Tim Ch. 01

"On your knees whore."

As ever Jessica did as she was told and saw Amir wanted her to remove the condom and lick him clean. This she did, sucking as enthusiastically as she could. After she had finished her task, Amir pulled on his trousers and left without a word of thanks.

It was a tired Jessica who returned to the basement that evening. She saw a pensive Tim.

"Jess, I have a plan. You know Sophie wants to whore you out on Thursday. Well this is our chance, perhaps our only chance, to escape. To work we need to convince her of two things; first that it is too dangerous to do things here, danger of damaging stuff and the possibility of either her mother or father coming back earlier than anticipated. The second is to bring me along. It is important to get out of this place, the security is simply too tight. If we can convince them to use a hotel they must let us out of the handcuffs at some point, even if it is only to cross the lobby or during sex itself. You can't fuck with your hands chained behind your back. If I am around I am sure I can overpower them. Drop a hint about the danger of doing things here, you can say you are worried about what Mr Al-Battani may do to you if he catches you on the job. You can also mention I was a bisexual escort at University, I wasn't but I will back you up; that should encourage then to take a risk on bringing me. You have to drop the hints subtly so Sophie doesn't realise she is being manipulated, but I think this is our one chance before we are handed over to CBC."

Jessica went to work on Sophie dropping a number of subtle hints hoping the hints were clear enough for the air-head to pick up but not too obvious that she would suspect a trap.

Her comment that Tim used to be a escort brought almost immediate success. Tim was ordered to come to Sophie's room, allegedly to do some heavy lifting, when he got there he was told to strip and Sophie photographed him naked. She quickly e-mailed it to her friends saying he was available for a limited number of dates.

Sophie did not summon them on the following day, staying cooped up with Safia in her room telling her parents they were working on their school projects. In reality they were working the phones negotiating prices for Jessica and Tim. They giggled as they decided on prices for the various sexual acts. They had no real idea of what local whores charged but suspected their school friends did not either. Anyway after some fraught negotiations they set up Tim with three dates, two women (one notoriously ugly, so bad Sophie insisted on charging her double) and one man. Jessica had seven dates, all men. Sophie booked a room at the local Holiday Inn. She and Safia took security seriously, deciding to keep Tim and Jessica handcuffed at all times except when they were with clients. Then Safia would stand by the door with her mother's Taser gun.

Sophie summoned Jessica and told her of her plans. Sophie said she and Tim should be ready to leave as soon as her mother had departed for her bridge party which should be around 2.30pm the next day.

Sophie gave Jessica a list and timetable of her and Tim's prospective dates, this included the name of the client and what sexual acts they had paid for. At the bottom of the page, in Sophie's girly writing, were some general instructions; new underwear for each client, wash between clients, only provide the paid for services and smile - make it seem as if you are enjoying it. Lastly Sophie promised Jessica $100 if things went well.

Jessica went back to the basement to tell Tim about the developments, it seemed they had a real chance of escaping, all they had to do was overpower two teenage girls, this couldn't be too difficult. Tim never had any real conscience about punching girls at the best of times, and certainly none when potentially his life was in the balance.

Jessica then started explain some of the things that Tim should know if he was to act the whore.

"It's easy anyone can be a whore. I have had sex therefore I can do it."

"Tim as ever you are being arrogant. Being a prostitute is like any other profession, anyone can do it badly but it takes time, skill and practice to do it well."

"Look I have only three dates and they are in all likelihood virgins, they won't know the first thing about sex."

"OK, what about the boy?"

"I am sure I can give a blow job, it is just putting his cock in my mouth and sucking. Anyway unless you want me to proposition Mr Al-Battani, I don't see how I can practice at this stage. Giving head, I have taken you anally so I can't really see a man being that much different. I suppose the only difficulty might be being taken. I confess I have never done this, and I don't much want to."

"Tim I don't want to risk anything, remember the rest of our lives are at risk. We have almost eighteen hours until we leave, at least do a little practice."

