A Ladyboy Syndrome

A trip to Pattaya in Thailand was as good a destination as anywhere. Jack desperately needed a break, a holiday.

He did not even like Eugene Trent whose stag do it was. Sure, they both played for the same amateur football club and a whole crowd of them got pissed together on a Saturday night, but that was it.

Jack was seen to be a bit of a loner. What he actually was, was lacking in self confidence. He was slighter than most of the lads in stature and he just led a sheltered childhood. Being the only boy in the family with four sisters and a doting mother he had rather lost out of some of the rumble-tumble of childhood.

At five foot nine and light in weight he as fast on his feet, an ideal winger in the football team and with a healthy goal score to his name. Instead of going to university like many of his school mates he chose to be articled to a law firm - the first steps on the road to being a barrister. His mind was as nimble as were his feet.

That choice meant that he spent a couple of years largely confined to the Inns of Court and assisting his qualified colleagues in the law courts themselves. Joining the Supporters Club of Pathway United F.C. was very much Jack's main social life.

For a young man with four sisters it might be expected that he was at ease with female company and would socialise accordingly. Unfortunately that was not the case. He could give no plausible explanation as to why that should be. Rather than address the problem, Jack chose to ignore it.

Although he tended to avoid the Supporter's Club's more raunchy activities, one of the lads injured his ankle and was forced to drop out of the stag party. Jack almost literally had his arm twisted to fill the last minute vacancy. Quinton Hurst K.C., Jack's mentor at his place of work, slapped him on the back and said, "you must go, dear boy. Too much work and no play makes Jack a dull boy, eh?" quoting the old proverb verbatim and congratulating himself on his adroitness. To give the old buffer his due he handed Jack ten thousand bahts on his last day and told him to "get laid, my boy".

Jack needed no encouragement in that regard. According to the lads at the football club, not that they knew it, Jack was the only virgin amongst them. Eugene Trent had stood out particularly for his boasting of conquests far and wide. There must have been a soupcon of truth in them at least as the word on the block was that Eugene's bride-to-be was already "in the club", as it were.

And it wasn't enough for Eugene to settle for a stag weekend in Budapest or even in one of the fleshpots of liberal Germany. No, he asked of his coterie, a fourteen hour journey to Thailand, three nights and fourteen hours back - providing there were no hitches.

Jack was coming up to his nineteenth birthday and was the youngest of the revellers. At least half of the "dirty dozen" (Eugene's invention). were married men. (Actually, there were just ten in the party.)

The flight started jolly enough but the cabin crew wisely limited the dispensing of alcohol for very good reasons. The plane was full and a group of drunken revellers was the last thing the crew needed to contend with. The law book that Jack intended to read on the journey never left the overhead locker.

The first two nights in the hot spots of Pattaya were best described as a sequence of leery drunkenness during which Jack played his part and suffered the enduring hangover the next morning. On the third night he feigned a serious stomach upset, and once the coast was clear, set of into town on his own.

By this time he was on a mission. Jack was mesmerised by the ladyboys. So many of them were really beautiful, so sexy and so friendly. Before he had succumbed to alcohol on the previous two night he had found himself lusting over any number of them. H assumed that most of them were ladyboys and not "just" female prostitutes but, either way. he didn't really care. It was time. Time to lose his cherry. He had spent most of that day, as his hangover had slowly lifted, sorting out his mind. With London six thousand miles away he could risk his reputation by fucking a street girl or a ladyboy surely?

In the hotel's front of house there was employed a genial guy called Chai whose job it was to answer customer's questions and deal with any problems and complaints. Jack waited until he could catch him alone. "I want to experience a ladyboy Chai. Not just any old ladyboy but something special. Where do I go, please?"

"If you want a really special girl it will cost you more," warned Chai, fully aware as to how parsimonious Brits often were.

With the better part of Quinton's ten thousand bahts still intact the last thing Jack was worrying about was the cost of his new adventure. With that point covered Chai revealed an address and some directions. Jack, for his part, forgot to tip him.

The address was a lane off Walking Street, probably the main tourist thoroughfare in Pattaya. The street was already familiar to Jack as he had spent the previous two nights with the boys sussing out the dozens of bars along its length. Even if they had come across The Sleepy Python in its side street, it was not a place for just walking into. A robust door with a prominent bell was all the exterior offered.

An archetypal Madam of indeterminate age opened the door and weighed up the caller in one professional glance. "I've been recommended......"

"Please come in sir. You're welcome." She led Jack into a small anti-room equipped with a rudimentary bar and some bar stools. "Help yourself to a drink whilst I call the girls together."

A small CCTV camera in a corner of the ceiling made Jack shiver. The girls could get a preview of him before he would get to look at them. Jack went to pour himself a large measure of Thai whiskey but desisted at the last moment. He would likely need all his wits about him for what was to come next.

"Right," said the Madam in a business-like way as she returned. I will take you to see six of my girls for you to choose one. Have a good look and then come back here and tell me he colour of the chemise she is wearing. You need not choose in front of them. What shall we call you?"

That was a relief to Jack. He felt a little weak in the legs and was fearing that he would not be able to perform when the time came. Just what had he gotten himself into?

