She Lost the Bet 8: Caribbean Good Times

by Jon Deets

Email Feedback | Forum Feedback

© Copyright 2012 - Jon Deets - Used by permission

Storycodes: M+/ff; D/s; bond; rope; kidnap; captive; chain; collar; bdsm; crop; shave; sex; oral; group; hum; voy; cuckold; cons/reluct; XX

(story continues from )

A Sequel to "Part 7"

Part 8: Caribbean Good Times

St. Thomas, US Virgin Islands. Warm trade winds, good rum, beautiful beaches and perfect vacations. My wife and I were recently there for Thanksgiving to celebrate my new job. We were tucked into our third rum drink at Mountaintop when suddenly she turned to me and asked, "Did the slave trade ever come through St. Thomas?"

"Oh yes", I replied, "all of these islands had slaves to work the sugar plantations. In fact, I think there was a big rebellion over on St. Johns."

"You are full of shit," my wife replied, "you just spout off answers thinking I will believe you!"

"Do you want to bet" I softly inquired?

This immediately slowed my wife down, but she was 3 deep into banana daiquiris and had the drunk courage going.

"Okay", she said, "if there really was a slave rebellion and you can name the year it occurred, then I will be your slave for the night."

I pretended to be deep in thought for a moment, and then ever-so-casually said, "well, I think it was in 1733".

One quick Google search later, and I was Master for the evening!

"How the hell did you know that?" my wife inquired?

"Because it was this day, November 23rd, in 1733 that is occurred, and they are having a re-enactment tonight. I saw an advertisement for it, so let's go watch" I responded.

That night we caught the ferry to St. John's and attended the re-enactment of the revolt, which was really very similar to an interesting Broadway play. Before the play began, a gentleman noticed my lovely wife and came over and whispered to us, "How about we include your wife in the slave auction?"

"Of course", I replied, "that would be funny".

"Sure" she replied, "always the actress!"

The play began with a slave auction, moved into the years of hard physical labor inherent to slavery, and then moved into the revolt of 1733. At about that time, the gentleman tapped my wife on the shoulder and she went backstage with him. The announcer then stated, "The Danish, English and French press didn't cover this aspect of history, but during the time the revolting slaves ruled the island for 7 months they actually auctioned off captured plantation owners as slaves".

With that, they paraded out 4 white individuals in leg-irons and handcuffs: 2 older men dressed as plantation owners and two women dressed in fancy dresses and one of whom, of course, was my wife.

"Bid it up, people, as all proceeds go to charity" the announcer shouted.

The play then commenced with a public auction for the "slaves" and to my surprise the bidding for my wife became quite spirited as she laughingly vamped it up a bit. Finally, a tall white man dressed as a Colonial-era doctor won the bidding and the "slaves" were marched back off-stage.

As the play ended, I decided to around the back of the stage to collect my wife. As I rounded the corner, I was jumped from behind and hit over the head and saw nothing but blackness. When I awoke, I realized that I was handcuffed and in the hold of a ship, and that it was moving. As I fought off my grogginess and motion sickness, I looked up and my wife was also in the hold and was chained up to the wall still in the handcuffs and leg-irons.

"What is the deal? Where are we" I asked.

My wife replied, "I don't know where we are going, but that man that won the bidding told me that he was glad I was his new slave and that he would see me soon".

Very soon the movement of the boat slowed and I heard the hull slide up on a beach. Soon, four men came down and grabbed us both and hustled us onto the deck of the boat and down a gangway. We were on a small, moonlit beach in a secluded cove and as I looked up I saw a large, imposing fortress-like home built of brick and coral. The men frog-marched us up and into the house, and down a flight of stairs into a basement. They immediately handcuffed me to an iron ring in one wall, and uncuffed my wife's wrists only to immediately tie her hands to a spreader bar and raise them above her head and attach the bar to a chain in the ceiling.

They then silently departed and very shortly thereafter the tall white man who had "purchased" my wife came down the stairs. He silently surveyed the room and then casually walked over to the wall and pulled a machete off of the wall. As he walked over to my wife she frantically attempted to move away from him, but the chains held her tight. With a quick flick of his wrist, the man inserted the tip of the machete under my wife's fancy dress and cut it from seam to seam such that it quickly fluttered to the floor. With two more quick movements her panties and bra were also on the floor and she was completely naked.

"My slaves remain naked until they have learned their place" he said quietly.

"That is enough" I yelled, "this has gone too far".

The man casually looked over at me and said, "Here is the way it is. During the slave revolt of 1733, the slaves allowed only 3 white people to live, the island's doctor and his 2 sons. For this re-enactment, I am the doctor, and my two best friends are the sons".

With that, two athletic looking guys came down the stairwell and stared at my wife lustily. The "doctor" continued, "Now I bought her at the auction fair and square as an act of kindness, but I tell you what. If you say so, I will stop this process immediately and take you both outside. What you will find is about 40 "slaves" continuing the re-enactment and they are in full revolt mode. They are very likely to kill you, and then go 40-on-1 on your wife until every one of her holes has been used dozens of times. You two choose".

