There’s no such thing as a “worthless slut,” but I like the moniker.

We’ve discussed elsewhere, but I would love to find your limits. I want to hear how you yelp and gag, hear the change in your tone and pitch when the group party goes from fun to questioning whether you’re still good or if it’s safeword time.

Most of my faves are unavailable on the web or seriously hard to find, so they’re downloaded to my local server. And therefore not generally available.

But for stuff on the web…

https://www.xvideos.com/video.uvteoeha2fd/19yo_rachell_gets_demolished_by_6_men_in_wild_gangbang I love almost anything that involves a fucktoy just getting chewed up and wrecked. This one fires on all cylinders for me.

https://www.xnxx.com/video-13emr7a4/man_offers_his_newly_wed_wife_to_his_two_buddies Extra points for the maritime signal flags and her initial protest when the other guys start groping her.

https://www.xnxx.com/video-w14f332/3_friends_dump_their_loads_of_cum_in_my_slutty_pussy_breeding_me Taking turns on a bareback fucktoy.

https://www.xvideos.com/video.oiaudl61e3/riley_from_secret_friends_-_gangbang_and_creampie Classic from the spankbank. All holes, creampies, just a bunch of dudes going to town on her.

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.

Mixing some reality with the fantasy (long-term goal?), crew slots are absolutely positions to which one applies. Your asking salary is completely acceptable; most crew are unpaid anyway. In exchange for their duties performed, crew receive food*, passage, and documented hours at sea (necessary for things like a captain’s license or Merchant Marine certification). Team fit is critical, and drama gets one immediately offboarded at the nearest port. We will absolutely detour if someone causes drama.

*My partner and I are excellent cooks. Crew eat very well on our boat.

Duration of crossings and deliveries are a matter of distance, time of year, weather, hull length, and sail configuration. Going to or from Hawaii is roughly two weeks from SF or San Diego. So, a week or two down the coast from Puget Sound, and another two to Hawaii. I haven’t yet sailed to Southeast Asia, but that is generally another two or three weeks from Hawaii.

When I do deliveries of someone else’s boat, I prefer a crew of five, but four is the minimum. I can singlehand my own boat, but for trips of less than 1000 nautical miles, it’s usually just my partner (F51) and me (M55). I will take on two additional trusted crew members or friends if they express interest. For passages on my own boat, four person crew, maybe five if one of them is a close friend. So that would be me, my partner, you, and up to two other crew.

Clearly, you will require some training, both on sailing and anal capability. I was a professor in a past career, so I’m familiar with the need for progressive training. Line handling and winch grinding are regular, introductory duties, and everyone has at least two duties aboard. I’d have you perform those tasks while wearing butt plugs of increasing size. I would of course personally oversee and evaluate your development as a three-hole fucktoy. Although now I’m pondering lashing you to the mast in a bent over pose with a jaw spreader. Keep all your holes available while preventing you from clenching your jaw in heavy seas. I am firm captain, but I am fair; there will be a bottle of lube tethered to your PFD. PFDs are required for all crew outside of the cockpit, even if they are otherwise naked. Safety first and all.

My friends and I are a respectful, inclusive bunch. I insist on compassionate communication at all times. It helps to keep things calmer when the real stressors hit, like ocean storms. We don’t have derogatory names for people with whom we willingly associate, nor do I tolerate them. As such, “slut” is a statement of fact, not a pejorative, in our lexicon. However, we are also a very creative bunch and can come up with all kinds of monikers for your role aboard. And I am always willing to make reasonable accommodations, especially for high-performing crew. Free Fuckhole? Crew Cumdump? Winch Wench? We’ll workshop that one and find something mutually amenable.

What other questions do you have about the role?

That is a broad, blanket statement overlooking a constellation of preferences and proclivities. For example: free use, CNC, bored and ignored, to name just a few. Something even more obvious to a person: not getting sex from one’s partner and the lower-drive partner can’t be arsed to do something about it.

Jesus Christ, 2-5 times

The perimenopause has been brutal on me. :D She’s doing great, thanks, been in remission for two years.

So, here’s the deal with monogamy: when partners insist on monogamy, the implicit corollary is that both necessarily assume full responsibility for their partner’s sexual satisfaction. Too many people overlook the GGG aspect; they want the mental ease of monogamy without putting in the <ahem> hard work.

