A Ladyboy Syndrome Ch. 05

A Ladyboy Syndrome Ch. 05

SO FAR. Young student lawyer Jack, falls for a ladyboy during a visit to Thailand. On his return he is offered a tutelage in a legal chambers headed by gay barrister Luke Dangerfield. Luke has apparently taken a clandestine interest in Jack and had been using his resources to have the young man cross dress - and maybe be fully feminised? His stooge, Denny, is doing Luke's dirty work for him under the guise of befriending young Jack.

Come Saturday Denny turned up at ten o'clock sharp, just as he said he would. He looked Jack up and down and said, "that won't do. You need to change and quickly else we shall be late."

As it was Jack had spent an uncomfortable two days since he had last seen Denny, wondering if he wanted to pursue their relationship any further. It was not so much about having a gay relationship with him, but rather did he want a subservient role to Denny. Did he want to be the bottom to Denny's top; roles that Denny placed great importance on.

And here, come Saturday morning, was Denny coming straight at him and ordering him about again. "What's wrong with what I am wearing?" Jack asked stoutly.

"Too masculine," Denny responded abruptly.

"Come again?" said Jack, his dander rising.

"Look, we're a couple right? When other people see us they need to know who is the male in the relationship and who is the female."

"You want me to wear a fucking skirt? Is that what you are saying?"

"No, no, Just a more feminine shirt and trousers, not jeans so tight they can see the bulge of your bollocks from half a mile away."

"Oh." Jack could understand his logic even if he did not entirely agree with the process. "I'll go and change."

"Quickly then."

Did Jack like being bossed about? The answer would usually have been a firm "NO". But there is something a bit sexy in being dominated, isn't there? Especially if it carries on into the bedroom?

It carried on into the depilation clinic. The receptionist very quickly recognised them as a couple and whom was the dominant partner. Denny discussed the nature of the intended treatment just out of Jack's earshot, giving Jack leave to just acquiesce.

"The nice lady here says your procedures will take about three hours. I'll be back at one-thirty on the dot. You can depend on that, Jack. I'll take you to lunch afterwards. O.K.?"

What could Jack do other than agree? Running out of the clinic door may have been an option, but did he really want to? Instead he rendered himself naked just as he was instructed to do.

"What sort of music do you like?" asked the clinician. "We are going to put some headphones on you and a mask for your eyes."

Jack chose audio stories about Rumpole of the Bailey instead. He was studying to be a lawyer after all. Three episodes over three hours passed in no time with Jack intent on the stories at the expense of what was being dome to his body. In fact, to his annoyance, he was deprived of the last eight minutes of the third story. The clinician told him he could take the tape home with him and listen to the ending at his leisure.

Jack was hauled into a sitting position and handed a mirror whereby he could observe the changes to his body. He had already shaved his pubic area, so little change there apart for his pubes being very much more smoother. His chest hair had disappeared - no big deal about that. They had been straggly tundra rather than a verdant forest.

"You'll never need to shave your face again," said the female clinician helpfully. " And then there's armpits and other little bits. Your head hair and eyebrows are saved. We have a nice range of wigs if you want us to go further?" added the woman a little facetiously for Jack's liking.

An element of doubt caused Jack to frown, but the deed had been done. No room for lamentation. When he was handed his clothes neatly folded into a wicker basket, he half expected they may had been swapped for the girlie variety. There was a tickle of disappointment when he found that the genie had been asleep.

"Who paid for all that and why?" asked Jack of Denny as they sat in a burger bar later that afternoon.

"You have a benefactor and I am not at liberty to say who that is," said Denny, avoiding looking Jack in the eyes. "If you have a problem with that you should have asked the question before thwe procedure and not after."

"What does this so-called benefactor want of me? You must know."

"I expect his motives are lascivious. The legal profession is full of sexual predators of one kind or another. Haven't you worked that out for yourself?"

"You're joking?"

"Taking you for an example Jack, you're only on the first rung of the legal ladder and already you're bent."

Those words pulled Jack up sharply. He felt himself blushing. In all honesty he couldn't really deny that being the case. Why did his prick suddenly start taking an interest? Was the thought of being bent cause for arousal? Jack tidied the question away and asked one of a more mundane nature. "What are we going to do now Denny? I should be playing football this afternoon."

"You've been dropped from the team Jack, remember? We're waiting here for a girl called Carol and she is going to take you shopping."

"Take me shopping? Shopping for what?"

"You need a wardrobe to show off your new body."

"You mean feminine clothes?"

"Go to the top of the class."

"And who's going to pay for them? No, don't tell me - this mysterious benefactor of mine?"

"Got it in one," Denny turned on Jack with a contorted face. "Don't look a gift horse in the mouth," he hissed. "Go with the flow. You really haven't got much choice, have you?"

The nature of the words and the way they were delivered Jack found intimidating. Life for him was getting more and more complicated. Was he in danger of losing control of his own destiny? He had sort of sleep walked into the clinic that morning. His logical self had said "don't do it". His libido had urged otherwise. Anyway, what was done, was done. The loss of body hair was no big deal anyway was it? Count how much he would save in shaving paraphernalia over the years to come.

