Pirates On The Caribbean

Jamaica has a reputation.

Mature women are aware of the reputation.

It is well known that Jamaica is a girls trip destination spot for wealthy mature women that want to indulge themselves with a weekend of big black cock and get randomly fucked in total anonymity with no strings attached.

There are resorts in Jamaica that specialize in this type of adventure for mature women with high sex drives. These resorts are promoted as milf vacations.

Small groups of American mature housewives will come to Jamaica together to vacation and party and have as much anonymous, mind blowing sex as they can stand. They come to Jamaica to be ravished by big black cock.

My mature milf wife, and four of her milf girlfriends, are well aware of this reputation. All us husbands are also aware of this taboo reputation.

However, none of us were aware that pirates with a passion for mature American milf pussy actually existed. We would soon find out otherwise.

Many times our wives would talk and laugh with us husbands about taking a girls trip to Jamaica to experience as much big black cock as they could handle. It was all just fun conversation until we decided to call their bluff. However, we had one stipulation. They had to take us with them.

We wanted to go with them to help turn our wealthy mature wives into total black cock sluts. We also wanted to watch. We had an evil plan to make sure thay had all the big black cock they could handle.

All the wives are pure milf trophy wives each having at least one child. Pure milf material. All around 45 years old with well maintained bodies. Total prick teasers with high sex drives.

These mature milfs always drive our college age son and his friends crazy at our adult pool parties. I know for a fact my wife has been banged by at least one of our son's buddies. I also know my son has banged one of the wives.

The four wives all workout together at least four times a week with black personal trainers at the same gym. The wives seem to get turned on by their black trainers. They always come home after their workouts horny as hell ready for cock. We think their black trainers have created their desire for big black cock.

My wife is a redhead. Two of the wives are blonde twin sisters both over 6 feet tall with long tan legs. Both played volleyball in college. One wife is an attractive brunette who was a gymnast back in college. She still maintains a stretching routine which keeps her extremely flexible.

At one of our pool parties she was bragging about her youthful flexibility. After she had a couple drinks one of the college guys challenged her that she could not cross her ankles behind her head. We were all wondering if she would actually try to do it in front of the entire party group. We cheered her on.

That nasty college boy lost the bet but he really just wanted to see her mature camel toe with her legs spread wide open. We all did. My son told me that later that night the same guy took her into his bedroom and licked out her mature milf pussy to multiple orgasms while she was in the same position.

The fourth wife is a stunning black woman. She is into the housewives of Atlanta look and style with long eyelashes, long fingernails, and slender waist with huge 38 DD tits.

My buddies and I have had many conversations about swapping and fucking all of each others wives but we are not ready to go there. At least not yet.

Unknown to the wives, all of us husbands have many screenshots of them sucking our cocks or getting fucked that the husbands share with each other. My favorite is the black wife. She has huge hanging tits and I love the contrast of her spread pink pussy lips against her black skin. Pink never looked so good. She loves to suck her own nipples when she orgasms.

If we couldn't actually fuck each others wives, the next best thing would be to watch all of them get fucked by big black cock. Either willing or unwilling. We had an evil plan to make sure that happened.

We all decided a Jamaican vacation was in order. Two of us husbands are experienced sailors so we decided to spend a couple days in Jamaica at a resort and then rent a forty foot sailboat and spend a couple nights on the water. Our plan was starting to come together.

The Jamaican resort was fantastic. The pool atmosphere was great with an incredible variety of mature women all wearing very revealing swimsuits, including our wives. Many of these mature women were there to get their mature pussies stretched by big black cock.

All of our wives were getting a lot of attention and offers from the Jamaican pool waiters and bartenders. These guys were not shy about wanting to fuck our wives. We let them know that our wives were available. They would get their chance.

On the second night we had a great dinner at the resort. The waiter let us know that he and some of his friends were going to the resort dance club later and invited us to join them.

