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Tim Ch. 01

By: TimT1972



1 – Sold into slavery


Tim lay back in bed and thought that life seemed perfect. He was living in a palatial villa on the Tunisian coast with the most gorgeous girl he had ever seen. He had stacks of money and his life involved sunbathing and great sex. It was a dream, but he knew his life was not quite as perfect as it appeared to be. Tim regularly woke up sweating from a nightmare in which he was about to be kidnapped by some faceless Russians. This would seem paranoid to most, but in Tim's case it was a sober recognition of reality. He was on the run.

Tim thought back to the previous June when this story really began. He had been asked to buy $100 million in a bond fund and due to some carelessness he sold instead, by the time he realised his mistake the value of the fund had risen by 4%, effectively losing the bank $8 million. He now realised that he should have admitted his mistake and taken the consequences, which may have been as slight as the forfeit of his bonus and at worst would have been dismissal. Instead he covered up the loss by entering some fake trades into the system, his intention was to trade out of the loss. He almost managed it, but almost inevitably the markets went against him and instead of a loss of $8 million he had a $14 million hole. As the annual audit approached he knew he was never going to manage to recover the money. After much thought he decided it would be better to escape before he came under suspicion. He knew he had been a fool, but was still quite proud of how he planned his flight. Tim booked two weeks holiday ensuring that none of his fake deals matured until after the end of this period. He than explained to his boss, Mr Tolbukhin that he needed to settle a trade with the National Bank of Albania in gold bullion for "tax reasons". Tolbukhin, the drunken ass, believed him and authorised Tim to obtain the gold bars asking for a receipt by the end of the day. Tim produced the receipt as requested, by scanning in an official looking letterhead onto his home computer and signing the resulting form "E.Hoxha". 

Tim then went home and called Jessica and explained his predicament. She had clearly known he was under huge pressure at work, but the size of the loss surprised, even horrified her. The sight of the gold made her realise this was not some cheap joke. Tim explained he had to leave and she had about 24 hours to think if she wanted to come with him. Jessica had not mentioned that she had pressing reasons to leave London, or more accurately one pressing reason, an angry and aggressive pimp. Unlike Tim her savings would make it difficult for her to flee much further than Cleethorpes. So at the appointed time Jessica was ready with her suitcases.

The flight itself was relatively painless, they drove all the way to Gibraltar where they sold the car. They then bought a beaten up Datsun in Tangier for cash.

Tim expected to see his name on the front pages of all the British papers; another poster boy for the irresponsible greedy bankers. In fact he saw nothing, clearly the Commercial Bank of Chelyabinsk, or CBC for short, had taken the loss on the chin avoiding the bad publicity.

It was now three months since their flight. Tim still had nightmares but now they were no longer nightly occurrences, sometimes a full week went by without him waking up once. The nightmares had been so frequent that his body was now quite used rolling over and quickly getting back to sleep.

As soon as Rafik saw that Tim had gone back to sleep he signalled to Mahmoud and Bachir to come up the stairs. As Rafik covered them with his trusty Steyr his colleagues covered Tim and Jessica's faces with chloroform soaked rags. When they were confident the two were out cold they handcuffed them. As Rafik cleaned out the bathroom cabinet, just in case either of the two was on some medication, Mahmoud and Bachir carried Tim and Jessica down to the waiting van. 

When they arrived at their destination, Tim and Jessica were still only semi-conscious. They walked across a large hall and were told to kneel in what was evidently a living room. The chloroform was still having its effect as neither Tim nor Jessica put up much of a struggle or even complained about their treatment. 

Leaving Mahmoud to guard them Rafik went to find his boss, Mr Al-Battani. He found him in his study with some of his closest confidents. Knocking softly on the open door he said, "I have got the two people you asked for. They are in your drawing room, sir."

Mr Al-Battani excused himself and went off to see his prizes. He smiled when he saw them, "Ah, Tim, Jessica welcome to my humble abode. You may have wondered why the Commercial Bank of Chelyabinsk did not report you to the police. You have now found out, they like to handle fraud themselves."

The name of his previous employer rang some bells in Tim's woozy head. He did not recognise his surrounding, and for some reason he could not move his arms. It gradually dawned on him that he was naked and the reason he could not move his arms was that they were handcuffed. The man looking down at him appeared friendly but even in his current state he realised that appearances were likely to be deceptive.

As he tried to concentrate an elegant lady entered the room.

"Oh, darling these two will be with us for a few days. They will be sleeping in the cellar. Rafik will look after them."

Mrs Al-Battani was used to her husband kidnapping various unfortunates. They tended to be gamblers down on their luck and she was only too happy for them to be kept out of sight. These two were different, they were in their late teens or early twenties and were both remarkably pretty and looked harmless. She assumed they had been kidnapped to serve in one of here husband's brothels.

"Fine, as Halima is on her holidays can I use them around the house?"

Mr Al-Battani was slightly surprised by the request as normally his wife barely hid her distaste for some of his more brutal activities. Looking at Jessica he thought it would be fun to have her around until he could negotiate a handover. They were unlikely to escape as the villa's security system was one of the most advanced in the country. They were also miles away from the nearest habitation and a couple of naked whites would be fairly easy to track down.

"OK, darling, but it will only be for a few days." 

Returning to his study Mrs Al-Battani turned to Rafik and said, "Take them down to the cellar. Bachir, get the girl a maid's outfit and the boy some shorts and a T shirt."

Bachir turned to his neighbour and asked in despair, "Where do I get a maid's outfit?"

"Bachir, did you see the girl? She was naked. She must be prostitute, as such go to Mrs Jubayr's whorehouse. She had loads of uniforms for her girls. She will be able to kit you out with something."

The next morning Jessica woke up her hands still handcuffed behind her back. She looked around the room, initially she thought this may be one of Tim's kinky games, but when he saw Tim looking very worried and similarly handcuffed she quickly realised they were in deep trouble. Tim summarised the situation, CBC had tracked them down and at least his life could now be measured in days if not hours. Jessica wondered what her fate would be. She really had very little experience of quasi mafia type organisations so all she could come up with was stock clichés like "She knew too much." Realistically she knew her prospects were not good.

As they talked the door was unlocked and Bachir entered. He threw some clothes on the bed, unlocked the handcuffs and said, "Put them on and follow me."

Tim and Jessica did as they were told. Tim squeezed into some tight shorts and was about to complain when he saw Jessica, she was in French maid's outfit that was so skimpy it barely covered her tits or bottom. Jessica was embarrassed, this was the sort of thing people wore in the bed room not around the house, but she pulled and stretched the material and just about made herself look semi-decent.

Bachir escorted them to Mrs Al-Battani, who looked at Jessica's dress and exploded, "What is that? She looks like a prostitute not a domestic."

"Sorry Mrs Al-Battani I could not find a normal maid's uniform in town."

"Oh never mind, it will only be for a few days." Mrs Al-Battani looked up to heaven, she knew her dear husband did not choose his associates for their brains but Bachir really 'several tokens short of a toaster'.

Mrs Al-Battani then showed Tim and Jessica where the cleaning materials were and put them to cleaning the kitchen. Tim was told that he was to clean from 7.00 to 9.00 each day and after that he was to be locked into his room unless he was needed for specific tasks. In addition to the cleaning, Jessica was to serve meals.

Jessica stationed herself in the dining room and greeted Mr Al-Battani with a curtsey when he got down. He was surprised at her outfit but unlike his wife he thought it was a rather nice way of starting the day. He ordered some coffee and started on his newspapers, Al Chourouk and the Wall Street Journal. Mr Al-Battani tried to concentrate but his new maid was so much more interesting. Jessica stood by the sideboard tugging at her short satin skirt, trying to get it to cover her suspenders. Perhaps he should delay the handover for a few days. Halima was a darling but somewhat spherical, not a patch on this Jessica. He wondered if CBC would let him keep her, surely they only really wanted Tim. This seemed a possibility but he knew his wife would never agree. 

As he pondered, he saw his daughter come in. As ever, she was dressed in scruffy ripped jeans and a sweatshirt. She was a pretty girl, but would look so much better her father thought if she smiled at least once in a while, rather than wearing her habitual sneer as if her life tottered between boredom and irritation.

Jessica curtseyed and asked the girl if she could get her anything.

"Coffee, black, no sugar. By the way what the hell are you doing here dressed like some cheap tart?"

"I am helping in the kitchen whilst Halima is away, Miss."

"OK, Sophie no need to be rude. She is called Jessica and as you know your mother needs help around the house. She will only be with us for a few days. She can help you if you need anything done, like perhaps sorting out your room..."

Sophie put her iphone headphones in her ears and drank her coffee.

When Sophie had finished she returned to her room. On closing the door she immediately rang her best friend Safia. After the normal greetings Sophie got down to the point, "You won't believe it. My father has got a tart. She is masquerading as a maid but my mother will go ballistic! This will be fun. Come over and watch."

Sophie got down for lunch early, eager to see the first skirmishes of what she assumed would be the mother of all domestic fights. She was disappointed, her mother seemed to treat Jessica with exaggerated kindness. In fact the lunch was a very jolly affair with both her parents being on genuinely good form.

Sophie was still suspicious and knew the only way to find out what was going on was to question Jessica in private. So, in as relaxed voice as she could manage, she asked her father if she could use Jessica for a few hours that afternoon as she need some filing done for her school project. Neither of her parents objected and Jessica was told to present herself at Sophie's room at 3pm.

On entering, Jessica saw Sophie and her friend (Safia) lounging on her sofa chatting over a cup of coffee.

"Can I help, Miss Sophie?"

Sophie looked up and answered, "Yes, Jessica, what I really want to know is, are you fucking my father and if so does my mother know?"

Jessica denied the allegation and despite Sophie's insistence she stuck to her story. Sophie knew she was no interrogator but almost believed her.

"But you are a prostitute aren't you?"

Jessica was again caught off guard, she wondered how Sophie could have found out. Perhaps Sophie's knowledge explained her instance that she was sleeping with her father. If Sophie knew about her background, it was pointless denying it.

"Yes, Miss Sophie."

After her previous denials Sophie was surprised by the admission. 

Safia now spoke for the first time, "I have never met a whore. Let's see you. Take off your dress."

Jessica looked at Sophie, who merely nodded. Jessica wondered what Mr Al-Battani would say if he was there, but he wasn't. Jessica decided she had better comply with the request as the last thing she wanted was to have made an enemy of the daughter of the house. She struggled out of her uniform and stood before the girls in her brief knickers.

"And the rest Jessica, no need to be modest."

Jessica took off her knickers and stood naked in front of the girls as they photographed her with their phones. Saphia became more confident and got Jessica to pose more and more provocatively; pushing out her tits and fingering her pussy.

"Jessica we are keen for you to explain about sex, you must be an expert."

Sophie went to her chest of draws and retrieved a vibrator, "Show us how a professional uses one of these."

Jessica knew she could not pull out at this stage, so started explaining some of the techniques she used to give herself pleasure. Eventually at the girls' urging Jessica got down and started a practical demonstration, as she got going she inevitably started to get excited and was soon pumping away in a world of her own, barely conscious that Sophie and Saphia were even in the room. Jessica was certainly unaware of the door quietly opening but she very much heard Mr Al-Battani when he opened his mouth, "What the **** are you doing, you trollop?"

Jessica dropped the dildo and tried to cover herself, the latter was not much of a success as her dress was on the other side of the room.

Ignoring Jessica, Mr Al-Battani turned to his daughter, "Sophie, what are you playing at? Jessica is meant to be helping tidy this hell hole not putting on some third rate sex show. And you Saphia, what will your mother think?"

"Sorry daddy."

"Sorry Mr Al-Battani. As for my mother, she is quite relaxed on matters of sex and isn't it better to get guidance from a clean girl like Jessica rather than some dirty book?"

Mr Al-Battani was not convinced, this was not his vision of family life, but he really did not want to debate sexual technique with the daughter of one of his closest friends. He therefore turned on Jessica, "Out you slut, go to my study. I will deal with you later." Jessica grabbed her uniform and ran, never having been so humiliated in her (quite eventful) life.

After her father had left, Sophie looked at her friend, "I am in deep shit, my mother is going to murder me."

Saphia was not really listening, she was playing with her phone, "Sophie I have a confession to make. I e-mailed one of those nude pictures of Jessica to some of the gang and this is the response I got."

Sophie took the phone and saw the message, "I will give you $200 to sleep with her. Love you. Amir."

"No way, I am likely to be grounded for months as it is without turning into Tunisia's youngest pimp."

"OK, Sophie, that said $200 would be nice."

"Saphia, don't even think about it."

To Sophie's surprise her father did not bring up the subject at dinner and it was pretty plain that he had not told his wife. Sophie was amazed. As they left the dining room her father took her to one said and whispered, "No more demonstrations, OK?"

The next day passed slowly. In the afternoon Mr Al-Battani left for a business trip. At dinner Mrs Al-Battani announced that the following day she would be going into Tunis to shop and for lunch with Mrs Al-Qalqashandi and asked Sophie if there was anything she needed.

Sophie realised she would have the house to herself and rang Saphia to ask her over. More as a dare than being in anyway serious Saphia commented that as the house was empty it was a perfect opportunity for them to earn $200 and sell Jessica.

Somehow an idle comment became a serious suggestion and by the end of the conversation, Saphia agreed to phone Amir and offer him Jessica if could be at the Al-Battani's at 11am the next day.

Jessica served breakfast to Sophie and Mrs Al-Battani. When the latter left, Sophie indicated Jessica should accompany her to the boat house next to the swimming pool.

"Jessica, here is your costume."

Jessica took what seemed like half a dozen bright orange strings, she was confused, until she saw there was a few micro bits of material attached to the strings. This was the briefest bikini she had ever seen in her life, it was tiny. The top consisted of a couple of triangles of material not more than two inches square, the bottoms were not much bigger. She was going to have to position it carefully if she was going to cover her pussy, the rest was going to be bare. Thank God she shaved.

Jessica swallowed and started to complain, but she saw Miss Sophie's face and knew she need not waste her breath. Clearly Sophie had got around her father and she was now her plaything.

Jessica stripped and gingerly tried to put the bikini on. It took ages as her tits kept falling out of the top and the bottoms were almost as unstable. Things were not helped by Sophie staring at her. Eventually Jessica seemed almost happy that she had somehow covered her pussy and nipples, her bottom was a lost cause as there was no back at all. 

Sophie examined her, and walking around she gave the bikini bottoms a vigorous tug, Jessica felt them almost force themselves into her pussy. "Come on Jessica tighter, I don't want them falling off." Jessica tightened the sides and Sophie did the same for the top. Jessica knew that one wrong move she would now spring out of her bikini and be left almost naked. Sophie had another look and seemed satisfied.

"Good, you are ready. I have a friend coming over and he has asked to fuck you. I have said 'yes'. Don't let me down."

Sophie motioned Jessica to a sun bed and gave her a couple of condoms, "I am sure you are used to serving many more than one man a day, but this is all I could find at short notice." With that she was gone. Jessica laid back careful not to slip out of bikini. She had had sex with many men but never on the instructions of some sixteen year old. She wondered if she could tell the 'friend' that it had all been a terrible mistake as she was a respectable girl despite the bikini. But she knew Sophie would take her revenge somehow and felt this was likely to be a bit of a one-off as either Tim would come up with some idea for an escape or they would be handed over to CBC any day now. This could be the final fuck of her life. Perhaps they could blackmail Sophie into letting them go by threatening to tell her father about this. She would have to talk to Tim about the prospects.

Jessica looked up and saw Sophie leading an Arab teenager down the path. Jessica swallowed and knew she better accept the inevitable. If he was a first timer, he could be easy, in that it could all be over in a trice.

"Jessica, stand up. You are a lucky girl as Amir would like to fuck you. Give him a good time." Turning to Amir, "She is an experienced whore and will do anything you might like, even the sort of things local whores refuse."

Jessica did not like the sound of this and smiled nervously. When Sophie retreated, Jessica asked how she could serve Amir.

"Let me have a look at you, turn around."

Jessica did as she was told. "Wow, you western girls don't go in for subtlety, that thing is tiny."

Amir tugged the back of the bikini bringing Jessica stumbling into his grasp.

"Bed over you whore."

Jessica bent over Amir's knee and prepared herself for the inevitable spanking, it was probably the fact the back if the bikini consisted of a string of dental floss that gave Amir the idea. He rapidly warmed to his task raining blows down on Jessica's uncovered bottom. The spanking was done with more enthusiasm than finesse but still hurt like hell. Eventually Amir tired and told Jessica to get the bikini off and spread her legs. Jessica did as she was told and leant back, condom in hand waiting for the onslaught. Amir fucked as he spanked, impatiently and vigorously but without any refinement or much in the way of rhythm. The force of his thrust was uncomfortable but at least the assault was short and after a few minutes he had climaxed. Jessica lay back hoping her ordeal was over, but she was wrong.


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.




Tim Ch. 01



After the whipping was over Tim heard his tormentor approach the guard and say she wanted to take Tim for the rest of the day. The guard regretted Tim as not currently available but offered to take the woman's name and suite number and contact her as soon as he was free.

It was a very uncomfortable and exhausted Tim that walked back to the prison. Tim no longer cared about his nudity, he knew he could not take another public thrashing like that one. He would have to submit on Thursday.

When Tim got back to his cell, he flopped onto his bench holding his bottom, the pain was still intense. Eventually the pain became dull. Tim the realised he had better put some more time on using the dildo. He knew that the guards had him under CCTV observation and he did not want to be accused of disobeying orders, he had to ensure Miss Christensen accepted his submission.

As the week progressed, the guards began to enjoy humiliating Tim, be it making him lick their boots or watching him as he practiced with the dildo. Sometimes they would simply grab Tim and secured, beat him for no reason other than their own amusement. Most nights they made him serve in their Common Room dressed only in a short satin apron. Leony, Tim's 'barber', taking particular pleasure in humiliating him, using her lipstick to write 'slut' on his bare bottom. Tim took the punishments, counting the hours until Thursday when he could submit and hopefully leave the prison.

When eventually Thursday came, Tim knocked on Miss Christensen's door and when invited to enter, advanced and stood naked in front of her desk. He had his eyes lowered, back straight, legs together and his hands clasped behind his back, he wanted to appear totally submissive. Initially Miss Christensen did not look up. She had long blond hair parted in the middle, a classical, almost untouchable beauty; the sort of beauty that the Greeks imagined was fashionable on Mount Olympus. She appeared unapproachable, distant and superior; her demeanour was cold and forbidding. Tim felt humiliated to have to stand naked in front of her. Tim stared at the floor wishing it would open up and swallow him. Eventually she raised her eyes and said, "Tim, what can I do for you?"

"Mistress, I would like to submit."

"Do you know what your submission involves?"

"Yes Mistress, I will serve clients in any way they wish. This will involve sexual services and submitting to punishments."

"Have you ever worked in the sex industry before?"

"No, Mistress."

Miss Christensen stared at Tim. He was very handsome, but she wanted to be sure he could do the job, "Are you confident you will be able to offer your body to our clients and submit, regardless of their requests? It will be tough."

"I will try, Mistress."

"You had better do more than try. Have you been following orders?"

"Yes, Mistress."

"Then show me." With that Miss Christensen pointed to the dildo on her desk.

Tim knew this was the test of the sincerity of his submission, so tried to look confident as he took the lube and the dildo, lay down on the floor in front of Miss Christensen and spread his legs.

He took a good amount of lube and started to massage his sphincter with his fingers. The practice over the last few days paid off and he felt it relax and allow him to insert first one then two and finally three fingers getting as much lubricant as his could into his back passage. Tim then turned to the dildo which he also covered in lube and started to force it in.

Miss Christensen looked on, trying to appear bored, in reality this always excited her. It was a perfect way on humiliating a prospective whore. No overt force, just a quiet request but Tim's acceptance showed he knew he was beaten. She only really needed to see a thrust or two but she liked the look of embarrassment on Tim's face. Tim thrust the dildo in harder and harder, praying he was impressing Miss Christensen.

Eventually she said, "OK, Tim, I have seen enough. I accept your submission."

Tim removed the dildo and stood up, "Thank you, Mistress."

"Tim, you will be on probation for the first month. If you refuse any of your clients' requests or even show insufficient enthusiasm you will be back here. I can assure you people do not enjoy their second visit, please be warned. You will attend a week long course on how to serve clients, starting at 10 am tomorrow."

Miss Christensen then handed over a booklet that seemed to be a guide to the island and the rules he was expected to follow. She then passed him a pair of turquoise bikini bottoms. He slipped them on tightening the strings to ensure they were secure, they were brief but he felt so much better not being naked for the first time in ages.

As soon as Tim left, Miss Christensen picked up the phone, "Melissa, Astrid here. I have just had the most delicious boy submit. Do you want him?"

"Astrid, thanks, if you say he's good I would love to. How fresh is he?"

"We have had him here a few days to encourage his submission, but other than that innocent as hell. No experience as an escort, so please be gentle."

"You know me."

"Yes Melissa, all too well. I have a really good feeling about this one. He looks very anxious to please. I suspect he is naturally submissive, he just doesn't know it yet. I will send him over. By the way his name is 'Tim'."

On leaving Miss Christensen office Tim saw Jessica who immediately gave him a big hug, "It is lovely to see you. I am so pleased you saw sense."

Jessica led him out of the prison and along the road to the main hotel complex. She explained how they could make a great deal of cash if they put they minds to it. They had to earn $1.2 million before they were released, but she had been talking to some of the girls and found that many stayed here for months, even years, after their obligation was complete. The facilities were like the best resort one could imagine and management was pretty easy going as long as one performed and received good feedback.

Jessica explained the colour of the bikinis that they had been given indicated their grade (and therefore cost); grade ones (the most senior) wore black, grade twos green, threes red, fours orange, fives turquoise and sixes yellow. When they were naked they wore narrow collars in the appropriate colour.

Tim was amazed when Jessica showed him to his room. He had been expecting a cell or at best some cheap bedsit. In fact he was presented with a palatial suite about forty feet square. Understandably, given his new profession, the room was dominated by a large double bed, but there was still masses of space. One side of the room was made up of some huge French windows with a similarly large balcony. The room was light and airy, a quality that would have been rather out of his price bracket under normal circumstances. Tim could not help but be heartened, perhaps life would not be that bad after all. At least he was an expensive whore.

Jessica went to the balcony and started to point out some of the island's landmarks. After a few minutes, their conversation was interrupted by a beeping sound. Jessica went over to the computer on a side table and read something on the screen.

"Tim, sorry about this but you are to report to suite 768. You will find it on the top floor. I haven't had time to go through most of the rules, but in simple terms you must comply with any and all of the requests made by clients. This may well involve physical pain, you may only refuse if you are certain that something will cause you permanent damage. Refer to clients as 'Mistress' and when in doubt kneel before them. If I haven't got a date this evening I can fill you in over dinner. The handbook has a lot of information in it, so you had better read it carefully."

With that Jessica left. Tim realised that he was now beginning his new career, he wondered if he would make the grade.

~

Tim knocked on the door of suite 768, he wasn't sure but decided to kneel to be on the safe side.

The door was opened by a lady dressed in a casual plaid shirt and denim shorts. 

"Is that Tim?"

"Yes Mistress."

"Well come in. Thank you for coming so promptly."