My wife immediately gasped, "I will take my chances with you" and when the doctor looked over at me I wearily shook my head yes in agreement.

"I have taken the liberty of learning that your return flight is on 4 days," the man said. "In that time, I plan on training this woman, whom I shall call 'hussy' to become a perfect slave and if she pleases me, I will let you both return to your home".

With that, he turned back to my wife and began the first lesson by stating, "Never speak unless spoken to, never make eye contact, call me and my sons Master, and answer any question I ask with the words 'whatever master wishes'. Do you understand" he asked?

"Yes, I understand" my wife replied as she glanced at the doctor.

He slowly moved over to the wall and pulled down a nasty-looking riding crop, and turned and brought it sharply down on my wife's lovely ass. She yelped in pain and immediately teared up.

"What are commandments number 2 and 4" the man asked her?

My wife thought a minute and said, "Never make eye contact, and answer 'whatever Master wishes'" she softly said.

"And you broke both of those commandments, didn't you" he asked?

She silently nodded.

"What do you think your punishment should be?" he asked her.

After a slight hesitation she replied, "whatever Master wishes".

"Very good" he said, "you will only receive 10 lashes instead of the 50 I had planned".

With that, he gave her 9 more vigorous lashes with the riding crop as she jumped around and yelped. The two "sons" then came over and put an iron collar on my wife with a magnificent ancient lock, and attached a leash to the collar and brought her arms back down and hand-cuffed them in front of her. "Time to go outside" they said, and began moving her up the stairs.

The other men from the ship came downstairs and got me, and put leg-irons on me and moved me upstairs and outside. "The Master says you are to watch all aspects of her training so that you might learn something", one of them told me.

When I got outside I saw that they had tied my wife's wrists to an iron railing and had attached a spreader-bar to her ankle-irons such that she was spread wide open. "Quite a view" one of them said, as he glanced at both my wife's private parts and the moonlit bay beyond. With that, they each took turns fucking the daylights out of her for the next 40 minutes or so as the doctor watched impassively. They then took us both back downstairs and chained us to the wall.

The doctor said, "Its time for you to sleep as tomorrow is a big training day, but before you do would you like to give me a blow job?"

My wife looked down in misery and softly responded, "whatever Master wishes".

He pulled his large cock out of his pants and she gave him a vigorous blow job, and swallowed every drop of his cum.

The next three days were a blur of training, with my wife learning to instantly obey every order from the doctor and his sons which included "collect some firewood", "go unload the boat". "make me a rum drink" and "come over here and get on your knees so I can fuck you".

Of course, they had me observe every instant of the training. The first day she made several mistakes of not answering correctly or not responding quickly enough, and every time without fail she was tied-up to a whipping post and given a good whipping. The second day she only made two mistakes, and was punished for the first one by having her hair and eyebrows shaved and her eyelashes plucked such that she had no body hair whatsoever, and then was branded just above her pussy with a small "1733" brand; and for the second mistake she had her nipples pierced and two small pieces of eight attached via a small silver wire through the holes.

The wounds were dressed, of course, with rum poured on them.

By the third day my wife was an expert slave and instantly obeyed each and every order and pleased the three men with her ability to serve them as they desired. That last night, we all gathered in the great hall of the house, and a meal was served. The only thing missing was my wife, but after dinner a gong rang and immediately the 40 "natives" who had been at the re-enactment of the revolt filed into the hall with 20 seated on each side to allow for a runway in between them. The gong rang the 2nd time, and my wife marched in very slowly in all her naked glory, with no body hair, pierced nipples, and a submissive demeanor, and she stopped in the middle of the hall.

"Hussy" the doctor said, "you have learned well. I may let you and your husband go back to your home tomorrow. But first, one final test is required."

With that, he stood up from his chair and his sons also stood. He then said, "You have a choice. You can walk over to your husband and take off his handcuffs and leave with him. Or, you can walk over to my chair here to be handcuffed to each arm and on your knees with your pussy exposed, such that every man in this hall can fuck you."

After a dramatic pause, he said, "What is your choice?"

I saw my wife glance out of the corner of here eyes at me and start, ever so subtlety to begin to come towards me. She stopped suddenly, and with eyes firmly on the floor, she said, "whatever Master wants".

With that, a collective moan of disappointment came from the 40 men and a small smile played out on the doctor's face.

"Well-done" he said, "now go tie yourself down spread-eagle on my bed for one last night of pleasure for me. You will then be free to go tomorrow".

Again, I was chained to a chair in that bedroom as my wife tied herself down to be used by the doctor, and as he fucked her at least 5 times that night. Sometime in the night he told her that several women had failed the final exam, and that being fucked by 40 different men in a single evening was a fairly dramatic event.

In the morning, we were ferried over to St. Thomas fully clothed, and flew back to our home. My wife was complete surprised, and definitely flustered, when we had our first big company dinner and she saw that the "doctor" and his "sons" were the CEO and two executive team members of my new company. Hey, anything to get promoted! Plus, she has turned into an excellent slave for me.

19.06.12