Tim looked at his adorable girl friend, she was clearly serious, so to shut her up he agreed to her request. He was pretty sure it would be a waste of time as he hoped to overpower Sophie and Saphia in the hotel lobby and if this was impossible as soon as they got to the room, one way or another well before young Azziz appeared on the scene. To keep Jessica happy he agreed to practice when she was serving dinner. When she had gone, he got the lubricant and smeared it over his anus and then tried to insert Jessica's vibrator, he pushed really quite hard but it simply would not go up. After about five minutes of trying Tim gave up, he was simply created heterosexual that was all.

About 10pm, Mahmoud unlocked the basement door and told Tim he was wanted in the drawing room. Tim walked up assuming he was need to clear up or some other menial duty. He was shown into the room and told to kneel by Jessica's side. He looked around and saw Sophie, Mr and Mrs Al-Battani and a distinguished looking caucasian gentleman with greying hair and a certain gravitas. Sophie called him 'Mr Cartwright'.

After a few minutes Mr Al-Battani looked at Tim and Jessica and smiled, "I have some good news for you two. As you know I intended to claim the bounty that the Commercial Bank of Chelyabinsk put on Tim's head. You will of course accept that this was in no way personal just a business proposition. But luckily for you Mr Cartwright, an old friend, has offered to outbid CBC so you will not be heading for what is reckoned to be the most contaminated place on earth to help hold up some concrete bridge. Mr Cartwright will be taking you to his island where you will be expected to work for about two or three years after which you will be free to leave. By then the CBC may well have got bored of looking for you. So you can both live happily ever after."

Tim spoke up, "Thank you Sir. What will you expect us to do? I am a good accountant and I know Jessica is an accomplished cook."

Mr Cartwright answered in a barely audible whisper, "My business is prostitution and you will both be expected to service my clients both men and women."

It took a second for this to sink in. Tim then growled, "No ****ing way. I would be keener to try my luck with the Russians than become some ****ing sodomite's plaything. Much better a quick death than that." He began to rise to his feet to make the point more emphatically when suddenly Mahmoud grabbed his arms and handcuffed him. As Tim fell back on his knees he continued to swear with ever increasing creativity. Mahmoud then gagged him as well. As he did so he gave Tim a couple of hard punches in the stomach. Mr Al-Battani did not like profanities.

Mr Cartwright turned to Jessica wondering if she would give a similar performance. But she looked demure and stayed silent.

"So Jessica, do you accept my offer?"

"Yes, Master."

"Good I think we will get on well. Your experience in the sex industry will be of great benefit and you will be much better paid than the pittance your previous pimp made you live on."

Sophie then piped up, "Jessica told me that Tim was an escort at uni, so he should also be at home on your island." The adults looked over at her wondering how this could have come up in conversation with her maid, but no one made any comment.

Jessica was then taken back to the basement and told to be ready to leave the house at 8.30 am the next morning. Tim was taken to the hall and left chained and handcuffed.

The next morning Jessica, dressed in one of Sophie's old summer dresses, was shown to Mr Cartwright's Bentley. She did not see Tim, but it quickly became evident that he was in the boot and was thrashing around like a madman. Jessica's heart went out to him, but she knew there was nothing she could do to help. Jessica also knew that she was in no position to resist Mr Cartwright's demands, so she resolved to try and ingratiate herself with him.

Mr Cartwright made charming conversation until the banging from the boot came too much. He ordered his chauffeur to sort Tim out. A couple of muffled shrieks indicated the chauffeur was not bent on negotiating. From then on there was no more banging. The chauffeur admitted he had attached Tim's ankle cuffs to his hand cuffs effectively hog tying the poor boy, so it was tricky to do a great deal of kicking regardless of his unhappiness at his predicament.

At a small jetty they were met by speed boat and Jessica was escorted and Tim man-handled aboard and they set off towards Cartwright & Palmer's private island, their home for the next few years.

~

Whilst the security guards marched Tim away, Mr Cartwright escorted Jessica in the opposite direction, showing her to a comfortable suite of rooms. Before he left he invited her for dinner that evening in his penthouse. Jessica sat down and thought about what the future held for her. On a positive side the room looked great, but she had a natural fear of the unknown, what would she be expected to do? Sex obviously, she could handle that, but if that was all they wanted they would not have had to kidnap her. What other services would she have to offer? She assumed Mr Cartwright would enlighten her.