Tim got up and followed her into the room. He was again conscious of the fact that he was only wearing a brief bikini. Tim was immediately struck by the size of the room, his was large but this was huge. He saw it had a wonderful sea view.

When the lady motioned that he should sit down, Tim perched on the chair, he was terribly nervous.

"Hi, I'm Melissa. I believe you are new to this."

"Yes, Mistress."

"So you haven't even been on the training course."

"No, Mistress. It starts tomorrow." 

"I suppose this is why Astrid said you were 'on the house'." 

Tim immediately calculated his income from the date, thirty per cent of nothing is not much!

Melissa told Tim to get a beer and join her on the balcony. Melissa was leaning on the balcony looking out onto the Mediterranean Sea, it was a truly stunning view. They chatted. Melissa started asking Tim about his background. God, this was not something he had prepared for, there was no way he was going to tell the truth about being kidnapped after carrying out a major fraud. On the spur of the moment he came up with a story about being made redundant from the City and a friend recommending Cartwright & Palmer. He was not sure if Melissa believed the story, anyway she let it pass. He would have to prepare something much better before his next date.

Then he felt Melissa's hand squeezing into his bikini bottoms. What was he meant to do now? As she was wearing jeans he couldn't reciprocate. Jessica was right, there was an awful lot more to being a whore than meets the eye. In desperation Tim rested his hand on Melissa's bum, waiting with bated breath for a cold rebuke, and an official complaint and all that it would entail. He then worried he was not been forward enough so started to massage the area between her legs. He felt Melissa begin to spread her thighs, clearly his attention was welcome.

Melissa gently pushed Tim away and put down her glass. Tim stood in the middle of the room, hands by his sides wondering what he should do. He wasn't exactly afraid, though he knew Melissa might 'punish' him, he was just scared of doing a bad job, he wanted her approval. He suddenly remembered Jessica's advice, "If you have a dom and are in doubt, kneel."

Tim was just about to follow this advice when Melissa said "Please take up 'the position'."

Tim was bemused but suddenly remembered what 'the position' was. He quickly removed his bikini bottoms and knelt naked on the floor, thighs spread and hands behind his back. He hoped Melissa was not getting irritated at the delays in complying with her orders, he really was trying.

She left him kneeling naked and went off to change. She quickly stripped and struggled into some brief shiny black rubber shorts and a matching short sleeved top. This came down just below her breasts and as ever it was a battle to get them in. The top left her entire midriff exposed, showing her beautifully toned body. She finished things off with some boots that came up to the top of her calves, (God did the laces take some time to do up) and a metal collar.

Returning to the main room she saw Tim had not moved. He looked great. She really wanted to show him off by parading him naked around the hotel, but this was frowned on. The only time slaves were meant to be naked in public was when they were being officially punished. This could easily be organised by dialling 119 on the internal phone, but Melissa wanted Tim for herself. In the end she told Tim to put his bikini back on.

"Tim, we are off to have some fun. When we are together you will walk one pace behind me. If I stop to talk to anyone, you will immediately get down on your knees. You will not speak unless spoken to." 

Melissa seemed to revel in the attention she was getting in her latex outfit; she looked great and knew it. Tim followed her being happy to gaze at her perfect bottom. Approaching the lifts Melissa was greeted by a bearded man in a Hawaiian shirt and shorts. Tim was alert and quickly got to his knees.

"Melissa, on the way to the basement? Who have you got with you? I don't recognise him."

"Hi Hubert. Tim is new. Tim stand up and show yourself to Hubert."

Tim rose and turned around. As he did so Hubert grabbed his bikini bottoms and pulled it down. Tim tried desperately not react as Hubert stroked his bottom then played with his penis. "Nice arse, very nice. I will have to have some of this. You said his name was 'Tim'. I assume he is on the system." 

"I am not sure his details have yet been uploaded as he is new. Anyway Hubert, I had better be going. Will you be in the Manhattan later?"

"As always, see you then. Bring young Tim along if he can still sit down!"

With that Tim pulled up his bikini and followed Melissa down to the basement. They approached a receptionist and were directed to "Dungeon 12". The name was not terribly ambiguous and Tim had more than a suspicion as to how he was likely to spend the next hour or so.

When they entered the dungeon Tim saw a mass of chrome and black leather. He had never seen anything like it. It had a sobering effect, this was serious. Melissa would only have brought him here to cause him pain. Tim wondered if he could stand it. He would try, try very hard in that there was something in Miss Christensen's manner that said he would not enjoy a second disciplinary session.

"Tim, the position."

Tim took off his bikini and knelt down.

"What were you told about serving clients?"

"I was told to comply wish any of your wishes, Mistress."

"That is only part of the story. You must not only submit, you must want to give me pleasure, to do everything you can for me. You must submit not just with your brain but with your heart and soul. You will serve some truly amazing women whist you are here, so you should be able to submit. They will be more intelligent, wealthy, attractive and desirable than you are. Now start by licking my boots."

Tim got down on all fours and started to lick, as he did so Melissa lifted her foot forcing the boot into Tim's face with increasing force. "Lick, scum." Tim increased his efforts to avoid Melissa's displeasure so early in the session.

"Tim, you should have been licking and sucking as if your bloody life depended on it, not giving the sort of kiss you gave to your first high school date. You have a lot to learn young man."

Tim redoubled his efforts, licking up and down with all the vigour he could command. The boots did not taste of much, just a vague plasticy tang. But Tim felt the warmth of Melissa's legs through the PVC. He was finding it hard to produce enough saliva to continue his licking. Tim therefore decided to start licking slower but with added ardour. Melissa raised her foot and forced her stiletto into his mouth. She tried not to show it but Tim was good, his arse swayed beautifully as he moved from one side to another. He really was trying.

After an age Melissa said "Tim, that was not good enough. You had better improve. Being punished after five minutes of your first session is pretty poor. Get over by that bench and bend over."

Tim quickly got up and did as he was told. He felt the piercing pain as Melissa hit him with a three foot long leather paddle. Tim squealed loudly.

"Silence slut. Now when I say bend over I want you to concentrate. That means spreading your legs and forcing your bottom out."

Tim immediately tensed his body. He got up on his tip toes and forced his head firmly into the bench so his bottom rose at a steep angle. Melissa was impressed. It was beautiful.

She proceeded to hit him backhand and forehand with the paddle. She knew the paddle would cause a lot of pain, but being a couple of inches wide would not cause any permanent damage. Tim's arse just looked so good. She hit him again and again, she knew she should stop but it was so inviting. After her admonition Tim kept silent. Melissa saw his face and the pain he was taking and the effort he was making not to cry out. Eventually Melissa mastered her lust and stopped whipping Tim.

Melissa now told Tim to stand and clasping him by his penis she guided him to a padded bench. She stooped and buckled his ankles into a pair of cuffs which were attached to some long chains. She then buckled a wide belt over his stomach and attached his wrists to the stool's legs. Melissa then retreated and wound a winch, this gradually tightened the chains and then began to raise Tim's legs, spreading them further part as it did so. Soon Tim was resting on his back with his legs spread wide above him. Now Melissa really had him at her mercy.

Tim had never felt so absolutely powerless. His legs were stretched apart so his penis and buttocks were totally exposed, with his hands being secured he could not defend himself in any way. 

Melissa picked up a riding crop and started playing with Tim's cock, flicking it one way then another, not hard but just to show she was in total control. Melissa then reached and started to rub Tim's penis, which rapidly became erect. Now she started to beat it harder, short rapid strikes, the crop hurt. Melissa loved watching Tim's penis being hit first left then right. Eventually Melissa saw she was causing Tim almost unendurable pain and left off, though Tim would have been hard put to know if this was a real escape or not.

Melissa put her hands on Tim's calves looking down on him, "Tim, you will have to get used to people taking you from behind. Dominants love seeing boys submitting in this way. I am no exception." She then rested her strap-on dildo between Tim's legs so he could see what was coming. Tim was surprised at how gentle Melissa was as she lubricated his arse, initially she simply massaged the opening, Tim was surprised but this felt great, as his anus gradually opened she put first one finger then two and finally three inside all covered in generous dollops of lube.

When she had finished she quickly lubed the strap-on and went to work. Melissa loved the feel as the dildo hit her clitoris. She adored the sight of Tim submitting. He did not complain but was clearly very uncomfortable, she wondered how much of the discomfort was physical and how much mental. He was now finding out about how boys had to submit and what it was like to be her plaything. The constant rhythmic pounding of her pussy made Melissa very hot. She also found Tim's pain and humiliation hugely erotic. When on the edge of an orgasm she stopped. So much more to do before she allowed herself a climax. 

Melissa smiled, this was so much better than she could have hoped for, but she still had a lot of fun to go. She detached Tim's ankle cuffs from the chain and clipped them to the feet of the bench, so his legs were still spread and his cock available. She then picked up an indelible marker, crouching she wrote 'Melissa's slut' just above his penis. She thought his bikini should just about cover the writing, but didn't much care if it didn't. Melissa knew that Tim would spend a good deal of his introductory course naked so wondered what his fellow students would think. She reasoned that if Tim scrubbed at each night it should be pretty invisible by the time he came to serve other clients the following week.

Tim was trying to recover from the pain, when he felt Melissa removed her top and straddled him. She sat on Tim's stomach and started to massage his nipples, initially gently but then with increasing vigour, until she was viciously pulling them one way and another. Melissa saw Tim's face crease with pain, but he did not cry out. After about five minutes of this, Tim's nipples were very red and hard. Melissa then took out some rather elegant circular nipple clamps and clipped them on. She smiled as she saw Tim wince with more pain. Melissa then edged down Tim's prostrate body and pushed one of her tits into his face and said "Lick." Tim now had the perfect opportunity to get revenge for the hell that his nipples had been through. Even the smallest bite would cause his tormentor great pain. Melissa knew it was a risk. In fact the thought of revenge did not even cross Tim's mind, all he was thinking of was how to lick Melissa's nipples in as erotic manner as possible. He wanted to give her pleasure. This he did, he sucked and licked alternating between the lightest touch of his tongue and sucking the entire nipple with all the force he could muster. Melissa felt wonderful.




Tim Ch. 02



This story continues on from "Tim Ch 1 -- Tim & Jessica are forced to work as submissive sex slaves.". This chapter works as a stand-alone story. 

*

Miss Christensen sat down to do her monthly reports. Jessica had proved a great success. She was pretty, liked her sex and had adapted well to the discipline, taking her punishment without complaint. Clients loved her. Miss Christensen remembered she had been a call-girl in London, a good start but still some call-girls found it hard to adapt to the beatings and the requirements of being submissive. Mr Cartwright had a soft spot for Jessica; he would be pleased that she was doing well.

Miss Christensen was less sure about Tim. He was handsome, almost pretty, and so far he had served clients well. They liked his innocent androgynous looks and waif like body. But he had resisted initially and she was unsure if he had been properly broken. She felt there was a risk that he would rebel in future. If he did Miss Christensen had a simple plan; immediate and extreme pain. Not subtle but she had to ensure he knew that he was a whore, merely a rich lady's plaything and had a duty to obey. Miss Christensen vowed to break him, no matter what it took. She was confident that if she could train him, he would make an excellent submissive prostitute.

For the first couple of weeks she had not put Tim 'on the system', having decided to sell him as a 'teenage virgin' to selected well-heeled clients. She had her stylists go to work on him so as Tim appeared to be an eighteen year old. When a potential client was identified, he was brought into her office in a collar marked 'virgin' and some brief black knickers. A member of staff posed as his mother who explained that Tim wanted to work as a prostitute and she was not going to stand in his way. He was fully trained and understood the punishments he would have to endure and the sexual services he would have to provide. She only asked that as his first date, the customer would be gentle with the poor boy and make allowances for his inexperience. She ruffled the hair and patted the thigh of her seemingly nervous (and almost naked) 'son'. Miss Christensen managed to charge a number of clients super-premium rates for taking his 'virginity'. Tim seemed to act the enthusiastic, naïve boy extremely well and clients were overjoyed with the experience. Soon he was 'on the system' and earning his keep as one of the junior whores.

After Tim and Jessica had been on the island for about a month, Miss Christensen announced, at one of her routine weekly briefings, that the next 'school' party would be the following month. This announcement seemed to cause great excitement. They were quickly filled in on the details. The island hosted such parties four times a year. They involved all the whores dressing up as schoolboys and schoolgirls and the whole island being transformed into a school. Most of the whores were in their early twenties and made no attempt to appear younger, the attraction was the outrageously sexy uniforms and the party atmosphere. The events were hugely popular with the clients, which made them very lucrative. The demand was such that Cartwright & Palmer imported whores in from other offices, mainly London and New York, to cater for the demand.

As the date came closer Tim was required to help with the preparations. This mainly involved converting some of the dungeons into school rooms and opening up the bespoke school buildings; these housed the showers, dormitories and changing rooms. 

A week before the first guests arrived everyone was issued with their uniforms. Both boys and girls were to wear white satin shirts buttoned at the wrist and neck along with a dark blue striped tie with the colour of the stripe indicating the whore's grade. Girls wore a very short black satin pleated skirt and the boys tight black satin shorts. The only non-school item of clothing was lingerie, they were all permitted to wear their normal knickers.

Everyone was photographed for the 'yearbook' (available on-line or for $85 at the island's shop). The top of the page was pretty standard; the girl or boy in their school uniform, their age, statistics, grade, orientation (about 95% said bi-sexual) and education (there were a number of degrees and even two doctorates on the staff). The bottom of the page was less conventional as it had photographs of the person naked along with the sexual services they offered.

Tim had already been photographed for his web page. Shots had been taken fully clothed, in swimwear and a couple of shots of him naked lying on a fur rug showing his delectable bottom; all quite tame. For the school photographs Cartwright & Palmer brought in their official photographer, 'Chiara Salvadori'. Tim dressed in his school uniform and presented himself at one of the dungeons that had been transformed into a studio for a few days. Chiara was a slim beautiful woman, probably in her mid to late thirties, with her dark hair swept back in a pony tail. She certainly had a presence and a natural authority that Tim found slightly surprising in view of her slight physique.

"Tim, let's start with you leaning against the wall ... pull up your shorts I want them to look tight." Chiara took shots from various angles of him in his uniform. "OK, shirt off ... arms across your chest ... smile ... bend over ... kneel ... up you get ... now take your shorts down ... slowly." 

Tim was now down to his brief black knickers, "Good, let's start with your arms across your chest ... now, hands behind your back ... turn around, and bend over ... kneel down, hands in front of you ... eyes down, look embarrassed ... lay down on the bed ... and pull your pants down just a little ... thank you."

"Up you get, now lower your knickers ... hold them mid thigh ... strip naked for me ... perfect ... spread your legs more ... look natural ... turn around, show me your bottom ... on your knees." All the time Chiara was shooting away.

Chiara handed Tim a pot of cream and told him to cover himself with it. She said it would stop his skin reflecting the bright photographic lights. Initially he rubbed some on his face then his arms, and gradually went down his body, missing his pubic area. Tim began to enjoy massaging himself, although he would have liked some privacy. He did his back and finally his bottom. Chiara warned him he had to do all his body, as any bits he missed would reflect the light. Taking the hint, Tim turned away from Chiara as he rubbed it into his penis and between his legs. Looking down he saw he had a huge erection, the cream made his skin tingle, it was a very erotic feeling. Tim gave himself a last once-over to ensure he was really complete, he was enjoying this. Chiara was enjoying taking the photographs. She knew the cream would get him very aroused, so he would loose any inhibitions he might normally have. It should make it much easier to get him posing in the nude and to agree to some pretty explicit scenes she had in mind. 

Chiara took photos of Tim naked from the front, then back. She then had him coyly trying to cover himself with his knickers, bending over, pulling his buttocks apart, in 'the position', on his back with his legs spread and finally on all fours. Most of the poses she wanted Tim to be relaxed, but sometimes she had him erect. Tim simply obeyed, smiling depending on Chiara's instructions. He had been under Cartwright & Palmer discipline long enough to know not to complain, anyway he was rather enjoying it.

"Now for the fun. Get on all fours ... let's start with the dildo ... please insert it." Chiara handed Tim a large black dildo and tub of lube. Tim did as he was told despite the dildo being considerably bigger than he was used to, and eventually he inserted it to Chiara's satisfaction. Chiara photographed him on his hands and knees then lying on his back playing with the dildo. All the time Chiara was giving Tim instructions, "Come on try harder. Tim I want to see that dildo all the way up." Tim was sweating as he tried to get the dildo into his anus, it was really huge, he would like to see Chiara do this. "Keep yourself erect ... keep pumping ... faster ... I want a look of ecstasy ... legs wider, really spreads those legs ... now I want some close ups of you sucking the dildo ... deeper ... perfect."

Tim knew things were getting a little heavy but was feeling hugely horny so was happy to follow Chiara's instructions. "Susan your turn now." A pretty naked girl walked over. Tim had never met her and it seemed they were going to do a photo shoot without being formally introduced. They started with them in an intimate embrace but quickly moved to sex, first in the missionary position, followed by doggie. Any thought of simulating it had long been forgotten. Chiara wanted it 'hard and dirty'. She had Tim lie on his back as Susan gave him an (excellent) blow job. Finally she had Tim lick Susan's pussy. All the time Chiara was taking photos from all angles.

"Tim almost done, we just need you to pose with on the St Andrew's cross and a few other bits of equipment." Chiara buckled him onto the cross, and took photographs of him from the front. She then turned him around and secured him. The restraints were tight and Tim couldn't relax. When fully secure, Chiara picked up an old fashioned cane and hit Tim four hard strokes on the buttocks. "Tim, sorry about that, but the stripes across your arse look wonderful." Susan returned, now dressed in PVC underwear, suspenders and boots. She posed spanking Tim over her knee, standing on him and whipping him with a riding crop. Lastly Chiara had Tim kneeling licking Susan's boots.

Tim was tired and felt abused when he was finally released. Chiara seemed to enjoy ordering him around stark naked and intentionally humiliating him, by the end she was calling him 'slut'. He thought she must have taken hundreds of shots; she could produce an entire pornographic book rather than 'a couple of shots for the website' as she claimed. Even so, Chiara told Tim she wanted more, he was to be at the 'Kusiemski pool' at 11am the next day for the outside shots.

Tim presented himself as ordered. Chiara got Tim to strip and massage his skin with coconut oil so it was glistening. She recorded Tim's progress. She then took shots of him in his bikini lying down, back and front. She got him to untie the sides and took shots where Tim was covered but only just, he was meant to look very 'available'. She took some photographs of him walking by the pool, swimming and in particular just getting out of the pool. She repeated this process with Tim wearing a tiny pair of trunks and finally naked. She took a lot of photographs of him naked; lying on his front and back on the lounger, spreading his legs and kneeling on the lounger showing off his pert bottom. Then walking by the pool, casually carrying a bikini and finally more photos of him swimming. By the end of the session Tim had quite an audience that Chiara did nothing to discourage. The next day Tim arranged to see Chiara. He was embarrassed as he felt the first session in particular was very explicit. He shuddered when he remembered some of the poses he had been in. What had he been thinking? He hoped he could persuade Chiara to junk some of the most salacious shots. This said, he knew some good photographs could lead to a great increase in the 'dates' he was booked for. Chiara showed Tim the selection she had chosen for his web page with some pride, but declined to remove any, despite Tim's entreaties. ~ The first yachts started arriving on the Wednesday evening but most of the guests arrived on Thursday when management provided an efficient shuttle service from a couple of private landing stages on the mainland. All guests were met by a whore who carried their luggage and made sure they were comfortable and if they were new to the island showed them around the resort.

Tim had been booked for the initial date by a lady called Christin von Eberstein. He was told she was to be arriving at 11am on Thursday and he should present himself at the marina to greet her. As the booking had been made well in advance Tim had the opportunity to ask around to find out about this Eberstein. He was told she was a beautiful German lady. When she was in a good mood she could be quite charming when irritated she could be a complete bitch, taking great pleasure in humiliating her whore and causing them great pain. She demanded constant attention and respect. 

The meet up was easy as Christin had seen Tim's photographs. Tim was keen to make a good initial impression so immediately dropped to his knees. He then carried Christin's luggage to the hotel complex.

Whilst Tim unpacked Christin's things, Christin went out on the balcony to admire the view. Although nothing had been said, Tim could feel the massive sexual tension. When she thought Tim was not looking Christin rubbed herself producing a rather attractive soft pink flush.

"Tim, the position."

Tim stripped naked and got down on his knees, it was important to get off to a good start especially for these longer dates. After all he had been warned not to take any liberties.

"Tim, I have been to the island on several occasions, but this is the first time I have managed to make one of your Schoolboy parties. We have a school room booked for 3pm, before then I want you to take me around and show me the 'sights'."

Tim started his tour with the games rooms. There was a girls' basketball game being played. The girls wore very revealing outfits. Tim explained that their outfits all had their personal number on them in the same way that girls' uniform skirts and boys' shorts did. So if a client liked the look of one of the players they could be booked. Christin was interested and seemed to have eyes for a tall Brazilian playing in defence, her lithe frame hid a formidable physique.

Tim then showed Christin the gym. As well as the normal weights machines and treadmills there was an area where they saw a number of female whores practicing their floor exercises. It always amazed Tim seeing how flexible some of these girls were. He saw one girl doing a slow perfect splits. All the girls had their numbers embroidered on their leotards. Tim showed Christin a keypad so that observers could summon any of the whores they liked the look of. Keying in the number 20 Christin sent for a girl called Nadia. Nadia seeing her number immediately stopped her exercise and rushed over, falling on her knees before Christin. Nadia was a professional athlete before she came to Cartwright & Palmer, representing Russia at the Beijing Olympic Games. She had continued with her punishing exercise schedule and Tim thought she had the most perfect body he had ever seen.

"Yes Miss, what can I do for you?"

"Let me see you in 'the position'"

Nadia stripped off her leotard and got back to her knees. Christin then asked her to stand up and turn around. Nadia did as asked, moving with her normal air of serenity. After turning around she did a slow back flip, showing her grace and athleticism, after which she returned to 'the position'. Christin evidently liked what she saw as she left determined to book the girl. 

Tim escorted Christin to one of the resort's restaurants. As they waited to be seated Christin said, "Tim, lick my shoes." Tim got to his knees and started licking. Christin liked to do this sort of thing for many reasons; the first was the simple pleasure of humiliating Tim in public, then of course it showed Tim that she might treat him as an equal but that he should never forget his real status and lastly she could see how quickly the whore got to their knees. If there was some resistance or hesitation Christin knew that she the whore was probably second rate and she would have to start any session with severe corporal punishment to get the obedience she wanted. Tim passed the test.

When they were seated, Christin wanted to know about life on the island and how Tim found being a prostitute. She had looked at his web page and asked about some of the sexual services he offered, many of which were totally new to her. Tim gave Christin a 'sugar coated' version of life. To be truthful he didn't really know how he felt about his new profession, but he thought the situation called for light banter and a few amusing 'war stories' rather than an in depth confession. 

