Chapter 5: Holly starts behaving

The sail proved to be a nice distraction for the Captain who seemed at ease ordering her crew around while her juices dripped down her legs and she was half-naked. I brought her some clothes and her boots out to her after tidying the room, which she did put on eventually.

Tabatha gave me an all-knowing look but the amount of noise the Captain makes when orgasming I was sure that the entire ship knew she got herself off. Not that it bothered her, or indeed anyone else. It was after-all expected that a Cabin Boy should satisfy his Captain in every way.

After dinner however, I found myself on the main deck half-naked and being whipped with the riding crop on my bare arse for the third time in two days due to Holly. She had overslept that morning and the Captain had waited until the evening, and postponed the strip poker games to exact punishment.

Fortunately, the crop was passed to Africa and not Holly who was tasked with giving me ten moderately painful swats across my backside. Each hit caused me to yell out but the pain was bearable. Holly was sulking as the Captain had made her give the crop to Africa for my punishment and stood in my direct line of vision as Africa brought the crop down for the final time.

After the punishment, the Captain sent me on an errand to the top of the Crows Nest and then, just as the Sun painted the ocean a violent array of yellows and reds, I was sent to my quarters to contemplate again why I was being punished.

I had two hours to concern myself why this was happening to me. Was my judgement really that wrong with Holly? It must be. My painful arse is testament to the fact that she is simply not mature enough to be here and I secretly hoped that it would be a short trip. Angry and annoyed I fell asleep around eleven with the sounds of a happy, horny female crew playing games outside my room.

I was awoken by a blood-curdling scream in the middle of the night. Slipping my skimpy shorts on and grabbing my cutlass, in record time I stepped into the corridor barefoot and edged along the entrance onto the main deck. Just as I was peering out onto the main deck at some shadowy characters, the Captain stepped out of her quarters and whispered to me.

'What is going on?'

'I don't know, Captain. I was just taking a look ', I replied truthfully and she stepped into the corridor, and with us both in shadow, we peered out.

Holly was clearly naked and tied spreadeagled to the riggings with her mouth being restuffed with some sort of fabric. Four shadowy figures had obtained part of a thick rope and were taking turns lashing her back, arse and pussy with it.

'Cabin Boy ... have you had something to do with this?', she asked me.

'No, Captain. I promise'

'You better not be lying', she warned. Even though she had some sort of gag on, her muted screams travelled in the still air.

'Shall we stop it, Captain?', I asked as she took in the scene unfurling behind her.

'No', she told me in hushed tones. 'Give it a minute'.

Holly was hit again and she screeched in agony. I kind of felt for her. She was only 16 after all.

I heard Commander Helen poke her head out of the door but the Captain sent her back to bed and went back to watching the torture of Holly.

'Ungag and untie her', one the figures said in a familar voice. It was Tabatha; I was sure!

Two of the figures moved forward and played with her hands and feet, before removing her gag.

'You've made me bleed', an indignant Holly spat at her tormentors.