A Ladyboy for Master Hans

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Amateur

After Chip had cooked dinner and waited on Hans, and had his own meal in the kitchen, cleaning up quickly, he got busy polishing Hans’s shoes and boots.

But in the middle of polishing Master Hans’s last set of boots, Hans interrupted Chip.

“Chip. How many times I must tell you? You have not written down your Stuhlgang, your poo-poo!.”

Hans, who was a strict hygienist, required that his submissive weigh and record his bowel movements, using little plastic gloves and a small digital kitchen scale, something that Chip was somewhat uncomfortable with.

More unpleasant were the results of such a weigh-in, which often could result in Chip’s being given a punitive rectal cleansing involving Hans’s Vaseline covered finger exploring Chip’s inner sanctum, and then inserting a douche nozzle connected to an enema bag.

Master Hans would then either give Chip a four quart boiling soapy water enema, or a freezing water one, and then plug Chip’s rectum, and have him clean the house while plugged, which was extremely uncomfortable.

Sometimes Hans would tell Chip he was untrustworthy, and would make Chip wear adult diapers, usually Depends or Serenity brand, for several days, and weigh the fecal matter himself.

Sometimes Master Hans could be even more cruel, and catheterize Chip’s penis, and not allow him to urinate for a day.

This often resulted in some quite amusing dancing on Chip’s part, and sometimes for Master Hans’s entertainment, he would make Chip wear tap shoes as the poor sub danced in agony, his bladder nearly killing him.

Hans would clap his hands and tap his feet and sometimes play polkas on the CD player as Chip danced miserably!

You’d think with all these punishments, Chip would not forget to record his bowel movements, but sometimes he still did.

Tonight, though, Master Hans only smiled beneficently, and waved his hand away. “You had a big day in town, and that disturbing fellow Q-Ball harassing us…I will forget it tonight.”

“Thank you, Master Hans.” Chip said humbly. But he had a question for Master Hans, and finally, Chip got up the nerve to approach him.

“Master Hans, why did we buy those odd things in town today?”

Chip was genuinely curious. Hans had purchased two miniskirts, three feminine blouses, a full makeup case, a wig and women’s shoes and stockings, as well as breast forms. Was Master Hans a transvestite?

Hans looked up from Friedrich Hayek’s “The Road to Serfdom” politely.

“They are for you, Chip, for your vocational training.” He returned to his book, but this apparently was not enough for Chip.

“Wh-what do you mean, my vocational training?

Am I going to learn to sell women’s clothes? What-what’s that mean?”

Chip began feeling a bit of panic as he asked. He sat down at Master Hans’s feet, so not to annoy him.

Hans looked very weary for such an energetic young man. But he finally dropped “The Road to Serfdom” on the floor.

“Chip. One of my concerns, and the concerns of others is that you have no job skills.” Hans pronounced this Chop skeels, but Chip tried to listen.

“You are not much of use, eh Chip?

I hear you read, and you sound like a child of five. ‘THE…CAT…RUNS..'”

Hans’s eyes bugged out and he spoke slowly like an idiot trying to spell out a sentence.

“That is quite sad, and you barely can add and subtract–“

“But I’m intellectually challenged, mentally disabled–” Chip said “It’s a learning difference–“

“It certainly is, and you should have been shot as an infant” Hans said cheerily. “However, I am doing the best I can for you as an adult.

You drop out of the ah, high school, and have spent many years wasting your father’s money.

Other than your proclivities for theft, which are not much because of poor eye-hand coordination, you know how to do nothing…

I was concerned for you until I realize you have one skill. And I will help you to turn that to money making…perhaps a career!”

Chip looked at Hans, with his head cocked. It was true that Chip had spent the last decade doing as little productive as possible…it was probably time he had a job, but what kind of skills did Hans mean?

Hans, seeing the puzzlement on Chip’s face, smiled.

“You were resistant to my efforts to teach you to suck on my eh, Schwanz” Hans patted his crotch,” But you have become quite adept after further training and a bit of encouragement from the cane, eh?”

Hans smiled, and of course Chip winced.

“So you have a rather slight build and a pretty face, Chip, and I think you could tire escort be a paramour for perhaps a rich burgomaster…after some practice as a prostitute.