After a bath, Jessica explored the room, finding bikinis, underwear, gym kit and a beautiful evening gown. The dress was well tailored and flattered her body making her feel sophisticated. Despite her predicament she felt good. They had even left some understated jewellery out for her. So it was with some trepidation, but also a little undeniable eagerness, that Jessica went up to Mr Cartwright's luxurious flat.

Mr Cartwright gave Jessica a wonderful dinner. He was witty and gracious, a great companion. This was really too good to be true. Jessica wondered how the evening would end. In her heart she knew, after all this was a brothel. She decided to take the initiative, "That was a truly lovely meal Jerry. If I were a poet I would promise you verse, if an artist you would have a painting. As you know I am a whore, therefore all I have to offer you is my body. Please accept it."

"My dear Jessica. It is a kind offer, which I truly appreciate. I have very much enjoyed this evening. But much as I would love to take you to bed, I am afraid I have to be up terribly early so I can fly to New York. Just remember if you ever have any difficulties when you are on the island, you can always give me call. I will help in any way I can." So Jessica's evening ended with a chaste kiss.

Jessica's time on the island had started as well, Tim was not so lucky. On leaving the boat, Tim was dragged down the street of what seemed to be a normal holiday resort. Perhaps the only difference being the number of unusually attractive people he passed. They arrived at a small single story building. It appeared to be a moderate sized private house in its own grounds, but when Tim entered he found that appearances in this case were deceptive. It was evident that behind the anonymous exterior there was a high tech prison. On entering Tim was forced to strip naked and put on a slave collar. He was immediately photographed and finger printed. He was then examined by a doctor and finally placed in a fifteen foot square, immaculately clean, white tiled cell. The room had no window and was devoid of any furniture other than a white padded bench and a bucket. It had a CCTV camera near the ceiling and some shackles attached to one wall.

The first day was uneventful as was the second, the only real problem was boredom, he was given nothing to read and the guards clearly had orders not to talk to him. All he had to do was think. What would happen if he refused to work as a whore. Would they simply hand him over to CBC or was worse in store? Tim got used to eating from a dog bowl and kneeling whenever a guard entered his cell. He was beaten whenever he breached any of the rules.

On the third day Tim knelt when a pretty chubby-cheeked female warder entered his cell. He felt intensely humiliated as she explained she was there to shave his body hair and ordered him to lie down and spread his legs. She began but trimming the longer hairs with scissors then splashed hot water over his balls and covered his pubic area with thick menthol shaving foam. The girl took an age to shave him, moving his stiffening penis back and forth at will. She seemed to enjoy her work stroking Tim's inner thigh to make sure he was totally smooth. Tim was embarrassed at his growing erection and the smirk on the teenager's face. She shaved his legs and chest and had him on all fours as she shaved the hair around his anus. When she had finished she made Tim kneel before her and then kiss her shoes. She explained she would be in to shave him each morning from now on.

Later that day Tim, now feeling even more vulnerable, was taken to an office and told to stand naked in front of the Head Warder's desk. A middle aged lady with an unremarkable appearance studied him. Eventually she spoke, "Tim, you know why you are here. Mr Cartwright bought you for a considerable sum of money. It is my job to see to it that you perform as required. As you have seen, we run a very exclusive holiday resort. Our real selling point is that we provide our guests with escorts who will indulge their sexual desires, whatever they may be. It is only fair to say that this often involves the escort indulging in 'unusual' sexual practices and being punished, the pain can be fairly intense but won't leave any permanent damage. Your submission will be total and you will be expected to serve our guests with genuine enthusiasm. It hardly needs to be said, you will be well paid if you please them and punished if you disappoint. Please be under no illusions, you will work for us, the only question is how much pain you will endure before you submit. If you do try to hold out, you should remember, some of our guests like boys who put up a bit of a struggle. So, not to put too fine a point on it, they will pay to rape you. Now you know the ground rules, let's get into the detail; have you had anal sex?"

Tim's heart sank, this was worse than he feared. He gulped and replied, "No ma'am."

"Right we need to work on this." She handed Tim a dildo and some lubricant, "Please start with this. The dildo is only an inch diameter so you should not have any great difficulty in getting used to it."

