Wild Bill 1

"Do you remember that time Bill brought that gorgeous big tit redhead from the nurse convention over to your boat?"

They'd been drinking on Don's boat for a while when the topic of Wild Bill came up.  

Don groaned, "Of course I do.  They kept me up all night.  Every time I would think they were done, I'd hear them start back up again.  I have no idea how many times they did it, but the poor girl looked like she could barely walk the next day.  I'm pretty sure she'd never met a man like Wild Bill!"

They both laughed at that.  Not many people had.

***

It was a smallish marina in Key Largo, and there weren't many permanent residents.  Four of the most prominent residents lived in a cluster of slips at the end of the marina.  There was Maggie, a middle aged widow who kept a party going on her 70 ft motor yacht almost constantly.  She bribed the local cops and sold drugs to the party goers to pay her bills.  Rumor was that her slip fees were much higher than every one else's to compensate for the noise and chaos her party generated, but apparently it was worth it to her.  

There was Charlie, the good natured veteran who lived in a 55 ft motor yacht.  He was a bit of a good samaritan and seemed to always have different women around that he treated like princesses until they inevitably dumped him.

Don was a middle aged divorcee who had a 45 foot sailboat parked right next to Bill.  He was a day trader who made enough to support his lifestyle but not enough to actually get rich.  He picked the occasional girl up from Maggie's parties, but otherwise was a spectator.

Then there was Wild Bill.  No one knew much about his background, but Bill had enough money to not need to work despite being in his late 30s or early 40s.  He was tall, light haired, very handsome, and very charming.  He had a 60 ft custom motor yacht that he cared for meticulously.  He was quick to help out the other boaters in the marina, but he never asked for anything.  The truth was that everyone liked him, especially Maggie who obviously had a bit of a crush on him even though she knew about his dark side.  That said, she never really tried to land him, possibly because of his dark side.

About a month after he arrived at the marina, a group of college girls showed up at Maggie's boat and started partying.  Wild Bill was there already, and Charlie and Don watched as Bill picked off an very young and attractive blond straggler.  He fed her a couple of drinks, chatted her up, and then they left together.  Charlie and Don smiled at each other, pleased for Bill's success but not surprised.  He was a handsome, wealthy, fit, and charming man.  It was no surprise that the young woman liked him.  

However, Charlie and Don were very surprised when the young lady limped off of Bill's boat two mornings later.  They had forgotten about her.  So, to see her cringing and walking gingerly as she exited Bill's boat was quite a surprise, and they both sat in stunned silence as she limped out to sit on a bench until a cab arrived to pick her up.  She looked exhausted and frazzled with no makeup on, and she looked like she might start crying.  She was performing the ultimate walk of shame, but Don and Charlie were to later see that she was very far from the last woman to limp off of Wild Bill's boat.

***

The redhead had been a somewhat similar story, but it educated Charlie and Don a bit on what happened when Bill got a girl alone.

Bill had been in the marina maybe six months, and they'd each seen a lot of women make that exhausted walk of shame off Bill's boat.  Some seemed very young, some were certainly older than he was, but every one looked like she'd been ridden hard and put away wet when she emerged.  On a couple of occasions they had seen two women leave the same morning, and both women looked like they had run a marathon.

In late summer, Bill's boat was in dry dock for maintenance, so when he hooked the redhead from Maggie's party, he asked Don if he could use his boat.  Having had a few too many drinks, Don stupidly agreed.

A couple of hours later, Don returned from Maggie's boat and fell drunkenly on the couch in his main cabin having completely forgotten about Bill.  Sometime later, Don woke up to a loud slapping sound and a couple making all the noises you'd expect, but the woman's voice had a note of desperation.

"Oh god, I can't believe... I can't believe you're still hard."  He heard Bill laugh and say, "Baby, I'm still getting warmed up."  She sounded like she started to protest, but her words were cut short and she made a choking sound.  Don heard Bill say, "You ever been choked while you cum?  You'll love it"  just before he drunkenly passed out again.