As they were drinking their coffee Christin handed Tim a pair of knickers and told him to put them on. Tim went to the back of the restaurant and changed, he struggled out of his shorts and then proceeded to put on the knickers. They were red with some subtle black lace trim. The difficulty was they were made of satin, lovely and smooth but with very little 'give', eventually he got himself into them and returned. Christin felt that these knickers were the best mementos of a successful date. She just loved wearing them later, remembering the fun she had had. She was wearing some pink ones that had been worn by a poor girl in London called Marie-Louise. Helen had told her that the girl liked it 'rough' and 'really enjoys pain'. Christin had spent a wonderful afternoon humiliating her. Christin remembered whipping her and forcing her to put ever larger dildos into her pussy and bottom. The girl could barely stand by the end of it. Marie-Louise must have been one of the most depraved tarts on the firm's books, she seemed to have no limits. Christin smiled as she remembered Marie-Louise dressed just in the knickers drinking from a dog bowl in the bar and how she ordered the poor exhausted slut to go to a neighbouring table and offer herself free of charge. The last Christin saw of the girl was her being led away stark naked by four men, doubtless to be rogered senseless. Oh how she enjoyed wearing these knickers and hoped the red ones would bring back similar memories.

After lunch, Christin sent Tim off to check the school room's number. She leant back and stared at his bottom, so beautiful in those tight satin shorts. She mused that there were a number of other agencies that could provide boys and girls as attractive as Cartwright & Palmer, but it was a submissiveness and willingness to please that really made these whores stand out. She knew that Tim would comply with any of her orders, no matter what they were, no ifs or buts he would simply do it. She could see that sometimes a whore might be deeply humiliated or in great pain but a Cartwright & Palmer prostitute never refused. Christin loved this obedience and was prepared to pay handsomely for it. The island seemed even better than Regensburg or London. 

As she cradled her wine she thought of what she was going to do to Tim. She had read the sexual services he offered and as ever was amazed and the number and variety. Over the past couple of weeks she had filled every waking hour with one erotic idea after the next, the list was endless. Now she had seen that Brazilian and that minx Nadia. What a wonderful thought, these two doing anything she wanted. Which should she take? A lovely dilemma.

After lunch they went to Cartwright & Palmer's shop. This huge room was in the basement of the hotel and about two thirds of the area was given over to various sexual aides, the rest to DVDs and magazines. Christin bought a couple of DVDs of Tim being tortured and humiliated by two of the in-house dominatrixes. She then looked through the clothes and chose a PVC corset and a tight wet-look skirt for herself. She bought Tim the sweetest little satin sailors outfit and a brief gold spandex bikini. She longed to see his embarrassment as she forced him to wear it by the pool. 

They walked to the whips section, the choice was incredible. "OK, Tim bend over I want to test a few of these." Tim bent over as he was told. 

"Oh come on Tim, shorts down." Tim wriggled out of his shorts and then acknowledging the inevitable took down his knickers. Christin practiced using a paddle then an old fashioned cane. Tim winced as the cane struck his buttocks, looking around he saw he had quite an audience. Eventually Christin decided on a cat and a cane.




Tim Ch. 02



Tim, relieved, reached for his knickers but Christin had other ideas. "No you don't Tim. I will need your bottom again before we are through." Tim saw one of the shop assistants coming over, he was worried that he was about to be bollocked as although whores were encouraged to dress provocatively they were not meant to be naked in public. It was always the whore rather than the client who was told off. The shirt's tails only just about covered his modesty. In the end the assistant only wanted to make a few ingratiating comments to Christin.

They came to the dildo section, a selection were on display in sterilising solution. Christin pickled up a huge vibrator. "Tim, spread your legs." Tim did as he was told he could not believe Christin was going to fuck him in public. He felt the slight sting as the sterilising liquid was wiped along his arse. He felt more pressure as Christin pushed. Tim tried to relax, but he knew this was going to be difficult. Christin eventually inserted the dildo and gave Tim a few hard pumps. The performance had again attracted an audience.

"So Tim what do you think?"

In truth Tim didn't have much of an opinion, one dildo was pretty much like any other to him but he wanted his humiliation to stop, "It's great Miss. I think you ought to buy it." Christin did not fall for this and tried two more dildos in Tim before deciding on a large red gel version as it would match Tim's knickers (when of course she allowed him to put them back on). 

When it came to gags Christin asked for the assistant's help. The shop assistant asked Christin, "Well Miss, do you want the gag for decorative purposes, to keep your whore silent or to cause maximum discomfort?"

"Well, I hadn't really thought. I suppose to keep him silent."

The assistant showed Christin various models explaining that nothing very new had come onto the market recently. She then pointed to a ball gag with a silver rubber ball which she said was quite fashionable. 

The assistant picked out a black gag in the shape of a large penis, "This is great for punishing slaves, it also improves a slave's ability to give blow jobs as they get used to taking the penis all the way down their throat." Christin picked up the gag, trying to hide her surprise at the size of the penis, could Tim really take this down his throat? There was only one way to find out. She gingerly eased it into Tim's mouth and eventually got it all the way down; the poor boy looked in great discomfort. Christin buckled the gag securely in place.

The assistant recommended the matching butt plug, "It's big but your slut looks as if he can take it. It's a really nice set and being penetrated by two cocks at once can really humiliate a boy." Christin liked the idea and told the assistant to try it out on Tim. Tim was prepared and now used to being fucked but the plug was huge. He stripped off his shirt and tie and bent over, trying to relax. The assistant lubed the plug and Tim's rectum with practiced skill, but they both knew it was not going to be easy to insert something this large. The size of the plug and Tim's efforts to take it increased the size of the crowd. He strained, pulling his buttocks as wide as he could, gyrating his hips to ease the entry of the monster. The assistant was putting huge pressure into forcing the plug in and out, trying to push it deeper with every stroke. It was hard work, but she could see it was worse for Tim, who was sweating profusely and in obvious distress, made worse by the gag. When eventually it was in place Tim was hugely relieved and almost insensible to an enthusiastic round of applause. On the end of the plug was a cute little bunny's tail, it made Tim's adorable arse look so sweet. Christin loved the set and bought it without any hesitation. 

Christin made Tim keep the plug and gag in for the rest of her visit to the shop. She gazed at Tim walking naked around the shop; she almost felt sorry for inflicting such pain and humiliation on the poor boy, but watching him turned her on terribly. She just loved torturing him, but seeing so many people staring at his nudity eventually she allowed her 'little bunny' to put some backless knickers on. His tail was still on display and his arse look beautiful.

Tim had noted that it had become increasingly fashionable for guests to keep their whores on a chain attached to a collar. Christin had also noticed this and her eyes lit up when she saw the collars on display. She had Tim model dozens before she chose a plain stainless steel collar. She decided that she would have, "The property of Christin von Eberstein" engraved on it. 

There was some embarrassment when Christin came to pay for her purchases as she could not remember the size of the butt plug. She had her 'little bunny' bend over, spread his legs and his clasp his buttocks so the shop assistant could read the bar code on the end of the plug. When this was sorted Christin allowed Tim to put his uniform back on and remove the gag. They then left casually chatting. 

Christin sent Tim to one of the school rooms whilst she returned to her room to change. Tim took the opportunity to remove the butt plug, he felt a huge sense of relief. Christin returned dressed as a 'teacher', this involved a white satin shirt and a latex micro skirt. She looked fantastic, the get up showing off her figure and particularly her long legs to their best advantage. Tim thought back and admitted he could not remember that number of his teachers wearing such a skirt but it was not his place to comment. 

Christin sat down in one of the easy chairs and looked at Tim with a severe expression, "Come on my little bunny, strip down to your collar and panties."

Tim did as he was told, slowly removing his tie, shirt and shorts. Christin said nothing, just staring at him. Tim hated people watching him undress and Christin's insistence that he keep his knickers on was almost worse that stripping naked. She had clearly chosen them to humiliate him, they were very brief, being made of red satin with edgings of black lace.

"Bend over the desk." Tim did so, tensing his buttocks and legs to show himself off to the best advantage. Christin approached and stroked the tight satin, her hand then wandered between Tim's legs massaging his cock. She did this with a certain languor. 

Christin loved seeing Tim bent over like this, the red satin of his panties stretched taught against his buttocks, it gave her such a sense of power. The feeling almost sent an electric shock to her pussy; every step seemed add to her desire as her pussy rubbed against the latex of her skirt. She was feeling so incredibly horny.

Christin picked up the riding crop and started to whip Tim, softly to begin with but with gradually increasing force. Although Tim tried to stay silent, he let out involuntary yelps whenever Christin struck a hard blow. 

"Bunny, take down your panties, I want to see my handiwork." Tim slipped down his knickers revealing his buttocks criss-crossed with vivid red stripes. Christin continued to beat the now naked Tim. His cries of pain were so erotic. But despite the punishment he stayed leaning over the desk, just for her entertainment. Christin admired her boy, he was so damned beautiful and he was hers, she had to have him. Christin motioned Tim to her bed and got him to lie down.

"Now let's have some fun."

Christin struggled out of her latex skirt and then whipped off her panties. She tied her shirt under her tits and stood in front of Tim to let him admire her. Admire her Tim certainly did, she looked magnificent just dressed in her stockings and shirt, her midriff and partially shaved pussy on show. She had a great body and knew it. Tim was rapidly becoming excited. 

Christin crawled onto the bed. Tim knew a good prostitute always responded to their client's mood, after such a whipping Tim was expecting Christin to want some pretty rough sex. But he was surprised, Christin held him firmly but then kissed him incredibly gently, initially her lips barely brushed his. Tim therefore was careful when he penetrated her, so as to be as gentle as he could. His thrusts were slow and careful. Christin responded, gradually upping the tempo, increasing the pace. Soon he was fucking her with an animal passion. As she reached climax she screamed with pleasure. She had fucked her slave and it had been wonderful.

Tim felt Christin's head resting on his shoulder as she dozed in a blissful sleep. When she awoke the intoxicating smell of cum aroused her anew. She gave a Tim a gentle blow job, not really to excite him more to taste his cum. She then released him and had him take her in the doggy position. This time Alex clutched her tightly in his arms as they both dozed. Eventually it came time for Tim to leave, he dressed in his uniform and gave the still sleepy Christin a gentle kiss goodbye. 

As he left, he kicked himself remembering the Escorts' rule number one, never fall in love with your client. He knew this but he did so hope that Christin would choose him again. ~

As Tim returned, tired, to his room he was called by one of the 'teachers'. These were customers who had paid for the privilege of 'disciplining' any boy or girl they desired.

"You, come here." 

Tim approached as he was bidden, "Yes, Miss."

"Bend over."

Tim knew the score, he squeezed out of his shorts and let them fall to the ground. He then did the same to his knickers and bent over, legs straight, hands on his knees and awaited the inevitable. He felt the breeze on his exposed cock and buttocks. His nakedness was attracting an audience.

The 'teacher' smiled, gently raised Tim's shirt and proceeded to whip his bare bottom with a riding crop six times. After his punishment Tim pulled up his knickers and shorts and said "Thank you, Miss." He knew one session was not too bad but he hoped not to get caught too often.

Jessica was thinking the same thing. She had been caught four times in the last half hour and her bottom was now a very rosy shade of red. It was painful even for a reasonably experienced submissive such as herself. She couldn't keep on getting spanked, the best way of avoiding such regular punishment was to get a half or whole-day date. A date may involve some pain but this was likely to involve one session and be relatively short and sharp. 

Management always ensured that there were far more whores on duty than there were guests, this ensured that there was always great competition between the whores. Jessica wondered about how best to get the date she desired. She knew she could always sell herself at the 6 o'clock auction, the difficulty there was that if enough customers did not turn up she might find herself going for 99c. She thought about sitting on the low wall just outside the entrance to the dormitories. When she got there she saw that six girls were already sitting on the wall including one painfully gorgeous grade one. She thought of joining them, but worried the area might be on one of the teachers' beats. Jessica therefore decided to head for the communal showers. The idea was that girls and boys showered there after playing games, but Jessica knew no one would mind her having an extra shower. She stripped and put on her collar so clients would know she was available and her grade.

Jessica stood under the powerful cascade of water luxuriating in the massage this gave her. The shower seemed to reduce the pain of the spankings and she quickly forgot the reason for originally coming there and started to enjoy herself. She was brought back to the present when she feel a hand gently to massaging her bottom. She began to turn, she knew the next few seconds were important. She wanted to 'land this date', in particular she hoped it was not some opportunistic whore or a time waster client. She smiled her most alluring smile and saw her admirer was certainly a client, he looked the CEO type, averagely handsome but well put together with obvious charisma. 

Jessica pressed her body lightly against his. He did not pull away so she pressed her pussy against his thigh, knowing he would feel her warmth. He did not say anything, he merely took her hand and steered her out of the shower. She dried herself, put on her shirt and tie and without knickers or skirt started on her hair and make up. When she saw he was ready she wandered over and finished dressing.

"Hi, I'm Simon. Would you be able to keep me company for the next twenty four hours?"

Jessica's heart jumped, this is exactly what she was hoping for, "Yes sir, that would give me great pleasure. My name is Jessica."

"OK, Jessica take your knickers off. You won't need them for a while."

Jessica quickly took off her panties and handed them over. It was odd, she was so used to being naked in front of customers but walking around without knickers still felt very unnatural and rather decedent. More so because she was so perfectly shaved, she felt cold. As her skirt was so short she suspected her nakedness was not a total secret to those she and Simon passed on the way to the hotel complex. Perhaps Simon was thinking along the same lines and to ensure there was no uncertainty he got Jessica to bend over to pick things up at regular intervals exposing her ever so bare bottom. 

On entering his room, Simon immediately told Jessica to open her mouth and pushed her panties in. He sat down and told Jessica to lie on his lap. Simon started by raising her skirt and stroking her beautiful behind, but before long began to spank her. The strokes were getting quicker and harder as Simon got increasingly excited. Being spanked was an inevitable part of being a school girl, but Jessica was in real pain. She screamed but with panties firmly wedged in her mouth only the quietest mumble could be heard, not that Simon was interested he was in "the zone".

Eventually Simon seemed to get tired and he first slowed then stopped. He then slipped his hand between her legs and started to stroke her pussy. Jessica's body was in overload, first pain now pleasure. She squirmed as his rubbed her clitoris. He then forced his fingers into her pussy entering her with increasing force. Jessica gasped, her pain forgotten, she was now wild with desire.

"OK, Jessica, put on these wrist and ankle cuffs and sit on the bed."

Jessica did as she was told, feeling renewed pain as she sat down. She pulled up her skirt, spread her legs as far as she could and awaited Simon's pleasure. Simon clipped her wrists to a hook above her head and her ankles to the bed board about three feet apart. Jessica was now firmly secured, legs spread and pussy totally exposed and defenceless. Simon surveyed his handiwork then stripped and quickly entered her with the barest minimum of preparation. The fucking was brutal, this was basic and animal sex, no love or gentleness Simon thrust with ever increasing force. Eventually he came with a shout of ecstasy. After his climax Simon slept, leaving Jessica secured, cum all over her. 

Jessica was still in her, now ragged and stained, uniform; her was makeup smudged with streaks of sweat, she looked a sight. On waking Simon told Jessica to get some clean stockings, suspenders and panties as they were going to dinner. Simon dressed in an immaculate dinner jacket and waited as Jessica did her make up, she put on her underwear and entered the main bedroom. She hoped Simon would let her wear her evening dress or even her uniform, but she was disappointed.

"Good, Jessica you look wonderful. Let's go."

Simon escorted her down to the lifts. Jessica tried to look relaxed as she walked down the corridor. She was proud of her body, in particular her pert tits, but still felt very naked seeing couples in their elegant evening dress. When they arrived at the lifts they met a lady who seemed fascinated by Jessica's breasts and with Simon's permission stroked and squeezed Jessica's nipples. She then asked Simon about Jessica's sexual prowess as if Jessica wasn't there. Jessica was very conscious that the livid red stripes on her bottom were very visible; the brief satin panties giving almost no protection. Simon made her bend over and take down her knickers so the lady could examine her bottom in intimate detail.

On arriving on the third floor Jessica tried to quickly pull up her panties. The lady went to the right and Simon guided Jessica to the left. They headed for the 'Graziani's'. As they entered Jessica saw a discreet sign 'All patrons are respectfully asked to wear knickers at all times', as Jessica looked around she saw this was about all many of her fellow whores had on.

They were steered to a table in the centre of the room. After Simon's rather brutal treatment of her so far, Jessica was surprised to find he was a delightful dinner companion. She very much enjoyed his light self depreciating wit and laughed, totally forgetting that she was topless and had an aching bottom. After the second cognac Simon said they had better be going. 

One of the main attractions of the weekend was the dormitory block. This was a specifically designed building that consisted of four dormitories, one all male, one all female and two mixed, each having about thirty beds. Every dormitory had a wash block attached, in the centre of which was a block of basins, on the right shower cubicles and on the left a communal shower area. Whores were, of course, obliged to wash in the latter.

Simon had booked two beds for the night. Jessica found her single bed and stripped, she then went to the shower and washed carefully making sure Simon had a good view. Returning to her bed she dressed in the standard night shirt. This was pale pink satin for girls and pale blue for boys. It had was short coming down to mid thigh, had long sleeves buttoned at the wrists and was buttoned at the neck with a small delicate collar. Looking in the mirror she knew she looked terribly innocent and vulnerable. Even she could admit that the innocent bit was not a real reflection on her moral character. When she had dressed she joined her fellow whores doing the sort of thing school girls did before bed. She shaved her bikini area, lubed herself then read a romantic novel.

The lights flashed on and off indicating 'lights out' would be in five minutes. Jessica looked at her bedside table, with the normal schoolgirl accoutrements; alarm clock, teddy bear and ... a dozen condoms, lube and a twelve inch gel vibrator.

Jessica's mind wandered and she thought back to her time in Diston, how a week after her eighteenth birthday she approached the local brothel asking for a job. Mrs P took her on a probationary basis telling her she should, "Be attentive, willing, available and fuck like a bunny." When the lights went out Jessica got out of bed, she pulled her nightshirt up to her neck and spread her legs. Jessica then gave her clit a good rub. She felt ready. She thought Mrs P would concede she looked pretty 'willing and available'.

Simon told her to kneel on all fours on her bed. Jessica did as she was told, spreading her legs as far as she could. This time Simon was more gentle as he took her anally. After Simon had climaxed, he dismissed Jessica. As she got into her bed she felt tired, she felt she had well and truly earned her money that day and had a very sore bottom to prove it. There were still a number of couples hard at their stuff, a tired Jessica went to sleep with her teddy bear to the cries of ecstasy as her colleagues worked into the night.

Jessica woke the next morning to her neighbour's sighing. Sex at seven am! Jessica got up and got a cup of coffee for Simon. She sat on his bed as he drank it, offering herself to him. Simon thanked her but explained he had to leave on the first flight so declined.

Jessica went back to her room. She felt she could relax for a couple hours and then try to get another date before lunch. 




Tim Ch. 02



~

When Tim got back to his room he immediately stripped off, stood in front of his full length mirror and looked at the damage. Christin was a wonderful person but she had given him, quite a beating. He was proud of his body, his bottom was a rosy shade of red and hurt like hell, but there was no blood. All whores hoped only to have one beating a day, but Tim had endured two, three even four without permanent damage. He rubbed some pain relief cream into the worst affected parts and looked to see how long he had until his next booking; three hours, could be worse. Tim grabbed his book and lay down on his balcony, time for some real relaxation whilst his body recovered.

After a light lunch, Tim went to Restaurant Condé situated on the east coast of the island. He had been booked for the afternoon's game of 'La Chasse'. When he arrived he was issued with his kit; light Wedgewood blue latex shorts and top. The shorts were short and tight; the top was short sleeved and cropped so his midriff was exposed. The outfit had been modelled on female athletes' running kit. The girls wore something similar in pale pink. 

The changing room had glass walls to allow clients to watch the whores as they changed. When Tim realised a couple of ladies were watching him, he ensured he was naked for as long as possible. This was a great way of attracting a client. Tim slowly stripped out of his uniform before picking up his latex outfit. He didn't really need to try extend the process as it took an age to get the latex shorts and top on. The things were so tight, but Tim knew it had been worth the effort when he looked at himself in the mirror. He shouldn't have any difficulty in getting a date dressed like this.

When he had finished he joined the rest of the whores and the clients in the restaurant. The crowd went quiet as Miss Christensen entered the room, "Can I please have your attention. I realise most of you have played 'La Chasse' before, but let me go over the rules for any newcomers. In simple terms it is a hunt. Clients, or 'hunters', aim to shoot as many whores as they can. Whores obliviously must try to avoid being caught. The game goes on for ninety minutes. Whores can go anywhere in the Condé gardens. If shot, whores must return here and wait for their new owner. Hunters please try not to shoot whores in the face or genitals. If a hunter manages to shoot more than one whore they can sell any they don't want at the drinks party that we will be having here after then end of the hunt. If a whore avoids being shot they are free to sell themselves at the party. Lastly remember than one of the whores has a Cartwright & Palmer silver sovereign in their knickers. OK, whores off you go you have a five minute start."

Tim headed for the exit, he thought there were probably about twenty whores. He wished he had thought about tactics in advance. It seemed one could either rely on speed and agility and run from the hunters or one could hide. The Condé gardens were lovely, Tim thought they must be two or three acres set out like an English park with a manicured lawn, decorative lake and a couple of small woods and they provided a fair amount of cover.

Tim always favoured the counter-intuitive so when he saw his fellow whores running down the hill trying to put as much distance between themselves and the hunters as they could, he decided to do the opposite and rushed to find a hiding place close to the restaurant. He quickly found some long grass and laid down. He hoped to have a boring ninety minutes as he could not see if hunters were approaching without giving himself away. After twenty minutes Tim was dozing, all he could hear were a few isolated screams of excitement and sometimes pain. No hunter had been close.

Eventually Tim heard the footsteps of an approaching hunter. He wondered if he could risk raising his head to see if the hunter was coming in his direction and if they were, making a break for it before it was too late. Tim knew he had a decent turn of speed but a paintball travelled at about 300 mph, rather more than Tim's best. As he was close to the fence he could only run left or right making him an easy target. There was nothing to be done but hope and wait. Tim tried to flatten himself in the unresponsive earth, he held his breath and prayed.

But it was no good, as Tim looked up he saw a hunter staring down. Tim was about to surrender when he felt intense pain in his buttocks and back as the bastard shot him a dozen or so times. 

"OK, up you get you whore. Shorts down." Tim got to his feet and automatically dropped his shorts, not that easy as they were latex but he managed it. The hunter felt Tim's penis and looked inside his shorts. Tim realised he was looking for the sovereign, but without success.

"Right, go back to the restaurant. Tell them you were shot by Olivier, number eight." With that the guy ran off clearly determined to add to his haul. As Tim wandered back he felt the yellow paint ooze down his shorts and thighs.

Tim was gratified to find that he was not the first to have been shot. Miss Christensen met him, and after asking him how he enjoyed the game told him to shower and put his uniform back on. He was given a tag to wear that had Olivier's name and he assumed his telephone number stamped on it.

The siren went off, indicating the end of the game. The hunters and the whores who had not been caught gradually returned. When Olivier entered the room, Tim and Angel, who he had also shot (this time aiming for her pussy), approached and knelt before him.

Olivier read their names from the tags, "Tim, you are the first boy I have shot. What can you do for me?"

"Master, everyone should try a boy. I am very willing and enthusiastic. I will give you a great time I promise. I give a great blow job."

