Wild Bill 2: Helping Out A New Friend

It was a cool South Florida morning in the early part of the year.  It was one of those great spring days, it was Sunday, and they knew summer would be coming soon.  That morning, Charlie and Don had gone for a walk in the park and come back to the marina.

As they walked back into their section of the marina, a familiar sound greeted them.  The sound of slapping hips and grunting.

"Fuck back harder bitch, push it all the way in your guts."  Bill's voice echoed out of his porthole.

Don, Charlie, and Maggie all agreed that Bill got off on the performance aspect of abusing Janine so they could all hear.

Janine's grunt turned into a loud moan of pain as she presumably impaled herself even deeper on Bill's large cock.

"Now bounce against me, but keep pushing back.  We need to train your hole to take my cock all the way." The hip slapping resumed, but the lovely blonde's grunts took on a distinctly pained tone when she bottomed out.

"That's it baby, we'll train your fuckhole yet."

She groaned out, "Please fuck my pussy, my asshole is so sore from last night..."

"Maybe later baby.  This feels too good to stop."

Don made a pitcher of bloody marys, and then he and Charlie settled onto the deck of Don's boat to enjoy the show.

Don quietly said, "It's early enough that I bet they just started."  He chuckled and said, "Sounds like Janine is in for a long and painful morning."

Charlie also chuckled and took a drink of his cocktail.

"I know it hurts baby, but it feels good for me.   Keep fucking back."

Apparently Janine complied, because the only immediate response was the sound of Bill slapping her ass and saying, "That's right baby, milk my cock."

The men sat there for a few minutes basking in the morning sun and enjoying the show when Maggie wandered over to Don's boat.  Maggie was a short, thick Jewish brunette in her late forties, so she was a stark contrast from the pretty blond with the sore asshole currently in Bill's bed.  She looked cute this morning in some tiny and tight blue shorts and a yellow tank top and with her long curly dark hair in a pony tail.  Wordlessly, she climbed on board and poured a  cocktail.  She took a sip, and then all three sat there listening.

"Please, PLEASE fuck my pussy.  I'm so sore from last night!"

"Maybe after I cum baby, but no promises.  This fuckhole just feels so good baby."

After a few more minutes, Maggie finished her drink and surprised the men by saying, "goddammit, I'm going over there,"  after which she stood and walked to Bill's boat.

She knocked on the hatch and said loud enough for everyone to hear, "Bill, it's Maggie, I'd like to join in."

The grunting stopped, and the men watched as the door opened and Bill invited Maggie inside.

"Shuck those shorts and sit back against the wall.  Janine-baby, show Maggie what you can do with that mouth."

The men heard Maggie moan in pleasure as Janine starting sucking on her pussy, then they heard the painful grunting start again as Bill fed himself back into the lovely blond's asshole.  Now the grunts had a different sound because her mouth was muffled by another woman's pussy.

Thick with lust, "God, I love the way it feels when she grunts into my pussy.  Fuck her harder!"

Obviously, Bill was happy to comply because the slapping got louder and the grunting became more urgent.  Maggie moaned enough that it sounded like she came once or twice on the younger woman's tongue.

They finished the bloody mary pitcher and Don went inside to make another.  

Charlie heard Bill say, "Maggie, get on your knees so I can fuck you.  Janine get under her and suck her clit.  Make her cum again."

Don came back out as they were reorganizing, and Charlie said quietly, "He's about to fuck Maggie!"  They both poured drinks and waited for the show to begin.

Maggie said, "Aren't you going to wash off first, UGH!"  as Bill took her with the fat cock he just pulled from deep in Janine's asshole.  The familiar sound of slapping hips filled the air, though this time accompanied by Maggie's guttural noises.  They both immediately realized Bill was in her pussy, because she was obviously enjoying it.  It was a bit weird to listen to a woman they considered a "pal" having her pussy smashed in by Bill, by it was still very hot.  It was obviously that Janine's mouth was working overtime on Maggie's clit, because they could hear Maggie coming within a couple of minutes.  After she came, Bill slowed a bit but kept at her, gradually riding her thru three more cums before she begged him to stop.  