That’s a lot of words to say: I got nothing to offer that lines up precisely with your question. The partner with lower sex drive invariably gets exactly what they want while the partner with higher sex drive must remain unsatisfied. I have experience on both sides of this issue, and compromise is critical to all interpersonal dynamics.

Empathy by way of anecdote: my partner of eight years (female) wants sex about two to five times per day. I (male) have bandwidth and libido for once, maybe twice, a day. So… she gets a lot of cunnilingus. When she was undergoing chemotherapy, she had vaginal tenderness and dryness that made PIV sex and cunnilingus uncomfortable for her. But she wanted to be there for me. So there was a lot of jerking off in her mouth and using her ass cheeks as a fleshlight.

Much like polyamory/ENM, monogamy requires a lot of Jedi Master level communication. But without the mind tricks.

Love the “Story of O” vibes.

The fantasy I want to live out is about the same as what I do/want to do with my current partner: CNC three-hole gangbang with my sailing crew. You and my partner getting utterly railed and used as cumdumps. During an ocean crossing, relaxation is enforced policy for those not on watch. What better way to relax after a shift than to relieve that tension into a hole or three of the available bilge bunny? And she would pretty much always be available.

Another long-running fantasy I have is what I call Flotilla Sluts. Some sailors, including yours truly, sometimes travel in flotillas, i.e. a group of sailboats. Crew and resources can be shared as necessary, and there is safety in numbers. I often sail with two or three other similarly sized boats so that we move at roughly the same speeds. It helps that we captains are all very close friends of decades. It also helps that two of the other captains are kinky motherfuckers. I want to add two Flotilla Sluts to my crew roster. We would rail these women on the regular, full freeuse. I would love to see cum running down her thighs every time she was walking around.

When stuck in doldrums, I would lend one of my Flotilla Sluts to one of the other boats. Upon return, I would photograph her bruises before adding my own and railing her sore holes.

In true service submissive fashion, these Flotilla Sluts are a social glue, the backbone of the fleet. Crew and fleet cohesion are critical, and we would all rally around our Flotilla Sluts. The captain is responsible for everything on their boat, and the service subs would be well-cared for.

Aftercare plays into this fantasy too. I want to gently sponge-bathe my bilge bunny, tuck her in, caress and show my gratitude for taking care of the crew and me. I would wander my hands gently over her bruises, brush her hair smooth, bring water and a snack. Discuss how she’s holding up. She’s going to need her energy because we’re still a week away from the next port.

I love when old(er) folk have great adventures and anecdotes to share. And proceed to share them.

He at one point met with Howard Hughes, but in a bathroom at Boeing Field. No, not gay stuff

That qualification gave me a good chuckle. Thanks, cheers, and enjoy your holiday!

This used to actually be fairly normal (at least, within the realm of taboo social sex activities), its where the term ‘swingers’ originally came from, way back in the 50s/60s.

According to “The Lifestyle: A Look at the Erotic Rites of Swingers” (Gould, 1999), key clubs originated with WWII pilots, but entered the lexicon as key parties in the 50s and 60s. However, all the academic study is based on secondhand accounts. It’s the kind of thing that leads me to wonder if “key party” was some kind of Urban Dictionary expression with someone making up the term for giggles. The expression entered the lexicon and some people then tried it out, i.e. the vocabulary preceded the social trend.

Non-monogamy does seem to be the human norm, and it’s a bummer there’s so much unnecessary taboo and complexity wrapped up in non-monogamy.

I also fully accept that we’re just not moving in the correct circles for our goals. Working on it!

The largest age difference I experienced was when I was 17 and she was 38. The most significant difference was when I was 29 and she was 42 (and one of my professors). In my experience, older women with whom I had sex possessed way fewer hangups than women my age. But that could easily be attributed to mutual self-selection.

The lack of hangups mostly manifested as stuff like:

• secure and comfortable in their bodies
• more willing to experiment in raucous, ribald ways
• into, or at least willing to do, anal
• more knowledgeable about what works for them
• more eager to do what works for me, even if they weren’t into it themselves

You can cross the ocean safely and in comfort on 30k yachts, 10ish metres.