"Hello boys. I'm sorry I'm a bit late." A chirpy girl with long blonde hair wearing a pink coat, and lipstick to match, plonked herself down on a chair between them. "You must be the Jack, the guy we are turning into Jacqueline?" she suggested brightly.

Those few words brought Jack completely down to earth.

Jack staggered through the door of his flat some three hours later. It took his taxi driver help him carry all the carrier bags up two the flights of stairs to his front door. Not that they were all for Jack; crafty Carol had also procured some clandestine items for herself on the same tab. The total spend was well into four figures.

Jack downed a bottle of red wine in record time. With all the goodies stacked up in a pile in the living room Jack virtually collapsed on his bed from fatigue and then fell asleep for a good two hours. He may have been there longer had it not been for a violent rattling coming from his front door.

"I've come to collect my share of the loot," announced a somewhat discomposed Carol. "Doesn't your fucking doorbell work? Oh my, what a good job they've done on you."

Jack had hurried to answer the doo careless of the fact he was wearing just his lacy panties. "Oh, I'm sorry..." he started to say.

"Ooh, don't be," said Carol, "I'm just in the mood for a smooch." Her eyes glinted their confirmation.

"Perhaps some other time," said Jack hurriedly. "I'm totally pooped."

"We could just lie together. I could hold you and you could suck on my nipples."

"Hold that thought," screamed Jack's libido, but his brain failed to catch up.

"Some other time perhaps," said Carol miffily as she gathered up her purchases. Don't leave it too long though," she added as she sailed through the front door.

"Damn, damn, damn," whispered Jack as he looked down at the tent in his white panties. Still, it seemed to prove that he could rapidly get the hots for a female as well as a male body. Or was it just the thought of sucking on Carol's teats just as he had had his mothers'.

Jack's mind was still somewhere in No Man's Land when his mobile summoned his attention. He saw it was Danny, but he accepted the call nevertheless.

"I'll be round in an hour. Make sure you're showered and dressed for me Babe."

"No Denny. Not tonight," replied Jack flatly. No amount of cajoling would make him change his mind. If Denny had come and banged on his door Jack was determined he would not let him in.

There were to many clandestine things going on. Who was this man in the shadows who had paid for Jack to be depilated and had spent a fortune on clothing and accessories? Jack was being manipulated and that was not good for Jack. He knew he should have put an end to it earlier, much earlier, but better then than later. Let this distant admirer, or whatever he is, come out of the dark and show himself. Or herself?

Jack showered before turning into bed at his normal time close to midnight. Before doing so he rummaged through the bags on his living room floor and pulled out a full length silky nightie and a bottle of quite expensive perfume. Having treated his body to both he snuggled up in bed close to a state of contentment.

Denny was at him on the morrow, first in person at the door and, failing that, on the phone. "I'm not playing to your rules Denny and those of whoever is backing you. I may be a bottom, as you describe me, but I don't want to be your bottom, or your receiver, horrible terms, under any circumstances. Not unless you tell me who is pulling your levers and is trying to turn me into goodness knows what.

"I can't tell you who is mentoring you Jack. It is more than my freedom's worth. But he is rich and powerful and he wants all the best possible for you. Trust me."

"And he wants to feminise me? That's what you call his wanting the best for me is it?"

"Is that so bad Jack? He's very kind and very generous. Besides, you like being a girlie don't you. You like dressing and you like cocksucking and you like....."

"I though I did," Jack interrupted feeling his face begin to glow red.

"You're talking to me, Denny. I know exactly what turns you on, Jack."

"I'm trying to put that behind me, Denny."

"Since when?"

"Since today."

"So why did you stay at the clinic and have the treatment I arranged for you?"

"It was just a lapse Denny. You took me by surprise. But that is it. Now, kindly leave me alone if you won't tell me the name of the person who is pulling your strings."

Danny tried a few more times to repair his relationship with Jack. but to no avail. It was probably no coincidence that he was given a new legal assignment in another town relieving Jack from having to contend with him.

Prior to his re-assignment Denny had a meeting in a small office in the bowels of the Inns of Court. He was summoned there by Luke Dangerfield no less.

"So what went wrong Denny. He went to the depilation clinic like a lamb so you say. I thought the rest would be plain sailing. Was it something you said to him?"

Denny looked shocked. "Oh no, sir, not at all. I can assure you I played my part exactly as you instructed me to. To be honest with you sir, not wishing to get her into trouble, I think it was something your niece Carol said to him."

"What did she say?"

"She sort of made fun of him and said he was being turned into Jaqueline. It was nothing really, but it just didn't go down too well."

"They still spent a fortune together at my expense?"

"What can I say to that? That was entirely down to Carol."

"Yes, O.K. Denny. I suppose you did your best. I am sending you off to our Edinburgh office for a while. There's plenty of men wearing kilts up there and, traditionally, they should not be wearing anything underneath. You should have a gay old time."

"You don't want me to.....?"

"No thanks, I can't spare the time."

With disappointment registered on Denny's face, he left the room. There was nothing he would have liked more than to have received a re-assuring dump of his master's cum.