He stumbled into the adjoining room behind the dragon of a Madam. Sure enough, all six girls perked up as he entered and did their very best to showcase themselves. Jack was not to know that they had indeed previewed him via the CCTV, and the young virgin had indeed come across to the experienced girls as likely to be the young virgin he actually was.

To Jack all six were beautiful, sexy and desirable. Six pairs of eyes, seven including the Madam, were watching him with an air of expectancy that that made in careful scrutiny impossible. Jack went through the motions, smiling encouragingly, but was back in the waiting room absolutely no further forward. He chose blue for no other reason that it was the colour of the shorts he was wearing.

"Good choice," chortled Madam, that's our lovely Suzy.

Jack had the impression that if he had hosen any of the other five, their names would have been Suzy too. Madam held up a blue card so as it could be read by the CCTV camera. Nice one.

"We must do the business first Jack. What extras would you like?"

That interface was embarrassing as Jack was offered all manner of services, many of which he had no idea as to what they were. Of course, the girls were having to satisfy the tastes of customers from every corner of the globe and not just a fairly innocent boy from a middle-class English background. What, oh what was he letting himself in for?

Blue Suzy appeared at the door and gave Jack a ravishing smile that he felt would be hard to counterfeit. She led him away from Madam's clutches and along a corridor and up some stairs. They arrived at a room with an open shower and a massage table.

Shower first - obviously. Suzy undressed Jack slowly and methodically, carefully folding his shorts and shirt in a bench. She fell to her knees and removed the boy's trainers and socks. Then down came his underpants. Jack's prick had retreated inside of itself as much as it possibly could and much to its owner's embarrassment. Suzy just giggled a little and gave it a couple of playful tweaks, sharing eye contact with Jack as she did so.

Then she stood up and put both arms in the air expecting Jack to pull up and off her chemise. How sexy was that? She was a good six inches shorter than him which, as he was not tall, was a welcome bonus. Off came the chemise for Jack to find she was naked underneath.

Her breasts were small but perfectly formed and topped with pointy nipples. As her figure was slight they were probably in proportion to her body. Disconcertingly, down below her breasts was a small penis. Was that going to be a stumbling block for Jack?

The water seemed to turn on all by itself and was the cue for Suzi to start soaping Jack head downwards. Her small, soft hands caressed the boy's body as she spread the soap and then allowed the shower water to wash it away. She knelt when it came to Jacks genitals and her light, silky hands soon became hard to resist. Then she turned her man around and stated to work on his anus, first nudging his legs apart.

Suzy paid particular attention to Jacks arsehole, soaping his crack up and down and then letting her soapy fingers play with the hole and even to slip inside. Jack had not imagined anything like it ever, let lone actually experiencing what she was doing to him. His penis gave up being mardy and was soon as rampant as it could possibly. He heard Suzy chuckle as she pulled back the foreskin and massaged the head with soap.

The girl seemed to know precisely the limits to go before triggering Jack's climax. That was on the menu for later. She playfully pulled him out from under the shower and encouraged him to play with her breasts and torso as she dried him with a towel. She made him dry her similarly. All that time her little penis was sticking out, rock hard by all appearances.

Jack was fast losing his grip on the real world so caught up was he in the euphoria of sexual pleasure. The massage table was low and she draped Jack's body over one end and opened his legs wide. He felt cold ointment being spread and around his arsehole. Was she was going to bugger him, surely not?

Her little penis was not much thicker than a man's forefinger and it slipped inside Jack's arsehole as sweet as a nut. The feeling that racked Jack's body was incredible. The physical feeling was just great but the mental shock, disbelief, and the sheer feeling of debauchery was truly amazing. What was happening to him was beyond convention and totally mind blowing.

She stopped too soon. Far too soon for Jack's liking. She pulled Jack over to a small stool which she knelt on, her bare arse at the same height as Jack's prick with him standing behind her. It was all a carefully choreographed role play but it was brilliantly done. Jack was meant to posh his now raging prick, right into her sweet little anus. And that is exactly what he did.

It slid in so, so easily and the feeling was so, so good. Jack stood there as if transfixed, drinking in every iota of pleasure; animal pleasure, unbridled pleasure. The grunting he was making was communication to Suzy who, understanding, stayed in that position in order that her punter could enjoy the maximum benefit.

Eventually Jack started with slow strokes, hardly perceptible, the rising, then more urgently until he was shagging Suzy's man cunt in long controlled strokes. He wanted to delay his climax but was unable to. He had gone too far and, when it broke, it was like no other that he could remember.

Jack as done for. All he wanted to do was to lie still and slowly recover and relive all that had happened to him in that last half an hour. Suzy had other ideas,. She half dragged Jack over to the nearby bed and had her captor arranged half on and half off - his top half on the bed and him kneeling onto it. She pushed his knees further apart with her foot and entered the space in-between. She was obviously no novice with this particular manoeuvre.

All lined up she directed her rampant penis at Jack's anus and pushed it right in as far as it could go. Jack let out a roar of such a nature it was hard to tell if it were one of pain or sexual jubilation.