Don tried to sleep and the booze helped a lot, but the sound of the obvious discomfort in the young woman's voice and the occasional screech when Bill slapped her ass made it difficult to stay asleep.  For Don, the night became a dreamlike collage of semi-conscious memories broke through his drunken slumber.

..."God baby, not again!"...

..."Please don't, I've never done that! ARGGH! PLEASE TAKE IT OUT!" before her voice became muffled like her face was pushed into a pillow...

...Don woke up to repetitive choking noises followed by gasps for air before the choking started again...

...Desperation: "Not in my ass again, please fuck my pussy, please, PLEASE" as slapping sounds filled the boat, but this time linked with feminine grunts of pain...

... Weeping, "Please, I need to sleep" as slapping sounds again filled the boat...

Around dawn, Don woke to the girl grunting in time with that same loud slapping sound and heard Bill say, "baby, your ass just swallows my cock now, but I love how it tightens back up when I choke you."  It sounded like Bill slapped her face roughly, then the buxom ginger coed started making choking sounds like she couldn't breathe.  Don thought about how pretty she was, with her slender figure and large tits, then decided he needed to leave.  He was exhausted.

***

Don moved to Charlie's boat and slept much of the day.  In the evening, Don and Charlie had cocktails on the deck of Charlie's boat and listened the redhead grunt loudly as Bill took her again. The thin walls of Don's boat utterly failed to contain the girl's use.

"It's amazing.  I had no idea." said Charlie.

Don replied, "I think we had some idea, but it seems like his cock never really gets soft.  He just takes them and then takes them again.  i can't decide if I'm jealous or sorry for him." 

A short scream sang thru the night air as Bill did something the redhead objected to.  then she said, "PLEASE, NOT MY ASS AGAIN!"

"I'm pretty sure I'm jealous" said Charlie.

***

About 10 o'clock that night, the lovely redhead nurse emerged from Don's boat very much worse for the wear.  Her pretty hair was in a rough pony tail, she had no make-up on and her red swollen eyes told the story of her recent past.  She had hickeys visible on her neck and one particularly dark one on the top part of her boob visible thru the neckline of her wrinkled party dress.  She walked gingerly as if she was very sore, and apparently her underwear had been lost as her generous tits swayed freely under her thin dress and they could clearly see cum drooling from under her short dress and down her pretty leg.

Wild Bill came out behind her as if it was just another beautiful night in South Florida.  He said, "My car's over here baby, we need to get you on the road or you'll miss that redeye flight back to Indiana.  That last screw almost made us late."

"I know, that's why I asked you not to fuck me again.  And I'm so sore..." she said weakly.

Bill smiled genially and said, "I'm sorry baby, but when I realized you were leaving I needed one more taste off that sweet butthole."

They turned away toward Bill's car, and their voices were too muffled to hear.

As she weakly walked towards his car, Don and Charlie looked at each other as they realized Bill had fucked her right up to the point where he almost couldn't get her to the airport in time for her flight.  She'd spent about 24 hours with Bill, and they'd never left Don's boat.

***

The next day after a few cocktails, they talked to Bill about it.

"Ha, I'm not really sure what to say.  I just get hard around a beautful woman, and I stay that way.  Heck, sometimes the gal isn't even that pretty but I'm still hard as a diamond.  After the first few times I can't even squirt anymore, but I'm still hard.  I still cum, but nothing comes out.  It's a weird feeling, but it's still incredible.  I actually saw a doctor about it a few years back, he called it Priapism."

Don asked, "Don't they want to leave after a while?"

Bill chuckled amiably and said, "Sometimes they do, but it's never too hard to convince them to stay."

Charlie also chuckled then lifted his cocktail glass and said, "Well, my friend, I wish I had your stamina!"

Don said, "It... it sounded like she let you do anal to her.  I was a bit surprised, she didn't seem the type."

Bill laughed then said, "My friend, they are all the type.  The key is you don't ask, you just take it."

They laughed and toasted to Bill's wisdom.

***

Later in the Autumn as the tourist season really kicked in, Wild Bill landed the identical twins.  No one was sure where they came from, but they just turned up on Bill's boat one day.

