The Futa Captain

This is a long story and there are sections of exposition that you can skip if desired. All characters are fictional and over the age of 18. Enjoy!

--

Yslinda was enjoying a mug of ale at the Bawdry Tavern while her ship was being loaded with a shipment of fine wines to the port city of Maior. She and her crew had a few days of shore leave before taking off on the two week journey. Already one of her crew had resigned and she had posted a sign for a deckhand.

She had just filled the spot with a strong young woman who had served in the navy and was now pleased that she could relax before shipping off in a few days.

"Excuse me, ma'am," a soft voice interrupted her reverie. A young man stood before her with his cap in his hand. He was tall and thin, pale skin and lanky brown hair. "I wanted to apply for the deckhand position."

Even if the position hadn't been filled, this boy didn't look like he could lift a rigging if his life depended on it. "Sorry, kid. The position has been filled."

He started to turn and seemed to steel his nerves. "I'm sorry to bother you, but..." He swallowed hard and then continued, "You wouldn't be needing a cabin boy, would you?"

She looked at him hard again -- he wasn't unattractive, with soft lips and bright eyes. He was lean and unkempt in a way that suggested he probably didn't have much. "You realize I'm called the 'Futa Captain'?"

He met her eyes shyly, "Yes ma'am."

She considered for a few minutes. He was likely to chicken out like every other man she'd ever met. But what the hell, it was worth the chance.

"What's your name, boy?"

"Simon, ma'am."

She flipped him a gold coin. "Take this and get a haircut and a bath, some clean clothes. Meet me on the north dock at the second rooster tomorrow and I'll consider it."

He gave her a broad smile. "Thank you! I will see you in the morning, captain!" He rushed off and exited the bar through the crowd of sailors.

Yslinda shrugged and figured that she had just lost a gold coin. She would just consider it charity since it was unlikely she'd ever see the boy again.

--

The next morning Yslinda enjoyed a leisurely walk down the pier to the north dock. The sun was just rising and it would the last time she would enjoy solid ground for a few weeks. To her surprise, Simon was waiting as instructed at the dock. He had bathed and had his hair cut. He was wearing a clean linen shirt and pants with a simple leather belt. He had a small bag at his feet that contained a few changes of clothes and some toiletries.

"Good morning, captain," he said with his quiet voice. He could barely look her in the eyes and his face was flushed.

"I must say I'm surprised to see you," she said. As she appraised him again, she was pleasantly surprised how nicely he had cleaned up.

"Before we go any further, I just want to confirm that you understand what you are getting into. You will be my personal valet, clean my cabin, wash my clothes, serve my meals and keep everything in order. When you are in my cabin, you will be completely naked at all times and service me whenever I want. I'm a demanding master."

Yslinda expected him to bolt at that point. Cabin boys and girls could make good coin, but it was essentially a sexual servant to the captain.

Simon nodded his head and said, "Yes, captain. I accept if you'll have me."

With a fair amount of surprise, she said, "Pay is one gold a week. Our next port is Maior so you'd be stuck for two weeks. Can't really change your mind."

"I understand, ma'am. I'm ready to go."

"Very well, let's get on the ship."

Simon tried to hand her the change from his gold coin. She looked at him with surprise, "You keep the change."

She led him down the dock and up the gang pank to her ship, The Futa's Wave. Yslinda was a little taller than average for a woman. She was in her mid-twenties -- a huge success for someone her age. She had shoulder length blonde hair that shone in the sunlight. She was fit and strong from her years of sailing.

Her crew was busy preparing for the journey but when she stepped on the deck, everyone stopped at turned to her. "Good day, crew! We set sail as soon as I've inspected the cargo. Before we go, I want to introduce my new cabin boy, Simon."

The crew nodded and gave a few winks before getting back to work.

Yslinda led Simon to her cabin on the stern. It was a spacious room with a double bed, a sturdy table for work and dining and other fine wooden furniture. There was even a small bath that could be filled with hot water. Three port holes looked out at the ocean and provided fresh air.

"You can put your things in the bottom drawer. I'm going to inspect the cargo and get the ship sailing. I won't be back until dinner. The kitchen is below deck, introduce yourself to the cook and have my dinner ready at 6."

"Yes, ma'am!" Simon said sharply.

