A Ladyboy Syndrome Ch. 02

A LADYBOY SYNDROME 2

SO FAR: Young Jack Pope, a legal clerk, joined a gaggle of fellow footballers for a short stag party trip to Pattaya in Thailand. There the young innocent enjoyed a fantastic experience with a ladyboy which served to cloud his sexual identity. Head of Chambers, Quinton Hurst K.C. made a questionable assumption on Jack's return from holiday, and suggests to Jack a possible pupillage with the outwardly gay barrister Luke Dangerfield K.C.

The fact that Quinton has misinterpreted Jack's one-off entanglement with a ladyboy went to show exactly what an old duffer he was. It was an classic example of intergenerational misinterpretation.

Jack had rather seen Suzy as a girl with benefits than a boy with tits, as Quinton had so crudely observed. And, apparently from that observation; Quinton seemed to have assumed that jack was gay.

Most young heterosexual young men would likely be offended by such a suggestion, and might make a strong protest vocally. Instead, Jack's first reaction was to remain mum. He was focussed on the mention of a pupillage with an already renowned star at the courtroom bar.

Jack had not been born with a silver spoon in his mouth and his parents had had to really struggle to keep him in school until he was nearly eighteen. The sons and daughters of the rich had almost a right of passage to a good university and perhaps to sit for a law degree, to become fully fledged barristers.

Jack could achieve that end ultimately by being articled to a set of law chambers and working up from there. Having a top barrister such as Luke Dangerfield as his mentor would almost be a guarantee of success, unless Jack fucked up badly.

Women and girls sold there bodies. Prostitution was renowned as the oldest profession. Suzy back in Pattaya was doing just that too. And yet, when she had fucked him with her little penis it was a delight. Is being buggered really a big deal? A distance objective was to find himself a pretty wife, buy a house and have three children. Couldn't he take a form of sexual sabbatical until the time he qualified for the bar?

And if he qualified, by hook or by crook, would that not justify all the sacrifices his parents had made for him over the years. Wasn't that a goal worth chasing, never mind the route taken to get there?

Of course, when Jack wanted to run into Quintin Hurst he could not find him anywhere. He did know where the old roué's watering hole was, and so Jack took himself to the lounge bar of the Wig and Feather just after six o'clock. He was giving Quintin a head start of half an hour, time for him to have absorbed a couple of whisky chasers.

"What brings you here, dear boy," asked Quintin, somewhat less than delighted to see the young clerk invading his drinking hole.

"I'm sorry to disturb you Quintin, but I have being trying to find you all day. It's about that suggestion you put to me. A pupillage with Mr. Dangerfield? I would appreciate you to put in a word for me please."

"Ah, Barkis is willing eh?"

"Pardon?"

"David Copperfield, young man. Charles Dickens. You must have heard of him. Women have been selling there cunts throughout the centuries to gain wealth and power. Why should you be any different dear boy. I'll have a word. Now, be a good man and fuck off."

Jack left the pub with a thin smile on his face. "They didn't make many like Quintin Hurst, thank God."

The hoped for interview with Luke Dangerfield materialised some weeks later just as Jack was ruling against the possibility. The barrister could have been a male model; slim, tall, lightly tanned skin, blonde hair and twinkling green eyes. He smelled of a light and fresh perfume and one would imagine that his personal hygiene was impeccable. A woman's dream if not not to be a woman's prize.

"I have read your staff reports an made some enquiries about you Jack, and they are very complementary. It appears you have a good brain, that you know how to apply yourself, and you have ambition. Quinton has mentioned you are gay and that will not disadvantage you in my chambers. Most of us are of the same persuasion and, providing that you fit in, in that regard, you should become a valuable member of the team."

There it was, Jack's future to become a barrister laid out before him, a chance in a lifetime. Subjecting of course to him "fitting in". He thought he knew what that meant. Jack was no fool in that regard. As the junior trainee, with girly looks, and credentials stemming from Pattaya no doubt, was he going to be considered to be "fair game?

There it was - a stark choice. Take it or leave it.

He didn't toss a coin. He didn't ask divine providence to intervene. He could not ask family or friends. He just said "yes".