They were lovely latinas in their mid 20s, and it was clear they'd never met anyone like Bill, who was obviously wealthy and lived on a yacht.  He treated them like princesses in public, but the squeals and other sounds of rough sex that emanated from Bill's boat told a different story at night.

Over the next few weeks, it was a common sight to see one of the girls sunning herself on the deck of Bill's boat while the sounds of rough sex filtered out from Bill's cabin.  Less common but still frequent was when both twins were below deck, and their voices alternated as he rotated between them.  

Don, Charlie, and Maggie watched for the better part of a month as Bill used the girls up.  They went from lively and energetic young women to hollow eyed husks who walked uncomfortably around the harbor with their skin marked by small bruises and hickeys.  They seemed mentally addled, which might have been the result of drugs but the marina folks chalked it up to getting fucked mercilessly day and night.  Don and Charlie were pretty much amazed that Bill had landed the lovely girls and then kept their attention for so long, but Maggie vacillated back and forth between feeling sorry for the girls and being intensely jealous.

Finally, the girls just disappeared.  Bill had taken his boat out for a cruise with them, and when he came back they were gone.  He later explained to Don and Charlie that they cruised down to Key West and the girls wanted to stay there.  

Charlie had made the trip to Key West many times, and it seemed like Bill had made the roundtrip in record time, but he figured maybe Bill's boat was a bit faster than his.

***

The situation slowly evolved to where Maggie would push her more irritating guests toward Bill.  Over time, Maggie ended up understanding Bill far better than Charlie and Don did.  Bill slowly began to share with Maggie the sordid and often disgusting details of what he did with his women.

That loudmouthed middle aged brunette who argued with Maggie about politics?  Maggie introduced her to Bill and a bit later was surprised to see Bill slip some powder into the bitch's drink.  Maybe a half hour later, Maggie watched as the curvy brunette stumbled off her boat with Bill.  Maggie watched and heard the inebriated brunette giggle loudly as they walked across the lot to Bill's boat.  Three days later, that same big assed brunette looked pale and used up as she limped off of Bill's boat.  Bill later confided in Maggie that the brunette's asshole had been cherry before he got to it.  Maggie was a bit shocked, but Bill chuckled and said it certainly wasn't cherry anymore.

The entitled college freshman princess on vacation with her less wealthy/attractive friends?  She rubbed Maggie wrong and the pretty blond got fed to Wild Bill.  Her uncomfortable noises leaked from Bill's boat and echoed around the marina until Maggie almost felt bad for the teenager.  A week later, the girl emerged from Bill's boat like an abused moth from a cocoon, not prettier like a butterfly would be, but certainly changed by her experience.  Bill told Maggie that the girl hadn't had much experience, so he'd had to teach her almost everything.  Her holes had been very tight, but he loved watching her swallow him, so they spent a lot of time teaching her to swallow his cock with her slightly oversized mouth.  Months back, Maggie had accidentally walked in on Bill on her boat while a party girl was sucking him off and was startled by the size of his cock, so she reeled a bit at the idea of that huge dick being forced into the pretty blond's throat.  The girls vacation was seven days in the Keys, and while her friends drank and partied, Bill brutally used the beautiful young girl right up until she hobbled out of his boat to leave for the airport.  The same friends who left her with Bill picked her up.  They were tanned and smiling from their week in the Keys while their pale friend tried to look cheery and hide the toll taken during her ordeal.  

Lauren - the uppity middle aged business lady on vacation from her lawyer firm in NYC who talked down to Maggie?  Maggie called Bill and told him she had a curly brunette fish on the line, and he showed up a few minutes later.  Maggie didn't see him drug her drink, but when they left together, the bitch sure seemed malleable.  Maggie was vaguely jealous of the lady's thick and curvy body, and wondered for a few seconds if her jealousy made her call Bill.  Bill later told Maggie that Lauren told him she hated anal sex, so he made sure to fuck her asshole almost exclusively for the next two days.  He said he had to hold her down for the first few times, but by the time she left, she'd pull her fat asscheeks apart and invite him to used her gaping asshole.  He laughed as he described the painful grunts she made as she pulled her ass open and pushed back against him while trying to act like she loved being sodomized.

