Jill's adventure into slavery

Part 4 Jill’s adventure continues

“The Island Home”

Kelly delivered Jill to Manny at the boat docks and handed him the remote and keys to Jill’s belt.   They boarded the yacht and Jill watched as Manny started the motors and they left Cayman.  After about 2 hours Jill saw a small island in the distance and knew it was her new home.  They finally docked and before getting into the Jeep, Manny locked a set of manacles on both Jill’s hands and feet.  As they rode, Jill noticed the House at the top of a hill that was in the middle of the island and in the fields the drove passed she saw people that appeared to be naked working.  Jill asked Manny who they were and he told her they were convicts who had broken laws and were now serving their sentences here.  So there are laws and court her she asked.  Yes, this is a country, it has laws and there are lawyers from Cancun that serve as defense or prosecutor and Carmen is the countries magistrate, but all judges come from the “World Court” so trials are fair. All convicts wear control collars and the fields and their barracks are in the control zone and if they leave it they are shocked and an alarm goes off. 

They arrived at the mansion and got out of the jeep as Carmen greeted them and welcomed Jill to her new home.  Manny brought in the supplies from Cancun and went to see his wife.  Jill was lead down to the dungeon and shown her cell, where she would sleep if no one desired her to serve them at night.  It was an 8x10 foot cell with a cot, sink and toilet and a closet and dresser for her clothes.  Jill noticed the dungeon next to it was amazed at the size and the amount of equipment here.  Carmen then lead her upstairs and showed her around the house showing her Jason’s office as well as her office, the main room, the entertainment room, the kitchen, where she met Matilda and the upstairs, where the guest room and master bed room was.  Jill was told her duties, were to keep the home spotless, besides being available for use as they desired.  Jill was told Tuesday nights she was the night Manny and Matilda were allowed to use her for their pleasures.

Carmen took Jill back to the dungeon and secured her to the ST. Andrews cross.  Carmen unlocked and removed the chastity belt from Jill and then slowly teased her body, getting Jill excited.  Jill felt her Mistress’s touch over her body and it responded as she felt her nipples become swollen and hard, and see felt her juices starting to flow from her cunt as her clit and labia started to grow.  Sudden Carmen slapped Jill’s right tit very hard and Jill cried out in pain.  “Slaves are not allowed to cum without permission” Carmen told her as she again teased Jill’s body and inserted one of her fingers into Jill’s very wet cunt. As Carmen found Jill’s clit and started to play with it, she whispered in Jill’s ear “Cum slut NOW”.  That was all Jill needed to hear as she immediately came flooding Carmen’s hand with her juices.  Carmen removed her fingers from Jill and licked them clean, stating how tasty they were, and now that Jill had some pleasure the rest of the night would be very painful.

Carmen attached a set of cloverleaf clamps to Jill’s nipples and to each clamp she attached an empty cup.  Carmen then hung two water bags from chains above each clamp cup and started a slow drip into each cup.  Jill realized what was happening and knew as the cup filled the clamps would get tighter and tighter crushing her nipples.  Jill watched as Carmen left the dungeon smiling a very cruel smile.  Jill hung on the cross alone in the dungeon feeling her juices still running down her legs and the clamps slowly getting tighter with each drop of water and totally helpless to do anything.  Jill smiled as this was exactly what she had always dreamed of, being someone’s helpless tortured slave.  As the clamps continued to get tighter the pain started to get Jill excited and at some point she started floating in sub space and had an unbelievable orgasm and passed out.

Carmen was watching Jill by closed circuit video and when Jill passed out she went into the dungeon and released the clamps on Jill’s nipples and released her from the cross and placed her in a sex swing cuffing her wrist to the chains above her head and her legs were spread and cuffed to the other set of chains holding the swing.  Jill came out of the pain induced trance to find she was helpless in the swing and alone in the dungeon.  Her nipples were still sore from the clamps but other wise she was fine.  Jason and Carmen entered the dungeon and Jill looked up at them and smiled.  They asked if she was okay and Jill said she was fine.   From a drawer Carmen pulled out two sets of clothes pins with string connecting them.  One set was placed on her right labia and the other on her left labia and the strings were attached to the chain on each side spreading her cunt wide open.  From another drawer Carmen pulled out a weird looking device which was basically round with a long tail coming out of the bottom and a clamp at one end.  The device fit over Jill’s spread cunt with the tail inserted into her cunt and the clamp tightened around her clit.  Once turned on the whole thing vibrated and the tail inside her cunt wiggled while vibrating.  Jill’s body immediately reacted to the vibrator and she started to reach a climax.  Jason smiled and softly said “CUM”.  Jill burst into a climax which was amazing.  But she suddenly realized the device was getting even stronger in intensity and driving her to another orgasm.  Carmen whispered in her ear.  The batteries will last about three hours and it will keep getting more intense so have fun.  Jill could not believe they were leaving her here it this position as she knew from experience after a while it would start to hurt to keep cumming, and that would only increase her pleasure.  After an hour Jill was screaming to please turn it off, but there was no one there to do it.  Her mind was in overdrive as the pleasure and pain mixed turning her into a constant cumming pain slave and her cunt was aching but she didn’t mind.

