A Ladyboy Syndrome Ch. 04

A LADYBOY SYNDROME Ch. 04

SO FAR. Young Jack falls for a ladyboy during a visit to Thailand. As a consequence on return to the UK Jack is offered a tutelage in a legal chambers favouring gay men and women, He meets Andy, a predator, who intentionally develops Jack's embryonic tastes for gay sex, and then sets about feminising him. He takes Jack to a partner-swapping party where he is accidently paired off with quinquagenarian (50+) Bernie.

Jack quickly weighed up what was expected of him as he knelt between the legs of the paunchy Bernie, a man older than his father even, and who was sitting naked, except for his shirt., and waiting for some attention.

As he took the man's cock in his hand Jack couldn't help wondering how many cunts and how many arseholes the venerable member had fucked. Now he, Jack, was part of that scene and making a contribution. So far so good. He clamped his lips round the aged cock and sucked and licked with gusto.

Jack was learning that there is something very special about sucking another man's cock. It has to be the most intimate exchange between two men surely? Just the thought of it was sufficient for Jack to experience a small shiver of excitement in that he was having a part to play in such a history of debauchment. That made the licking of the aged circumcised head more compatible - quite considerably so in fact.

Jack delved into erotic images of where the actual cock he was sucking might have explored over many years. Such thoughts helped get Jack's penis throbbing and his libido heightened. French knickers are designed for access, but in Jack's case access meant egress too and his prick was soon standing out proud and unencumbered. The short dress Jack was wearing was no hindrance either, and Bernie was not slow to notice how Jack's libido was performing. "Stand up," he ordered.

Jack struggled to obey. Bernie slipped off the chair and onto his knees so as his face was within inches of Jack's throbbing and unencumbered prick. The cotton fabric of the dress fell down hiding it, That was no bar to Bernie of course. He looped his head under the fabric and accessed Jack's rampant prick full on.

Jack shuddered with a sexual spasm the likes of which, he thought, at that instant, he had never experienced before. He lost control of himself and before he knew it he was spurting everywhere. Bernie was clearly caught out, but he had the nouse to wrap his mouth round Jack's prick, just enough in time to catch much of the youthful semen.

"Wow, darling boy, you've excelled yourself there. You're a natural faggot. Welcome to our world." Bernie's enthusiasm seemed boundless. "And your spunk is really tasty," admired the older man, licking his lips. "Nothing beats the fertile seed of a man in the latter stages adolescence. Young creamy, tasty spunk. When I can get some it is like the elixir of life. Whereas, old man's semen, like mine, is more....." He stopped short. "Have you ever tasted it?"

Jack lied through his teeth by assuring Bernie that he had.

"Instead of you sucking my cock then, I'll fuck your arse. No need to take any of your girlie clothes off. I love fucking men in French knickers. Let's have a drop more of that red wine first."

They killed the one bottle and started on the second. "Those titties of yours, are they real?" observed Bernie.

"Of course not. It's just padding. It was Andy's idea."

"He said you had a run-in with a ladyboy in Thailand? And, thanks to that experience we have the pleasure of you at the party this evening?"

Jack found himself blushing. "You could say that."

"I've fucked a few of them in my time - ladyboys. And they've fucked me. Lovely." His face mirrored the truth behind his words.

"Yes," agreed Jack, a little wistfully.

Bernie looked at Jack, up and down. "You'd look great with boobs Jackie. You've got just the right physique. I have a surgeon friend who owes me a favour or two. He would negotiate on price in lieu of services you could render him afterwards. Give it some thought, eh?"

"I will," Jack lied.

"Right. Bend over yonder chair and I'll fuck your arse." And more o himself, "where's that fucking lube."

The sexual act that followed does not merit recording in any detail. The old roué used Jack's anus as a means for his pleasure of course, but his pleasure alone - and then as a repository for his sperm. No talking - just grunting, no caring, just total selfishness. Jack had every right to think hr had been used. He felt he was little more than a rent boy without the rent.

Perhaps that was a lesson that he could not learn too early in his new pathway as an aspiring faggot.

When Jack eventually regained his footing Bernie's sticky cum slithered down the bare skin of his thighs and impregnated the tops of his black mesh stockings. His cotton frock was similarly stained and, of course, his knickers too. Then Bernie insisted they finish the second bottle of wine "before re-joining he party".