"You can call me Luke in the office," volunteered the barrister on Jacks first day. We are informal in chambers, very formal outside. That's in the way we dress and the impression we give. Remember that Jack. Breaking that rule will be your fastest exit from here. Understand?"

"Absolutely," Jack assured him.

"Second rule. No hanky-panky in the office and discretion at all times. You are new to the scene, but I am sure you know the pitfalls. All liaisons in strict privacy. O.K.?

Collectively, we have a bad enough reputation as it is. You may have already heard the slang for our chambers, The Poofta's? Not all of us are gay - a couple of men and three of the girls are straight as far as I am aware. By the way, I hear you had a fantastic experience in Bangkok?"

"Pattaya, sir" Jack corrected him.

"You really must tell me about it sometime. Right Jack, I'll get Tom Bates to show you what's what and to introduce you to all your new colleagues. You'll be wise to make a friend of Tom."

That last sentence reverberated in Jack's brain. He saw his new mentor as a friend rather than a foe, and was keen to follow his directions. Tom Bates did come as a bit of a shock though. He was fortyish, tubby, as short as was Jack and with a few strands of black hair precariously spread across his bald pate. Didn't anyone love him enough to tell him hope stupid he looked?

He appraised Jack in a disconcerting manner. Had not the young man heeded his boss's words he might have said something quite rude. For his pains Jack's nose was assaulted by a very strong whiff of cheap perfume. Definitely not aftershave but perfume. To cap it all, Tom's mannerisms were markedly effeminate. "I'll take you to your work station and introduce you to your new colleagues," Tom smarmed.

The first four weeks were just a rash of new faces and procedures. Everybody, without exception was friendly to their new recruit and apparently eager to help Jack settle in. Most of the office staff commuted in in the morning, performed their word, and commuted out in the early evening. The barristers and their clerks and assistants, as often as not, scurried in and scurried out according to their court schedules. Luke took Jack with his team to witness a couple of cases and he arranged for Jack to join other barrister's teams for odd days. Jack was learning fast.

The first rub came when Jack was invited to a party by Nick Blair, a computer specialist The rub? It was a guys and dolls party and Nick wanted Jack to be his doll. "You're an absolute cinch for it, Jack, with your height and delicate good looks you'll be the belle of the ball. I can get you kitted out."

"Delicate good looks?" He meant feminine good looks, Jack knew that for sure. Still. what harm could it do. He was ripe for a bit of fun having worked so hard the last month. And Nick was a nice guy, popular with most of the chamber, and especially with the girls. Jack could not imagine that he was gay. Perhaps there was an iota of regret in that observation?

Jack rushed away from his Saturday afternoon's football in order to be "dressed" by Eva, Nick's wife. She was really up for the challenge. which started with Jack in the shower. She was much the same size and build as her charge and so it was her wardrobe she consulted in order to make up the appropriate costume.

She started with a pair of white panties possibly a size and a half too small in order to keep him "tucked up nice and tight". She seemed to want to watch him put them on, him being naked save for a bath robe after showering.

"I'm a nurse," she said. "I've seen it all."

That was no consolation to Jack's embarrassment.

Just as well though. When the red suspender belt and the black fishnet stockings appeared Jack's penis woke up and he was very grateful for its suppression in the white knickers. Her bringing out a bra did not help though. "No Eve, I am not wearing a bra." Jack was adamant.

Ten minutes later Jack was wearing the bra and Eve was busy stuffing it with cotton wool. "You have to look the part, darling," she had scolded him, "else you'll just be a figure of fun. Besides, there is a money prize for the best dressed doll, and if you win I will expect you to share it with me."

Control of his libido was not made any easier for Jack as Eve was careless with her body. She was very touchy-feely and several times she had leant over him pressing a breast into his face. "Was she doing this on purpose?" And after an hour of Eve fussing around him making his face up, his prick seemed to be frozen in its most agitated state.

The first sight of himself in a mirror gave Jack a huge jolt as if he had touched a high voltage electrical current almost. He just could not believe the face looking back at him. She was gorgeous - no other word would suffice. Never would he have recognised himself.

Jack was not surprised that the event was being held in a gay club. He had heard of it only because of chat in the office. There were great number of revellers and many had taken up the costume challenge and dressed as Guys and Dolls. Jack found himself attracted to several of the lesbian "guys", of all people. There was a sexual electricity about the whole place and he was getting caught up in it.