The pay is good, I understand as many men in Buttermilk Falls are dissatisfied with the female prostitutes who insist on using a prophylactic, which deadens the senses to the penis when they perform fellatio.”

Hans smiled again, and lit a Dunhill cigarette.

“I believe” he said, as he puffed enthusiastically

“That you, although a stupid boy, could have quite a career using your mouth, and say your anus, provided you do not use the condom.

And so the clothes and makeup are for you, my boy. Tomorrow we will begin teaching you to walk and act like a woman, and then we will shave your legs and make you up, and then you can receive visitors.”

Chip gasped. Sweet Jesus. He had not been much enthusiastic about sucking Hans’s cock–Chip was as far as he knew, a committed heterosexual, and had been quite the cocksman in his day.

The first night in the cabin had been quite difficult. Hans had explained to Chip that he was to fellate, and Chip had certainly resisted, the way he’d once fought off an amorous cell mate in San Quentin…

But Hans had retaliated much more nimbly than Norville Grady, who’d wanted a little loving back in the hoosegow.

Hans had “trained” Chip…he’d hogtied Chip and stuffed a soap encrusted English cricket bat (where the hell had he gotten that?) into Chip’s mouth for a night or two. it had really wedged painfully…

And within 48 hours, Chip was willing, reluctantly to suck Hans’s penis…and then he also had to adjust to drinking Hans’s urine right from the uh, “spigot”.

Eventually Chip had been shocked to find himself craving the slim but muscular German’s body.

Hans was only seven years older than Chip was, not quite thirty, and Chip had not only begun enjoying sucking Hans’s penis, but running his tongue in between the cheeks of Hans’s ass and kissing Hans all over his nearly hairless body…but Hans was an exception!

But Chip didn’t know what to do about this one…what could he do to explain to Hans about not wanting to dress in drag and suck random dicks for money?

Chip didn’t think a foreigner like Master Hans would understand about human rights…and he was right, Hans didn’t!

The next day, Hans woke Chip early, and got him started in a pair of painfully small women’s pumps.

“I am going to order a man’s pair from the TransvesiMall, but until then we will bind your toes like the Chinese women, and you will learn to walk like a lady.”

Master Hans balanced a Encyclopedia Britannica (“Be-Bul”) on Chip’s head and Chip began walking carefully in the high heeled shoes.

It was quite painful. In a moment, Chip bent over, and the encyclopedia fell on the floor. Hans shook his head. “Posture, Chip…you must have posture…perhaps you need resistance!”

Hans instructed Chip to strip naked (except for the high heels) and he snapped a small chain between Chip’s pierced nipples, the only piercing Chip was allowed these days.

He then attached a two pound lead weight to the nipples so they sagged, and Chip bit his lip, but after an application of Hans’s cane, Chip straightened up manfully.

“Now then, Chip” Hans said softly

,” You will walk with your head up, your shoulders straight, in the shoes, balancing the books. Do not let the weight drag your nipples down, or I will put a heavier weight on there…let us see you walk!”

Hans then put on “I know what Boys Like” by the Waitresses, as Chip carefully walked up and down the living room floor, his toes killing him, not to mention his nipples.

“I know what boys like I know what guys want I know what boys like I’ve got what boys like “

Chip’s head tilted and the encyclopedia fell down, and Hans jumped up, and attached another one pound weight to the nipple clamps, replaced the book on Chip’s head and waved his hand for Chip to walk again.

“I know what boys like I know what guys want I see them looking

I make them want me I like to tease them They want to touch me I never let them “

“Try to move your hips a bit, Chip” called Master Hans. “You must be attractive as you walk up and down the floor in front of the discriminating gentlemen who you will be meeting soon.”

Chip was sobbing, but Hans ignored this baby-ish activity…he just closely monitored Chip’s walking.

After a week of eight-hour a day walking practice, Hans, with a rare sensitivity, showed Chip about makeup, moisturizer escort tire and how to sit in a miniskirt to show his legs to the best advantage.

Hans had said something about freezing Chip’s balls with ice and removing them, but after Chip had become hysterical, he’d dropped that line of interest…

“Perhaps, if this vocational training is not pleasing to you after a month or so, we can look at other alternatives.” Hans said soothingly.

“But presently you are quite useless, Chip…and we must make you as useful as possible!”