At the end of the three hours and what seemed like an endless orgasms they returned and shut off the device and removed it.  Jill was released from the swing only to be pulled under hanging chains and her hands were quickly attached to them, while her ankles were cuffed to floor rings spreading her wide apart.  Jason stripped and she looked at his rock hard huge cock.  Jill saw Carmen strip and get a huge double dildo strapon, and slide one end into her cunt and tighten the straps.  Jason said he wanted her ass this time and moved behind her and started to slide his lubricated cock into her ass.  Once he was fully in her ass Carmen move in front of Jill and slide the 10” dildo deep in her cunt.  Then the two of the started fucking Jill’s ass and cunt and Jill could not believe her body could still respond, but as Carmen started to suck on her hard nipples while fucking her and Jill was in heaven as all three came at the same time.  Jill was released and place in her cell for the night to sleep.  An exhausted well pleasured Jill fell asleep smiling. 

The next morning being Tuesday, Jill knew she was to serve Matilda and Manny.   She found inside her cell a rubber maids dress and once she put it on she saw the cutouts for her breasts and the skirt was just below her waist exposing everything.  The only other piece of clothing was the 6” heeled shoes that she put on and then found her way to the kitchen to find Matilda.  Jill entered the kitchen and saw Matilda, who was about 5’6” 145 lb and average build and about 35yrs old, standing there.  Pointing to the table she told Jill to sit down and have a cup of coffee as they chatted.  Matilda told Jill she was bi sexual and did enjoy domination but not to the extreme of Carmen and Jason.  Also her husband Manny was really not into BDSM, but did enjoy the Tuesday night threesome.  Jill asked her how long she had lived her and Matilda told her for the last eight years.  Jill asked her if she enjoyed being here and Jill was told that it was better than jail, since she had been setup for a murder charge and only because she was a gourmet cook from one of New York’s best restaurants and became a citizen of the small island that she could not be extradited back to the US and was very grateful that Carmen brought her here.  Jill asked her how many other slaves had been here and she was told they basically stay one year to get the money and leave, just as Amy the last slave did. Jill told her that she did not know how long they would keep her as their slave, to which Matilda questions what she meant as she knew they could leave after a year.  No, Jill told her the contract I signed only allows Mistress and Master to terminate it as I requested that, as I have dreamed of being a slave my whole life.  “WOW said, Matilda that really is different.”  I hope you know what you are in for?  I do know said Jill and showed off the tattoo on her ass to prove her point.  Matilda then asked what she did before slavery.  Jill told her she was an accountant and was very good at that, but her heart had always been in BDSM. 

Well Matilda said as she lifted her skirt and Jill could see she was not wearing underwear and had a very thick bush around her cunt, get down on your knees and suck me off NOW.  Jill dropped to her knees and put her head between Matilda’s legs and started licking her cunt.  She watched as the lips slowly spread apart and the juices starting flowing, before attaching the clit and driving her tongue as deep as possible into her cunt.  Jill felt the legs tighten around her head and a hand pushing her face tighter to the now dripping cunt as Matilda approached her orgasm.  As Matilda came, Jill drank in all the juices she was squirting down her throat and then started over again until Matilda had a second and third orgasm.  Matilda told Jill that was a great start to the day and she was as good as any slave that had lived there.

Jill’s life became one of a slave, cleaning and serving every need of Carmen and Jason as well as her Tuesdays with Matilda and Manny, and her adventures in the kitchen.  One day as she entered Jason’s office she heard him curse and said “I am sorry for disturbing you Master”.  Jason smiled and told her it was ok, he was just frustrated as he could not figure out how one of the businesses he owned in the USA  showed great sales, but very little profit.  Jill asked if she could help find the problem.  Jason looked at her funny, until he remembered her background as an accountant.  Jill looked over the records and after a few hours, told Master Jason she thought she found the scam, but could not prove it as they did not have access to the company’s main frame for more details.  She explained that commissions were being paid, and then the orders canceled but commissions were not returned.  But until she had more access it was hard to prove.  “So Jason asked if you were to visit the company with me, you could find the problem?”  I might, Jill responded, and I might have to hack into some of their secure files unless I have complete clearance, and asking for that could scare off the person or persons doing this and they could delete the proof.  Jason thanked her and told her she could masturbate as a reward for her help.  Jill lifted her skirt and shoved three fingers deep in her cunt and quickly brought herself to an orgasm.  Jason told her to continue her duties while he thought of what to do next.   Jason discussed the problems with Carmen who agreed that a trip to the company in question and take Jill with him.