I could tell that our waiter really wanted to treat my red headed wife to his big black cock. We finished dinner then we all headed to the resort dance club. All the husbands agreed that we would watch our wives get fucked by black cock that night.

The dance club was wild. Lots of reggae music and lots of touching on the dance floor. All of our wives were very popular on the dance floor. They were grinding up against black cocks all night on the dance floor.

Our wives were being total prick teasers. We weren't sure if these Jamaican studs were going to take no for an answer. They wanted our wive's mature pussies. The wives didn't know it yet but they were all about to experience their first Jamaican big black cock tonight. My wife would experience more that one.

All our wives had their tits and asses grabbed and squeezed on the dance floor all night long. I noticed that my wife's panties were partially hanging out of our waiter's shirt pocket. She had given her panties to him after dinner as an extra tip and also an invitation.

It was now closing time. I invited our dinner waiter back to our room for a drink. He asked me if two of his buddies could join us. I looked at my wife for approval. She nodded her approval.

My 42 year old mature red headed milf wife was going to get a big black cock workout. I noticed that all the other couples had also left with at least one black guy. Each of the black guys also had a pair of mature milf wife panties hanging from their pockets.

It appeared to be a badge of honor for these guys and also a message to their buddies that they were going to get some mature pussy tonight. It was also a clear message that our mature milf housewives were going to experience some big black cock.

When we got to the room, I poured myself a drink and took a seat.

These guys didn't waste any time. They sensed a woman in heat and they were going to have her.

They crowded around my wife and stripped her dress off of her. They started kissing and feeling her all over. They started licking her perfumed sweat off her body from her head, down to her pussy, and down to her toes. One guy went behind her and licked all her sweet tasting sweat from between her ass cheeks.

They all had fingered her pussy on the dance floor. Her aroma was still on their fingers.

One guy dropped to his knees and starting tongue banging her shaved pussy while she was still standing. Another guy was on one knee with his face in her ass rimming her pink mature asshole. They were getting her three holes ready.

They all stepped back, took off their shirts and dropped their pants. Their black cocks were huge and they weren't even fully erect yet. My wife got her first look at the three monster black cocks that were going to stretch all three of her holes to the maximum. Both she and I said,

"Holy Shit."

My wife had the three biggest cocks she had ever seen right in her face. They said,

"Get to work bitch." She sucked on all three of their cocks until they were totally rock hard. I am well hung but I am not even in their league. The waiter asked her,

"Lady, do you like airtight?"

She said, "I don't know what that means!" All three of them laughed out loud. She was about to find out.

Our waiter layed on his back on the bed and said,

"Sit on my cock woman and spread your lovely white ass cheeks."

She was in pain trying to fit his black pipe into her tight pink mature milf pussy. He didn't care. He kept thrusting into her ginger pussy until he was balls deep.

Player number two covered his cock with hand lotion and got into position and shoved his middle finger up my wife's virgin asshole to get her ready.

Player number three was squeezing his balls in his hand and was shoving them into my wife's mouth. She was giving him a ballwash.

Airtight was just about to happen. Ass man was getting ready.

Ass man stood on the bed, took one more squirt of lotion on his big black cock and placed the head of his cock on her pink asshole as a warning to my wife to let her know what was going to happen next.

He slowly worked his black cock into her pink reluctant asshole. She squealed like a high school virgin. All three big black cocks were now balls deep in my wife's pussy, mouth and asshole. They were all working my trophy wife really hard. She was sweating like a goat. It was both pleasure and pain at the same time for my slut wife.

They stopped and switched positions a couple of times so that eventually all three Jamaican men had fucked her pussy, mouth and asshole.

They all decided to finish by standing over her on the bed and glazing her face with Jamaican jizz. I also added my load to her lovely face. My wife was exhausted but totally satisfied. She fell asleep.

She didn't know it at the time, but she would be seeing these men, and many of their friends, one more time on our vacation. She had one day for her three holes to recover.