They heard him gently slap Maggie on her ass, then he said, "Sure baby, take a breather while Janine sucks me off."

The sounds pretty much died off at that point, but they still heard the occasional choking sound as Bill forced his cock into the lovely blonde's throat.

"I love it when you suck another woman's juice off my cock.  You are such a filthy girl.  Now bend over and let's get back to that buttfuck."  They heard Janine groan in desperation, and the hip slapping and painful grunting resumed.  Maggie exited from the hatch of Bill's boat, looking like she just got roughly fucked.

She walked over to Don's boat, poured herself a bloody mary, then settled in to one of Don's deck seats.  

They say in silence for a minute or two and listened to Janine's resumed buttfuck.  Finally, Maggie simply said, "That hit the spot" with deep satisfaction in her voice.

***

It was always a bit awkward when Janine came over to the neighbor's boats.  She had sucked off Charlie and had sex with Maggie twice, and she knew that Don heard every moment of her abuse.  They all tried to act like there was nothing unusual going on, but everyone knew the truth.

It was a few days after Maggie screwed Bill and Janine that Bill upped the ante.  They were all at Maggie's ongoing party when a college basketball team showed up.  The party progressed as usual for a while, but then Bill, Janine, and two huge basketball players headed towards Bill's yacht.  Don and Charlie and Maggie all made eye contact and smiled as they realized that Janice was about to be destroyed by those huge black guys.  

The party slowed down a few hours after midnight.  Charlie peeled off early with a chubby and giggly brunette in the Keys on vacation with her girlfriends.  They went back to his boat for a bit of fun before she went back to her husband.  Maggie was dancing with one of the basketball players.

Don was drunk and had enough and was ready for bed.  As he stumbled across the lot to his slip, the sounds of Maggie's party gradually faded, and the sounds coming from Bill's boat faded in.  

"OH, OH, OH, OH..." chanted out of the yacht.

Don smiled as he drunkenly remembered Janice and basketball players.  He heard Bill say, "You like those huge cocks, baby?  Have you ever had such big ones?  Now that I think about it, have you even been fucked in your pussy and ass at the same time?"

She made some gutteral sound Don couldn't make out.

"Well, baby, you picked two huge cocks for your first double fuck."

She just continued her "OH, OH, OH, OH..." mantra as the two young men that Bill picked tore into her.

As Don climbed on his boat, he sat for a few minutes to listen.

The little blond kept making gutteral noises until one of the basketball players said, "Fuck man, I need a drink!" and then Bill said, "Go grab a beer."

Janine's grunting subsided a bit, then Don heard Bill chuckle and say, "Goddamn, baby, your asshole is so loose!  If you didn't have a big cock in your pussy I'd be falling out!  You might need to wear a diaper after this one."

The girls grunting continued for a few minutes, then Bill said, "Let me get out of the way so you can get back in her ass, she can suck me clean."  A second or two later her grunts with muffled by the cock in her mouth.  

Don listened for a few more minutes, then decided he needed sleep and climbed into his bunk.  He could still barely hear the sounds from Bill's boat as he drifted off to sleep.

***

A couple of weeks later, Stephen and Emma showed up at Maggie's ongoing yacht party.

Don immediately recognized Stephen as a tech billionaire, and Emma was his stunning wife.  They'd married several years back, and she was obviously a former model turned trophy wife.  She was a tall, exotic looking latina with fake tits and a generous ass, and she was strikingly beautiful.  She was also a bitch.  

The marina folks immediately realized she was very aloof and couldn't be civil to any of them.  She was more pleasant to some of the pretty young people who showed up to party, apparently because they were almost as attractive as she was.  Don noticed Stephen's frustration with his wife's bitchiness.  He also noticed that Stephen and Bill became fast friends.  They'd find seats in the corner and talk about god knows what while their women danced.  For the better part of a week, Stephen and Emma came over every night for several hours, and for most of the night Bill and Stephen bonded.  

Later in the week, they had a poker game that changed everything.  It was late in the evening before the party really got going, and Bill had been winning easily most of the night.  Finally, Stephen though he had a hand strong enough and he bet everything against Bill.  Bill met his challenge and added a few days with Janine to the pot.  Janine turned beet red and there was a shocked silence among the partygoers, as most of them had no idea about Bill and Janine's relationship.  After a few heartbeats, Stephen offered a few days with Emma to the pot, and they showed their cards.