Olivier smiled and started to stroke the front of Tim's satin shorts. Tim quickly became erect, "Thank you Tim. You make it sound very inviting. As you say I really should sample a willing boy. But I am afraid Angel can do things no boy can rival. So Angel, you will be my guest for the rest of my stay. Tim, I propose to sell you." 

Tim felt strangely humiliated by this rejection, but quickly got to his feet and scurried away. Whores who were for sale were told to help serving the drinks. The idea being to give as many of the clients a chance to see them (and potentially make Olivier an offer) as possible. Tim put on an apron and got to work. He had no idea if anyone was bidding for his services as lots of clients seemed to be on the phone. Tim suspected the hard bargaining was not for cash per se, but it allowed the sellers to play the pimp, an erotic and unfamiliar experience for most, if not all, of them. Tim looked with envy at those whores who had avoided being shot. They looked so damned sexy in their tight latex shorts and cropped tops, they would have little difficulty in selling themselves again. Tim looked round and saw Claudia laughing with a potential client, she was struggling out of her top and shaking her beautiful breasts, who could resist that? 

After Tim had been serving for about half an hour, Olivier called him over. "Tim, come here. I have sold you to Jinx."

Tim looked at his new Mistress. A well proportioned lady in her mid forties with blond hair in a pony tail. She was wearing a short black latex skirt and a white roll neck that showed of her breasts to good advantage. She was clearly making some efforts to look younger with some success. She was toying with a riding crop, gently tapping her thigh. Tim wondered what she would want from him. "Hello, Miss. How can I serve you?"

Jinx smiled wickedly, "You will find out, my boy."

When they got back to Jinx's room she immediately turned to Tim and said, "The position, now."

Tim stripped naked, put on his slave collar and knelt on the floor. He was worried about the harsh tone of his Mistress's voice.

"Tim, I am going through a very nasty divorce from a very nasty man. The thought of having a handsome boy willing to comply with my every whim is simply bliss. Astrid showed me the list of your sexual services, but said I could do pretty well anything I wanted with you. You seem to be a slut even by this place's standards. She said whipping and humiliating a young slave was amazingly cathartic and she recommended it to any lady in my position."

Jinx had read the literature and looked at the photos on the website but she still could not really believe she had Tim kneeling naked in front of her. She had expected a whore to be loud and coarse; some 'Good Time Charlie' forever laughing and making crude jokes. Tim was the opposite, he appeared shy and reserved, being embarrassed that someone was seeing him naked. She thought of Astrid's advice, "Jinx, we have the most beautiful, best trained and disciplined escorts on the planet. Never since the age of the Caesars have such willing and submissive slaves been available. They'll satisfy your every desire, be creative, enjoy yourself." Jinx wondered how Tim had come to be in the job. Was he really a slave? Bought and sold, providing sexual services for his owner? 

Jinx ordered Tim to stand. She walked around him admiring his pert buttocks, she then took his balls. They felt so perfectly smooth. She had asked Astrid about this, and knew that all the boys had to apply some concentrated Imac type cream on a daily basis. Astrid said it harked back to ancient Greece when all prostitutes had to be shaved.

Jinx told Tim to bend over the table and prepare himself for a caning. Tim bent over tensing his legs and buttocks to present himself to the best advantage. Jinx hit him in the centre of his bottom, hard but not excessively so. Tim squealed. Jinx struck him again slightly above the first stroke. She then followed this with a regular strikes up and down his buttocks. The strokes had a gradually cumulative effect. Tim bit his lips trying to stop himself crying out. Every so often Jinx would strike him particularly hard or in a very sensitive area and Tim squealed with pain. Tim did not know it but this gave Jinx real pleasure and she started aiming for the reddest portion of his now very rosy backside. Jinx then struck him on his thighs, initially this seemed a blessed relief but after a dozen strokes his thighs were agony. As Jinx continued her beating she became more and more aroused. She loved Tim's muffled cries and his tears as they fell on the table.

Jinx knew she could torture Tim all day but had other plans for the boy. She told him to stand and handcuffed him. She caressed the inside of Tim's thighs gently touching him with her forefinger, so lightly there was almost no contact. She felt his balls and penis with the same incredibly light touch, only allowing the tips of her fingers to brush against him. She then started to massage his balls. Tim rapidly became erect. Jinx had always been submissive in the bedroom and had long wanted to reverse her role, she had long fantasised about raping a boy. Now she had a chance. She wasn't sure if you could rape a slave but she wasn't worried. Jinx pushed Tim back until he fell onto the bed. She knelt over him and manoeuvred his penis into her pussy. Jinx slowly lowered herself so as to take the full length of his cock. Tim was now very hard and Jinx was similarly excited. She rose slowly and then plunged down trying to get Tim even deeper inside her. Jinx gradually increased the pace fucking Tim with greater and greater speed and ardour. The poor boy was nothing but an erect penis to her. She rammed her body down on his with a passion that bordered on violence. It was fantastic, wonderful. She shouted with pleasure as she neared climax. She had never cum with anything like this intensity. He was her first fucktoy; this is what men were made for. 

Even after she had cum her pussy was on fire. After what seemed like only a few minutes she was busy getting Tim erect again. She then mounted him and fucked him again. This second time was almost as good. But this time there was to be no quick recover, she was spent. It was a blissfully satisfied Jinx who pulled the satin sheets over Tim and herself and went to sleep almost immediately.

Jinx slept soundly having blissful dreams of taking Tim against his will in ever more extreme situations. Tim's night was less comfortable, as the handcuffs dug into his wrists. They both woke as one of the off-duty whores knocked on the door and served breakfast. Tim recognised her as Olivia, she was wearing a maids outfit with a microscopic skirt, evidently hoping for an early date.

Jinx luxuriated in the huge bed, still terribly turned-on. She picked at the croissants and sipped her coffee, taking pleasure in feeding her captive. After their breakfast Jinx positioned Tim in the middle of the bed and fucked him, again. She knew she would never tire of raping Tim. It was divine. The power, the ability to humiliate the poor boy. He really was her toy. He looked so vulnerable, he was so vulnerable! Jinx could not bear to release Tim and left him handcuffed on the bed as she showered.

After Jinx had finished she freed Tim and told him to shower (with the door open), shave and do his hair. When he finished he knelt before her. Jinx then replaced the handcuffs and put a heavy metal collar around his neck, this was attached to a chain which in turn was bolted to the bed. Jinx said she needed some air and told Tim to kneel until her return. 

Jinx spent a relaxing few hours at the Kusiemski pool and just before lunch returned. This time she dispensed with the formalities and simply pushed Tim onto the bed and raped him again. When Jinx was fully satisfied, she released Tim and told him to dress. She lay on the bed naked as she watched as Tim got dressed in a clean uniform. Tim winced as he put on his knickers and tight shorts, feeling the evidence of Jinx's beating the previous night. Once he was back in uniform Jinx gave him a huge hug and said she looked forward to taking him regularly from now on. 

Jinx watched as Tim left, marvelling at his pert bottom in his satin shorts. She still felt a huge sexual buzz, but she knew the real pleasure was psychological; she had beaten and raped a man. She felt great, her power over Tim had been so liberating. Her husband would have a much tougher fight from now on.

~

Jessica was sunbathing when she got a call summoning her to Miss Christensen's office. She curtseyed as she entered the room and was about to get to her knees when she saw Miss Christensen was talking to two ladies, both pretty, one in her mid-forties the other in late teens or early twenties. The resemblance was striking and Jessica immediately assumed they were mother and daughter. Miss Christensen motioned Jessica to an empty chair.

"Jessica, thank you for coming. I have a little job for you."

The older lady interrupted, "Astrid is one of my oldest friends, we worked together when we were younger and for old times sake she has offered to give me, or really my daughter, Holly, a helping hand. As you see Holly is extremely attractive, the trouble is she is complete idiot, so her career prospects are not all they might be. We have narrowed her future down to either marrying a rich chap who doesn't over value intelligent conversation, being a model or being a whore. She has already done a bit of modelling and things are going quite well; the trouble is that it is a very tough business, so I thought she should find out how she likes escorting. I loved it, but everyone is different."

"So Jessica can you look after Holly for the next day or so. I will organise your dates and don't worry I will ensure you are alright financially."

Jessica consented, "Of course, I would be more than happy to show Holly the ropes."

The Holly's mother turned to her daughter, "You have a day under Jessica's wing as 'work experience'. Your clients will be real punters so obey everything Jessica tells you. But have fun, I will see you for lunch tomorrow."

Holly followed Jessica from the room. "Your mother seemed a bit harsh."

"Oh she is only being realistic. There is no way I could spend my life behind a desk. As she says I am none too bright and have the concentration span of a goldfish with a low IQ. It genuinely is modelling or whoring. Listening to their conversation I am pretty sure Astrid and my mother met when they were both 'on the game'."

"OK, as long as you are doing this of your own free will. First, we had better get you kitted out."

Jessica took Holly to the 'Wardrobe' suite. "Right go and choose yourself some kit. You will need underwear, a white shirt and a black skirt like I am wearing. Remember we are meant to be 'schoolgirls'. When you have found things that fit, change and come and see me." 

Jessica was sure Holly was ignorant over many things but suspected she knew her way around a clothes store. She picked out a grade six's tie and gossiped to Mrs Nasi, the Wardrobe manager.

After about half an hour, Holly came back in her uniform. She looked great. Jessica noticed that Holly had chosen the very shortest of skirts on offer. Daring, but Jessica had to admit it showed off her long legs to a T. The shirt seemed to be the right size i.e. rather too small so Holly's tits looked as if they were straining to get out. Jessica lifted Holly's skirt and saw Holly had gone for some lacy black knickers, suspenders and stockings.

"Holly you look very sexy indeed. You need two skirts, two shirts and half a dozen sets off of lingerie. You should also pick up a couple of pairs of bikini bottoms."

"Six pairs, I am only here for a day."

"Jessica, you are now a 'working girl' and these are your work clothes."

Mrs Nasi folded the clothes and bagged them. Holly was about to pick up the bag when Mrs Nasi gave her a large tub of gel and a two dozen condoms, this time Holly did not ask for an explanation.

Jessica hoped she would have an hour to explain the basics to Holly before Miss Christensen ordered them on their first date. "Now Holly tell be about yourself. First basic question, are you prepared to sleep with a man you find unattractive?"

"Jessica, I may be new to this but I am not that naive. I came here to work as a prostitute, of course I can deal with that."

"Good, have you any experience of anal or lesbian sex."

"I have messed around with girls in the dormitory but nothing serious. I have never done anal, but I am keen to try. In fact I am rather looking forward to it."

"OK, what about pain, have you ever been whipped?"

"No, mum warned me that S&M was this place's selling point and the reason you are paid so much. I am happy to try, but can we have a code word if the pain gets too much?"

"Holly, I want you to do a lot more than try, but yes we can have a 'safe word'. I'll ensure no one hurts you too badly."

"The most important thing to remember when whoring is that you are trying to give your client a good time, that means being enthusiastic no matter how tired or sore you are. It also means lots of kissing, realistic moans of pleasure and passionate sex. Let's start with some practical advice."

Jessica stripped off and told Holly to do the same. She started the demonstration with an explanation of how to put a condom on a client then went on to how to 'lube up', how to give a blow job, kissing techniques and how to prepare yourself if the client wants virginal or anal sex. She then explained the basics of S&M and how a client could hurt and humiliate her.

Holly was visibly shocked at some of the advice, but to give her her due she didn't try to pull out or say she would refuse to do anything. Jessica was sure she had dispelled some of Holly's romantic notions but was at pains to say how much fun it could be as well. She explained that there were days and clients where she returned to her room on 'cloud 9' amazed that she could be so highly paid for having so much fun.




Tim Ch. 02



Jessica was enjoying this. She forgot how much knowledge about whoring she had accumulated since coming to the island and Holly seemed a very willing pupil. Eventually the inevitable call came from Miss Christensen. They were told to put their uniforms on and go to suite 652, they were to attend 'Seb Prasca'.

When Seb answered the door, the girls curtseyed and asked if he wanted some company. They looked almost painfully attractive and Seb was grateful that he didn't have to go out and try to pick up such a girl. He knew they were there for his pleasure but he still somehow felt shy about approaching a prostitute.

Seb had made a mint in the internet boom and unlike many of his peers had managed to get out before the dotcom crash. He was innocent of the real world and fantastically wealthy. He had been recommended Cartwright & Palmer by one of his partners who had been impressed that although the prices were high neither the girls or the management had tried to rip him off.

Jessica led Holly to the centre of Seb's huge suite. She loosened Holly's tie, she then began to unbutton her shirt. Holly was quick on the uptake and started to reciprocate. They stood in the middle of the room and shed their shirts, then bras. Jessica reached around and unzipped Holly's skirt. As she lent over she kissed Holly, tentatively at first then as Holly responded with ever greater passion. When they had struggled out of their skirts and stockings and were left in their panties, they knelt before Seb.

"Can we go sunbathing together, Master?"

Seb thought this was a great idea, but was still too shy to change in front of them. He briefly left the room and returned in some shorts. Seb lay on the central longer. As it had been designed for two, Jessica and Holly found it easy to curl up on either side of him.

Jessica leaned over and smiled at Seb, as they chatted she began play with his nipples. Holly started to massage Seb's inner thighs, she snuggled up close and let Seb feel the heat of her pussy.

"Seb, it's hot. Would you like something to drink?"

"Yeah, can I have a beer please? There are some in the fridge by the bed." Jessica got up leaving Holly entertain their client. 

When she returned with three beers, she put them down on the table and said, "Seb, is it OK if I strip off. I hate tan lines." As Seb did not immediately object she quickly stepped out of her panties and lay down beside him. Holly immediately got up and teased Seb as she slowly removed her panties.

"Jessica, you know I have sensitive skin, can you help me with some sun tan lotion." Jessica got up and crouched over Holly's calves and massaged the cream into Holly's back. Holly turned over and Jessica did her front. She started with Holly's lower legs, moving upwards, being a friend she took a long time to ensure that there was ample cream rubbed in the sensitive area between Holly's legs. She then moved on doing Holly's tits, then neck and shoulders. As she did this her tits rubbed against Holly's. Holly looked serene as Jessica worked, but as Jessica moved upwards she opened her mouth and was rewarded when Jessica gave her a romantic kiss. Seb watched amazed at the performance. When Jessica had finished Holly returned the favour. 

The girls returned to Seb's side and Jessica continued to play with his nipples. Holly started rubbing his thigh, but gradually her hands eased upwards to begin with massaging the area each side of his penis but when she got no resistance went on to the penis itself. Her touch was light and she was massaging through the material but Seb quickly became erect, as her massage continued he became painfully erect straining at the shorts' material. As Holly continued, Jessica leant over and started to kiss Seb.

Nothing was said but Jessica and Holly started to ease Seb's shorts down his thighs until her was completely exposed. When he was naked Jessica rolled him over and then began to massage the sun cream into his back. Jessica leant so close that Seb felt her tits rubbing the cream into his back. Holly concentrated on his legs or rather his buttocks and the area between them. At Jessica's signal they rolled Seb over and massaged cream into his front. 

Seb had never felt bliss like this before, this was no quick professional service he had received from other whores. He felt desire from every pore of his body, Jessica and Holly were so gentle but it was so erotic. He had a huge erection. Holly knew her duty and straddled him and eased his prick into her pussy. She slowly rose, then fell, once, twice then with increasing the pace. Jessica eased away as Holly got into her rhythm. Seb reacted reaching for Holly's tits. Holly clasped Seb's cock in her pussy and rode him without mercy. He did not last long but Seb felt it was one of the finest orgasms he had ever experienced. Jessica and Holly both snuggled up to him and they dozed in perfect contentment. They woke in time for lunch that they took in Seb's suite. The girls remained naked throughout as they ate their salads, Seb struggled into his shorts.

After their coffee, Jessica took Seb's hand and led him to the bedroom. She lay down on the bed, spread her legs and beckoned Seb over. Jessica guided him to another passionate climax. Seb thought she was a genius, so tender, so sensual and the body of goddess. He had never been so tired or so absolutely sexually satisfied in his life. He was beyond bliss. It was with huge reluctance that he allowed Holly and Jessica to put on their schoolgirl uniforms and leave. They were all content, Holly was pleased with her performance and Jessica was proud of her charge. The girl was a natural, but was disciplined and had faithfully followed all Jessica's instructions.

Jessica and Holly's second date was with a young and by reputation hugely successful trader called Greg. Greg went for the preppy look but Miss Christensen had warned Jessica he liked to punish his girls. This would be Holly's first big test. Greg ushered them into a school room where he told them to bend-over one of the desks, drop their knickers and raise their skirts. They did as they were told, Jessica thought Holly looked fantastic with her long legs perfectly straight, bending over pushing out her luscious bottom. Greg agreed as he caned them hard. He started with Jessica, his strokes were hard rather than erotic. Jessica knew he enjoyed hurting girls rather than merely play-acting. She bit her lips trying to avoiding screaming, but this only seemed to encourage Greg who struck her harder and harder until she cried out in pain. She cried and pleaded as he whacked her again and again. Eventually Greg seemed satisfied. He then went to work on Holly's virgin bottom. Jessica was hugely impressed that Holly also tried to restrain her cries. But Greg showed no mercy, he beat her until her bottom glowed. Holly quietly sobbed, but made no attempt to move or protect her bare bottom. She took her punishment like a professional.

"Good, my little ones. Jessica kneel. Holly spread your legs."

Holly felt Greg's hands on her now very sensitive bottom. God it hurt. She then felt his penis inch between her buttocks. Holly knew she was about to lose her anal virginity. She tried to relax as Jessica has trained her. Greg eased himself in. He then started to thrust, gently at first but with increasing vigour until he was close to climax when he was pounding away with all his might. Jessica saw Holly was in huge pain, but still tried to cry out in 'ecstasy' telling Greg how much she was enjoying it. Eventually Greg came.

As soon as Jessica saw this, she approached and led Greg over to the bed and started to suck his now soft penis. She hoped this would give Holly time to recover from her first anal experience. Jessica was now quite expert at blowing men and could resuscitate even the most spent member. Greg was no exception and she quickly got him erect again. As she looked up she was surprised to see Holly now just dressed in her stockings and suspenders coming over. She looked sensational, she leaned over Greg and started to nibble his ears and then to kiss him. Jessica had never seen anyone give such an erotic kiss. Holly seemed to putting her heart into it straining to get her tongue as far down Greg's throat as possible. Tenderly embracing him. Jessica now redoubled her efforts and was quickly rewarded as Greg ejaculated again. This time the poor boy was truly exhausted. Holly and Jessica dressed in their uniforms, curtseyed and left. It was only now that Holly complained at how much her whipping and fucking had hurt.

With Miss Christensen's permission Jessica allowed Holly to go on her first solo date the next morning. Jessica watched her performance via CCTV ready to step in if there was a problem, but Holly handled things well and she had her first client of her own. When their time was up, Holly thanked Jessica profusely for her guidance. She said she would still like to have a go at being a model but was confident if this didn't work out she would be very happy applying for a job on the island. Even if the modelling went well Holly said she might ask Miss Christensen if she could work on a part time basis.

The first guests started to leave the island on Sunday afternoon. Whores were expected to go down to the marina, in uniform, to wave goodbye. Tim knew Christin was leaving on the 4pm shuttle so was keen to see her one last time. He eventually caught her eye and knelt as she approached. Christin gave ruffled Tim's hair and ordering him to stand gave him an affectionate hug, whispering that she hoped to be back soon to continue his education. 

Personal goodbyes finished, Tim joined the rest of the whores. Everyone was smiling and waving, it was a happy scene. They really had recruited some very beautiful boys and girls. He looked around, struck by how flattering the uniforms were. He saw Claudia enthusiastically waving to an ex-client. As she did, her satin skirt rose up, revealing her bottom. This was criss-crossed with vivid red lines, the poor girl had clearly taken a harsh beating, but one would never guess this from her happy demeanour. 

The weekend had been a lot of fun, tough at times, but Tim enjoyed playing the school boy. He just wished he could wear his uniform more frequently. He loved the feel of the satin, and knew the tight shorts showed his legs off to the great advantage. He would look forward to the next school party.



Tim Ch. 03



This chapter works as a stand-alone story. It is filed under "Transsexuals & Crossdressers" as Tim is forced, against his will, to dress as a girl, but it contains BDSM scenes. Some readers of the series may wish to go directly to "Tim Ch. 4 - The Finale, Tim is beaten and humiliated as never before." 

*

Miss Christensen leaned over her CCTV monitor, watching Tim as he walked naked across his room, drying his hair, "So, Janey what do you think?"

"Well he's a very handsome guy."

"I know, even the severely visually challenged could tell me that. But a client wants him for a TV date, with makeup and training can you get him to pass the nineteen-twenty test?" She was referring to her rule whereby she would only allow her whores to do transvestite dates if nineteen out of twenty people would take them for girls.

They watched as Tim pulled up the satin shorts of his skimpy sailor's outfit, "Difficult to say without seeing him in the flesh, but he looks promising. Lithe body and androgynous face is pretty ideal. Can you allocate him one of the rooms with a two way mirror so I can study him in more detail? If so, I'll give you an answer by tomorrow close of play?"

Miss Christensen looked at Tim's on-screen diary, "OK, he has a Dungeon date with Mrs D'Lisle at 11.30 tomorrow. I will put them in room 136."

"Thank you." Jane D'Alquen was excited. Tim looked great and she thought she could turn him into an ideal girl, but Miss Christensen's '19/20' test was demanding and she would not agree to try unless she was absolutely sure she could pull it off.

Two days later, Miss Christensen summoned Tim to her office. He entered with some trepidation, worried that a client had made a complaint or that his feedback scores were deteriorating. Tim immediately knelt, but Miss Christensen waved him to a chair.

"Tim, a client has requested you for a TV session. I have watched your progress over the last couple of months and I am confident you can do it. This is a real vote of confidence in your ability and something you should be proud of. If things go well this could result in some very lucrative dates."

Tim had been 'soft soaped' before and Miss Christensen was good. Her tone was sincere and face sympathetic, but 'proud' was not what he was feeling. He had come to terms with being forced to work as a prostitute but dressing up as a girl was one stage too far. So he appealed, "Mistress, I am not sure I am comfortable with this. Isn't there anyone more suitable? I thought we had Jamie who did this sort of thing."

"Tim, the client specifically asked for you, anyway Jamie is on a three month loan at the moment. Don't worry, I am sure you will enjoy the experience."

Tim knew he had no real choice, he could plead or get angry, it wouldn't change anything. He would still have to do whatever the client wanted and would just irritate Miss Christensen and potentially delay his promotion to 'Grade three'. A great General never fights a battle he knows he is inevitably going to lose, so Tim meekly accepted his fate. He was therefore sent down the hall to see Miss Veiss.

"Tim, we have a month to prepare you. The first thing to do is to get you to practice walking in stilettos." She gave him a pair, "You will practice for an hour every day, whenever you don't have a date. You will soon get the hang of them. The second thing is your voice. We are going to have to work on that. I have booked you in for an hour's elocution, initially every day. Don't worry I am not going to try to get you to talk in some high soprano. We will work on some subtle changes to your normal voice and you will be amazed at the net effect." With that Tim was dismissed with instructions to present himself at Miss Veiss's office at 5pm the next day.