I later found out from the husbands that all the other wives had a similar black cock experience that night. The vacation was just getting started for these mature milf wives. Their mature milf pussies, assholes and mouths would soon be gobbling up more big black cock.

In the morning we would head out to sea.

Spending time on the sailboat on the water was fantastic. Lots of fun, sun, music and alcohol. We all got to see all the wives naked bodies since they really enjoyed skinny dipping.

We all agreed to not have sex with our wives to let their bodies recover for the next round of black cock punishment that we all knew was coming. The ladies had no idea there was going to be a second round.

We were getting low on supplies so the husbands took a harbor shuttle to shore to grab more food and drinks. While heading to shore we passed an ominous looking boat heading out to sea. The boat was flying a skull and crossbones pirate flag and carrying a large group of black Jamaican men drinking from bottles of rum.

We asked our captain about them and he just laughed and said,

"Pirates."

We all just laughed. Pirates were not a real thing. We would later find out that pirates are definitely for real. Especially in the open waters of the Caribbean. We had an evil plan.

After about an hour on land we headed back out to our boat with supplies. As we started to get closer to our boat, we noticed that the pirate ship we had seen earlier appeared to be tied up to our boat. The women all appeared to be tied together back to back. We told our captain we needed to quickly get back onboard our boat.

The captain dropped us off and he immediately took off like a bat out of hell. As we boarded our boat, all the Jamaican pirates were sitting around laughing and passing around bottles of rum they had taken from our stash that we had on board. They said,

"We have been waiting for you motherfuckers. We like your women. We want your women. We will have all your women and you will watch motherfuckers."

They all started hooting and hollering and chanting pirate shit.

All the women recognized the pirates. They were all from the resort the other night.

All the husbands figured that these guys had fucked so much mature tourist milf pussy over the years they were pretty much addicted to milf housewife pussy. Mature pussy was like heroin to them. They had to have it one way or the other. They were going to get some today.

They had come back for round two with our women. They all wanted to fuck each and every one of our women. They wanted us to watch them fuck our women adding to their excitement.

Our wives were about to get a workout. There was a lot of big black cock onboard the boat that needed to release some fury.

We almost felt sorry for our wives. Almost.

They tied us up back to back similar to what they had done with the women. They made us all take a huge swig of our own rum. They also made each of the wives take two gulps of rum. It was now party time.

They decided it would be more fun to use their knives to cut off the ladies swimsuits. Five pirates stood in front of the women, and put their knives up to their pretty faces to frighten them. They wanted the wives to see the sharp, shinny knife blades.

The blades were then placed under the strip of bikini material between their tits. With one quick upward motion, all their milf tits were now hanging and glistening in the sun. The pirates swung the bikini tops over their heads hollering in celebration.

The pirates made it a point to pinch all their mature nipples between their thumb and index fingers until all the women had tears rolling down their cheeks. They wanted to make sure that our mature milf wives knew who was in charge.

They yanked the strings on the women's bikini bottoms, pulled them out from between their thighs, and also twirled the bikini bottoms over their heads in celebration. Total pirate scoundrels.

The wives could now feel the cool sea breeze on their mature totally shaved milf pussies. The pirates wanted to have a little pirate fun with their captive women before they plundered all their holes with their cocks.

Five pirates laid our naked wives over their laps and started spanking their tender asses with their open palms. The sound of their hands smacking soft mature milf ass was amazing. The wives were screaming and shrieking with every slap. I thought I was going to blow my load in my pants.

They next tied the women's hands together and told them to raise them over their heads. Their hands were then tied to the ropes that raise the sails on the boat. There were five ropes. One of each wife. The command was given,

"Raise the sails." Two men on each rope pulled with all their might and up went our five totally naked wives. We could not believe what we were seeing. They were all hanging probably 20 feet over the water, twisting in the wind with their pussies exposed, their tits bouncing and legs kicking.

The screams and shrieks from the women were exhilarating making the pirates aroused and more aggressive. All the pirates were laughing, cheering and hollering while gulping down more rum.