Jack drank more of the wine than he wanted to just to get away from Bernie's company. He had had his fill of the selfish old man in more ways than one.

Thankfully, Back in the main party room Andy popped up at his elbow, "How did it go?"

Jack dodged the question by turning it on its head, asking Andy how he had fared.

"I gave him a quick wank. I didn't fancy much more."

"Mine was a bit like the curate's egg, good in parts," Jack admitted.

"Shame, I had originally set us up with a really nice couple for a foursome, but because we arrived late.....What we got was not what I intended."

"I'm all sticky," lamented Jack to avoid commenting about Bernie any further.

"Come on then, let's fuck off out of here. There's a towel in the car you can sit on. Then shower at my place?"

"No Andy, thank you. Would you take me home please."

As a matter of speaking, Jack retreated into No Man's Land thanks to that one experience with with Bernie. He was used and he felt used. That was a far cry from the romantic type experiences he had experienced before. He started questioning his sexual orientation in earnest. Over the next few weeks, In the privacy of his own flat, just occasionally he "dressed", when the sap was running high. At other times he bagged up his female finery. determined to leave them out for the bin men to dispose of them..

Andy tried to engage with him frequently, but to no avail. Jack was sitting "neutral".

It would have surprised Jack to know that someone very senior indeed had been appraised of Jack's apparent dilemma - none other than Luke Dangerfield K.C., Head of Chambers. Luke did not openly associate with any of his staff outside of the office, but he did manage them in a quirky sort of way through his "contacts". It was no accident that Jack was given young Denny as his assistant for the duration of "a special project."

Denny could pass for eighteen, but was actually nearly twenty-three. He may have looked innocent to an outsider, when in fact he had engaged in a whole cuvee of lechery. Why would someone as important as Luke Dangerfield set Denny O'Connor on some innocent's tail? There must be a motive in there somewhere.

After just a few day of working together Denny wheedled an evening visit to Jack's flat on the pretext of sharing an Indian takeaway. The flat was in a block and Jack needed to whiz down to the communal entrance in order to receive and pay the delivery boy (actually it was a woman). Whilst Jack was doing so, Denny took a whiz of his own and discovered Jack's femme clothes in a bin bag, in a corner of his wardrobe. A knowing smile cracked across his face. He was siting back in the lounge looking as innocent as driven snow when Jack walked in with the food in a carrier bag.

On his next visit to Jack's flat Denny steered the conversation round to clothes, and then he found a pretext to get Jack to invite him to visit his wardrobe in order to show Denny a particular leather jacket. In doing so Denny "discovered" Jack's bag of feminine clothes, and he had it opened before Jack' alarm could take precedence.

"Oh, how exciting is that? A fellow cross-dresser. I just love to dress in girlie clothes. I have a whole wardrobe at my place. You must come and see."

Jack wasn't at all sure. He was feeling randier than usual for some reason rather pleased he was to find a fellow dresser. And it was really quite disarming to learn that Denny got a kick out of dressing up, just as he had done with Andy. He might have thought it was strange, the number of cross-dressers he was coming across.

Denny started undressing. "Come on, let's be a couple of silly girls. Got any underwear?"

Jack would like to have thought that, up to that point in their relationship, he had not eyed up Denny in any sexual way. That was not quite true, but it was low level stuff - just as a truly heterosexual man would eye-up any woman perhaps. But seeing Denny caste off all his clothes with seeming abandon, right next to he Jack was standing, did start the reaction he had tried to avoid for many weeks. He had to dodge about so as to avoid Denny seeing his hardening erection.

Denny's penis, on the other hand was open for display and completely flaccid. There was no evidence at all that he fancied some sexual exercise with Jack, and nothing in his body language suggested otherwise. This gave Jack a measure of confidence and, no doubt about it, some of disappointment too. He had never heard of RE-ZIST, the little pink capsules that kill the libido stone dead for a couple of hours or more. Denny wanted to fuck Jack's pretty arse right enough.

Jack chose some tight panties for himself., bought for the job of keeping his excited prick in check, and he became more confident wearing a short but flared skirt. Danny chose an equally short pencil line dress and hold-up black stockings. They each applied a little make-up and then retired to the lounge where they drank wine and showed off their legs. Jack was fired up to the hilt, or so it seemed.

