no joke I would do this for real so fast if it weren’t for life obligations

"One doesn't discover new lands without consenting to lose sight of the shore." - Andre Gide (although others have also said similar things). It applies to way more in life than sailing.

Line handling and winch grinding are absolutely real activities on a sailboat. As is "Rail Meat." :D There are lots of lines (another word for "rope that serves a specific purpose"). For example, there are lines to hoist, control, and trim the sails. The two main kinds of lines attached to sails are halyards and sheets. Halyards raise the sail and keep it vertically tensioned. Sheets, very generally speaking, control the horizontal position and shape of the sail. Those lines are controlled by winches, and it's a workout. It's more about arm endurance and stout core muscles. How's your core strength? But seriously, a few training sailings, and even the weakest crew quickly develop the economy of motion needed to grind winches. BTW, Rail Meat are people who sit on the windward side of the boat to help it sail flatter, although that's usually for racing.

though the anal part would be rough, not completely inexperienced there but it’s always been a bit rough

If you think that's rough, wait until you experience your first Pacific Ocean storm. :D It can be downright terrifying, and I have a boat designed for it. But seriously, I've anally trained all my subs. Time, patience, communication... much like so many other things in life. Sure, some of my subs can take more pounding than others, and it's on the captain to understand and respect the design limits of all systems in use.

isnt there something about a sailor’s mouth

I'm living proof. I regularly curse up a storm.

Degradation isn’t the same as disrespect if its consensual.

Agreed and point taken. I am strict about negotiating scenes and communicating boundaries.

i dont know boat terms

The vocabulary list is unreal. It's a whole other language. When a landlubber hears my friends and I chatting, they be all like, "Are you even speaking English?" But you hang around boats for a bit and it becomes natural. Like learning any other language, immersion is key.

What’s the most men I might end up servicing?

At one time? Three crew. You have three holes, and boat resources must be shared consciously and conscientiously. Also, crew are either on watch, on maintenance duty, on enforced downtime/relaxation, or sleeping. That also applies to the bilge bunny/cabin girl. We would have to be in good stead (sails trimmed well, moderate seas, everything aligned) for three crew to be available for entertainment. I hope you're good at cunnilingus, because my partner will need some cum cleaned out of her too.

Now, when becalmed or in port, the only sequential limit will be how busy the other flotilla crews are with post-sailing responsibilities. Two of my other sailing captains are married. One, whom we'll call Ted, will return you to me bruised, battered, and well-used. I look forward to tending to the necessary refit and refurb of my bilge bunny. The other captain, "Colin," is a bit more lower-case 'c' conservative in his proclivities, but has been questing for a unicorn. There is a third captain, "Edward," who is a total degenerate to whom I wouldn't lend a rusty socket set, much less the woman I'm using as my personal ratchet. But he usually books solid, trustworthy crew on his sailings.

Colin's son is 18, and I suspect could fuck you raw on his own. So, no, you wouldn't be the youngest, although you would most likely be the youngest on my boat. Young crew tend to come from racing backgrounds, and racers tend to put too much stress on the sailing rig when they are at the helm. While my boat can take it, it just means unnecessary premature wear.

I have been thoroughly trained in that department, and get pretty regular practice

I'll just have to ascertain that for myself. "Trust, but verify." Everything and everyone on the boat is the captain's responsibility, after all.

would i be able to keep videos?

Of course. They're yours, after all. I'll even edit them up into a highlight reel for you.

And what happens if I refuse boat related duties like line handling if that’s a real thing

I am adept at dealing with brats and constructively breaking the wills of those who disobey direct instructions. For starters, there is a lot of rope aboard a sailboat, and sailors are ace with knotwork. It would be a trivial task to tie you up safely yet in maximum discomfort until you reconsider your insubordination. I also have a 24 inch acrylic "ruler" (it's for spanking). The ruler can do everything from playful taps to leaving sexy welts to literally opening up skin. No joke: I once used it for self-defense when someone tried to break into my boat one night. Laid his cheek right the fuck open. It took a bunch of scrubbing to get his blood off the teak.

But that's just the physical motivation. Psychological warfare is just another flail in the leadership toolbox. How well would you thrive in the absence of approval, attention, and being put to good use?

But seriously, if (when) the shit hits the fan, you'll be begging me for instructions. In a storm, you'll wish you were getting your ass railed without lube rather than staying belowdecks, clinging onto handrails to prevent flying across the cabin. And why would you be belowdecks? Because it's your off-shift. You refusing your non-sexual responsibilities is functionally the same as a crew member being seasick or getting injured, so you'd be off-shift. Crew rosters are planned around these contingencies.

FWIW, line handling is generally just keeping the sheets "dressed," that is neat and out of the way. It's a great job for neat freaks and people who don't want to trip their way into a head injury.