In another week, Chip was coiffed, and he’d gone through electrolysis at a discreet salon.

His nails were of a French manicure, and reluctantly, he had to admit with the enchanting blond wig, he looked a bit like one of the Olsen twins…well, perhaps in the dark.

“I’m so pleased about the progress.”

Mistress Holly said one night as they all sat in Buttermilk Brewmeistery…and indeed, most of the patrons were looking at Master Hans and the three beautiful women, only one of whom was born that way.

Chip, now called Charlotte was in a stunning gold lame top and sexy Capri pants, made of liquid metal lira. They clashed a bit, but the male customers didn’t seem to care. Cyrus, now Claudia was respondent in a purple sequin halter minidress with spaghetti straps.

When they’d gone to check their makeup in the bathroom, Charlotte had said to Claudia pleadingly, “Dad, I don’t want to do this! I realize your dream is to be a girl, but mine just isn’t!”

Claudia had paused in making an O with her mouth to apply City Lips Alcapinko Lip Plumper.

“Son, if you don’t want to do this, you can break off with Master Hans…I found it wonderful when he re-trained me from a drunken misogynistic sportswriter to a clubbing’ hottie, but you gave it a chance, and if it’s not your thing, okay.”

Charlotte checked her eye shadow.

“Dad, I really respect Master Hans though, and he’s teaching me so much. I’m afraid if I disappointed him, it would hurt more than some of his most vicious whippings!”

He’s…been so wonderful, and when I let him cum in my mouth, I feel so useful.”

Suddenly, the door to the restroom opened, and a auburn haired hottie from the bar bustled in.

Claudia didn’t even notice her, but Charlotte had been giving her the eye…of course the hottie didn’t realize that Charlotte was Chip.

“Be careful you guys” the auburn hottie said briskly. “There’s a real dorko near the entrance. He’s got like, a plaid jacket and a gross comb-over, he needs a rug BAD. He’s just so creepy.”

Chip/Charlotte took the auburn hottie’s arm and smiled, and said

“You are really beautiful, you know that? I can’t believe a woman like you is in such a pathetic place.”

It was Chip’s old pick-up line, but of course the girl just laughed in his face.” Sorry, I don’t swing that way…and you’re a little fat for me if I did, babe.”

Chip/Charlotte hung his head in abject shame. And the hottie ran on. ” Seriously girls, watch out for the creep!”

“Thanks sugar” said Claudia as he swiveled his hips and walked to the restroom door. God the practice, learning to twitch your hips like a girl!

Hans had had to lock Charlotte’s arms in a leather arm binder and then give Charlotte several brutal whippings with his Spanish horsewhip before Charlotte got the macho out of his step….it had been quite grueling.

Hans had also placed Charlotte into a Humbler for three nights…the Humbler consisted of two pieces of cherry wood “wings” with handles and locks on the ends.

The two halves of the Humbler came apart, in order for Charlotte’s testicles to be placed in the center carved out opening.

The wings of the Humbler were secured under Charlotte’s butt, with his balls locked in them.

When Charlotte tried to stand up, he was kept on all fours, as the scrotum felt a horrible dragging sensation, as the Humbler was, of course locked between his legs.

As Charlotte crawled around, Hans had whipped his locked testicles lightly and then not so lightly with a piece of secured barbed wire, and Charlotte had attempted to flee, not successfully on his hands and knees.

Then Hans had butt-fucked Charlotte while allowing Charlotte to masturbate with the Humbler on…and finally Charlotte broke…and promised to learn to hip-twitch for as long as the lessons took!

But now, Charlotte followed his dad out of the Ladies Room.

He looked for the creep that the auburn haired hottie had mentioned, but the only gross guy with a comb over and ugly plaid tire escort bayan jacket was now sitting with Miss Holly and Master Hans.

“Hello ladies” Master Hans said, smiling.

“This gentleman is Lloyd Weidner…he is quite prosperous, he owns five gas stations, and is looking for a bit of feminine company.”

Charlotte almost puked as he noted the way Lloyd Weidner was staring at him.

Charlotte tried to sit in a far away seat, but Master Hans brought him right down next to Lloyd Weidner, who immediately began stroking Charlotte’s thigh.