Dutiful as ever, Tim tried on the stilettos immediately he got back to his room. They felt very strange. His first attempts to walk in them, made him feel like Douglas Bader. In the first half hour he must have fallen over twenty times. But after a week of practice, Tim got the hang of walking in high heels and even looked quite elegant in them. Miss Veiss did wonders with his voice. It was still the same pitch as before but now had a soft sexy purr to it, it was unmistakably feminine. 

At the start of the first lesson she made Tim strip and put on a bright pink basque and matching panties. She said he must feel totally natural wearing all kinds of risqué female lingerie. She explained how he would start his TV date by massaging his client's ego. He had to remember than many clients would be excited, but at the same time nervous, about sleeping with a transvestite. He should quickly establish physical contact, snuggling up to his client and encouraging them to feel his lithe body. As they became comfortable in each other's company, he should then discreetly slip his hand between the guy's legs and gently stroke him, so that by the time Tim took him to the bedroom a client would be desperate for sex. 

There, Miss Veiss explained how Tim should strip down to his panties, and help his client out of his clothes. She then demonstrated how a girl gives a blowjob and the energy he must put into it. Once a client was excited she showed Tim how to manoeuvre the guy's cock into his arse. She favoured getting the client to fuck him in the doggy position. Despite the pain and humiliation, he must be sure to squeal with pleasure, encouraging his client to ever greater exertions. She stressed that after Tim had brought a client to climax, he should immediately start planning how to bring him to a second. Even then, he must always be ready to perform extra sexual services no matter how tired or sore he may be. 

Although most clients would only really be interested in Tim's performance in the bedroom, Miss Veiss also taught him how a high class escort should act in public. On the first day, she showed him how to dress, the kind of jewellery he should wear and what handbag he should carry. Tim was then given lessons in feminine posture and deportment and had to practice moving with languid grace. Later Miss Veiss took time to teach him how to reapply his makeup, walk, sit down and get up in a ladylike fashion. She stressed he must appear demure and as he would inevitably be wearing an extremely short skirt he must be sure to keep his legs together when seated and be very careful when getting in and out of cars. In short, he had to come across as a beautiful, sophisticated young lady, with just a hint of naughtiness.

Although Tim did as he was told, he was tortured about the thought of dressing as a girl. He may have been forced to work as a submissive prostitute, but at least he was a male prostitute. He felt Miss Christensen's plan to sell him as a TV undermined his masculinity. But the problem was, he knew the punishment he would receive if he refused to go through with the date. So he swallowed his pride and continued his training.

With only a couple of hours left before his date Tim was directed to Miss D'Alquen. She was a middle aged lady, who had a goodish figure and short black hair. She was dressed in a makeup artist's white polyester dress.

"Tim, welcome. We have some work to do. Have you shaved?"

"Yes, ma'am."

"Right show me."

Tim stripped and stood naked before Miss D'Alquen and let her examine him. "OK, well done. Let's start with the easy bits. Lube yourself up and put on these stockings and suspenders." 

Tim sat on the edge of the bed and spread his legs and massaged a good amount of lubricant up his arse. He then put on the black suspenders. The stockings slipped up his smooth legs and he secured them without difficulty. Miss D'Alquen then handed him some panties which he started to put on. She was standing close to him and he felt her cold hands as she pressed his penis between his legs, before telling him to pull the panties up fully. The panties were very tight, so that his cock would stay 'in place'. He was left with some protrusion but it was barely noticeable. The other thing about the panties was they had a hole in the rear, so he could be 'taken' without removing them.

When Tim was done, he perched on the edge of the bed, unconsciously trying to hide his nakedness. Miss D'Alquen gave him a black choker, as with the underwear, edged in pink lace. She explained this was to hide his Adam's apple. She then handed him a matching black satin corset and told him to put it on. Tim noticed some subtle padding over his chest to give the impression of undeveloped breasts. When he had put it on he stood in front of Miss D'Alquen so she could see.

"Tim, what are you doing? You clearly have never done this before. Lie on the bed." Tim did as he was told. Miss D'Alquen then slipped off her shoes and straddled his chest and started vigorously tightening the corset. Tim felt as if his insides were being put in a vice. When Miss D'Alquen had finished Tim looked down, he had never been fat but his waist was now tiny. He just wondered if he would be able to walk or for that matter breathe. Eventually he managed to stand up and was pleased the pain seemed to fall away quite quickly, it was still pretty uncomfortable but no longer acutely painful.

"Tim, don't whinge. Your body will quickly get used to the corset. If a million Victorian women could put up with them, you can for a few hours. We need you to wear it to give you something of a figure. Now sit on this stool, I have some work to do."

Tim sat on the stool facing Miss D'Alquen as she started his makeup. The first choice to make was, if to use a wig or not. She always tried to avoid one if she could and with Tim it was a relatively easy decision. She brushed Tim's hair back and secured it with some hair clips and then attached some clip-in pony tails tied with some discreet pink bows. She took great trouble to match the colour of the hair extensions so they merged perfectly into Tim's real hair. She then chose some earrings, it always surprised her how much these changed a boy's appearance. The hard work was his face, this was where she earned her money. She was at it for almost an hour. Tim was bored to distraction. Miss D'Alquen scolded him for even the smallest movements. She was very subtle with the makeup, using the absolute minimum possible. The only exception to the minimalist approach being Tim's nails and lips where she used a bright glossy red. 

Eventually she was happy (her only slight worry being that people might think he was under eighteen) and said, "Tim, what do you think? Even if I say it myself I am rather proud of how things have turned out. I am not sure one person in a hundred, probably not one in a thousand would recognise you as a boy." 

Tim looked in the mirror. He was amazed, he knew his face well, very well, but somehow this woman had changed it he would barely have recognised himself. He saw the face of a young girl and although he knew it was himself, his brain found this hard to comprehend. It was a masterpiece.

Miss D'Alquen then gave Tim a satin French Maid's dress and apron and told him to put it on. It fitted perfectly, which was hardly surprising as it had been tailored to his exact measurements. It was inevitably terribly short, just covering his bottom. It had short sleeves and reached all the way up to his neck. Although the corset gave him some curves, he obviously didn't have much of a bust, but then many younger girls didn't.

"You look great Tim. You are one of my greatest creations. You were made for this sort of work. Go to Miss Christensen's office I know she is anxious to see how things have gone. She will tell you about your date. Have fun."

Tim thanked Miss D'Alquen. He was not happy with the process but he had to admit she was an artist. If he had to do this, it was better to look good. In fact he was rather proud of the lustful looks he got from clients as he walked to Miss Christensen's office. This added to the slight swagger he already had. He ensured his bum swayed as he walked as Miss Veiss had taught him.

Miss Christensen welcomed Tim with unusual kindness. She admired his appearance and, after getting him to walk around her office, decided he was ready for his first client.

"Tim, you will be known as 'Lucy' when you are doing TV dates. You will be expected to do all your normal sexual services, but act as a girl. OK, off you go and don't disappoint me."

Tim knocked on the door of Suite 652. It was answered by a guy in his mid twenties, slightly overweight, dressed informally in jeans and a checked shirt. He was clearly expecting Tim as he merely opened the door and motioned that Tim should enter and sit at one of the chairs arranged around a dining table in the suite.

Tim did as he was told, perching on the chair, keeping himself perfectly erect; half because of Miss Veiss's instruction on posture, half because this reduced the pain of the corset.

"So, Tim we meet again."

Tim assumed the guy must be an old client so like a pro he said, "Yes of course Master. It is good to see you. I had a lot of fun last time."

"Tim, you don't recognise me, do you?"

Tim was slightly surprised that the client had not fallen for his gambit, but he had to admit he had no memory of the guy. He was normally pretty good with faces and anyway the System should have warned him if the guy was an ex-client. But he had been caught and there was nothing for it but to admit it, he couldn't remember the man's name.

"I am Ben Freeman. We were at school together."

Tim immediately remembered Freeman, he thought he was a little shit at school and in his experience people did not change. The problem was if Freeman could bully him aged eighteen, he could make his life a misery now. Tim's real concern was what Freeman might say when he got back to Britain, meeting an old school friend who had become a transvestite prostitute was a pretty good after dinner story.

Tim took a deep breath, or as deep as the corset would allow, and said, "Yes, Master, I remember you now. You were a prefect in my first year."

"Yes Tim. Even after all these years I recognised you immediately when I was looking over the web site. Your pictures don't leave much to the imagination. Anyway I wanted a TV and you seemed to be the perfect candidate. Astrid said this was your first time so I hope doing things with someone you know will make it easier."

Tim smiled and said, "Yes, Master, it will make thing a lot easier. I am very much looking forward to this evening." The lie was pretty blatant, frankly there was no one Tim would less like to serve, but he knew there was no getting out of this and flattery was pretty painless. He wondered if Freeman had chosen him so as he could tell the story, because he fancied him or because he wanted to humiliate him. Tim knew he would find out soon enough.

"Tim, a party of us has come to the island. This is our first night and, as I am the only one who has been here before, I am hosting a drinks party. You will serve. I have not told anyone your true identity. They will simply know you as 'Lucy' and you should play the girl for the entire night. You will recognise some of the guests from school, most of them from my year. They will know you are a prostitute so you had better expect a fair amount of sex, but I assume you are used to that." Tim nodded.

"OK stand up. Let me see what I am buying. Lift your dress." Tim did so, showing his tight little panties, "and back. Now bend over the table."

Tim bent over and almost instinctively spread his legs. Freeman gazed at the slit in his panties. The boy was clearly a whore and seemed as obedient as Astrid had promised. Freeman wanted him badly, but knew he would have to wait until after the party, "I am going to change and freshen up. People should be arriving in about half an hour. Get the drinks sorted and be waiting at the door with a tray."

Freeman went off to the bedroom and left Tim feeling shell-shocked. It was always a whore's worst nightmare to be recognised by someone they knew. What had the guy got in mind? He just couldn't read him. Tim knew there wasn't much point in worrying as it wasn't going to change anything. If Freeman wanted to disclose Tim's identity he would and the probability of all these people keeping their mouths shut was minimal. Oh God, every time he thought his life was at a nadir he found things could in fact get worse.

Tim stood up, automatically straightened his dress and went over to the drinks. He poured the champagne (a decent vintage he noticed) and rather unprofessionally had a glass himself. He felt entitled to a little Dutch courage.

There was a knock at the door and Freeman came out dressed in a dinner jacket, "Ready Lucy?"

"Yes, Master." Tim got the tray of glasses of Champagne and followed Freeman to the door.

Freeman welcomed a man of similar age, "Freddie." Tim remembered him as Frederick Croft, a sporting hero when he was eighteen, but looking at his waistline no longer such. Tim curtseyed as Croft took a glass of champagne.

There was a short wait until the second guest Thomas Kipling, or "Kippers" as he was known at school, arrived. More hugs and another effusive welcome. After that the guests came thick and fast. Tim thought he recognised about half of them, mostly male but there were a few women, all glamorously dressed. Tim had to admire them, there were not many women who would agree to accompany their boyfriends or husbands to a brothel, they must have some character.

Initially Tim was certain one of the guests would recognise him at any minute, but they didn't seem to and after a while Tim was run off his feet serving the drinks so he forgot about the prospect of imminent exposure. After the guests had drained their first glass and obtained a refill, things slowed down and Tim could circulate in a more relaxed fashion.

After about half an hour one of the guests (Douglas Berneville-Claye no less), clicked his fingers and motioned Tim to come over.

"Lucy, Ben tells me, you have skills other than merely getting drinks. In particular he says you give a great blowjob. On your knees girl and show me what you can do."

Tim looked around, clearly Berneville-Claye meant he wanted a blowjob in front of everyone. The guy had always been a show off. Tim got to his knees. He got his cock in his hands and started to suck. One of the things Tim had learnt on the island was how to give fellatio. He started by softly licking the penis. When he took it in his lips Tim did it so gently he barely allowed it to touch the sides of his mouth. Tim gradually started to suck, harder and harder. He paid attention to the whole penis, not just the head, swirling his tongue around the tip while pumping Berneville-Claye with his fist. He lovingly massaged his balls and deep throated his cock. Tim quickened then slowed down, trying extend the pleasure and to show his enthusiasm. When Berneville-Claye started to cum Tim continued to suck with renewed vigour, so that he exploded down Tim's throat. Tim swallowed all his cum, smiling with 'pleasure'. Finally Tim zipped him up and getting a short round of applause, he curtseyed and said "Thank you, Master that was wonderful."

As Tim moved away another guest called him over. Tim saw Freeman staring and nodded that he should service the man. For once the guy did not seem to be from school, a relief, but his manners were no better for that. "Come on Lucy, you are still thirsty aren't you?"

Tim knelt and said, "Yes, Master." 

Tim took the guy's penis and started to tenderly kiss the end of it, smiling to his client in his most horny way. Tim then took the tip into his mouth sucking and kissing it as if it was the most important thing in his life. Eventually when the guy was terribly hard he started sucking with his normal vigour. Taking it all the way down his throat. Sucking harder and harder with ever increasing urgency. As the man tensed up, he grabbed Tim's hair and yanked his head back. As he did, he ejaculated all over Tim's face. Tim felt the hot spunk hit his eyes and nose. The man gripped Tim hair and masturbated to so Tim was covered in cum. Tim closed his eyes, his first reaction was repulsion, wasn't a public blowjob humiliating enough without this? Tim's second thought was for his makeup, would this spoil Miss D'Alquen handiwork and without his makeup surely he would be recognised, and what a way for one's cover to be blown (no pun intended).




Tim Ch. 03



As Tim rose to his feet, one of the guests, Tim had cum in his eyes so he couldn't see who, grabbed him by the arm. "Come here, you tart. I want to give you a shag. Bend over the table." Tim bent forwards and hoped the guy would be happy with his arse. He was now grateful for opening in the back of his knickers. It seemed Tim's bottom was more than acceptable. The man pulled up Tim's skirt and started to fuck him. Gently at first but with gradually increasing vigour. Tim wiped the cum out of his eyes and quickly recovered starting to move in time with the man's thrusts. After a short while Tim felt an explosion in his arse as the guy came.

Tim was just about to rise when another guest pushed his head back onto the table and started to fuck Tim again. The difference was that the new guy didn't work himself in, his first thrust was with full vigour. Tim was used to being taken, but this was surprise, he squealed with pain. This amused his client and the guy started pumping with ever increasing venom. Tim knew no one could keep this sort of thing up and sure enough Tim's customer came rapidly, his cum soaking Tim's panties.

Tim heard the man boasting of, "Giving the whore a real 'punishment fuck', that she would remember for the rest of her sordid life." This seemed to amuse 'Woody's' audience and he exchanged 'high fives'. Tim quickly pulled down his dress, he knew he could not stand a 'gang bang' and had to leave if only to check his makeup.

Tim quickly slipped through the crowd and found Freeman, he curtseyed and asked if he could go to the 'Powder room' to sort out his makeup. Freeman looked at Tim, cum still dripping down his face, and agreed telling him he should be quick.

It was a very sore Tim who knocked on Miss D'Alquen's door. On entering he immediately took off his soaked knickers and threw them in the corner. Feeling considerably better, he faced Miss D'Alquen. She smiled, "Been having fun?"

"No. How do I look?"

"As I am sure you are aware you are covered in cum. It has rather spoilt my masterpiece but don't worry, you look like a cheap whore but still a cheap female whore. Sit on the stool and I will repair the damage."

Tim sat down, the cool leather soothing his painful bottom. After that fucking, keeping still for Miss D'Alquen seemed a relief rather than a bore. After about twenty minutes she was finished, she then helped Tim clean up his maid's outfit. The satin apron was easy to replace and the rest of the stains could just about be cleaned. When Miss D'Alquen had finished, Tim lubed himself again and put on some fresh knickers. Feeling much better he returned to Freeman's suite. The party was breaking up. In the end he merely stood by the door and collected the guests' glasses as they left. 

~

After Tim had tidied the room and called Room Service to take away the bottles and glasses. He went to Freeman, curtseyed and asked, "Is there anything else I can do for you, Master?"

Freeman looked at Tim. He had originally booked him as a joke. His idea was to get Tim to give blowjobs to his friends, then to get him to slowly strip naked. Revelling in their humiliation when they recognised he was a boy. But now he wanted Tim himself. Woody wouldn't shut up about how good Tim was and that bore Berneville-Claye said it was the best blowjob he had ever had. Looking at Tim, Freeman simply could not believe that he was a boy. He thought back to school, he must have seen Tim naked dozens of times when supervising the junior boys' showers. He even remembered having Tim stand naked waiting for the Duty Master after catching him fighting in the changing room, there was no doubt he was male.

As Freeman thought, he heard Sally, his girl friend, enter the room. He turned and saw she was wearing French Maid's costume. Freeman had to admit she looked great. She had chosen a lower cut uniform than Tim, so it showed off her tits to best advantage. 

"Tim was getting so much attention I thought I ought to copy him. What do you think?" Freeman was speechless.

"Come on Ben, can I have him? You can watch if you want."

Freeman agreed, he knew he could not very well refuse, if he was going to have Tim himself later in the weekend. 

Sally led Tim over to the bed. Conscious that Freeman was watching Sally slowly undid Tim's dress. Tim stepped out of his uniform and eased Sally's dress down her slender body. Kissing they knelt on the bed. She clasped his buttocks and began kissing him with huge urgency. Tim took his cue and responded in kind. Sally was lovely and he was now very turned on. As they fell onto the bed, he started to pull her knickers down her long legs. Sally was not so gentle she yanked down his pantries and grabbed his cock, "Come on Tim, show me what this was really meant for." Sally started sucking Tim's cock, he was soon very hard. Tim pulled Sally's hair and forced his penis further and further down her throat. She seemed to swallow it with ease. When he felt he could not hold on any more, he lifted Sally off his cock and placed her on the bed spreading her legs as far as he could. Wow she looked obscene, her pussy glistening, just waiting for him. She didn't have long to wait, Tim straddled her and had no difficulty entering her very wet pussy. He thrust in and heard her shout of pleasure. At this pitch of sexual excitement they couldn't last long. Tim thrust with ever greater urgency, whilst Sally dug her nails into his back, leaving long vivid scars as evidence of her pleasure. Sally came first with a shout of triumph. Tim followed soon after. Tim leant back; that had been fantastic, absolute bliss.

Freeman lounged back and watched them. He found it hugely erotic, he was curious he felt no insecurity as his girlfriend enjoyed another man. He knew he could click his fingers at any point and have Tim on his knees in front of him, he knew the whore was no threat.

Tim lay exhausted on the bed. Sally had other ideas, "Tim, no slacking. Up you get you have more work to do."

"Ben, Tim and I want to thank you for that little frolic." She started to undress Freeman indicating Tim should help her. When he was naked Sally blindfolded him and led him to their bed, whispering in his ear, "When we come back we are really going to take you to heaven." Freeman could not believe what he was hearing, Sally had never been this adventurous in the past. But there was no doubt watching them had been hugely erotic and his erection was now painful it was so extreme. So why not see what Sally had in mind? Perhaps Berneville-Claye was right about Tim's sexual prowess.

Freeman couldn't resist a peak as Sally and Tim entered the room. He couldn't see much through the blindfold but saw they were both back wearing their maids' outfits and carrying something heavy. Sally quickly dimmed the lights so Freeman could no longer make out one from the other. She then reached over and tightened the blindfold, now Freeman could see absolutely nothing. Freeman felt his arms and legs being moved so he was spread-eagled on the bed. Tim and Sally then buckled on some wrist and angle cuffs and clipped these onto the four corners of the bed. Freeman was now absolutely helpless.

Initially there was just silence. Freeman wondered if Sally and Tim were still in the room. Perhaps this was a wind-up. Just as he was getting worried he felt someone starting to lick his nipple. They were doing this so gently, their tongue was barely touching his chest. It was infinitely erotic. Gradually they got closer and they started to lick more vigorously, then they started to nibble. Freeman wondered who it was. Then he smelt Sally's perfume. It must be her. Therefore Tim must be licking his inner thigh. As he realised this, 'Tim' took his penis in his mouth and started sucking. 'Tim' knew his business as he was simultaneously masturbating him. Freeman's mind was confused, surely he shouldn't like a man giving him a blowjob. However confused his mind was, his body did not share the uncertainty, he was very erect. Just as Freeman thought he could not last any longer, 'Tim' released his cock. 

Freeman felt Sally and Tim change positions and now 'Tim' started to lick his nipples. Freeman was breathing hard, this was divine. He breathed in trying to guess 'Tim's' aftershave. Freeman smelt and realised the person licking his nipples was also wearing Sally's perfume. The subtle tart she must have sprayed Tim with her scent. So now Freeman had no idea which of them was licking his inner thigh and which his nipples. They were both doing it so gently and they both had supremely soft hands. This second blowjob was driving him crazy. Just as Freeman thought he couldn't resist any longer, the person stopped.

One of them climbed on the bed and sat on his thighs and started to play with his cock. The other sat on his chest. Freeman could now feel Tim's balls and knew he must be on his chest. Sally sat up and directed his cock into her pussy and started riding him with a slow constant rhythm. Tim moved closer. Freeman felt Tim's cock rub against his mouth.

"Come on Ben, you know you want it. You were always watching me at school when I was unavailable. Now I can be yours. Take my cock. Suck it." Tim pushed a little harder.

Sally who was beginning to fuck Freeman with increasing speed, said, "Go on Ben, have some fun. Tim has a divine dick, he tastes great."

Freeman was gradually being overwhelmed by the eroticism of the moment. He opened his mouth and started sucking. Tim felt Freeman's mouth close on his cock. It felt good, Freeman was clearly an amateur at giving fellatio but he was hot and wet. The harder Freeman sucked the harder Sally fucked him. Sally was screaming with pleasure. Freeman came first, closely followed by Sally. Tim hearing their cries of ecstasy then came himself. Freeman tried to close his mouth but Tim, wouldn't let him. He was determined to deposit his entire load in Freeman's throat. If he was going to give a man a blowjob he should do it properly. Tim held Freeman's mouth and forced him to swallow. Not really how one should treat a client but Tim was excited and he was sure it was for Freeman's own good.

Thoroughly sated, Sally and Tim both curled up either side of Freeman and went to sleep. About an hour latter, Sally woke up, gave Tim a shake and released Freeman from his bonds. Tim made himself look almost decent and left. Sally giving him instructions that he should return to serve them breakfast at ten the next morning.

~

Tim returned the next morning dressed as a boy in some satin shorts and a T shirt. He took the breakfast in and started setting the table on the balcony. Even though he had been on the island for months, he was still awe struck by the view, the Mediterranean looked wonderful. The sun was warm, but had yet to reach its full intensity, these were Tim's favourite times.

He heard Sally go to the bathroom. Freeman then entered the room. Tim stood up straight and said, "Good morning, Master. Can I serve breakfast?"

"Morning Tim. Get in the position."

This surprised Tim, but he quickly stripped naked and fell on his knees.

"Kiss my feet." Tim did as he was told.

Freeman had never been a subtle negotiator, but he felt that having your opposite number naked at your feet did give him a decided advantage. "Tim, I had a lot of fun last night, but I need your assurance that what passed between us remains strictly confidential."

"I promise not to tell a sole, Master."

