A gay story: A Ladyboy Syndrome Ch. 03 SO FAR. Youthful trainee lawyer Jack falls for a ladyboy in Thailand and, in a misunderstanding about his sexual orientation, he is offered a tutelage in a chambers favouring gay men and women staff. Colleague Luke invites him to a Guys and Dolls Ball where he meets Andy who persuades him to overnight at his flat, with lascivious motives.
Jack awoke to find Andy virtually standing over him with a cup of coffee in his hand, obviously meant for him. He closed his eyes and stretched languishly. The smell of perfume on Andy’s body aroused his senses, as it was meant to.
He opened his eyes again and the coffee was in the bedside table and Andy was still standing where he was, his dressing gown sufficiently open at the front to allow his shaved pubes to be not just visible, but a matter of inches away from Jack’s mouth. Jack surprised even himself by stretching out and and giving the penis an affectionate squeeze. He couldn’t just ignore it could he?
Encouraged, Andy dropped to one knee, leant over and kissed the young man full on the mouth. It wasn’t any ordinary kiss. It was long and it involved Andy’s tongue extending to its fullest as if intent on searching the whole of Jack’s mouth. The boy surrendered and drank all the pleasure from doing so.
Andy stood back up and sloughed off his dressing gown, his prick now fully alert. Pulling Jack up into a sitting position he stuffed two pillows between him and the headboard. The boy’s mouth was at exactly at the right height to accommodate the penis that was then pointing directly at it. There was no question as to what was going to happen next.
Jack wanted it. He was sold on it. His own prick, still under the bedsheets was just as hard as the one he was being invited to suck.. Andy was quite brutal and deliberately so. He wanted to complete the turning of the boy emphasising his future role to be a committed receiver. It was a form of power game with very significant consequences.
Andy deliberately gave no warning as to when he was about to discharge a pent-up torrent of hot sperm. That was part of the process. Hopefully the next would be into Jacks near virgin arse.
Jack nearly choked on the deluge of hot fishy, salty sperm. A lot ended up dripping down his chin and onto his bare chest. That all added to the drama of the occasion.
Andy nearly made a point of complimenting Jack as he pulled out and backed off, swallowing the words “thanks faggot”. No, it was too early to do so. That would have to keep for another occasion. There would be many more, he was sure. If Jack had not been turned, he was vert close to being so.
Jack, recovered took his own rock hard penis in his hands and offered up a look that said, “what about me?”
Andy was alive to his predicament. “Your turn will come later, darling. It’s the shower for you now and then some breakfast.”
The original cup of coffee remained untouched by the bedside. A silent witness.
The two men showered together in a cubical meant for one. Jacks penis was rampant and Andy’s showing the first signs of recovery. Jack was almost desperate to have Andy touch him deliberately instead of their rubbing up to each other from the lack of space. The most Andy did was give his junior a tender kiss and whisper “later”.
For two pins Jack would have tossed himself off there and then had Luke allowed him to.
Whilst Andy prepared breakfast he wisely turned the conversation to football, to soccer. He had been tipped off that his guest played for Pathway United F.C. and trained several evenings every week in the season/ He went with some of his team mates to Pattaya no less.
Andy expertly ran up a cooked breakfast English-style and they both tucked in ravenously. Jack hadn’t eaten anything substantial for over seventeen hours, as the smell of the bacon frying had reminded him.
Both replete, Andy suggested they watched replays of the Saturday’s football to which his guest readily agreed. They shared the settee, both still in dressing gowns, and whiled the morning away with football almost entirely the topic of conversation.
Eventually, Andy suggested they had a “siesta”. Jack didn’t catch on immediately. Andy slipped a hand under Jack’s gown and rested it on his bare thigh. The boy cottoned on. Strange, the football had transported him far away from thoughts of sexual relations, and Andy’s advance had brought him back with a thump. It was like he was living in two worlds and he was not at all sure he wanted to leave the one he was presently in.
Andy was a predator and as a predator he had predator’s skills. Instead of trying to entice Jack into the bedroom he reached for the television’s control and switched channels to some pre-prepared material. “I thought this might interest you Jack?”