Jack's new resolve lasted, of sorts, for the best part of a month, but in the fourth week he was wearing some manner of female silky apparel in bed every night. He had also had, spread out, five sessions with the cosmetics and the same number of dressing in full. At the very least, one could say, that his resolve was very shaky.

The fact that he had a mysterious mentor weighed heavily on his mind throughout the month. How dare somebody completely unknown to him connive with others to reshape his sexuality? He imagined his bile rising. But at other times, most time, thoughts of a force intent on feminising him and having power over him, sent the necessary electricity to his scrotum for his sexual interest to start up again. Well, that was O.K. He wasn't in any way signing up to celibacy.

Jack noticed an interesting quirk in this month in a form of limbo. If he masturbated helped by film or photographs, these would be feminine based. If he tossed himself off using his imagination alone, it was always man on man. Where did that leave him? he wondered.

One bottle of red wine drunk and a second decorked, and Jack faced defeat at last. He texted Denny. Asking an how he was - an arbitrary question of course, designed to explore the possibility of the recharging of their relationship. He was aware that Denny had comeback from purdah in Edinburgh. Sent by a tipsy man feeling randy, Denny read the situation accurately.

Denny did not react. He did report Jack's message to Luke Dangerfield at the first opportunity. "Leave this to me," said Luke, his face giving nothing away.

Later Jack was called into see Luke in his chamber. It was done in such a way that team members usually expected to get a wigging for some misadventure they have had. Not so, Luke's severe face burst into a welcoming smile as Jack negotiated the chair he had been invited to sit on.

"I have been very pleased with your commitment to your work here in my chambers, Jack. Several of the senior staff have brought your name to my attention. It has also been suggested to me that, whilst you have worked hard, you haven't seemingly played hard. So I think a short break is called for."

"Well, thank you sir," said Jack genuinely pleased that his efforts had been recognised.

"I understand that you and Denny are close friends and that you tried to contact him a couple of days ago?"

Jack hesitated. This was not the time to explain his misgivings about Denny. "Yes, sir?"

Luke handed Jack an envelope. "In there are reservations for a weekend stay in a top class Central London hotel. All meals paid for, drinks and use of all the hotel's facilities. Additional there are tickets to a West End show and, what I especially want you to enjoy and describe to me afterwards, half a day at a body tuning clinic."

Jack was close to being flabbergasted. This was totally out of the blue and, in his modest opinion, not particularly warranted. True, he had worked diligently during his time in Luke's chambers, but he had hardly been given the opportunity make a big splash of sort - not enough to deserve this star treatment. Somebody, not quite as naïve as Jack might have suspected that this happening was too good to be true - that there was probably some sort of catch somewhere. He would find out very soon if there was.

"Oh, and by the way, Jack, I thought you might appreciate some company. The tickets are for two persons. Denny has assured me that he would be delighted to accompany you. I know how well you two get on together. have fun."

"Oh fuck," said Jack, very much under his breath. He said the same when he arrived back at his flat, and again as he stood under the shower. "When he heard a summons from his front door he said "double fuck".

Denny was buoyant. His blue eyes seemed bluer than ever and they were twinkling too, With his blonde hair and lightly tanned skin he was one very good looking young man, to be sure. Any girl in her right mind would throw her knickers at him if he appeared on a stage. And there he was, obviously very excited at the thought of sharing a weekend with Jack - and there was a good reason for why, coming up.

"You'll be able to wear all your new clothes," Denny beamed.

"You what?" said Jack enquiringly.

"It was for this sort of thing that that Luke had Carol buy you a wardrobe of fem clothes."

"Luke bought them?" Jack gasped.

"Well, who do you think?"

"You're not enjoying his patronage for nothing Jack. Surely you've sussed that out?"

"Well no, not really," whispered Jack, now very much on the defensive.

"He knows everything there is to know about you Jack. He knows you better than your mother does. He's been grooming you since that first day you walked into his chambers. And you are a very lucky - err - young man that he has taken a fancy to you. He can open all the doors in the Old Bailey for you. You'll find yourself walking in Rumbold's footsteps."

"But, what's the price I'm going to have to pay?"

"Not a price at all is you lay back and let things roll over you. If you resist it will be a short road - and you'll be dumped and blacklisted."

What does he want from me?"

"You don't need me to tell you that. In the meantime he wants us to stay in the West End as boy and girl and enjoy a romantic time together as lovers"

"A romantic time together?"

"Check the hotel reservation. It's for one luxury room with one very big bed. You are to be my girlfriend for the weekend Jaqueline. Luke wants me to fuck your arse ready for him to take over. You might say I am his asshole buster.

Being called Jacqueline caused a surge of mixed lust and excitement in Jack's body. The fact that he had been given no choice about the arrangement for the weekend ahead, it was a fait accompli, sort of absolved Jack from any guilt, and he found himself looking forward and becoming excited about his forthcoming full feminine role. And the fact that it would be for a continuous three days too. What was more, he could rely on Denny to ensure he gets well and truly fucked.

TO BE CONTINUED