Freeman looked carefully at Tim trying to determine if he was sincere. One just never knew, but he felt he could trust the guy. Anyway Tim had probably more to lose if the full story came out. Somehow he couldn't see Tim welcoming a post on the old school website under 'What are they doing now?' that he was working as a transvestite prostitute. 

"OK Tim, I believe you. Now stand up and bend over the table."

Tim had not used any lubricant up his bum, he had simply not believed that Freeman would want sex before breakfast. But clearly he was wrong. Tim prepared himself, he spread his legs and tried to relax, he knew things were going to be painful, but to a certain extent it was his own fault. He would remember next time, always assume a client wants sex whatever time of day it is.

There was pain as Tim had predicted, only it was not due to Freeman's penis it was due to his riding crop. Freeman whipped Tim six times in quick succession then said, "Tim, you are a fucking whore. You do not force a client to drink your cum. If I ever have disobedience like that again from you, I will take great pleasure in torturing you for hours. So remember, show your superiors some damned respect."

The whipping has stung, but Tim stifled his cries and merely said, "Yes Master. I am sorry. It will never happen again." Freeman thought vivid lines made by his riding crop on Tim's pert arse were quite beautiful.

Freeman took a couple of moments to collect himself and said Tim should stand up. He looked at Tim standing naked in front of him, it reminded him of school. Tim was very handsome as a boy or girl. Freeman desperately wanted to take him, this was the ultimate act of submission, and he was determined to get an hour with him before they went on the outing. This said, he knew his desire for Tim was much more than sex. He wanted to dominate and humiliate him. The dressing him up was only the first stage, he would think of many other ways to show his power.

Sally entered the room, drying her hair. She saw Tim's back or rather his bottom with the red marks made by the riding crop. "Morning Tim, Ben what have you being doing to the poor boy?"

"Teaching him some respect." Freeman then nodded and said Tim could get dressed and pour his coffee. As soon as Tim left, Freeman booked him for a date just before lunch. 

This time Miss D'Alquen knew Freeman only wanted Tim for sex, so she dressed him in a black satin basque, stockings and some tiny black knickers. As before, she took huge trouble with his makeup. She decked him out with a few pieces of jewellery and gave him a clutch bag. She was truly proud of her creation, this time she didn't think even one person in a thousand would guess he was really a boy. He looked like a tart but a very expensive one. Tim was dreading the next hour, he hated the thought of Freeman's caresses and whatever degrading acts he would be forced to perform. But he had no choice, he knew he had to submit.

Tim took a deep breath and knocked on the door. Seeing Freeman he curtseyed, "Master, thank you for seeing me. I have been looking forward to this." He slipped his hand between Freeman's legs, and purred, "Let's have some fun, Master. You will find I will do anything for my favourite clients."

Freeman replied, "I would love to get to know your body intimately but that will have to wait until tomorrow. I haven't much time, but I just couldn't leave this place without giving you a good hard fucking. So my little slut, drop your knickers and bend over that table."

Tim did as he was told, lowering his panties and spreading his legs to allow Freeman the easiest of access. Freeman stared at Tim's pert bottom, the evidence of that morning's beating still very visible. He felt incredible desire, he had wanted to screw the boy since school. Even better, he could feel Tim's utter humiliation. Freeman massaged his wonderfully smooth buttocks and gradually spread them. He rubbed his penis against Tim, this excited him and his quickly became erect. He then inserted first one, two then three fingers into Tim's willing, clean and well lubricated arse. Freeman was now ready, his first thrusts were uncertain, but he gradually little by little entered Tim and started thrusting with ever increasing vigour. He clutched Tim's thighs and he thrust deeper and deeper into his school mate. Tim reacted as he had been taught. Freeman was clearly inexperienced at this, so it was important that his first time with a Cartwright & Palmer boy was memorable. From Freeman's shouts of ecstasy and the obscenities he was pouring into Tim's ear, it was evident that he was enjoying himself. 

Freeman felt elated as he penetrated Tim ever harder, it was not just the physical pleasure but the joy of seeing Tim humiliated and in pain. As he reached his climax Sally entered the room, either Freeman did not notice or did not care. His whole being was concentrated on filling Tim with as much of his cum as he could. He came again and again, he just would not stop. Finally he could not go on any longer and withdrew.

"God, that was great. I have wanted to do that for years. Now don't move, Sally may want you." Tim was also exhausted but stayed where he was, bottom exposed and knickers half way down his legs. 

"Darling, I have just finished with Lucy, do you want him?"

Sally returned to the main room and looked at Tim, "There is nothing I would like more than another round with him, but we have to be down in the lobby in fifteen minutes if we are going to catch the boat. So it had better wait for when we get back tomorrow."

"Lucy. Kneel. I may still want a blowjob. It seems that this is all you are good for, my little slut, 'sucking and fucking'." Tim knelt his knickers fall around his ankles, as Freeman went to change. In the end Freeman did not have time for anything more and Tim was bundled out of the room still trying to pull up his panties.

Freeman's party was out on one of Cartwright & Palmer's yachts and only returned on Sunday for lunch. They were royally entertained by some of the prettiest girls on the island. Freeman had some of the best conventional sex he had ever experienced, but his mind was now thinking about really kinky things he would be doing to Tim. Over Sunday lunch, Freeman had to play the gracious host, but sent Sally to ensure Tim was getting ready for his date.

Tim was coming out of the shower, dressed in a short silk kimono, when Sally entered Miss D'Alquen's room.

"Jane, everything OK? Will he be ready for 2 o'clock?"

"Yes he'll be there."

"Ben said he asked for Tim, or should I say Lucy, to be dressed in a short black latex dress. He wants him made up to look like a cheap tart. Is that OK?"

"No problem, the dress is over there on the hanger."

Sally examined the dress, it was polished to a very high sheen, it looked and felt wonderful. As she looked at it, she wondered how Tim would manage to squeeze in.

"Mistress, can I check the Master will be happy if I wear normal knickers rather than latex?"

"What are you proposing to wear?" Sally examined the brief black satin knickers. She thought they looked fine, or better than that, Ben would love them.

Sally and Jane watched Tim as he put on his knickers, suspenders and stockings and struggled into a satin corset. 

"You wouldn't believe how excited Ben got when he found out that Tim was working here. I am sure he has fancied him since they were at school together. He has been on heat ever since, always discussing things he was going to do to him. He couldn't stop talking about all the sexual services Tim offered. He clearly loves having Tim at his mercy. Tim is so wonderfully submissive, he was just born to be a prostitute. Ben has even had a private detective investigate if any more of his school or uni mates have gone on the game."

When Tim had put on in his underwear, Miss D'Alquen started her artwork. She clutched his chin as she applied some bright red lipstick, thinking the boy would have to get used to doing this himself. Sally had left by the time she finished and it came to squeezing into the dress. Somehow Tim got it on, pulling it down with all his might so it just about covered his bottom. The last thing was to buckle on his slave collar. Miss D'Alquen admired her work, the effect was better each time she did him. Tim was a natural, he was so good. She thought how she would love to take Tim/Lucy out for an evening on the mainland, watch people's reactions and listen to their comments. His movements were so natural, it was as if he had been born to play the part.




Tim Ch. 03



Freeman found the lunch purgatory, all he could think about was Tim. Sally had been right he had wanted to do this for years. Now he had Tim in his power, Freeman was almost dying of lust. Freeman remembered the lines made by his riding crop on Tim's perfect arse and felt a bolt of sexual pleasure. He was really looking forward to the dungeon session. He imagined the joy of making a naked Tim scream and beg for mercy. Eventually Freeman, almost incoherent with desire, made his excuses and left.

As Tim walked to the dungeon, his dress rode up his thighs, exposing his cute arse. It was ludicrously short. When he arrived, he tugged the dress down and knelt in the centre of the room, being careful not to ladder his stockings. Room 145 was much like most of Cartwright & Palmer's dungeons, it was painted black with a well polished black wooden floor. It had a St. Andrew's cross, a whipping horse, stocks, some shackles to allow the slave to be suspended from the ceiling and a wall on which was displayed a huge selection of whips and other torture instruments. There was also a large bed, covered in black satin sheets, this being an 'overnight' date. The place was spotlessly clean and the steel shone brightly but it still reeked of depravity and sex. Tim watched the door, ready to lower his eyes as soon as Freeman entered.

Freeman came in still dressed in his Bermuda shorts, "Hi, Lucy. Ready to serve your Master?"

"Yes, Master."

"Kiss my feet."

Tim got down on all fours and kissed. Freeman watched him, fascinated as Tim's dress eased upwards revealing his knickers and suspenders.

"Lucy, stand up."

Freeman circled around, looking at his possession. To think he could buy Tim for such trivial sums of money. Freeman eased up Tim's dress staring at his cute pert bottom. Freeman went closer clasping Tim by his thighs and pushing his now erect cock against Tim's buttocks, he whispered in Tim's ear, "Oh Lucy, we are going to have such fun. All those things we should have done at school. The day after your eighteenth birthday, I should have had you around my flat dressed in a g-string and ready to serve me. You were born to be a slave. My slave. Now we will make up for lost time, you are going to submit to all my desires aren't you Lucy?"

"Yes, Master."

Freeman got Tim to stand below a chain attached to a pulley and some wrist cuffs. He buckled the cuffs onto Tim's wrists and then tightened the chain. Gradually Tim's hands rose, eventually he was standing on tip toes. This meant Tim's dress rode up his body revealing his knickers. Freeman approached, feeling Tim's arse, staring at his suspenders held tight to his bottom. He felt for the hole in the back of Tim's panties and played with Tim's arse. Tim was well lubricated, and he had relaxed his sphincter to allow Freeman easy access, his submission was total. The hole was so inviting and Tim's bottom so beautiful that Freeman could not resist picking up an electric probe, easing it into Tim's rectum and giving him an electric shock. Freeman found Tim's squeal of pain so sweet that he continued to probe Tim, forcing the tip as far up him arse as he could, delighting in Tim's pain. 

Then Freeman went around to the front and massaged Tim's panties. These were remarkably flat as they were small, tight and very well cut. Freeman could feel Tim getting hard and stretching the satin. He knew if he kept up the pressure eventually Tim's cock would break free, but Freeman wanted to excite Tim enough to cause him humiliation and pain but not relief.

Eventually Freeman stopped this game, giving Tim a very temporary respite. He then went and chose a riding crop. He whipped Tim's arse, it was lovely to watch the whip hit Tim's satin covered bottom. Tim gave an involuntary squeal of pain, but Freeman noticed he did not tell him to stop. He whipped Tim's arse then his thighs. He watched as Tim danced to try and avoid the blows. Somehow Tim still looked elegant as he balanced on his stilettos. Freeman felt Tim's arse, it was deliciously warm.

Freeman then pulled down the top of Tim's dress, exposing his nipples. "Your tits are not big enough, girl."

"Sorry, Master."

Freeman squeezed Tim's left nipple, vigorously pulling it back and forth. Tim squealed with pain. Seconds later Freeman was repeating the treatment with the other nipple. The pain was excruciating. Eventually Freeman stopped, looking at Tim's very swollen nipples, he seemed satisfied, "A little better."

Freeman was enjoying this, he wanted to cause Tim even more pain. So to avoid any embarrassment buckled on a large black ball gag. He then the bound Tim spread eagled onto a padded table. He pulled up Tim's dress so his knickers were exposed, and the kneeled between his legs. Freeman felt the inside of Tim's thighs. He didn't think he had ever felt skin so soft. It was just asking for some punishment. Freeman started by hitting them with a ruler, then rolled a Wartenberg Pinwheel up and down Tim's thighs. Freeman loved the feel as Tim winced as a pin stuck painfully into his thigh. Freeman traced around the edges of Tim's panties concentrating on the ultra tender skin between Tim's legs. At times Tim was almost frantic with pain. Freeman couldn't resist rolling the pins over Tim's penis. This made Tim jerk from side to side ever more violently. Tim's muffled screams were music to Freeman's ears.

Freeman then stripped off his shorts and sat on Tim's chest, taking off Tim's gag "Now Lucy my little slut. Take my cock and show me how an experienced whore gives fellatio." Freeman pressed his already erect cock into Tim's mouth. Tim did not resist and started to suck for all he was worth, getting Freeman's cock as far down his throat as physically possible. Freeman felt the bliss, it was as good a blowjob as he could remember. It was with great force of will that he eventually withdrew. He had other plans for his valuable cum. Now it was time to get the boy into bed, so he unbuckled his the leather cuffs and pulled him to his feet.

"Lucy, take your dress off and get on the bed. We are going to make love."

Tim struggled to get out of the dress, much to Freeman's amusement. When he finally succeeded he asked, "Master, would you like me to take off my lingerie?"

"No Lucy, you look fine."

Tim got on the bed and knelt down on all fours, spreading his legs. He wondered if Freeman was going to be vicious or gentle, he had better prepare for an aggressive fuck just in case. Freeman gazed at Tim, in his suspenders and corset, smiling from the bed. His pale skin contrasting with his black underwear and the satin sheets. Tim, knowing what was expected of him, looked up at Freemen and pleaded, "Master, take me please. I am your slut and I really deserve a good fucking. Please Master, fuck me."

Tim saw Freeman was very excited, so there was no need to warm him up. Freeman knelt behind Tim, feeling his silk panties, his fingers found the hole in the back and easily entered Tim's well lubricated arse. Freeman started fucking Tim slowly, then increased the pace and force. He showed a determined ferocity, this was more than sex he was going to totally dominate and humiliate Tim. Tim was now his slut, he had totally submitted. Freeman came with an explosion of ecstasy and a fountain of cum. Exhausted he rolled over and lay on the bed.

"Come on Lucy, where are your manners? Clean me up."

Tim knew what Freeman meant and started to lick his cock, sucking off all the remaining cum. Tim tried to show real enthusiasm over this, brushing his dishevelled hair out of his eyes as he tried to satisfy his Master. Tim's attentions inevitably meant Freeman soon recovered his erection.

As Tim saw this, he looked up at Freeman and gave him one of his horniest smiles, "Master you were fantastic, would you like to do me again?"

Freeman looked down at Tim, he was his. Tim looked a mess, but was still sexy as hell. The second time Freeman strapped Tim to the whipping horse and fucked him there. He was more aggressive, the sight of a restrained Tim made Freeman incredibly horny. He pumped away, knowing he wanted to hurt Tim. Causing him pain and humiliation gave Freeman great satisfaction. Eventually Freeman released Tim but ordered him to sleep in a 'slave basket' at the foot of the bed.

Tim woke up before Freeman. He was uncomfortable, sweaty and dirty, his knickers were still soaked with Freeman's cum. He got up, had a bath, put on fresh knickers, suspenders and stockings, redid his makeup as well as he could and put on a short silk dressing gown. He felt much better, returning to the main room, he waited until he saw Freeman stirring and then went off and brought him a cup of cappuccino and a croissant.

Freeman awoke to the smell of fresh coffee and the sight of a very fresh looking Tim. They chatted about inconsequential things. Tim was sitting on the bed, the tops of his stockings just visible below his short dressing gown. When Freeman was well awake, Tim asked him, "Master, I really enjoyed last night, can I do anything more for you?" 

Freeman was amazed that Tim was still offering himself after the exertions of the previous night. He knew his balls would be sore the next day but simply could not resist, "Yes Lucy, give me a good teabagging, but be gentle."

Tim stripped off his dressing gown while Freeman pulled the bed covers back. Tim got down and started licking Freeman's balls, he then opened his mouth as far as he possibly could and sucked them. Freeman's scrotum had quite a bit of action the previous night, but orders were orders and he got down and sucked as hard and as erotically as he could, massaging Freeman's balls with his tongue. He then moved on to give Freeman a conventional blowjob. Tim was relieved when he finally felt a gust of salty cum hitting the back of his throat. Freeman felt great but was totally and unutterably exhausted. He now felt he knew what a porn star went through. Freeman lay back and dismissed Tim.

After he had been released, Tim went to Miss D'Alquen's room and redid his own makeup. It took time but he was getting the hang of it. He put on some clean lingerie and chose a short summer print dress, so light in fact that it was almost transparent. Finally, he put on a necklace and some earrings. Tim was proud of his ability to pass for a girl and the way men lusted after him. He gazed at his reflection, a calm elegant feminine face looked back at him. Though he knew he was rather less elegant when he was kneeling on all fours letting some customer fuck the hell out of him. But it couldn't be helped, it was his job. Now ready for the final act, he walked to Freeman's suite to give him a fond farewell. Freeman looked pleased to see Tim again and they walked down to the marina together, initially arm in arm, then Freeman's hand eased its way into the back of Tim's panties.

As Freeman sailed away, he felt was elated. His time with Tim had been bliss; disciplining him and seeing the boy submit was wonderful. He would have to come back regularly, hang the cost. He hoped Tim would get to recognise him as his true Master if he booked him consistently. He thought of what he could do on his next visit, would he dress him up as a cheerleader or school girl? What other tortures could he think of? So many possibilities. He would be walking on a sexual high for weeks. But he really wanted more, he wondered if Astrid would sell Tim or rent him out for an extended period. He liked the idea of dressing him as a slut and making him work in the company's typing pool by day and disciplining and fucking him each night. **

As soon as Tim got back to his room, he logged onto the system to see when he was next booked for a date. This time the log-on screen was different, it had the normal icon for 'Tim' but now also had an icon for 'Lucy'. Tim clicked the second icon. Cartwright & Palmer had already uploaded the photographs he had posed for, there were a few of him in the maid's outfit, a couple in the latex dress and quite a few of him naked or just wearing panties. The latter shots were taken in such a way as his cock and tits (or lack of them) were always hidden by a strategically placed arm or leg. Tim was deeply impressed. He looked so damned sexy and feminine. Tim was pleased to see Miss Christensen had kept her word and 'Lucy' was priced at premium Grade one rates.

Tim got himself a drink, put his feet up and relaxed. He didn't change, he wasn't sure if this was due to laziness or the fact he now felt pretty comfortable in a dress or both. He was therefore dressed as Lucy when Jessica came to hear his war stories. Initially she did not recognise him, but when she realised it was him, she found it hugely erotic, insisting Tim spoke in his feminine voice and acted as a girl whilst she asked him all about his dates. They looked a beautiful couple when Miss Christensen came to congratulate Tim on his performance.

Eventually his visitors left and Tim stripped off and hung his dress with his rapidly increasing collection. He saw they had left him a whole draw of the silkiest female underwear. Tim lay back and wondered if he was likely to have many dates as 'Lucy'. By the look of the quantity of underwear they had given him, Miss Christensen must think he was going to be popular. He had only agreed to do work as 'Lucy' until Jamie returned which was only a couple of weeks away, but one never knew he might enjoy it. Was this the start of a whole new lucrative career?

*

** In the end Freeman got his way and Tim spent a fortnight working as his secretary. Tim found Freeman had bought him a huge amount of lingerie from brief lacy knickers to revealing negligées, as he expected Tim to be a girl 24/7. For work, Freeman dressed Tim in black underwear, a white silk shirt and either skin-tight leather hot-pants or the shortest latex skirt imaginable. Tim was now used to his role; his purr was sexy and decidedly feminine, his makeup was perfect and he walked in stilettos as if he had been born in them. Even so, he still felt very self-conscious as he slung his handbag over his shoulder and set off for work. His skimpy clothes and statuesque figure always attracted no end of unwelcome attention. 

Mid-week there was something of a scandal when Tim was caught, shorts around his ankles, being spanked by Freeman. Later colleagues who visited Freeman's flat for dinner were greeted by Tim in a very brief maid's outfit. The office gossip said his favours had been made freely available after he had served liqueurs. Although his fellow typists now considered Tim something of a tart, they never doubted his femininity. As such, he was quickly accepted and by the end of the first week Tim was enjoying being 'one of the girls'. Freeman took his new secretary to a variety of social functions in the evenings, dressing Tim in ever more revealing outfits. When they got home, Tim would strip down to his panties and allow Freeman tie him up, beat him, then fuck him senseless.



Tim Ch. 04



This story continues on from "Tim Ch. 3 -- Tim serves as a kinky French maid & is punished & humiliated.". This chapter works as a stand-alone story. 

*

It was now almost two years since Tim had been kidnapped and forced to work as a submissive sex slave. In that time he had accepted his status as a plaything for rich women and had got used to satisfying their pleasure and their often sadistic fetishes.

After a couple of dates on the island, Mrs Bergonzoli asked Tim to join her for a weekend away. Tim had to get express permission to leave the island, but by now this was something of a formality. He kitted himself out in a cute pair of tight white shorts and a blue and white striped T shirt and made his way to the marina. When he found her yacht, he was slightly surprised that Mrs Bergonzoli was not on there to meet him. The Captain apologised and said he had orders to take Tim to her villa near Palermo. The yacht slid through the water at a truly exhilarating pace. Tim had always loved the sea and he revelled in the freedom and the feel of the salt water spray in his face. As he chatted to the Captain, Carlo Bergamini, he reflected that life was treating him well. His client was a sweet old thing and he was looking forward to living it up at her sumptuous villa for the weekend.

Carlo drove Tim to Mrs Bergonzoli's villa. He was met by a very ill looking client. Normally Mrs Bergonzoli was friskiness personified, she would normally have him naked in minutes. This time the only thing measured in minutes was the time between her visits to the bathroom. She explained she had food poisoning and would be in no fit state to do anything much for the rest of the day but hoped she would feel better on the morrow. Tim felt guilty, what could he do to please her? He offered a massage and was about to suggest something more erotic when Mrs Bergonzoli went to the bathroom for the third time.

"Tim, it is sweet of you, but really I am no use to man or beast. Go down and keep my daughter company. She has been sulking all week and as you aren't 'bloody ancient' she may talk to you. Remember you are my research assistant helping me with my book on Lampedusa, in particular his stay in London. If I feel better I will send my maid down."

Tim went to the kitchen and introduced himself to 'Pippa'. Pippa was a pretty, with long dark brown hair, aged about eighteen. She was dressed in a shapeless T shirt and track suit bottoms and was 'reading' some fashion magazine. Her English was perfect and she quickly perked up when she saw Tim, asking him about what he was doing for her mother and how long he was staying. Tim lied like a politician. Pippa said she was off out to play pool with some of her friends and invited Tim to join them. Tim said he had quite a bit of research to go through with Pippa's mother and she had better OK it with her first. After much pleading on Pippa's part, Mrs Bergonzoli eventually agreed.

Pippa and Tim took a taxi over to another villa to meet a couple of Pippa's friends, Natalia and Louisa. They were all sitting in the living room chatting when Pippa turned to Tim and said, "Strip."

Tim was totally nonplussed, what had happened to the sweet Pippa and the casual evening playing pool? Before he could gather his thoughts Pippa continued, "Tim, you heard me, take off your fucking clothes now." Again Tim did nothing, he did not refuse but part of him suspected that this was a great wind-up and the girls would soon burst into laughter. 

But no laughter came, in fact Pippa looked more serious, "Tim let me explain things; first my step-mother said you should obey my instructions (yes, I heard your conversation). Second, I know you aren't a research assistant you are a prostitute, my step-mother uses the same password for all web sites so I have seen your page on Cartwright & Palmer's site (and so have Louisa and Natalia). Call me a stick in the mud but last time I checked, 'research assistants' tended not to pose naked and offer a myriad of sexual services on their web pages. So you are being paid to whore not to play pool, it is just I am going to take advantage of your services rather than mum. Lastly, if you don't obey me I will tell my step-mother you tried to get us to take drugs. It will be the word of a prostitute without ID papers against three blameless innocent girls. I suspect you will get six months and after serving your sentence you will be deported. I wonder what sort of welcome you will get from your employers. The American term for your decision is a 'no brainer', so strip. Now."