It was porn. But not any old porn. It was ladyboy porn. Fifteen minutes was more than enough to have Jack wallowing in the memories of Walking Street in Pattaya and the lovely ladyboy Suzy. The more time since Jack had returned from Thailand the more sexy and beautiful Suzy had become in his memory.
Andy watched the action with Jack for a good while and then slipped out of the room. He came back, still wearing the same dressing gown, but he had slipped on Jack’s hitherto suspender belt and black stockings; nothing else. Standing in front of Jack he allowed the gown to yawn open enough to give a taste of what lay within, his cock reacting accordingly.
Jack seemed reluctant to drag his eyes from the television scene where a a man was about to take a proffered penis belonging to a busty ladyboy, into his mouth. The real thing was inches from his own lips. He did a double take and, after that, there was no contest. “Let’s go into my bedroom,” whispered Andy.
Jack allowed himself to be led like the classical lamb to the slaughter. Andy threw off the boy’s gown and sat him naked on the bed-end. Standing directly in front of Jack he too wasted his dressing gown, and was quite a picture in just the stockings and a hard, throbbing penis. “Worship it cocksucker.” he ordered.
Something broke in Jack’s head. There was nothing in the world, at that moment in time, that he craved more than to suck the cock. It wouldn’t have mattered whether it was Andy’s cock, Luke Dangerfield’s cock. or that cantankerous old bastard Quintin Hurst’s cock. Any cock would have been the right cock.
“Wait a minute darling.” The instruction manage to permeate Jack’s brain. As did, “kneel on the bed.” Hands moved him into the necessary position. Next Jack felt cold lube being massaged into his his bum hole. Then he knew what was about to happen and he wanted it. “Yes, fuck me,” he encouraged the man in position behind him, and who needed no encouragement whatsoever.
Andy knew it was not so simple as that. Yes, he could “wham, bam, thank you sir,” and enjoy the thrill and debauchery of it all. Another notch on his newel post perhaps. No, No, No, that was not his game. That was not what turned Andy on. What he wanted was the satisfaction of introducing another pretty boy to the thrill of having a relationship, of any type, with another man. And, of course, with him in the first instance.
Andy nestled his cock into Jack’s rear entrance and applied a little pressure. Jack tensed waiting for the explosion o pain, if that was what he was in line for. He had read about anal sex being difficult for the receiver initially. But Andy pulled back and substituted his fingers, and then slipped a slippery forefinger in the same several inches he had done before. And then back came his penis nudging again whilst Andy’s had moved forward and cupped Jack’s balls and caressed them.
Expertly Andy soon had Jack near to be screaming to be fucked.
More lube and Andy started his assault. This time the purple head of his penis did not back off. but pushed inexorably harder and harder, intent on breaking into Jack’s virgin arse. At the start a willing Jack pushed back against Andy’s penis head, but as the pain mounted the boy did well to stand his ground and try to absorb the pain from the pressure his arse was under.
As Suzy’s little prick had managed to force entry there was no doubt that Andy’s would too. And, with some extra aggravated pain, it certainly did. Andy remained still to allow the worst of the pain to subside, his prick probably no more than an inch or so into the boy’s arse. Jack would indicate when he was ready to proceed.
Sure enough, after a short while Jack set his trunk swaying, minutely at first but then with ever bigger forward and backward motions. More to the point, he started gasping and much of that had pleasure mixed un with the pain. Andy smiled evilly to himself. Everything was going to plan.
By the time Andy has virtually the whole of his penis lodged inside his captive he could feel the tightness lessen as Jack’s anus gradually became more receptive. The same feeling in Jack encouraged him to jiggle about as a prelude to some sort of a fucking. Deflowering of a virgin arse was the height of sexual achievement as far as Andy was concerned, and the thrill of doing so excited his need to ejaculate. All too soon he was pumping streams of semen into Andy’s bowels.
