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.