Maybe it was a measure of both. Suzy set about fucking him relentlessly and Jack heard himself egging her on. "Yes, yes, yes, Suzy, fuck me hard, harder." The boy imagined he felt her ejaculate in side of him and when her sperm started oozing out of his anus there was the proof positive.

Jack had been well and truly fucked and he was in a trance like state as he dressed and then was courteously shown out into the street by Madam. For some reason only known to himself Jack had refused the offer of a second shower. Consequently he wandered down Walking Street with Suzy's sperm saturating his underpants and sliding down the back of his legs. Did he care? Not a jot.

As he neared his hotel he prayed that he should not run into Chai, but he had gone home long before and was sitting with his wife and two kiddies watching Walt Disney cartoons on their television.

In the sanctuary of his hotel bedroom Jack literally sank on the bed and attempted some sleep. This was denied him. There were so many images playing across his mind that it seemed that sleep was being denied him totally. He kept bursting into smile, reliving all the extraordinary things he had done with Suzy that evening. It was as if he was a guy in love.

Well past midnight he gave up on sleep and took a shower. Opened a bottle of a local wine he had purchased that afternoon, he drank the whole bottle with some local bread to soak some of it up. Thankfully he did achieve some fitful sleep come the morning.

He met Jerry in the breakfast area, one of hi football gang. Evidently there had been a big bust-up the evening before. A group of seven of of the lads met up with a similar group of Bayern Munich supporters in a bar somewhere. They got on great until the Football World Cup became the topic of conversation. Then the fists and the bottles started to fly. All of them ended up under police escort and had not been seen since.

"I bet Eugene was in the centre of the action." Jack commented knowingly.

"No, he wasn't." replied Jerry. "He and Phil and Calvin were off shagging some ladyboys they had teamed up with that afternoon. The three of them came back to the hotel late last night."

Talk of the devil and Eugene appeared with Calvin at his elbow. "Hi lads, how's it going?"

Jerry told the story of the fate of the Magnificent Seven, as h called them. It was agreed that the three of them would go to the police station after breakfast. Jack excused himself from that chore. He had one day let in Pattaya and he a very firm conviction as to how he would spend most of it.

He swam in the sea and sunbathed on the beach and ate some food, until the appointed hour. That he had set at four o'clock in the afternoon when, he had been told, the Sleepy Python usually opened its doors for business. He was there right on time, only to be bitterly disappointed. He ignored the "Closed Today" sign taped on the door and knocked. Then knocked some more. Eventually the door opened and a very thin, elderly man appeared. Having little English he eventually convinced Jack that Madame had taken all the ladyboys up country to some sort of religious festival, and they weren't expected back until the early hours.

A lonely day got even lonelier for poor Jack. At midnight a coach a coach was booked to take the football club party to the airport for their departure back to the U.K.

**********************

"Ah, you're back I see, dear boy," welcomed a jovial Quinton Hurst KC as he entered the office, finding Jack sitting at his usual desk.

Yes, sir, I am," replied Jack respectfully.

"And did you enjoy yourself?"

"A curate's egg, sir, good in parts."

Quinton guffawed. he did nothing by halves. "And did you spend my money well?"

Suddenly Jack was lost for words. Instead he blushed deeply. Quinton was on him - there were no flies on Quinton. "Why are you colouring lad? It was yours to waste. what did you do with it?"

"Your instruction to me was that I should get laid, as I remember," replied Jack daringly. He had thought of little else since the plane had taken off from U-Tapao International Airport.

"Good god, so they were," coughed Quinton. "And you followed my instructions to the letter?"

"I did rather, Sir."

"Good on you lad. I hope she was pretty?"

"Very pretty."

"And I take it you took all the right precautions? This world is hardly ready for any more Jacks like you."

Jack blushed more and did not answer.

"Don't tell me you're heading for a possible paternity claim?" He frowned then added lightly, " I could be charged as being an accessory after the fact."

"Oh, no, Quinton," Jack said hurriedly. "She was a ladyboy."

The barrister pulled himself up to his full height, "a ladyboy?"

Quinton's reaction reminded Jack of of Oliver in Dickens' Oliver Twist asking the Master for more food. "She was gorgeous."

"She was a man with breasts, not a woman with a penis. Best remember that dear boy," said the pompous old fart.

************************

A fortnight later Quinton Hurst K.C. called Jack into his office for what he called "an informal interview".

"Take a seat, Jack, dear boy. You know I have taken a special interest in your well being and I have hopes that you will progress and one day be a King's Counsel like me."

"That's very kind...."

"Please don't interrupt me. A very good way to give you a leg up is to have you indentured as it were, to an up and coming barrister rom whom you can learn to be one of the very best. Luke Dangerfield is such a man, and his office is in the chambers opposite to ours. I have spoken to him informally and, subject to a few minor conditions, he will consider taking you on."

"That's marvellous. Thank you o much Quinton," Jack was ecstatic.

"You haven't heard the main condition yet. Luke Dangerfield is openly gay. If he were to take you on as his pupil and protégé you will need to be available to him and his friends. I told him that you had recently holidayed abroad and the height of that trip for you was having had a sexual experience with another man. I think that might have clinched the deal for you, you lucky young rascal."