It would have been fantastic if Andy had been able to have brought Jack to an orgasm at the same time, but experience told him that rarely, if ever, happened. Given time, that could be achieved. If not with Andy, with Jack’s future lovers. Andy had no doubts there would be many of them
Andy kept his prick inside of Jack until it was made of rubber and swished out of the boy’s anus dripping with semen. He turned the boy on the bed into a position suitable for Andy to suck the boy’s cock. This he did with gusto, obviously enjoying the experience and demonstrably good at it too. It was all sex; beautiful, unadulterated sex.
The next move in Andy’s game was to bundle young Jack back to his flat without further ado. To cut down his face time with him Andy called a taxi. There was some embarrassment on Jack’s part as he had only his girlie clothes to wear. Andy left it to Jack to offer the taxi driver an explanation should one be necessary.
Jack could not walk properly. His anus was bruised and sore and still leaking Andy’s spunk into a sanitary towel. Once home he headed straight for the bathroom and ran himself a hot bath in which he languished until the water was less than warm. What a weekend. One to remember. But to cherish?
At work the next day Jack saw no sign of Nick whose wife Eve had fitted him up for the Guys and Dolls Ball. Was he deliberately keeping out of Jack’s way or, perhaps, his abandonment of Jack at the Ball had been legitimate. Interestingly, having been introduced to anal sex by Andy, Jack definitely felt some sort of affinity to his fellow staffers, most of them being gay.
On the Wednesday Jack came across Nick in the urinals. “Sorry I had to leave so hurriedly. It was a false alarm too. “Did Andy look after you?” Nick looked the picture of innocence.
“Sort of,” was all Jack dare say on the subject. H would dearly have liked to ask if he and Andy were in cahoots with each other. Instead he drew attention to the clothes Eve had lent him.
“Oh, don’t worry on that score. She said for you to keep them. You might find they come in handy.”
“Handy for what?” retorted Jack before he had thought about the implications.
“If you need to dress in drag another time of course,” Nick retorted simply.
Jack now had his first dressing-up clothes. That sent a thrill through his body. He pretended it hadn’t. Nevertheless, in the evening, he sought out an online site and purchased two pairs of French nickers, a pack of six cotton panties and two strappy camisoles. “Can’t do any harm behind closed doors,” he told himself.
Come Friday morning a call on Jack’s mobile revealed Andy’s number. Jack had been trying to convince himself that he wold not care if Andy didn’t contact him again. Of course that was a huge fib. Jack’s hand shook as he engaged with the caller. “Hiya Andy, how’s things?” He tried to sound nonchalant.
“Are you free this weekend?”
“I’ve got football Saturday afternoon,” replied Jack automatically.
“Oh, yes, I forgot about your commitment there.” The line went silent. Jack cursed himself for the answer he had made. He could throw a sicky. He had only missed one match before. “Teatime onwards then?”
“Yes Andy. where…..”
“Is it a home match?”
Jack had to think. “Yes, it is.”
“I’ll pick you up at five o’clock outside the ground. Does that work for you|?”
“The timing is a bit tight. Make it five-thirty?”
“Five-thirty on the dot then.”
Come Saturday, Jack very nearly threw a sicky as far as playing football. As it was, his mind was not fully on the game, and he was substituted shortly after half time. The team manager was not pleased, but Jack was not as concerned as he would have been before he had any dealings with Andy.
Andy picked him up right on time and seemed pleased to see his protégé. “Another party, darling,” he said familiarly, kissing Jack full on the lips. “We must quickly get you into your ladyboy clothes.”
“My ladyboy clothes?” repeated Jack intrigued.
“Yes. That’s what you are now darling. Don’t fight it. That is what you want to be.”
Jack was lost for words. he wanted to dress right enough. He couldn’t deny his cock was getting in on the act at the mere thought of it. But him – a ladyboy? What exactly did that entail? It was not far to Andy’s garden flat and there was some comfort as Jack walked into the now familiar surroundings.
“I guess you showered at the club?” Andy asked and receiving an affirmative nod, “then straight into the bedroom and get changed. I’ll make you a sandwich for you to eat in the car.”
