The Futa Captain

Simon kept his ass proud and high so that she could fuck him deeply. He began cumming quickly, each push leaving a small trail of cum hanging from his hard cock. She grabbed his hips and begain rapidly pumping in and out of his sensitive ass. He moaned and cried out as she abused his butthole.

Finally she began to cum ropes of thick cum into the depths of his bowels, leaving him feeling full and used. She patted him on the ass as he went about cleaning up. "We're just getting started, boy. We're just getting started."

--

Yslinda was busy for the few days that they were in port. She had to arrange the delivery of her cargo and then coordinate the next shipment. She visited the bank and managed deposits and payments to various vendors. She had to restock the ship for another two week journey. She also visited a small shop in the red light district and ordered a few custom items.

For years she had been working towards the purchase of a larger ship so that she could take on bigger jobs and make more money. With this last shipment, she was able to make the final payment on her custom galleon that was waiting in the next port. It seemed like everything was going her way -- business was booming, her new ship was finished and she had the cabin boy of her dreams.

The Futa's Wave took off a few days later after filling the hold with fine goods from Maior. Before they launched, Yslinda made a short speech to the crew and informed them that their new ship would be waiting. She promised a better galley, more space for the crew and most importantly more pay. The crew cheered and set off to the rising sun.

When Yslinda got to her quarters, Simon was waiting patiently, naked as always. He had taken care of her room while she had been out and everything was clean and organized. During the shore leave, he had gotten a haircut and spent a few silver to buy a pair of leather sandals.

She had been encouraging him to get more exercise and fresh air. His face and arms were bronzed by the sun contrasting with his pale torso and legs. His scrumptous ass was still as pale and inviting as ever. Three days without fucking had seemed the longest of her life.

"Congratulations on your new ship, ma'am! You are a great captain. I am proud to serve under you."

"Thank you. The new captain's quarters will be much larger too. I will have a state room in the front for dining and work and a bedroom in the back with a larger bed and more space."

"I will be spoiled, ma'am. I hope that you will keep me as your cabin boy even when you are more famous."

"You aren't going anywhere, young man."

Simon got a tear in his eye but quickly composed himself. "I took the liberty of running a bath for you. And a light dinner is ready on the table." He paused for a moment, "Um, but I haven't poured you a glass of wine, I apologize. Would you like one?"

"Yes, of course, you silly boy."

Simon quickly turned and headed to the wine cabinet. She suspected that he leaned over provacitively and exposed his tight pink anus just to arouse her. He came back with a nice bottle of red wine and poured her a glass.

"I suppose that I'll have to punish you before my bath," she said as she sipped her wine. Simon nodded in agreement.

She placed a small wooden box on the table. "While I was out, I managed to procure a few tools of punishment. I'm not going to share them all with you now, but I think that I'll start with this..."

She opened the box and pulled out two silver clamps and a small bag of weights. "Come here," she instructed. She licked her fingers and then pinched down on his left nipple, twisting and flicking it until it was hard. She then took a clamp and screwed it on until his hard nipple was firmly captured. Simon's hard cock was at full attention and he was trying to stifle his moans of excitement. She repeated the process with his right nipple and admired her work.

"We'll start off with the lightest weight today, but eventually we'll work our way up until your nipples are as big as a girls."

"Oh, yes ma'am!" He exclaimed. She placed two small balls at the end of each clamp and then gently pulled down on his already sensitive chest. He moaned again at the extra sensation.

"My bath now..." Simon got up and helped her undress. She gave his clamps a little tug every so often if she felt he wasn't moving fast enough. Simon's dick already had a little tear at the end from his stimulation.

Yslinda's cock was already hard as a rock but she wanted to take her time. She took a leisurely bath and enjoyed her wine. She also ate her dinner slowly and regaled Simon with stories of the sea.

When everything was cleaned up, Simon asked pleadingly, "May I service you, ma'am?"

"Yes, you may. Do you want me to take off the clamps?"

Simon gulped but said quickly, "No, ma'am, I don't think I've been punished enough."

He got the refilled bottle of oil and generously lubed up her fat, swollen cock. Three days of saved up cum were waiting for him. He then used his oiled fingers to lube up his butthole and he got on his hands and knees for her.

