady Jaina's strong Right Hand of the Light - but that will not always serve. I am going to send you to Captain Kestral, who handles some of the more... nefarious issues to be dealt with. You might say she is Lady Jaina's Left Hand of Darkness."

He had taken a letter of introduction to Captain Kestral and gone to where the Blackblade was berthed. He started up the gangway but was stopped by what appeared to be a Black Iron dwarf, festooned with weapons and what appeared to be grenades and other explosive devices.

"Ye don't hae permission to come on board!" she objected.

Jon Chess tossed the dwarf a salute and presented his letter from Captain Vimes. "I'm the new crew member, darling lady."

"Ach, that is no way to greet someone. Lazy sod of a human. Well, stay right there, and I'll see what is to be done." The dwarven lady called out. "Hey Dalrick, come watch this fellow for me, I have to ask the Captain."

"Happy to, Gloriarn" responded a rather shift looking gnome, with flaming, unruly red hair under a flamboyant, jaunty hat with a purple feather. A thin, long mustache stuck out from his upper lip like a

rat's whiskers. He wore dark leathers of the type favored by SI:7 operatives.

"Are you a member of the crew, too?" asked Chess.

"Nah, just making a delivery f some medical supplies!" exclaimed the gnome. "But I'm an old 'friend of the family', so to speak." The gnome extended a gloved hand. "Dalrick Cogspinner, at your service."

"Pleased to meet you, Master Cogspinner," replied Chess.

Gloriarn returned. "Thanks, Dal," she said, dismissing him. She turned to address Chess. "You there, Captain Kestral will see you in her quarters."

"Excellent... uh.. where are her quarters?" Chess replied bashfully.

"Ugggh... landlubbers!" the dwarf exclaimed in mild disgust. "Dal, can you show him?"

Chess followed the gnome down a stairway and to the door to the Captain's quarters. Dalrick knocked on the door and whispered "You wait for an answer. Never knock twice..." and disappeared back to the top deck.

"Come," came a shout in replay to the knock. The voice was deep and husky, and all woman.

Chess opened the door and stepped into Captain Kestral's quarters.

Like most shipboard cabins, the Captain's cabin made a science of the economy of space.

"Welcome to the Blackblade, Master Chess," began Captain Kestral, turning her desk chair away from her desk, where she had been working on ledger entries. "This says you were recommended by Elling Trias,and trained in Ravenholdt; good enough for the secret side of what *Universal Exports* does, but as for the rest... have you ever been part of a ship's crew before?"

Chess took a very brief second to appreciate the attributes of the woman before him. She stood a few inches shorter than Chess but was slender but strong as a willow sapling. Her black hair tumbled away from her face in shoulder-length dark waves. Her skin, once fair, was deeply tanned by her life aboard ship. Her breasts were the size of large apples, set high on her chest, and tightly restrained undershirt and leather vest. She had a red sash around her hips, which flared out gently from her waist and tapered into thigh-high leather boots. Her forearms were covered in stiff leather vambraces, and Jon noted the throwing knives sheathed in the undersides. A heavy weapons belt was hung around the end of her chair, supporting two scabbarded daggers as long as her forearms.

"No, Captain, I have not. The boat from Menethil Harbor was my first time on the big water," said Chess. "I spent the whole trip at the rail; apparently I am not a good traveler."

"That's too bad... well, I have to find a job for you if you're going to be part of the crew..." Kestral said thoughtfully. She looked at his thickly-muscled body, clad in right leather armor. "I know... you can be my Cabin Boy"

"What does a Cabin Boy do?" asked Chess suspiciously.

"The Cabin Boy is the Captain's personal servant," she said, grinning mischievously. "Your duties would include whatever I say they are, really... sounds ideal as a cover for your other duties. And it will give you time to learn something about how the ship operates, just in case you might actually be needed to function as part of the ship's crew."

She gave him an amused look.

"You didn't think this was all just for show, now did you? Until Jaina asked me to come into the service of Theramore, the Blackblade has been a nimble little shark in whatever waters the Kul Tiras crown needed information, but *Universal Exports* is a legitimate trading company, with cargoes and inventories. We just happen to go places that Jaina finds convenient, where we listen at keyholes and expedite a positive change in a surreptitious manner. It would be useful if you knew your way around a ship, though - we don't have crew berths for your kind of specialist."

"Very well, Captain. I guess you have yurself a new Cabin Boy"

Several weeks passed, as Chess settled into his new berth. His duties often kept him out of Theramore, as Theramore had yet to build much of an espionage infrastructure. It was not until over a month later than Jonathan actually spent the night aboard the ship. he had ridden through the main gate from the swamp road, had his evening meal at the inn before seeking the ship and his berth.

"Welcome back, Mister Chess" greeted Gloriarn, who led the night watch because of her superior night vision. "The Captain left standing orders for you to come see her when you got back."

Jon ducked below decks and made his way to Captain Kestral's cabin, knocking softly; if she was asleep, Jon judged that whatever she wanted to see him about could wait until morning.

"Come" he heard her reply through the door.

"Chess reporting for duty as ordered, ma'am," he announced as he stepped through and closed the door behind him. "How may I be of service?"