Jack wasn’t being given the chance to object – that is how he saw it. Secretly, he wanted to go along with what was planned for him. He felt so alive again sexually. The trip to Thailand had awoken something in him and he wanted to experience lots more. Why shouldn’t he?
There was his new uniform set out for him on the bed. He undressed totally and, naked, did not turn a hair when Andy walked in the room and gave him a modern day version of a wolf whistle, and the compliment, “fuck me, you’re gorgeous darling.”
Jack, full of added confidence, rolled up his legs the black mesh hold-up stockings first. Then standing up straight, legs apart, and with his prick eighty percent, Luke was put into a quandary. “You’re fucking teasing me, you bitch,” he whispered appreciatively. Putting temptation out of the way. he left the bedroom.
A padded bra did nothing other than give the short, thin cotton dress some shape and the knickers this time were in the French style; ruby red with back lace edging.
The next job, cosmetics, threatened to be difficult. To cover for his lack of expertise Jack determined to keep it simple. A little eyeshadow, a touch of mascara and then a deep red lipstick. In the mirror he decided he “didn’t half look good.”
They arrived at the party late owing mainly to congestion on the way over. “You’ve missed the pairings,” lamented the host. “So did the Simpsons. You take Gavin, Andy and your companion goes with Bernie. Is that O.K.?”
Jack pulled Andy to one side. “What the fuck is going on here?”
“It’s a party where we all swap partners. It used to be that the tops put their car keys in a bowl and the bottoms dipped in blindfolded. Now Eugene, the host, does the selection, again at random so he says, on his computer. Looks like you’ve got Bernie, Gavin’s husband and I’m paired with the wife. They’re a nice couple. You’ll be O.K.”
“Jackie?”
Startled, Jack turned round quickly.
“I’m Bernie. Welcome to the party. Lets go and find a drink.” It wasn’t so much an invitation but an order. Jack was somewhat stunned as the man he was paired with was old enough to be his father and some.
Jack did not so much ask for a glass of red wine but was given one. Bernie was dominant, that was for sure. He asked questions as if it were a career interview. “So, you’re virtually a virgin, Jackie?”
The younger man felt as if he was blushing a bright pink. “I’m sorry,” he started stupidly….!
“Sorry?” Bernie smiled for the first time. “There’s nothing to be sorry about, young lady. You’re about to make an older man very happy. I’ll book a room. We’ll go up now.”
Jack found there was something sexually appealing about Bernie. He was smartly turned out, clean, and smelled strongly of a heavy perfumed body wash. His face and bald pate were nicely suntanned. He was carrying some weight, quite paunchy but it was his air of authority, his directness, and his expectation of being obeyed that probably turned on Jack the most.
Bernie came back with a smile of satisfaction on his face. “I’ve bagged the sunroom down the garden, for as long as we want it. Bribery is one of my many fortes. Wine or beer Jackie?”
Jack chose wine simply because he thought Bernie would prefer him to. Bernie picked up two bottles before he led Jack out into the garden. “What about a corkscrew?” Jack wailed.
They crossed a lawn and, even though it was still light, there was an outside light burning on the porch of what could only be the summerhouse. Inside it was a lounge, a small kitchen, shower and toilet, and a bedroom; the latter being equipped with a double bed of course. Bernie went straight to a kitchen drawer and rescued a corkscrew. He had been in that chalet before, obviously. He freshened Jack’s glass.
Jack took a big slug of the red Bordeaux as he watched Bernie remove his shoes and socks, and then his trousers and underpants. His cock was big and fat and his balls looked to be swollen with semen. Jack guessed what was coming in his direction and own his prick, totally enlarged, complained about being confined in his cotton panties.
With his cock swaying from side to side Bernie headed for the settee, throwing off his jacket and wearing just a shirt. “Come and suck me, young lady,” he ordered.
Jack didn’t need any second bidding although he took another scoop of wine whilst the opportunity was there. Bernie had his legs open wide in readiness and Jack merely knelt between them.
TO BE CONTINUED