Ylsinda didn't waste any time. She plunged her huge cock into his tight asshole in one stroke. Simon let out a cry of pleasure as her cockhead raked his bloated prostate. Yslinda took out of all of her sexual energy on his clenching ass, thrusting in and out with her full length. Simon was biting into the pillow to keep from making too much noise. He raised his ass and lowered onto his arms so that she could fuck him as hard as possible.

She grabbed his thin hips and pounded him. His little nipple weights swung with each blow and pulled on his throbbing nipples. Within minutes, he was shooting ropes as she milked the cum from his ass. She tried to hold her own orgasm as long as possibile, but soon she felt the inevitable surge.

With a few final powerful thrusts, she let out a cry and felt the first blast from her cock. She filled his asshole with a huge load, cumming for what seemed like an eternity. It took him a few minutes to recover and start to clean up. Yslinda removed his nipple clamps and gave each of his tender nubs a final pinch.

They cuddled up in bed and fell asleep quickly.

--

The next morning, Ylsinda woke to the wonderful sensation of his mouth on her cock. Over the past few weeks, he had managed to get more and more down his throat. He was nearly half way down her shaft and pushing further. He pulled off and asked, "Ma'am, I wondered if you would like me to touch you 'down there'," pointing to her pussy.

Yslinda had the working sexual anatomy of both a man and woman. For her whole life, her dick had been her primary focus, but she did enjoy having her vagina played with. "Yes, you may," she said, frustrated that he had stopped.

Sensing her urgency, Simon immediately tried to swallow as much of her dick as possible, letting her bulbous head bruise his throat. His fingers gently rubbed her wet pussy and stroked her sensitive lips. His index finger slipped in her pussy and she gave a small thrust, pushing her dick another inch into his mouth.

He held fast and continued to bob up and down on her dick while his finger gently massaged her cunt. He found her equivilent of a prostate and his finger began to rub circles around it. Yslinda's eyes rolled back into her head and she began to almost immediately cum down his throat. She used his throat as a pussy, pumping her dick as it spewed a huge load straight into his gut. Simon fought every survival instinct and let her use him.

When she was finished, he licked her clean and removed his finger. He had a slightly satisified look on his face as though he had unlocked a treasure. Yslinda had to admit that she was very happy he had.

Simon got her dressed and let her eat her breakfast. His dick was still hard as she finished up. She wished she could just spend the day in bed, fucking his ass and face. But she didn't even have time for a punishment. "I'll see you this evening, Simon," she said as she exited the room. "Don't forget to exercise and get fresh air. We want you in top shape."

"Yes, ma'am! Thank you," he said with excitement.

--

Yslinda had found that making the punishments random kept Simon on edge and aroused in a way that she liked. She had brought out the nipple clamps a few times and had already tried the next heavier weight. She had been exciting planning her next move for that night.

Simon was naked in the room, setting up her dinner when she arrived. As always he seemed to be exposing himself to her lewdly in an effort to arouse her. Not that she minded.

"Good evening, ma'am," he said bringing her a glass of white wine that would pair well with her fish dinner.

"Thank you," she said. "I'll take my bath now."

He helped her undress and then enter the bath. She sat back and gave a disappointing look. "It's not very warm. You must have run it too early."

"You are right, ma'am. I apologize."

"Bring me the box next to the nightstand," she instructed. She opened it out of his view and pulled out a silver device that looked like a cuff. She then closed the box and had him put it back.

"Come here," she said. "Lift your dick up and show me your balls." He did as he was instructed. His balls were impressively large as though always bulging with cum. She started by removing a small pin and unlatching the opening. She put it around his ball sack and then closed the latch and replaced the pin. She let go of the device and Simon felt his balls be pulled down even further by the weight. The cuff was nearly three inches long and it stretched his testicles so that they were tight against his skin.

The sensation made him moan as the pressure sent waves of pain and pleasure through his torso.

Yslinda went back to her bath and enjoyed watching him try to walk around with his balls pulled down.

