A Ladyboy Syndrome. FINAL

SO FAR: Young student lawyer Jack falls for a ladyboy during a short 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. He has used his resources to have introduced Jack to cross-dressing with view to full feminisation? His worldly-wise stooge, Denny, is to accompany Jack on a three-day luxury break in London.

A shiny black Mercedes limousine pulled up outside Jack's building. He, (or should it be she?) was waiting anxiously in the lobby and her eyes twinkled at the sight of her carriage arriving. She felt good, really good, and ready for what the weekend was about to deliver.

Wolf whistles seemed to have gone out of vogue, but on seeing his date. Denny was sorely tempted. Jacqui was wearing a maroon two-piece with a frilly white blouse underneath, sheer silk stockings and red patent middy-heels. The skirt was tight requiring careful negotiation as she slid into the back seat of the limo. As she sat beside him, Denny's eyes were bright as he seemed not to know what to do with his hands. He wanted to caress her, grope her, run his hand up her skirt and along her thighs, all at once.

Jacqui could read all of that and her mind was moving in the same direction. Her penis was complaining bitterly, constrained in its tight, cotton prison. What she felt the urge to do was unzip Denny's fly and encase her pink painted lips round Denny's familiar prick.

The chauffeur was no slouch. He read the mood music very clearly and he did not want any staining on his leather seats. By asking some questions about their proposed route he managed to inject some sobriety in his passengers. Happily for him they settled for just holding hands for the relative short journey to the posh Invictus Hotel in Central London.

Jacqui scuttled up to their room whist Denny completed the formalities at the Reception Desk. It was not so much a room as a suite. Luke Dangerfield had spared little expense it seemed. There was just time to refresh her lipstick and add a spray of perfume when the door opened and in strode Denny with a flunky carrying their suitcases following close behind. Denny was so keen to grapple with Jacqui that he would have forgotten to have tipped the bag carrier had the man not stood his ground and coughed in classic style.

Denny had his tongue down Jacqui's throat in seconds and she could feel his hard prick rubbing against her belly. It was certainly delivering a message and one that Jacqui was over-eager to receive. She abandoned her mouth to his tongue and sought the button and zipper that would set his monster loose. His trousers fell, underpants too, and Jacqui disengaged her mouth from his, swapping it for Denny's prick as she slithered down and onto her knees. At that moment that seemed to be the best cock that Jacqui had ever had the opportunity of an intimate association.

She sucked with absolute gusto forgetting the obvious consequences, and deaf to any exhortations Danny might have been uttering. It was so big and fat, and long and hard, and she had it to the back of her throat, deeper than she had ever cock-sucked before. How could she be surprised when the thing started shooting sperm?

She felt a mixture of delight and disappointment as she swallowed the gift of Denny's jism. The degradation of slurping up another man's sperm was an exquisite feeling, nothing like any other. But it was too soon. Jackie wanted much more sex play than just that. She sucked out every bit of sperm from the prick's slit even as the blood pressure inside started to drop.

But Denny was still fired up. He clamped his lips on Jacqui's and his tongue searched for a taste of his own cum readily available in her mouth. Meanwhile his hands had her skirt undone, down and the two sets of knickers and pantyhose followed on. Only then did he disengage mouths and fall to his knees. Jacqui's prick disappeared into his mouth in its entirety at first. She let out a squeak of pure pleasure.

She stamped off the underwear round her ankles and then enjoyed the luxury of opening he legs as wide as she desired. All of this time was Denny dutifully performing fellato and grunting like a pedigree porker. Jacqui sprayed - it was inevitable - and Denny slurped up his reward greedily. This was sex in its rawest form.

Unsurprisingly, once their heart rates had returned to near normal, they wordlessly headed for the big double bed and, spunk soiled as they were, they lay on their backs and promptly fell asleep.

An hour or so later Denny woke Jacqui with a glass of champagne in his hand, "How romantic," Jacqui thought, collecting herself together in readiness to take the glass. But the illusion was shattered when Denny steadily drunk the whole of it right in front of her.

"Oh, sorry," Denny said when he realised his faux pas, but he made it even worse saying, "the bottle's next to the settee". In other words, "get you own".

"No sex for you tonight, Denny," did Jacqui's brain say to her penis.