Yslinda didn't have high expectations but closed the door behind her and left to do her duties.

--

It was well past six before Yslinda was finished with her duties. She was hot and tired and had nearly forgotten about Simon. She just wanted a quick bath and meal.

She opened the door and a fresh salty breeze wafted past her. Her meal was sitting on the table with a lit candle. A glass of red wine was poured by her plate. Her bath was lightly steaming. Every surface was scrubbed clean and her bed was made up. To her surprise, Simon was naked standing in front of the bath. He nearly gleamed in the dimming light with his pale, lean frame. He was shaved from the neck down, every bit of hair removed. His average cock twitched as she stared at him. He had fat, heavy balls that hung lower than his cock. Most surprising was his firm, round ass -- much thicker than she would have expected on such a skinny boy.

"Well done," she said honestly. He came over meekly and asked, "Would you like me to help you in the bath?"

She nodded and allowed him to undress her. He removed her boots and jacket, then her fine shirt and pantaloons, he freed her ample breasts from her wraps and then very tenatively pulled down her briefs. Her big cock nearly slapped him in the face as it flopped free. Even just a little hard, it was intimidating.

She stepped into the bath and allowed herself to soak in the warm water. Simon busied himself putting away her things and getting her bedclothes. He brought over a wash cloth and scrubbed her back and arms. He brought over a large towel when she was ready to get out. He then handed her the bedclothes and helped her dress.

At this point, Yslinda was starving and horny. Watching his firm ass and huge balls swinging had brought her blood to a boil. She sat down at the table and instructed him to sit across from her. They ate their meal in relative silence. He asked her a few questions about her day but they both focused on eating.

Simon gathered the dishes and placed them in the small wooden crate by the door. He bent over exposing his backside to her, sending a rush of blood to her swollen cock. When he turned around and saw that she was hard -- nearly 10 inches of thick woman dick pointed right at him -- he went over to the nightstand and pulled out the bottom of oil.

"Would you like me to service you now?" He asked timidly.

Yslinda could only nod. His long fingers rubbed a generous coating of oil on her fat shaft. He pulled back her foreskin gently and applied more oil to her bubous cock head. A few more mintues and she would have shot a load across the room. He then used his oiled fingers to lube up his asshole and then leaned over the bed to present his pink asshole to her.

She couldn't wait another moment. Afraid that she might tear him in two, she tenatively pushed against his sphincter. After a few moments of pressure, her cockhead popped into his ass and he let out a little squeal. He continued to push himself back onto her massive dick, swallowing her to the base. He let out little moans as she pulled herself slowly back and then forward again.

His ass was incredibly tight but willing and she soon was able to thrust a little harder. He braced himself and positioned his thick ass to give her maximum leverage. Her huge cock felt every ridge of his ass as she pushed in and out. His meek and horny cries of pleasure just amplified her desire and she began to fuck him in earnest.

Yslinda quickly felt herself peaking and thrust deep and hard before an eruption of cum shot from her dick. She came for minutes, dumping load after load into his tight ass.

When she was finished, she slowly removed her softening dick from his gaping butthole. And stood back to admire her prize.

Simon turned around his own smaller dick still hard and leaking. On the floor she saw a large stain where she had fucked the cum right out of his dick. Simon quickly set to cleaning up her, himself and the floor.

Yslinda crashed onto the bed in exhaustion and fell asleep almost immediately. For the first time in years, she was completely satisfied.

--

Yslinda was having the most amazing dream. To the gently swaying waves, she felt her nipples being sucked and licked gently, while her cock head was being softly rubbed. As she woke up, she realized that she wasn't dreaming. Simon had pulled up her bedclothes and was suckling at her tits and using an oiled hand to stroke her dick. She leaned back and moaned in pleasure, he was taking a slow, leisurely pace to make sure that she built up a huge orgasm.

His long finger were wrapped around her fat cock head, rolling in a circular motion for a while, and then changing to a slow up and down motion. His tongue and lips meanwhile went from nipple to nipple, teasing them with slippery saliva.

Her orgasm built slowly, his constantly changing pace and techniques, slower and more pressured as he went. As she was near to bursting, he took two fingers and rubbed them along her frenulum. She was too far gone at this point and her cock began to pulse and throb as a huge load shot out. He didn't speed up or change position as thick strands of cum splashed her chest, stomach and his face.

