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.