Nor the following morning either, it turned out. Denny had drunk too much red wine over dinner followed by cognac afterwards. That was put down to the fact that they had a benefactor picking up the tab. If Jacqui had wanted an early morning fuck she would have been disappointed - but she didn't want one anyway - at least not with Denny.

Jacqui's black cab dropped her off near the Tian Tian Japanese Supermarket in Ealing. The cabbie helpfully indicated the route she needed to take to find the Thai Massage Studios. Indeed, the entrance did not advertise itself overtly and could easily have been missed.

Jacqui was proud of her legs and she wore a short skirt and sheer tights and middy heels to show them off. A couple of handy windows allowed her to check her reflection out as she passed them by. She felt good - she felt like a real woman. What a change from that young, innocent lad who had joined the football crowd for that short beano in Pattaya, Thailand

Somewhat incongruously the entrance to the Thai Massage Studio reminded Jacqui of similar premises she had seen in Walking Street in Pattaya and, as she entered, there was a familiar smell too. A pretty Thai girl, Jacqui presumed, shimmied round from behind a desk and greeted her with a warm smile and a slight bow.

Jacqui introduced herself. "We are expecting you Jacqui. My name is Maddy. Please follow me."

"The name Maddy - that's a new one on me," wondered Jacqui, keen to start some sort of relationship with the girl.

"In Thai my name is spelt M-A-A-D-A-I and so Maddy is pretty close. I will introduce you to out Masseuse Erica. She will give you a wonderful time and will offer you ANY service you require."

Erica's face was beautifully made up under her jet black hair. As Jacqui was not very tall Erica was taller and, as far as Jacqui could tell, she owned an hour glass figure under the smock she was wearing. She took Jacqui's handbag from her and allowed her client to see it put in a safe place. Jacqui slipped out of her shoes as Erica unzipped her skirt and helped her guest step out of it. Then off came the jacket followed by Jacqui's cotton shirt.

Erica knelt on the floor and with both hands she rolled down Jacqui's tights, her head close to the disguised bulge of Jacqui's testicles. French knickers in the outside helped hide a pair of severe elastic panties aimed at keeping Jacqui's prick in check, whatever state it was in. And, right at that moment, it was rapidly filling with blood. Erica slipped off the Frenchies but left the other pair alone for the moment.

Erica made a move for Jacqui's waist length camisole and that came off easily enough but the undressing stopped at Jacqui's bra. Erica looked at her client quizzically as if asking permission to progress further. The brassiere, more than anything, was the bastion of femininity. Remove that, expose the male chest, and all illusions disappear. That hesitation, and that realisation, hit Jacqui hard between the eyes.

Erica seemed to understand and effectively changed the direction of their unspoken conversation and helped her client mount the massage table and to lay on her front. Then she discretely pulled down and off the restraining panties making Jacqui naked except for her bra. It was just as well Erica used her guile and professionalism as Jacqui was entertaining a poker-stiff erection.

Erica settled down to the business she was trained to do and gave her client a quality massage that was both cathartic and erotic. She unhooked Jacqui's bra in order to be able to sweep the full length of her body. Before turning her client Erica concentrated on Jacqui's anus. pummelling, squeezing and then teasing the entrance with her deft fingers to the point that her client was raising her hips to encourage Erica to venture further.

Erica, for her part, recognised the tell-tale signs that Jacqui had very recently been fucked in that there were traces of dried male sperm on the sphincter's edge, And Erica's finger could push in with minimum resistance indicating, perhaps. its recent surrender. Of course, then turning Jacqui onto her back had the expected result. Her prick, as hard as iron, stood straight up almost as if it was daring Erica to engage with it.

Erica's eyes met Jacqui's. Jacqui's eyes pleaded. Erica dropped her head and allowed her mouth to envelope the purple head of Jacqui's prick. Jacqui let out an involuntary squeal of delight. Electricity shot straight up her spine to her brain in a continuous flow. And the voltage increased as Erica slowly moved her head up and down whist sucking strongly.

Jacqui squirmed and squirmed. Her total concentration was on the mouth and the teeth that were assaulting her penis giving her the most intense pleasure imaginable. Her mind, her whole being, was concentrated on her seven inches of muscle that Erica was performing on. Nothing else in the world mattered to her in those seconds turning into minutes.