Jason called his friend Tim (whose company was the problem) that he was coming to the US to visit several companies and would see him in a few weeks.

The next day Jill was called into Jason’s office and when she arrived, he was talking to a tall geek looking man.  She was introduced to Wayne who she was told was a one of the worlds leading hackers and was here to teach her how to hack into the computer system in question.  Wayne looked at her and laughed, telling Jason, he doubted this sexy bimbo, could ever learn how to hack a computer.  Jason smiled and said “Train her, if she fails I will double your fee, if she learns it, you fee is half of what we agreed to.  Deal said Wayne.

Jill sat down at the computer as Wayne stared at her naked breasts, and let’s start.  Wayne asked how familiar she was with a computer and how it worked.

Jill told him, she was very familiar with this model, even though it was not the best and not to treat her as an idiot as she was most likely smarter than him and if his IQ was higher than hers she would suck his cock, if Jason allowed it.  Jason just laughed and said that was okay with him.  Wayne said my IQ is 197, so slut get on your knees and start.  Jason told Wayne he lost as Jill’s IQ was over 200, so he should shut up and just train her.  Wayne stared at her and asked politely where she went to school.  Jill told him she graduated from U of Penn’s Wharton School of Business with a Masters degree and graduated magna cum lade.  Wayne apologized and started training her.  By the end of the day, Wayne told Jason, she could hack just about any computer in ht world, and if she was ever let go, he would hire her.

Jason explained that they were going on the trip and she was to play the role of his bimbo secretary and secret lover and sex slave.  Jill smiled and said no problem; I already am your bimbo slave and lover.

Carmen entered Jason’s office and told him that Amy was on Grand Cayman Island and had contacted her about returning as a slave. Jason said this is perfect, I can have Jill as an accountant and you can have Amy as the maid and we can torture both of them.   Have Manny pick her up and bring her here so we can talk to her about the new contract and her status here.

Manny picked up Amy at the docks and brought her to Matua by speed boat.  Amy knocked on the door after Manny drove her to the house after they landed.  Jill opened the door and Amy introduced herself and said she had an appointment with Mistress Carmen and Master Jason.  Amy followed Jill to Jason’s office where she entered and stood in front of her former owners. Carmen told Amy to strip, and Amy removed her dress, bra, thong and shoes and stood nude in the proper slave position. Jason asked her, “Why should we take you back”.  Amy told them she went to Europe and was scammed by a handsome man, who she trusted to invest her money.  She realize she was lost in the real world after being a slave for a year obeying every order, that she didn’t know how to act and desired to be a slave again.  Carmen told her that they had a new slave Jill, who unlike the others, including Amy, signed the contract, with no exit clause and requested the contract could only be terminated by them.  Also Carmen noted that Amy had her piercings removed and told her she would be repierced.  Amy was told if she agreed the contract would be identical to Jill’s except her payment would be $10000 a year, since she already had been paid the normal payment.  Amy started to cry and said I will sign any contract you want as I did not realize how much I enjoyed being your slave and will do anything to be your slave again.  Jill was called into the room and told to strip.

After removing her dress and shoes, Jill stood in position wearing only her collar, chastity belt and cuffs.  Amy, are you willing to be pierced as Jill and wear the same tattoo on your back as she does?  Amy looked at the tattoo and smiled saying YES Mistress.  After a few minutes of talking to each other Amy was told she could stay as a slave here again, but her status was as the lowest slave, and she would be below Jill.  Carmen handed Amy a slave collar and told her to lock it around her neck as a sign she was doing this of her own free will.  Carmen told Jill to take Amy to the dungeon and strap her in the gyn chair and get the piercing equipment.  Jill attached a leash to Amy’s collar and took her to the dungeon.  Amy told Jill she was beautiful and loved her tattoo.  Once secured to the chair with legs spread apart, Carmen pierced Amy’s nipples labia and clit with new permanent rings end then locked Jill and Amy in their cells for the night.

Amy asked Jill how she enjoyed being a slave, and Jill told her it was everything she wanted and had given up her high paying job for this.  Amy could not believe this, but seeing how Jill was so happy, she realized this was a good life.