Tim Ch. 03

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 reveal Tim's true sex after some of his friends had accepted a blow job. But now he wasn't so sure, Woody wouldn't shut up about how good Tim was and that bore Berneville-Claye said it was the best blow job he had ever had. Looking at Tim he 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 a boy.

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 knew he could not very well refuse. He had made it plain to Sally that he proposed to have Tim himself later on in the weekend.

Sally led Tim over to the bed. Conscious of 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 erect. 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 blow job. 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 blow job 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 mouth. If he was going to give a man a blow job 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."

"Yes Master. We whores may have many faults but I can absolutely assure you we do not gossip."

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 did as he was told. He 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 f***ing 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 wanted to take Tim, 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 dressed Tim in bright yellow satin knickers and a matching corset. As before, she took huge trouble with Tim's makeup. She decided that he would wear a short light summer print dress, so light in fact that it was almost transparent. 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.

Tim curtseyed when he presented himself at Freeman's suite. "Tim, God you look great. 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 taking you properly. So my little slut, drop your knickers and bend over that table."

Tim did as he was told, lowering his knickers, pulling his dress up to his midriff 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 massaged Tim's wonderfully smooth buttocks and gradually spread them. Freeman rubbed his penis between Tim's buttocks, 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 blow job. It seems that this is all you are good for, my little slut, 'sucking and fucking'." Tim knelt knickers 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 in Miss D'Alquen's room, dressed in a short silk kimono, when Sally entered the room.

"Tim, Jane, how goes? Will you be ready for 2 o'clock?"

Miss D'Alquen answered for both of them, "Yes he'll be there."

"Ben said he asked for Tim, or should I say Lucy, to be dressed in a black latex dress, any problems?"

"No, it 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 was going to squeeze in, the waist was tiny.

"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 sat and chatted to Jane as Tim went to the bath room and put on his knickers, suspenders, stockings, stilettos and a shiny PVC corset.

"You wouldn't believe how excited Ben got when he found out that Tim was working here. I am sure he has fancied Tim 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 returned in his underwear, Miss D'Alquen started her artwork. Sally had left by the time it came to squeezing into the dress. Somehow Tim got it on. The last thing was to attach his 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.

Freeman found the lunch purgatory, all he could think about was Tim. Tim had been right he had wanted to do this for years. Now he had him in his power, Freeman was almost dieing 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.

When Tim got to the dungeon, he 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 still the place 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 skirt fell forward revealing his knickers and suspenders.

"Lucy, stand up."

Freeman circled around, looking at his possession. To think he could buy Tim for few minutes of his income. Freeman lifted Tim's skirt staring at Tim's 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 knickers and played with Tim's arse. Tim was well lubricated, and 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 in to Tim's panties 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.