As Pippa was speaking she hit the remote control and to his horror Tim saw one of his Cartwright & Palmer videos appear on the TV, he was naked and was being whipped. He knew he could not play the outraged innocent and was well and truly beaten, he merely hoped that the girls would relent and explain it was a joke, but as he gradually removed his clothes, there was no sound from the sofa. The girls simply stared. Eventually he got down to his underwear and stopped. 

"Tim come on don't irritate me. Knickers off." With huge reluctance Tim complied.

Pippa threw a slave collar onto the floor in front of Tim, "Put it on and kneel." Natalia and Louisa had remained silent throughout, it was clear that Pippa had told them of her plans but at the same time they looked amazed that it was really happening. 

Pippa picked up Tim's brief black knickers and started to play with them, "Tim, what do you normally call your clients?"

"It depends how they wish to be addressed, but often 'Mistress'."

"That is how you will address; Natalia, Louisa and I. Now, hands behind your back."

Tim did as he was told and Pippa rose from the sofa and secured him with some heavy-weight handcuffs. She then chained Tim to a radiator. After all this planning she was not going to let him escape. Tim was left kneeling in the living room as Pippa and her friends went upstairs to change and get themselves ready. 

Natalia came down first, in a very short, tight black latex miniskirt and a brief bikini top. She had never seen a man naked before and wanted some time alone with Tim before the other two joined them. Pippa had shown her the Cartwright & Palmer web site months ago and she had spent every free moment gazing at the whores, but she had never imagined that she would see one in the flesh. He was gorgeous. She wished she could have him as a boyfriend. Kneeling there in his collar he reminded her of her fantasies about Roman slave markets. Natalia gazed at his lithe naked body, his pert buttocks and shaved pubic area. She felt an almost irresistible urge to touch his cock, but didn't quite dare go all the way. She knew Pippa wouldn't have any scruples. 

"Pippa says you were sold into slavery."

"Yes, Mistress. I was taken almost two years ago."

"So you have been doing this since then? Why don't you escape?" Without thinking Natalia added, "Tim, I would help you."

"No Mistress. They would find me, they always do."

Although Tim was trying to look relaxed, Natalia felt there was huge sadness behind his smile. God, she just wanted to hug him, he looked so innocent and vulnerable kneeling there, naked.

Tim felt very self conscious, he found submitting to a girl his own age much more difficult and humiliating than doing the same to an older woman.

Natalia looked around and saw Pippa and Louisa coming down the stairs in their PVC get up. Pippa had always been 'primus inter pares' but now she was really in charge. It was pretty obvious S&M was a huge turn-on for her. She tried to hide it saying it was all a joke but Natalia knew she was on a monumental sexual high. She knew Pippa had planned this night in some detail, even down to giving her mother some very dodgy oysters. She had made it clear Tim was her boy and she would call the shots.

Pippa stood just in front of Tim with Natalia and Louisa on each side. Louisa was in a very short, figure hugging, PVC dress. She was fingering a leather cat o' nine tails. Tim was only inches away from Pippa's latex dress. She looked down at him, almost breathless with desire. She was nervous but determined not to show this.

Pippa whipped out her phone and photographed 'her first slave'. Tim tried to avert his gaze, in part because of the acute embarrassment of kneeling naked before her and also in the hope he would not be recognised in the photo. Her trophy recorded, Pippa flexed her riding crop, "So Tim, you are now our slave. Spread your legs." Tim began to move his knees apart. Pippa continued to slap the inside of his thighs with her riding crop to show she wanted Tim to spread his legs ever wider. 

"To show you now understand your status, kiss my shoes." Tim bent forward and just managed to reach Pippa's shoes and kissed them. He knew he was in no position to resist her demands.

"Stand." Pippa then forced her riding crop between Tim's legs and thrust it up. "Tim you will obey our every whim or you will be in a lot of pain. Some people were born to rule and some sluts, such as you, were born to serve. Do you accept our superiority?"

"Yes, Mistress."

"OK, Louisa, release the chain and his handcuffs. You had also better give the poor boy some knickers. Tim, when you are not serving Natalia or Louisa, you will kneel at my feet."

Natalia stared at Tim's bottom as he went to get them some beers. He looked so good in the knickers they had chosen, so tight against his perfect bottom. Natalia did not know how they chose slaves, but having a luscious arse must be important. She smiled at the apron Pippa was forcing Tim to wear when he served them, he looked so sweet.

When he returned, Tim knelt at Pippa's feet. She fed him olives and chorizo as they watched a DVD. He was her pet.

Louisa turned to Pippa and said, "Let's have some fun."

"OK, I am going first. Tim, stand up and take off your apron and knickers."

Pippa approached Tim and fastened a chain to his collar. The chain fell down Tim's chest. Some six inches down the chain were two smaller chains. Pippa took them and Tim saw a large clamp on each, in fact he felt the clamps before he saw them as Pippa attached them to his nipples. Pain shot through Tim's body, but worse was to come as Pippa knelt and attached two similar clamps to his balls. Tim squealed with pain.

"Tim, do be quiet. This is a slut's uniform and you are a slut. On your knees." Tim did as he was told, all the time watching Pippa as she placed his knickers in the middle of the room. "Now Tim, crawl over and pick up your panties. You will need them by the end of the evening." 

Tim got down on all fours and began to crawl to the smiling Pippa. Suddenly he felt a painful tug to his balls and nipples and stopped to reduce the pressure. From behind Louisa whacked his bottom, "Come on slave, your Mistress told you to crawl. Don't disobey her."

Tim moved forward, knowing Louisa must have attached the chain to a piece of elastic. Pippa and Louisa giggled as Tim realised his predicament. If he didn't crawl forward Louisa would whip him for disobedience but the more he did, the greater the strain on his balls and nipples. He did not have much time to think as Louisa struck him again. "Come on you slut, you want your knickers don't you."

Tim swallowed and crawled forward. The pain particularly to his nipples was intense, but he was only a couple of feet away from his knickers. Tim moved forward again and made a lunge for his panties, he was just too short. One more pace. As he took it, Pippa nudged the knickers forward a few more inches. The pain was now almost unbearable. Tim couldn't continue. Louisa laughed as she whipped him again and again on his exposed bottom. Tim took a deep breath and moved forward again, neck out as he tried to get his knickers. Success, he got one corner in his teeth. He quickly moved backwards to relive the strain on his balls. God was he relieved.

"Well done Tim. It wasn't that hard was it. Kneel." Tim did so, knickers still in his mouth and faced Pippa. She crouched down and kissed Tim softly before taking the clamps off. Tim felt another shot of pain as the blood returned to his nipples and scrotum. 

Tim swallowed hard trying to recover his calm. He looked up and saw Natalia staring at him. She smiled, she now knew what slavery meant. Natalia had never seen someone submit. She heard Pippa's threat and knew it was serious but was still amazed at the result. Pippa and Louisa were determined to humiliate the guy and to her surprise watching this was fun, Natalia was now very turned-on. The thing was Tim was so beautiful and looked very willing to please.

"Louisa, your turn now, but give the poor boy a few minutes to recover. He looks rather fetching nibbling his knickers."

After what seemed no more than a heartbeat, Louisa ordered Tom to bend over the back of one of the chairs. Tim knew the score. He bent over, legs spread and pushed his bottom out. Louisa admired him, then stuffed his knickers into his mouth.

"Remember Louisa, no marks."

Louisa picked up a long wooden paddle. The first stroke was not too bad, the second was worse, the third was agony. Tim cried with pain. Louisa continued to strike Tim, much harder than the normal 'erotic' beating he normally endured.

After about a dozen strokes, Pippa went up behind Louisa and gently restrained her, "OK, I think that is enough for the poor boy. I want my slave to be in one piece at the end of the evening." Louisa who was in an erotic world of her own looked around disappointed, but she did not defy her friend. She had got huge enjoyment out of beating Tim and was determined to have a few more sessions before the night was out. She knew she had found her fetish, she would never manage to look at a boy's bottom in the same way again.

Tim was very relieved and fell on his knees, hoping Pippa would allow him a rest.

"My turn now." said Natalia, "Tim put your knickers back on and follow me." Tim winced as he pulled his tight knickers up over his now extremely painful bottom.

Pippa looked up, clearly Natalia was not happy playing with Tim in public. She was not that surprised, in fact she was amazed that Natalia had agreed to participate at all. "Remember what Angelo said, no sex and no visible marks. We had better be going soon, so don't take too long."

Natalia led Tim to her bedroom. Tim looked around, it was still 'girly' too many posters and far too many teddy bears. He wasn't sure what she had in mind so fell on his knees to be safe.

Natalia, surprising herself with her own courage, undid her bikini top and lay on the bed. "Tim, you have some work to do. Start by licking my tits."

Tim pushed her stuffed kangaroo onto the floor as he clambered on the bed, straddling Natalia. He barely allowed his tongue to touch the nipple. Gradually he moved closer licking the nipple properly. Tim would periodically stop and blow on the now terribly sensitive area. Natalia squirmed with pleasure, Tim was so sensitive, so caring. She began to breathe deeply, trying to conquer her huge arousal.

"Tim, my pussy." Tim eased his hand up her tight skirt and began rubbing her clitoris. 

"More, more Tim." Tim was now getting excited, whilst still sucking her breasts, he pushed her knickers aside and gradually inserted his fingers into her now well lubricated pussy. Tim moved down the bed and started licking Natalia's clitoris. He felt her intense heat. Returning his attention to her tits he kept massaging her pussy.

Natalia had never felt so turned-on. She knew what Pippa said but damn it, it was her house and Tim was as much her slave as Pippa's. She whispered, "Fuck me Tim, but please be gentle."

Tim had taken many a girl's virginity. Concerned mothers would often bring shy daughters to the island so they could be sure their first sexual experience was enjoyable. He pulled Natalia's knickers to one side and gently entered her. Tim was very slow and considerate. Natalia felt immediate pain, mixed with the most intense pleasure she had ever felt. The combination was incredible. 

She shouted, "Don't stop, keep on going." Tim did as he was told and gradually pushed his whole penis in. Natalia screamed with ecstasy as he pushed into her again. 

Just as he was going to pump a third time, he felt incredible pain in his bottom. Pippa was standing by the bed, as Natalia tried to cover herself, Pippa screamed, "Nat, he's mine. I decide who he fucks and when. Remember what Angelo said, 'no sex' before the club. There will be lots of time for that later but you fucking ask me first. Now clean yourself up, you slut. We will be leaving soon. Tim follow me."

Natalia knew she should not have fucked Tim without Pippa's agreement, but talk about temptation. No one with a heart (or a pussy) would blame her. As Natalia got ready, she mused on how well Pippa's plan was going; first threaten Tim, then get him to strip, humiliate him and finally punish him. Pippa said if they could do all this Tim would become submissive and so it seemed. She thought maybe Tim should continue as a slave, at least for a bit longer. He looked so damned cute kneeling before her. She wanted him again, badly. Perhaps next time he should get a spanking ...

Pippa led Tim to one of the villa's luxurious bathrooms. Tim sighed with relief, hoping for a few minutes on his own, to rest and examine the damage the girls had done. But he was quickly disabused of such hopes. Pippa and Louisa wanted to watch; privacy was one of the first things you lost when you became a slave. 

Tim undressed and showered. He felt the sting of the hot water on his sensitive nipples and bottom and heard Pippa and Louisa's giggling. Clean, he got out of the shower and was handed a towel by Pippa. This was a mere temporary relief, as she was insistent that he did his shaving and hair naked. 

Pippa watched Tim's taut buttocks as he shaved. She had done it! She had a slave and he was so damned sexy. All that planning was now paying off. The amazing thing was that Tim seemed to accept her authority without question. Her threats must have been convincing or perhaps he was genuinely submissive as the website said. 

When Pippa was happy with his appearance, she allowed Tim to put on his knickers and collar.

~

They piled into Louisa's car and headed for the ancient part of Palermo, near the docks. They parked the car and proceeded to the club, as they turned a corner they almost bumped into a Carabinieri patrol. The senior policeman looked at the girls and more to the point Tim, in his collar and bikini. Tim did not understand the conversation, but it was pretty evident the policeman was asking what Tim was doing walking around Palermo in his underwear. He kept hearing words repeated with some emphasis, "Spogliarellista ... sorella ... addio al nubilato ... mutandine ... bagascia."

Eventually the policemen irritably waved them on. Louisa looked relieved. Tim asked her what it had been about and she explained, "Pippa said that you were a stripper for her sister's hen party. Whilst the policemen thought you were a whore. He was going to arrest us until he found out Pippa's name was 'Bergonzoli'. Clearly this made him think, so he told us to get you off the street pronto. Wow, I really thought we were in trouble then, he didn't really look the liberal type."

Bar Bardia was a dive, its dim lights and collection of low life had a certain seedy glamour. The bar was full of dark corners and had fetish scenes and portraits of some of Sicily's most brutal murderers decorating the walls. Tim was particularly struck by the unusually large number of tough looking women. Tim could imagine how it was heaven to Pippa and her friends. The fact they had him to show off, as they tried to act as if they part of the underworld, could only have added to the ego trip. Tim was no retiring violet, but even he had never seen people like this; whores, junkies, fairies, pimps and those who contravene pretty well ever clause of every act on the subject of theft or sexual vice. A zoo of perversion. Even the hardened clientele were staring at him, kneeling at the girls' feet in his bikini bottoms and collar. The girls stuck out, three innocents in an ocean of vice. They were clearly trying to look confident and relaxed but their naive posing only emphasised how unutterably out of place they were. 




Tim Ch. 04



Tim was amazed that they were allowed entry until the barman or owner came over. It was clear that 'Angelo' was related to Natalia, as ever Tim's Italian was not up to working out the exact relationship but he guessed, brother, half brother, cousin or the like. After a few hugs Angelo asked about Tim, again Tim did not understand the answer, hearing the word 'mignott'. This seemed to surprise Angelo but he accepted it and after some form of pretty serious warning he left.

Tim's knees were aching from kneeling at Pippa's feet. She stroked his hair and gently squeezed his nipples. The girls were clearly having a ball of a time, basking in the attention that Tim was bringing them. They really thought of themselves as little gangsters.

One of the staff arrived and started talking to Pippa, more Italian that Tim did not understand "Leccacazzi ... bagascia ... orecchione." Eventually the guy took out a wad of Euros and gave them to Pippa, he then motioned Tim to follow him. Tim was taken to a small raised area and his hands were buckled into some wrist cuffs suspended above his head. The man said 'Ballo', or something like that. As ever Tim did not understand, until the man grasped his hips and pushed than back and forth. Tim realised he was meant to 'dance'. He looked around and saw a number of other platforms with girls gyrating away, so Tim tried to copy.

He looked over at the girls and saw they were staring, they seemed surprised at their own bravado. Tim tried to look away and wiggle his hips in as erotic way as he could. The barman came over and yanked Tim's head back and poured most of a bottle of beer down his throat. Tim could not swallow quickly enough and felt the beer pour down his near-naked body. The liquid glistened when the roving spotlights fell on Tim's chest, thighs and bikini.

After about half an hour, another member of staff came up to Tim and unclipped his wrist cuffs from the overhead chain and then reattached them behind Tim's back. He then threaded a chain he was holding through the loop on Tim's collar. Tim was then pulled to the other platforms where the barman repeated the procedure with the girls. When Tim and the four girls had been securely fastened to the chain they were paraded around the bar. As the bar was full they had to force their way through the crowds. Tim felt numerous hands massage his balls and butt, he was public property. They were presented to the corner tables, first their fronts then they turned showing their bottoms. The most embarrassing point was when they were shown to Pippa and her friends. Louisa made some obscene joke that the barman enjoyed. 

When their tour was finished they were taken to a roped off part of the bar where they were released and offered bottles of beer. It seemed surreal to Tim to be standing chatting in a bar wearing a tiny bikini, wrist cuffs and collar. The barman returned with a large tub of gel. The girls quickly stripped off their bottoms and Tim realised this was lubricant and they were expected to prepare themselves. Tim was too slow to claim one of the chairs and had to stand and spread his legs to lube himself up. A crowd quickly appeared. One particularly loud group of girls, hearing Tim speak English, called him over. Tim knew he would get no peace if he tried to ignore them, so wandered over, making no attempt to hide his almost total nakedness. He started chatting, brushing his hair out of his eyes to make sure his hands didn't inadvertently fall to his cover his tiny bikini.

As Tim was chatting away he was tapped on the shoulder by one of his fellow 'dancers'. She had pretty, open, almost innocent face and shoulder length blond hair. Her body was beautifully toned, and she moved with a freedom that indicated this was hardly her first time walking around a bar pretty well naked. Tim thought she was probably Eastern European from her accent. "I thought you needed rescuing. Anyway my name is Natalya."

"Tim."

"I haven't seen you in the club before. Has anyone explained what will happen?"

Tim admitted he hadn't the faintest idea of how things would pan out. "Well, we will be auctioned. We go up on stage, dance for a few minutes and strip. Technically the auction is for an hour of our company, but you know what that means. As you can guess looking around, some bidders have some pretty unusual fetishes and you are expected to do anything they ask. Are you OK with that?"

"I am not sure I have much choice." 

"I come here and auction myself every Friday and Saturday. The auction brings in quite a few dates for the other days as well. I suppose my only real advice is that the higher the bid the better chance you have of a normal date. The real low-lives in my experience tend to be poor."

Tim watched the first girl, Mariella he thought her name was, get up on stage. He quickly realised that she had not been trained as a pole dancer. Pretty, but an amateur. As ever Tim did not understand the Italian that the bidders were shouting. But they seemed enthusiastic for an hour of her 'company'. When the bidding finished the girl was walked naked over to one of the tables and sat down with a raucous party of men.

Natalya was the second to go. When her bidding had finished she was taken back to the roped off area and her hands were secured behind her back.

Tim got nervous as the barman indicated he was next to go. He knew he should be confident, as he had been taught how to strip and pole dance at Cartwright & Palmer. He had regular spots at the clubs on the island to ensure he didn't forget his moves. But things were different here, he was worried the stage was much smaller than he was used to, he was also unsure how the audience would react.

The barman led Tim through the crowd. Tim walked around the stage and bent over gently pulling his bikini down then back up, so the audience could see more and more of his bottom, teasing the crowd. He then started to tug the cords at the side of his bikini. One of the bows came undone, but before the bikini could fall open, Tim clutched the cords in his right hand. The left bow then came undone and Tim let the bikini fall. He clutched the pole hiding behind it, moving his head from one side to the other and wiggling his buttocks but always ensuring his cock was almost covered. As he moved he allowed the audience to see more and more of him, until he grasped the pole with his outstretched hand and with his feet resting at the base of the pole, swung around the pole, first one way then the other. Tim now made no attempt to cover his nudity, he was for sale and potential bidders had the right to see him, all of him.

Tim then stood at the edge of the stage with his back to the audience and gradually spread his legs. As he did so, he bent forward so his fingers touched the floor in front of him. When the audience were expecting him to do the full splits, he pulled his legs together and sprung up, so he was doing a hand stand, resting his legs against the pole. Tim then clutched the pole between his calves and proceeded to bend at the waist, this was the difficult part of the routine, eventually he was bending almost double and grasped the pole above his feet. When he felt secure he released his calves and proceeded to spread his legs so his was doing a mid-air splits. Keeping his legs horizontal he gradually slid down the pole. When he was a couple of feet from the floor, he nimbly dropped onto the stage and finished on his knees in the centre of the stage. Tim always felt a great relief when he finished the routine. He had done it many times before but it always stretched his muscles. It was meant to show his strength and flexibility, he hoped it impressed his audience.

Again he heard some bidding he did not understand, but at least there were some bids. In time the barman returned and before Tim could put his bikini back on he had attached a chain to Tim's collar and led him back to the roped off area.

The next girl returned and without a word got dressed and left with her 'date'. Tim did not see the last girl and assumed she had remained in the bar naked.

Soon after the auction ended a guy in a black T shirt came over and started talking to Angelo. When he had finished he came over to the kneeling Natalya and Tim and handed them small blue bikinis and told them to stand. He then secured their wrist cuffs behind their backs and attached a chain to their collars. Tim wondered what sort of 'companionship' he would be giving.

As Tim left he looked over and saw Mariella standing in front of the table playing with a dildo, gradually pushing it into her pussy. The guys were loving it.

~

When they got out into the street, the cold air hit Tim hard, he was almost naked in the middle of Palermo. Natalya was topless and seemed even more uncomfortable, but their guide took no notice of her protest. There was little they could do, if they resisted they would only attract more attention and with their hands firmly secured behind their backs, they had no chance to defend themselves. Tim and Natalya walked up the street conscious of the stares of those passing in the opposite direction.

Eventually, after what seemed like an age they arrived at a large town house. They were ushered in and told to wait, kneeling, in the lobby. 

The hall was full of people rushing around, it was pretty evident that they were preparing for some dinner or party and Tim guessed he was likely to on the menu. At the centre of the melee was a woman who was clearly in charge. She was tall, probably in her late thirties, attractive with long flowing brown hair. She carried a riding crop and was dressed in tight white trousers, a white silk shirt and calf high boots polished to perfection. She looked used to being obeyed, but was not as relaxed as she appeared. Xaviera knew she still did not have enough whores, why the hell had Francesco, Josephine, Darcy and Mirabelle not turned up? She turned to one of her assistants, "Did you speak to Madame Giordano?"

"Yes Mistress, she agreed to send Bambi. She said she could only spare one girl at this notice."

"OK, we need at least one more boy. Go to the Saporetti Sauna. There are always whores there. You know the score, I want a boy who speaks English, has some sophistication, is bi and is prepared to take a good beating. I'll pay them three K for a night's work."

As the assistant ran off, Mistress Xaviera turned to Natalya and Tim, "So this is the Bar Bardia contingent. According to Angelo you are professional whores and speak English. What is your sexuality and do you submit? There is a good bonus in it for you, if you perform."

Tim suspected that Mistress Xaviera would take by force anything that was not offered voluntarily, so he had decided to submit but before he could say anything Natalya piped up, "I'm bisexual and it would be a pleasure to serve, Mistress."

"And you, Tim?"

"I'm bi and would also be happy to serve you, Mistress."

"Good, sensible decision." She attached tags to their collars, Natalya was now 'eight' and Tim 'nine', "Florentina will give you your uniform and explain what is expected of you." Waving to a girl the other side of the room.

Florentina was also wearing skin tight white trousers, a white silk shirt and boots. She handed Tim and Natalya their uniforms, and watched as they put on some brief white satin knickers and a white satin T shirt. The shirt was short so it left Tim's perfectly flat stomach on show. 

"Tim the garter goes on your right thigh. It is for tips." Tim adjusted the white garter as he was told.

"OK, Tim, Natalya? You may look like a pair of virgins but our members expect total obedience regardless of the pain or humiliation they mete out. No limits, no refusals. If you comply you will be generously rewarded, if not ... well let's not go there. You are their playthings for the night. If they were not being played-with you will kneel on a small stage at one end of the dining room and wait for my or Mistress Xaviera's instructions." 