Bill won.

***

Bill and Janine left with Emma, who seemed so shocked she couldn't speak.  Stephen started chatting with Maggie, and after a short time Don noticed them heading back toward Maggie's cabin.

When Don later stumbled back to his boat, he knew what to expect, and he wasn't disappointed.

"OH GOD, PLEASE STOP!" echoed across the marina.  

When Don got back to his boat, he saw that Bill hadn't even made it back to his cabin.  He was in the galley of his yacht, which, due to its large windows, offered Don a nice view of the action.  

The lovely and statuesque latina was belt over the counter in his galley with her party dress around her waist and her red panties falling down her legs, and Bill was furiously pumping his fat cock into her while Janine knelt behind him trying to tongue his balls out the outstroke.

In a drunken haze, Don slumped onto one of his deck seats to watch as the beautiful woman was defiled.  He realized that she had no idea how terribly she was about to be ravaged by Bill's indefatigable cock.

He sat there listening to the lovely latina beg for mercy for several minutes before he decided he was too drunk and needed sleep.  Her cries of anguish leaked feebly into Don's cabin as he fell into a deep sleep.

***

A few hours later, Don awoke to the sound of rhythmic slapping.  His booze and sleep addled mind initially thought it was waves against the boat.  After several seconds he heard the grunting and realized Bill was at it again.

He heard a loud crack as Bill presumably slapped Emma's ass, and he definitely recognized her voice as she squealed in pain from the slap.

Don heard Bill say, "Fuck that skinny ass back on me, bitch" as the rhythmic slapping lulled him back to sleep.

***

For the next few days, the dynamic around the marina changed only a bit.  Instead of Janine grunting in pain and begging for mercy, it was mostly Emma.  From what Don could tell, Janine mostly used her mouth to lube Bill's cock or Emma's holes, which Don suspected was a welcome break for her.

Stephen spent a couple of days on Maggie's yacht fucking her intermittently.  He left to wrap up some business in Miami.  

***

Bill gradually fucked Emma into submission.  The resistance faded and she accepted his rough treatment.  After a few days, he sent Janine over to Don's boat.  She knocked on his hatch, and Don was surprised to see her.  She was dressed in a pair of tiny and tight white shorts and a tube top with red high heels that matched her top and left almost nothing to his imagination.

"Because he has another... girl, Bill wants me to...stay here."  Don smiled when he noticed she had a half full bottle of lube in her hand.  Bill was such a thoughtful guy.

Don paused for beat, then said, "Sure, darlin', come on in.  Hand me that bottle."

She looked sheepish as Bill's one friend who had not had sex with her took the lube from her hand and helped her down into his cabin.  "My bunk is at the front of the boat."  

Then he said, "Wait - go ahead and lube yourself up while I take a piss," and handed the lube back to her.

The lovely little blond walked back to the unfamiliar bunk, then peeled her tight shorts off and lubed her holes while looking back at Don with a slightly fearful look on her face.  

Don left the door open while he pissed, then he walked in his berth and said, "On your hands and knees, baby.  I've heard Bill talk about your asshole for a while, and I think it's time to try it out."

Janine rolled onto her knees, then pressed her chest to the bed and used both hands to pull her asscheeks apart, showing Don her obviously well fucked asshole.  She'd shucked her tiny shorts but kept on the tiny thong underwear, and the string of the thong only made her loose asshole even more obscene, since the string completely failed to cover the apparently permanent gape caused by regular buttfucks.

Don pulled her thong to the side, pulled his cock out and slid it around on Janine's slippery asshole and pussy to transfer some of the lube to his cock.  He noticed Bill preferred silicone lube, which made sense because it never really dried out.  It was perfect for a guy whose dick never got self, he could just keep fucking.

He slowly but firmly pushed into Janine's hole, a bit surprised at how loose she was but delighted at the sensations caused by her hot, wet sheathe.