Erica, in total control, knowing exactly what she was doing and the reasons for doing it, kept Jacqui on the edge for as long as she thought necessary. Treating Jacqui almost as if she were her ward, Erica chose the right moment to release her into a huge, all-enveloping orgasm.

Erica gobbled up the cum that spurted into her mouth. Aware that her client had ejaculated the evening before, or even perhaps that very morning, Erica was cautious about how much she swallowed. Her plan was to squirt and goodly amount into Jacqui's mouth before the last sensations of her climax had abated.

Erica was spot-on with her timing and the sensation of having her gob filled with her own spunk sent a shiver of lust to chase all the other sensations she had experienced at Erica's doing. But that was not the end by a long stretch.

Erica divested herself of her clothes in one sweep and stood up naked, bending her back in a prolonged stretch. Her prick, all eight inches, stood straight out, rampant. She lowered the massage table adroitly and placed Jacqui, still half comatose, across the end. Almost by slight of penis she had hers in Jacqui's anal passage, right to the hilt.

Jacqui squealed. Whether in surprise, pain or pleasure Erica did not care. These were her instructions, and for a successful completion she had been promised a handsome bonus.

Erica had been charged to prolong the experience as long as possible. She started fucking Jacqui gently with small strokes although with her prick buried deep inside her. She had Jacqui pinioned, and totally at Erica's mercy.

Once she had recovered from the surprise and shock of the assault on her, Jacqui felt mostly pain at first. The realisation she was in a sort of rape syndrome started to win-out and perversely, pleasure started to flood in. If she had been a real woman rape would almost certainly be horrific in all its forms, but she wasn't a real woman was she? She was a man in a woman's guise and was starting to enjoy the scenario she was experiencing.

As Erica's strokes slowly lengthened Jacqui made them more by meeting his thrusts and extending his withdrawals. In no time they were shagging like a couple of wild beasts and making the associated grunting and puffing. Erica knew all the tricks of self control and he kept shagging Jacqui for a good length of time, but eventually the build up of pressure from his spunk defeated him and he shot loads and loads into Jacqui's gaping cunt.

Looking back, Jacqui was to describe that session with Erica as "fabulous" except for one small thing. At the end, when they were both lying exhausted, with spunk dripping avidly from Jacqui's tortured arsehole, she found that, during the cut and thrust of it all, her bra had slipped round and then down to encircle her stomach. How pathetic did that look? And similarly did her flat, naked chest.

Erica was a ladyboy. He wasn't Thai; he was born in Sunderland, an industrial city in the North of England famous for breeding men of steel. But a surprising number of genuine Thai ladyboys had drifted to London and a few other cities as the financial pickings were easier and the competition less than in Thailand. And, of course, there were ladyboys of other nationalities too.

Maddy came and rescued Jacqui from the floor of the massage room, and she did not turn a hair witnessing the state that Jacqui was in. She gave her one of those lovely Thai smiles with such genuine brown eyes, that would have melted away any embarrassment that Jacqui might have felt.

She let Jacqui to a shower room bedecked with exotic tiles and shamelessly washed her charge thoroughly. She soaped her hands and used them all around Jacqui's penis and scrotum and paid especial deference to her anus - still leaking Erica's semen. It all seemed the most natural thing in the world.

The vegan burger bun and mug of tea that followed seemed a bit incongruous in such a Thai setting, but Jacqui was hungry and Maddy had a message to deliver.

"You would look lovely with breasts, Jacqui. And perhaps a little work on your bottom and hips. You'd make the perfect ladyboy. You would make your master so proud."

"Your master?" Jacqui turned on her.

"I'm sorry," Maddy looked genuinely upset and he body retreated into itself. "I didn't know what to call him. What he is to you."

"Who is this man?" Jacqui demanded, admiring her shapely legs as she did so. They looked so good in sheer nylon.

"I don't know his name. Really I don't Jacqui. He said he wants you to have breast transplants and other bits." Maddy's beautiful eyes were downcast and she seemed genuinely sorry for having upset her guest.

"And he said he would pay for it?"

"He is very rich, I think. He wants you to go to a clinic in Thailand. He wants you to be a genuine ladyboy."

With those words very much in the forefront of her mind, Jacqui hailed a taxi in a busy street not far away from the Studio.

"So what have you been up to this morning, sweetheart?" asked Denny cheerfully when they joined up together that afternoon.

