The Futa Captain

She went around the side of him and whispered in his ear, "I'm going to give you the ultimate punishment -- only because you have pleased me, Simon."

She then raised her hand high and paddled his bottom with stinging blows. Each buttock was rewarded with 10 slaps until they were each bright red and splayed with finger and palm imprints. She spanked the crack of his ass, pushing the buttplug futher into his spasming anus. She then tapped his balls with firm slaps, sending jolts of painful pleasure up his spine.

Her own dick was raging hard and she couldn't wait any longer. She dropped her trousers and pulled out the buttplug. She immediately plunged her dick into his ass, causing him to cry out in ectasy. She used his hips as leverage and wildly slammed her fat cock deep into him. Using her full 10 inches of length, she ravaged his butthole. His weighted balls and nipple clamps swung wildly as she pounded his ass.

Simon was in a state of pure bliss, crying out each time her dick bottomed out in his tight ass. His nipples and balls were aflame with sensation as if an army of torturous fingers were assulting him. Finally, he felt his balls tighten further and a blast of semen shot from his dick, spraying all over the floor.

Yslinda sensing his orgasm, continued her assault. Cum gushed from her dick, filling his ass with what seemed like a gallon of spooge. She left her dick in for a moment as she caught her breath. She quickly replaced the buttplug when she pulled out her dick, leaving his cum-filled ass full.

"I'll have my bath and dinner now," she said with amusement.

She let him enjoy his punishment for another hour, sitting on the hard wooden chair with his reddened ass. Before bed, she fucked him again, long and slow until she and he had cum again.

"I'm not optimistic about finding a cabin girl," she admitted as they settled down for sleep. "It may take some time to find the right person, but I never imagined you either."

"I'll do my best, ma'am," he said sleepily.

"I know you will," she said with a kiss on his forehead. And then they both fell into a deep and peaceful sleep.

--

Ana Brightwell was walking down a narrow street to deliver lunch to her father, a merchant of rare books. It was sunny and bright as always but her mind was a dark cloud. She was terribly bored and had few prospects other than working at her father's shop. Her love of reading had exposed her to a world of adventure and sexuality.

Just a few years ago, she had found a secret stash of books that her father kept hidden for the afficiandos of erotica. She had stolen a thin, leather bound book called The Islands. Each small chapter was an introduction to a different type of sexual act, every deviance you could imagine was described and Ana wanted to try them all.

In the dark of her room at night, she explored herself trying to mimic the sensual acts, but her fingers couldn't replace tongues and cocks. She'd had a brief tryst with a boy named Samuel, the son of another merchant family. But he had just wanted to lift her skirts and fuck like a dog. When she'd proposed a little oral, he called her a slut and wouldn't talk to her anymore.

Ana was a petite young woman with curly red hair and a light complextion. She had small breasts and a thin boyish waist.

She rounded the corner to her father's shop and saw a poster hung on the wall, "Cabin Girl Wanted -- Futa Friendly Only! - Come to Futa's Wave at East Dock". Her mind worked furiously -- she knew exactly what a cabin girl was -- a servant to a ship's captain where your body was owned as long as you were on the boat.

She nearly missed her father's shop, but she delivered his lunch and helped around the shop for a few hours. It was incredibly boring, dusting shelves and rearranging books. There weren't even regular customers to interact with. But her mind was going a thousand miles a minute -- thinking about the cabin girl post.

"I'm going to head home, father," she called out. "See you at dinner." She heard a mumbled reply from the back and she left. She found herself walking towards the east dock. It couldn't hurt to at least look at the ship.

The Futa's Wave was moored and the gang plank was secured to the dock. A lean young man with short brown hair was busy sweeping the deck. He was handsome with a tanned face and arms, he was thin but with enough muscle to show he was healthy.

Simon noticed her staring at him and he waved, "Are you here for the cabin girl position?"

Ana was startled and she responded without thinking, "Umm, oh hello, I'm not... well, maybe."

Simon chuckled and came down the gang plank. "Would you like a tour of the ship? We'll be moving to a larger ship in a few days, but you could get a sense of what we do here." He extended his right hand and said, "I'm Simon, by the way, I'm the steward of the ship. The cabin girl would report to me -- though we all serve our beautiful captain, Yslinda."