Captain Kestral turned from where she had been seated, reviewing maps and navigational charts. "Two things, Mr. Chess. Forst of all, we are heading to Stormwind in two days time, and I wanted to know if you would be joining us?" She peered up at him from under her cascade of hair, and Jon was struck anew at how attracted he was to his Captain.

Jonathan smiled. "A trip to Stormwind suits me very well, Captain. I can check for correspondence, arrange for some shipments for Kalimbor from Trias' Cheese, and coordinate with SI:7 while we're there."

"Excellent," she said. The tone of her voice changed to a more teasing kind. "The other thing I wanted to discuss is the shameful neglect of your duties as my Cabin Boy..."

Chess looked a little nonplussed. "Ah... I apologize, my lady Captain. I am afraid my other duties..."

"Yes, yes," she said, interrupting him. "Still, a Captain sometimes needs to relax, and a Cabin Boy can be an important part of her regimen!"

"I see... well, honestly, I have no idea what you are talking about, but I will obey your every command, my Captain!" replied Chess. He wasn't sure what game Captain Kestral was playing, but he was game.

"I am pleased with your eagerness, Cabin Boy!" enthused Captain Kestral. "Although, when it is just the two of us, please call me Kestral, or simply 'Kes'. There's no need to be strictly formal, is there?"

"As you wish, Captain Kestral," he said, deliberately using her title with a grin.

"Very good, Mr. Chess... or may I call you Jon?" she asked, but then answered herself. "No, not 'Jon' - that doesn't work for me. How about 'Jonny'?" Chess nodded.

"Very well. Cabin Boy, your Captain is thirsty. Please fetch a bottle of Dalaran Noir from the galley."

"Aye aye, Captain Kestral!" he said, returning shortly with the requested wine and a pewter tankard. He poured her a good measure and handed her the vessel.

Captain Kestral nodded her thanks. She moved over to her bed, and ssat down.

"Cabin Boy, come help your Captain take her boots off," she commanded.

"Aye Aye Captain!" Chess responded enthusiastically. He moved to the side of the bed, and took one booted foot in hand, firmly pulling on the heel of the thigh-high leather boots. Once both boots had been removed, Chess put them neatly together on the floor at the foot of the bed.

"Well done, Cabin Boy!" purred Kestral. "Now... rub your Captain's sore feet."

Grinning, Chess popped of a quick two-fingered saluted. "Aye aye Captain!" Chess took a small vial of refined, oderless Fish Oil from his lockpick set, which was usually used to to deal with rusty hinges or lock mechanisms, and coated his hands, letting his body heat warm the cold oil. Taking Captain Kestral's left foot, he began to massage her sore muscles, focusing on the archway, then the balls of her feet. After a while, Jon switched to the right foot.

Captain Kestral moaned her appreciation, and after a moment got to her feet. She unbuckled her belt, and slowly, shifting her hips sensuously, shimmied out of her tight leather trousers. Clad in only a pair of soft mageweave panties, she lay back on the bed. Jon felt his mouth grow dry as he appreciated her long, muscular legs.

"Cabin Boy... my knees hurt!"

"Aye aye, Captain!" Jon worked his way up her legs, rubbing first the left then the right calves, slowly proceeding to her knees. Kestral's muscles were well-toned. Gently, Jon massaged the supporting and connecting muscles around the joint.

"Mmmmm..." Kestral said. "Well done, Mr. Chess... now, there's something else your Captain would like you to rub..." Reaching down, Kestral moved her soft mageweave panties to the side, spreading her legs slightly.

"May I obey all of your commands with enthusiasm, Captain!" Chess said as took his place between her legs. She shuddered as his hot breath played over her pubic mound. Kestral's thatch of pubic hair was thick and black, but well-trimmed; she would later add keeping her mound trim and shapely to Chess's duties as her Cabin Boy.

For now, he was content to exhaustively explore Kestral's cunt. Using his fingers, he drew parallel lines down alongside her labia. her scent filled his nostrils, making his erection even more pronounced. She was visibly lubricated, with her slit glistening with signs of her arousal.

Chess played and teased, staying away from her clit. He brushed his fingers lightly along her labia, teasing her opening. When she started moving to capture more of his finger, he slowly began delving deeper.

"Yess... oh Jonny, that feels so good... I want more... please?" All semblance of Captain and Cabin Boy fell by the wayside there was only Kestral and Jonny now, and Kestral was in need. Jon added a second finger along the first, stretching her cunt, which gripped his fingers tightly, like a drowning person's hand on a lifeline. Jon increased the pace of his fingers, thrusting in and out in time to her increased movements. Without being bid, Jon leaned forward and kissed her clitoris, taking the erect silken pearl between his lips and applying suction as he worshipped her with his tongue.

it did not take long before kestral's pleasure crested, and Jon experienced his Captain's first orgasm with him. As her spasmssubsided, Jon relented, kissng and using his tongue gently. When she ahd recoverd, she spoke.

"Cabin Boy, you have done your dut beyond expectation. you are dismissed. Jon smiled a huge grin, and got to his feet. His mouth and hands were covered in her sweet honey. before he could turn to go, she added, in a low, sultry, pleading voice:

"The Cabin Boy is dismissed,... but Jonny, I would really like it if you would stay the night with me...?"

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