He fucked her for a while gradually increasing his pace until he finally said, "Squeeze your asshole while I cum in you," and then emptied his balls into the beautiful girl's clenching asshole.  He later realized that didn't once even consider her pleasure during that first fuck.  

After he caught his breath, He said, "Suck me clean, baby" and without a word she climbed off the bed and swallowed his half-hard cock to the root.  As she tongued him, he took a big drink of beer and realized he needed to piss again.  He didn't bother to tell Janine; he just relaxed his muscles and let the piss flow into her gently sucking mouth.  

Without any visible reaction, she just started swallowing his piss.  When he was done, she sucked out the last few drops and then set to the task of getting him hard again.

As he looked down at the beautiful blonde currently sucking him who had just drank a bladderful of his piss without a second's hesitation, he felt himself rapidly hardening and wondering how long Bill would loan her out.

***

A week later Stephen texted Maggie to tell her he had to go back to Austin to manage a crisis, and he sent a plane ticket for Emma to fly back.  In an unfortunate mishap, Stephen had taken Emma's phone when he left, so he could only communicate with her thru the denizens of the marina.

However, the night before Stephen sent the ticket, Bill and Emma had been over at Maggie's party, and Bill told Charlie he was taking Emma down to Key West.  Emma had been a hit at the party because Bill had her dressed in one of Janine's tiny bikinis that was actually a bit too small for the tall Latina, and both the male and female party-goers were distracted by the beautiful dark skinned girl in the scandalous thong bikini.  Janine and Don sat in the corner and watched the spectacle until Don whispered in her ear, "Let's go back to my boat," and Janine nodded knowing Don would use her to empty his balls again.

After they left, Bill and a random party-goer had gotten into some good natured competition and ended up tossing a coin to see which one would get a blow job from the other's woman.  Emma ended up kneeling in front of the entire party and fishing out the stranger's cock so she could suck him off in front of everyone.  The beautiful latina in the obscenely tiny bikini did such a great job that Bill had her suck off three other guys just for the entertainment value of watching her tits and ass jiggle as she worked the men's cocks.

Later that night, Don listened as Bill used Emma.

"You're such a whore; I can't believe you're so filthy.  Sucking off all those strange men in front of a crowd.  What would Stephen think?"  Gagging noises accompanied Bill's words, and the same throat that earlier stroked four other men until they came was wrapped tightly around Bill.

Don dozed off, but woke in the middle of the night and emerged onto his deck for some fresh air, only to hear female grunting and slapping hips.  

"It was obvious that Stephen didn't fuck your asshole much, but in the last few days it's loosened up nicely.  Your deepthroating has gotten much better, too.  You've got three world class fuckholes now, baby, and I'm glad I got to enjoy them as much as possible during the time we had together.  But this too shall pass." 

The woman was silent besides her grunting, which was in tempo with the slapping sound.  Don listened and the grunting gradually got faster and louder as Bill approached his orgasm.  

Don realized he needed some relief, so he climbed down into his boat and woke up Janine.  She didn't seem thrilled about it, but she followed him out and after Don sat down, she knelt down between his legs and sucked him into her mouth.  Don closed his eyes and listened to Emma's assfuck while Janine slupted oh him.

However, Bill stopped.

"Baby, we're leaving in the morning for the Keys, so I want to try some different things before I drop you off.  Hand me that lube then lay on your back."

A few seconds later, Emma made a weird grunting noise, and Bill said, "I know you've never been fisted, baby.  You are too tight for that.  So I'm gonna broaden your horizons a bit."

With his eyes closed as Janine mouthed his rigid cock, Don could almost picture Bill's rough hand pushing relentlessly into Emma's soft and still fairly tight cunt.  From the sounds she made, Don could tell that Bill was pushing his fingers into the poor gal, fucking her with most of his hand.  Her discomfort was obvious, and became even more obvious when Bill added another finger.

"That's four baby, but the real trick isn't the fingers, it's the palm.  Once I get my palm in you, it's pretty easy to tuck in my thumb and slide my whole hand in your fuckhole."

The yelping noises grew in intensity over the next several minutes and Bill worked his hand in silence, then finally she cried out in pain as Bill obviously made progress in ruining the young's pussy.

Don thought his cock had never been harder as he and Janine listened to Bill hurt Emma.