The event was brilliantly compered by a drag artiste whom had been specially hired for the event evidently, and the first half of the evening passed in song, laughter and dance. Jack found himself short listed for "Belle of the Ball" but he was no match in the end for the best of many amazing costumes.

Nick knew a surprising number of the revellers, and many came up to him to made personal contact. Some, it appeared, wanted an introduction to Jack (he was Jacqueline for the evening) but in the main Nick headed them off. Jack began to suspect the main reason was that Nick did not want to risk too much being revealed about himself.

The party was at its height when Nick excused himself asked if Jack amuse himself for half an hour. "Business calls," he said, "I need to have a talk with an old client of ours." Jack took that to mean a past client whom had been defended in court by his chambers. Suddenly he felt really quite vulnerable and he sought sanctuary in the relatively quiet bar area where there were seats. He sat down at an empty table with a glass of red wine and almost immediately the seat beside him was taken up by a doll with two blonde pigtails and a chequered pinafore.

"Hiya, I'm Andy. Nick asked me to keep you company whilst he attends to some business or whatever. I'm delighted to meet you. I saw you in the parade. You was robbed," he said playfully.

"Do you really think so," replied Jack mechanically, not really wanting to enter into a conversation.

"I think you look the sexiest of them all. You'd have my vote any day of the week. I haven't seen you here before?"

Before long they appeared to be any two pretty girls chatting together animatedly, an empty bottle of wine on the table and a second, half full. Andy was a adept conversationalist and had drawn Jack out to learn pretty well whole story of his recent trip to Thailand. He too had visited the country, to Bangkok, and with the particular intent to engage with ladyboys. "They were really sexy and I would go again tomorrow," was his endorsement.

And that was just what it was to young Jack - an endorsement. In Andy he appeared to have found a kindred spirit, an an endorsement for what he had experienced and enjoyed with Suzy. Andy was relating some of his experiences there when Nick turned up at their table.

Acknowledging Andy, he turned to Jack. "I've got to go home Jack. Eve's got trouble with our youngest. I can drop you back at your flat if you like. I hate spoiling your evening, but I have to fly.

"You can stay at my place if you like," piped up Andy. I live only just around the corner. I would like to get to know you better. We seem to have so much in common."

Jack was torn. He needed to make a decision in seconds. He was enjoying himself in the club and did not really want to leave. This was his first evening out in months. He turned to Andy. "Are you sure?"

"Absolutely."

"Are you staying," asked Nick, obviously anxious to get away home.

"Yes Nick, thank you." Decision made.

They finished the bottle of wine and then Andy led Jack by the wrist onto the dance floor which was the usual seething mass of humanity of all different shapes and sizes and colours. If they were a couple of honeys, there were plenty of bees trying to get at them; gay guys and lesbians too. It all added to Jack's education according to Andy.

Then the mood changed. A couple of tipsy guys persisted in not accepting "no" for an answer. Andy knew them and pulled Jack off the floor. "Time we left. Trust me."

And Jack did trust Andy. Except his flat was not "just around the corner" but a short taxi drive away. Far enough though for Jack to have no idea as to where he was.

From what could be seen in the light of street lamps it was a smart, period building that had been divided into flats. "Mine is the garden flat," Andy explained as he manoeuvred Jack past the front entrance and down some murky steps to one side. It was like descending into a cellar. "The ground slopes away at the back and the flat overlooks the garden. You'll see for yourself in the morning."

Andy opened what was the front door and stood aside allowing his guest to enter first. The flat was bright and airy with pictures and posters on every wall just about. In the neat kitchen, Andy turned to his guest. " I want to kiss you. I've been dying to all evening."

Those words hit Jack like an electric shock. He would have to admit that he had wondered at various points during the evening, what it would be like to be in bed with Andy, especially when they were talking about their ladyboy experiences. But that was there and this was here, and a lot had gone on in-between.

Andy seemed to take Jack's hesitation as acquiescence, and before Jack knew it he was in an embrace with Andy's lips searching for his - made more erotic as both had remnants of of lipstick. Jack didn't respond positively, but he didn't resist either. That was Andy's excuse to slip his tongue in-between Jack's lips. His was a rough male tongue, so unlike that of his erstwhile girlfriends.