The chubby and overly talkative young teacher on vacation with her friends who decided Don was the love of her life?  Don simply said a few words in Bill's ear, and within a half-hour the girl was leaving Maggie's to get a tour of Bill's boat.   The next morning while most of Maggie's partygoers were passed out, Don stumbled back to his boat smiling while enjoying the sounds coming from Bill's boat.  The loud slapping noises combined with the loud female grunting made Don stop on his deck and listen in the cool morning air.  When he woke up a few hours later, Bill was at it again, and Don could hear the teacher trying to voice her concerns to Bill as he used her.  Don slept a bit more, then woke again to hear the chubby brunette grunting loudly in pain as Bill tore into her again.  Bill turned her loose a couple of days later, and she looked like a overworked $20 whore as she gingerly walked out to the waiting cab.  Bill later told Maggie the teacher had a kid six months back, so she was still very loose and he almost got his whole hand inside her.  She was also lactating, and Bill told Maggie how much he loved sucking her tits dry while he pumped himself in her sloppy pussy.  He drank much of it, but he also liked tongue kissing her with milk in their mouths so she could taste herself.  

Wild Bill became the "Easy Button" for getting rid of the more irritating gals who passed thru the marina.  Don, Charlie, and especially Maggie fed him an almost constant stream of ladies who drifted by.  Without fail, the women spent somewhere between several hours to a week with Bill and left broken and fucked out, or, for a few of the bitchier ladies who seemed to fight him a bit more, he cruised his boat down to another Key to drop them off so they could continue partying there.  

***

Maggie finally got too curious and asked him about the powder she saw him slip in girls' drinks.

"Well, I have a few things I use to help the ladies.  Mostly I use a ecstasy cocktail to make them feel hot but unrestrained.  If a girl is more feisty, I might use ecstasy with a little heroin.  It's a trick I learned in Thailand to help ladies relax a bit."

Maggie didn't know how to respond, so Bill simply said, "look, it's just a tiny bit to help these ladies loosen up.  After the first few hours they don't need it anymore and things progress naturally."

Maggie thought back to how pale and weak most of the women looked when they left Bill's boat, then "agreed" that it made sense to help them loosen up a bit.  She began supplying Bill's drug stash at her cost since he was so helpful around the marina.

***

It was a strange request, but before he left, Charlie told Maggie he'd be gone when the pretty blond arrived, so please introduce her to Wild Bill.  Everyone knew Charlie got into some strange and quasi-legal business dealings, but when the lovely blond showed up, they were still surprised.  She was a petite, athletic girl with nice curves and a sharp mind that she tried to hide, which was exactly what Charlie told them to expect.  Her name was Janine and she seemed immediately drawn to Bill, who fed her a few drinks and had her eating from his hand before midnight.  Don and Maggie watched the couple as Bill helped the lovely blonde stagger back to his boat.  They looked knowingly at each other, silently agreeing that she was about to be ridden like a racehorse.

The blond was one of the more attractive gals Bill had landed since the gang met him, so it figured that he'd keep her shacked up for a bit longer than average.  The beautiful young gal's grunts and yelps echoed around the marina all the next day.  Perhaps due to how pretty she was, Bill seemed even more active than usual.  The evening after Bill brought to his boat, Don and Maggie were having cocktails on his boat next to Bill's.  After fucking her seemingly all day long, they could clearly see Bill thru a large open porthole on the side of his boat as Bill roughly took the bent over blond from behind.  The girl grunted and looked like she was in pain as he used her.  At one point Don joked to Maggie that Janine had probly been screwed more that day than she had her whole life, to which Maggie sipped her Martini and replied, "I'm pretty sure she's never been screwed in that hole" which surprised Don enough that he almost blew Martini out his nose.  Maggie smiled at Don's shocked reaction and explained, "Bill and I have gotten to know each other a bit.  One of his favorite things in the world is being a gal's first, and most of the women he brings back only have one virginity left.  So he takes it, then takes it a few more times just to be sure.  Honestly, that's the main reason I never went back to his boat with him."