She told him to stand during dinner so that he could enjoy the full effect of the ball clamp. When they were finished with dinner, Yslinda was ready to fuck in earnest.

She had Simon lean over the table and spread his legs wide so that she could really feel the effect of his weighted down balls. She fucked him shallowly at first, making his fat balls swing back and forth. Simon was already biting his hand to keep from crying out in pleasure. She continued to fuck him deeper and harder until she could feel his stretched balls against her pussy.

Simon pushed back to take every inch of her massive dong. It felt like she was fucking him to his stomach. The ball clamp made it harder to cum and he could feel the pressure building and building. Yslinda sensing his frustration redoubled her efforts and aimed her cock straight at his swollen prostate.

Letting out a cry, Simon's cock erupted in a blast of thick cum, each thrust of her dick draining more and more from his constrained balls.

Feeling his ass clench and his writhing hips, she let her own orgasm explode. She used his ass as her personal cum dump and wrung load after load deep into his bowels. She finally finished and leaned onto his sweaty back.

After a few minutes, Simon extracted himself and began the clean-up process. After everything was clean and Yslinda was in her bedclothes, she removed the heavy ball cuff. He let out a small sigh of relief as his balls retracted a bit, but he couldn't wait to try them again.

--

Yslinda had switched between nipple clamps and the testicle cuffs every few days, and the day before had used both on him as an experiment. She was now excited to unveil the last surprise.

She had been awoken to his mouth clamped to her hard nipple, one hand stroking her cock and the other fingering her pussy. He enjoyed taking his time, sucking one nipple and then the other. His hand rolled over her fat cockhead as if polishing a knob. His fingers probed and teased her pussy just enough to build pleasure but not enough to make her cum.

Her cock was long and smooth with a generous foreskin to roll over her fat head. It was thick from the head to the shaft, getting slightly thicker at the base. She had a small mound of blonde pubic hair that she let Simon trim regularly. Futas have very little if any pubic hair and hers was particularly fine and delicate.

She laid back and enjoyed his ministrations, slowing building in intensity as he slowed down and focused on her most sensitive parts. She arched her back and he fully committed. His fingers pressed her g spot, his mouth fully sucked her right nipple and his hand vigorously stroked her dick. A thick rope of cum shot from her cock and then another and another until they were both covered in her sticky goo.

Simon cleaned up and helped her dress. They ate breakfast to the sounds of the ocean against the hull.

"My tea was not very hot this morning," she complained.

Without protest, Simon said, "Sorry ma'am, I took too long in pleasuring you this morning."

"Bring me the box," she commanded. With a bounce in his step, he brought the box to the table. Yslinda pulled out the last punishment. It was a silver butt plug, as thick at the base as her own cock, and flared at the tip so that it would not really stimulate his prostate. She put a generous amount of oil on it and then told Simon to bend over.

She inspected his rosy butthole, still tight as the first day she'd fucked him. She pressed the buttplug against his sphincter and he let out a little moan. She twisted in back and forth, slowly stretching him out and then starting again. At the very end, it popped into place, held tight by the base.

"You'll wear this all day, doing your chores and exercises. I'll see you for an early dinner." With that, she went out and began her day.

At first, Simon enjoyed the teasing luxury of the plug, walking around and changing positions to maximize the pleasure. But as the day went on, the teasing became unbearable. His balls and cock strained from the constant teasing. By the time he had dinner and her bath ready, he was desperate for a real fucking.

Yslinda arrived around 4 - she had enjoyed watching Simon struggle with the plug in his ass all day. As she strode into the room, she could see the frantic look in his eyes. "Bend over and let me see," she instructed him.

He quickly bent over and grabbed his ankles. The base of the plug was still tight against his tormented anus. "Very good, I'll take my bath now." She wanted to tease him for a bit longer.

She got in the bath and soaked her tired limbs. After Simon had washed her with a soft washcloth, she told him to face her. She couldn't resist his puffy nipples. The nipple clamps seemed to have slightly enlarged his nipples, making them easier to tease. She pinched and twisted them until they were red and hard.