And even less than that! Anything can be a dildo if you’re brave enough.

Great look, fun pose, dynamic lighting… Clean your lens. Looking forward to seeing more.

Quite probably. Two problems with that. We live on a sailboat far from any lifestyle clubs; this introduces all kinds of logistics complexities in getting to the LS clubs. Sure, that’s an “Us” problem. We’ve gone to LS clubs and meetups, but our experience has very much been that it’s a hookup scene. We tend to be a bit more demisexual and want a connection with our fuckbuddies. Quality over quantity, ya know? We also tried a few LS sites and apps. Those have been attempted scam, photo-collectors, hookup scene, wannabe bulls/cuckqueens (no, I don’t want to humiliate your husband while we fuck), or some combination of those.

We’re willing to hold out to find exactly the dynamic we want and explicitly indicate in our LS profiles.

Probably my favorite was the FWB arrangement with my best friend. I mean, sure, sex at work is great. But NSA, guilt-free sex with person I’m hanging out with anyway? That shaped my intimate relationships moving forward. The sexual dynamic set me up for a lifetime of a non-dysfunctional regard of sex, ethical non-monogamy, non-jealousy, and compersion.

Not mentioned earlier: the captain of the high school color guard dropped by my townhouse one night. I was initially very pissed off that someone just showed up at my home. More than that, I was seriously perplexed how the hell one of the hottest girls in school knew where I lived, much less know my name. Her best friend had gotten too drunk at a party and needed to sober up before getting dropped off at home. The captain and I were just chatting while her friend laid on the couch. I don’t even remember how it happened, but we were suddenly making out and then in my bedroom having sex. It was very vanilla, and I was so nervous that I couldn’t get off. It was all so surreal that I thought I dreamed it. The following Monday, my best friend (the lesbian) kidded me about hooking up with the captain of the guard. Turns out the captain was asking my friend about me, told her about the sex, and how to ask about being able to drop by more often. There were, for better and worse, no further visits.

Oh, absolutely. From 2015 until 2017, one of my lovers was a free use submissive. Whenever my best friend was in town, I’d have her come over and we would go to town on her together. He’d never done anal theretofore, so I would make sure he was properly lubed and guide him in. He quickly got the hang of it. But it was still fun to guide her onto him or guide him into her. He’s married now and extracurricular play is not on the menu :/ Which is a bummer because my current partner is very into group games.

I was a very early bloomer, so my stories start earlier than you asked. Girls never had cooties in my book; I wanted to kiss girls since kindergarten. And I was (am) intractably horny. If sex addiction were a thing, I could be the poster boy for high-functioning addiction.

My female cousin was my next door neighbor, and she is two years older than I. She taught me how to masturbate one xmas morning. Best xmas gift ever! Every single opportunity for privacy, we were naked and all over each other, trying to find ways to feel good. My parents divorced when I was 6, and I moved away with my mother. My cousin and I would have definitely taken the play as far as we could had we stayed in proximity. We talked about our sexual journeys and adventures well into adulthood until we fell out of touch after she married. Having that open conversation, free of shame with a trusted sounding board, was an immense boon to my adolescent journey.

Up until about 10, I had a string of babysitters. The first one had an early teen daughter who frequently wanted to do naked playtimes, which I loved. She would climb on top of me and rub her naked crotch on mine until she was done. I was very disappointed when my mother got a new job and we moved away.

My next babysitter was the buddy of my mother’s friend. He and I would sit on the couch watching TV. It wasn’t long before he started groping my crotch. Despite knowing this was “wrong,” and not being into boys at all, it still felt great. After a few nights of him groping me, I worked up the nerve to unzip my pants and encouraged him to go further. Things got really assertive, and before long he was jerking off in my mouth. His glans just barely fit in my face, but I was having fun.

After maybe a week of that, he started fucking my ass. Goddamn, that hurt and felt great at the same time! I loved the feeling of when he would cum in me and lay on top of me while he caught his breath. I didn’t understand the cumming part at the time, but I enjoyed the slippery feeling when he was done. I would be antsy all day at class, looking forward to going to my babysitter after school got out. I got in “trouble” at least a few times by going straight to his room, pulling down my pants, and getting face down with a pillow under me. I wanted to do the bedroom stuff all the time. I absolutely welcomed everything that happened and still reflect fondly on my adventures in exploring my sexuality with him. I was very sad when his job relocated him. There weren’t any babysitter adventures after that, and my mother decided I was old enough to be a latchkey kid.