Ana stretched out her hand and felt his warm shake, "Ana, pleased to meet you."

She followed him up the gang plank, barely hearing his descriptions of the various parts of the ship. He led her to the captain's quarters and opened the door. They went inside the cozy room.

"Now this is where I stay, when you are in the captain's quarters you must be completely naked at all times. You are also required to be clean shaven from the neck down, all hair is to be removed.

"I like to get up early and get the captain's breakfast and arrange her outfit for the day." His cheeks blushed a bit as he next told her, "And I wake her up in the morning by pleasuring her -- to ensure that she is ready for her day."

Ana couldn't help but blush too. It sounded so dirty and she already felt aroused.

"We then clean and scrub everything. For most of the day, you have time to yourself to do whatever you like. I'm learning how to sail. What do you like to do?"

It may have been the first time anyone had ever asked her that, "I like to read."

"The captain has a nice library. Though she doesn't have much time to read. For the evening, I always prepare a bath for the captain and have her dinner prepared. And then..." He began to blush again involuntarily, "I make sure and service her before bed."

"I see," Ana said thoughfully. "Every night?"

"Oh yes, every night. I am here to serve the captain." Simon took a pause as he was thinking about how much more to share. "I will be completely honest that she also punishes me if I make mistakes. It was actually my suggestion..."

Ana turned red as she was reminded of the punishment islands -- another thing that she was also eager to try. So far everything she had heard sounded wonderful -- she was already working in the house and the shop but she could also have an erotic life that only existed in her dream.

"Well, that is pretty much everything. The captain is a wonderful woman -- kind, generous and fair. But you must do everything I described and willingly. If you are at all intimidated by a futa, then you shouldn't even consider it."

Ana nodded but was too nervous to say anything. Simon led her back to the dock and again extended his hand, "I wish you well. If you are interested, we depart on the new ship in four days. The pay is one gold coin a week. Our new ship is called The Futa's Pride and is on the south dock."

He stopped again to inspect her reaction. Ana once again studied his handsome face, "I will think about it. Perhaps I will see you in four days."

"I truly hope so," Simon said with a smile. He then bounded back up the gang plank and resumed his chores happily.

Ana walked back home slowly, not really paying attention to where she was going. It all seemed so unreal but she had the flyer in her pocket and could still feel Simon's hand where they had touched.

Four days later, Ana left a note on her father's desk in the house. It explained that she had taken a position on a ship and would be gone for a long while. She was being paid and learning new skills. She would write often and thanked him for his love.

She had packed her things, including a bundle of books, and headed out to the south docks. The Futa's Pride was moored as Simon had said. It was a magnificent galleon, new and shining in the sun. A beautiful tall woman was standing on the dock admiring the ship. She had wavy blonde hair, feminine hips and large breasts.

Ana approached and Yslinda turned to her. "Good morning," she said with a warm smile. "Simon wasn't sure if you would show up. You must be Ana. My name is Captain Yslinda, welcome to the Futa's Pride."

Ana gave a small curtsy and Yslinda laughed. "So have you decided to join us?"

Ana nodded and then said with a little more conviction, "Yes, ma'am."

"And you know all of the conditions," she added. "Including me?"

"Yes, ma'am. I would like to be the cabin girl on your ship."

Yslinda looked very pleased and said, "That is wonderful. Let's get you on the ship."

Yslinda didn't give a real tour this time but she did announce loudly that they had a new cabin girl named Ana and that everyone was to be extra kind to her. She led Ana towards the stern of the ship where her new cabin resided.

She opened the door and Ana gave a little gasp. Simon was naked as the day he was born, on his hands and knees with his ass and balls completely exposed, scrubbing the floor. He turned around and said without embarrassment, "Hello, Ana. Glad you made it." He went right back to work.

Ana steeled her nerves and began to remove her garments. First she took off her slippers, and then pulled her dress over her head. She stepped out of her undergarments and, for the first time in her life, was completely naked in front of others. She had shaved her red pubic hair the night before and now felt as exposed as ever.

Yslinda nodded admiringly, "I see you are a fast learner. I've got plenty to do right now, I'll let Simon show you around."

