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.