They sat in silence and listened and watched as Bill used a handful of long blond hair to pump his fat cock in and out of the beautiful girl's most private hole.  They watched Bill gradually speed up until he was pounding into her guts and the sound of her loud grunts filled the air.  Finally, after a long fuck session, Bill grabbed her hips, drove deep into the girl, and emptied what was left in his balls into her colon.  The scene froze for a few seconds as Bill came, then he pulled his cock out of the sweating and exhausted blond and walked around in front of her.  He took a handful of her hair, lifted her head off the bed where she had collapsed, then shoved his cock in her mouth and said, "clean my cock off whore."  The poor girl was too exhausted to resist and they watched as she started mouthing his filthy cock.

In the uncomfortable silence, Don simply said, "I don't see why you wouldn't go home with him, he seems like such a romantic guy."

***

Bill kept the girl naked and sweating for the next few days until Charlie got back.  They realized they could generally tell what hole Bill was using by the loudness and pitch of the noises she made.  Bill took her asshole often after that first night, and frequently they'd hear her yelp in the middle of sex and then transition to the guttural grunting that meant he was in her asshole again.  The pace of the sex slowed down a bit over those three days, but Janine was still receiving rough fuck sessions multiple times a day.  

Don was polishing the metal fixtures on his boat deck listening to Janine's grunts of pain as Bill used her asshole again.  He figured Bill would have to emerge soon if just to get more food and booze to fuel more rough sex.  He thought back to what Bill had told them about having a constant hard-on, even when he couldn't shoot cum anymore.  Don figured Bill's balls had to be empty at his point. 

Charlie had been gone since before Janine arrived, but Don watched as Charlie pulled his car up with cute brunette in the passenger seat.

Charlie and girl walked over to Don's boat and stood on the dock as if they were about to say something, but instead listened to the sound of hips slapping in time with the pretty blond's grunts.

"Still at it, huh?" Charlie asked.

"I think Bill will keep her around for a while.  She's beautiful."

"She sure is.  I figured they'd still be at, so I brought groceries for them."

Don grinned and said, "wow, no rest for the weary girl, huh?"

"I guess I should explain.  This lovely lady next to me is Tiffany.  A few months back, Janine seduced Tiffany's husband Phil, successfully ending their 10 year marriage.  Janine then cleaned out Phil's savings and disappeared with a considerable amount of money.  Tiffany came to me for help arranging a little payback and the return of the money, and when I saw Janine I knew exactly what to do.  I did some research and found out we know some of the same people, so I left a note suggesting she find me at the marina.  I explained that I was a friend of a friend and that I might have some work for her with a wealthy guy in the marina named Bill.  She showed up here to meet me, but met Bill instead."

Janine's grunts sped up and grew in intensity as Bill obviously approached his orgasm.  Bill's cum  must have been very good because he groaned loudly as he came in the blond's well used asshole.

After a few beats, Don broke the spell and said, "Let's get those groceries unloaded on Bill's boat."

***

Tiffany stayed on Charlie's boat for about four days.  They were obviously having sex, but in contrast to Bill and Janine, they seemed happy and light as they emerged for dinner and drinks with Don and Maggie.  They even spent a couple of evenings playing cards at Maggie's nightly party, though they would wrap it up early and head back to Charlie's for bed.  Many times they sat on Don's boat and had cocktails while listening to Bill brutally use the pretty blond in next boat over.  Don quickly realized that Tiffany took a perverse pleasure from the girl's use, and often she and Charlie would leave in a hurry after Bill came, presumably to relieve the sexual pressure built by the rough pairing of the couple next door.