Simon got up and now she could see his naked front too -- she couldn't help but admire his average cock (still larger than Samuel's) and his low hanging balls. She knew that she would be perpetually blushing for the next few days. Her naked body seemed to have a reaction on him as well as his prick swelled up. He smiled at her and said, "Let me give you the tour of the new quarters."

"This is the study," he showed her around the shelves of books, the long table for meals and planinng, and the various cabinets with Yslinda's possessions. They stored their belongings in a cabinet at the front door. There were two paned windows on each side to allow in light and fresh air.

He then took her to the bedroom. There was a king-sized bed with a red velvet canopy. A small marble tub stood in one corner with a private chamber pot and a few small chests and cabinets in the other. A few lanterns were hung to provide light in addition to the smaller windows in the back and side. He also walked over to the chest in front of the bed and pulled out a small box. He opened it up and showed her the nipple clamps, stretcher and butt plug. "These are some of the punishment items that Yslinda can use," he said with a whisper.

Ana wanted to reach out and try them herself, but she restrained herself. She couldn't wait to begin the journey. She figured in just a few hours she would be finally having real sex.

"What would you like me to do first, sir?" She said with confidence. Simon gave her a big smile and said, "Why don't you begin by cleaning that tub?"

--

Yslinda had a very busy day as expected running a new ship. She arrived late for dinner and was sore and tired. She decided to eat first as she was starving. They talked casually about their days and all felt a little better after some wine.

Simon and Ana got up to help Yslinda undress and get into the bath. Ana couldn't help but stare as her captain's body was finally naked. She was well-shaped with womanly hips and ample breasts. But it was her huge cock that nearly made Ana gasp -- she had never imagined anything like it and it wasn't even hard yet!

Ana and Simon both scrubbed Yslinda's skin with soft towels and sweet smelling soaps. When she emerged from the water, they dried her off and draped her new silk robe over her shoulders.

Yslinda had been planning her next move for a few hours, excited to try Ana for herself. She directed Simon to lay on the bed and then moved Ana in front of him. His hard cock was aimed at her mouth and her petite ass was pointed at Yslinda.

With curiosity and excitement, Ana recalled the island of oral sex from her book and started by generously coating his dick with saliva from her tongue. Simon let out a deep moan -- he'd never had a blow job before.

Behind her, Yslinda rubbed her swollen cock against her small, pink pussy lips. To her delight, Ana was already soaking wet and soon she was pushing gently into her womb. Yslinda took it slowly but was relieved that it wasn't her first time. It was tight in a completely different way as each inch soaked her dick in juices. She went in and out an inch at a time until her thighs were pressed against Ana's ass. She stared in amazement that this petite woman could fully take her dick.

Meanwhile, Ana was panting in pure pleasure at being filled by her captain. She was now sucking on Simon's hard cock head, spit running down his dick and balls. She took a moment to to catch her breath and licked and kissed his enormous smooth balls. Once Yslinda bottomed out in her cunt, she came, her lower extremities shaking in joy.

She went back to work on Simon's throbbing cock -- each vein in his shaft bulging. Yslinda felt her cum and began to slowly fuck her from tip to base. Ana's tight silky pussy gripped and massaged her fat cock. Ana began to press her hips back as if asking for more, so Yslinda began to fuck her a little harder.

Ana responded by cumming again and sucking even more of Simon's dick into her mouth. She now had half of his cock down her throat -- his moans growing louder and louder as his own orgasm was building.

Yslinda abandoned caution and began to pound Ana's pussy harder and harder. The sensation was so different than Simon's ass -- so wet and warm. She watched as Ana sensed Simon ready to cum and sucked down hard on his glans. He cried out and Ana greedily gulped down his sticky seed.

Yslinda felt her own orgasm build and she grabbed Ana's hip and hammered her hard. Within moments, she was shooting ropes of cum while Ana came again and again.

They all got into the large bed, one on each side of their captain, and fell into a deep sleep.

--

In the morning, Yslinda woke to her long cock being stroked from end to end and both of her nipples suckled. Simon was on one side, his right hand oiled and his mouth firmly on her chest, and Ana on the other. It was a symphony of pleasures as their hands went at different paces and techniques, one stroking while the other circled, one fast and one slow. And their insistent sucking on her nipples send waves of bliss through her body.