“Hi there, baby” Lloyd Weidner said, showing a mouthful of stained, filling filled teeth. The man had a CAR in his mouth, Charlotte thought.

“I’m just looking’ for a little company…you look just like a girl I useta date.”

Lloyd Weidner then proceeded to talk about himself for about twenty minutes, in the way that men did, dominating the conversation…

Charlotte noted that the auburn hottie and other authentic girls at the bar were giving the table a commiserating look…it was bad!

Suddenly Hans whispered in Charlotte’s ear. “I want you to practice on this Lloyd Weidner fellow, Chip….out in the parking lot…certainly this is not a realistic future husband for you, dear…but it is good practice in getting friendly with strangers.”

Charlotte whispered back “Are you kidding, Hans? He’s married. You can see the outline of where the ring was.

And besides, he is GROSS.” Chip/Charlotte was feeling rather nauseous.

There was no danger of Lloyd Weidner’s creeping fingers to find the outline of Charlotte’s cock, as it was pierced between Charlotte’s thighs, but Lloyd Weidner was still running his hands all over down there…

“Am I making ya hot, baby?” Lloyd Weidner’s whisper in Charlotte’s disgusted ear–Chip/Charlotte was in shock–was incredibly loud.

It was a stage whisper. Charlotte looked at Holly, and then to his father’s place–but apparently Holly had instructed Claudia to go talk to ANOTHER creep at the bar…disgusting.

“Go ahead, go outside with Lloyd, Charlotte…give him a good time!”

Holly smiled beneficently at Lloyd Weidner, who was stroking Charlotte’s inner thigh with one hand, and stroking himself with the other.

“She’s known as Parking Lot Charlie around here you know, Lloyd!”

Hans smiled, and kicked Charlotte violently under the table, and Chip/Charlotte knew he had to move.

“Please, Lloyd, lets go out to the parking lot, and have-a-good-time.” Lloyd Weidner looked earnestly at Charlotte..

“Sure you wouldn’t like t’get a room, honey, there’s a Motel 6 up the street.”

“No no” Holly interrupted.

“Our Charlotte has lots of dicks to suck before the night’s over. Let her take your dick in…she’s on the rag, after all, and can’t get laid.”

And the nightmare continued! Outside, Lloyd Weidner began unbuttoning his pants near his ancient Nissan Sentra.

“I shouldn’t have bought a Jap car, but the bitch ex-wife has taken all my money for child support…you want to get on your knees, Charlie, or go in th’ back seat?”

“Dude, I can’t do this” Chip/Charlotte said briskly.

“I um, have somewhere to go.” But as he turned, there was Master Hans, tapping his Black Derby Beechwood Walking Cane.

“Come on, you have work to do, Charlotte. Lloyd Weidner has already paid me.”

“Yup, twenty bucks.” Lloyd Weidner said, and now his gross dick was hanging out!

“No, I can’t do it, besides I might get a disease!” screamed Chip/Charlotte.

WELL DAMN! Lloyd Weidner had never seen anything like this happen at Brewmeisters! The chick, Charlotte was quite a slut, but…more of a bitch, right?

The old joke–a slut fucks everybody, but a bitch fucks everybody but you?

Well the Kraut fella wasn’t having any of it.

Lloyd Weidner watched in bemused drunken interest as the Kraut bent Charlotte over the front engine of Lloyd’s battered Nissan (Lloyd was really a gas station ATTENDANT, not an owner).

Yes, and pulled Charlotte’s shiny pants down and got that cane going on Charlotte’s ass. And then Lloyd got the BJ of his life. Yowza!

BUT THEN LATER? WHAT HAPPENED? DID CHIP BECOME CHARLOTTE PERMANENTLY?

The next day, after the Lloyd fiasco Hans offered Chip an “alternative”…he could go to community college, or take the course in air conditioning and heating installation at Buttermilk Falls Technical Institute, or he could join the Army…all wearing his own male clothes, clothing of his choice!

Today, the many years alcohol and drug-free Chip Thibodeaux has his own air conditioning and heating company in Cleghorn, Iowa.

Chip is married to the daughter of his Methodist Minister, and occasionally tells Cyrus Thibodaux III, affectionately called “Trey” that if he cuts up too much, Dad will send a postcard to Germany…to an old friend!

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