When I was 14, I got my first “real” job. My boss was gay and always flirting with me. That was when I discovered top vs bottom. And he was very much a bottom. There was an elevated counter towards the back of the store. People couldn’t really see what was going on there, but we could see everything. He would blow me and let me fuck him any time work was slow. I still wasn’t into dudes, but any port in a storm, right sailor? :D Work has never been as fun as that. It was a lot of fun to quench my adolescent libido with another person, even if it wasn’t with my preferred gender. I also fully realized that I’m very much a top/Dom and I had a drive to spank and slap sexual partners. Moreover, I realized there were people who enjoyed getting spanked and slapped during sex play.

Things actually got mostly tamer from there. I moved out on my own when I was 16. I was oddly protective about my townhouse and was very wary of letting anyone visit except my besties. Because of the self-imposed domestic solitude, I came up with all kinds of ways to jerk off. My favorite was using a long, skinny balloon (like used for balloon animals), twisted in the shape of a vagina. I would lube it up with K-Y and spend a whole day fucking my balloon pussy. :D It was always tragic when I ran out of balloons.

Things got a little unhinged for a brief stretch. One of my good friend’s GF was seriously into me. She was very assertive about it, and who am I to turn down sex with a hot girl? Turns out he was into that and knew everything. She and I would make out in the elevator. We’d fuck at my place after school. She and her family moved out-of-state about four months after we started fucking, and we were both really bummed.

And my last teenage hurrah: at 17, my best friend at the time was (still is) a lesbian. One night while hanging out, she blurted out that she was really horny and asked if I would be willing to engage in a mutually beneficial arrangement. Absolutely, “but… you’re a lesbian!” There was some deep conversation: I couldn’t use her mouth or pussy, so it was anal-only. She introduced me to anal sex with girls/women, and that kink is solidly with me almost 40 years later.

The sexual portion of our friendship was a lot of free use, a term which I didn’t know at the time. Most of the time, it was just one of us getting off. We explicitly coordinated available times, breaks between classes, etc. all to assure that we could be there for each other’s needs. When time ran short, we would alternate days on who got to come. On weekdays, she would drop by after class and have me go down on her before she had to rush home, and the next day I would get to use her ass. On her days, sometimes she would have me fuck her while she masturbated, but because our time was limited, she was done once she came. I never did learn how to cum quickly. :D She would come over on weekends, and we’d would fuck around all day. She also taught me how give head to women which has paid massive dividends all through life.

If you’ve got the skills, we are always vetting crew for sailings.

My partner and I own a sailboat, and we do ocean crossings.

That part isn’t fantasy. We own a 46 foot ocean-going sailboat.

She’d look damn good laying out in a skimpy bikini while sailing.

If it’s warm enough to wear a bikini while sailing, she’s not wearing a bikini. :D

M55 and my partner F51 is a service submissive. She absolutely gets off on being helpful, getting used, and generally being a positive addition to any situation. Sexy funtimes do nothing for her unless she gets me off first.

This is not just my fantasy, but one of many similar fantasies that we have shared and refined together. Ever since we started dating, I have wanted to push the limits of her service subbiness. It would all start innocently enough: she makes cocktails and snacks for me and a few friends, some innocuous flirting and cheeky comments. But as the evening turns into night, everyone starts getting a bit bolder. Hands start wandering, ribald quips turn into outright propositions. Slowly then suddenly, she’s on all fours and we’re spitroasting her, taking turns in all of her holes, and using her as the entertainment center. She is getting to express the full breadth of her full three-hole slutdom.

More kink than fantasy, lately I have been using her mouth as a spank sock. When I need stress-reliever, I tell her to come into my office and kneel down. I queue up one of my favorite porn shorts and throat-fuck her until I cum. I then leave her hanging until my workday ends. By the time I get around to taking care of her, her panties are thoroughly soaked. She is a very, very good girl and I am grateful for her every day.