Her cock grew harder and harder, her nipples straining under their insistent tongues and lips. Simon and Ana kept her at bay for longer with their constantly changing movements, her dick swelling and swelling until a stream of cum erupted from her cock. White cum shot in the air and all over them all until she was empty.

They ate a hearty breakfast and then helped the captain get dressed. Before she could leave, Simon said, "Captain, I apologize that the bacon wasn't crispy as you like it."

Yslinda got a wry smile on her face. "I suppose that I have time to punish you before I leave." She sat on the chair and instructed him to lay over her knees. "Ana, hold his ankles," she instructed, curious to see how she would respond. Ana did as she was told and held his ankles, her face perfectly positioned to see the spanking.

Yslinda didn't waste time, smacking his ass, crack and balls with strong strikes. Simon tried to hold still but couldn't help but bolt a few times when his testicles were struck and his asshole was stung with a well-timed slap. After a few minutes, Simon's ass was flaming red and the captain released him,

Ana stood up with a glazed look on her face and she said quietly, "If Simon is punished, I should be too."

"I see," Yslinda said, secretly overjoyed that Ana was as perverted as them. "I'll let Simon do the honors, I need to get to work."

She left the room excited to see what the evening would bring. Simon was also thrilled that Ana was so willing a partner. It was everything he had hoped -- she was beautiful and sexy. Since he dick was already hard to the point of bursting from their sexual escapades and his spanking, he didn't think he could last if Ana was over his lap.

So he told her to grab the edges of the table. Ana's small bottom, pale and pert, was pointed jauntily at him. She had quickly moved into position, clearly eager herself.

Simon decided to start off slowly, giving her buttocks a few glancing swats to see how she'd react. When she let out a little moan, he increased the power, allowing his hand to smack against her butt. Her ass was waving back and forth from his strong blows. She even spread her legs so that he could send a few well timed swats on her smooth pussy.

They both enjoyed the morning with unspent sexual energy and rosy butts, anxious for the debaucheries of the evening.

--

There was a palpable energy that evening when they were all undressed and ready to have sex. Yslinda's massive cock was hard and swaying between her legs. "Well, Ana, since you are new, what do you propose we do tonight?"

Ana chewed her bottom lip for a moment, her cheeks were blushed with desire almost as red as her hair. "I would just like to please both of you -- anyway that I can."

"Hmm, good answer," Yslinda answered. She began giving orders, "Ana, get me the oil."

Yslinda had Ana slather her fat cock with oil. Then she made Simon get on his hands and kness, exposing his taut pink butthole and his low hanging balls. Ana massaged her oiled fingers into his anus, enjoying the feeling of his sphincter spread. She worked two fingers in and out, causing Simon to let out a delicious moan.

Finally, Ana was laid out on the bed and her legs parted wide. Her wet pussy was exhibited for everyone to see, so compact and rosy. Simon pressed his throbbing cock into her cunt, for the first time feeling a woman's intimate embrace. It was warm, velvety soft and wet. He slowly pushed his cock into her until his pubic bone was pressed against hers. Ana was breathing heavily -- his cock fit so perfectly, not as big obviously, but it fit so easily and comfortably.

Now Yslinda lined her up dick and entered through his spread ass cheeks. Simon pushed out his hips to help swallow her full girth and length. Now he too was moaning again as the dual sensations sent shockwaves through his body.

The captain wasted no time, slamming her huge cock into his pliant ass, letting the tight warm sleeve massage her dick. Each thrust slammed his smaller cock into Ana but also stimulating her little clit. Ana began cumming almost immediately, wave after wave of orgasm as her entire pussy was rocked.

Yslinda's thighs slapped against Simon's balls and ass, his narrow hips braced for impact, trying to get her deeper and harder. His prostate was on fire as she banged it back and forth with her giant cock. He found himself slamming his hips back to meet her strokes and then pushing back hard into Ana as he was fully entered.

The dual stimulation sent Simon over the edge and his ass clenched down on Yslinda's cock, spasming with a massive orgasm. His cock spilled load after load of hot cum into her pussy. Meanwhile, the captain blasted his bowels with her thick white cum.

They cuddled in bed, enjoying the post-coital bliss. They all had erotic dreams, imaging all the various combinations that they could enjoy.