After about an hour Denny excused himself saying he needed to visit the bathroom, but he returned dressed in his street clothes and he seemed to make an all too swift getaway. "So far, so good," he assured himself.

Jack's intentions to put all sexual pleasures on the backburner for a while had taken a beating that evening. All the most intimate moments he had enjoyed with Andy came flooding back, whilst even the experience with Bernie was credited with some good moments too. Denny was certainly rattling Jack's sexual cage.

In the office the next morning Denny acted as if the previous evening had not happened. This added greatly to Jack's confidence in him. Before the end of the day it was Jack who approached Denny suggesting they enjoyed another evening together. What he would have liked to have said - "an evening dressing up together."

"Next week sometime perhaps?" said Denny, sotto voce, keeping casual.

Jack could not prevent his disappointment showing on his face. "Oh, not sooner?"

"I could be free tomorrow night, I suppose," said Denny. "I am needed to help Luke in court tomorrow, but I could be at your place for about seven?"

"Can we dress again?" asked Jack bravely.

"Absolutely," grinned Denny. "See you then."

The following morning Denny caught up with his boss, Luke Dangerfield K.C. in the Robing Room of the County Courts. "Good morning, sir," greeted the young man politely.

"Ah, 'morning Denny. How's it going?"

"I'm well, sir, thank you."

"I mean, how is it going with young Jack Pope?"

"It's a cinch."

"What exactly do you mean by that?"

"He's had a wobble, that's for sure. But he's got the hots for me, sir, and I may reel him in as early as tonight. Of course, it will take longer to stabilise him."

"Of course. Do you think he will go for the - er - amendments?"

"Can't say yet sir. That's asking a lot."

"Do your best Danny. There's a lot riding on it." He consulted his wristwatch. "Time for a quickie eh?"

Denny followed his boss through a door marked "Barrister's Lavatory". Luke had his trousers undone and lowered before Denny had time to secure the cubicle door. "Why do barristers insist on wearing white, cotton jockeys?" Denny asked himself as he lowered himself to the floor. He should know - he had sucked enough of them off. Luke's assets were all too familiar; seven and a half inches, thin, cut and always very clean. Smelled good too. Denny guzzled. Mmmmm. Nice. "A pleasure to serve," had a meaning all of its own for Denny the Faggot.

That evening Jack found his excitement growing as the hands of the clock reached seven of the hour all too slowly. He was showered and squeaky clean, naked inside a track suit. The thought of ending up in bed with Denny had crossed his mind - a lot.

For his part Denny was on the horns of a dilemma (sounds good anyway). As he pre-pared himself ready to visit Jack in his flat. Should he take a dose of RE-ZIST or not? A flabby, unresponsive prick or his natural one? Was Jack ready or wasn't he?

As the front door opened to him the omens were good; Jack was wearing a track suit. Denny would have wagered a penny to a pound that Jack was either naked underneath or almost so. He leant forward intending to kiss Jack, but remembered just in time they had not reached that stage of intimacy quite yet. "Hi girlie," he greeted teasingly.

Jack smiled, obviously liking what he had heard. They moved into the living room and Jack asked of the small case Denny was carrying, "what have you there?"

"Clothes, of course. For us to dress up in. I can hardly wait," Denny said genuinely. He was getting real hots for young Jack, not just professional ones.

"Wine or coffee?"

"Red wine would be nice, thanks."

A few scoops each and then they made their way to the bedroom. Denny opened up his bag and pulled out two stretch rubber panties about half the size of normal. Jack picked one up as he was meant to do. Looking suitably quizzical he asked the obvious.

"They are what I call restrictor pants," said Denny, deliberately mysteriously.

Jack didn't fall in. "What do they do?"

"When we're cross-dressing they help keep the line."

"You mean.....?"

"When you get an erection it keeps your prick close to your body helping not to spoil the line of your female clothes."

"Oh, I see," said Jack, a little embarrassed it needed to be spelt out to him. But," he asked naively, "when you were last here you seemed not to have a problem with, you know, that."

"Because I took an orange pill before I came here," smiled Denny with contrived coyness.

"An orange pill? I know about little blue ones. They help older men get an erection?"

"The orange pills achieve the opposite," revealed Denny evenly, alive as to what effect those words could have on Jack.