Tim took the dildo without comment, he wasn't sure what he was going to do. He was getting the idea that Cartwright & Palmer were not going to accept his continued refusal and he may have to accept the inevitable.

"Tim we will monitor your progress. Each week we will give you a dildo with an eighth of an inch larger girth. Looking at you I think you should manage a four inch dildo eventually." The warder then placed a monster of a dildo on her desk.

Tim gasped at the size, thinking that there was no way he could take something like that. He couldn't get it in his mouth never mind his anus. He now knew he would never survive this.

"But ma'am, I can't, I won't put those things up me."

"Oh yes you will Tim. Anyone can get used to anal with a bit of practice and let's face it you have a lot of time on your hands. If you refuse, our security detail will be only too happy to do it for you. It is for you to decide, but I have to advise being violated several times a day is pretty painful. They are not gentle individuals."

Tim did not reply, the thoughts going through his mind were simply too terrible to articulate.

"Tim you have a whipping at 1.30pm tomorrow, be sure you are ready to leave at 1pm."

Tim did not really need to hear that he was in for more pain, the four inch dildo had convinced him. He could not continue to resist, "Ma'am, can I submit now?"

"No Tim, I don't have the authority to accept submissions. You will have to wait for Miss Christensen on Thursday. Even then she may not accept your submission. Anyway the bidding for your whipping has already started and we can't let down our customers."

The Head Warder rotated the monitor on her desk and Tim saw a picture of himself bending over naked. The page indicated that the auction was open for the right to whip him twelve times. He noted the bidding had only got to $50, somehow this hurt his pride, surely his pain was worth more than that.

The warder seemed to read his mind, "Tim don't worry about the price, things always hot up just before the auction ends. Many people like to see the merchandise in the flesh before they bid. I am sure you will make several hundred dollars. You will get used to this, you will be auctioned every other day for the duration of your stay here."

At the appointed hour Tim was removed from his cell, and the warders buckled on black leather wrist and ankle cuffs, his hands were then secured behind his back and a lead attached to his collar. His guards then led him out of the prison. It was then that his nakedness struck Tim, he had almost got used to it in the prison with the few warders. Suddenly he was being dragged along a major street. He looked around and saw although many people wore very daring bikinis he was clearly the only person stark naked. He could do nothing to protect himself.

When he got to a courtyard he was forced to bend over a hurdle and when the wrist cuffs were removed his hands and neck were placed in some stocks. His ankles were then attached to the base of the hurdle leaving him totally secure and helpless. In front of him he saw a screen displaying his photo and the current auction price for the privilege of beating him. All but one of his guards had left. Tim was quickly surrounded and his felt unwelcome hands stroke his bottom and even his cock.

Tim watched the screen watching as the bidding increased, he could not quite understand why but he hoped he went for a decent sum of money, not that he really knew what was par for a whipping. It was not readily available at his local supermarket. As the clock counted down the last few seconds, the bidding rose to $340.

The crowd then moved back and the guard congratulated the successful bidder, offering them a paddle or a crop. A tallish, bikini clad lady stepped forward choosing the paddle. She had medium length straight blond hair, parted in the middle; she was probably in her late forties or early fifties but retained a good figure and seemed confident. Tim realised the moment had come and he was about to become a public entertainment. The lady walked behind him, out of view. Without warning Tim felt a loud crack as the paddle hit his buttocks, along with intense pain. The lady was not play acting. Tim struggled as his natural reaction was to avoid further hits or defend himself. His bonds were far too secure and he was held fast. The second and third strikes came soon afterwards, as they hit the same spot the pain increased. Next he felt a swat on the inside of his right thigh, then the left. The relief of not getting struck on his now very tender buttocks was balanced by the sensitivity of his inner thighs. Then came two further strikes on his lower buttocks followed by another two in the centre where the first three had landed. The woman finished off with a salvo of five shots which gradually moved from the top of his buttocks to his lower thighs. By this time any prospect of silently taking his punishment was well past, Tim shrieked with pain, he had never felt pain like this. He had played S&M games with ex-girl friends but that was playing this was serious, it seemed the lady was getting real sexual pleasure from hurting him.