The pained cries continued in tempo as Bill slid four fingers and his palm in and out of the trophy wife.  The rhythmic yelps stopped and turned into a continuous whine.

"Feel that, baby, you've almost got the whole thing in there.  I'm just gonna keep it in there and rotate it around a bit to stretch you out enough for my thumb."  The lovely brunette just made pained choking noises for the next several minutes as Bill systematically ruined her pussy enough to swallow his hand.  Finally, her grunting and moaning escalated and then climaxed with a squeal.  Bill simply said, "I knew you could take it baby.  The next time I fist you will be much easier."

Don listened to the woman's choked crying as Janine swallowed him and tried to make him cum.  Don grabbed a handful of her hair and roughly yanked her off his cock, then put his face next to hers and quietly asked, "Did Bill fist you?"  The lovely blonde whispered, "Yes" as they  listened to Bill teach Emma a new trick.

Still tightly gripping a handful of hair, Don pushed his tongue into her mouth and explored a bit while mauling one of her tits with his other hand.  Then he withdrew and they looked at each other for few seconds as they listened to Bill hurt Emma.  The Don quietly said, "Get in the bunk and lube your pussy, I'll be there in a minute."  Janine silently climbed inside the boat.  

Don sat and listened for a few more minutes as Bill found different ways to hurt the beautiful blonde trophy wife and used his entire hand to ruin her pussy.

Then Don got up and went inside.  He saw a bottle of lube on the counter.  He picked it up and  started lubing his hand as he walked toward his cabin.

***

By the time Stephen's text got to Maggie the next morning, Bill and Emma had sailed for Key West.  Bill came back about a week later, and Maggie gave him the message.  There was no way to contact Emma in Key West, so they simply moved on with their lives.  

Bill told Don some pretty funny stories about Emma.  During their week in the Keys, she'd become well acquainted with his hand.  He joked that by the time she went overboard, her pussy had taken the exact shape and size of his right hand.  He slid his cock in her pussy one time out of curiosity, but it was so loose he pulled it right back out and slid it in her much tighter asshole.

"The last couple of days I started fucking her asshole while my hand was in her pussy.  She didn't like it all, but, goddamn, jerking yourself off inside a woman is incredible."

***

Janine moved back to Bill's boat, though Don thought she was a bit sad to go.  But she was Bill's property, and Don was frankly thrilled that he got to spend a couple of weeks with a lovely young blond who would do anything he wanted.  Early on after she moved in, Don decided he was going to try to live like Bill while she was there.  He didn't have nearly the stamina or the resilience that Bill had, but he did every vile thing he could think of with the beautiful little blond.  She choked on his cock, she licked his asshole to get him hard, she drank his piss.  She had no limits, and Don enjoyed her while he could.  However, it became readily apparent that everything Don expected of her was simply not as bad as what Bill expected.  She did it all without pause, and the first hesitation Don saw was when Bill returned and Don sent her back.

She followed Wild Bill back to his boat, and a few minutes later her grunts and the sound of slapping hips filled the marina.  Don sunned himself on the deck of his boat, sipped his drink, and thought about the lovely blonde girl's very accommodating body as he listened to Bill reestablish his claim on her.  

***

A couple of weeks later, the police showed up.  Emma had disappeared very shortly after arriving in Key West.  It hit the national news for a few days, but the lack of leads led to a rapid loss of interest by the local police. 

***

Later that year, Stephen came back to the marina.  The marina gang issued condolences about his missing wife, and he seemed quietly sad about her disappearance.  When Bill said how sorry he was, Stephen hugged him, though Don thought it didn't seem like a sad hug.  He thought it was more of a congratulatory hug.   

That night, Bill and Stephen picked up a couple of attractive coeds from Maggie's party.  When Don stumbled back to his boat in the late hours, he initially heard a woman grunting, then heard her audibly cumming.  She said, "God, she's good at eating pussy.  So she's like your slave or something?"

Don heard Bill say something that he couldn't quite make out, then heard the gal say, "OOHH, I can't believe you're still hard!"

Don smiled to himself as he fell asleep to the sound of slapping hips.  That coed was in for a long night.