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).