Janine had eventually started to emerge from Bill's boat.  Bill got her an incredibly skimpy bikini from somewhere, and it was almost all she wore when they were on his boat.  The red bikini left nothing to the imagination, with her lovely tits almost spilling out of the top's small cups and her plump asscheeks framed by the thong string stretching across her frequently used asshole.  The thong obviously got Bill hard, because Don couldn't guess how many times he watched Bill lead Janine in his boat, lean her against a bulkhead, and pull her thong to the side so he could slide in her asshole.  After he emptied himself in her guts, Bill would pull her thong back in place and lead her back out on deck.  She usually looked at Don as she emerged still panting from her buttfuck, obviously embarrassed to be treated like a fucktoy in front of Don.  The gorgeous blond definitely looked worn out, and from what he saw and heard Bill was still fucking the girl three to four times a day.  From the deck of his boat, Don could see the bruises and hickeys in various places on the girl's lovely body.  Bill used her whenever he wanted in any way that pleased him.  The girl seemed to have had all the resistance fucked out of her and simply did what Bill wanted.  

At about 10 am, a week or so after Janine shacked up with Bill, Charlie and Tiffany emerged, smiling and happy, with her luggage.  Her revenge vacation was over, and it was time to head home.  After her bags were in the car, they stopped by to say goodbye to Don.

Don was enjoying the quiet, sunny morning and was reading a book when they arrived.

"You headed home?" Don asked politely.

Tiffany brightly answered, "Yep, all things must pass."

"Did you get the money back?"

Charlie spoke up, "I went over to Bill's yesterday and he had Janine give me her account info.  We got Tiffany's money back plus a nice amount Janine must have stolen from other men."

Don realized he must have been at Maggie party at the time, so he didn't notice Charlie's visit.  Tiffany asked if she could use the head on Don's boat since they already locked up Charlie's boat.  Don said sure and moved aside.

While Tiffany was inside, Charlie leaned close to Don and said quietly, "Bill had her suck me off while I was there.  She didn't say a word, just knelt down, pulled my cock out, and started sucking.  She was in that slutty bathing suit, so he pulled the string to the side and started fucking her and wanted me to stay so we could fuck her together, but I knew Tiff would get worried so I just let her swallow my load.  I talked to Maggie about it later and she told me Bill made Janine eat her out a couple of days ago!  She said it was wild and she actually went back later in the day for another session!  You ought to stop by, I bet he'll have her fuck you.  I think he loved exerting the control over her.  I know I wouldn't mind a session in her sweet ass after Bill has been tenderizing it for a week."

At that point, Tiffany emerged from the Don's boat, and Charlie said in a normal tone, "Anyways, think about it.  Seems like a decent proposal in my opinion." 

After she emerged, they chatted a bit about Tiffany's travel plans until the calm morning air was split by the sound of a brutal slap and Bill saying roughly, "Don't argue with me, open your mouth bitch.  I have to piss and don't want to get up."

The sound of the exchange leaked very cleanly from the open porthole on Bill's boat.  They stood in silence and listened, then heard Bill say in a kind voice, "Good girl.  Just think about all the nice things I do for you baby and keep swallowing.  Don't spill it!  Pinch my cock if you need to stop the flow to swallow."

The three stood in complete and shocked silence until Bill said, "Good job, baby, I feel much better.  Now suck me hard, then lube me up, I'm gonna let you ride my cock with your sweet asshole.  Remember how tight it was when we started?  Baby, that hole is nice and broken in now, just how I like it.  I can't believe you hadn't been buttfucked when I found you.  I fixed that and helped you catch up for years of missed opportunities!"  Bill chuckled as he said the last sentence.

There was a brief pause, presumably as Janine lubed Bill so he could use her guts for his pleasure again.  Then the sound of slapping hips emerged from the porthole, and the three stood there in silence imagining the beautiful blond crouching over Bill fucking her formerly tight hole down around his cock hard enough to make a loud slapping noise.

They looked at each other for a second, then Tiffany blushed a bit and said, "On the other hand, maybe I'll stay for another day or two and soak up the atmosphere  a bit more.  How about some mimosas on your deck?"

Don smiled knowingly, then said, "Great idea!"

They settled on to the seats on Don's deck and drank mimosas while listening to the pretty blond roughly abuse her own asshole to please the man who broke her.