All the husbands were getting rock hard watching the five naked mature milf slut wives swaying in the ocean breeze like mature milf pussy flags.

A couple other boats even passed close by and honked their horns in approval of seeing five naked mature women with red asses swinging from our ship's main mast. Apparently people love pirate shit.

A couple of us husbands even had to hold back our laughter. It was a sight none of us will ever forget. It was about to get better.

After a couple minutes the pirates lowered our milf wives back down to the deck. They made each woman take swig of rum to get them ready for what was coming next.

It was now time for the pirates to select their women.

The twin blonde sister wives were very popular. A couple groups of pirates were fighting over them. They had never fucked a pair of twin mature white milfs. They would get their chance.

The black wife was also very popular. She had the biggest tits of all the wives. Her nice pair of firm 38 DD hooters were just begging to be squeezed.

The pirates had obviously fucked a lot of black Jamaican women, but they had never fucked a mature American milf trophy black woman. They were going to pound her pink pussy without mercy. Her husband was in for quite a show.

My red headed wife was also a hit. Redheads are rare in Jamaica. They almost carry a goddess like status. Every black man wants to fuck a redheaded ginger mature milf pussy.

The brunette wife was rock solid. The pirates knew she was a former gymnast. She earned her reputation for being very flexible from her night at the resort.

Apparently her pussy was eaten out while doing the splits on the men's faces. She also did the splits while getting fucked on their black cocks. Now all the pirates wanted to see just how flexible she was. Time for more pirate fun.

They tied a rope to each of her ankles and wrists. Again came the command,

"Raise the sail." She was being lifted again. When she was about 5 feet off the ground and totally spread eagled the pirate leader said, "Stop, I have an idea for our flexible wench."

He picked up a bottle of rum, finished it off, and walked over to the spread eagled mature white milf. Her mature pussy was level with his face. He started licking her pink pussy to get it wet. He then licked the neck of the rum bottle.

He then inserted the neck of the empty rum bottle up into her mature tight gymnast pussy. He told her,

"Don't you dare let that bottle drop bitch,"

She tightened up her pink snapper as the pirates continued to pull on the ropes and raise her up with an empty bottle of rum hanging from her pussy. They pulled tighter on the ropes tied around her ankles until she was doing full splits hanging in the air. All the pirates were laughing and cheering.

They raised her to about 20 feet and let her hang there as if she was their pirate symbol of victory. They let her hang there until her pussy could no longer hang onto the bottle of rum. The bottle of rum splashed into the blue Caribbean water.

They lowered her back onto the deck. She was exhausted.

Since she was so flexible the pirates would eventually tie her ankles together behind her head as she had done at our pool party. Every pirate would fuck her pussy, ass and mouth. Apparently pirates like to have fun with flexible white mature brunette women.

There were three pirates on each woman. Two pirates would hold each of their arms while the other pirate worked on her pussy and asshole to get both holes wet and lubed up.

One pirate would then pick a wife up in his arms and impale her mature pussy on his big black cock. The second pirate would then slip in behind and do the same to her pink mature asshole, double penetration style.

At one point all five wives were bouncing around moaning and shrieking on two big black cocks balls deep in their milf ass and pussy.

The men would then switch positions so that all three pirates got to fuck each wife's mature pussy, ass and throat. We figured that each woman would experience three big black cocks and it would then be over.

Then something happened that we did not expect.

The men traded women. All five wives were going to be fucked by each group of three black cock pirates. We looked at each other and said,

"Holy Shit."

All five captured American milf wenches were passed around and double penetrated to exhaustion. The pirates where hooting and hollering having found their best booty treasure ever.

To finish things off, all the women were then forced to get on their knees and suck off the pirates for a final group facial cumblast.

After it was all said and done each mature milf wife had fifteen big black cocks in their pussy, up their ass, and in their throats. We figured that would satisfy their desire for black cock. At least for a while.