Once she had completely stopped, Simon quickly got up and began to clean up. He was naked as she had instructed, his cock hard and red. His dick was average sized, about six inches and decently thick. "Are you going to take care of that," she asked him with humor.

"Oh no, ma'am. I promise not to touch myself without your permission."

She had forgotten that was a supposed tenant of the cabin boy rules, but she didn't think that anyone would actually follow them.

Her boot were gleaming in next to her pressed and cleaned clothes. A small breakfast was waiting at the table. He had somehow snuck out and managed to take care of everything. She could definitely get used to this.

---

She was finished early today and thought that she might catch Simon unprepared. The whole day she had thought about his ass, lips and fingers. It might be good to take him down a notch.

She quietly entered her cabin a few hours before he would be expecting her. He was on his hands and knees scrubbing the floor. His naked ass exposed for her to see with his big balls hanging low between his legs.

He stopped what he was doing. "Wecome back, captain. Would you like me to fetch you dinner?"

"No, it's too early. I was just checking on you."

"Thank you, ma'am. Would you like me to service you?"

"Uh, all right, that would be nice."

In a flash, he removed all of her clothes and oiled her cock -- nearly as thick as his wrist. After lubing his ass too, he laid down on the bed and lifted his legs so that she had easy access to his glistening butthole. She didn't waste any time lining her dick to his ass, lifting his heavy balls out of the way.

Again, it took a moment for her glans to pop into his butt, but then she was able to grind her dick into his tight hole. She was amazed at his ability to take her full girth and length. She grabbed his thin hips and began to fuck him hard and fast. Having already cum in the morning, she wasn't going to be quick.

Simon gripped the bed and let out happy lilttle squeaks as she pounded his ass. His cock slapped against his stomach and his testicles rolled around like like cannon balls. His tight asshole squeezed against her large cock, milking her from tip to base. Within moments, his dick was leaking clear fluid, smearing all over his flat, pale stomach. And then with each thrust, his prick shot a few drops of cum as she pounded his prostate.

His eyes rolled back in his head as Yslinda felt her own orgasm building. He grabbed his ankles and she slammed her enormous cock into his tight hole. Soon she cried out and her dick spasmed and shot load after load into his colon.

After a few minutes, Simon cleaned everything up, dressed and went to get their dinner. Yslinda laid back on the bed and thought that she might keep him around for a very long time.

--

The next morning, Yslinda woke to a warm, wet sucking on her cock. Naked Simon was hungrily licking and sucking her fat cock head. He couldn't get much more than the first few inches into his throat, but his enthusiasm and technique left little to be desired.

Simon worked his tongue around and around her sensitive glans and then swallowed it whole. Again and again he worked his magic, sucking gently and then harder as he brought her closer and closer to orgasm. His hands worked her thick shaft, rotating back and forth as though trying to coax the cum from her.

It didn't take long before she felt the first blast of cum. He locked onto her cock, sucking and swallowing as quickly as he could. His mouth soon overfilled and cum ran down his cheeks. When she was fully finished, he cleaned her up with his tongue and thanked her.

Her outfit was laid out on the chair as before and her breakfast was sitting on the table. Feeling slightly annoyed at how perfect he was, she commented, "I wanted to wear the black coat today."

Simon blushed and quickly said, "I'm sorry, ma'am." He rushed to cabinet and swapped the blue coat for her black one. He waited quietly by the chair and then asked, "Do you want to punish me?"

"What?" She asked in surprise.

"I disappointed you. You can punish me if you want."

Yslinda realized fairly quickly that Simon was more than a little submissive. And she had to admit that she liked it. "What should I do?"

Simon chewed on his cheek for a moment and then said, "Perhaps a spanking to ensure that I don't make assumptions in the future."

"Yes, I agree that makes a lot of sense. You serve me and should follow my instructions." She sat down on the chair and motioned for him to lay over her lap. He didn't put much weight on her, holding his thick buttocks high for her. She could feel his prick against her thigh, already hard and excited.

She decided to test him and brought her hand down hard on his right buttcheek. He let out a muffled cry but didn't protest. He spanked him again counting out five hard blows on each cheek. His pale buttocks were bright red and she could see her hand prints.