She got out of the bath and let him dry her off with a fluffy towel. His prick was hard and his foreskin wanted to pull back. His smooth balls seemed even heavier and lower than usual. Her own dick was raging hard from seeing him so aroused and frustrated all day. "Get me the oil," she commanded.

Almost tripping over himself, he brought the oil and coated her cock from the tip to the base. She had him lay on the bed and hold his ankles. She spun the plug in his ass and the pulled so that it stretched and flared. She played with him for a while as he moaned in frustration. Finally she pulled it out in one quick motion causing him to cry out. His butthole gaped open, anxious to be refilled with her fat cock.

She took her time, remembering his teasing from the morning. She poked her bulbous glans in and out of his stretched asshole and then plunged in with one push. Simon let out a cry of pleasure and his ass clamped down on her dick like a vice. She fucked him hard and deep, slamming her cock into his desperate butt. He held his ankles and spread his legs giving her the perfect angle.

Within moments cum was gushing from his dick, each thrust leaving a pool of white on his muscular belly. His ass spasmed as he orgasmed, milking her entire dick until she too was cumming. She shot a massive load of cum deep into his guts.

After a few moments to recover, Simon got up and cleaned everything up. They then ate ravenously. "Thank you, ma'am. That may the best punishment yet," he said once they got into bed.

Yslinda just chuckled and said, "You are a very naughty boy."

--

A few days before they would reach the island of Avanti and the new ship, Yslinda was admiring Simon. His tan lines were even more pronounced and his lean frame now had some musculature. He had taken her advice to heart and been working with the crew, literally learning the ropes. The last week and a half had been a delight for both of them.

He was scrubbing her boots on his hands and knees, his low hanging balls and pink anus on display for her pleasure. She would soon need to get up and manage the ship, but she was enjoying her cup of tea and watching him work.

When he was finished, he brought the boots over to her and helped her put them on. He had a serious look on his face. "Ma'am, may I speak freely?"

"Yes, of course," she said with a straight face, though she was a little concerned.

He took a deep breath and then continued, "I'm concerned that with this new bigger ship that I won't be able to fully serve you. And I wondered if I could be promoted to your personal steward and hire a cabin girl to help."

Yslinda appraised him again and could tell immediately that he was completely sincere. He had taken a great appreciation of her feminine parts and seemed to enjoy pleasuring her pussy almost as much as her dick. The thought of having two sexual servants was something that definitely turned her on.

"I will think about it," she said and then abruptly got up to leave.

That evening shortly after she had entered the room, she told Simon to sit down. "You were very impertinent today to tell me how to run my ship. But I do agree that a cabin girl might be a good addition to my staff. When we land on Avanti, you may try to hire a cabin girl at your current pay. You may earn an extra silver each week as my steward. But I'll warn you that anyone who joins must accept me as their master when they step onto the ship -- I've had cabin girls who didn't stay once they saw I was a futa."

Simon seemed outraged, "That is their loss, ma'am. I promise that we will only live to serve you."

"As it should be," Yslinda said with a grin. "Now, you must be punished, and harshly for overstepping. Bring me the box."

Simon brought over the box dutifully without being asked. "Bend over my desk," she commanded.

Obdiently he leaned over with his legs spread so that his asshole and large balls were exposed. She pulled out the buttplug and coated it with oil. She teased him for a few minutes, using the flared base to stretch his butthole obscenely.

She then took the testicle clamp out and stretched his ballsack to the limit. His balls looked like two smooth eggs straining at the bottom of the silver restraint. He was now moaning and groaning, trying to stay in place and not writhe in pain and pleasure. She now turned him around so that his dick was pointed at her chest.

Now she removed the first nipple clamp. She started by pinching his left nipple just enough to cause his knees to buckle, he let out a little cry of pleasure. She twisted it slowly back and forth until it went from puffy to hard. She then attached the silver clamp and secured it tightly. His little nub was now poking out of the metal constraint. She continued with his right nipple.

She then took the heaviest weight -- a silver tear drop a little larger than an almond. It pulled his nipples down and his dick responded with drops of pre-cum.

Again she turned him around and had him grab the edge of the table. The weight of the clamps pulled his hard nipples and stretch balls to the floor. She could see his butthole clenching against the teasing plug too.