Jack blushed deeply. "So what if you hadn't taken an orange pill?"

"I would have had an erection every bit as hard as yours, Jack."

Jack felt pleased and embarrassed and apprehensive all at the same time. He felt his prick getting more than interested. "Perhaps I had better have a pair of those restrictors of yours." Instead, they both decided to be "brave" and get along without them.

Denny had brought with him the classic sort of clothes for young men to dress in and feel sexy; short tight skirt, strappy silky camisole, loose fitting printed shirt, suspenders stockings and French knickers, silky and white.

They had a lot of fun trying different cosmetics of which Denny had brought a range. Being older, and out on the town longer as it were, he was far more experienced in their application than he revealed to Jack. Importantly he was able to ensure the end result was attractive rather than a farce and a source of amusement. He needed to keep the atmosphere on track.

They returned to the lounge in all their finery and enjoyed a laugh and a few more scoops of wine. Denny timed his moment to perfection as he gently pressed his ruby red lips against the pink ones belonging to Jack.

By then, kissing was familiar territory for Jack and so he was not startled in the slightest. Being seduced by another man was fast becoming something he could not resist. And that most certainly included a man "dressed" as it were. As Denny's tongue tentatively started on the road to asserting itself, Jack's mind was constructing a picture of Denny's prick starting its journey up Jack's arse.

What Jack didn't expect, but was delighted with, Denny took the lead in every way and seemed to be keen that Jack remained submissive. As far as verbal endearments went, Jack became Jackie, and whilst Denny stealthily wriggled out of his female apparel, he insisted that Jackie retained all of his.

At one stage, Denny left the bed and went to the bathroom in search of lube or a suitable substitute. Jack was left to admire his lover's athletic body with its sizeable and rampant prick swaying at a stiff right-angles to his flat stomach as he slipped round the bed to the door. He wanted him. There was no doubt about it. Jack wanted Danny to fuck him. And before that came the desire to suck on that ever gorgeous cock.

When Denny returned, a jar of Vaseline in hand, his prick was just as hard and desirable. Jack turned over on the bed without being asked and positioned his chest on the mattress and his arse in the air. For his pains Denny gave the latter a stinging slap, And then another, and another. That certainly gave Jack something to think about as Denny applied the ointment, first all round Jack's arsehole. and then liberally round and up and down his own cock.

The stinging of the slaps, the surprise of them as well as the pain. seemed to have heightened Jack's libido even more and the feel of the penis at his gate sent something akin to a shockwave right through his body. Not content to allow the purple head of Denny's prick free entry, Jack actually pushed back onto it, taking in a good two inches, and without much pain. Over the next five minutes pain abandoned itself to pleasure, and at that point Denny really started shagging Jack's male cunt in earnest.

Jack, shoulders down and arse in the air, had a free hand which he slipped round to grab hold of his own cock. It was as excited as he could ever remember it being, and welcomed the hand that slowly started to pump it. Denny was taking him - there were no other words necessary to describe the intent and the urgency. The action was furious - too furious to carry on for long. Denny started moaning as he neared orgasm and Jack, orchestrated his own climax for them to happen together. What a lot of wailing as Denny's hot sperm seem to fill to overflowing Jack's arsehole, whilst Jack's semen spurted everywhere.

They just lay there. Neither were counting but, if they had have been, it was just over ten minutes. Jack on his stomach on a pool of semen, all his own plus some of Denny's, and Denny lying bottom half on him and top half cuddled protectively into Jack's back. Words not needed.

At another lime, on another day, they may have fallen asleep as they were, just like that. Jack was on the point of sleep when Denny disturbed him. He had a message to deliver, and he judged that that moment was the right time. "I'm what they call a 'top' Jack. For want of a better description I take the man's role. You are a natural 'bottom', and you take the female role. You like being a female Jack. That is your metier, what you were born to be. So I won't be dressing femme any more and you always will when we are together. Do you understand what I am saying?"

"Does that mean I never ever get to fuck your arse?" giggled Jack.

Denny giggled back, relieved that his little homily had been taken so well. "Yes, and your arse is your cunt as far as I am concerned. Don't you forget that. And there's one other thing."

"Just one?" said Jack cheekily.

"You're far too hairy to be a female. We'll have to get that remedied tout suite."