Pirates of Caledonia II: Learning the Ropes
Chapter 15: The final night

Copyright© 2010 by John Salach

BDSM Sex Story: Chapter 15: The final night - John is retained as a Cabin Boy and sets sail once again with the crew of the Sedna - an all-female pirate boat. Bad weather forces them to stop at an unusual little island with a strange custom.

Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Fiction   Historical   FemaleDom   Spanking   Oral Sex   Anal Sex   Sex Toys   Water Sports   Exhibitionism  

Tara and I knocked on the Captain's door and upon being called in, two naked members of her crew burst in her office dripping wet.

She burst out laughing and got up from her bureau. Looking down at Tara's thighs that had my cum dripping down it she scraped her finger up her leg and held it out in front of Tara.

'You have been a busy boy, haven't you', she said looking at me. I nodded, cold and self-conscious. It was irrational. I was often naked in front of the Captain but this time it was so different.

The Captain put her finger upto Tara's lips, who opened her mouth for the Captain to insert. 'Lick them clean, you filthy slut. Enjoy his taste'. Tara did as she was told and the Captain guffawed. We sent out of her quarters to have a shower each and get changed.

'What was that all about?', I asked Tara and she shook her head. We head one last cuddle outside followed by a passionate kiss.

'Oh and mind your back', Tara warned me. 'I just got the feeling that your loyalties must be tested'

'Why?', I asked.

'Just a hunch' she said. 'And you don't want to fail'

The Captain was in a good mood at dinner, and she joked with all the offices at the Captain's table. I felt better now that I was washed and dressed again. She still referred to Tara as the 'dirty slut' when talking to Anne and I blushed – that didn't go unnoticed.

The evening was glorious. The Sun was still lingering in the night sky and it was very warm. I was glad to get out of hot, airless galley onto the breezier deck but it soon filled up.

The Captain arrived shortly afterwards and sent for the mat. 'There is to be a special match tonight', she warned and looked at me. I felt my heart sink. Tara vs me ... I just knew it. It seemed to good to be true with the Captain letting Tara and I enjoy an hour or two of fun. It was just too good.

I was wrong – well partly. As the entire crew crowded round the mat I stood next to Tabatha and waited. Lieutenant Ruth had donned her usual blue ringmasters outfit and was waiting for the mat to be set up and for Seawoman Alice to retrieve the box of nasties for the losers.

The Captain took centre-stage and addressed her crew. It had been a trying voyage she said, and was proud of each and every one, but for the final night, she wanted to fight. And she wanted to fight ... me!

My heart sank. I didn't want to fight my Captain. She had done so much for me since I was found on the ship. Everyone had told me that by rights, she should have thrown me overboard, but yet here she was wanting to fight me.

Then it occurred to me, was this my test? I was so deep in thought, Tabatha had to prod me, for me to get ready. The Captain had already taken off her boots, and her jacket. Was this the Captain's way of checking my loyalty, I thought as I took off my boots slowly. It had to be. This was for me to lose – after a good fight, obviously, so the Captain would strengthen her grip on the crew and gather more respect. Lisa aside, I didn't have a bad record in the wrestling!

I took off my jacket and passed it to Tabatha. She was smirking at me. I think she knew what I was thinking.

I faced the Captain from the other end of the mat and bowed towards her. She fixed my eyes with a steely gaze and Ruth started the contest.

Like so many of my contests, we fell into each other immediately, both scrapping to try and gain some sort of commanding position. The Captain was strong, and was beginning to pin me down when I rolled out of it, scrambled to my feet, and pounced on her in a rugby tackle. Landing on top of her, I scrabbled to grab hold of her shorts, but she managed to push me off, and we retreated to opposite ends of the mat.

Sizing each other up for a moment, I became aware of the crews shouting and jeering. They were rooting for a victory for their Captain, but I wasn't an unpopular contestant, as when we came together and I pushed her on her back there was still some cheering as I neared a victory.

It was a victory I couldn't take, and instead of pouncing for the kill by seizing her legs I faked a stumble and allowed her time to regain her footings.

I knew that the longer this went on, the more in danger I would be to doing something I shouldn't and therefore I concluded that I would have to lose quickly. Coming together for a third time, I let the Captain overpower me, and with my neck pinned against the floor with right hand, she calmly slid down my shorts with her left.

I lay there panting for a few moments. I was genuinely out of breath but saw that the Captain was up immediately, holding my plundered shorts aloft. I could hear cheering and some jeering being directed at me.

The Captain held her hand out to me, and I took it, with her helping me to my feet. 'Too strong for you, Cabin Boy?'

'Way too strong for me in the end', I told her so everyone could hear, and she beamed.

'Go choose your forfeit unless you want the Monster up your backside?'

'No Captain', I told her and scurried away to the box. I choose the smoothest and smallest strapon that Ruth had – a bright pink affair with a pink leather harness. Ruth had squirted some lubricant in my hand that I eagerly rubbed up and down the shaft of the bright pink dildo and my butthole.

'You like pink then?', the Captain cried as I gave it to her. The dildo was only about 5inches long and less than an inch wide, but as the Captain strapped it to her, it looked menacing and vicious.

'On your back, Cabin Boy', the Captain called out to me and that raised a cheer. 'I want you to see your Captain as you are fucked'. I tentatively laid down on the mat and waited for the Captain.

 
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