"I had a Thai massage," said Jacqui noncommittally. How about you Denny?"

"Three hours in the Science Museum? Actually it was quite interesting. But I couldn't keep my mind on the exhibits. I kept thinking we have a free afternoon together and I want to fuck your pretty little arse."

"That's not going to happen Denny. I'm afraid I'm not in the mood," said Jacqui flatly.

"You what?" shot out Denny.

"Don't make a scene Denny. Perhaps after we return from the theatre tonight."

"Perhaps," howled Denny in his best imitation of being a male chauvinist.

"I am not your property Denny. Do I have to remind you of that?"

""But I was ordered to fuck you up-hill-and-down-dale."

"That's an old-fashioned expression Denny. What brought that on?"

"Come on, upstairs now, I insist."

"Insist all you like Denny. I am not in the mood," Jacqui said firmly.

"Why not? Tell me why not," demanded Denny in nothing short of a sneer.

"Because I have already been well fucked this morning and I still have his spunk dripping out of my arse," said Jacqui cruelly.

Denny looked at her aghast. That was not supposed to happen. that wasn't in the script. "Are you making that up?" he faltered.

"Nope. I'll take my panties off if you like and show you the wet stains. It was a set up. It was planned this way."

"It was planned that you got fucked this morning?"

"Yes, Denny."

"Fuck it. I'm getting out of here," he said unchivalrously.

Denny did just that. Jacqui never saw him again that weekend. She dined in the hotel and used one of the theatre tickets and took a taxi to watch the show. After breakfast on Sunday morning she took a taxi back home, a day earlier than expected, and became Jack again.

It was if everything was back to normal. Except it was hardly normal before. Jack's life was sort of being pulled in different directions and he had jumped from one to another, and back again. Like before, he resolved to be male and never dress again - but he did not go so far as to destroy the lovely range of female clothes that he had inherited in one way or another.

Luke left him alone entirely and at one point Jack thought he was for the chop - work wise. But no, he seemed to still have Luke's confidence in him as a tutee if nothing else. Besides, Jack had no absolute proof it was Luke's hand, or rather Luke's wallet, behind the appointment with the Thai Massage Studio. Mind you, he couldn't think who else it could have been.

Any male that has seriously cross-dressed will know that it is addictive. If it is not in one's blood already, say from childhood dressing up in mother's clothes, then the propensity to do so can so easily be triggered by all manner of apparently innocent experiences. And once in the blood...... And it certainly was in Jack's blood. Ask Jack in a reflective mood and he would probably say that he caught the infection in Pattaya. Maybe so, maybe it was already there in him.

Jack's tutelage required him to undertake legal work on a day to day basis, but also to pass exams set yearly. Jack passed the first year's papers but, in Luke Dangerfield's words, Jack's performance was "very shaky". Luke was sympathetic and he offered Jack an evening of private tuition every week with a semi-retired barrister called Edward (Teddy) Strides. jack was immediately to find out Teddy was gay and extrovertly so. He was also very shrewd and in no time at all he reckoned to have the measure of "young Jack".

Wednesday evening tuition sessions were structured so that for the first hour Teddy would discuss "precedence", past legal cases that had a current standing in law. Then they would have half an hour general chit-chat over coffee, followed by an hour on particular subjects chosen by Teddy, on a week by week basis.

On the third week, in the half hour coffee break, Teddy suddenly undid his fly and out popped his penis more than half erect. "Get along and suck it, dear boy," the old queer suggested. "On you knees now."

Teddy was always dressed in a very smart pin-striped suit and waistcoat, with an old fashioned silver chain and waistcoat watch. He was also perfumed -up to the hilt and Jack imagined his personal hygiene was very important to him. So there was nothing really obnoxious about Teddy other than perhaps his age and his portliness.

Jack glanced down at the proffered prick. It was fat and sort of juicy, and it had obviously been places. How did the old bastard know that Jack was a possible candidate for giving blow jobs? Had Luke given him that impression? There was little reason to be sure that he had. Or did the old man try it on with virtually every young man who crossed his path? Anyway, a decision was needed and fast. It wasn't as though he hadn't had sex with an old man before, remembering the party he had been to with Andy, Bernie, being the guy in question. Jack found himself dropping to his knees.