As he disentangled, he said through gritted teeth, "Thank you, ma'am. I'll try not to make mistakes in the future."

Yslinda got dressed and headed out for her day. Simon was an absolute revelation to her -- horny, submissive, and dirty. She couldn't wait for her day to end so that she could fuck him in the ass again.

--

Unfortunately, her day was long and hard -- the seas were rough and her constant attention was needed to bypass a big storm. She arrived in her cabin sweaty and tired. Simon was refreshing her bath with warm water, leaning his thin body over the tub so that his meaty balls were clearly visible to her. She felt a little rise in her briefs at the sight of his ass.

He helped her into the tub and then spent the next thirty minutes massaging her shoulders, arms, legs and feet. She hadn't felt so relaxed and pampered in her life. He helped her into her bed clothes and then made sure that she ate and drank. When she was finished, she laid down on the bed nearly ready to sleep.

Simon came over and asked, "I see that you are very tired, captain, but would you like me to service you?"

"I may be too tired tonight."

"I'll do all of the work, ma'am. Just lie back."

Simon got the bottle of oil and pulled her bedclothes back. He stroked her fat cock, generously lubing her up and stimulating her sensitive glans. After oiling his backside, he got on the bed and positioned himself above her. He lowered himself down and squatted onto her bulbous cock head. He pushed himself onto her and then lowered himself until his smooth balls and ass were her touching her stomach.

He leaned foward a little bit and then rocked himself back and forth slowly and carefully to fully pleasure her dick. His tight ass squeezed and swelled to let her feel every inch. Over time he went faster and harder, slamming his thick ass onto her dick.

His smaller prick was now spurting drops of thick white cum every time he bottomed out on her dick. Soon she felt her dick burst -- shooting ropes of cum into his ass as he milked every drop from her massive dong. As always he cleaned everything up and found her fast asleep. He blew out the candle and then snuggled next to his mistress.

--

Yslinda woke to her hard dick being given the most amazing head treatment. When she opened her eyes, she saw Simon's naked ass popping on and off of her cock head. It stretched his tiny sphincter with each push and then eased out leaving a small gape. He just worked the tip in and out of his asshole. He seemed to be enjoying it too but it wasn't deep enough to make him cum.

Out of instinct, she reached out and pinched down on both of his soft nipples. They immediately hardened and he let out a moan. "You like that?" She asked him.

"Yes, ma'am!" As he picked up the pace on her cock head, massaging the tip of her fat dick with his asshole. She twisted and pinched them as he increased the pace.

Soon she felt a rush and he pushed her fully up his ass. She let out a satisfied cry as she pumped him full of her thick cum. He gently rocked back and forth to milk every drop from her fat dick.

He cleaned everything up while she ate her breakfast. When she went to get dressed, she noticed that her boots were missing. "Where are my boots?"

"Oh sorry, ma'am." And he scurried over to the cabinet to retrieve them. He helped her put them on. With his head bowed, "I suppose you'll have to punish me again."

She sat down and said, "Over my lap and spread your legs wide." He did as she instructed, leaving his well-used asshole exposed to the air. She brought her hand down hard on his left buttock and then his right until both were bright red, then she more lightly slapped the crack of his ass and balls. He flinched and moaned but stayed in place. When she was finished his entire backside and ball sack were a nice shade of pink.

"You will need to be more diligent in the future."

"Yes, ma'am! Thank you, ma'am."

Yslinda left him standing in the room, his dick hard with a small drop of pre-cum dripping from the end.

--

For the next two weeks, she used his hands, mouth and ass as her playthings. He routinely made small mistakes in the morning and evening so that he could be properly punished. He particularly liked when she slapped his dick for spilling wine on her tablecloth.

The night before they reached the port city of Maior, Yslinda asked him, "You seem to enjoy being my cabin boy. Will you be staying on?"

"Yes, ma'am. It is the best job in the world."

"While I'm in port, I'm going to pick up some additional things to keep you in line."

"I would like that very much, captain. Thank you!"

"Very good," she said. "And now you can service me."

After lubing up, Simon got on his hands and knees and pushed his ass in the air for Yslinda to easily fuck. She was in the mood for a rough fucking, so she wasted no time in plunging her massive cock into his tight ass and pounding him. Her thighs slapped against his ample butt and she could feel his heavy balls swinging against her legs.