Tim and Natalya joined a group of seven whores, six girls and one boy, nervously waiting for the start of the proceedings. They were all wearing the same uniform. They were led into the dining room in numerical order. The room was in the Louis Seize style, as interpreted by an educationally challenged Mafioso. Gaudy, tasteless but still strangely impressive. Tim was the last, as he knelt he heard Mistress Xaviera say, "Tim is a fresh young life-style submissive. He loves the riding crop and the firm hand of authority. Tim is broad-minded, bi-sexual and very eager to please."

Tim bowed his head but just managed to make out that the table sat about a dozen guests, about two thirds of these being male. They all wore formal evening wear. An older man sitting in the centre of the table rose and said, "As is traditional, our newest members have the privilege of the first choice. Therese, who would you like?"

"Henri, thank you. I think I will go for number nine."

"Charles, what about you?"

"Number four, please."

Mistress Xaviera tapped Tim on the shoulder with her riding crop and motioned that he should rise. She led him over to a padded hurdle and buckled his wrists and ankles into some restraints. She roughly pulled down his knickers.

Therese rose from the table. She was pretty girl with her hair pulled back in a rather severe style. She was wearing a dark green strapless evening gown and a chocker of pearls. Therese picked up a riding crop and gave Tim what might be termed a 'sighting shot' right in the centre of his bottom. She then followed this with three more strikes in rapid succession. Tim could not suppress a cry of pain. The woman was not posing, she wanted to hurt him.

"I can't whip him with this bloody dress on. David be a darling and help me out of it."

Her companion, unhooked the back of the dress and she stepped out of it to reveal a satin corset, stockings and the briefest pair of knickers. Her fellow diners gave her a round of applause to which she responded with a quick curtsey before returning to Tim. It seemed she was right, her dress had cramped her style and she started to whip Tim with much greater vigour. She started on his buttocks progressing to his thighs. Tim knew he should try to keep silent but the pain was simply too great he squealed with anguish. Initially he felt and counted each stroke, but after a time his buttocks just felt like a huge expanse of pain. After a particularly hard strike and the resulting shriek of pain, someone forced a ball gag into his mouth. 

Eventually Therese seemed to tire and finished her whipping, she kissed Tim on the cheek and left. One of Mistress Xaviera's assistants released him. Tim then made his way to the dais, as he did so a middle aged man motioned him to approach. The man was in conversation with a lady and a younger man. They continued their conversation as if his presence was of little interest.

"So you are one of Xaviera's new sluts?"

"Yes, Master."

"Kneel and suck me."

Tim did as he was told. The man seemed to be not in the least self conscious of having Tim unzip him and remove his penis. Tim started by gently stroking the man's cock, as it became erect he put it in his mouth and started to suck. As he did so he continued to massage the shaft and play with his balls. It was still early in the evening and Tim was keen to be seen as enthusiastic, as he could see Mistress Xaviera looking on and there were far too many whips around for his comfort.

As Tim worked up a good rhythm the man continued his conversation. He quickly became silent and started to sigh with pleasure. Tim felt a sudden jerk and his mouth filled with cum, he redoubled his efforts as his swallowed. His efforts were rewarded by further ejaculations. Tim was now sweating profusely with the effort. After a few more minutes the guy removed his penis from Tim's mouth and zipped himself up.

Tim remained on his knees as the three continued their conversation. The lady ruffled his hair as the three discussed some mutual financial interests.

Another lady joined the group and after a few pleasantries asked if she could 'borrow' Tim. This she did and led him from the dining hall and into a small bedroom. The room was small and dark. It only contained a bed and chair. The bed was a plain black design covered with bright red satin sheet. 

"Don't be embarrassed Tim. I won't hurt you."

Tim guessed at the role she wanted him to play. She had mistaken his innocent looks for an innocent mind. Tim sat on the bed with his legs firmly closed nervously playing with his garter. Miss Christensen always said, "Be whatever your client wants you to be." Tim remembered exactly how he felt on his first dates.

She sat down beside Tim and started stroking his hair, "By the way my name is Kate. I haven't seen you here before. Is this your first dinner?"

"Yes, Mistress."

Kate was slowly easing Tim's thighs apart, she then started to stroke his penis, "Call me Kate, my little one. It won't be so bad, I will be gentle I promise. Why did you start doing this?"

"The money ... Kate."

"One of the best reasons for doing any job. Just remember you are providing a service like any lawyer or accountant. It is just you are probably better paid and are a lot more fun to be with."

"Now to work. Stand in front of me." Tim did as he was bidden and Kate reached for his thighs, tenderly stroking them, her hands rose and she felt his buttocks before taking the sides of his knickers. She gradually pulled them down.

"OK, over my knee." Tim got on the bed and placed himself over Kate's knees, careful not to put his full weight on her, spreading his legs so she has easy access.

Kate felt his bottom, "Oh my poor boy, you have been given quite a beating. Therese was clearly not doing it for show." Tim enjoyed Kate's gentle massaging. Her hand gradually eased between his legs, massaging the sensitive area she found. She then moved on to his cock, which she began to rub with increasing intensity, until Tim was very excited. All of a sudden she stopped and gave Tim's arse a hard spank, the shock added to the sharp pain, Kate hit harder and quicker. She was evidently aiming for where Therese had whipped him. Tim squealed with pain.

"Tim, pain and pleasure. This is what makes the Roissy Society so special." She then pushed him off her knees and started to take off her clothes. Kate rolled onto the bed and spread her legs, "Tim, let's get down to business, start by giving my pussy a good lick. Remember that the only thing I enjoy more than taking an inexperienced boy to bed is giving one a good thrashing."

Tim got down on his knees and started to lick Kate's clitoris. As she became aroused he started to nibble and then penetrate her with his tongue. Tim worked with increasing urgency. Kate rapidly became excited; Tim heard her grunts of pleasure as she moved her thighs back and forth. Her breathing was loud and urgent and Tim knew she was close to climax. Then suddenly she pushed him away, "Tim, I need to save myself. Now's time for anal."

Kate repositioned herself onto her knees, spreading her legs. "Tim now, give it to me hard."

Tim gradually inserted himself, slowly at first, easing himself all the way in. When he became confident Kate was truly ready he increased the pace of his thrust, quicker and harder. Kate was already supremely turned on and quickly started moaning then shouting with pleasure. This time she wanted to be taken all the way. After her first climax she shouted, "Again, keep on going my little whore. Harder, harder..."

Tim continued to thrust and felt Kate climax again, then a third time. This was all she could take and she collapsed exhausted. She pulled Tim close, ensnaring his body with her legs. Tim felt the smoothness of her skin, the wetness of her pussy tight against his chest and smelt a truly satisfied woman.




Tim Ch. 04



"Tim, that was wonderful, truly wonderful. You will make a lot of women happy if you stay in this job. Please do, I want this again and again." Kate revelled in the physical ecstasy and the thought of her own depravity, how great it felt having a new whore take her like this.

Kate clasped Tim close and would not release him, but after a brief snooze, she knew she had better get back to the party, her friends would want to experience this.

Kate dressed and took the now naked Tim by the hand and took him back to the main dining room. She got a glass of wine and offered one to Tim. Kate sat on one of the sofas and made Tim kneel before her. They talked, initially Kate explained the history behind the Roissy Society, their monthly dinners and their stable of submissives. As she played with Tim's cock with her foot, she tried to convince Tim to become one of the Society's full time slaves. Their conversation was interrupted as they were joined by other diners, all still impeccably dressed in their evening clothes. It was almost like a normal drinks party, other than most of the guests were recovering from some form of sexual excess and Tim was naked except for his collar and garter. One guest (Carrie) approached and casually tweaked Tim's nipples whilst discussing a recent art exhibition.

When they were alone gain, Tim asked, "Mistress, can I find my uniform?"

"No Tim. You have a lot to learn about your new profession. You are here for our pleasure and my friends like seeing you naked. You will have to stop being so self conscious."

Eventually Mistress Xaviera came over, "How is your evening Kate? Has Tim done kept you entertained?"

"Oh yes Xaviera, I have had a wonderful time."

"Good to hear it. I am afraid I am a little low on boys this evening, can I borrow Tim for a bit?"

Kate knew that she should not monopolise Tim's time so it was with a heavy heart that she assented. She kissed him and stuffed a few notes into his garter. Kate thought it would be fair to try to reclaim him in about forty minutes. She really wanted to feel his tongue in her pussy once more that evening.

Mistress Xaviera took Tim to the dais and told him to kneel. She then kept him under strict supervision. It was, "Tim, go and ask that gentleman if you can blow him," and "That lady is called Jemima and she is staring at your butt, offer yourself to her," and "Here comes Carrie, prepare yourself for a hard whipping." Tim was running from one client to another. 

Tim was again kneeling on the dais when he was summoned by a lady in a bright yellow evening dress. She was a pretty blond with short hair parted to the right. Tim helped her out of her dress, to his surprise she was left wearing only a g-string and stockings.

She led Tim to the centre of the room, there she touched Tim's nipples, "So you are the new boy. My name is Tina. A slave must be able to take any punishment they deserve. Lie down, spread you arms and legs out."

Tina then sat on his stomach and started to lick his nipples. It felt wonderful, so deeply erotic that Tim quickly got an uncontrollable erection. This rested against Tina's buttocks. Her licking was so soothing after the abuse his nipples had endured earlier in the evening. Gazing into his eyes, Tina smiled as she produced a lighted candle and proceeded to pour boiling hot wax on his hard and erect nipples. Tim was shocked at the speed with which pleasure was turned into pain. His body jerked with pain as the wax dropped on his skin. The searing heat was incredible. Tina giggled at his pain. Tim tried to recover and spread his arms and legs out as ordered, but it took all his self control knowing the horrible pain that was to come. Tina dribbled the wax slowly, then waited and poured the accumulated wax on one of his nipples.

Tina turned around leaving Tim with the sight of her perfect bottom. She started wanking Tim, he quickly became erect again even though he knew what was to follow. Tina poured a little wax on the area just above his penis. The pain was immediate and so much worse than his nipples. Tim instinctively pulled his legs up in reaction to the pain and to protect himself.

"Tim, keep your legs apart, or I will give you a good beating for disobedience." Slowly Tim spread his legs again and as he expected Tina now poured the wax directly on the head of his penis. The pain was simply indescribable. Tim shrieked with pain to the great amusement of the gathering audience. As he doubled up in pain, he felt some vicious strikes of a riding crop as one of the other girls 'punished him for his disobeying Tina'. As the wax cooled Tim spread his legs again. 

This time Tina waited for longer, so the pool of molten wax on top of the candle was now even greater than before. She grabbed his penis and poured it all over his head and then on its tender underside. Tim squealed with pain. The heat was terrifying, he again pulled his legs up to protect himself and immediately felt the whip. He did not care, no whipping could ever compare to the pain that Tina was putting him through. Tina laughed as she saw his pain. She now started pouring wax on his balls, more pain. Tim was now sweating profusely, much as he tried he couldn't keep his legs spread eagled and was being whipped as a result.

The torture seemed to go on for ever. Eventually Tina got off him. Tim was so exhausted that he didn't move, he just lay in the middle of the floor naked as the diners looked on.

"Tim, don't lie around. Show some respect for your Mistress. Kiss my shoes." Tim got to his knees and gingery bent forward, trying to put as little pressure as he could on his balls. He then kissed Tina's shoes.

Florentina, one of Mistress Xaviera's assistants led Tim away to a shower. She then gave him an ice pack for his burning penis and nipples. When he had recovered and returned to the dining room the party was beginning to break up. Mistress Xaviera had the slaves line up by the door and thank the members of the Society for their company. Some of them reciprocated by slipping banknotes into Tim's garter.

The place looked like a battleground, with discarded underwear and bottles instead of guns and tanks. Tim looked for Natalya, eventually he found her bound to a whipping horse, as her arse was as silky smooth as before he guessed this was to allow the guests to fuck rather than to punish her. His efforts to release her were rewarded with a grateful hug. 

As Tim approached Mistress Xaviera, he saw a gagged boy suspended from the ceiling, his toes just touching the ground. His legs held by a spreader bar and huge weights were suspended from his cock and nipples. He had clearly been beaten without mercy. Dark red stripes covered his whole body, his buttocks had received particular attention. Tim wondered what he had done to offend Mistress Xaviera. 

Mistress Xaviera noticed Tim's gaze, "Don't worry about the slut. We will release him in the morning." Tim knew the poor guy would be in quite unendurable pain by then. As she handed over a thick envelope, she said "Tim, you did well. I would like you to come to the next dinner if you are in Palermo in November."

Now Tim started looking for his clothes, he couldn't find anything until he remembered the guy still chained to the ceiling. He realised he wouldn't need any clothing for hours and was not really in a position to stop Tim borrowing whatever he needed. Eventually he found a pile of clothes and dressed in the guy's yellow PVC shorts and blue 'off the shoulder' polyester T shirt. He didn't feel great but it was this or walk naked through one of the roughest areas of Palermo. Natalya found a discarded bra and a pair of panties.

Next time he passed, the guy was looking very distressed. Tim was unsure if this was because he saw his clothes had been stolen or if it was due to the pain of being fucked by one of the waiters who could clearly not resist his unprotected bottom. Tim saw a group of men milling around evidently in some sort of queue waiting to sample the same favours.

When Natalya got back to Bar Bardia she found her clothes and dressed in the bar without embarrassment. As she stuffed her own underwear into her handbag she wondered whose panties she was wearing. They were wonderfully silky, fitted well and were rather above her price band. She assumed they belonged to one of the other whores. The underwear had to be squeezed into the bag due to the size of the 'brick' of cash that Mistress Xaviera had given her. Over four grand for one night's work. She was sore from a lot of sex but for that money she did not care. She could almost live off that for the rest of the month. She jumped at the chance when Mistress Xaviera offered her a place at the next dinner. No more cheap dates with cheap punters, no more fifty Euro hand jobs, no more selling herself on the street when the rent was due. As she chatted to Tim on the way back he mentioned he worked for an agency where she could make that kind of money and more, perhaps she would give Cartwright & Palmer a call.

When Tim arrived back in the bar he went to Pippa's table and quietly knelt at her feet. Pippa was furious at how long he had been away and as she pulled Tim to the door by his collar she swore he was going to pay. When she got home she ordered him to strip and was visibly shaken by the evidence of the punishment that Tim had endured. As a result she refrained from giving him the whipping she had been dreaming about. Pain or no pain she could not resist raping him. Pippa tied Tim spread eagled on her bed and after gagging him proceeded to ride him for all she was worth. 

Eventually she dismissed him. Tim was relieved that the evening had finally come to an end. But even after he had rubbed pain-relief cream into his buttocks, thighs, nipples and penis he still found it very hard to get to sleep. 

The next day Mrs Bergonzoli quickly spotted that Tim's scars were very recent, this resulted in a furious row between mother and daughter. Tim wished he could have understood it, somehow he could not imagine his mother shouting, "You are too young to use my prostitute!" Eventually Tim heard the front door slam as Pippa stormed out of the house. 

Tim knew it was time to face the music and knocked on Mrs Bergonzoli's bedroom door and waited. He was frightened for the first time in ages, he was truly worried about his impending punishment, as he was sure that Mrs Bergonzoli would accuse him of corrupting her daughter. Tim knew there was a great difference between an 'erotic' punishment and when a client truly wanted to hurt you. The latter could be terrible. Tim took a deep breath, dropped his knickers and entered. He knelt in the centre of the room, eyes lowered and waited for the abuse to start, expecting the mother of all whippings that he knew in his heart he deserved.

Tim heard Mrs Bergonzoli approach and tried to look remorseful as she raised his chin to look at him. To Tim's surprise her face was not contorted with rage but had a gentle smile, "Tim you look in a bad way. You had better put on one of my silk night shirts and lie on the bed whilst I try to repair the damage you took last night." Tim was amazed. In the end Mrs Bergonzoli treated him like a sick schoolboy, mothering him for the entire day. They laughed and giggled their way through a couple of romantic DVDs and a good amount of foie gras and champagne. These being Tim's favourite cures for a badly beaten bottom. When it came time to leave Mrs Bergonzoli looked as happy as he had seen her in ages. Tim marvelled at the ever surprising life of an escort.

~

Tim pulled up his knickers as he looked in the mirror. He knew he was now a 'career prostitute' and to his surprise he was happy about this. He couldn't really understand the prejudice he had had against those 'on the game' before he found out what was really involved and the skills required. 

He was feeling confident; he had recently been promoted to a 'grade one', making him one of the most expensive boys on the island. He knew Astrid thought highly of him, both for his physical beauty and his versatility. He was equally attractive to men and women and could play the alpha male, the submissive and even a TV with equal skill, and more importantly his feedback was uniformly excellent. Two clients had even tried to 'buy' him for considerable sums. 

Eventually he would retire but there was no rush, he enjoyed his job and was very well paid, a pretty good combination. He knew his body would not stand up indefinitely, and some of beatings were very painful, so he had provisionally agreed a deal with Astrid whereby Jessica and he would work nine months on, three months off. He felt this would extend his career and hoped to work for another couple of years, eighteen months at the least. Then he was set up for life.

Tim looked at his watch, he had about twenty minutes before he had to get ready for Karen. She was becoming one of his 'regulars'. She always came for the weekend and booked Tim from lunch time Saturday to lunch on Sunday. She was one of the few clients who really treated Tim as an 'escort' rather than a prostitute. She seemed to want to relax; she had Tim accompany her to lunch, then they lounged by the pool together, after dinner she often only wanted a massage or a little oral attention to her pussy and tits. Tim knew she was no shrinking violet, as when they did have sex Karen showed she had an inventive mind to go with her beautiful body. She talked about a high pressure job and said how Tim was her 'haven of tranquillity'. 

After three dates Karen asked Tim to join her on her yacht. Tim was looking forward to the weekend, he enjoyed Karen's company and a relaxing weekend on a boat a perfect antidote to a hectic week. He passed through Security at the marina and wandered along a line of palatial yachts. Karen said her boat was a thirty footer called the 'Lady Isabel', he had no real idea what a thirty foot boat looked like, but it sounded large. It was, not quite 'Russian oligarch' size but certainly at the multi-millionaire level. In the end he was not embarrassed by having to try to make out the names as Karen shouted a greeting.

Karen, dressed in a brief red bikini, welcomed him aboard. She introduced him to the Captain, Sam Budyonny, and more to the point to her friend Caroline, a very shapely lady. Tim thought she was sexy rather than beautiful, in fact she exuded sex appeal from ever pore of her body; most of this was on show as her bikini was tiny. Caroline seemed very pleased to meet him.

Karen asked her Captain to take them out into the Mediterranean, she thought they would have a light lunch at one, then perhaps do a little fishing. Karen and Caroline returned to their sun loungers and invited Tim to join them. They all lay down and relaxed, the conversation was sporadic and light. He began to like Caroline, she had a wicked sense of humour, very dry and unexpectedly sophisticated. Tim was feeling horny, he wondered if he should ask Karen's permission before doing anything for her friend. Tim decided that he would if there was an appropriate moment, but felt that Karen would not have brought Caroline along unless she knew his profession and wanted to share his favours.

After an hour Karen asked Tim to get a cold bottle of Chardonnay. She explained that the cellar was the second door on the left as one entered the boat. Tim heaved himself up. He had an urge to explore the yacht but thought that there was be ample time for this over the next two days.

Tim entered the room and fumbled for the light switch, as he did a black bag was thrust over his head and his arms were grabbed and handcuffed behind his back. Instinctively he fought but his assailants were well prepared and he was quickly overpowered. Seconds after being subdued he realised he was probably lucky that none of his wild punches had made contact. His assailants were probably the Captain and one of the crew members. Tim didn't like the idea of sitting down to dinner with the Captain sporting a huge black eye. Karen or Carline clearly wanted to have a 'kidnap' scene.

One of Tim's assailants then untied his bikini leaving him naked. Tim never liked menials seeing him naked, he felt that being a whore, especially at Cartwright & Palmer, was hugely more demanding than serving drinks on some boat. He should be shown the proper respect. This said, if this was what Karen wanted he couldn't complain. He put up a few more token struggles as he was led down the corridor, in case Karen or Caroline were watching. Tim got to what he took to be the state room and was told to kneel, this he did. He was now rather looking forward to having Karen and Caroline, this was going to be a kinky weekend. Tim felt himself gradually getting erect in anticipation.

Tim heard someone enter the room, it sounded as if it was more than one person, but he could not be sure. Tim's hood was suddenly removed, initially he was blinded by the bright light. As soon as he eyes focused, he saw it was not Karen and Caroline in front of him, it was Mr Tolbukhin, his old boss from the Commercial Bank of Chelyabinsk from who he had defrauded of some $20 million, flanked by two shaven headed gentlemen toying with conspicuously large rubber truncheons.

Tim was now coward but now he was truly scared. He was literally petrified, he felt as if his insides were turning to liquid as if he had been instantaneously struck down with Ebola. He couldn't believe that they had tracked him down. He felt the intense fear of the impending physical pain, along with the acute disappointment that his life had come to this...

~

Cartwright & Palmer started an investigation when Tim did not return, but it made little progress. They found that there was no record of a thirty foot yacht called 'Lady Isabel' and that Karen Maxwell was really a 55 year old secretary from Galashiels who was a little surprised to find thousands of pounds charged to her credit card for 'intimate services'. Their investigators confirmed the real Karen Maxwell had spent the previous week tending to her sick maiden aunt in Morpeth. 

Jessica waited in vain for news of Tim, only hearing the distressing gossip that went around the sex industry. Rumours abounded about his fate. The most persistent story was that he was taken to one of CBC's large factory complexes outside Ryazan, where he became a 'barrack room whore'. People came back from Ryazan saying they had met someone who knew of Tim or an 'English whore' who seemed to bare an unusual physical resemblance to him. None of the British CBC staff could ever verify these stories first hand. 

The regime was said to be extremely harsh with lots of stick and no carrot. Tim was confined to the factory brothel, and wore a skimpy uniform with a thick, heavy steel collar that had been securely welded around his neck. It had his name in Cyrillic engraved on it, along with the word prostitute. He slept, washed and worked in his collar, it was part of his life. He was frequently told he would wear it until he died, by inference remaining a prostitute until then. 

There was no pretence that he was an 'escort' providing 'companionship', he was now simply providing sexual services like the cheapest of tarts. He was given a quota of sex acts to perform each week. In addition, he always had to be ready to satisfy the workers' personal fetishes however extreme. If he failed to meet his quota he was thrashed. To ensure Tim was well used, no charge was made for his services unlike the female prostitutes at the factory. Tim was no longer a highly paid whore fairly willingly providing submissive services, now his whole life revolved around the most basic of sex and more importantly avoiding pain. 

On the yacht Tim was beaten up, humiliated, whipped and sexually abused continually for nearly two weeks. The punishment was a thousand times worse than at Cartwright & Palmer and it seemed never ending. His tormentors did not ask for his submission they merely started out each day with the aim of causing Tim as much pain as they could without doing him permanent damage. He was a wreck by the time he reached Ryazan, all he could think about was how to avoid the next beating, he couldn't even think of resisting CBC's demands.