Andy was twenty-four, long term gay, and knew most of the ropes. Jack was just nineteen, one experience with a ladyboy, and on the point of being persuaded that cock is best. Andy was a top and a predator. Jack was an aspiring bottom and vulnerable. Possibly, Andy's flat could be pivotal in terms of Jack's future sexual preferences.

Jack extended his right hand round Andy's waist and pushed his groin forward. The kiss grew in size and length and Jack's tongue became active too. Andy pulled up Jack's short skirt right to his waist and then, with both hands, played with the stocking tops and suspenders, deliberately missing, and therefore teasing, the jewels that would soon be his.

Andy's skirt had an elasticated waist which Jack quickly discovered. Using both hands he pushed it down to fall to the floor. Andy's stockings were hold-ups and he too had on offer that gorgeous flesh between knickers and stocking tops. Nevertheless Jack went straight for the big prize, which was not so confined as his own.

"Hey, slow down darling," Andy breathed. "We've got all night. Let's make for the bedroom." He took Jack's hand and led him away. The bed was king-size and the mattress thick. Jack allowed himself to wonder how much action it had seen in the past as Andy undressed him. Off came the stupid bra leaving just knickers and stockings. Andy went down on his haunches to ease down the knickers causing Jack's super-hard penis to shoot straight out celebrating its new found freedom. In one second Andy's mouth was just inches away - in a couple of seconds more his mouth was sucking on the organ and Jack's sexual dilemma was pretty well resolved.

Andy was no fool and was somewhat of a humanist too. He was also crafty. He guessed that, if he gave the inexperienced lad a good experience it could likely lead to a longer term relationship with such a pretty boy. and whom could become putty in his hands long term. On that basis Andy relegated his needs into second place. The situation needed some hasty planning. The first decision was crucial. Did he, or did he not, blow the boy there and then? The risk being, as most men will testify, the lad, lust satisfied, could lose all interest in any further play and insist in making his way home.

Decision made, Andy concentrated hard on sucking the lad's cock using all the skills and tricks he had learned over many years. He knew that Jack would not last long so he ran a hand up between Jack's legs and inserted a couple of fingers in his arse crack. One finger was soon playing with his sphincter - it was important that Jack, at an early stage in his sex education, learned to associate pleasure in his genitals with anal play. He would like to have lubed him, but there was no chance of that on this occasion.

Everything was now in place. Andy's bobbing head delivered a few high pressure sucks and Jack started moaning uncontrollably, wallowing in lust with the beginnings of a huge orgasm mounting. As it exploded and Jack's body writhed, Andy pushed his finger at least an inch inside Jack's arse. and wiggled it about fairly gently - but enough for the message to be received. All the while Luke was swallowing a healthy stream of Jack's warm cum.

Before Jack had fully come down off his high, Luke undressed him fully, then himself, and bundled him into the shower together. Pity about the remains of their face paint - nothing could be done about that. The game was to get Jack into the double bed as soon as possible and, both naked, for Luke to cuddle him to sleep. All part of that hastily improvised plan. And it worked.

Jack awoke as dawn was breaking and the morning chorus was coming in full throttle through a half open window. It took him awhile to remember where he was and the means of his getting there. Images of sex he had enjoyed in that big soft bed flooded back, and his penis started to think about reacting accordingly. No, he needed to piss first.

Thus relieved, the bathroom mirror reminded him he still had the remains of Eve's make-up round his eyes in particular. He did his best to remove the worst using toilet tissue. In theory at least, Jack could have tip-toed around, gathered up his clothes, and escaped from the flat. He did process that opportunity. but the warm and inviting double bed of Andy's was the main contender. Or was that just a blind? Was it more of Andy he craved? Live for the day, eh?

Jack was back asleep when Andy stirred and awoke. He in turn slipped away and performed his ablutions, cleaning his whole face from the remains of the cosmetics and taking the opportunity of a very quick shower. He doused himself in a musky perfume.

He could see that Jack had been in the bathroom before him. Andy's mouth broke into a smile of satisfaction. His target had not chosen a golden opportunity to slip away to his own home. Things were looking good - extremely good in fact.